--- title: "Lenny's Podcast — 2024 Q4 合集" date: "2024-01-01" source: "Lenny's Podcast" url: "https://www.lennysnewsletter.com/" ---
# Lenny's Podcast - 2024 Q4 (17 episodes) This file contains 17 articles/episodes. --- ## [1/17] Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) **Alex Komoroske** (00:00:00): So much of the way that we tackle problems and build products is this builder mindset. It's like I have a plan. I then manipulate things to match my plan and make it happen. And this is a way you can create tons of value. Part of the problem though is it can't possibly create more value than the effort that you put into it. What I look for instead are things that can be gardened, things that can grow on their own and that you can direct or maybe give a little bit of extra energy to or curate over, and is a totally different mindset for it. If you do this properly, it looks like magic. I've been told that this is completely against all the advice that people get, including products nowadays, but I think it's a very powerful approach that works in a lot of different contexts. **Lenny Rachitsky** (00:00:40): Today, my guest is Alex Komoroske. Alex is one of the most original, articulate, and first principle thinkers on the future of product and tech that I've ever come across. This conversation will get your brain buzzing in all kinds of ways. Alex spent 13 years at Google where he worked on Search, DoubleClick. He led Chrome's Open Web Platform team for eight years, led augmented reality within Google Maps, and developed a new toolkit to align company-wide strategy from the bottom up. After a stint at Stripe as head of corporate strategy, he's currently founding a startup that aims to reimagine the web for the AI era. **Lenny Rachitsky** (00:01:13): In our wide-ranging conversation, we cover how LLMs and gen AI will impact how we build product in the coming years, what skills will matter most as AI becomes a bigger part of our lives, what companies can learn from slime mold, organizational kayfabe, the adjacent possible, strategy salons, why you should be thinking more like a gardener than a builder, plus a bunch of productivity tips, life advice, and so much more. This was such a fun episode, and I'm sure this is going to get your mind thinking in completely new ways. **Alex Komoroske** (00:02:01): Thanks for having me. **Lenny Rachitsky** (00:02:02): I love the way your brain works. My brain immediately starts buzzing anytime I start reading some of your stuff. And one of the more interesting things that you write and do and a really interesting habit you have is you actually have this doc that you keep called Bits and Bobs that I love, and we're going to be touching on a lot of the things that you share in this doc, Bits and Bobs, and we'll link to it. First of all, can you just explain this doc, Bits and Bobs, what's it about? **Alex Komoroske** (00:02:27): Yeah. I think it's like 600 pages now. It's this one Google Doc. Every so often, almost every day, someone will accidentally add a suggestion like add a space or something because it takes so long to load that while they're waiting, they'll tap on the screen and then it'll turn into taps on adding a comment or something. And I take a lot of notes. And people, I tell people when I'm in meetings with them of like, "If you see me on my phone or typing, that means I think you said something very interesting and I'm writing it down. It's not that I'm just that I'm disengaged. I try to collect all these ideas." And then once a week, I go through, I take a few hours and I just reflect to myself and try to find patterns and unpack and find meaning and things. And I write those down and I started sometime in the past sharing those publicly, and it's now become a thing I literally can't stop doing. **Alex Komoroske** (00:03:17): I just find someone who was like, "Oh, if you get more exposure for this, if you broke these up into tweets that you sent out once throughout the day," it's like, I did this for me. I'm happy to let other people see and peek into my weird mental process if they want, but this is 100% about my own self-reflection. And it's not designed. I don't want anyone to feel compelled to read it or... In fact, it's designed a little bit to be, I allow myself to be a little bit illegible. I want people to have to work a little bit with it. And it's not going to lay it out on a platter. It's going to jump between different things. I'll use terminology sometimes that is, what are you talking about? And I do that specifically. I don't want anyone to read and be like, "Oh, it sucks. It wasn't worth my time." It's like, "Cool." It's a 600-page Google Doc of my just unspooled insights. It's okay for you to not want to dive into that. **Lenny Rachitsky** (00:04:09): **Alex Komoroske** (00:06:21): I started it many years ago in the same conceptual thing, taking a bunch of notes. I have a thing called The Compendium, which is an open source tool. If you look at it currently, it looks like I haven't touched it in years, but that's actually incorrect. I built this about five years ago. I use it every day. And so I have, I think let's see, I currently have 17,248 unpublished working notes. And so what I do during the week is I'm taking notes very quickly in meetings, and then every day or two, I go through and I process them and put them in as working notes in The Compendium, and this is where I correct misspellings. I add just a little bit more context so that it will make sense to me if I were to read it in a year. **Alex Komoroske** (00:06:58): And also, I built a feature into it that uses embeddings to find similar cards. I find similar ideas from the past. And then what I do on Friday afternoons is I sit down and I go through all the notes I added that week and I just click and check the ones that still resonate with me, they still seem interesting in some way. And then I have a little export thing. I put it into a Google Doc, and while the kids are napping on the weekends, I just go through them and try to distill them a little bit more in a more long-term format. And then on Monday mornings, I publish them. And again, it's a deep... For me, it's like I can't imagine not doing this. It is the place where I find most of my most interesting insights is by reflecting on interesting conversations from the week before. **Lenny Rachitsky** (00:07:39): As we get into the conversation, people get to see how deeply you think about stuff. Part of the reason you're able to think so deeply about stuff is you have this practice where you take time to reflect and share and crystallize. There's so much power in just forcing yourself to write it out, I imagine versus, just not. **Alex Komoroske** (00:07:54): 100%. I find that when you're busy, you're constantly just go, go, go, go. There's no time to do any deep thinking. Deep thinking takes time and space, and you got to create that space. The mundane, pointless bullshit will take every square inch you give it. So you got to make that space to sit back and reflect and luxuriate in these ideas. And when you do, you're often like, "Oh my God. Oh wow, that's one I'll keep." And I told people, back at the very beginning of my career, I used to work from home on Fridays. And people gave me so much shit for this and they'd say, "Oh, you're working from home on Fridays." First of all, I will line up my output any day of the week. I'm very proud of the impact I've had. Second of all, Monday through Thursday, I'm in meetings from 8:00 to 6:00 or whatever. I'm just running between. I'm singing, pinging people and scheduling things and flinging action items. And the one day I don't take meetings is on Friday, and that's the day I read documents carefully that people had sent me or reflect. And I think to myself, what is the thing that if I had done it before the week started would've saved me tons of time and effort that week? **Alex Komoroske** (00:08:58): So for example, maybe in 10 different one-on-ones with people on the team, I had to explain to them a strategic thing that we were doing or a change that we were making. And the idea and the way I framed it worked for everybody. Well, you know what? That should probably be a document, right? If the same idea worked for 10 different people and now in the future there's probably 10 other people that need to hear it, and now I'll write that document in 30 minutes and now I have it as a memorialized thing that other people can read on their own time without having to involve me. **Alex Komoroske** (00:09:24): And you also find these interesting ideas sometimes where you look at this problem that you're banging your head against, you go, "Oh wait, if I will like that, that would've a wildly different dynamic." And you can only find those when you take a step back. And I find that people, I told someone, I mentored someone, I've mentored hundreds of PMs over the years and I told someone that at one point and they go, "Oh, I wish I had the time." And it's like, you got to make the time. All of us are busy and we will always be busy. And so this to me is not something I do to just for the enjoyment of all. I do deeply enjoy it intrinsically. It's something I do because I think it makes me more productive and effective. **Lenny Rachitsky** (00:10:01): I'm very tempted to go down a whole direction of just how you structure your time and your productivity calendar and all this stuff, but I'm not going to do that. That could be another episode if I do. **Alex Komoroske** (00:10:09): I do for that for hours. **Lenny Rachitsky** (00:10:10): What I want to do instead is pick on some of the Bits and Bobs that you've been focusing on noodling on that I think are going to be really helpful to listeners in how they think about product and the future of AI and all these things that I think are emerging. And the first one is actually that I want to get your thoughts on how AI and LLMs are likely to impact product development. A lot of the listeners of this podcast are PMs, engineers, founders, people building software, and you're spending a lot of time thinking about AI and product development. A lot of your Bits and Bobs have been just like, "Here's what's happening. Holy shit. This is how things are going to be." So let me just ask you this how do you anticipate LLMs and gen AI are going to change how products are built in the next three to five years? **Alex Komoroske** (00:10:56): I think they change a lot. I think LLMs are truly a disruptive technology. In fact, I would argue that what we're seeing in the industry is us trying to use mature playbooks from the end stage of the last tech era in one that doesn't really fit yet. To me, LLMs are magical duct tape. They're formed principally by the distilled intuition of all of society into a thing that operates between, a cost structure between human and plain old computing. So much of how the industry is built presupposes the idea that software is expensive to write and cheap to run, and LLMs undermine both of these. So it makes it LLMs allow writing shitty software to be significantly cheaper, not necessarily good software, but good enough in certain contexts. And also it means that there's certain software now that isn't plain old computing that can be run cheaply. It's relatively expensive marginal cost. **Alex Komoroske** (00:11:49): And so if you're going to do a consumer startup, it can't be based on advertising. It's just too expensive. Advertising cannot clear the inference costs even with inference costs declining. So I think the way to me, a disruptive technology changes tons of stuff, all these assumptions you didn't even realize you were making because you didn't realize it could be any different. **Alex Komoroske** (00:12:07): Imagine if you were locked in a room for your entire career, no windows, and you have all these experiences. You're going all this know how. You're getting this sense of how things work, what will happen. And then imagine that room tilts on its axis by five degrees. Everything looks roughly the same, and yet now the dynamics of the force of gravity is pulling in a different direction than it was before. You didn't even think about the force of gravity before because it was so omnipresent. It never changed that it's just a blank in your head. And now gravity has changed effectively for your perspective and all kinds of intuition is now wrong. I put this thing on the table, it's going to stay there, and then it slides off and falls into the wall. All kinds of weird stuff will happen. **Alex Komoroske** (00:12:44): And I think LLMs to me feel like that. I can't tell you the number of people who are... At some point at a year or two, someone came to me, they're like, "I just built a prototype, product that would've taken me three months. And I can believe it's going to start up." I was like, "How differentiated do you think that is?" Everybody can do that now. It changes the basis of competition. I think today I see a lot of folks using LLMs, and LLMs are like a squishy computer. We're used to computers doing exactly what we told them to do, which is not necessarily what we meant. And only some people have learned the skill of programming, the arcane magical incantations to make computers do exactly what you meant. **Alex Komoroske** (00:13:24): Now, LLMs can do all kinds of stuff. And they don't do exactly what you told them, but they do typically do roughly what you meant. I see all these places where people will build products and they'll say 80% of the time, 90% percent of the time, it's great. 5% of the time it punches the user in the face and they're like, "Oh, we're going to reduce the number of times it punches us in the face." It's like even if you get it down to 99% of the time, it's fine. If it punches in the face, that's not a viable product. And so how do you design your products assuming that this thing will be squishy and not fully accurate and fully work? **Alex Komoroske** (00:13:53): People use these things a lot as oracles. "I'm going to have it. I'm going to formulate the answer and it's going to be a fully fledged answer." And of course, strawberry has been really stabbed at. Gotten a chance to play with it. They are getting better at some of these kinds of behaviors at great expense. But in a lot of cases, I instead would rather say, "How can you take LLMs for granted? How can you assume that you now have this magical duct tape? Don't assume it's going to solve all your problems. Don't assume it's going to do autonomously be able to give high quality results of every case. But what can you now build now that you have magical duct tape?" **Lenny Rachitsky** (00:14:24): You're a product manager for most of your career. Now, you're a founder. I'm curious what your advice would be to product managers and people building products in terms of what skills they should lean into, what you think is going to be matter most. There's hard skills. There's soft skills. There's getting more technical. There's getting more product business-oriented. Just what do you think people should work on more and becomes more valuable and what do you think becomes less valuable from a product builder perspective? **Alex Komoroske** (00:14:52): I think in this early stage, we're in the community gardening phase, not the factory farming phase of this technology. And so I think what people need most is curiosity and play. You should be playing with these things and trying out different things and seeing what weird things are possible now. One of my favorite things, to be honest, right now, it's using AI is WebSim. WebSim is so weird. What a weird idea, like why? And then you play with it and you realize, "Oh, this is a thing that could only exist in a world where LLMs exist." And I think these kinds of odd, interesting, weird, provocative, generative things will be where a lot of the interesting patterns are found because right now we're so used to... If the playbook, if the cost structures have changed, the kinds of things are now possible, the playbook is wrong and we should throw it out or at least ignore it to some degree. So it will feel like we are navigating through a whole new industry that it has in the past. **Alex Komoroske** (00:15:47): Anytime that an industry gets really, really, really, really, really good at like vertical SaaS, we know how to execute the crap out of that. We know exactly what to do. It doesn't require that much. It requires consumption and execution velocity and all this. But vertical SaaS, I think, is not the right model of how you would attack a problem that is an AI native style problem. And I think that those are where all the interesting things will be. And again, I think a lot of the tactics that we're trying out at the beginning, they won't work. It'll turn out that they only work 95% of the time, and 5% of the time they punch you in the face or something. And that means that you have to be more adaptable and you have to assume that a scrappy thing will be more important. **Alex Komoroske** (00:16:28): One of the ways I put this is we've seen a vast reduction in the cost of distribution of information, and now we're seeing a reduction in the cost of information production. And most of it is slop. And so in this cacophony, how do you stand out? You stand out by having good taste. I think taste is the most important thing. You have a perspective that is different from the background noise, different from the average and that people find compelling. How do you find your own taste and how do you lean into that taste is, I think, much more important than just generically executing in the way that everybody else could do. **Lenny Rachitsky** (00:17:01): There's so many threads I want to follow here, but maybe on just this last one, when you say taste, what do you mean by that? What should people think when they're like, "Okay, I got to work in my taste"? **Alex Komoroske** (00:17:09): Taste, one way of looking at this is differentiate from what the LLM would've written if given the same prompt. How different, how distinctive is what you have to say. And I think so much in large industry, in large organizations is about fitting into the role. How can you be a better and more efficient cog in that particular kind of machine? And I think in this new world, what you want to do is how can I become the best version of myself? How can I lean into the things that I have an interesting perspective on that make me different? Those are the kinds of things. And now of course, if you lean into something and you're doing something out there and nobody resonates with it, then it doesn't count. Good taste is something that is individual and also compelling to others. And so find what things you say that resonate with other people and lean into that. **Lenny Rachitsky** (00:17:53): I love that. Back to the WebSim example, we're going to link to this, but definitely play with WebSim. I was interviewing Dylan Field at Figma Config and this was his... Asked him like, "What's the number one thing you think people are going to get more excited about in the future that you're playing with now?" Because he's really good at identifying things that are going to be bigger in the future, and that was his choice. And it's very hard to understand exactly what it is if you just go there. But basically it's like you type a URL and it invents what that website is using just AI LLMs. **Alex Komoroske** (00:18:22): That's insane, as in. And you can get it to do, you realize as you play with it more, you can get it to do all kinds of specific things and you can steer it based on the way it uses the context of the last few pages. It creates a coherent world that's coherent with the things that you have recently seen, because you can steer it directly and you can watch fascinating people. They'll cover all kinds of wacky little techniques to get to generate, like generate a game for your kid that's on a specific type. You can do all kinds of stuff. And I'm not saying necessarily WebSim to me is a disruptive thing. Things that look alien and weird and yet are compelling, those are what we should be paying more attention to as opposed to take an existing playbook and slap something on it. **Lenny Rachitsky** (00:19:03): I love that. Another point that I saw you make about AI and the way it's different from other things we've done is most of the tools that we adopt in the workplace are collaborative where it helps your team be better, helps you collaborate better, and AI is the opposite. It makes you individually better. Can you talk about that insight? **Alex Komoroske** (00:19:18): 100%. I think this is one of the reasons is that the question right now of, okay, everyone's talking about AI and yet nobody's doing... There's no interesting breakout success obviously other than OpenAI and Anthropic obviously. So is there any value being created? I think it's entirely possible. And Ethan Malik who's a good friend, who has an amazing blog who's absolutely worth reading, has pointed out, too, that this is a thing that make individuals better in a way they might not want to tell their manager about. I can now do my job twice as fast. And if the organization sees that, they might go, "Wait a second. We should pay you half this much." They're like, "What if we get rid of some extra people or something?" **Alex Komoroske** (00:19:56): And so if this stuff is magical duct tape, it's very hard to make scaled, repeatable, large scale things out of it. It's very easy to do rig the shit out of anything. And so you'll see it being used in the small in a way that's almost entirely below the level of awareness of the seeing at the organization. The organization almost won't see it or sense it, and yet it could be adding significant value or just being used quite heavily. And I think this is one of the things that makes it if everything is happening in the long tail of usage, then you could conclude, "Oh, it's not being used for anything in the industry," but it's being used all over the place. I talked to Claude 20 times a day. I just have long conversations with it. I have tons of projects loaded up with all kinds of contexts on different topics, and I literally could not do the job I do now without having a conversation partner like Claude. **Lenny Rachitsky** (00:20:48): Let me follow that thread real quick because a lot of people are like, "Okay," people keep telling me, "Play with AI. Use ChatGPT." Sometimes it's hard to see exactly what they can do with it. Can you give one example of how you found it really helpful or how you use Claude or another tool in your day-to-day? **Alex Komoroske** (00:21:02): I use it to think through problems. And so like when I'm trying to name a concept or get a handle on a few different ways of looking at something, just saying, "Here's what's in my brain about this topic right now. Here's some relevant context." I have a number of projects that just stuff as much of the Bits and Bobs into the context as I can, which is very helpful. And I just say, "Just play with it. Just give me 10 examples of that thing," or then, "Critique these ones," or, "It feels like this one's the best one for me. What works about this? Why is this one the best?" Or, "I want to work at an angle now that has something about know Helen Nissenbaum's concept of contextual integrity. How would I layer that in?" It's just think of it as having a extremely well-read but slightly naive friend who is will never make you feel dumb and is willing to engage you in any particular topic you want to go down. **Alex Komoroske** (00:21:49): So when you talk to an expert like a lawyer or a doctor or something, you know that that time is extremely valuable. You have a very small slice of time, and so there's tons of questions you don't even bother to ask. "That's a dumb question. I'm not going to spend $1,000 to answer that question." Whereas if you can have that conversation, now this is not saying use it for legal advice, but it can allow you to explore through a problem domain and then later check it with experts and say, "I believe this is a coherent outcome or a thing that should happen." And they can go, "Oh yeah, that works." So I use LLMs to help me. It's like getting a, it's like an electric bike for idea spaces. You can just cover so much more ground so much more quickly in them. **Lenny Rachitsky** (00:22:26): I love that metaphor because it builds on Steve Jobs's that computers are a bicycle for the mind. And that's really a beautiful way of thinking about it, that LLMs are like the electric bicycle for the mind. **Alex Komoroske** (00:22:37): I don't think if that's someone else's, the... **Lenny Rachitsky** (00:22:38): Oh, okay. **Alex Komoroske** (00:22:39): I don't know where it came from. Part of my job is a collector of ideas, and so I try to put myself in the most interesting information streams with interesting people that I've found to have taste, have a perspective on something. Maybe I disagree with it, but they definitely have a coherent idea. And then I just allow myself to like, "Oh, that's a really good idea and let me build on that or let me..." I don't even know where that particular one came, but I'm 95% sure that somebody else said that. **Lenny Rachitsky** (00:23:05): I want to get to this idea of gardening versus building that is central to a lot of the way you think about it. But before we get there, I want to touch on another bit and bob that I love that you come back to occasionally, which is this idea of organizational kayfabe. Talk about what this idea of kayfabe is on its own and then how this applies to organizations in your experience. **Alex Komoroske** (00:23:26): One thing I should flag before I dive into any this stuff, sometimes when people hear me talk about how organizations work and systems, they think I'm being cynical. And I want to be very clear, I'm hyper-optimistic and I also believe that one of the moral precepts is how do you maximize the agency of real humans as ends in and of themselves? And so sometimes when I get excited about this, people go, "Wow, that is so cynical." No, I'm just trying to describe the system as it actually exists. Once we know how it exists, we can figure out how to make it do great things and how we as members of this system can tweak and nudge it. **Alex Komoroske** (00:23:56): So I just want to flag that before I dive into this. I have this slime mold deck which has gotten a ton of traction over the years, and part of the reason for that is because it feels like people tell me it feels like they think they're crazy and it feels like giving a big hug saying, "You are not crazy. Here's why this thing shows up." And once you acknowledge it, it feels like a bummer to acknowledge it, but once you do, now there's all kinds of options that pop up. "Oh, given that this thing is way more expensive than it looks, I can now do this instead. That one's 10 times cheaper. These two options, this one is way cheaper, way more likely to succeed." So once you see these forces, you see them more clearly. **Alex Komoroske** (00:24:28): So kayfabe is I think a lens that's useful to understand how organizations actually work. Kayfabe is a word that comes, I believe is a carny word that is used and applied to professional wrestling and it means a thing that everybody knows is fake and yet everybody acts like is real. And I think it's one of the defining forces within an organization, any organization. So kayfabe in the small is optimism, enthusiasm. When someone says, "We're going to do this thing," you say, "Yeah, we're going to do that," even if I think this isn't going to work. If you say, "I don't think this think is going to work," everyone loses hope and it definitely doesn't work. So having a little bit of this is extremely valuable. It's the lubricant that allows organizations to believe they can do something and to attempt to do it. **Alex Komoroske** (00:25:09): The problem that you get is as organizations get larger, imagine you are five levels down or something and you have this project you're working on and you're trying to give a status update to be rolled up to leadership. And it's currently a yellow, and your manager asks it and you know it's not going to be presented to leadership and enrolled up until next week. "It's yellow, but I've got my arms around the problem. I know how to fix it. I'm going to go talk to Sarah. I think we have a solution. By the time this is reported up the chain, it's going to be green." So if I make it yellow, there's a non-trivial chance that someone's going to swoop down and say, "Well, what's going on? We have a review," and it will be way harder to fix, so I'm just going to... A little white lie. **Alex Komoroske** (00:25:46): This is a totally reasonable thing to do. It's a self-defensive thing to do. And it's probably the right thing for the organization too. The problem is this happens up multiple layers and it compounds. So then your layer above you does the same, and the same, and the same, and levels up you can be many orders of magnitude off of the ground truth. And so the kayfabe, the thing that everyone pretends to believe is true, is obviously incorrect. And the dangerous part about this is it can lead you to make very bad decisions. And if you as someone who sees this can see that wait a second, the official strategy is definitely not going to work, you're like, "I got to tell somebody. We're doing work that's going in a bad direction. It's not going to work." And you go and say, "I think that it's actually not going to work for these reasons." **Alex Komoroske** (00:26:27): And what someone will say to you, this happens by the way, I'm not substituting any particular organization, this happens literally in all organizations to some degree, is the senior person will say, "Alex, I agree with you. It's not perfect, but if you hit the ground truth button, if you share that and everybody, the whole thing will shatter and we can't do anything. And so help me fix it. Don't say the ground truth. Just help nudge it and fix it." That's a good point. Okay, so you help working on it and then you realize a month later, wait a second, it's getting worse. We're doing things that's not good for the company. It's not creating user value. It's not good for the employees. They're burning out. It's just not good for anybody and it's getting worse. And so if you think you're going to go and hit the ground truth button, before you do, you'll be flying tackled to the ground by somebody and stabbed in the dark because you will destroy everything. **Alex Komoroske** (00:27:13): And so it becomes correct to hold onto this idea of if you acknowledge the kayfabe is false, then you are in danger of getting knocked out of the game. And so how do you do good things despite the fact that you're pulled in two different directions? And this increasingly in the limit, it can be good to a point where the easiest way is if I do, if I hold on this idea, we might create significant value for the company. If I let go of this idea, I die. So the easiest way to maintain this split-brain thing is to just turn this part off and just earnestly believe the kayfabe. This has been organizations become zombies, and anyone individually you talk to behind the scenes will agree yes, it could not possibly work. That turns out that these things work this way, and yet the entire organization lumbers on. **Alex Komoroske** (00:27:56): And this is a death state for large organizations. It happens all over the place in any number of different conditions, and this is one of the reasons it shows up. And I think acknowledging that is an important way to help navigate and still make good grounded things happen. How can you allow disconfirming evidence to show up that doesn't kill you, that helps make you stronger? And if it all has to come in one massive moment that could ruin everything, then you aren't going to hear it. And then it will build up and build up and build up and build up into a super critical state that could shatter. **Lenny Rachitsky** (00:28:27): I was just listening to a couple podcasts, and a thread that came up in a number of them is some of the most successful leaders, their instruction to their reports is, "As soon as there's bad news, I need to know as soon as possible. Do not shield me. I just want to know all the bad news as soon as possible." Feels like that's one solution to what you're describing. **Alex Komoroske** (00:28:44): Disconfirming evidence hurts, and so you won't realize it because it hurts at any given moment. It's like, "Ugh, it's a distraction. We're just trying to get this thing done." And so it comes from a good place to not get it, but if you're busy, that's one of the reason you need to take a step back. We take a step back, you're a little bit calmer. You can absorb this as confirming evidence. It doesn't feel like an existential threat. It's really easy to get surrounded. If you are very powerful, you will find all the confirming evidence you need. And if it doesn't exist, it will be created for you without your knowledge. **Alex Komoroske** (00:29:12): And so this is one of the reasons that large companies are radically different than smaller companies. And one of the traps that you can get into of not realizing this dynamic is happening, and you can make very bad decisions if you don't understand that it's inherently what's happening because they're all, "Oh, we'll have some bad actors." No, no, no. If people don't play this game, this game is emergent. It shows up even though everybody hates it. And if you don't play the game, you are knocked out of the game. The underlying dynamic that must be true in any organization on a fundamental basis is you can't make your boss look dumb because if you do, they're the person who decides, "Oh, this person's not performing," or whatever. And that one little asymmetry, that one little fact, in most cases it does not matter. That one little asymmetry is what leads to the systemic compounding thing where you get these really weird dysfunctional emergent things that everybody hates, nobody wants, and yet nobody is in the position to change per se. **Lenny Rachitsky** (00:30:05): I love your caveat at the beginning that continues to resonate in my head as you say this. You're not cynical about, "This sucks." It's more, "Here's what I'm observing. We need to think about ways to get around this." **Alex Komoroske** (00:30:16): Yeah. Because I think so much pain and misery is caused by us being not acknowledging these fundamental, inescapable things. It's almost impossible. Entropy is one of those things. Entropy emerges because there's more ways to go away from a point than towards a point. It fundamentally must be true in really any universe you can possibly imagine. And so if you're going to fight entropy, you're going to lose at a certain point. It's like if you are aware of these things, you can find subsets of ideas that do work despite these challenges. And that's some of the stuff, the tactics I advise are often things that look playful. They look unserious. They look like, "Oh, you're saying you don't know the answer?" No, I'm admitting I don't know the answer. **Alex Komoroske** (00:30:55): And I'm saying it doesn't matter if I don't know the answer because this thing, this very small seed I am planting is so cheap that yes, I can't tell you for sure this will work, but I could tell you there is a chance that it'll work. And the downside of this is basically the opportunity cost of planting the seed in this one moment, and the person who's planting it enjoys planting it so that an opportunity cost really isn't that much because they get energy from doing it. So who cares? Plant a bunch of these suckers. If one of these grows into an oak tree, that's great. Don't try to analyze beforehand which seed is going to turn into an oak tree. If it's super simple to plant the seeds, then plant the seeds. And if it starts growing, then keep watering it. That's it. That's the thing. **Alex Komoroske** (00:31:30): And people sometimes will see this as like, I've been called in my list before because they said, "Well, you're saying that you don't know the answer to the thing." It's like no, I'm saying I don't have to know the answer to the thing. If on a systemic basis I let these ideas and then you respond to the ones that are working that are viable, it doesn't really matter if you didn't know ahead of time which ones were going to work. **Lenny Rachitsky** (00:31:48): It's a great segue to talking about this core idea that again informs a lot of the way you think, which is this idea of building versus gardening, the magic of acorns. Talk about this general idea and then I want to follow some threads. **Alex Komoroske** (00:32:02): So much of the way that we tackle problems and build products is this builder mindset. It's like, "I have a plan, I then manipulate things to match my plan and make it happen." And this is a way you can create tons of value. Part of the problem though is it can't possibly create more value than the effort that you put into it. And so what I look for instead are things that can be gardened, things that can grow on their own and that you can direct or maybe give a little bit of extra energy to or curate over, and is a totally different mindset for it. So it's like a lead by gardening vibe. I don't try to pick the things in the system. I try to work with what I've actually got and I try to lean in on the ones that turn, I think are going in the direction that I believe is valuable based on constantly seeking disconfirming evidence. **Alex Komoroske** (00:32:44): And if you do this properly, it looks like magic. It looks like a thing. It looks like getting lucky because what you're doing is you're farming for miracles. And so on a systemic basis, I can't tell you which of these things will work, but I can tell you there's a very high likelihood that one of these will work in a way that is interesting and transformative. And so if you're looking and finding these seeds that have the compounding potential of if they work, they would start working at an accelerating rate, then you don't have to know ahead of time. To me this is, I've been told that this is completely against all the advice that people get building products nowadays, but I think it's a very powerful approach that works in a lot of different contexts. **Lenny Rachitsky** (00:33:26): Is there an example that you can give from either from something you worked on or something someone worked on that came or true miss? Because I think people hearing this might be like, "But I got to ship stuff. I got to hit some goals. I don't have time to sit around and garden and plant seeds. I got to actually build." **Alex Komoroske** (00:33:41): If there's an ecosystem approach, if there's something that if it works, it'll be self-accelerating. So okay, what you're going to do this thing, we aren't entirely sure what's going to work, but if a developer writes a thing and somebody uses it, it'll attract more developers, more users, and then this would grow on its own. Then and it's cheap to do the little example of the thing. It's cheap to build a little open source, tinker the little thing and just put it there. And if nobody uses it, it's fine. It was fun to build. It took you three hours. It's fine. If someone does use it, then you just invest in incremental bit of unit each time that you find a signal that somebody is finding it useful and then you stop if you ever cease getting that information. **Alex Komoroske** (00:34:16): So I would use this. Anything that is shaped like an ecosystem that has some kind of network effect, and many things have network effects, have some kind of compounding loop. Compounding loops are not rare. They are, "Look." It's like truffle hunting. You have to know what you're looking for and find the dynamics of a thing that if it worked would work at an accelerating rate. Lots and lots and lots of things intrinsically have this shape. Anything with a network effect, anything where the power goes up with a number of users, but it shows up in all kinds of problems that we don't normally apply it to. **Lenny Rachitsky** (00:34:47): Along the same lines, you also advise people to think more emergence-oriented versus top-down, kind of what you were just saying. But I think that's another really interesting way of thinking about the same idea, create opportunities for emergence, bottom-up versus top-down control. You just chat about that. **Alex Komoroske** (00:35:03): 100%. I think the emergence is one of the most powerful forces if you know how to marshal it and you know how to work with it. And the only thing that's hard about it in my opinion is you're going to look like you aren't very serious. You're going to look like a weirdo. You're going to look like a cook. And one of the downsides, if you're working on something and you're doing the normal top-down approach where you make the plan, you execute the plan, even if the plan turns out to not be useful, you produce a thing and nothing interesting happens, no one can say you didn't work hard. But if you try doing this designing for emergence and something amazing happens, even once it happens, people go, "Ah, it's luck. Where was the miraculous moment, the heroic moment where you made that happen? So therefore you had nothing to do with it." **Alex Komoroske** (00:35:42): And this was the biggest unlock in my career actually was when I stopped my guts. I was promoted to director at Google. I was like, "Cool, I never want to be promoted inside of a large organization ever again." And the freedom to now do the highest impact work, even if I can't make it legible to the organization, was so powerful and I was able to 10X my impact for the organization because I didn't have to worry about making it measurable specifically in a way that would show individual work effort. And I think that's the hardest part. And you have to have, typically what I would advise for PMs, my approach at Google was 70% of my effort and my team's effort should go on things that everybody acknowledges are important and useful and create value. Maybe it's boring, linear value, but some kind of value. You're trying to minimize the chance that any other person in a company will say, "What does that team do anyway?" **Alex Komoroske** (00:36:32): This, if someone says this about your team, your team is on the verge of death. And so you're trying to minimize the chance that anybody wants to say that or thinks that it's appropriate to say that by clearly and unambiguously adding value. You're not saying this is the best team in the entire world, but clearly they're doing something useful. They're executing well. They're working hard. And of course that team should exist. Think about it, of course they should. But now once you do this, you have 30% of your extra time that you can plant all these seeds. **Alex Komoroske** (00:36:55): You can find interesting little things where maybe a junior PM on the team has an idea you think it's kind of silly, but they're really into it. And the there is this thing, it could work out great actually. If you tweak it like this, there is a potential. I could see how that could work. If that PM is going to work on that anyway, they want to do it anyway. Instead of saying, "No, no, no, we don't have time for that. Be a little bit more productive over here," say, "Go for it. Here's my concerns. I imagine this part might not work, but this part is really cool right here." And then if it doesn't work, then they've stretched their agency. They've executed. They've exercised their agency. They've learned. They've gotten stronger. They've grown. It has the upside if it turns out to actually work. And worst case scenario, the opportunity cost to doing the thing that helped them grow and they learn and they liked. So I don't know. Don't try to force it. Don't try to stop it. **Lenny Rachitsky** (00:37:40): That's a really good example of actually how to go about doing that on your team. The way I've always thought about this is the visual I share with people is like, you want to create cover fire for your team where your team's just hitting goals, moving metrics, and then while with that cover fire, you're building the doomsday bomb inside, protected where no one's going to come and stop you. **Alex Komoroske** (00:37:58): Yeah, because one of the hardest parts about an acorn when you plant it is making sure a squirrel doesn't dig that fucker up. There's so many things that can destroy it, and just keeping it, allowing it some space and allowing it some time is the most important thing. And it's challenging to do, but that's why it's important as a leader to have enough credibility in the organization that people can see that you are doing useful work to give you the space, to give your team the space to do this truly great work. If you want to get your team to do good work, there's a million different paths to do that. If you want to get your team to do great work, there's no shortcut other than to have an extremely high-trust environment where people lean into their superpowers in a way that adds up to something greater than some of its parts. That takes time. It takes effort. It's very difficult to make legible up to the rest of the organization, but that is where great things come from. **Lenny Rachitsky** (00:38:46): It reminds me of something Ed Catmull shared in Creativity, Inc., this idea of the ugly baby, that every new idea is an ugly baby and nobody wants this ugly baby. Everyone's just like, "Get this out of here," because every new idea is bad initially. **Alex Komoroske** (00:39:00): Yeah, it sucks. They're just like this ugly thing that barely works or... But this is why what I try to do is I try to see the greatness, the seeds of greatness in everything. Everyone and everything around me, I look for, I try to find and see, man, what is the most compelling part of this? And let me lean into that. And so one of the things I try to do when I meet with people, when I mentor them, I try with it within the first session or two, whenever I can get a hypothesis, I say, "I think your superpower is..." And I describe to them what I think I can see them being truly exceptional at. **Alex Komoroske** (00:39:31): And sometimes I get it wrong, especially if I try to do it earlier, but when people feel very seen and they feel acknowledged for that, they now are willing, they're going to stretch farther and they're going to respond to nudging feedback even better because they know that you're not trying to tell them be different. You're trying to tell them be more, and you now the nudges will feel less like a stop energy and more like someone who gets me and can help me grow even more. And you can get some amazing things out of people when you just treat them with the respect. I assume that everyone I talk to, everyone I talk to is interesting, has seeds of greatness in them, even if they don't recognize necessarily where they are. **Alex Komoroske** (00:40:08): Someone described to me actually this morning in one of my little dirt clubs I run about they help facilitate about treat everybody like the Buddha. I think is I'm messing this up, but this notion of imagine everyone you talk to is the Buddha, in a Buddhist mindset, and how do you see and find those seeds of greatness and treat everyone with respect intrinsically as an end of themselves. This is one of those things that you do to be a compassionate human. It's also, I believe, a way to maximize the amount of value, direct and indirect value, that's created. So it's one of those win-win-win-win-wins where just it's the right thing to do as a person and a member of society, and it's also the thing that can create a lot of business value and create real value in the world. **Lenny Rachitsky** (00:40:49): **Alex Komoroske** (00:42:32): Yeah. The main thesis of the slime mold deck is that the core dynamic that makes organizations hard to navigate as they get larger, even if you assume everyone is actively good at what they do, actively collaborative and actively hardworking, is this emergent force or coordination of finding the subset of projects to work on when everyone's super busy that everyone agrees and commits to and actually works on together. And finding this coordination cost grows with the square of the number of people who are working on that thing. And so what companies typically try to do is fight this or ignore that it exists. **Alex Komoroske** (00:43:06): If you're going to fight it, the one way to look at this is think of a company like a vehicle. When the company is very small, you can drive it, you can steer it like a sports car. As a founder, you are allowed to steer. Everyone acknowledges you are allowed to steer. They're never, "Why is he steering it that way?" So you, a founder, can help navigate an organization around an obstacle the organization cannot see or comprehend itself. The problem is as you steer, as you grow into the size, your organization goes from a sports car and you grow into the size of a big rig, if you drive a big rig like a sports car, you're going to be a danger to yourself and others on the road and you're going to grind the engine. And so you got to drive the car that you actually have. **Alex Komoroske** (00:43:41): So what I see a lot of things happen in large organizations, that people are just trying to ignore this fact. And when you drive, by the way, a car, your vehicle, like a big rig, when it is a big rig, people go, "Oh, it means to go slow." No, no, no. It means pivot less. It means have a little bit more... Be more intentional about the times that you adjust the steering, invest more in program management, invest more in processes, give a little bit more slack in the planning process to absorb any kind of surprising things that you can still all reach the product launch at the same time. **Alex Komoroske** (00:44:13): The other option you can do is you can split your thing up into a series a swarm of sports cars, individual sports cars. And the downside of this, you'll get the autonomy and strengths of the bottom-up, the downside is other people will externally will look at it and go, "Well, that team and that team clearly didn't talk." You'll say, "Yep, yep." You have to decide how bad that is for you. Apple has chosen the former. It's very important to them to have the illusion of perfect coherence in their products. It worked very well for them. They executed marvelously. And if you also picked the exact opposite thing, everyone else is like, "Yeah. There are like 15 different ways of doing everything. They clearly don't talk to each other." But it allows the overall swarm of the AWS product suite to be very powerful and anti-fragile or whatever you want to say. **Alex Komoroske** (00:44:52): And so slime molds, I think, is acknowledging that organizations are, especially ones that focus on autonomy and agency of their individual employees, which is a lot of tech companies, they are more like slime molds than we realize. And if you fight that fact, you're going to have a bad time. And if you embrace it, then you can start realizing slime molds are actually kind of amazing. They can find solutions to problems you didn't even know you were searching for. **Lenny Rachitsky** (00:45:15): Alex, you have the best metaphors. I don't know how you do this, but they're so evocative and correct. **Alex Komoroske** (00:45:21): I can tell you that the process I do if you're into it. **Lenny Rachitsky** (00:45:23): Please. That would be incredible. **Alex Komoroske** (00:45:25): I think by talking, I'm an external processor, I literally can't think if I'm not talking. And so I make sure I have as many interesting meetings as I can, and that's where I discover what I think, by talking to people. And the test is if I say a frame, something that the person goes, "Ooh," or like, "Ooh," they go, "Aha," that's a win. That's a mark that's a good one. You're just randomly casting about. I find one. And then if a different person also has a similar response, if a person in sales and a person in engineering both find the same idea interesting, that's a very good sign that lots of people will find it interesting, how diverse in terms of background skill sets, perspectives are the people who resonate with the thing you're saying. **Alex Komoroske** (00:46:08): The intuition of this is if you find in a social network, you want to see what's going to go viral, if something is shared and it's shared within, so the people who are at the beginning are all highly densely interconnected in the social graph, then the implied ceiling is relatively small. You only know it works with that audience. But if it's people that are very different subclass and very little overlap, they both find it interesting, that implies a much larger max audience. So you're looking for ideas that resonate with the diversity of people. And then once you find them, each time you get something like that, you invest a little more time in it and you think a little bit more about framing it the next time. **Alex Komoroske** (00:46:42): I haven't done this during this chat, but in most conversations, you'll see me as I'm talking writing down stuff like, "Ooh, that was the best formulation of that one so far." And so you keep on coming back to it. You keep on tightening it and seeing how, watching how it's responding and referring with different people through like, "Where do you get these from?" It's like I got thousands and thousands and thousands of little examples or metaphors or whatever that's sick. **Alex Komoroske** (00:47:03): One of the benefits of metaphorical thinking is you connect nine of the 10 dots and you invite the listener to engage with the argument to connect that last dot. This allows you by the way to say very controversial things, because if you say connect all the 10 dots and it's like, "Oh, that's the official strategy," then you are instantly a dangerous thing. Whereas if you leave one dot unconnected, people can go connect the dot and go, "Oh my god, I think that applies to us." You're like, "Oh my god, what?" "Yes, that's why I picked that." But to counteract this because now it's less obvious to people that's correct, you have to make the metaphor evocative and interesting. **Alex Komoroske** (00:47:39): One of the reasons that slime mold deck got so much traction is partially because slime is gross, it's bad, and yet it's talking about why slime is good. And so that has this instantly subversive thing. I only know this after the fact of trying to figure out why did that deck get so much attention of all the things I've written. **Lenny Rachitsky** (00:47:56): It also is all emojis basically, which is not how you often read a deck. It's very beautifully made. I love that you've been talking about the way you think and come up with ideas is by talking to people and having conversations. We also talked about how you write in this Bits and Bobs approach. I asked someone that you worked with at Stripe what to ask you, and she said to ask you about strategy salons, which feels like a good avenue for this sort of thing. Can you talk about what these are and how you set these up? **Alex Komoroske** (00:48:26): So these I also call now nerd clubs, and these are my secret weapon. And I have a blog post. I started writing right before my second kid was born, and then he was born three weeks early and I just lost the plot and now it's like a 40-page draft of a thing that I'll probably never finish. But I've used this tactic. I discovered it many years ago as they strengthen some of the techniques I'd used in open source community organizing. And the situation was I was just joining a new team at Google. I've been there for many years, and there was at the time 12 different groups working in different aspects of this overall problem domain. And in classic Google fashion, they added up to significantly less than the sum of their parts, as in not like, "Oh, we'll see which one works," but, "These two things directly undermine each other. If you execute both of these strategies, neither can work." And I knew that if you try to do pairwise executive reviews on this very complex, ambiguous, open-ended problem, you would get really expensive pageantry that would obscure more than clarified. **Alex Komoroske** (00:49:17): So what I did was I created a secret group that I called Navel Gazers was the original one, and I wanted people when they hear about it, I want people to go, "That will be a club for nerds." They're like, "Yeah, do you want in?" And so this means that only people who intrinsically want to be in it for its own sake come in. So you get only a positive "yes, and" kind of energy. So then within these groups, you say, you set the norms very explicitly and say, "This is a collaborative debate environment. This is only 'yes, and'." If somebody says a thing in this group that is optional and secret and completely off the side of anything that matters, if they say something that you think is an actively dumb idea, you are free to not engage. Just leave it. That's fine. Because nothing's going to happen. We're deciding anything interesting or important here. **Alex Komoroske** (00:49:57): And if you want to engage and you don't like it, a productive way of doing that is saying, "Oh, that's so interesting. I would never would've thought to apply that lens. I typically would apply this lens to that kind of problem. I wonder if that applies here." And by saying, "I wonder," you make it about you, not them. And so that person can choose if that's an interesting thing to build on or not. This sounds by the way very non-rigorous feel like, "Ah, how can you possibly get rigorous thinking in the 'yes, and'?" It turns out there's limited amounts of time and so people will choose to build on the things they find most interesting. This is interesting things are surprising and potentially valuable. And so if lots of different people in the group are building on the same idea, that's a good sign there is something very interesting going on. **Alex Komoroske** (00:50:35): The third thing you do is you dribble in new perspectives. Every one to three a week, if you put in lots of new perspectives, once the norms can all scramble, if you have one in five people who all have a very particular kind of personality can mess up the norms, and so you're trying to minimize the chance you add a jerk. It takes one person to poop a party and go, "What are we even doing here?" You want to minimize the chance that happens. But second or thirdly and more importantly, you want to have as people with as different perspective as possible added into the group. And so this is what Ken Stanley might call, for example, novelty search. You're novelty-searching through the different perspectives in the overall thing. **Alex Komoroske** (00:51:10): When you do this properly, you get something magical. You get a group that people find intrinsically valuable for its own sake and just enjoy participating in and find meaning in, that also stochastically spins off changing insights for the surrounding context because you're searching through these ideas in a low stakes environment where the ideas that lots people build on, they go, "Oh, you should write that down." And this is like an idea lab, what everyone will call an idea lab. And this creates amazingly interesting insights. You just can't force it to do anything. It has to be a bottom-up and emergent, which means if you try to steer it towards an outcome, it won't go. But if you do these, they are amazing places to riff and to share ideas and half-formed ideas. And this is anywhere I go, I terraform the culture around me and create these, because I need it as a place to experiment and try out different half-formed ideas and build on them and be inspired by other people. **Alex Komoroske** (00:52:03): And that is one of my secrets, strategy secrets that I've been doing now for probably 10 years ago is when the first one started. And there's now I can count eight or nine of I've started over the years. Some of them emerged. So many of them are still at Google. And I think it's like they're just wondrous environments that I think create a lot of value. **Lenny Rachitsky** (00:52:21): And I love it's a perfect example of your approach of emergent properties, letting things emerge versus a top-down, "Here's what we're doing and here's what we're talking about here." If someone wanted to set this up within their company or within friends, any advice? What are some constraints and ways of setting it up for success? **Alex Komoroske** (00:52:37): Communities are all about momentum. You want to have a space too small, a time too short. If you have a big cabinet space of a lot of people in it and no one's talking, people go, "I guess this is the place where we don't talk," for whatever reason. So what you're doing is you want the smallest seed of people that you know are going to be actively engaged. So maybe there's four of you that already talk over lunch and you talk about whatever topic and it's always really interesting and generative. Cool, get that group together and do a thing. And then incrementally add people who you think are going to like that already as it currently exists. And then you need to feed it so you want to make sure that it never dies. **Alex Komoroske** (00:53:09): And a community with no people talking is definitely dead. A community with one person talking is already dead. You don't realize it yet. And so you're trying to maximize the chance that there's an interesting conversation even when you as the facilitator are not there. This takes some active policing by the... Like a garden has a gardener, there's somebody pruning back and saying, "Hey Jeff, just so you know, I think that came out a little bit strong to Sarah's idea and maybe next time add 'I wonder' to the front of that statement," or whatever. **Alex Komoroske** (00:53:35): The other thing that you do is when people reach out to you and ping you, they go, "Hey, let's think about this thing," and you go, "That's a really interesting idea. You should share that in the group." And then they do. And then you engage in the group and say, "That was really interesting," little emoji response. And people who didn't watch the interaction assume that Sarah just decided proactively to stick her neck out and share that and that it worked. And so this becomes a self-sustaining norm in the community. And it's not a secret. It's not if someone asks, "Yeah, I told Sarah to share that," but people watching don't realize that. And so it becomes a place that people do take risks and feel comfortable sharing. **Alex Komoroske** (00:54:07): The other thing you do is once a week or so, you want to make sure that you never propose something in the group that people go, "Eh." You always want to do a thing people go, "Yeah." So what you do is you see that if you're talking to other people, you say, "I wonder if we should have a live conversation every so often, right?" The chats were so fun, but it goes, "Would you come if I did one?" "Oh yeah, I would." "Okay, great." So now I say, "Hey, a few of us are talking. We're just going to do an experiment. We're going to have an hour-long conversation over lunch on Wednesday. Anyone in the group is free to come." **Alex Komoroske** (00:54:33): And then what you do is you make sure it always has quorum because if it doesn't have quorum, then the thing, it looks like the community's dead. And then what you do is you send FOMO stuff afterwards. So you say, "Here's my notes from the thing," or, "Thanks Sarah, Jeff," blah, blah, blah, blah, "or an amazing conversation. I thought the insight about," blah blah blah, "was so ridiculously amazing." So you want people who were in the group who didn't come to feel like they missed out and to come to the next one. **Alex Komoroske** (00:54:57): And so you're constantly creating these kinds of vibes to how to do it. You can't do it if you don't have somebody with a lot of energy. I'm typically the seed crystal for a lot of the groups I'm in to start them off because I have a lot of energy, and I like, anything that people have to say that I think is open-minded or interesting, I like building on and "yes, and"-ing and that kind of gives the foundation that it can grow. But look for the people who already roughly want it. Don't try to convince somebody who doesn't want it to want it. They will not. They will ruin the whole thing. **Lenny Rachitsky** (00:55:30): I just love this playbook for starting to build a little bit of community within a company. Have you written about this by the way? And if not, you should write a whole post about this. **Alex Komoroske** (00:55:37): I have. It's a long essay and it's just not, you can see it in Bits and Bobs. If you gave the Bits and Bobs to Claude and said, "Please write a thing about nerd clubs and essay and the style," it would do it because there's a lot of the pieces are in there, it's just not factored out. **Lenny Rachitsky** (00:55:52): I see you writing something down right now, which tells me you just articulated something in a new way that you want to say. **Alex Komoroske** (00:55:52): Yeah, that's right. That's right. **Lenny Rachitsky** (00:55:59): You mentioned this idea of constraints of time, and it reminds me of something that you shared in one of your Bits and Bobs around productivity. You say that if you have two hours to do a five-minute task, the effort to do that is impossible and instead you should flip that. Can you talk about this insight and how to be a little more productive? **Alex Komoroske** (00:56:15): Yeah, I think a lot of the trick to productivity is to play yourself like a fiddle and figure out how you work and what gives you energy and set up your day to structure it that way. So I find every time you start a task, there's an activation energy, especially a task you don't really want to do. And then when you complete it, there's a boop. There's a little burst of energy. So if you do this properly, you can get small things that are extremely easy to knock out in 10 seconds of effort, and then you do one that takes 30 seconds of effort, and then you do one that takes a longer bit of effort. But if you give it too much space, it's harder to do. So you almost want to find, "Okay, listen, I got 10 minutes. I got to do this thing where I figure out how to add, do this thing in gusto that I've been putting off. Ten minutes should be enough time to do it and structure it. So okay, right now is the only time I have to do this, to do it." **Alex Komoroske** (00:57:01): And another trick is I use one of my original media messages actually, one of the original public ones is about always rules are better than sometimes rules for self-control. And so if you're going to diet, "I'm going to skip lunch every day." Like holy, you haven't full thought on that at some point like a day with a big executive review, "I really need to make sure I'm well-fed before I go into this review," or something. And now you've broken the streak and now it's over. Whereas if you say a thing you know can do, "I will not have a dessert unless it would be socially awkward for me to not eat it. For example, in a small environment where somebody made homemade dessert and all of us are eating it, I'm going to..." So very clear black and white rule that you can hold on forever. **Alex Komoroske** (00:57:50): So for example, since the pandemic started, I've done a Peloton workout every single day since the pandemic started. **Lenny Rachitsky** (00:57:56): Wow. **Alex Komoroske** (00:57:56): And now once I do start going back into the office, if I had to commute into the office, I would sometimes do a meditation to check the box for that. But if I'm not commuting and I'm not deathly sick, I've done a full workout since then. And the idea each day of is today the day of all the hundreds of days in this streak that is the worst or the hardest for me to do this thing? Is this the day? No, of course it's not. I will do it. And so that keeps you in this streak that makes it harder and harder to get out of it. And in some ways, of course you can torture yourself in an unproductive way like at a certain point maybe you should stop that streak, but I think those kinds of structuring help you get the things done you want to get done. **Lenny Rachitsky** (00:58:38): It's like the Seinfeld trick of productivity where you just keep track of how many days in where you've done something essentially. **Alex Komoroske** (00:58:45): Yeah, exactly. And I think people don't give those kinds of tactics enough credit because there's lots of little social tricks to yourself and others. This is when you have other people who are depending on you for something and will know that you didn't do the thing, that were so much better. So just little tricks like this help you be wildly more productive. **Lenny Rachitsky** (00:59:02): Actually, I want to go back a little bit. I'm curious what you wrote down when we were chatting earlier that you thought was a good articulation if you're able to share, if it's interesting, **Alex Komoroske** (00:59:11): I wrote down, and the reason I wrote it down is I've never... And by the way, I collect everything even once I think are maybe onto something. So I wrote down, "A community with zero people speaking is dead and a community with one person speaking doesn't yet realize it's dead," is what I wrote down. **Lenny Rachitsky** (00:59:24): So fun. I love this practice that you have. **Alex Komoroske** (00:59:28): By the way, the reason I can do it, I can type insanely quickly. And in undergrad, I wrote my thesis on the emergent power dynamics in Wikipedia's user community and I did 150 hours of interviews with different editors in Wikipedia, and I transcribed them myself. And so I got really, really, really good at I can just pipe an idea straight into my fingertips and still listen to other stuff. So that's another superpower is I've just constantly, I'm able to capture it very, very quickly. I've written notes that are at least good enough for me to clean up within the next day or two into something that's more stable. **Lenny Rachitsky** (01:00:04): Is there a way you built this other than... Was it just you did it and you had to do it and you just figured out how to move fast? **Alex Komoroske** (01:00:08): I just realized later that I could type really good, really fast. I could just pipe it straight through to my fingers and it worked. And, I don't know, I don't know if I hadn't written my thesis, would I have discovered that? I don't know. **Lenny Rachitsky** (01:00:22): I feel like everything you do is on super speed, the way you think, the write and get stuff done. There's a lot. **Alex Komoroske** (01:00:30): I just realized when- **Lenny Rachitsky** (01:00:31): ... a lot of compute. **Alex Komoroske** (01:00:32): ... when you're feeling productive, you're unstoppable. And so just how can you be in your flow state as much as possible? And there's things that absolutely completely grind me to a halt, and I just make sure I invest my time in situations that don't have that characteristic. So when I work on something that I believe could work and have a big impact, I can't stop. Sometimes I'll wake up at 4:00 in the morning as I'm typically an early riser and I'm just like, "I'll write this thing." The meeting starts at 7:00 and I just think there's an idea that's really cool here and I let myself lean into those kinds of when I have the moment. **Alex Komoroske** (01:01:05): I also find that often if I have an idea and I just have itching to write it down, if I can write down 30 minutes and get a very rough of it in one place, now it's easier to clean it up later. But that first act of creation, I do it whenever the muse hits because it's 10 million times if it's like, "Oh, write that idea down later," you keep on delaying it, delaying it, now it's a month later. "What was the idea? How did that work again?" It's gone. And so I just try to capture the interesting insights. It's like a butterfly collector. The butterflies are going by, I try to collect them and put them in my collection as quickly as possible. **Lenny Rachitsky** (01:01:38): Or garden as one might describe it. **Alex Komoroske** (01:01:40): Yeah. **Lenny Rachitsky** (01:01:43): This touches on a quote I wanted to talk to you about. I think you described it as your life philosophy. "Do things that give you energy that you are proud of." Talk about that. **Alex Komoroske** (01:01:54): So to me, it's the combination of when you're doing something you believe in and that gives you energy, you are 10 times more productive. And you also, the effort that you are doing is its own reward. And so you are indefatigable on that topic and you go for much longer. So finding the substance of things that align with you that give you energy, then just it's like infinite energy. It's like they give an opportunity cost because it energizes you more than the opportunity cost of the time to go spend to other things. **Alex Komoroske** (01:02:21): And two, there are ways to give yourself energy, like for example, playing a video game, or there's any kind of mind-altering substance that might give you that like, "This gives me energy." Those are not things that I'm not saying do those. I'm saying what are the things that you'll look back and say, "I'm glad I did that. I'm proud that I did that." And if you take the perspective of a 10 years on looking back on each decision and thing that you're doing, and imagine seeing this decision played in front of 1,000 people whose opinion you care about, your family, your friends, your role models, would you be proud is a good sign of life that you're taking a broad enough perspective. **Alex Komoroske** (01:02:55): When you're busy and in the moment, it's so easy to say, "I just got to do this one thing that's probably not great to get this thing done. And once I do it, it's going to suck. But once I do it, it'll be fine." And then you find yourself doing it again and again and again and again and before you know it, you've lost who you want to be and you're now a husk of yourself. And so I think those two pieces lean into where you find energy, where you specifically find energy, your superpower, the thing that you intrinsically enjoy doing, and just make sure it's something that you are actively proud of and that helped make sure you don't take a bunch of shortcuts. **Lenny Rachitsky** (01:03:29): Along those same lines, I think a lot of people have heard a version of this quote, which is, "New things that give you energy." So one, I love the additional piece of it is, "and that you're proud of." Two, you have another quote that I love that makes you think deeply about stuff, which is, "The secrets of life is things you've heard a million times already, you just weren't ready to hear them." Talk about that insight. **Alex Komoroske** (01:03:53): So this I call the Hallmark card fallacy, which is you discover at great effort some deep insight that resonates with you and makes you see the world differently, and you want to share it. Insights are naturally viral. You want to share them and you go tell someone, it's like, "Guys, guys, the point of life is the friends we made along the way." And people go, "That's from a Hallmark card, man." And to you, it is you now possess the knowledge, the emotional intelligence to understand why that phrase has been shared so many times. Before, you heard it when you weren't ready and now it becomes a trite, "Duh, everyone says that. That can't possibly be a meaningful statement." **Alex Komoroske** (01:04:30): The reason people keep on saying it is because it's meaningful. And so I think that having that space of recognizing it, that when you have these epiphanies that come from different leaps in vertical development or the ability to, when you stare into the abyss and make it through the other side, you realize and learn a bunch of amazing things that you want to pass on others, and it's just really hard to get them to find it. **Alex Komoroske** (01:04:53): I find that that's one of the reasons I try to write things that are or share ideas that are like little seeds that you can shoot into someone's brain even if the soil's not ready for it, it's rocky or craggy, at some point in the future, if something goes through there and opens up a crack, that's sitting there to grow into an idea. One of the things that makes me the happiest is when someone I've mentored years and the years in the past, they go search me out years later and say, "Alex, I just want to let you know, you probably don't even remember talking to me, but that Tuesday at the building, the no-name cafe or whatever, on Google campus, you said something I was frustrated to hear in the moment I didn't understand it. And I just want to tell you, thank you because I finally understand what you were trying to tell me. And I realized that that influenced me in the decisions." That to me is one of those meaningful things I can hear. **Alex Komoroske** (01:05:41): And so I just find that you can't force it before people are ready to hear certain topics. **Lenny Rachitsky** (01:05:48): Man, that must feel so good to hear those sorts of closing the loop on something long ago. The point you make about cliches that you've heard a million times actually finally feeling right and profound, I had this very experience. I did a psychedelic trip with some friends a while ago, and at the end of it I was just like, "Man, love is all you need. Love is all you need." I felt that so deeply through the experience and I was telling people, they're like, "Shut up." **Alex Komoroske** (01:06:16): You telling, oh, do you just do psychedelics? Yeah, it's funny. **Lenny Rachitsky** (01:06:19): Yeah. **Alex Komoroske** (01:06:19): I have a lot of folks in my broader space who obviously have used it. So I never personally have myself, but I find there's various ways. The transcendent mindset is this feeling of being part of something much, much, much larger than yourself and losing your ego in this thing. There's different ways of doing it. Some people will find it in hiking and being out in the wilderness alone. Some people find it being at a concert and thousands of people perfectly in sync to this thing. Some people find it in religious experience. Some people find it using psychedelics and others to help get there. But a lot of it, it's that same just being willing to be in awe. **Alex Komoroske** (01:06:53): There's so many times that people feel the feeling of awe or wonder or curiosity is treated as a not very serious or childlike thing. And I just don't get that because that is how you are open to disconfirming evidence. It's how you see beyond the current limits of what you... Your ego gets hurt when you get disconfirming evidence. You don't want to hear it. And so you'll construct the world around yourself to not get that disconfirming evidence. But disconfirming evidence is what makes systems strong. It's what makes you strong. And so how do you put yourself in the situation to get that information and really receive it? **Alex Komoroske** (01:07:28): And part of it is just coming in terms of the fact of early in my career, someone called me kooky a bit. Oh, man. I must be embarrassed. I'm like, "Okay, fine. Yeah, I'm kooky, whatever." I'm totally at peace with the idea that some people track me as kooky and not particularly serious. I think people who watch the work that I do and the indirect impact it has realize that I'm doing something that is working even if they don't fully understand how it works. **Lenny Rachitsky** (01:07:53): To start to close our conversation, I want to throw out one more seed that might land with someone in the right time. You have this concept of the adjacent possible, which I think is a really powerful concept. And it's basically argues that a lot of people jump to big bold ideas, and instead the better approach is think about what's a constraint you have and lean into the constraints and use that as a guide. Can you just talk about this and how this might inform how people think about product and strategy? **Alex Komoroske** (01:08:20): Sure, yeah. The frame is the adjacent possible, which is I believe comes from design thinking. I've found it from designers in my life who are the ones who would just speak to it. And the adjacent possible is a set of actions that you do, that you can do. They are right in front of you that if you do them, they would work, almost certainly work. And in the tech industry in particular, we default assume that the adjacent possible is like this and then flying leap to something. And in reality, the adjacent possible is quite small. It's within arm's reach. And people will say, "Oh, you're being nihilist. You're limiting your potential. You're saying don't do big things." But when you recognize that your adjacent possible is relatively small, you realize that you actually have full agency to pick within the subset that is within your reach, and your actions matter because you take an action and now the world reconfigures and now you get a next set of actions and it's based partially on the action you just took. **Alex Komoroske** (01:09:11): And so if you slice this thing up and you have a coherent worldview and you have a principled approach, you can arc to wildly different outcomes than look like they were possible while at each point, each individual action is safe and reasonable. And so you can combine both of these things. I think so many times we try to jump and we jump to the end state of the thing. And actually you don't need to make that decision. If you can slice up your decisions into smaller and smaller decisions, I'm like, "This next step definitely makes sense." It will almost certainly pay for itself or the very least won't be too expensive. And then it might allow these other things to happen and you take it. And if those other things don't happen, okay, don't take another step on that path. That's fine. Go in other directions for a while. If it does, then take another step and another and another and another. **Alex Komoroske** (01:09:50): And this allows you to get rid of a lot of the risk and still be exposed to all the upside. And so the risk comes from trying to jump too far ahead in an unknown environment. **Lenny Rachitsky** (01:10:02): Is the general advice if someone's working on trying to figure out the roadmap, trying to think about what products to build is the advice, don't be scared to go a little incremental versus what people are always pushed, to do bigger. **Alex Komoroske** (01:10:13): You need both. So if you only do incremental, you will follow the shortest, the steepest gradient in front of you. So UXR says a user wants to do this and you'll do exactly that and you'll end up random walking through the thing. So you need coherence about where you're going and the way you get that is by creating a North Star for yourself. It should be in three to five years in the future, it should be very low resolution. It should describe a thing that every single person who reads it who has any kind of knowledge that might be useful or relevant agrees that it is plausible. If this happens, I would not say, "Well, a miracle happened." It'd say, "I could see how that could work." And lawyers say, "I could see how that could work." And someone who's worked on this 30 years ago at a similar product that Microsoft says, "I can see how that could work." **Alex Komoroske** (01:10:51): And that if you got to the end point, everyone would high five because if it's going to be a thing, they're like, "I guess that could work." At the end we'd be like, "Oh yeah, neat." That's not worth it. You want another story would be like, "Yeah, great. Wow, we kick off. We changed the way this entire industry works," or whatever. And now this is your North Star. North Star should update, but it's because it's far off in the distance. It will update. It will slide up across the sky a little bit. It won't be jerking around. You'll be arcing slightly differently. And then what you do is you look in your adjacent possible and you look for the thing that has the steepest gradient that pulls you towards your North Star. So you just want to go in that direction and you want to go in this direction. This one is second most in demand from what you think, but it's pulling you the direction that you believe will pull you there. Go in that one. **Alex Komoroske** (01:11:31): And then they keep on repeating. That's it. But you need both. Because if you only do incremental, then you'll end up random walking into a corner. And if you only do the long-term, you end up dreaming big and designing castles in the sky that are impossible to actually manifest. **Lenny Rachitsky** (01:11:45): To give you a metaphor from an experience I had, I did this silent meditation retreat once, and a big part of Buddhism is to not cling to a specific outcome and not have a plan in mind and be sad if it doesn't work out. And so I asked them just how do you achieve success and want to be successful while not doing that? And their metaphor is point your card in a specific direction that you want to go. Just point your card in that direction, essentially in your example of North Star, and just start walking. Don't figure out this is exactly the path I'm going to take to get to this end destination. **Alex Komoroske** (01:12:19): Yeah. And you'll know after the fact, you'll say, "Oh, I curved a little bit or I had this little jog than there." And you'll say, "Ah, it would've been more efficient." But we're so focused on efficiency of not wasting effort that we ended up doing nothing at all or doing very dangerous things that don't work. So I'm much sure that I have a path that's slightly inefficient because we're navigating unknowns and we couldn't know no point. I think I've seen the number of times I find where people say, "I need to know for this strategy," that someone was trying to get me to look at and then say, "is this number in five years, is it going to be 93 or 95?" And it's like, I don't know. And it doesn't matter either if it's going to be that order of magnitude. **Alex Komoroske** (01:12:56): It doesn't matter, and we don't have to do that analysis if we believe that the order of magnitude is of that thing. It'd actually be we had spent all the time to get the illusion of precision, which at great expense, and then it's the people say, "Oh, I'm data-driven. I want to really run the analysis to ground." There's tons of stuff you can't know ahead of time. So if you're getting a false precision at the beginner, that's a comfort blanket. That's just helping you feel like there isn't uncertainty. There's uncertainty everywhere all the time. And trying to ignore it by trying to pin it down with fake numbers that you just made up for yourself at great expense is a really bad idea. And that's why if the ideas are strong enough, things that have a compounding return don't give you, "Oh, we'll either get 93 or 95." It's like, "We'll either get zero or we'll get 1,000." Great. It doesn't really matter if it's 1,000 or 1,001, who cares? It orders a magnitude larger than the alternative, and so it is better. **Lenny Rachitsky** (01:13:48): That's really freeing. I noticed again, you were writing something. I'm again curious which you wrote down that you thought was insightful. **Alex Komoroske** (01:13:54): I actually this time I was not writing did something down. I was checking a thing I thought you might say that was going to reference was Tim Urban's, "Happiness is the reality minus expectations." I always get that backwards, but have you heard this frame, that happiness- **Lenny Rachitsky** (01:14:07): Let's get into it. Yeah, we're not going to get this. This is great. **Alex Komoroske** (01:14:09): "Happiness is reality minus expectations," and this is Tim Urban. It was from Wait But Why. And I think it's a very simple distillation of it, of if you set your expectations super high and it comes in and it's amazing, but it's below it, then it's a net negative. So the easiest thing, reality is hard to change. It's not impossible. It's hard to change. Your expectations are super easy. So just change your expectations. Hold it lightly and don't say, "Oh my gosh, this is going to be my kid's birthday. She's going to remember it. It's going to be the best birthday that she ever had and we're all it's going to be perfect." Because then when it doesn't go perfect and it starts raining that day, you're like, "Gosh." You get all worked up. Just say, "No, I want spend this day in a way that I can look back on and remember fondly." And that will include, yeah, it changed. **Alex Komoroske** (01:14:54): One other piece of advice someone gave me that I really like is try to feel the emotion about the story that'll make you feel in 10 years. So if it's funny in 10 years, try to see the humor in it now. And this one in particular was a friend, their newborn would, every time you changed her diaper, would poop. That was only... And when they did it, it would often be projectile. And so it was like a trap. You change the diaper. And it was like, what are you going to do in that situation? And then they're just like, "It's going to be a funny story in a few years, so let's see the humor in it now." Even though, God, I really wish this year- **Lenny Rachitsky** (01:15:28): That's funny. **Alex Komoroske** (01:15:29): ... you're not spraying poop on her. And I think that that kind of perspective is really, people sometimes hear this as, "Oh, you're saying don't dream big. Don't set high expectations. Don't expect more and be okay with mediocrity." That is not what I'm saying. I'm saying hold those expectations lightly. Allow them to change. Be willing to be convinced by different things, and seek something great. Seek something that you can be truly proud of and that feel very authentic to yourself if you achieved. **Lenny Rachitsky** (01:15:57): Alex, I feel like I could talk to you for hours. I can't believe it's already been almost an hour and a half. So just to wrap things up, is there anything else that you thought would be fun to share or maybe a piece of wisdom you want to leave listeners with before we get to a very exciting lightning round? **Alex Komoroske** (01:16:13): I think we covered it. I think we covered a lot of that. And again, we could go on for hours and hours and hours and hours. I could just do a random... I can feature The Compendium where I can pull up a random idea, and let's not do that. **Lenny Rachitsky** (01:16:24): Okay, amazing. Well, Alex, with that, we've reached the very exciting lightning round. Are you ready? **Alex Komoroske** (01:16:28): I am ready. **Lenny Rachitsky** (01:16:30): First question, what are two or three books you've recommended most to other people? **Alex Komoroske** (01:16:33): Origin of Wealth by Eric Beinhocker, which is great. It's about a complexity economics, why the traditional economic model doesn't work, and also why it takes an evolutionary lens on what kinds of business plans work and how companies execute them. That I found my entree into a lot of the systems thinking and I thought it was just absolutely brilliant. And the other one is The Elements of Thinking in Systems, which is short, easy to read, very approachable. In fact, if anything, people think of it as not serious enough because it's too easy to read. It's one of those books that when you read at the beginning you'll say, "This sounds right." And then later, years later, if you read it again you'll go, "Oh my God, that was so... I wasn't ready for that yet, but that is totally the way." So she's one of the people who talks about dancing the systems. Let go and dance with the system is one of her lines, and I think it's just a phenomenal book. **Lenny Rachitsky** (01:17:21): Next question. Do you have a favorite recent movie or TV show you really enjoyed? **Alex Komoroske** (01:17:24): For me, I was thinking about this, it's The Green Knight, which I watched I think a few years old. It's about the Arthurian legend. It's a challenging movie. In fact, when I watched it, I was like, "I dislike this. I do not find this interesting." And then I couldn't stop thinking about it and it helped me. I think this is one of the reasons I like to write in parable is a parable is open-ended. It encourages and requires the listener to engage into the idea and play with it and see how it affects them and how they affect it. And so for me, The Green Knight, again, I'm not excited to watch it again, but I found it to be the most impactful movie I've seen in the last couple of years in terms of amount of thinking that it caused me to do afterwards. **Lenny Rachitsky** (01:18:04): Wow, that says a lot. Next question, do you have a favorite product you've recently discovered that you really like? **Alex Komoroske** (01:18:10): To me, I think the answer for me is WebSim. It's the one that I like playing around with a lot. And I've said it before, I use Claude 20 times a day. I find that it's almost impossible for me to imagine doing work. I mean of course now I've got to use Strawberry and see how that feels, but yeah. **Lenny Rachitsky** (01:18:28): One use case of WebSim that I found really fun that I used with Dylan is if you do Gmail, if you give it gmail.com/someone's name, it just comes up with what their email looks like. And could do it for famous people, like for Patrick Allison or whoever, and it's like, "Wow, that's really good." **Alex Komoroske** (01:18:45): The elements are really good. One of the things we played around with is having a thing that generates fake data of arbitrary schemas, and I just write a short backstory of a person and then have it generate data that fits in this fictional user person's world. And it's just amazing the kinds of stuff, the coherence it has with, it's weird and it's very specific to that story, but elements are just so, they're like these little holograms of all this information of humanity is interesting informational package, this little thing. And all kinds, it's like a mirror that different things reflect back out of it at you. And it's shocking sometimes to see humanity reflected back at you. **Lenny Rachitsky** (01:19:29): It's like a zip file of all human knowledge. **Alex Komoroske** (01:19:31): Yeah, yeah. **Lenny Rachitsky** (01:19:32): Amazing. And it's because it's trained on all the things we've written, right? **Alex Komoroske** (01:19:35): Yep. **Lenny Rachitsky** (01:19:36): All right, two more questions. You have a favorite life motto that you often come back to find useful in work or in life? **Alex Komoroske** (01:19:43): I guess I've said too, this is cheating, but I said too, the do things that give you energy that you're proud of, and the happiness is reality minus expectations I think are really simple clarifying words to look like. **Lenny Rachitsky** (01:19:56): All right. Final question. You can go in one of two directions. One is what's something that you are going to add to this week's Bits and Bobs that you're thinking about right now that we haven't talked about? Or just go to your Compendium and pick a random thing and see what comes up and share. **Alex Komoroske** (01:20:11): Okay, so this is the... I'll just read this off. **Lenny Rachitsky** (01:20:14): Great. **Alex Komoroske** (01:20:16): This is written a year ago. **Alex Komoroske** (01:20:18): "We've forgotten a world without aggregators. Non-aggregator ecosystems make it so participants don't have to fear empowering their overlord, where that you have to worry about each bit of action you're doing, the aggregator is getting it more and more powerful. MySpace was the Wild West. Facebook made it so you can't change the CSS, which was better for users, containing some freedom. Aggregators make sense in the late stage of an era. At the beginning, they curtail too much exploration." **Alex Komoroske** (01:20:42): That's just my random reflections. I don't even remember what conversation that came from originally, but of the power of... I am just so obsessed with the idea that we are in the late stage of this current technical paradigm that we're in and so many things we feel like we figured them all out and nothing can be any different, and I don't love this outcome that we're in, the idea of you're... Just one quick framing. To me, if you ask somebody on the street to tell you what the canonical piece of software is, the answer they'll give you is something like Instagram, which is to say an app, which I think is a shame because an app is monolithic. It's one size fits all. It's not decomposable. It doesn't meaningfully interact with anything else in the broader ecosystem. And it's also only allowed to exist if some of the largest companies in the world say it may exist, which is insane to me. **Alex Komoroske** (01:21:26): To me, software is alchemy. It's the ability to extend human agency beyond ourselves to create something that can then combine with what others have created in unexpected and unforeseen ways to create this commentary of possibility of human agency. And somehow in the past decade, we've become convinced that all of this potential should be squeezed into about a dozen little boxes on your phone. And now with the power of AI, everyone just is default assuming that what's going to happen is we're all going to be locked inside of a box with a super God AI Clippy. And the only thing that people disagree about is which Clippy is it going to be? Whose Clippy is it going to be? **Alex Komoroske** (01:21:57): That to me is bonkers. I don't want that world at all. I want a world where we use this magical duct tape to escape the box, to allow software and humans using it to lean into their agency. And I think aggregators are amazing in an environment where you have a safe environment to have all kinds of interesting stuff that can't be fully open-ended because the aggregator can't allow it to escape the possibility of that ecosystem. And so for me, one of the reasons I'm excited about LLMs being a disruptive technology is I think that it allows us to get out of this monolithic sense of whatever. We're all just beholden to a decreasing number, very powerful organizations, and lean into everybody being able to be creative and collaborative and exercise their agency in a pro-social way. **Lenny Rachitsky** (01:22:41): Wow. Well, you blew our mind as a final element of this conversation. Alex, thank you so much for being here. Two final questions. Where can folks find you online? Where do they find stuff you're working on if they want to read more and follow the stuff you're thinking about? And then how can listeners be useful to you? **Alex Komoroske** (01:22:58): Komoroske.com is where. My husband gives me so much shit for it because it looks like it was designed in the early 2000s, which it was. I link to all the different posts there. If you click, there's a Google group, but now where you can subscribe to my updates whenever I post in the Bits and Bobs or any medium article, that's a good way of taking touch as I publish stuff. **Alex Komoroske** (01:23:16): And then the way that Google can be useful to me is I have office hours on my site that are open to anybody to join in. I am continually, they're booked off in a few weeks in advance, but if you find something that resonated with you or that didn't, or you think is interesting or, "Oh, here's a parallel. I don't know if you've thought of it before," just reach out to me. And I love, love, love talking to people, interesting people especially who have life experiences and backgrounds that are different from mine. At one point, a magician showed up in my office hours and described and said, "Hey, this tactic you're talking about in your Bits and Bobs, that's actually cold reading. That's what psychics use." And I would find all these crazy connections they'd never occurred to me before. And so people just reaching out and sharing ideas and I love. **Lenny Rachitsky** (01:23:59): Alex, you're awesome. This conversation was exactly what I was hoping it'd be. My brain is buzzing as I expected. Thank you so much for being here. I'm excited for folks to listen to this and to learn from you. **Alex Komoroske** (01:24:10): Thank you so much for having me. **Lenny Rachitsky** (01:24:12): Bye, everyone. **Lenny Rachitsky** (01:24:15): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [2/17] Becoming a conscious leader: Leading without fear, finding your life’s objective function, and getting better at vision and strategy | John Mark Nickels (Uber, Waymo, DoorDash) **John Mark Nickels** (00:00:00): Get clear on your objective function, and one way that I've gotten clear on it is trying to think about it from future me because five years from now, I'm not going to give a if I made the presentation slightly better, but I'm going to care a lot about what kind of relationship I have with my daughters, and that means that the next action, the next thing I do today and tomorrow, those will translate into the relationship with her, right? Not to be morbid, but just again, most of us just aren't really tuned into an awareness that our lives will come to an end. We try to pretend like we're going to live forever and just not think about it. And the horror of it is that we succeed, right? We mostly manage to just go live our life and eat ice cream and go to work and go on vacation and do what we do. To me, an awareness and mindfulness that our lives will come to an end punctuates reality in a way that requires me to rethink my priorities. **Lenny Rachitsky** (00:00:56): Today my guest is J.M. Nickels. J.M. has been a product leader at Waymo, DoorDash and Uber. He's also an engineering manager at Groupon, and before that an equity trader at Getco. At Uber, he built and launched the very first version of Uber Pool and then went on to lead the team responsible for the infrastructure and algorithms powering the economic and logistics brain behind Uber's matching and pricing systems. At DoorDash, he was head of product for DoorDash platform. At Waymo, he led product for the commercialization of autonomous ride hailing and last mile delivery. And he recently returned to Uber to lead product for the mobility team. **John Mark Nickels** (00:02:08): Thank you, Lenny. Thanks for having me. I'm thrilled to be here. Really appreciate your dedication to helping product managers improve their craft and up-level. We've done a lot of great researches out there for that, and coaching and development, as I'm sure we'll get into, is a passion of mine as well, so we have a lot of shared interests there. **Lenny Rachitsky** (00:02:26): Oh, I really appreciate that. I want to start with a phrase that came up again and again when I ask people what to talk to you about from your colleagues, and this phrase is conscious leadership. What is conscious leadership? What does this phrase mean? **John Mark Nickels** (00:02:42): To me, leadership is broadly defined as having influence in the world, and so by that definition, to me, everyone is a leader because we all have influence in some way. It's not about whether you're a manager or not, it's like I have influence on my kids or my partner or my community, or the world, the way I vote, the way I show up. So we all have influence. We're all co-creating influences of each other. So that's the leadership piece. The conscious piece then is becoming more aware, waking up. To me, it's like learning more about my interior world, what my background is, my biases. We all inherit certain belief systems from our parents or our church or our community, and a lot of times they kind of go unquestioned and then they end up in conflict. And so it's really just about becoming more aware and then taking responsibility for the influence that I have. So yeah, taking responsibility for my influence in the world. **Lenny Rachitsky** (00:03:42): As you talk about this, something that came up and something that I thought about as I was preparing for this episode is this idea of soft leadership, the power of soft skills and just how important that is in success. Is there something there that comes up when I say that? Just the power of soft skills and the importance of those in being successful. **John Mark Nickels** (00:03:59): Yeah, it's, what was it? Theodore Roosevelt, speak softly and carry a big stick? Yeah, I think I've evolved in that department. I think when I was younger in my career, I thought it was really important that we got to show up to the meeting and have the right slides and be the loudest, rightest voice in the room, and that's the way to have influence. And there's certainly a place for having leadership in a meeting and presenting a point of view and helping guide the narrative, but to me, yeah, I would say I've evolved more towards sitting back. It's also as I've become a more senior leader, I'm aware that there are power dynamics there. There's imbalances where junior folks don't feel as comfortable speaking up or I say something's not a good idea and then, "Well, I don't want to disagree with J.M." **John Mark Nickels** (00:04:45): So it's like, back to being more aware of my influence in the world. I really try to spend more time being mindful of that and say, I want to hear from other people first. I want to create space and I don't need to win the argument in the meeting. There can be a follow-up. It's not like this is my last chance to say something, but that's also more true when you're more senior because when you're more junior, it's like, well, this is the one presentation I have with Dara for the next six months. I really got to nail it. And so the pressure is a little bit different. Yeah. **Lenny Rachitsky** (00:05:14): **Speaker 3** (00:06:33): Pendo. **Lenny Rachitsky** (00:06:39): **John Mark Nickels** (00:07:55): Yeah, yeah, I mean, I would say I have been fortunate to experience probably three Ubers at this point. We joke about Uber 1.0, the Travis era, and you hear a lot about in the media the kind of bad parts of that, but there were some really good parts too. I mean, I think there was a lot of... Like when I joined in 2014, there was this mission of making transportation as reliable as running water for anyone anywhere, which is bold, audacious, and maybe a little bit pretentious from a little bit of Silicon Valley edge, but you could feel the electricity in the air. There was this energy and excitement like we're doing something transformational, autonomy is coming, car ownership will change. And it just like, feel, like my vibration. **John Mark Nickels** (00:08:37): And then, yeah, the good parts of that era were, Travis was a very great visionary product leader, and we started ATG and Elevate and these future-forward things and the way he would conduct product reviews, I learned a lot. It was stressful at the time, but looking back, I was like, wow, I learned a lot. But yeah, I would say it was not a very conscious leadership sort of place. You're right, it was like many organizations that run on fear because you can do that, carrots and sticks do work. But actually that's kind of how I found this work is it was in 2015 and I was a very junior product manager at that point, in over my head in a fast-growing place. And in these weekly reviews with Travis as we were building out Uber Pool, and I had a six-month-old daughter, my firstborn, and we had just moved to San Francisco from Chicago. So my whole life was in flux and it was a very stressful place, and I was like, "I think I'm going to snap. I don't think I can handle this." And that's kind of what led me to start to explore this sort of inner work and meditation and sort of finding a way out of that. And that's what got me interested in bringing it to teams too, is because I remember I was in one meeting where we were working on this future pricing thing, which is rider pricing, driver pricing, incentives, and how we bring surge pricing and all that together. And it gets very, I'll go heavy, and we have all these PhDs in the room, some of the best minds in the world. We were able to hire people like Garrett van Ryzin, who was the foremost [inaudible 00:10:04] more person from Columbia and other people. **John Mark Nickels** (00:10:06): But everyone's back to lizard brain, everyone's arguing. They're like, "Well, no, I think we should do it this way. We should do it this way." And I was like, huh. As much as I enjoy the content of this, believe me, I'm an algo PM end to end, I love that stuff. But I was like, I don't think this conversation actually needs another PhD, or I'm not even PhD, but content expert. It's like what we need here is a way to shift again, back out of that fear, threat, righteousness sort of state into a more co-creative, collaborative, open-minded, curious, trusting sort of space. And that got me interested in pursuing more skills in coaching of individuals and teams. **John Mark Nickels** (00:10:49): But yeah, to your Uber question, yeah, the Uber 1.0 was crazy. Uber 2.0 was kind of like, Travis is out, the board is feuding, is leaking to Mike Isaac, whatever. And then Dara comes in and the peacemaker and then tries to stabilize, but the IPO is rocky. And so now I would say we're in Uber 3.0, which it's full pirate ship to navy, in Reid Hoffman's words, a profitable company. We're printing free cashflow, we're in the S&P 500, we've established the independent contractor model in a lot of states and jurisdictions, and it's like there's less risk of that model changing. **John Mark Nickels** (00:11:28): And yeah, I would say we're in an era now of Cambrian explosion of different types of transportation. The company really just built the UberX model and scaled it out to the world. That's primarily how we got here. And now it's like we're going out for all these different new sort of modalities, whether it's reserving a ride in advance or shared rides or renting a car or buses, and then different supply types too. It's not just contracted, we have a lot of fleets in the platform, we now have a lot of taxi drivers in the platform. You've seen we've signed deals with Waymo and Cruise and other autonomist players. So I feel like we're now at the beginning of another era of Uber and transportation, that the next decade or two, it's going to be super exciting. **Lenny Rachitsky** (00:12:12): One quick tangent, UberX, a previous guest shared that the name UberX came from... it was just like the internal code name, UberX, we'll figure out a real name later, and then it stuck and no one had a better name. Is that true? **John Mark Nickels** (00:12:23): Yeah, that's right. I think that's right. **Lenny Rachitsky** (00:12:24): Amazing. **John Mark Nickels** (00:12:26): When I joined, we were already scaling UberX rapidly. I joined in early 2014. That's amazing. But I did help name Uber Pool, Uber Pool, which I selflessly like to bring back. It got renamed to Share during my external APM rotation. **Lenny Rachitsky** (00:12:42): Okay. I want to come back to the thread that I pushed us off of, which is you talked about, you made this really interesting point about emotions, and this is something I've been learning myself recently with having a kid and also a couple of previous guests. So you say that when you have... so you're in this meeting, you're stressed, there's a lizard brain kicking in. Something's like, "Oh, Dara's going to think I suck and it's going to really screw my career if I mess up this presentation." Your advice there is very counterintuitive, I think for a lot of people, which is accept that emotion. Because when I feel stressed and nervous in a meeting, I'm not, "Embrace the nervousness, let it out." It's more I'm just like, "No, it's fine. Going to be okay. Don't worry about it." Talk about why that is actually more effective. **John Mark Nickels** (00:13:28): Yeah, yeah. It's like my daughter the other day had some nightmares and she was like, "Dad, how do I stop thinking thoughts about the nightmare or whatever?" And I said, "You can't. Don't try to stop the thought. Just allow it. Let me show you why that doesn't work." I said, "Don't think of a pink elephant. What did you just think of?" And she's like, "A pink elephant." And then now she thinks it's hilarious and she tells her sister, "Don't think of a pink elephant." **John Mark Nickels** (00:13:55): But yeah, I think you're right. It is a little counterintuitive, but one of my first coaches actually had a great phrase, what you resist will persist and what you fear will appear. And so in my experience, this is another reason why becoming more aware of my internal world has been so important. I have more agency than I realized on the outcome of my experience. And so when I think a thought like, Dara might think I suck and then I have a thought that I suck, that can become a self-enforcing negative feedback loop where I have a thought that creates stress, anxiety, fear, and then that triggers more thoughts and we call it cognitive emotive loop where you're kind of in this cycle of thinking stressful thoughts and then having unpleasant, anxious, fearful feelings. And so one way to break that is to just allow it and not try to fight it with other thoughts. **Lenny Rachitsky** (00:14:50): So the advice is very tactically, so you're in a meeting with Dara, you're stressed about something. Just allow it, let it be. Don't try to pretend like it's not there or don't try to convince yourself- **John Mark Nickels** (00:15:00): Well, that would be the first step, is just to allow whatever's here, thoughts and emotions are rising. They come, they go, they're transient. It's not permanent. There's a lot of wisdom I think in the Buddhist lineage around those concepts. And then the next piece for me, once I can take a breath and relax a little bit, is coming home to the fact that I... and this is a little more radical for some people, I don't actually need Dara to approve of me in my presentation in order to be okay. What I'm up to over here is trying to force self-worth and self-love from within. And so we talk about approval, control and security. It's very easy to look for that from the world. Do you approve of me? And if not, can I control outcomes to get approval or get security and get the job, the bank account, the house, whatever it is? **John Mark Nickels** (00:15:52): But what I kind of woke up to at one point was that as long as I was going out there looking for all that stuff to try to complete something inside of me that was missing, it's like I was a hungry ghost. It's like, it doesn't matter how many Michelin star meals and promotions and money and title and whatever. It's like it's never enough. It's like you kind of enjoy it for a little bit and then you get back to like, hm, you know? So it's like a never ending sugar addiction. And so that's the next step for me is allow it. Yes, allow the emotion, allow the thought. Come home to, "I am okay even Dara does think I suck." And then also it's not permanent, right? It's like sure, there might be some high stakes things in life where you only get one shot, but for the most part it's like if I didn't do a great job on this presentation, there'll be another one. It's okay. **John Mark Nickels** (00:16:45): And think of it as practice. The other thing is from the fear threat state, I'm like, uh-oh, this is a risk, alarm bells, my career could be over. Whereas if I'm in that trusting, curious, open space, it's like this is an opportunity for feedback. How can I learn? How can I get to become a better presenter? It's like the feedback from others is no longer a threat. It's actually a gift. It's like information that I can use or not use to alter how I show up in the future and the skills I develop and all that good stuff. **Lenny Rachitsky** (00:17:21): I imagine some people may hear this and feel like if Dara or Travis or whoever thinks I suck, my career is at stake and that really matters and everything's going to fall apart in my life because I get fired, there's stakes involved with messing up. Is there anything that helps you get past that and not worry so much about just this trickle effect of all the things that could go wrong if you mess something up in an important high stakes meeting or presentation? **John Mark Nickels** (00:17:46): Yeah. Again, and maybe it is a little paradoxical, but what I found was the more I focused on how I show up and optics and having a good deck and all this, the less I got promoted and then the more I dropped focusing all that. Because for my first few years of Uber, I was a senior PM and then I finally got my groove and started kind of moving through the product ladder. And it was really correlated to me at least, maybe causal, with dropping a lot of the focus on the presentation and how I show up and whether people like this or not, and just really focusing on the work. It's like, you know what? I am here to be a conduit from what wants to happen in the world of transportation and mobility and shared rides is one that I've always been particularly passionate about, so that's a good example, and then how can I get present and listen to what wants to happen next in the world of shared rides? And there's lots of different ways we can take the product and all that. **John Mark Nickels** (00:18:45): And it's really about, I want to make a fucking awesome product, right? And it's like, whether people like me or think I'm a good PM or presenter, as long as I manifest a great product into the world that makes riders better off, drivers better off, cities better off, less congestion, all these things, that to me is the reward. And sure, in order to manifest that, it is often helpful to communicate things, present, align, all those sort of things. But those are a means to a more powerful and transformative end than just my career. I'm tapping into a larger purpose and sense of belonging and identity and sort of meaning. And from that place, it's like I've just dropped the kind of egoic, self-centered focus on whether I did good in the presentation or not. And then yeah, maybe paradoxically, by doing that, it actually goes better and we do great work and it gets recognized. **Lenny Rachitsky** (00:19:41): Wow, that is fascinating. To make that work, you need to really connect with the mission of the company you're working at. You really need to believe this is very important and very meaningful. So maybe that could be an issue for people if they don't really care about what the company's doing, it's going to be hard to allow for that approach. **John Mark Nickels** (00:19:58): Totally, totally. **Lenny Rachitsky** (00:20:00): It's interesting that you say that optics aren't as important. I think the reason I think about this as you talk about, a lot of people feel like there's the work and then there's talking about the work, making the work, the optics of what you did is really, really important. And I love to hear. Nobody wants to do that, but they always get this advice. So important, optics, how you share the impact you've done, how you represent yourself. I guess, is there anything else you can share there about just helping people relax about that aspect of their job and without being so critical? **John Mark Nickels** (00:20:31): Yeah. And to be clear, I do think it's important. It can't be all work and no optics or all optics and no work. There does need to be a balance there, and I think it does change depending on the size of the company and the level of seniority. When you're an IC, you're probably hopefully doing more actual work, and leaders are supporting them and presenting and communicating that work so that they get. **John Mark Nickels** (00:20:56): I mean, the optics does matter, right? At some senior level, you do spend more time on that, and it does have influence, back to the influence piece, which is like, how will I communicate an idea and the need for engineering resourcing and so forth might mean that team gets more engineers or doesn't get more engineers, or we do this project or we don't, right? Because at the end of the day, executive resource allocation is largely based on the, quote-unquote, "optics layer". So it does matter. I want to be clear. I'm not saying it doesn't matter, but to me, again, it's more about that's a means to an end. It's not about the optics itself. It's like say what the Buddha is saying, don't mistake the finger pointing at the moon for the moon. And the finger pointing at the moon could be the presentation, the OKR, you know, whatever. And it's like, that's not the actual outcome we care about. That's an input to the output that really matters, which is the work, the product. **Lenny Rachitsky** (00:21:47): Okay. I'm going to shift this to hard skills and another kind of direction. So another thing that came up a bunch when I was asking people what you're amazing at and what you're really good at is strategy and vision. I had this quote from one of your colleagues, Brent Goldman, "J.M. thinks big, has lots of great ideas, will 'yes, and' to other people's ideas, will inspire everyone around him to be more creative, ambitious, and hardworking. He doesn't climb hills, he finds bigger mountains and will bring you there." So along these lines, say someone comes to you and wants to build these skills, wants to get better at strategy, wants to get better at vision, which is something basically every product leader is trying to get better at and every leader wants to get better at, what advice do you generally share? How does one improve in these areas? **John Mark Nickels** (00:22:35): Yeah, thank you. I appreciate the compliment. Thank you, Brent. That is a great quote. Wow. Yeah, I mean there's no magic toolkit or manual. I've long ago given up on the notion that I'm one book away from the perfect elusive answer to whatever plagues you in life. And there's obviously lots of books about strategy and you get into all that. I guess for me, a couple of things have been helpful. One is you mentioned earlier finding a mission that you're really passionate about. I think it would be hard for me to come up with a strategy for improving the healthcare system. It's like, sure, it's important. I hope someone does it and figures out how to deal with HIPAA and whatever, all this stuff, but it's just not for me. It's not my purpose, mission and vision in life. **John Mark Nickels** (00:23:24): And so step one is, am I working at a place and in a product area in which I have a tremendous amount of passion? Because for me, that is the fuel and the motivation that helps me break through to getting the strategy. That's the first step. So that's where I feel enormously lucky because again, this revolutionizing transportation and car ownership and what happens with autonomy and form factors and future of cities is something that I'm super excited about. I think about my daughters growing up and having a different world to live in that's safer and more environmentally friendly, all this stuff, and I get really jazzed when I think about, wow, the work I do could actually impact their future lives and other people. It's like, whoa, I can feel the chills right now. It's just super motivating. So that's the first place, just getting myself fired up. **John Mark Nickels** (00:24:10): And then the next thing I guess that's been helpful is I've deeply immersed myself. I haven't really jumped around between crypto and gen AI, this stuff, and a lot of people do that. It's great, nothing wrong with that, but I've been in this largely focused on mobility space for 10 years now with some stints over in the restaurant tech and delivery side, but very related in terms of last mile logistics. And so I think it's hard to come up with a great strategy if you've only been working in an area for six months. Especially things like this, they're super nuanced. Shared rides is another a good example where it's a super hard problem to crack and it's going deep on that for a long time is a precursor to being successful. **John Mark Nickels** (00:24:55): The other thing I would say though is people always talk about first principles thinking, but if there's truth in it, I think that's like when Elon's like, "Well, why does the rocket cost a gazillion dollars to launch? And there's no reason they have to throw away the materials and blah, blah, blah." One example might be, why do we need a 4,000 pound vehicle to move a human three miles? Okay, well... Or even a couple of humans. We do an Uber Pool or a Share, and you move two humans or three humans, even then that's pretty inefficient. If you think about just the physics there, the energy expenditure. **John Mark Nickels** (00:25:32): And that's where I think you might come up with bikes and scooters and little other things. And sure it's not always, it's raining or you want the car, but that's sort of an example of why questioning why are things the way they are, and then is the way they are super inefficient or not optimal in some sense? And that is often a doorway to opportunity to see, okay, well maybe things could be different. And so I kind of extend that at a larger level to the future. My general thing is just like, yeah, that's the mountain thing is I try to just close my eyes and imagine the future as far out as I can. **John Mark Nickels** (00:26:09): It's like five years from now, 10 years from now, whatever. And it's develop a really salient picture of what that looks like. It's like, we could do this right now, it's okay. 10 years from now, what could San Francisco look like? Or some city? What happens to the parking spaces? Are there still parking garages? Are those parks now? What are the modes of transport? Are there bus-like things that are autonomous that are connecting people to bikes and scooters? And how are people living? Do they live in the far suburbs even more because autonomy and they have a nicer house and they come in, or is all the space repurposed and actually it's cheaper to live in the city because we compact things, blah, blah, blah. It's not even about having the right one, it's more just developing some sort of picture of the future that gets you fired up. **John Mark Nickels** (00:26:57): And then yeah, you got to go articulate that and communicate it and get people to come on the journey with you. But from that picture, it's like, well, first principle, what's going to be true 10, 20 years from now? Well, autonomy is a given. I think most people would probably agree with that, and we'll probably solve it with just cameras and won't need lidar because humans don't have lidar. The cost of vehicles and sensors will come down, remote support will come down, and at some point it'll be super cheap and it's like, okay, I can extrapolate, that will be a thing. Separate from which player wins. I'm not saying I can predict the ecosystem of companies that will win here. It's more about just the underlying dynamics. And then that would be one, and another one would be sharing. It's like, well, a lot of people are like, "Oh, well, once we have cheap autonomous cars, everyone can just have their own super cheap Uber, Tesla or whatever it is here in the city." **John Mark Nickels** (00:27:45): And you're like, "Well, that doesn't work because then we're going to hit this induced demand concept," which is what economists call it, and you used to, when text messages cost 50 cents a piece, how many did you send versus now when it's free, it's in the millions. Same thing when they add a lane to a highway, the traffic just gets just as bad as before because more people drive and so forth. So if we flood the streets with super cheap autonomous cars with single occupancy, we're just going to have even more good luck than we do right now. Maybe we'll do The Boring Company thing and dig tunnels, but that seems unlikely. **John Mark Nickels** (00:28:16): So then for me, it's like, well, from first principles, shared rides is going to continue to be an important part of the future of transportation. And other modalities where yeah, back to the three mile thing, it's like, well, there probably will be various form factors of bikes, scooters and little mini golf cart things and whatever we end up building. And so that's hopefully an example of how I try to think about what are the likely things to be true in the future, and then how does that lead to a potential ecosystem and strategy around what we might build towards that future. **Lenny Rachitsky** (00:28:50): This is great because this is something everyone can do, and there's all this talk of creating a vision, painting a vision, communicating a vision, and what you're describing is how to actually sit there and think about what it might look like. Sit there, close your eyes and in your head visualize in the next five or 10 years, what does the future actually look like? And do you do this in a state of if we were to do this product and change, or is it just even if we're not around, here's where the future is going to go most likely, which direction do you usually take? **John Mark Nickels** (00:29:20): Yeah, that's a good question. I think you could probably do either. I typically like to start with the former, which is just like, what will the world move towards absent of me? Just trying to pick a bird's-eye view of what I think the trajectories are and trends and what's going to happen. And then yeah, you could apply a lens of, okay, if we were to build product XYZ or have the strategy, how might we influence the outcome or benefit from it, or is it in congruence with that or is it rubbing against that and trying to change that? Either could be good, you might say it's a tailwind or a headwind, both are overcomeable, but having some awareness of the relationship between those things is good. **Lenny Rachitsky** (00:30:00): And I think transportation, Uber, Waymo, in theory it might be easier to visualize that future and how exciting that might be versus a B2B SaaS payroll app or some photo sharing thing. But on the other hand, not necessarily, right? What in the future in 10 years, how are people going to be paid? How do people work at companies? I think there's an opportunity to do that no matter what you're building. Is this something you actually do? You just sit there in the office, close your eyes and just imagine? Is this more of an iterative process where you get with your team, how do you actually practice this? **John Mark Nickels** (00:30:31): Yeah, it's not like something you can just schedule 30 minutes for in the middle of your day of packed OKR reviews and random one-on-ones and meetings. It's like, I like to do it on my own at first unless it's something that I already have an outline for and I'm ready to move into a team space. So for me, it's like, yeah, can I get into a quiet contemplative space? So yeah, I like to go for a run and that obviously gives me ideas, or I'll go for a hike up in Marin and sometimes I'll just think of stuff or jot something down or make a voice note while I'm doing that to get things going. But yeah, the first step for me is just getting out of the craziness of day-to-day. To me, it's still insane how many product manager, leaders of all kinds just run the schedule of back to back meetings, 30-minute review, big meaty topics, you run out of time, run to the next thing, answer a bunch of emails, and then cram some PRDs in there. It's like, it doesn't work. **John Mark Nickels** (00:31:27): And so I'm a big fan of carving out time, again, first for myself, a couple hours, whatever, where I can just get out of the day-to-day craziness and get into that head space of five, 10 years from now. It's just a different place. So you need to transition to that. And then bring that to teams. If I have an outline of that kind of future of transportation in my head, I might share that with a group of folks and we'll come together also for some extended period of time. We recently had an all-day Monday thing where eight of us came into the office to talk about future of marketplace, and it was super productive. It was like, laptops down, we're going to spend all day together on a whiteboard. It's like a lost art. People don't use the whiteboards anymore. But yeah, and then from there it's getting more people and then you can kind of iterate on it. It's like I had some vision of the future and someone points out something that is a little bit off with it or has a better idea. Then you move into co-creation. But I love that. It's like Pixar calls the brain trust. If you read [inaudible 00:32:28] book, how they come up with a Toy Story and Inside Out and all these things, is they have this group of people that just sits around riffing on ideas. And again, there's no judgment, there's no attachment to being right. They're in a co-creative sort of space where they're just like co-exploring and riffing with each other. And I love to be in that space with other PMs and engineers and data scientists. **Lenny Rachitsky** (00:32:52): **John Mark Nickels** (00:34:13): Well, it's not really good for your podcast business to tell people not to listen to podcasts. **Lenny Rachitsky** (00:34:16): Okay, everyone, we're cutting this. What I find really helpful is playing Lenny's podcast every time I'm out and about. **John Mark Nickels** (00:34:25): No, but there's something to what you said, which is there's always a lot of content out there to pursue, and I've been in that mode where I'm like, yeah, more content, more... But yeah, actually similar to you, spend a lot of time now not listening to anything. Go on a hike where you don't listen to a podcast or music on your commute and see what happens. You might be surprised. **Lenny Rachitsky** (00:34:45): Yeah. And it always ends up being like, oh, that was cool. And that's where shower ideas come from and all these things. Maybe just to see if there's something here, in this meeting that you have, this ideation brainstorming meeting, is there anything that came out of that that was really surprising or new from a recent experience? Is there anything there of just like, oh wow, we really uncovered this potential wrinkle of the future that we really need to think about differently? **John Mark Nickels** (00:35:08): Well, it wasn't maybe a specific wrinkle, but one of the things that we're thinking a lot about, like I'm fortunate to be involved in trying to help develop and articulate a multi-year three-year product or even overall tech strategy for the mobility business at Uber. And one of the, I guess big ahas for us is as we move away from the, in some ways simpler world of UberX being the predominant product, which is it used to be pretty simple. It's kind of like a taxi meter on the driver's side. There's a time and distance rate that everybody gets, and then on the rider's side it's like, sure, there's some surge pricing based on supply and demand, but it's one product, it's pretty straightforward. And so this future of multi-modality and on the both demand side and the supply side is what makes the marketplace even more complex and challenging to build. **John Mark Nickels** (00:36:00): And so it was kind of all this around, okay, well now that we have taxis in the platform and we have fleet providers and we're starting to add Waymos and Cruise and other things, we have to have a marketplace that's aware of those different types of supply and which one might be available for what trips and how to think about cost and quality and allocation of trips and all that. And then on the demand side, it's like, yeah, we've got all these different products like shared rides and reserved rides and comfort and X and priority, and it's like how do we think about how to price those relative to each other? How do we think about which one's to show which user? How do you think about the ranking and so forth? And then that all has feedback loops into the pricing and matching itself as well. **John Mark Nickels** (00:36:45): So the dynamics of the thing, when I think about the future of marketplace, Uber, is like, whoa. And I don't think anyone's ever built that. That's the super cool thing about it. I think we have the best logistics marketplace tech on the planet and we built something that no one else has ever built, relative to digital marketplaces, for example, just different physical world requirements. And then this next arc of what I described of thinking about different types of supply and different kind of demand channels just adds even more complexity to that. But the aha was like, I guess, yeah, we got to think about all that stuff and think about how the supply and demand relate to each other and yeah, it's going to be cool. **Lenny Rachitsky** (00:37:26): It's just an infinitely cited marketplace now. That's wild. One last nugget I wanted to just reinforce that you shared about how to become better at strategy and vision, developing great and interesting and innovative strategy, and vision is going really deep on a topic. So you've been in the space for a long time. There's this idea that Paul Graham talks about, I think, called your top idea or something like that, that when you have... Whatever your top ideas, the more you can just think about that and keep that top of mind as you go about your day and just have one core focus, the more likely it is you're going to come up with new interesting ideas because your brain's going to keep working on it when you're driving around listening to Lenny's podcast. Just kidding, or going on hike. **Lenny Rachitsky** (00:38:09): So I think that's a really important point is if you're finding you're not coming up with a great strategy or vision and just having struggles, part of it might just be you're not spending enough time in that space, you're not going deep enough in the problem area. One approach is just spend a decade in that space. Is there anything else just comes up as I say that of just how to do that? **John Mark Nickels** (00:38:26): Yeah. Well there's also, that's at the macro level, maybe spending 10 years in a space, but at the micro level, back to kind of like defrag your day, don't just do the 20, 30 minute meetings on 20 different topics. Sure, sometimes you do that first and you got to do that. You have a large team like I do, obviously reviews across teams. I'm not saying I don't do that on some days, but it's like, yeah, what are my top few things, right? I think, you're right, I think it was Peter [inaudible 00:38:52] or PayPal guys talked about that too, going really deep and having a person or a leader really responsible for one core, deep thing for the company, and that's something they immerse themselves in. And so in the micro, that to me again translates to, yeah, I don't have a to-do list of 20 things. I try to have a to-do list of three of the most important highest leverage things that could have impact broadly across the company and then try this, like you said, let that one top thing marinate and chew on it. **Lenny Rachitsky** (00:39:22): I love that. And I recently had a post about all these productivity tricks, and one of the things that I find really helpful is at the beginning of each day and also at the beginning of each week, just write down, here's the one to three things that I need to do and get done. And everything else, I might have this really long list, but here's the three things if I get done, life will be good. I've done a lot. I've accomplished really great, important things. **John Mark Nickels** (00:39:42): Totally. I tried to do the David Allen GTD thing once, the super complicated organization system. It was too much structure for me. I couldn't do it. At the end of the day, what you said is right. There's basically three things that I need to do next, and then there's just some random backlog that I can just scan through periodically and that's it. That gets you most of the way. **Lenny Rachitsky** (00:40:01): It's crazy. I read that book 20 years ago at this point, and there's elements that still make things, like I leverage and benefit from. Even if you don't do the whole thing, that book I recommend people read because there's just like, if you pick a couple things from there, your life gets better. The things that have stuck with me, the main one is this waiting for concept of if you're waiting, if you email your designer and like, "Hey, I need you to review this product," just note, "Waiting for Dan to review design." And just having that thread written down and not in your head really helped me. **John Mark Nickels** (00:40:36): Totally. **Lenny Rachitsky** (00:40:36): Yeah. Anyway, I'm not going to go on that tangent. **John Mark Nickels** (00:40:41): Yeah. It's the core concept of like, whatever steps you use. I think the most powerful takeaway from that book for me was if it's in your head, you're screwed because it's like you're trying to keep track of stuff and be creative and come up with the future of transportation and remember to pick up something from the pharmacy. It's a recipe for disaster. This whole idea of empty mind, beginner's mind, well, you have to empty the mind of all the to-dos first. Just get that out of the head. **Lenny Rachitsky** (00:41:04): Absolutely. I think it was mind like water, that's the one that stuck with me, where nothing you need to remember can be in your head. It needs to be written down somewhere Anyway, let's not go into a whole productivity podcast here. **John Mark Nickels** (00:41:15): Perfect. **Lenny Rachitsky** (00:41:17): So we talked about vision strategy. So there's classically two problems people have with vision strategy. One is how do I get better at it? The other is just like, I need to actually get shit done. I can't spend all my time thinking about vision. You have a really good take on how to find this balance and you've seen it work well and not well, just vision versus execution. When do I go big vision, how much I spend on vision versus just get shit done, execute, execute, execute? What could you share about just what you've learned about how to find that balance and what you've seen work and not work? **John Mark Nickels** (00:41:48): Yeah, I think you can go too far either direction, right? It's like everything in life is about balancing the polarity between two opposing forces. And so in this one it's like, yeah, you go too hard in division and theory land, I've seen that go off the axle, early Uber where again, back to the future of pricing, it's like we have all the data scientists and PhDs locked in a room for two weeks and there's a beautiful whiteboard diagram. What did it look like? And then it's like, why don't we actually build this thing? And engineers are like, this is like boiling the ocean. And you just get wrapped around the axle of like, well, that sounds really good in theory, but I have no idea how to even start executing on this. So that's probably an example of we tilted a little too far towards the vision theory land. **Lenny Rachitsky** (00:42:34): And this was, you're describing the original plan to make a really good surge pricing algorithm? **John Mark Nickels** (00:42:39): Yeah. This was a plan to try to bring together, say how we do driver pricing, time and distance rates, but also we do incentives for drivers where it's like if you drive this many hours a week, you get a bonus. And there's also surge pricing and how to tie all those systems together in a very sophisticated sort of way. This was back in 2017 or something and it winged a little too hard into theory land. **John Mark Nickels** (00:43:03): And we still have that bias sometimes. We joke about marketplace, especially when we talk about with other teams that are trying to integrate in the marketplace, let's say they add fleets or teams with a big new product. And then marketplace people would be like, "Well, have you thought about this one random problem that could happen two years from now if teams become this much of demand and blah blah blah, whatever." And it's just like we do get wrapped around the axle on that sometimes. But yeah, so the future of pricing is a good example, we winged a little too far into theory land. But you could probably go too far into execution land too. And I'd say DoorDash in my experience would do that sometimes where we used to actually even half joke there, some of us leaders would be like, "It's ready, fire, aim." **John Mark Nickels** (00:43:49): And it was like, people would be like, "I'm just going to run through a wall. I have no idea if that's the right wall to run through, but at least I know I'm running through a wall." So yeah, I think it's about balance and can you adjust. Again, it's dynamic. I think there's times where you're in a soul searching sort of, "What is our product strategy? We got to pivot." Maybe you're a startup and it's not working and you want to think about... And then it's like, okay, well pull off the gas a little bit, ease up on the execution and let's lean into the strategy vision piece. And there's times where the strategy and vision's pretty baked at least for the next whatever, six months, a year. And it's like, okay, pedal to the metal. Let's just go execute. Let's get it done. **Lenny Rachitsky** (00:44:34): I just went to this Acquired Podcast event at the Chase Center. Zuck was there, and the CEO of Spotify was there too. And there's two quick anecdotes that you remind me of. One is, Zuck talked about how once Facebook and Zuck and the team align on here's where we're going, no matter how many walls appear in front of them, there's going to be a Mark shaped hole in the wall very soon because they're just going to run through and get things done that they need to get done. And I really love that mentality of once we're sure where we're going, we're going to bust through these walls. **John Mark Nickels** (00:45:11): That's awesome. **Lenny Rachitsky** (00:45:12): The other is a really interesting value at Spotify. So Daniel Ek shared this. He said, "At Spotify we have this core value, talk is cheap." And when you hear that you think it's saying talk is not valuable, and it's actually they look at it as a virtue. Talk is cheap, we can talk and it costs us no money, very little money compared to building something. So they actually spent a lot of time at Spotify refining their ideas and discussing until they're really sure something is right. And I guess any reaction to that? Because I thought that was really interesting. **John Mark Nickels** (00:45:41): Yeah, I love that. It's almost a different flavor of, I think the base of saying of he's like, I like a crisp dock and a messy meeting. The whole Amazon thing, if you have the three-page or seven-page narrative, it's written with the clarity of angels singing from on high, at least describing how the problem statement or feature or whatever. And so it's super crisp and organized and well articulated. And then you might have a meeting where you pick it apart and you talk a lot. That's what made me think of that. **Lenny Rachitsky** (00:46:12): Yeah. Awesome. Okay, couple more things I want to spend some time on. One is you've worked at a lot of really interesting successful hyper growth companies, DoorDash, Uber, Waymo. You were also in finance for a while. I want to pick on a few of these and just see what's a lesson you took away or what's an experience from that time that might be interesting or helpful to people? **John Mark Nickels** (00:46:34): Sure. **Lenny Rachitsky** (00:46:35): So you talked about DoorDash a bit. What did you take away from your time at DoorDash? What's something you saw there that either is like, wow, that's a really cool thing I want to do in the future, or here's something they weren't amazing at that I learned to try to avoid? **John Mark Nickels** (00:46:47): Yeah, yeah, it's really amazing to get to see different places and pick the best of what you like. And also the other thing is back to like, for me, there's no right or wrong, it's just differences have pros and cons. There's always two sides of the coin. So what's interesting I think about Uber and DoorDash is first back to the mission and the strategy. They started with different DNA, right? So Uber started with it was to utilize blocked cars at the airport that were not doing trips, but it was more about the riders. It was like whatever origin story you believe, Travis and whoever can get a ride in Paris. And so then it was about better than taxi and all this stuff, but it was very rider centric. It was consumer centric in that sense. **John Mark Nickels** (00:47:31): And so for a long time, I think Uber kind of took that too far. We got to the polarity of drivers are a commodity, blah, blah, blah, and they had to flip that back and start really investing more on the driver's side of the marketplace. But you look at DoorDash and it's like, Tony grew up in his parents' restaurant kitchen and the DoorDash thesis was how can we help small businesses be more successful? And delivery was just the first instantiation of that sort of meta purpose of DoorDash. And so they're much more merchant centric as opposed to consumer centric. And by the way, the consumer centricism of Uber that started with rides than translated to Eats. I think when Uber started with Eats, it was like, "Well, we just want Lenny to have some great Thai food and sushi and have some options. But selection is a means to Lenny having a great eater experience." Whereas DoorDash with their merchant focus is like, "We want every Thai restaurant in this city to be successful and be on DoorDash." **John Mark Nickels** (00:48:24): So their motivation for selection is, "We want all of the merchants to thrive and survive." So that happens to give you better selection as a result. But the motivation was very different. So the analogy I use is Uber is to Amazon as DoorDash is to Shopify, if that makes sense. Amazon has always been more consumer focused, Shopify is obviously very merchant focused. **Lenny Rachitsky** (00:48:46): Interesting. **John Mark Nickels** (00:48:46): And by the way, either of those, again, there's no right or wrong, is a fine strategy. They're both great companies. And I actually don't know if you could do both. Is it possible to be Amazon and Shopify? To really focus on consumers and build all the merchant restaurant tech? And maybe with enough resources and time, but that would lose focus. So it's like there's a trade-off there. Yeah. **Lenny Rachitsky** (00:49:08): Yeah. Like at Airbnb, there was always this, "Should we optimize for hosts? Should we optimize for guests?" And there's always this like, "This time, guests are most important. Right now hosts are more..." Make these trade-off decisions in the marketplace. So it's interesting that at Uber, your insight there is Uber is always very rider focused, and DoorDash from its DNA was very merchant focused. You also talk about at DoorDash, there's this mentality of just going before figuring out where to go. Is there anything more there that might be helpful, either as a cautionary tale or as a lesson? **John Mark Nickels** (00:49:37): Yeah, I think it's a balance. It's back to I don't want to deliberate and pontificate for weeks on end about which door I should run through. And I don't want to go to the other extreme and just spend 30 seconds thinking about what to do and just go, go, go. So it's finding that kind of happy medium. If I had to pick one, I'd rather bias towards running through a wall than not doing anything, because you still get learnings from that and you either make progress or you don't, and that gives you feedback and you can run through another wall as a result. So I think the biggest failure case is probably erring on the other side of deliberating too long without action. **Lenny Rachitsky** (00:50:15): What about Waymo? What's something that you took away from that experience as a thing that you want to do more of or something you want to try to avoid? **John Mark Nickels** (00:50:22): Waymo is, you've probably seen people in San Francisco, they're quite prolific now in terms of they're all over San Francisco and you see them all the time. And I'm not sure, I can't remember the last time I saw one towed, I don't want to say that they've solved self-driving, but they are obviously driving at scale with very minimal, at least real world intervention. You can't tell by looking at the cars how many humans behind the scenes might be helping provide guidance of the car or whatever. But yeah, I would say what's really interesting about Waymo is they've largely solved the self-driving piece, however they've done that, and in a complex environment like San Francisco, and you see them driving in fog and rain and puddles, and it's like, wow, that's pretty cool. **John Mark Nickels** (00:51:07): But I think what Waymo was learning, and I was trying help them learn is that building a self-driving car on a test track is a very different problem statement than scaling a fleet of thousands of cars. And how do you operate them, clean them, charge them, maintain them, and then how do you build the ride share network? It's like, okay, well we got to build an app and we got to acquire users and do classic growth stuff and think about that marketplace and matching and pricing and those are very different skills. And so it's like a warning that those are different things. **John Mark Nickels** (00:51:41): And trying to hire for that and build culture around that was hard, honestly. It's just like you're kind of a different thing than the host organism. Most of the host organism is just obsessed with perception and planning and all the core autonomy pieces and you're like, the commercialization people there, "Well, now we've going to make money with this thing." That's why I think that's an example where your overall vision would say Waymo is to build Waymo One. Just be mindful that it's more than just one. There's multiple pillars of that. There's the self-driving piece, there's getting a lot of cars at scale, financing them, operating the fleet, getting the demand, filling the cars with people, and then it has to all come together. **Lenny Rachitsky** (00:52:31): Right. Yeah. It's so interesting that your title is Lead Product for Commercialization of Autonomous Ride Hailing at Waymo, and now it's come full circle where at Uber, that's going to be in a sense the way that people call Waymo. And so it's so interesting that you've seen both sides of this. **John Mark Nickels** (00:52:50): Yeah. Well, we'll see what happens. I think Uber, it got out of the autonomy business when it divested Autonomous Technologies Group or Advanced Technologies Group. And right now our stated strategy is to be an aggregator. So it's like, we are partnering with Waymo, with Cruise, Motional, others in China, et cetera. And then the idea is to have every vehicle on the platform really, right? Autonomous or not. And then use the power of the platform, we have this big demand base, we have a lot of riders. **John Mark Nickels** (00:53:22): And so I think what you're seeing is, Waymo and Cruise and others are like, "Okay, now that we've developed autonomy, what's the path to profitability for us?" And so they can go it alone and try to build a ride-share network. And Waymo is doing that with Waymo One, but it turns out it takes a while. It's funny, I feel like engineers too are always skeptical of why other people's engineering problems take so much work. There'd be engineers at Waymo would be like, "Why does Uber have so many thousands of engineers? How hard can it be to build a ride-share app?" **John Mark Nickels** (00:53:59): But when you look at what made Uber successful, what we've been perfecting for the last decade, A, the marketplace tech that I alluded to earlier, but also how we manage a large rider base and doing rider support and driver support and logistics and all of the helping finance electric vehicles and working with regulators and cities and making sure we have safe and accessible pickup points and on and on and on. And those are all the depth of the iceberg that you don't really realize or think of when you're like, "Oh, I can just build a ride-share app." Right? Tesla publishes their sigma design and some earnings report and everyone goes crazy like, "Wow, okay, well I don't want to bet against Elon because that sounds scary," but there is more to it than just the app and the autonomy. **John Mark Nickels** (00:54:46): So yeah, I think these companies will have an interesting question. Do they go alone, build their own ride-share network to capture all the value, or do they say, "Well, I could just work with Uber and have a faster path to high utilization of the vehicles," which unlocks financing and more vehicles and that gets them to scale faster? And so if you look at the landscape right now, it's a bit of both, right? Waymo is obviously working with Uber in Phoenix and we just announced Cruise will come back to some city next year I think, but Waymo is also still building their own thing, so they're kind of hedging their bets at the moment. **Lenny Rachitsky** (00:55:18): I want to take us to a recurring segment on the podcast that I call Contrarian Corner. I feel like you're going to have a good answer here. What's something that you believe that most other people don't believe? **John Mark Nickels** (00:55:32): One is back to being aware of your internal state and allowing emotions and thoughts is... Emotions in the workplace, a lot of people have the thing of like, "Well, there's no need for emotion in the workplace. We're going to be logical. We're going to be data-driven. Keep your feelings at home. Just show up and presentation J.M. Mode." And I guess in my experience, there's this thing around whole body intelligence and whole body, yes, which is yes, there is signal from the head and logic and data and left brain reasoning are amazing and it could be great, but there's also heart and gut. And to me, what is an emotion? It's just energy moving on the body. Often it's correlated with a thought too as well. I might have a thought that creates fear and so forth. **John Mark Nickels** (00:56:23): But to me there's wisdom in emotion and I can start to access noticing them more. Like where do I feel sadness in the body? I notice I feel fear in the kind of center of my chest, and then sadness is like a sinking feeling in my stomach. And I notice when I'm angry, my jaw gets tight and my eyes furrow a little bit. And so those are common ones, but you may have your own little signatures of you pick up where is joy, where is creative energy? Where is fear or sadness, anger? And then noticing those in a meeting or in a conversation or review. And actually if you're willing, even just voice it to other people, that's like the next step. But start with just acknowledging it to yourself. **John Mark Nickels** (00:57:02): And so for me, the wisdom of emotions is fear is something wants to be paid attention to. There can be the saber-toothed tiger is not really Dara disapproving of me, whatever. I shouldn't be afraid of that. But there are times where fear is applicable. There might be fear around, let's say back at Waymo, you want to be really intentional about safety and you want to be super... That's one of the things I love about Waymo is they're very committed to having a super strong safety record. And so there might be fear around did we really consider all the edge cases of what might happen if a dog runs in the street or a ball or child or whatever, and you might see wow, fear. It's great. The wisdom of that is something wants to be paid attention to and listened to. Okay, great. **John Mark Nickels** (00:57:46): Sadness for me is something wants to be let go of. There's a mourning, there's a letting go of I had an idea or vision for the future that will no longer be because whatever, something happened, other people don't want to do it, this or that. But it could be a vision of a relationship, it could be a vision of what you thought your life would look like, whatever. We all go through those sorts of things. **John Mark Nickels** (00:58:07): And there might be micro-moments of sadness of like, wow, that feature didn't work. It's like I really wanted it to be successful. I just let go of that, welcome the sadness. Anger to me is something is not of service to me or my people or my mission or whatever I'm up to. And so again, that can be a great signal to like, okay, I pay attention to that. I want to change something. And then joy is something that wants to be celebrated. We had a great win. We nailed the OKR, we had a great product launch. A lot of times we spend too much time moving back into the next, okay, let's set another goal. It's like, it's okay to stop and celebrate. **John Mark Nickels** (00:58:45): And then creative energy is something wants to be born into the world. It's like it's almost like I'm going to birth an idea or a vision or some new product thing and then just tuning into that. So yeah, I would say welcome emotions, maybe even talk about them, god forbid, in the workplace. Imagine that instead of having a OKR review where you're behind target and everyone's blaming other people, and you could tell when it's kind of fearful, if someone was just like, "Wow, I noticed that I just feel fear around this." Everyone was like, "Wow, I feel fear too." That would just totally change the tone of the conversation. **Lenny Rachitsky** (00:59:20): The advice here is bring your emotions into work. Don't let emotions... What most people believe is leave your emotions at home, don't bring your emotions into the workplace, and what you've found is they actually can make you more effective and make your teams more effective. And you even talked about it helps you make decisions in a more intelligent way because your gut and lizard brain almost tells you things that you should pay attention to. **John Mark Nickels** (00:59:46): Totally. **Lenny Rachitsky** (00:59:47): I love that. Okay, so I'm going to close with a question that is rooted in something that you shared with me when we were chatting about this podcast that I think is going to be helpful to a lot of people. What have you found to be keys to a successful, impactful, rich, fun life? **John Mark Nickels** (01:00:05): It's a great question, and I think lots of people have different prescriptions for that, and I don't claim to have the one truth around that, but the first thing I would say as a meta observation is I spend a lot of time thinking about objective functions. We design algorithms to do matching and pricing and think about short-term effects and long-term effects. And so I really am ingrained in this idea of we have an objective function for our life. And then the problem is that a lot of us aren't conscious of it. It's just like an implied OF that you inherited values from your church or community or what your parents valued or what you learned to be good at, and I do this for work and blah, blah, blah, and I'm just kind of bobbing along. **John Mark Nickels** (01:00:49): That's why I love Ray Dalio's principle thing where it's like, Hey, write down your values and your principles and get clear on what they are. Or Clayton Christensen wrote a great book that he's less known for, he's obviously known for Innovator's Dilemma, but he wrote a book called How Will You Measure Your Life? And he was trying to answer this question of, he teaches whatever, MBA students at Harvard, and he's like, "Wow, all these executives are super successful. They're like Fortune 500 execs. They're most super successful, but they're all divorced and their kids hate them and their personal lives are a mess. What's happening?" And so one of the key insights he comes to is like, it's Sunday night and you have the choice of playing with your daughter, or you're reading a book or playing a game, and you have a presentation to Dara on Monday. And he's like, "Well, I could make those slides a little bit better and I could go practice or knock out some emails," or whatever it is you want to do. **John Mark Nickels** (01:01:49): And so what he basically found was the type A exec, successful people are very short-term OF driven. They're like, "Well, presentation's tomorrow, and that can either go great or okay based on Sunday night." Whereas like, "My daughter will be here, I'll play with her next week." And the problem is that he's getting in this cycle where it's like, okay, you start working every Sunday night and then years and years go by and suddenly you don't have a relationship with your daughter who's now a teenager. **John Mark Nickels** (01:02:16): But I think we're just not conscious of that. So to me, the first piece of advice would be get clear on your objective function. And one way that I've gotten clear on it is trying to think about it from future me. Because five years from now, I'm not going to give a shit if I made the presentation slightly better, but I'm going to care a lot about what kind of relationship I have with my daughters. And that means that the next action, the next thing I do today and tomorrow, those will translate into the relationship with her. And I think a lot of us aren't just tuned into that. **John Mark Nickels** (01:02:49): I love the stoic stuff, being mindful of death, Seneca, Marcus Aurelius, all those great ones. Not to be morbid, but just again, most of us just aren't really tuned into an awareness that our lives will come to an end. And we try to avoid that and we try to pretend like we're going to live forever and just not think about it. And the horror of it is that we succeed. We mostly manage to just go live our life and eat ice cream and go to work and go on vacation and do what we do. And that can lead us to doing things that ultimately don't matter in the long run, and focusing on the wrong things. **John Mark Nickels** (01:03:28): And so to me, it's like an awareness and mindfulness that our lives will come to an end punctuates reality in a way that requires me to rethink my priorities, stop wasting time on things that don't matter with people who matter. This relationship, this journey, it will come to an end. I'm actually tearing up and feeling tingly just saying that. It's like even right now, come back to it. How am I going to spend my afternoon? Am I going to hug my daughters? Am I going to spend time with them after work or am I going to do email all night? What would I wish I had done when I'm in my last breath? **Lenny Rachitsky** (01:04:18): There's a quote that I heard once that really stuck with me that I think is going to hit a lot of people really hard, which is that the only people that will remember you working late every night is your kids. **John Mark Nickels** (01:04:32): Wow. Yeah. **Lenny Rachitsky** (01:04:34): Yeah. An important reminder. J.M., we've covered a lot of stuff. Is there anything else that you think might be helpful for people that you want to leave listeners with? Or we're going to have a lightning round coming up, but before we get that, we ended on a really powerful, impactful note. Is there anything else along these lines that you think might be helpful for people that you want to leave them with? **John Mark Nickels** (01:05:01): The one thing I'd encourage folks to do out of all of these we talked about is to see if you'd be willing to commit to breaking out of victim consciousness and mentality. And it's not to say there aren't victims in the world, there are real injustices and things happening, but most of us, I've experienced, I often can fall into the trap of living my life at the effect of, right? I'm at the effect of other people and what they do. I'm at the effect of circumstances like COVID or Trump or whatever. I'm at the effect of the conditions and circumstances of life, and I feel like life is happening to me. **John Mark Nickels** (01:05:39): And so to me, the most empowering and radical transformation that I've been able to cultivate and develop is shifting from that to a state of I I am willing to take responsibility for how I see the world. And I may not be able to change the weather or the election or all that, but I can change how I'm being in relationship to it and choose to see it as a growth opportunity, as learning, how am I co-creating it, even things that I play a small part in, injustice in the world, how am I perpetuating that and being willing to see the world as I'm the painter of my existence? **John Mark Nickels** (01:06:11): I think Viktor Frankl's Man's Search for Meaning is probably the best example of that. He's in a super oppressive situation that is very horrific and tragic, and the way he described his relationship with the people in the camp and the guards, and he given he gave a talk after he was free, the amount of compassion and empathy he had for his oppressors was just amazing. So I'm like, well, if he can do that in the face of those conditions, I can show up differently in a product review or in a conversation with my partner or meeting or whatever it is. **Lenny Rachitsky** (01:06:46): Yeah, I think just that skill alone is such a powerful unlock for a lot of people instead of, here's all the things that I don't have and here's all the things that are setting you back and all the things that are hard for me versus other people. Shifting to, I need to take responsibility for my own success and no one else will. And just taking agency is a really powerful thing. It's easier said than done. There's a lot of hardships. People have a lot of things that they don't have that other people have that are hurting their career and hurting their ability to be successful, but still, the more you can take responsibility and have agency and the less you have this victim mentality, I 1,000% agree, there's so much power there. So that's an awesome lesson to end on. With that, we've reached our very exciting lightning round jam. Are you ready? **John Mark Nickels** (01:07:34): I'm ready. Let's do it. **Lenny Rachitsky** (01:07:35): Okay. First question, what are two or three books that you've recommended most to other people? **John Mark Nickels** (01:07:41): In the realm of the soft skills and conscious leadership, the best one is the 15 Commitments of Conscious Leadership by Diana Chapman and Jim Dethmer. And those were my early coaches and teachers almost 10 years ago, and Diana is still my coach. So I think that's a fantastic book that we'll go into more detail about some of the things we talked about around fear and threat versus trust and drawing a triangle and all that great stuff. That'd be one that I'd definitely recommend first. Another one more in the content world is I think you had Nancy Duarte on your podcast one point. **Lenny Rachitsky** (01:07:41): Yeah, Nancy Duarte. Yeah. **John Mark Nickels** (01:08:17): Or Duarte, sorry. I love her book Resonate. I know she has some other ones too, on slide design and stuff. But what was so cool about that, I gave it to PMs all the time when I'm trying to help them develop their communication, storytelling, and presentation skills. And she goes through those TED talks and Martin Luther King, I have a dream, and going to the Moon, and basically make the spark line against it to understand this concept of resonance with the audience. It's actually a great skill for, back to vision and north-starring, she said what all these things do is they alternate tension between the world as it is and the world as it might be. And it's like, here's that beautiful future of transportation, San Francisco, blah, blah, blah, but here's why it sucks today, all these problems and this and that, but here's how it could look in a few years. **John Mark Nickels** (01:09:05): And then you're creating that tension and the audience at the end is like sweaty palms and like, "I want to help build that future." What do you need? You need money, you need time, resources, join your company. Great. So anyway, Resonate, Nancy Duarte, great book. Those would be some of the top two that I recommend. There's not one specific book, but I really love Alan Watts' books if you're into... He was one of the first people to articulate and kind of import Buddhism and that sort of Eastern thinking into the West, and he just has a very satirical, comical sort of not taking myself too seriously style and just like the way he explains a lot of those concepts. So that'd be another one. **Lenny Rachitsky** (01:09:47): He also has an amazing voice if you listen to recordings of him with music, it's just so fun to listen to. **John Mark Nickels** (01:09:52): Totally. Actually, Sam Harris's Waking Up app now has the entire... he worked with I think Alan Watts' son. So the Waking Up app has all 80 or 100 hours of recorded Alan Watts lectures. **Lenny Rachitsky** (01:10:03): Oh my god. There's YouTube videos. **John Mark Nickels** (01:10:06): [inaudible 01:10:06] **Lenny Rachitsky** (01:10:06): There's some awesome YouTube videos of him that are worth watching, we'll link to some of those. And then Nancy Duarte, she shared exactly that lesson on the podcast that we had together. So if you don't want to read the book and listen to her give this tactic of this way to communicate a vision, you can listen to that episode, we'll link to it. Next question, do you have a favorite recent movie or TV show you have really enjoyed? **John Mark Nickels** (01:10:28): Yeah. The last movie I really enjoyed was Inside Out 2 with my kids, which is very- **Lenny Rachitsky** (01:10:34): I could see why you'd love that. **John Mark Nickels** (01:10:36): Yes, consistent with the emotional awareness and allowing the different emotional parts and don't want to spoil the movie, maybe everyone hasn't seen it, but it's very simpatico with that lesson of you can't just let one emotion run the show, they all have wisdom. On the first one, Sadness, Joy learning that Sadness is necessary. It's all about integration, but it was beautiful the way kids understand it and it's a way to teach emotional literacy to your kids. So I think what they've done there with those Inside Out movies is just brilliant. **Lenny Rachitsky** (01:11:06): Do you have a favorite product you've recently discovered that you really love? It could be an app, it could be something physical. **John Mark Nickels** (01:11:11): Yeah, so Eight Sleep is a smart mattress company. They're on their third or fourth rev now, but it's like a Tempur-Pedic mattress, or you can put their cover on any mattress, but it has a cover that has little tubes of water, and then it has a little computer thing and you fill with water and then an app. And basically what you do is you program it and it learns, it has sensors, it can measure your heart rate, your HRV, body temperature, all that, but you're basically trying to program a temperature curve to help you maximize your kind of REM sleep and deep sleep and get more value out of the sleep that you do have. **John Mark Nickels** (01:11:41): And so for me, it's super cool early for deep sleep, and then it warms you up as you want to wake up, which is... or an alarm and all that. But it's back to my thing about wanting to show up with the right mindset and energy and aliveness. Having really high quality sleep has been a really key part of that, is like if I don't sleep well, I didn't get enough sleep or didn't sleep well, you're already starting off on a bad foot. So yeah, if you haven't checked out Eight Sleep, great product. No endorsement fee for me. **Lenny Rachitsky** (01:12:12): What's also cool about it is it tracks your sleep. It gives you all these stats. Instead of wearing a ring, and it gives you all these stats about your sleep quality. And there's this guy, Brian Johnson, I don't know if you follow him, he's like this guy that's trying to stay alive as long as possible, and he had a perfect sleep score for six months in a row to set the record. **John Mark Nickels** (01:12:30): Wow. **Lenny Rachitsky** (01:12:30): Yeah. He knows what he's doing over there. Okay, two more questions. Do you have a favorite life motto that you often come back to, think of, find useful in work or in life? **John Mark Nickels** (01:12:42): Yeah, I probably have had different ones over the years. The one right now that really serves me is there's this track called Sit Around the Fire by Jon Hopkins, but it's on Spotify, Apple Music, but it's basically music with one of Ram Dass' talks, lesser known talks. And so the mantra that's been really serving me recently is the very first part of that, which is he says, "Beyond all polarities, I am. Let the judgments and opinions of the mind be the judgments and opinions of the mind. And you exist behind that." So sometimes I have an abbreviated version of that where I'm noticing I'm activated, I'm clinging to an opinion, I'm arguing with somebody, and I'm just like, "Beyond all polarities." **Lenny Rachitsky** (01:13:44): An abbreviated version. **John Mark Nickels** (01:13:45): I do that in front of my kids and they laugh at me like, "Daddy is so weird sometimes." **Lenny Rachitsky** (01:13:47): Beyond all polarities, kids. That's so funny. Oh man. There's another Ram Dass line that I often use with my wife, Be Here Now, which is the title of his book that everyone sees with the blue cover. And I do that when she's on her phone and we're doing something. I'm like, "Be here now." And she's like, "Okay, okay. I'll put my phone away." Yeah. Final question. I was going to ask you about the line tracking and what you learned from that. You already shared an awesome lesson from that time. So let me ask you something else. I'll ask you about Travis. Any crazy, fun, memorable stories of working with Travis Kalanick? However you say his last name, Kalanick, Kalanick? **John Mark Nickels** (01:14:27): Travis Kalanick, yeah. Yeah. I'll share a quick one that's short but sweet or hilarious to me, and maybe lesser known. So we used to have the Uber office at 1455 Market, and so there was one conference room where we'd often do reviews with Travis, and it wasn't the war room, whatever whenever room it was. That was interior and no windows. So this room had windows overlooking, what was that? 11th street. So 11th and Market. And so we'd have a presentation up on the projector, some big screen we're about to go through something with Travis. And reliably, every time he'd come in, he would close the blinds of the windows. Everyone like, "Travis, what are we doing?" It's not because there was glare. They were orthogonal to the screen. And then one time I was like, "Why are you doing that?" He's like, "I'm pretty sure Lyft has drones outside the windows of our office and they're spying on our presentation." **Lenny Rachitsky** (01:15:19): Oh my gosh. **John Mark Nickels** (01:15:23): I was like, whoa, your competitor paranoia runs deep, man. Okay. Yeah, yeah. Anyway. **Lenny Rachitsky** (01:15:32): It's hard to mention Lyft doing that. I could see Uber doing that to Lyft. **John Mark Nickels** (01:15:36): Old Uber. Uber 1.0 **Lenny Rachitsky** (01:15:38): Old Uber. Yeah. Wow. That's amazing. It's like coaches in the NFL that are covering their lips always when they're telling and giving plays, just like, I wonder if people actually do that. That's amazing. Yeah, I get that. It's like high stakes. You never know. Might be a drone out there. **John Mark Nickels** (01:15:54): Right. **Lenny Rachitsky** (01:15:54): Amazing. J.M., what a roller coaster of a conversation. We covered so much ground. I can't even name all the things we covered. So let me just ask you two final questions. Where can folks find you online and reach out if they want to work with you? I know you work with folks, talk about that. And then finally, how can listeners be useful to you? **John Mark Nickels** (01:16:13): Yeah, yeah. So I am occasionally on Twitter @NickelsJM, but I don't tweet a lot, but maybe I should start. But the best way to find more about my thoughts and thinking on the soft skill stuff is a website called rhythmofbeing.com. And I've got some blog posts and stuff there that go into detail on some of these things. And yeah, I do a little bit of coaching on the side with folks. I do very little now. My day job at Uber and my night job with my kids takes up most of my waking hours. But for the right person and a few select spots, I can make time. But yeah, that's the best place to find me, is rhythmofbeing.com. **Lenny Rachitsky** (01:16:55): And then how can listeners be useful to you? **John Mark Nickels** (01:16:57): Well, in the spirit of welcoming and embracing feedback, you could most be useful by reaching out, telling me what resonated, what didn't, what was useful, where did your energy go up when I talked, and where did your energy go down? Because that to me is a signal of where I'm back to tracking the life, where's the juice? And then that way in the future when I do other versions of this or other conversations, I'll pay more attention to the energy up stuff and go more there, and the energy down was like, okay, maybe that wasn't as interesting or didn't resonate. Great. No problem. **Lenny Rachitsky** (01:17:35): J.M., thank you so much for being here. **John Mark Nickels** (01:17:38): Thank you for having me. **Lenny Rachitsky** (01:17:39): Bye everyone. **Lenny Rachitsky** (01:17:42): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [3/17] Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking) **Tristan de Montebello** (00:00:00): People tend to get into a public speaking voice. We'll be in a class and they'll be chatting normally and look super normal. And then we'll say, "Okay, now just a timer, I'm just going to give you a speech. Just speak for 60 seconds so we get a baseline," and I click play, and suddenly I say, "The important part about doing this," and they enter into a different version of themselves, a professional version, whatever that would mean. It's so much more freeing, powerful, connecting, and effective to speak conversation. So the cue I often give people is- **Lenny Rachitsky** (00:00:36): Today my guest is Tristan de Montebello. Tristan is the co-Creator of Ultraspeaking, which is the best public speaking workshop I have ever come across. In 2017, Tristan became the fastest competitor to reach the finals of the world championship of public speaking. And based on that experience, built a very unique course that helps you quickly build the skills to become better and to become more comfortable speaking in public, and especially speaking on the spot. **Tristan de Montebello** (00:01:49): Thanks so much for having me. **Lenny Rachitsky** (00:01:51): So I took an abridged version of this speaking course that you teach called Ultraspeaking, and it immediately made me feel more comfortable public speaking, which I've never felt doing any other course. Public speaking is something it's just is very scary to me as it is for a lot of people, but it's just something I really dread. Even doing these podcast episodes, every time I get nervous before doing these things, as much as it may not seem that way. So this is not my natural habitat speaking, being in public. It may not seem that way to people, but it's true. **Lenny Rachitsky** (00:02:22): And the way you approach this stuff is so unique and worked for me. And because of that, I thought it'd be awesome to just bring you on this podcast and basically try to teach people the stuff that you've learned about how to become a better public speaker. I know we're not going to do your course here, but just, what are some very tactical things people can immediately start to apply? And also, I want to make the super interactive, so we're actually going to do some of the exercises that you use in your class. So that's what we're here for. How does that sound? **Tristan de Montebello** (00:02:54): That sounds exciting. I'm in. **Lenny Rachitsky** (00:02:56): Great. **Tristan de Montebello** (00:05:49): I actually think that the biggest misconception with tackling your speaking is that people grossly underestimate just how transformative it could be to your life. And the reason it's so transformative is because speaking is not a specialized skill, it's a meta skill. That means that the better you get at speaking, the better your life gets. **Lenny Rachitsky** (00:06:16): So an example of a meta skill is fitness, for example. If you were to start saying, "Okay, I'm going to transform my fitness," and you start lifting weights and you start going on runs, obviously your muscles are going to get bigger, you're going to get more in shape, and your cardiovascular system is going to improve. But that's actually only a sliver of the impact it's going to have on your life because you're going to start feeling more energy, and you're going to start having these nice hormones, these endorphins flowing through your body and you're going to feel better about yourself. And when you walk in front of the mirror, suddenly you're going to have a boost in confidence. So naturally, everything else in your life is going to start to improve as a result of you focusing on your fitness. And for speaking, it's the same thing. **Lenny Rachitsky** (00:07:01): This blew my mind when I went on my own speaking journey, is when I started making breakthroughs in speaking, other things started to feel different. So as you get breakthroughs, how you feel at work feels different. How you feel in your group of friends feels different. How you feel in a group of strangers, especially, how you feel and your family can even be impacted. This seeps into everything else in your life. But the thing is, because there's so much self-consciousness that goes with speaking, we often feel kind of constraints under the layers of overthinking and anxiety that come with speaking. So it can be hard to realize that underneath these layers, you actually have this extraordinary superpower, because as humans we're evolved to speak, this is what we are. So you don't need to teach a baby how to speak, it will learn by itself with no formal education. So what that means is, we all have this incredible hardware. **Lenny Rachitsky** (00:08:12): The thing is, over the course of our life, because of all these little situations that happen, we start getting bugs in the software and we're not really upgrading our software. The moment you get the bugs and things start working, not working, we start avoiding, and suddenly it's like we're not upgrading our software anymore. So we're stuck on old, buggy software. But the reality is, let's not forget that we have incredible software that were evolved for this. So all we need to do is some debugging and some upgrading of the software and suddenly your entire life can change. So that's really one I want to impart on anybody listening. You have it in, you already have what it takes. **Lenny Rachitsky** (00:08:56): Okay. So kind of building on what you just talked about, some of this insight of, your life can improve and how you kind of always have to unlearn stuff. One of my favorite maybe core insights and tenets of the way you approach teaching people to speak, is you talk about how if you don't enjoy speaking, you're doing it wrong. And that really helped me because you kind of encourage, you kind of remind people, try to have fun as you're doing. Can you just talk about that insight and why that's important and how that helps people become better? **Tristan de Montebello** (00:09:26): Well, I think that's very tied to what you were saying. I see enjoyment as a barometer, if I'm doing things right, I'm probably enjoying myself. If I'm doing things wrong, particularly with speaking, because again, this is something we're naturally evolved to do. So if we're naturally evolved to do it, it's not something that we dislike doing. It has to be something that rewards us. So as soon as things start not feeling enjoyable, it's a sign, hey, I'm probably doing this wrong, guy. There's something here that I'm doing that is making this unenjoyable that's probably not helping me. **Lenny Rachitsky** (00:10:03): And I think you mentioned that in those people who can hold an audience who are really good communicators in business, it looks like they feel very comfortable, it looks like they feel like themselves. And if you think about speaking, when you're talking with your kids, or with your partner, or with your best friend, your childhood friend, your parents, ever, we all have environments where we feel completely like ourselves. And when we do, communication is extraordinarily enjoyable. It's just a means to connect with other people, a means to share what we have on our mind and it's very, very empowering and it feels very good. **Lenny Rachitsky** (00:10:42): Then I take the same person with the same skill set and the same ability and I bring them in a business setting, and suddenly I don't feel like myself anymore. And because of the pressure, I start trying to speak differently. So people start having, I'm going to try to think really hard of what I need to say and I want to control the words that are going to come out of my mouth before they come out of my mouth so I make sure I don't make a mistake. And you basically loop in this thing that is so counter what communication is, which is just a natural subconscious scale. So using speaking as a barometer of, hey, if this is not feeling good, I'm probably overthinking. I probably need to relax and try to just feel a little bit more like myself. **Lenny Rachitsky** (00:11:27): But this also applies to practice, where in your practice, because this is not an overnight thing, you can't just snap your fingers, read a book, and be a better speaker. Well, your practice has to be enjoyable as well because otherwise two weeks in, you're going to quit just like a shitty fitness journey or diet. Right? You have to find joy in it and it has to be structured in a way where it rewards you as well, so that you get more energy and you get more enjoyment while you do it. **Lenny Rachitsky** (00:11:58): Awesome, and we're going to show people how you do that. You do these games, they're games that you play that help you actually learn these skills. So before that, and also I want to get into actual tactics that we can just give people to become better public speakers. But right before we get there, are there any other core insights or principles or lessons that are fundamental to the way you found that it works to become a better public speaker, that kind of inform a lot of the stuff we're going to be talking about? **Tristan de Montebello** (00:12:25): The day I understood that speaking was a subconscious flow-oriented process and not a conscious process, completely changed the way I approached it. So instead of thinking tactics and frameworks and adding more to the outside of the things I need to think about, when I realized when I speak best, I'm actually not thinking about speaking. It's the last thing I think about is the speaking part. I'm completely in tune with whatever it is I'm trying to convey to my audience or the person in front of me. And the goal is to get into a flow state and stay in that flow state all the way through the finish line. That's what really, really changed my mindset about speaking, because then it changes all of the exercise, the exercises you want to do. It changes how you can think about speaking. **Lenny Rachitsky** (00:13:24): And one of the ways that changed how I practiced was, instead of focusing on the symptoms of speaking, I started to try and figure out, well, what are the root causes that create these symptoms, and can I address those? So instead of counting my filler words, if that's something that's annoying to me, I'm going to go back and try to figure out, well, what's the root cause of that? Well, the root cause of having lots of filler words or racing in your speaking, is that you probably struggle to feel comfortable slowing down, relaxing, or even pausing when your mind is racing and you feel pressure. Solve that, and not only do the filler words take care of themselves, but the racing takes care of itself and you suddenly have more mind space. **Lenny Rachitsky** (00:14:11): And if you feel super constrained in your speaking, very monotonous, then maybe you feel boxed in and you're struggling to allow yourself to feel to be all of what you are under pressure because there's probably a lack of certainty. A lack of trust in, hey, if I let myself be more intense or if I let some of these emotions pop out, or if I take a time to gather my thoughts, is everything going to unravel, or is that going to work for me? And if you haven't proven that to yourself, then you're just going to go for safety and so you're going to be very monotonous and constrained, and that's creates monotony. But if I can solve that, suddenly I have freedom. So thinking through this and understanding that the goal here is upgrading the software and it's really layering, taking all the bad habits away and putting in new habits that I can just stay in this flow state without getting pulled out, that really changes the game. **Lenny Rachitsky** (00:15:15): That is a really interesting insight, and I love that you actually demoed that in the way you answered this question, where you took time to get into that state and not just get, um... It's just like, pause. **Tristan de Montebello** (00:15:28): Pause. **Lenny Rachitsky** (00:15:29): Yeah, that was a really beautiful example of that. Okay, let's get into a few tactics just to give people something they can- **Tristan de Montebello** (00:15:29): Sure. **Lenny Rachitsky** (00:15:34): ... actually change about the way they speak this week. What are two or three things that you can recommend people tweak in the way that they do public speaking, in the way they speak in meetings and presentations, whatever? **Tristan de Montebello** (00:15:47): I actually thought about this because once you think about speaking being much more about the root causes, like play the games that are going to change you at the root, don't focus on the symptoms, then you find yourself sharing much less purely tactical advice and frameworks because we're trying to get out of our brain into our subconscious. **Lenny Rachitsky** (00:16:10): So when I thought about it, I thought of three things I wanted to share. One makes you sound better or look better, one makes you sound better, and one makes you feel better. So the first makes you look better. Now this is super basic and very crunchy, but it's a bad habit that a lot of people have. That when I am trying to gather my thoughts or think, people tend to look down. And if you're looking down on Zoom, it's three times as bad because it looks like you're looking at your phone or looking at notes if you had any, but even when you're in person, it doesn't look very confident. And so you're suddenly giving off of that vibe of, oh, this person feels a little bit uncertain here, and maybe it's going to look like you stopped speaking and you might get more interrupted. **Lenny Rachitsky** (00:16:56): If instead you switch that up and you start thinking up. I think up into the right, but you can think in any direction you want, but as long as you're looking up, you actually look thoughtful by default. So suddenly you're looking thoughtful. That means you look more confident because anybody who'd be willing to pause in their speaking is somebody who's confident. And as a result, you're much less likely to get interrupted. So it's a small tweak but makes a real difference. **Lenny Rachitsky** (00:17:24): The only thing is if you're not used to doing this, if this is not your habit, then it's going to feel a little bit awkward the first time you do it and you probably won't think about doing it. So I recommend writing, think up, on a post-it and putting it on your computer so that it's there for you. And then once you've done it a few times, this will become the new normal and by default, you'll look more confident. **Lenny Rachitsky** (00:17:46): I'm going to do this as we talk. I have a poster right here. Think up., **Tristan de Montebello** (00:17:48): Oh, nice. Think up. **Lenny Rachitsky** (00:17:50): Okay, great. What else? **Tristan de Montebello** (00:17:53): Look more confident. Now how to sound more confident. This is a really important one, and this concept is called end strong. And it's, we had to bring this up because most people tend to end weak. And why is that? They put freestyle rappers in an fMRI, and what they found out is freestyle rappers have to enter a deep flow state. If you're freestyle rapping, you have a beat, you don't have any lyrics, and you have to get into the beat and invent the lyrics and the melody and everything on the fly. So there's no choice but being completely present. What happens is you can see their brain and it's lit up in a very specific place that shows that they're in flow, and when they get to the very end, the brain just blows up. Before they finish, they start getting pulled out of flow. And this is the same feeling of you're running at school and you see the finish line and just a few yards before you start slowing down. It's just, I don't know, we're built that way. **Lenny Rachitsky** (00:18:53): And in speaking, it's the same thing. People tend to give a great answer and then either they kind of taper off at the end, which doesn't leave you with a good impression, or they'll actively say the doubts that are coming up in their mind of maybe they'll be giving a great answer and then suddenly they say, "I don't really know if that makes sense." **Lenny Rachitsky** (00:19:10): I do that all the time. That's very relatable. **Tristan de Montebello** (00:19:13): Yeah, but what the thing is, what happens when you do that? When you do that, it's like you're forcing this lens on your audience, where now even if they had the best of experiences with your answer, now they're looking at everything you said through the lens of, oh, this person was kind of uncertain. So it's like you had a very smooth flight across the Atlantic and your landing was absolutely horrible. You were bumpy when you were coming up, and then when you hit the landing, you bounced three times and you thought you were going to die. You're not going to remember the smooth flight, you're going to remember the ending. So a simple tactic here is, anticipate that as you get to the end of anything you're saying, you're going to naturally start regaining consciousness and you're going to start being a little bit more self-aware, and some of those uncertainties are going to pop up. Know that it's coming and make sure you land the plane. **Lenny Rachitsky** (00:20:14): So what that looks like is, either you just make your ending sound like an ending and then leave it at that, or you can prompt your brain. You can use summary prompts, this is incredibly powerful. It just means you say the beginning of a sentence or the beginning of, yeah, the beginning of a sentence, and your brain's going to fill in the gap. It's going to. You're prompting your brain and your brain will always deliver. So you get to the end, you're like, okay, I got to wrap up now. And so you'll say, "So to wrap up..." And your brain's going to fill in the gap. Or, "In summary, so my point here is, so what I want you to remember," and you just place those words and your brain's naturally going to do the work of closing it for you. But make sure you don't let go of the gas pedal at the very last moment, you need to land that plane. **Lenny Rachitsky** (00:21:01): Awesome. I could definitely get better at this, great tip. **Tristan de Montebello** (00:21:04): Yeah, thanks. **Lenny Rachitsky** (00:21:06): I'm going to try to do that as we talk. **Tristan de Montebello** (00:21:07): Yes. **Lenny Rachitsky** (00:21:07): And what else we got? **Tristan de Montebello** (00:21:09): I'll be paying attention to that. **Lenny Rachitsky** (00:21:11): Okay, pressure. **Tristan de Montebello** (00:21:15): Yeah. The third one is staying in character. And these go hand in hand. And what's really powerful is when you start doing these, there's a beautiful feedback loop that happens that gives you a lot of confidence. So staying in character I said is the one that's going to make you feel more confident. **Lenny Rachitsky** (00:21:33): What's staying in character? So it's related to end strong in some sense, in that people tend to self-sabotage a lot. I'm speaking, and obviously as I'm speaking, all of my senses are really, really heightened. So I'm aware of everything, if a word comes out a little bit weird or if it's not the word that I was expecting to hear come out of my mouth, I'm going to be very aware of that because I was expecting something and something different happens. But that happens all the time when speaking. I'm starting to not make as much sense or I feel like I'm rambling, going a little bit too long. All of these create insane noise in the back of my mind, the insecurities. And you have a choice there, because I can tell you right now, nobody can tell. People cannot see what you feel, even though it feels that way when you feel really, really strongly, but people can't see it. You're just looking like a normal speaker, competent and confident. But internally, it feels like everybody can see. **Lenny Rachitsky** (00:22:34): So you're feeling all this insecurity and it feels like there's an elephant in the room. And so what most people do is they start leaking and they break character. And they'll say, "Oh, man, I'm not making sense right now," or they'll laugh nervously after saying a word that came out weird, which is kind of saying like, "Oh, I also noticed that this word came out weird and it's okay." Right? Or they'll keep letting all of the insecurities and doubts come out when people didn't see it in the first place. So again, it's like I'm forcing these filters onto my audience and now they can only see me through that light. **Lenny Rachitsky** (00:23:15): And so one analogy I love for this is, again, a flying analogy. You're on the plane, everything's smooth, you're having a great time watching your movie, and suddenly you're interrupted by the pilot who picks up the intercom and says, "Oh, ladies and gentlemen, so I just had a red light start blinking here in the cockpit, and I'm not sure what this is. It could be really bad, honestly, but I don't know. So don't worry, please, I'll get back to you soon." First thing that's going to happen if you experience that is you're going to think, I wasn't worrying in the first place. But then you start thinking, wait, something probably is going wrong. And now the smallest noise, the tiny little bit of turbulence, a creak on the right, you're going to start thinking, oh no, we're going to die, every time. **Lenny Rachitsky** (00:24:03): So you're going to make any little mistake, any little imperfection, you're going to turn that into something big. That's what happens when you speak. If you start leaking and letting the insecurities come out, people are going to start thinking, this person doesn't really know what they're talking about. It's like a leader who isn't clear in their direction. Suddenly I'm thinking, wait, I think I have to second guess everything here because I'm not sure about this guy or this person. **Lenny Rachitsky** (00:24:33): And the good news is, the solution is very, very simple. The solution is that is just, don't share your insecurities. Put your best foot forward and stay in it the whole time. Stay in character from beginning all the way through past the ending, because you go all the way through your speech, then you got to end strong, which is a form of staying in character, and then let it be. And that's so important, just let it be and you're going to notice something incredible. If you're the type of person who would break character a lot, start staying in character, and the cue use for myself is, stay in it. And the worse it gets, the more I'll say, just stay in it. And what happens is, you stay in it. **Lenny Rachitsky** (00:25:21): And you expect everybody at the end to say, "Oh my God, you looked so uncomfortable, what was happening?" But people can't see that, that you look confident. So they're just going to give you the reaction that a confident person would get, and you're going to notice, oh wow, I am coming off as confident, and that's going to make you feel more confident. And so it's a very reinforcing cycle. If you start staying in character and ending strong, naturally, you're going to be reinforced by this behavior and you're going to realize, oh, I didn't need to break character. I didn't need to hedge every time I spoke, and that's going to give you much more confident, and you're going to start realizing, people just look confident by default. This is a crazy thing. I want everybody to walk around the world and look at people and think, most of the people I'm looking at are actually nervous right now. You're going to look at them and you're like, I can't tell. Most people speaking up in meetings are feeling a level of nervousness, but you can't tell unless it's through the roof. **Lenny Rachitsky** (00:26:23): I love this, and it's something I'm extremely guilty of. And I think the reason I do this and the reason I think a lot of people leak, which I love that term of just I don't leak, that you know, feel something's not going right. The reason I do it is I feel like me being upfront, I know this isn't great- **Tristan de Montebello** (00:26:41): Exactly. **Lenny Rachitsky** (00:26:41): ... makes it okay, but in reality, that's hurting you because it's like when I watch standup comedy. When the comedian's like, "Oh, sorry, that bombed," if he didn't say that or she didn't say that, I'd just forget about it, and we'd move on to the next thing. And it brings all this attention to, oh, I see, okay, it's not going great. Otherwise, you're just like, all right, whatever, I didn't like that joke. And so, yeah, I guess any thoughts on just that, why people do this? **Tristan de Montebello** (00:27:07): Well, I think that's exactly that. It's because you're convinced that everybody can tell. And so two things will happen. Either they could tell because it was a big thing and everybody could tell, but you shining light on it is literally that. It's like, hey, everybody, you're driving a train, everybody's in the train, you're the driver as the speaker, everybody's going with you. So if there's a crash on the side of the road, you can keep going and they'll not be looking at the crash a second later and they'll be looking at the next landscape, or you can stop the train and tell everybody, "Hey, let's look at this crash here real quick. I'm so sorry about it." When you keep going, people will forget it in a second and they're not going to pay attention to you. And with the peak end rule, what we we're seeing, people remember the end of experiences more than they remember the beginning of experiences. So you're going to be left with that feeling at the end. **Lenny Rachitsky** (00:27:58): The other piece is, because most people won't notice it in the first place, they'll be in their own minds. So when you share this, you're popping their bubble. And so I see people speaking all the time where I'm super in tune with the feeling I'm getting when they're speaking. I'm listening to the energy, I'm listening to everything that's happening, so I can try to understand, what state are they in right now? So when I get woken up from that state of somebody saying, "Oh man, can I go again right now? That really sucked." It's even more visible for me. **Lenny Rachitsky** (00:28:36): And I'll often have to say, "Hey, man, I was so into what you were saying," and I'll poll the audience, "is anyone surprised?" And everybody every time is like, "No, I thought that you were doing great. I was completely with you." So that's the case most of the time, but because we're convinced that people can tell, we want to break that fourth wall or because something happened and we know people can tell, we want to acknowledge it so it doesn't feel like I'm the only one in the room who can't tell that something went wrong here. But this habit of saying, "No, I'm going to be confident, I'm leading, I'm going to keep us going in a certain direction," is extremely powerful and very self-reinforcing. **Lenny Rachitsky** (00:29:18): Okay, so let's actually show people what this looks like by actually doing some live games. I know one of your principles for Ultraspeaking is you can't learn to speak by not speaking. You need to practice speaking to get better at speaking, and these games are a way to actually do that in a really fun way. So maybe first of all, just why games? When I did this course, I was just like, huh, because it's a bunch of games. I thought this was a public speaking course. So maybe talk about just why you approach it through games, everything you do is a game in this course. **Tristan de Montebello** (00:29:48): Yeah. Well, the first piece of the puzzle is what you were saying, that you can't get better at speaking without speaking. And it's, intuitively you could think, everybody knows that if you want to become a great cook, you can't just read 100- **Tristan de Montebello** (00:30:00): Everybody knows that if you want to become a great cook, you can't just read a hundred cookbooks. You actually have to spend most of your time in the kitchen refining your intuition, testing things, experimenting, learning new recipes, and building your timing and everything that goes with it. But in speaking, we tend to do the opposite, probably because it's a little bit scary and because there aren't that many options out there to practice the speaking itself. There aren't that many environments where you can do it right now. So we're kind of left with nothing, so, "Okay, I'll just go read an article or watch a YouTube short and hope that's going to make a difference." **Lenny Rachitsky** (00:30:38): But maybe the bad news is, you have to do it. You have to ask yourself, "Am I going to be serious about taking on speaking and making a difference here?" And if you are, then you're going to have to do the thing. You have to practice speaking. But the good news is, it's only the outside that's scary. As soon as you get started, you're going to get rewarded. And then, the better you get at it, the more enjoyable it becomes. **Lenny Rachitsky** (00:31:03): So why games then? Well, games number one, are fun to play. And as I was saying earlier, if your practice is not fun, you're going to stop. So you need intrinsic reward with what you're doing. But what all of the Ultraspeaking games have in common is that it's short, deliberate practice, short reps followed by feedback, followed by another rep. So that was more important than the idea that it was a game at first. **Lenny Rachitsky** (00:31:35): When we started coaching with Michael Gendler, my co-founder, it was just him and me in my backyard with somebody in front of us testing things out. And we would say, we would give him a speech title just to get a baseline. "Okay, what's the most incredible invention in the world?" And we'd watch this person go into their mind and start freaking out. And they'd think, " The iPhone," and then, "I don't know the iPhone. That's pretty recent. So maybe it's fire. Is it fire though? Was there a bigger maybe communication? I don't know. Wait. Maybe we've evolved for communication." **Lenny Rachitsky** (00:32:08): And the longer they spent thinking, the worse their answer tended to be, and the more their confidence tended to go down as they were speaking. So then we said, "Well, we've got to get this person speaking right away." So we'd say, "I'm going to ask you another question, but just start speaking." And so, I'd ask them another question and they couldn't start speaking right away. **Lenny Rachitsky** (00:32:27): So we just tried to compress it more and more and more to turn it into something where then it was like, "I'm just going to say a word and you have to say something about it, so horses." "Horseback riding is fun because you can go places." "Cats." "Cats are crazy because if they were bigger, they would eat you." And I just, almost like word association. Let's get words out. **Lenny Rachitsky** (00:32:46): Then we started developing different games for everything. Every root cause we were seeing, every symptom we were seeing, we'd figure out the root cause and we'd create some sort of a way to get the person into it as quickly as possible. And it's just one day, six months in that we realized, "Hey, did we just create a game? This feels like a board game." And then we created, I have this, we created Speak Before You Think, the game for people who think too much, and this is a bunch of cards with all of our games. And then, Covid hit and we turned it into online games. **Lenny Rachitsky** (00:33:21): Oh, I didn't know that. **Tristan de Montebello** (00:33:23): Yeah. The magic of games is short reps, immediate feedback, practice feedback, practice feedback. And it's enjoyable, you get rewarded, you get to adjust as you go. And what's changing is your internal feeling as you're going. So you're learning lessons, but you're internalizing. All of the practice is happening through speaking. **Lenny Rachitsky** (00:33:48): To reinforce what you just shared, I haven't shared this with you, but after I took the course, the mini course, I went to see my family in L.A. We visited for a few days, and I was talking about this course and just how fun it was and interesting and how much I learned from it. And I pulled up the games because I have access to the things online. I was just like, "Hey, you guys want to try this?" and we started playing some of these games that we're about to get into. And it was just, we spent like an hour just doing this and everyone loved it. **Tristan de Montebello** (00:34:15): Wow. **Lenny Rachitsky** (00:34:15): Everyone just felt so much better about their public speaking. Afterwards, my mom was like, "Hey, how do I do that on my own later?" **Lenny Rachitsky** (00:34:22): Wow, that's cool. **Tristan de Montebello** (00:34:23): My sister's like, "I want to start doing open mic nights because that was really fun just to talk." **Lenny Rachitsky** (00:34:27): Nice. **Tristan de Montebello** (00:34:28): So were you actually coaching them? How were you walking them through the different games? **Lenny Rachitsky** (00:34:34): We just pulled them up and played them. And then, I shared some of the tips that I learned in the class that we took, just like, "Try it this way" or "Try not to focus on being correct. Just focus on confidence and not leaking that you're not doing great." All these things we're going to talk about. Yeah. So it was a lot of fun. So let's get into some of these games. So we're going to try two or three. Which one do you want to start with? **Tristan de Montebello** (00:34:56): Conductor maybe. **Lenny Rachitsky** (00:34:57): Sweet. I love Conductor. That one was really insightful to me. **Tristan de Montebello** (00:35:00): Okay, so I've got Conductor. The way this game works is that when I click "start training," I'm going to have a random title that's going to appear. And for those of you who are just listening and not watching this, Lenny will say the title out loud so you can hear. And then, what you won't see or what you'll see if you're watching is in front of me, all I'm going to see are a series of random numbers. It's going to start with five, and five is just my natural rate of speaking like I'm speaking right now. But then, I might see a number from one to 10, and each one of these numbers represents an intensity or a state that I have to tap into. So if I see a seven, I automatically have to raise my voice and get into that kind of an energy. And if I see a 10, you could only imagine what that is. But it's also true for the lower ones. If suddenly I see a three, I have to find a way to calm my energy and match the three and go all the way down to one. **Lenny Rachitsky** (00:36:00): And then, there might be a slide that says "breathe," which is just an indication to pause. And when I see that slide "breathe," if I just go silent, that's because I'm in front of the breathe slide and I'm not allowed to speak. And in that moment, my goal is just to relax myself and calm myself and then see what happens where I'm at when that slide moves on to the next one. And now we're going to do this. This is going to be 70 seconds, so it's going to be super quick. Ready? **Lenny Rachitsky** (00:36:28): Yeah. So I'll read the title as soon as it pops up. **Tristan de Montebello** (00:36:31): Perfect. **Lenny Rachitsky** (00:36:33): "When I grow up." **Tristan de Montebello** (00:36:36): When I grow up, I want to have taken on all of my weaknesses or all of the emotional things that are holding me back. Because kind of annoying for me that I'm 40 years old and there's still things that are holding me back that man, I've had these when I was a kid. I was like this when I was 10. And it drives me crazy, because aren't I supposed to be an adult? Aren't I supposed to be mature and have my life together? I have two kids. I have this incredible responsibility. And I have to teach them, I have to show them the way. So I've decided I'm going to hire a coach, and I talked to him just a couple of days ago, so this is perfect timing because I want to unwrap, unravel, and untwine every single one of these emotional blockers so that when I grow up, I'm completely free. **Lenny Rachitsky** (00:37:45): That was so fun to watch. I'm seeing the numbers. If you're on YouTube, you can see what's going on there. If you're not, basically there's different numbers that give Tristan the different energies to be at, and that was masterful. **Tristan de Montebello** (00:37:56): I think we saw, what did we see? We saw a six. It went up first, six, seven, then it went down to three. Then we saw, I think a two, a one, then a breathe, and then it went back to a five. How about you give it a go and then we chat. **Lenny Rachitsky** (00:38:10): Let's do it. What do you think? **Tristan de Montebello** (00:38:11): Ladies and gentlemen, let's see this. Here we go. The title is The Greatest Puzzle. **Lenny Rachitsky** (00:38:19): The greatest puzzle that I think that I've had in my life, and I think just for most people, is trying to figure out what to do with their life. And I just had to spend so much time thinking... Actually, no, let me change. I'm changing direction. I actually have known from very early on what I wanted to do with my life. I've actually found it to be not much of a puzzle. I knew from pretty early that I wanted to be a software engineer. And interestingly, I became a software. And as I think about the puzzle that created around my life, I ended up... So my life actually started to look like a puzzle instead of what I'd always thought I'd be. So I ended up having a bunch of different careers. And I look back at my life and it started with one piece, and each piece led to all these other careers. Nailed it. **Tristan de Montebello** (00:39:33): It's funny. At the end you were like, you didn't even see there was a six that came up and then when you looked up, it had already gone away. That's a good warm-up. **Lenny Rachitsky** (00:39:42): Yeah, yeah. Let's do it. **Tristan de Montebello** (00:39:42): It's funny, because what it looked like to me is that, well, you just didn't let yourself play the game. You wanted to... You were more focused on, "I want to make sure this works well, this looks good, or I don't make a fool of myself" than "Let me just play the game." So switch your mindset from that. Back in the Creator Cohort, you didn't really care, because if you failed, it didn't matter. So you just played the game. And this is the same idea. Just don't try. Just let yourself play the game. **Lenny Rachitsky** (00:39:43): Okay. **Tristan de Montebello** (00:40:15): The game will do good. But that was actually really interesting. I feel kind of similar, which is cool, except I didn't know where it was going. But that feeling of all of these puzzle pieces, and suddenly when I hit Ultraspeaking, it's like, "Oh wow, every single... There's no more. There are no more gaps." That's really cool. Okay. **Lenny Rachitsky** (00:40:35): Here we go. **Tristan de Montebello** (00:40:36): You ready? **Lenny Rachitsky** (00:40:37): Ready. **Tristan de Montebello** (00:40:38): Here we go. "Integrating new cultures." **Lenny Rachitsky** (00:40:48): It's interesting having a kid. So we just had a kid about a year ago, he is a year and a half. And there's an interesting new experience where there's my family and their culture, there's my wife and her culture. And it was never a big deal for us, these different backgrounds that we have because we could do our own thing, we have our families, they're doing their thing. But now that we have a kid, I have to really think about this. I have to constantly wonder, "Is he getting both experiences? Is he being pushed in one direction or another? Is he going to get the full benefits of both of these cultures?" And I find if I don't actually think about it too deeply and just let him have fun and hang out with our different family members, he gets everything that I want him to get; that he experiences my wife's family's culture, my family's culture, and then the combination of my wife and I's new kind of culture and family that we're building. And so, I'm really excited about the future for us all. **Tristan de Montebello** (00:41:57): Yeah, that was awesome. **Lenny Rachitsky** (00:42:00): I'm practicing not leaking. All I think about is how much better it could have been, but now I'm leaking as I say that. See? **Tristan de Montebello** (00:42:01): Yeah. **Lenny Rachitsky** (00:42:01): It's hard. **Tristan de Montebello** (00:42:10): Yeah. You're hedging. **Lenny Rachitsky** (00:42:10): Hedging. **Tristan de Montebello** (00:42:13): So the point of all of these games is to create turbulence. This is going to be the theme of this podcast. I'm going to share only flight analogies. But if you think about a pilot, a flight simulator, you can think about these games as the flight simulator. You don't put a pilot in a flight simulator and waste those precious hours having them just cruise at 30,000 feet in clear skies. You're going to say, "Okay, you're going and now hey, you've lost your captain and you have to do something" or "Hey, your motor just broke" or "You're going into crazy turbulence." **Lenny Rachitsky** (00:42:46): So the gain here is always, every one of these games have in common that we're creating turbulence for you. So it's on purpose that like, "Ooh, that's interesting how I tend to want to leak, to want to break character. Wow. It's interesting how at the end, the ending strong is not just an automatic habit that I've built for myself." So what we want with the turbulence is that it highlights areas that we want to work on. And you can go again and see immediately because you have that same pressure every time. There's no way you can prepare for Conductor. You can do just a ton of reps and get to become the person who can just navigate the turbulence really, really gracefully. **Lenny Rachitsky** (00:43:29): Which reminds me of a Kevin Kelly quote that I love where he says, "Pros are just amateurs who've learned to recover gracefully from their mistakes." And this is what we're trying to do here. If you know that you can recover from any mistake gracefully, then you're going to have confidence in any speaking scenario. And most of the scenarios you're going to be in are spontaneous, are ones you can't prepare for. So it's that much more important. **Lenny Rachitsky** (00:43:57): So tell me, what do you remember from going through Conductor and the Creator Cohort, or specifically here, what was coming up and what were some of the things that pop into your mind? **Lenny Rachitsky** (00:44:10): There's two things that I really took away from it, and it's different doing it now on camera with this whole podcast thing. **Tristan de Montebello** (00:44:15): Yeah. **Lenny Rachitsky** (00:44:16): But the things that I really took away that have stuck with me from this exercise is one, is that you have this kind of metaphor of these file folders that you have kind of in your head where every energy level, like a one when you go low and a 10 or even a five, when you're at that energy level, you access different insights and memories and stories. So it's not just like, "Now I'm going to say the same thing at a 10, or I'm going to say the same thing at a one." It's when you let your body just slow down and relax to a one, new thoughts come up, because making it up as you go along and you're just trying to figure it out as you go. And that really happens when you're forced to go from five to, "Okay," and you let your body settle into a one. You're like, "Oh, okay, here's a new thought that comes to mind." So that was really powerful for me because I never had realized that. **Lenny Rachitsky** (00:45:12): And then, the other is just this idea of doing these really hard things with very low stakes. It's higher stakes, so maybe that's why it's different, how it feels different doing it here where it's like, "Oh, this is-" **Tristan de Montebello** (00:45:22): Yeah. Yeah, this is extremely high stakes for you. **Lenny Rachitsky** (00:45:26): Yeah, relatively. But yeah, there it's a couple people and you're like, just don't worry about failing so you don't even have to worry about apologizing or fleaking. It's just like, "Yeah, I did what I did." So those are two really powerful ones. I just like practicing this. And knowing you'll be okay at low stakes builds confidence. I'm like, "Okay." It's making up a minute of talk about the most random thing on the spot, not something that I would feel I'd want to do, but then you realize, "Okay, it's fine. I can do that." **Tristan de Montebello** (00:45:54): The common theme for me, and I've been on this journey for seven years now, I still am blown away every week by the lessons I've learned over the course of the seven years, which all come down to your brain, your subconscious is so incredibly powerful. So your hardware is magical. And because I've spent seven years kind of getting rid of the bad habits, getting rid of the gunk and trusting myself more, I allow myself to take many more risks. So I'm jumping into these games still with the same doubts in some sense, but they've just, everything's tapered down way, way, way into the background. So I get to be much more present. **Lenny Rachitsky** (00:46:43): And I talked about the summary prompts earlier in the podcast, saying the beginning of a sentence and trusting that your brain's going to fill in the gap is something that's initially hard to do. But when you've done it 1,000, 2,000, 10,000 times, you start believing, "Hey, maybe my brain will deliver every single time." So you can start saying the beginning of sentences the direction you want to go into and your brain fills in the gap, and we're going to do a game on that in a second. **Lenny Rachitsky** (00:47:12): But the Conductor one is so beautiful because the way we describe it, so that folder one when it came into my mind was my favorite ever. But the original one was when you tap into a certain energy, that creates emotion. And if you tap into that emotion, the words come as a natural consequence. So it's energy leads, emotions follow, and words fill in the gap. **Lenny Rachitsky** (00:47:44): And when you experience this for yourself, if you go into Conductor and you play, you realize, "Okay, if I want more conviction, I can raise my energy or get into a state of conviction and the words that are going to come out, the ideas, the stories, the anecdotes, the examples, everything is going to fit into that. If I feel frustrated, I can dive into that state and stay in that state, and naturally the content is going to follow. It's a very, very powerful game. It's a very exciting game, and it's a game that, especially when you're playing with low stakes, you very quickly feel the effect of, "Oh, I can see the potential of what it could be if I could just be like this anywhere." Maybe you taper out a little bit of the extremes. **Lenny Rachitsky** (00:48:42): But you can access this for free on Ultraspeaking or the way we did this at first, you just go to Google and type in a random series of nine numbers and then just have a friend say each number, one after the next, and you just match it. I used to just put my hand out and go up and down. So in essence, it's very, very simple to apply it. **Lenny Rachitsky** (00:49:03): And it's just like a lot of fun to just get an excuse to just go wild and high and then just get low. I love that part of it. And let's get into the next theme. But just one other insight I had that you shared with me when I did it the first time is just people have a strength. **Tristan de Montebello** (00:49:16): Yes. **Lenny Rachitsky** (00:49:16): They're either, correct me if I'm wrong, they're strong at the highs and just very uncomfortable at the lows or the opposite. And for me, I thought I was going to, "Oh, obviously I'll be more natural at the lows, because like introvert world." And you're like, "No, you're actually super energized at this high end, and then it's hard for you to access the low." And I thought that was really insightful for me. **Tristan de Montebello** (00:49:39): Yeah. You'll notice it pretty quickly once you jump in, especially with a friend. It's cool because when you get to see, "Oh, I'm much more comfortable going up than I am going down or vice versa, or I'm stuck in the middle and I am only comfortable when I'm not in the extremes." It's just telling you something. **Lenny Rachitsky** (00:49:59): This is what we want. We want to a mirror in front of us so I can know, "Okay, what's happening here?" I'm not very much a fan of actually watching yourself on camera on video, because again, this is an inner game, not an outer game. So when I watch myself on video, I see the outside, which can be useful for certain things, but the fundamentals are inside. So getting a mirror of I play this game and I feel a certain way, "Oh, interesting. It was easy to go up." So I can muster energy pretty quickly, and I'm willing to take risks of jumping into a different energy stage, which might mean changing the direction of where I'm going. **Lenny Rachitsky** (00:50:37): But slowing down means I need to be willing to take up space. I need to be willing to just be while everybody's looking at me and I'm using up their time. But I'm going to take up space and I'm going to take a moment to go inside and be introspective and really ask myself, "Okay, what do I want to say here?" And so, that's a reflection of, "Well, what does that mean if I struggle to do that?" And that's why speaking such an interesting skill set. **Lenny Rachitsky** (00:51:08): All right, let's do another game. **Tristan de Montebello** (00:51:10): This next game is called Triple Step. And Triple step is a game for people who struggle to stay on a single thought or get very easily put off their game or distracted. If you're the type of person where you're speaking and suddenly somebody yawns and you just start freaking out thinking, "I'm so boring and things are horrible, I must be terrible." Not, they probably have a baby and they didn't sleep last night. A pen drops and you start losing your ability to stay on track, this is a game for you. Also, a very fun one. **Lenny Rachitsky** (00:51:46): The principle of the game is pretty simple. Similarly to Conductor, we're going to start with a random speech title. So I have no idea what's going to show up. Then as I'm speaking, in this setting here, I'm going to speak for a minute. There will six random words or series of words that are going to pop up as I'm going through my speech. And my goal is to integrate the words into the speech as seamlessly as I can, as if they were part of the speech the whole time. So in theory, if I do a perfect job, if you're listening, you should struggle to pick out which words were actually the words that were popped up. The likelihood in one minute of me being able to do that is low, but let's see if you can do it. So if you're listening, you're not going to see the words. We'll tell you afterwards what they were. See if you can pick up on them. But otherwise, my goal is just to choose a strong direction and stay on that direction as naturally as I can. **Lenny Rachitsky** (00:52:43): Here we go. The title is, How Would Your Friends Describe You? I've been described as a Labrador by my friends. And I think the reason people describe me as a Labrador is because I am so easy to excite. It's like if you give me a box of french fries, I'm going to go nuts and it's going to be the best french fries I've ever tasted in my life. But if the next day I get a massage, I'll be completely in that experience and the massage is going to be the best massage. And then, I'm going to think, "I need to get a massage every day." I'm going to start daydreaming about massage as my natural day to day. **Lenny Rachitsky** (00:53:19): But the problem with being a Labrador is that Labradors get kind of excited. So I may be doing cartwheels one second, and the next second I'm supposed to be working. And so, I'll be on my computer, but then I hear the microwave ding and I think, "Oh, maybe I should go get some food next." And so, there's a beautiful trait to being the Labrador that allows me to explore all of what it's like to be human. I always have access to the internet inside me, but there are definitely some drawbacks as well. **Lenny Rachitsky** (00:53:50): Okay. So the words that you had to integrate are french fries, getting a massage, daydreaming, cartwheels, a microwave, and the internet. **Tristan de Montebello** (00:54:05): Yeah. And so, you might notice that some of the words I'm integrating literally, and some I might integrate more metaphorically like the internet of my mind. It's like I have access to the internet. So you can give yourself as much leeway as possible. The whole point here with Triple Step is you want to be that tree in the storm that is not so rigid that if the wind is too strong it's going to break in half, but not so flexible that it's going to swing every which direction as soon as there's a gust. So you want that firm solid grounding, which is in choosing a clear direction, that one thing off the bat, and then you want to make the words work for you. So stay focused on that one thing. And as the words come in, the more focused you are on that groove you've created for yourself, the easier it will be to let the words work for you. Okay? **Lenny Rachitsky** (00:55:03): And again, the skill this builds is to be more comfortable with things not going perfectly and being distracted. **Tristan de Montebello** (00:55:12): Yeah. I would say this one can be used for two other things. Number one is resiliency, right? Because this one will make your brain go crazy. And if you can stay composed within it, with all of these things happening, it really builds this ability to say, "Well, man, if I can do Triple Step on hard mode, I can do anything. Why would anything else scary? Why would an interview question scare me when I can throw these kinds of things? I can always navigate my way through." Right? We're trying to lower the likelihood of a mistake really hurting you. **Lenny Rachitsky** (00:55:48): And then, the other piece is this is a game, this one and a game called Rapid Fire Analogies, are games that are really, really nice to use as a way to warm your brain up. So you could use it before a podcast. You could use it before a job interview, before a meeting. When you want to be on, do a few reps of this, and your brain's just going to be completely lit up because it's pulling on so many different parts of your brain that are necessary for communication. **Lenny Rachitsky** (00:56:13): One last thought just before we dive into it. I think it's just to zoom out again, the reason that you've found this is a better way to learn to become better at public speaking, my sense is just if you were to just do the standard thing of just give more talks, find more opportunities to do presentations, it's too broad of a brush to build these different skills, and which you've identified is there's these very specific skills that add up to a great presenter. And these games pick a specific skill and help you just focus on that again and again and again. **Tristan de Montebello** (00:56:51): If you're already practicing, you're already leagues ahead of everyone, because most people aren't practicing. They're you're trying to learn from a video or a YouTube short or an article. You can only go so far with that. But if you are practicing, there are kind of two suboptimal ways that might show up. One is what you're saying. You're doing talks and you're speaking up more, but you're not really practicing. It's kind of, as you were saying, it's broad, broad strokes. **Lenny Rachitsky** (00:57:17): The other one is you are in a choreography, so it's like learning how to dance, but you only learn choreography. Well, that's all you know how to do. So if I ask you to do, I say, "Okay, now I'm going to put music on. Just dance." You're kind of stuck because you only know how to do the moves you were doing. So we're trying to get people outside of, "I have to be in my mind, or I have to do things that I've memorized how to do" and come back to trusting your natural ability to communicate. **Lenny Rachitsky** (00:57:51): So that's what we're doing here. You can feel like when you don't speak, when you struggle with speaking, you're stuck in this box, and everything around you is tiny and you can feel the sides of the box. And we're expanding the range. We're playing around with all kinds of different things, different tools. And all of them have specific meaning, but even if they didn't that much, you still would be able to, "Oh wow," you're pushing back the sides of the box. And now suddenly, "Hey, I can move around. I feel comfortable moving my arms and moving my legs and going to the right and the left and up and down." And just that act of making you feel more comfortable and more at ease is going to unlock your ability to communicate, because you already know how to do a lot of this. So we're tapping into these different skill sets and we're doing both at the same time. **Lenny Rachitsky** (00:58:42): **Tristan de Montebello** (00:59:43): Let's do this. **Lenny Rachitsky** (00:59:44): No, I'm not going to... I was going to say I'm going to nail it, but no, let's just have fun. Let's have fun. **Tristan de Montebello** (00:59:49): Yeah. **Lenny Rachitsky** (00:59:50): It goes how it goes. **Tristan de Montebello** (00:59:52): Indeed. Here we go. **Lenny Rachitsky** (00:59:53): Okay. And I'll say the title. The best thing about pain. So this is something I recently shared in another talk is just this quote that I always think of. **Lenny Rachitsky** (01:00:01): In another talk is just this quote that I always think of, "The cave you fear contains the treasure you seek," that the thing that is hardest often points you in the direction you want to go. Like I hate blue cheese, but sometimes I find that if I eat the blue cheese and add it to a salad, it ends up being the best salad I've had. Having kids is another amazing example where just kids are... There's so much pain, but it's also, there's nothing that is more joyous than having a kid. **Lenny Rachitsky** (01:00:29): And sometimes even growing a beard. I grow this beard and I have to maintain this beard for the rest of my life. And I know people would look at me without a beard and be like, "What the hell? Well, you look so different now and so young." Sometimes I think about just having a sibling and the pain that if I had a brother, if he just hit me, the pain that would come from that, but just then having the brother would be so much worth it, even if he's hitting me all this time. **Lenny Rachitsky** (01:00:58): And there, I ran out of time, but that was solid. **Tristan de Montebello** (01:01:04): Okay, I realize this is your first time playing Triple Step. It's kind of mean of me if you [inaudible 01:01:09]- **Lenny Rachitsky** (01:01:09): I have to go faster. **Tristan de Montebello** (01:01:10): ... Give you six words. So I'm going to give you four words. **Lenny Rachitsky** (01:01:12): Okay. Okay. **Tristan de Montebello** (01:01:13): But here's what I noticed. What I noticed is you were letting the word... The word was the beginning of a new thought. Right, so you say, "Another thing is beers. Another thing is...". So you're finishing your thought and then you're moving on to the next one. Try to hold onto one direction. The one direction is approach your fears head on. And then, so when you see a puzzle, it's like, look, this doesn't have to be a hard puzzle because now I know that if it's scary, I do it. And it's like having kids, which I thought was so scary, I just jumped in and now I'm moving forward. And so it's like I'm growing my beard without caring what other people think just because it might be scary, or maybe I cut my beard because that would be something scary. So you're holding onto the line. **Lenny Rachitsky** (01:02:08): With four, it's going to be a little bit easier to integrate them. Ready? **Lenny Rachitsky** (01:02:16): Let's do it. **Tristan de Montebello** (01:02:18): Social- **Lenny Rachitsky** (01:02:18): Social distancing. It's interesting that social distancing was such a thing that we all had to do for so long. And then all of a sudden we look back at that time we're like, "Was that actually necessary? Did we actually have to stay far from each other? Did that actually have any impact?". **Lenny Rachitsky** (01:02:34): There's all these things we have to learn, like sometimes we look at the stock market and we wonder, "Should I be paying attention to the stock market? Should I be distancing myself from it? Should I be investing more often? Should I be reading every newspaper that comes out every day to stay on top of what's happening in the world? Should I get closer to this information or should I distance myself? What's better for me?". And sometimes it feels like you're running this marathon where sometimes you go back and forth. Sometimes it's, "Let's all be together. Let's pay attention to all the news. Let's hang out." And it kind of feels like I just want to just want to go to the toilet and peace out. **Tristan de Montebello** (01:03:24): Amazing. That works. That's really good. **Lenny Rachitsky** (01:03:27): Okay. **Tristan de Montebello** (01:03:27): That's really good. Well, tell me what, because again, the games are meant to put you in a state of turbulence and find out what was easy, what was hard, what am I noticing? And now you know what you want to work on. If you did a rep and you got it and it went perfectly, then you're learning nothing. A really easy rep is not worth much. The only reps that are worth something are the ones where you feel an edge. **Lenny Rachitsky** (01:03:57): Yeah. And by the way, we should say the words right, that I had. **Tristan de Montebello** (01:04:00): Oh, yeah. The first one was the stock market, then a newspaper, which you brought in really, really well, then running a marathon, and then toilet. **Lenny Rachitsky** (01:04:13): Yeah. Okay, great. Yeah, just the fact that I'm okay doing this is a big milestone for me of just like, ah, whatever. Because before doing this thing I'm like, oh my God, I never want to sit there and come up with a talk for a minute on the most random subject, and there's a lot of power in just feeling comfortable just doing it, just like, sure, let's do it. Whatever. Something will come out that's interesting enough. **Tristan de Montebello** (01:04:35): That's why taking on this journey of speaking is so empowering because speaking is a high performance skill. So taking on a high performance skill, and starting to tackle it, and getting kind of good at it is very addictive. It feels really, really good. If you get good at tennis, if you get good at golf, if you get good at anything, product management, it's a addicting, it's exciting. And as soon as you get good, there's nuance to it, and it's energizing in and of itself. And because we have such awesome hardware as humans, we've been speaking all of our life, a lot of us have a pretty decent level to start out with. So you really quickly, you're getting to like, "Oh, I'm getting some results here. This actually feels good." So there's something really energizing about jumping into it. It's the thinking about doing the exercise that's scary, but as soon as you're in it, it's energizing and empowering. **Lenny Rachitsky** (01:05:35): And also just doing it, this is a very hard exercise. Just giving a made up talk for a minute with words you have to integrate, and concepts. And I think just doing that makes a regular talk so much easier also, because you don't have to do that. So there's something there about just doing it on hard mode, learning things, and then, oh, okay, I just have to talk about a thing that I already know about, that I have planned, much easier. Anything else around this game that is worth sharing before we do our final game? **Tristan de Montebello** (01:06:06): We have a whole series of games, and you could probably even invent other games, but some people will play Triple Step and will say, "Wow, that's so hard." And then they'll go and play Conductor and think, "Wow, this is my game. This is so easy." But other people will play Conductor and think it's impossible, and then come play Triple Step and they'll be like, "Man, this is my jam. I can get this one very, very easy." **Lenny Rachitsky** (01:06:31): So again, it's just a mirror of where you're at. And what's beautiful about this is you start playing around with these games, you're very, very quickly going to see, okay, this is my edge. And where your edge is, as you were saying with your quote, is often where the gold lies. So if you can spend some time there and learn what it is underneath the struggle, what's actually holding you back. When you unlock that, whatever's holding you back in Triple Step, or in Conductor, in any other game, is holding you back elsewhere in your life. So when you unlock it there, it kind of unlocks the other things, which is really nice, like a set of gears. **Lenny Rachitsky** (01:07:12): And it's interesting, as we were talking, where my mind keeps going is I just want to say how I didn't feel good about my performance, but I'm internalizing the lesson of don't leak how you feel. And that's a really powerful lesson. It's really hard not to just to be like, "Oh, that was not good." I really wanted to say that after every time I tried this and I am making myself not. And I imagine from your perspective you're like, "No, it's fine. It's like whatever." **Tristan de Montebello** (01:07:40): Yeah, absolutely. I was actually thinking, I bet a lot of people watching you do that would think, wow, I don't think I could do that. That would be their first thought. **Lenny Rachitsky** (01:07:49): So absolutely. And again, and this is a habit. And the noise doesn't completely disappear, but it goes down to being almost imperceptible. So what we're trying to do is we're trying to internalize all of these habits to the point where I don't need to consciously think about them. **Lenny Rachitsky** (01:08:12): So it's like a gymnast who's doing their tumbling routine and jumps into the air. As they're flipping, they're not consciously trying to think of how to do a flip. They've done it a thousand times. They know how to do a flip. The only thing they have that they may be thinking of, all of their attention is on being completely present to what's happening, relying on your body and your subconscious knowing what to do, is they have kind of like listeners, like in programming, keyboard listeners. You have something that's there that is just listening for anything out of the ordinary. And it's very, very fine-tuned. **Lenny Rachitsky** (01:08:47): So as I'm speaking, for example, I might think to myself, "Oh, I may be rambling right now. Maybe I'm going a little bit too long." And it's a little listener that's going to just gently, nicely, say, "Hey, warning, I don't know if you're aware of this." And as I hear that, I might say, "Oh, okay, let me wrap it up." Or maybe it's saying, "I'm not sure if you're being clear," or, "Can you be more precise here?". Whatever it is, it's just a gentle listener in the background. **Lenny Rachitsky** (01:09:15): So as you get into the habit of staying in character, and if you had an audience here, we could have asked them right away, "Well, how do you feel about this?". You probably would've gotten really good feedback, really positive, which would've kind of jarred that feeling of, wow, I didn't think I did it that good of a job. And people are saying, "Hey, I thought that was pretty good." So As you get that reinforcing pattern, the voice starts going down more and more. **Lenny Rachitsky** (01:09:43): Awesome. I need that voice to go down. That'd be great. **Tristan de Montebello** (01:09:46): [inaudible 01:09:46]. **Lenny Rachitsky** (01:09:46): Okay, let's do another game. **Tristan de Montebello** (01:09:48): Always does. **Lenny Rachitsky** (01:09:49): Cool. Let's do last game. Last one of these practical games. So this is actually a game from one of our courses that I'm pulling out. It's not a standalone game, it's one that's inside of the courses. But again, if you wanted to replicate this yourself, you can very easily do it. **Lenny Rachitsky** (01:10:09): So what we're going to do here is we're going to work on conviction prompts. So this comes back to this idea of entering a state or changing your energy to impact the words that are coming out of your mouth. So what's going to happen here, is similarly to Triple Step, I'm also going to get a random topic that I just have to start speaking about. But now, instead of getting a word that I have to integrate into my speech naturally, I'm going to get a prompt. So it's going to be the beginning of a sentence that I have to say out loud, and I have to find a way for my brain to just complete the sentence. And the sentences are specifically chosen because they're going to put you in a state of more conviction. So it's going to force me to care more about what I'm saying basically. **Lenny Rachitsky** (01:10:56): And this is a game for executive presence. If you think about somebody who you feel has great gravitas or great executive presence, they usually have, there's something about them that's saying, this person really believes in what they're saying. And what this game is showing you is that, hey, there's a way to fast track myself to that place. If I want to have more executive presence, let me bring a little bit more conviction to what I'm saying. **Lenny Rachitsky** (01:11:27): There's a caveat, small caveat. Maybe 10% of people in the workforce need the opposite. They need, "Hey, you need to maybe question what you're saying here." But the reality is the vast majority of people actually are not truly standing behind their words and their ideas. And what that does is that the people who speak a lot and feel a lot of conviction, their ideas go through more often than the others. And you'd want ideas to stand for themselves, but that's just not reality. So for most people listening to this, if you can bring more conviction to your words, then your ideas are going to have a better chance of being seen equally to those who are already doing that. So this is what this game's about. **Lenny Rachitsky** (01:12:14): Awesome. Okay. **Tristan de Montebello** (01:12:15): Okay, here we go. The title is Saying No. I've had to learn this the hard way as an entrepreneur, that saying no is one of the most important things I can do. But saying no is not saying no to a meeting, because that can be easy. And what I'm going to say now matters a ton. This is saying no to doing all of the exciting projects that I want to do. So as I said earlier, I'm Labrador. I get excited about everything, and I genuinely believe that every idea is awesome, but that doesn't mean I can do every idea. I need to choose a very clear focus and stick to that focus. **Lenny Rachitsky** (01:13:02): And this is a game changer. When you start reducing the amount of things you're doing to a painful amount, a painful few amount, then when you get there, suddenly everything else changed. And it astonishes me when I do that, just how much more I can get done, even though I'm doing fewer things. **Lenny Rachitsky** (01:13:22): I love it. That was great. These words are tough. **Tristan de Montebello** (01:13:27): They were, yeah. This was not an easy one. This was not a... Good thing that I get a tough one. Well deserved. **Lenny Rachitsky** (01:13:35): Let me read the phrases real quick, just so folks know. So the phrases you had to integrate is, "This matters a ton. I genuinely believe that every idea is awesome. Game changer." **Tristan de Montebello** (01:13:45): It was just, "I genuinely believe that." Yeah. **Lenny Rachitsky** (01:13:49): Oh, got it. Okay. "I generally believe that." And then, "game changer". And then, "It astonishes me when." **Tristan de Montebello** (01:13:55): And I'm so eager for you to go through this, and for anybody listening to try this for themselves, even if you know what's coming. Like, if you want to do this for yourself right now, write the words, the prompts that Lenny just shared, and choose any title, and just speak for a minute, and see if you can integrate those in. Because you're going to notice how if you bring conviction, these words naturally bring that out of you. And it's so interesting to watch the content change as a result of the state you get into and what you say. So it's really powerful to discover just how incredible your brain is. **Lenny Rachitsky** (01:14:36): So same intention for you I think, is choose a strong direction from the beginning. This is always, in speaking in general, the stronger the direction you choose in the beginning, the more ideas you're going to have. Everything gets easier when you choose a strong direction. **Lenny Rachitsky** (01:14:54): Okay, let's try it. **Tristan de Montebello** (01:14:55): But the goal here, is as it says, advocate for an important idea related to the speech title. Ready? **Lenny Rachitsky** (01:15:01): Yeah, let's do it. **Tristan de Montebello** (01:15:02): Here we go. **Lenny Rachitsky** (01:15:02): YOLO. **Tristan de Montebello** (01:15:06): The title is Space Exploration. **Lenny Rachitsky** (01:15:08): I think it's hard to imagine anything more important to the human race than space exploration. I know there's a lot of talk about people wasting time trying to get us to Mars, or trying to not think about what is happening on earth, but I feel like there's nothing more powerful, and important, and inspiring. In fact, the entire world needs to focus more on the value of space exploration. There's so many things we can discover, so many things that can help us on earth, and we cannot forget how much potential exists outside of our little earth, that we think our whole existence and everything that's ever existed on this one planet, when really we're this tiny, pale blue dot. And it just astonishes me when people don't think about this, don't think it matters, don't think they should spend any time getting us into space, investing money in space. And just hearing stories, if nothing else, of people that have gone into space and how life-changing that was for them, should tell us that space exploration is incredibly powerful and important. **Tristan de Montebello** (01:16:14): Yes, that was awesome. That was so cool. So you had, the title was Space Exploration, and the words were, "in fact", "the entire world", then, "We cannot forget that," then, "It astonishes me when," and finally "life changing". So what was that like? What did it feel like getting... **Lenny Rachitsky** (01:16:41): Yeah, there's a lot of... It really helps, just like, "Here's the thing you're going to believe." And I don't know if I got lucky with stuff, but it just felt like, okay, I have, something comes up that I'm not going to leak. But anyway, it was like, oh yeah, cool, something interesting happens. **Lenny Rachitsky** (01:16:57): And that's one of my other actual, just going on a little quick tangent, insights from the lessons that you guys teach, is that as you are forced to talk, you have new insights emerge. And you almost figure out what you think and know by being forced to get out of your head, and these problems help you along that. But I think that's really interesting, of just like, this will help you develop things, and insights, and take them out of your head. **Tristan de Montebello** (01:17:26): Yeah. Well, hopefully we get to talk about the Accordion Method, one of the most powerful methods I have, which is very close to this. **Lenny Rachitsky** (01:17:35): But this is often a prompt I tell people when they're speaking. I say, because people tend to get into a public speaking voice, so we'll be in a class, and they'll be chatting normally, and look super normal. And then we'll say, "Okay, now just a timer. I'm just going to give you a speech. Just speak for 60 seconds so we get a baseline." And I click play, and suddenly I say, "The important part about doing this," and they enter into a different version of themselves, a very professional version, whatever that would mean. It's so much more freeing, powerful, connecting, and effective to speak conversationally. **Lenny Rachitsky** (01:18:18): And so the cue I often give people is don't think about us, just think out loud. And that's really what we're doing. We can, most people have a skill set that's up here and a mindset that's down here. And so if you can just change the mindset to match the skill set, you've already made a giant leap. And you do that by reducing the stakes in your mind and by just speaking. And as you do that, when you're thinking out loud, you have these moments of connecting things in your mind, and then naturally it pops out. **Lenny Rachitsky** (01:18:59): And if you're doing it well... And I love, there's a really cool Naval Ravikant interview on the Joe Rogan Podcast from many years ago that's phenomenal. And at one point he talks about communication, if I'm not mistaken. I think it's on that podcast. But he says something along the lines of, "One should discover the words they are saying at the same time their audience is." And this comes back to thinking out loud, like if I'm really in my mind, I'm making connections, and suddenly the words are the consequence of it. **Lenny Rachitsky** (01:19:31): So using prompts, poking your brain, giving these cues naturally creates things that you couldn't have anticipated otherwise. It's like putting constraints on a creative project. **Lenny Rachitsky** (01:19:46): I love that. Before we segue to a couple of these methods, the Accordion Method is one example, I want to ask about, when people hear this, they may feel like you're helping people more, just like make shit up, and why, why would we want that? Talk about just how this isn't just like, you're not going to actually give talks like this necessarily. This is... And I guess I'm answering the question, but I'm curious if that's how you think about it. This is building a skill so that when you actually want to give a real talk that you've prepared, you are better at it. But yeah, just thoughts on just that potential element. **Tristan de Montebello** (01:20:23): Yeah, I think that's an important question, and it's a question I hear a lot because we all know a bullshitter, and that's the person who masters the skill of communication but doesn't have anything to show for it. **Lenny Rachitsky** (01:20:43): And so this thing happens, is that I see bullshitter and I think to myself, I really, really don't want to become that person. And what happens is it becomes an immune response or like an immune response where the desire not to be that person and the feeling being around that person gives you is so strong that now if I take even the smallest step in that direction of speaking freely, sharing my thoughts out loud, bringing more conviction or confidence to what I'm saying, not leaking, then there's this immediate response like an immune response in my body that's just too strong, that's saying, "Uh oh, you're becoming the bullshitter. Alarm bells. Alarm bells. Go back to that safe little corner you were in." **Lenny Rachitsky** (01:21:39): But the reality is, if you're thinking that, then you have no chance of becoming a bullshitter. Because if that thought is even popping into your mind, then you're the type of person who has developed a very acute skill set of noticing when people bullshit. And you have that same skill set for yourself. So it's just going to be, now it's just too loud. **Lenny Rachitsky** (01:22:05): So as we go through this practice, we want to match, "Hey, I want to match that bullshitter's level of communication, except I'm going to have the ideas to back it up. I'm going to really put effort into my craft, but I'm going to be able to show them in the best possible light." And what we want to be able to do is notice, okay, if this is a big thing for you, the bullshitting, and you're noticing a big reaction, just even listening to us, not even playing the games yourself, then you definitely benefit from calming that voice down. So spending time learning these skill sets, because you're most likely atrophied because you're staying away from it. And you're going to have this very powerful listener in the back of your mind that's going to ping you, and it's like, "Hey, you're at the limit right now. Stay true to what you know." And it's going to be a very good compass for yourself. It's going to be there and you can trust it because you developed this capacity. **Lenny Rachitsky** (01:23:02): Awesome. That's really helpful. **Lenny Rachitsky** (01:23:05): Okay. So, so far we've shared a bunch of techniques, things that you could just start doing today. We've done all these fun games that you could play online. If nothing else, just learning from the techniques these games teach you I think is really helpful. You've shared a bunch of principles of just like, here's how you actually get better at public speaking, and not this way, but that way. **Lenny Rachitsky** (01:23:27): I know you have a couple also methods just like that people can implement that helps them develop talks that I found really helpful. So maybe just as a closing, we talk about these two methods, the Accordion Method, and I think it's the Bow and Arrow Method? **Tristan de Montebello** (01:23:40): Uh-huh. **Lenny Rachitsky** (01:23:41): Awesome. Let's talk about the Accordion Method. We did this in the class briefly, and it was really helpful, and I've been explaining it to people of just like a really cool way of making your talk better. So talk about how that works and how people might be able to implement it when they're trying to develop the talk. **Tristan de Montebello** (01:23:55): Now, I'm biased when I'm going to say this, so take this with a pinch of salt, but I think the Accordion Method, the Accordion Method might be one of the things I'm the most proud of in my entire life because it's almost revolutionizing the way I think we should prepare speaking. **Lenny Rachitsky** (01:24:19): So up until now, we've talked about spontaneous speaking mostly, and that's going to be the vast majority of your speaking. Probably 80% of your speaking is stuff that you can't prepare for. But there are going to be situations where you know you have a deadline and you're going to have to speak. And either you have to speak because it's a job interview, or you're talking to your CEO, or maybe you're presenting to your whole team or an audience of a thousand. **Lenny Rachitsky** (01:24:45): The old way I think is shitty. I think it's broken, and I haven't found anything out there that is innovating on this. And it drove us crazy with Michael, and that's what gave birth to the Accordion Method. What's the old way? The old way is I have a talk coming up, so I'm going to dump all of my ideas on a piece of paper or multiple pieces of paper. Then I'm going to try rearranging those ideas. And as I'm rearranging the ideas and trying to make them in a talk, I have more inspiration. And I'm thinking, oh, maybe I could say it this way, and I don't want to lose that other thing that I said in the beginning because maybe I would use it. **Lenny Rachitsky** (01:25:22): And you start just creating this alien stack of paper with all of your ideas of what your talk might be, and then you're left with 10, 15 pieces of paper. And now as the deadline comes closer, what do you have to do? Well, you have to go through the excruciating pain of turning 10 pages into a script so that you don't forget all of those brilliant lines that you spent so many hours editing. And they're still in writing mode. They're not in your mind. **Lenny Rachitsky** (01:25:50): So now that I've created that script that I spent a lot of time editing, now I have to memorize it. And memorization is pretty. We're not good at memorization. Robots are good at memorization, humans are not. And memorization is like a chain where you just have all of these links very linearly. And everybody knows the feeling of going through, reciting a poem as a kid, and suddenly you miss one verse and you're lost, and now you're a deer in the headlights. **Lenny Rachitsky** (01:26:21): So what we're doing with the Accordion Method is instead of preparing our talk by writing, we're going to prepare our talk by speaking, and we're going to do so in a very specific way where we're going down the accordion to create extreme clarity, and to understand what the essence of our talk is, and then back up the accordion to bring back in intentionally just the right pieces. **Lenny Rachitsky** (01:26:48): So I was thinking of an analogy for this, and one that I really like is imagine you're redecorating your living room. The old way, the writing 10 pages and memorizing it is I'm going to look at my living room and I'm going to rearrange things and put stuff in a corner that I might need later. And then I'm going to bring some new things that I thought could be really nice and I'm going to struggle to make something work. **Lenny Rachitsky** (01:27:14): The Accordion Method is saying, and imagine this were easy to do with furniture, I'm going to take everything out of my living room except the most essential pieces that make my living room. So I might be left with that one couch that I really love, a pillow, a beautiful light that I bought three years ago, and one or two other small things. And as I look at that, I'm going to have clarity on the vision I want for my living room. And then very slowly, very intentionally, I'm going to go take certain elements that were already there that I might want to bring back in, and I'm going to bring new elements that now I see make sense. And so by the time you finish with your beautiful living room, it's going to be this beautiful minimalistic room that has a very clear design choice, and every element there is there because you chose it. It's there because you did it very intentionally. **Lenny Rachitsky** (01:28:15): So how does that work with the Accordion Method? What we do is you can go through the first step. If you want, you can write all of those ideas on paper just to get them out of your head. That's totally fine. But from this moment on, there's no more script. And I'm just going to give an example of times, but you can change these time constraints slightly. We're going down the accordion by using time constraints. So for example, you would say, "I'm going to speak for three minutes." So you're going to put a timer, and you have two rules. I have to stay in character the whole time and I have to end strong. So you must make it to the end of the three minutes, and it doesn't matter how bad it sounds, how many mistakes you make. The only point here is I'm trying to get my ideas out into spoken word. So I'm starting to populate my mind with everything and seeing where am I actually at. **Lenny Rachitsky** (01:29:13): Then after the three minutes, you think of, okay, what did I like, what didn't I like? Then you go to two minutes. And you put a timer and you do two minutes again. And you're very strict with those two minutes, because we're just trying to learn something every time. It doesn't need to be perfect. So at the two-minute mark, you do the same thing, but now you had to shave a whole minute out of that content. And as you do that, well, that means getting rid of the noise, getting rid of anything that doesn't feel right. **Lenny Rachitsky** (01:29:38): Then you go down to one minute. And you're going to go down all way to 30 seconds. So you started at a three-minute speech and you make your way down to 30 seconds. By the time you make it to 30 seconds, you're going to have only the essential pieces like that couch and that lamp in the living room. When you have the essential pieces, you're going to have a clear sense of what your talk is about, and it might've changed as you- **Tristan de Montebello** (01:30:00): Sense of what your talk is about and it might've changed as you were going down the accordion. And then from that place on, we're going to do another 30 second rep and then we're going to go back up the accordion. So you do another 30 seconds and then you do one minute, two minute, and all the way back up to three minute. And every step of the way you go from 30 seconds to a minute. Initially, a minute felt hard. Now that's double the time you just had. So you can bring in something that's aligned with the talk you want to share, and then two minutes, same. And then when you get to three minutes, one of my clients once said that it felt like he had a football field in his mind. So much space. And now whatever talk you have left there is a very clear, intentional talk. **Lenny Rachitsky** (01:30:45): And not only that, and this is why this is such an incredible method, your talk is now internalized. So you're at the stage of I've written a script that I've painfully edited in the old way that you now still have to memorize and it's a written speech that you're going to have to pretend to give in a spoken way. In this case you're there, but it's already completely internalized, not even memorized. It's internalized. You have these pillars, you know where you're going and by the time you make it through the accordion method, you're basically ready to go give it on stage. **Lenny Rachitsky** (01:31:22): But you could give it now in one minutes, two minutes, three minutes, five minutes. It's very plastic. You're going to be able to navigate different time frames. It's not going to really matter if you make a mistake because you're going to have a deep sense of what your speech is. It's not memorized, it's internalized. So not only have you gotten clarity and built out your speech in a very intentional way, but by the time you get to the end of it, you also actually know it and you're ready to perform it. **Lenny Rachitsky** (01:31:51): That example of the three minute when you come back up the accordion, that's exactly how it felt when I did this is just like, "Wow, so much time now" because you essentially, the way I think about it is you concentrate it to the best, most important nuggets and then you have time to build on those nuggets and you cut out all the stuff that no one really cares about, which is usually a long introduction, just like now just get to the good stuff and then you expand the good stuff. And it really worked for me and it was a really illuminating experience. **Lenny Rachitsky** (01:32:19): For someone that wants to actually use this. Say they have a speech coming up, say they're doing an all hands presentation in a week. Do you do this a week ahead of time? Do you do this a few days before? I guess where do you fit this in the workflow so that you actually remember what you want to say when it comes time? **Tristan de Montebello** (01:32:36): I can't say do it exactly a week or two weeks or it really depends how well familiar you are with the content. If you have an all hands, and this is something that you've been hashing with your executive team over the past two months, you probably know it really, really well and you have a lot of clarity and now it's just about organizing it nicely. So in that case, maybe you want to do a rough go through the accordion a week ahead of time so you have a clear sense of, "What is it that I want my audience to remember and what are the pillars that I know I like to hit that feel really good?" **Lenny Rachitsky** (01:33:15): So you can think about these as the foundational pillars that support that one thing that you're sharing or bookmarks that I know I have to hit and then what I would like to do. And so that's what I would write down. I wouldn't write a script. I'd write those down. And then before the all hands, maybe the day before, maybe even the morning of, depending on how important this is or how comfortable you feel, then you might go through just one or two reps of it, but now you already know it, so it should come back very, very quickly in your mind. **Lenny Rachitsky** (01:33:44): And it sounds like it's okay to have some bullet points at the end. It's hard for me to imagine going on stage with a bunch of people watching, not have any slide, bullet point, speaker notes. Any problems just having a couple of the bullet points of core points next to me? **Tristan de Montebello** (01:34:01): Before a talk, I might have four things written down. My one thing, and we'll talk about this in the bow and arrow, my one thing, the one thing I want people to remember and then the three bookmarks or pillars that I want to hit. And these are kind of cues or reminders that are going to send me into that part of the speech. So for example, if I'm talking about the accordion method, like what I just said, if I go back and I think through the pillars of this one. Well, my one thing would be the accordion method is more powerful than memorizing and then doing it the old way. **Lenny Rachitsky** (01:34:35): And then my bookmarks might be number one, describe the old way or the old way. Number two, the new way or the accordion method. And then number three might be internalize, don't memorize, and that'll be kind of the takeaway. **Lenny Rachitsky** (01:34:53): And if I have that in my mind, if I have 30 seconds, I can say the old way sucks because you have to work so hard and memorize everything and you're memorizing written stuff, the accordion method is much more powerful because you are going to compress it and go down and then open it up and then I'll explain that in a second and then I'll say, so you're internalized not memorized. What I realized right now is actually, it's funny enough though, those were the bookmarks there, so that sent me down that path. But actually I would say bookmark number two is probably the living room analogy. So it would be the old way sucks, the living room analogy, and then describe the accordion method. **Lenny Rachitsky** (01:35:36): That's cool. That was an awesome example of just the insights that appear by forcing yourself through this exercise. And it sounds like maybe the best use of this method is if you have a talk all of a sudden short term it's coming, all of a sudden you have to give a talk somewhere. There's a really powerful method to come up with a great talk that's maybe tomorrow, which you didn't expect. **Tristan de Montebello** (01:35:58): When I say I love this, I use this for myself, I use this with every single client I work with regardless of if it's a five-minute talk, a 20-minute keynote, we're using the accordion method, and you can use this at the macro level or at the micro level, so you can use it for the whole talk, but you can also say, "Hey, let's hone in on this part one that you're struggling with or part two and let's use the accordion to get clarity there." **Lenny Rachitsky** (01:36:26): So you can use the accordion as almost like a brainstorming way. I just want to see where I end up here and it takes maybe 15 minutes or something to go through a full accordion. It depends the time constraints you give yourself. Sometimes I'll just do two minute, one minute 30 seconds, that's even shorter, but I'll go through it for one piece of the puzzle or it's like, "Hey, we're almost there. Let's really internalize it. Let's clarify this. Let's get it really, really tight." And then I might say, "Okay, now let's do the whole thing through the accordion. So your 20-minute talk, I want to hear it in three minutes." That gets really, really interesting. **Lenny Rachitsky** (01:37:03): Amazing. Okay. Anything else along the accordion method before we talk about the final technique before we wrap up? **Tristan de Montebello** (01:37:10): We have a full self-paced course on ultra speaking on the accordion. I think it costs like 30 bucks or something like that to access all of the games and all the platforms. A bunch of them are free, but I think this one's behind the paywall. But we also put together a resource where we go all the way, we describe all of the accordion method, the bow and arrow, staying character ending strong on a free email course that we put together. That's ultraspeaking.com/Lenny. So this is shameless self-promotion, but if you want it to go grab it there, you can grab it there and then the bow and arrow is going to tie into the accordion method as well. **Lenny Rachitsky** (01:37:53): Awesome. I'm glad you mentioned all that and we'll point people to that URL in the show notes. Okay, final topic is the bow and arrow technique. Let's talk about what that is and how folks can use that to give better talks. **Tristan de Montebello** (01:38:05): The bow and arrow starts with a, it's really a mindset shift that most of us are in the weeds, so we're very sensitive and familiar to all of the content that we're working on. If you're in data, then you have all of the data. If you're sharing ideas, you still have all of the ideas. And the mistake that most people do when they're preparing a talk, a presentation, an all hands a meeting, whatever it is we tend to focus more on what we want to say than what we want our audience to remember. So the mindset shift here is stop focusing as much on what you want to say and focus more on what you want your audience to remember. **Lenny Rachitsky** (01:38:51): What we found out is if you think about your last all hands, the last big meeting, the last talk you saw on YouTube or in person, you probably don't remember much. In fact, I wager you might only remember one thing from that talk. And that's what this is all based on. We call it the bow and arrow technique because we think you can only remember one thing out of a talk and that it's very powerful to go through that framework or that kind of thinking when you're building a talk. And the one thing is your arrow. And so when you have that one thing to me I say it's literally a single sentence that is the only sentence people would remember if they left your talk. Would you be satisfied with that sentence? **Lenny Rachitsky** (01:39:37): It takes some times to get to a good one, but if you have a good one, it unlocks everything. It's like you're having a north star or a compass in your pocket. You can always pull it out. You always know where you're going. It gives you a lot of clarity. It's also giving a lot of clarity to your audience obviously. **Lenny Rachitsky** (01:39:54): But you can't just throw an arrow at somebody's face. You need to notch it in the bow and pull the bow back. And so to pull the bow back, you need to add in weight to that sentence. And that often comes in the form of an interesting anecdote or a data point that's going to support that or a story that's going to add emotion or illustrate it. So you want to find ways in which you can give weight or pull back the bow so that your arrow has that much more impact. So usually the process of clarifying what your arrow is is a back and forth between the bow and the arrows. So if you're going down the accordion method after the first one you might write or before the first one, you might write a tentative arrow, "Here's my one thing", and then the next one you say, "Okay, actually my one thing might be a refined version of that." **Lenny Rachitsky** (01:40:55): And so you might rewrite it a little bit and then you might tentatively put in what you think the bow is. "I like the anecdote I used here. I like this data point that I thought was powerful and maybe I can end on this story or this call to action." Then you'll put that in and then you go back in and you give that a try and that's starting to simplify in your mind. **Lenny Rachitsky** (01:41:17): And as you go, usually one informs the other. By the time you finish the accordion for example, you should have a very clear arrow and those clear bookmarks, which is the bow. But really the thing to remember with the bow and arrow, if you can only remember one thing, is switch your mindset from what I want to say to what I want people to remember and limit whatever that is you want them to remember as much as possible and that's going to give you extreme clarity. **Lenny Rachitsky** (01:41:48): That is really helpful. I'm preparing my talk for the summit, and so I'm going to use both of these exercises and what I take away from this last piece is as much as you may want to say a lot of things, really all someone's going to remember, as you said is one thing, if anything, but hopefully they remember that one thing. **Lenny Rachitsky** (01:42:06): So it's essentially what's the one thing you want people to remember and then what are the pieces of support that will convince them that that's right and that's something that'll stick with them? **Tristan de Montebello** (01:42:16): Exactly. And again, similar to the accordion method, this works in the macro and the micro. So if you have a talk where you're using slides, use it for the whole talk. But then for every single slide, ask yourself what is my one thing? And you might have some support there as well, but if you don't have a one thing for each slide, either the slide shouldn't exist or it should be multiple slides. **Lenny Rachitsky** (01:42:45): The symptom of not having a one thing is usually having a slide that says way too many things. I don't know what data point I want you to remember, so I'm going to put all of it on that slide. I'm not sure which piece of information is more important. So I'm going to write down all of my thoughts and I'm going to go through all of them or hope that you go through all of them and extract what you think is interesting. But the reality is people are just going to zone out if you do that. So if you do that slide by slide, you're going to gain incredible clarity and again, you're going to need less preparation and less memorization. **Lenny Rachitsky** (01:43:21): And to build on that, a pro-tip is to make that title of that slide exactly that one thing you want them to take away. Just put it there and tell them exactly what you want them to learn. **Tristan de Montebello** (01:43:31): Yes. I love that. **Lenny Rachitsky** (01:43:32): Sweet. Tristan, we've been on a journey. This was a really unique experimental episode. I had a good time even though I did some hard things, you made me do hard things that are good for me. Is there anything else you want to share before we get to our very exciting lightning round? Is there anything else you want to leave listeners with or a nugget you want to? **Tristan de Montebello** (01:43:50): I hope people found value. I mean, we did. This was really a group effort and I really appreciate you working on the agenda, really bringing in the games and trying to make this as practical as possible. I think the only thing I want to leave people with is again, this idea of how transformational tackling speaking can be, and the more constrained you feel with your speaking, the more transformational it will be to your life. So I just want to give this encouragement. It's much, much, much more enjoyable than you think it will be. It can actually be exhilarating and energizing and you feel like you can take over the world once you're on this journey. It's beautiful. And so I just encourage everybody, take the first step and start practicing your speaking. **Lenny Rachitsky** (01:44:45): Awesome. And I definitely felt that after doing the workshop of just I feel energized, I want to just talk all time, but then I'm like, I need more work. I need more practice. Tristan, with that, we've reached our very exciting lightning round. Are you ready? **Tristan de Montebello** (01:45:01): Let's do this lightning round. Here we go. **Lenny Rachitsky** (01:45:04): Here we go. First question, what are two or three books that you have recommended most to other people? **Tristan de Montebello** (01:45:10): I was given a book by my first coach, Nathan Seward seven years ago called The Big Leap by Gay Hendricks that I've recommended so many times. And it's based on this idea that we tend to self-sabotage ourselves when we experience too much success or too much happiness. And that that's linked to I think five things that would happen to us when we're growing up. One of them is the... What is it, the wild poppy syndrome or something like that. Like the tallest poppy is the one that's cut first. So if you shine in a family of siblings, then anytime you shine too much we're going to say, "Hey, hey, hey, that's not cool for the others." So that's going to be internalized and hardwired in your body and as an adult, as soon as you start shining a little bit too much, you're going to do the same thing to yourself. So the idea is going from having this point above which you can't be happy to turning it into, he calls it an upward-facing spiral with no upper limit. It's a really exciting and empowering book. **Lenny Rachitsky** (01:46:20): Do you have a favorite recent movie or TV show you really enjoyed? **Tristan de Montebello** (01:46:23): I haven't watched much very recently, but I'll say one of my favorite TV shows of all time is the Peaky Blinders, English show with Cillian Murphy. I'm absolutely obsessed with that movie that show. I think it's a true masterpiece. And I've recently rewatched, so I'll qualify this as recent. I recently rewatched The Nice Guys with Ryan Gosling and Russell Crowe, and I think it's just a brilliant comedy. Brilliant. Another masterpiece, I thought. **Lenny Rachitsky** (01:46:58): Do you have a favorite recent product that you have discovered that you really love. Could be an app, it could be something physical. **Tristan de Montebello** (01:47:05): I have a physical product actually right in front of me that was gifted to me by my business partner Michael Gendler, co-founder of Ultraspeaking. This is called an Ember Mug, and this keeps whatever you have in it, warm and it's extraordinary, whether you are a coffee drinker or a tea drinker, you know the feeling of pouring this and sipping it and by the fifth sip, it's cold. This keeps it at whatever temperature you want it to for however long you want. And I absolutely love it. I've been using it basically every day. **Lenny Rachitsky** (01:47:37): I have one of those. I find myself, you could actually control it through the app. You can control the temperature through an app, which I love. I haven't been using mine, but I love the idea. I know a lot of friends love them. Two more questions. Do you have a favorite life motto that you often come back to, share with friends or family, find useful in work or in life? **Tristan de Montebello** (01:47:56): I think we are too future focused as a species or as a society and as a result, we're always looking for the next thing. So the motto I share with my friends and my business partners and my family the most I think is these are the good old days. And I remind myself, I'll tell you right now for you and for whoever's listening. I mean think about the podcast, it's never going to be this young, it's never going to feel like it feels right now. And it always feels like these things are eternal, but truly one day you're going to look back and you're think, "Man, those were really the good old days." And so I say it right now, enjoy because these are the good old days. **Lenny Rachitsky** (01:48:40): I love that. And it's so relevant with a young kid, you're always going to think about, "Oh, they're little." I love that. Final question. You were the fastest person to reach the finals of the world championship of public speaking. I imagine that was quite a journey. I'm curious if there's a story from that experience that comes to mind that's like a wild part of that journey or something that might surprise people. **Tristan de Montebello** (01:49:09): Well, the journey lasted almost seven months, and it was the craziest journey of my life. I went into that with no experience whatsoever speaking, so really just a random amateur, and I just climbed the ladder by outworking everybody. The story that came to mind right away was six days before the semifinals. So I'm six days before the semifinals and I've qualified for the semifinals two and a half months ago. So I'm nobody, now I'm going to the semifinals of the world championships of public speaking. So my mind really is struggling to compute, and I had finally unlocked a speech that I thought was worthy of giving on the final stage. You have to show up there for the semifinals with one speech, and then the next day, if ever you win, you're going to the finals and you have to have a brand new speech, a completely different speech that you're going to give on that stage. **Lenny Rachitsky** (01:50:12): So you need two speeches ready to go, and both of those speeches have to be in theory, world-class. I'm six days before. I was struggling at that, really, really struggling to get that speech together. I finally got something and Michael managed to get me. I was flying I think two days later to Vancouver for the semis, and Michael managed to unlock this one opportunity to speak in front of 50 people to give it a try. And so I ran there. I give the speech, and as usual, we film. I film every single speech. I gave more than a hundred speeches over seven months, and I filmed every single speech. And we'd get home, we'd ask everybody for feedback, and I get home and I'm thinking, "Man, something is wrong. Something is wrong." I was so pumped. I wept. I genuinely wept as I wrote the speech because it was so moving. It was all about my life. It was something that I was so connected to. I don't know, probably the emotion of the pressure as well, but that's how much I believed in that speech. **Lenny Rachitsky** (01:51:14): We get home, we put the speech on the computer, and as I get to the most important part of the speech, I see two things happen. So this is the moment where I'm expecting people to pull out their tissues. One person pulls up the agenda for the event that they're at and is starting to look at the agenda. Another person pulls out their phone, another person starts going through their purse, and I'm looking at this, and suddenly I realized, "Oh, this speech, nobody cares about this. This is not a good speech. This is terrible." And then I go through all of these feedbacks. **Lenny Rachitsky** (01:51:53): I have 50 pieces of feedback, and all I'm getting is, "Good luck for the semi-finals. It's going to go great. I thought it was good", and I'm like, "I'm going to humiliate myself. This is terrible." So I had waves of anxiety. I threw my speech away, and in five days from the ground up, I rebuilt a completely new speech that was basically the best of everything I'd explored, everything I'd experimented with over the course of the three months leading up to that, the jokes that worked the best, like a stand-up comic would. I built my special and I focused on different areas like all of the transitions. **Lenny Rachitsky** (01:52:38): And right before the semi-finals, I gave the speech to one person. I was in Vancouver trying to internalize my speech and memorizing it in a plaza where I delimited the size of the stage and I'm just giving my speech out loud to get over the nerves, so I'm ready for the pressure to see if my brain will remember it and everything. **Lenny Rachitsky** (01:53:01): Anyways, I gave it in front of one person who was our district director at Toastmasters, and this is a speech meant for 500 to a thousand people, not one person. So I was scared it would flop. But in the middle of the speech, which is a completely different one, I saw a tear roll down her cheek, and then she just hugged me and said, "You got it. You did it. You did it." I walked out on that stage and I made it, and I won the semi-finals with that speech. **Lenny Rachitsky** (01:53:32): I think to me, that was really the, it showed me that everything I'd done was worth something, that it actually worked. If I was able to build a speech in five days, that could get me a win at the semi-finals of the world championships. That was kind of the ultimate, "Wow, I won." So when I walked into the finals, to me, I felt like I had already won. **Lenny Rachitsky** (01:53:57): Wow, that is a story. What an arc. Amazing. I'm so happy you asked that question. Now I just want to watch that speech and I want to learn more about this whole championship of public speaking, which I have no insight into. That could be its own podcast interview. **Lenny Rachitsky** (01:54:13): But Tristan, thank you so much for being here. This was incredible. One of the most interesting episodes I've done. Two final questions. Where can folks learn more about Ultraspeaking? I know you built a page where they could experiment with some of this stuff, so share that. And then how can listeners be useful to you? **Tristan de Montebello** (01:54:28): If you go to ultraspeaking. com/Lenny, so ultra like U-L-T-R-A ultraspeaking.com/Lenny, we put together, you have five emails that go deep into a bunch of the things that we've talked here. You can also just go to Ultraspeaking.com where you'll get access to a bunch of the games for free, and you can check out everything else that we do. If you want to follow me or hit me up or ask me questions about this podcast, you can do that on Twitter @Montebello, M-O-N-T-E-B-E-L-L-O. And how can listeners be useful to me? Well, first of all, if you made it to here, then I really appreciate you. Thank you. Thank you for being here with us, and what I would love for you to do is to apply this. We said in the beginning, you can't get better at speaking without speaking, and another piece of that puzzle is you want to do the thing that you're trying to get better at. So if you're nervous speaking in front of people, you want to speak in front of people as part of your practice. So the way you could be useful to me is introduce these games to somebody else. Try them for yourself, practice them with somebody else. Go through the accordion method with a friend. Try conductor, and when you succeed and when you have an awesome experience, then you can tell the world that Ultraspeaking helped you do that, and that would be huge. **Lenny Rachitsky** (01:55:56): Awesome. Tristan, thank you so much for being here. **Tristan de Montebello** (01:56:01): Thanks, Lenny. It was an honor. **Lenny Rachitsky** (01:56:03): It was my honor, Tristan. Bye everyone. **Lenny Rachitsky** (01:56:05): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at LennysPodcast.com. See you in the next episode. --- ## [4/17] Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) **Anneka Gupta** (00:00:00): When people say, "I want someone that's strategic," what they're really saying is, "I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product." So that's number one. And the second piece is, "I want someone that's going to champion and be a change agent to do things that may be hard but actually best for the long-term interest of the product or company, even though those things are not going to be easy to execute on." And I think if you have one without the other, ultimately people are not going to see you as strategic. **Lenny Rachitsky** (00:00:40): Today my guest is Anneka Gupta. Anneka is Chief Product Officer at Rubrik, a lecturer on product management at Stanford University's Graduate School of Business and on the board of Tinuiti. Previously, she was President, GM, and head of product at LiveRamp, where she spent 11 years and joined as one of their earliest employees. A bunch of former guests recommended Anneka Come on this podcast and you'll soon see why. **Anneka Gupta** (00:01:51): Thanks for having me. **Lenny Rachitsky** (00:01:52): So, I want to start with a question that I've started to ask guests that come on the podcast that have had extraordinarily successful careers and also just consistently successful careers. So here's the question. What do you believe are one or two skills or mindsets or habits that you think most contributed to your success that you think might be helpful for other people to learn and build to help them have more successful careers? **Anneka Gupta** (00:02:18): So it's funny, before we kicked this off, you talked about the post-it that you have on your computer that says have fun. My one mindset that I really have leaned into after someone actually gave me advice on this is to figure out how to have fun in my job, even in the most difficult of times. The reason why I say that is because when you're hit with really hard times, it's easy to operate from a mindset of scarcity and to look at everything as an unachievable hurdle to overcome. And when I was able to switch my mindset and say, "Well, I'm actually going to figure out a way to have fun with this," it actually changed my entire for how to deal with super difficult situations. **Anneka Gupta** (00:03:03): This advice specifically came up to me when I had a scenario where I had to essentially change out all of my direct reports in very short order, and I figured that out. It was a super daunting situation. I didn't know how I was going to manage and at first I felt so scared by what was ahead of me and how much change I was going to have to go through in a very short period of time. But when I got this advice, I started to try to reframe my thinking and it actually really made it so that I was able to get through that hard time and opened my mind up to so many more opportunities. So, now I try to embody that in every situation that I come across where I'm faced with something super, super challenging. **Lenny Rachitsky** (00:03:45): I love this advice. It's something that I've recently seen also in public speaking. If you can just reframe your thinking from "I'm scared of this" to "This is going to be fun. I'm going to have so much fun doing this. It's going to be like this energy and anxiety I'm feeling is me feeling like it's going to be a lot of fun." So, spending a little more time here, how do you actually do this? So in this case, you shared an example of basically you have to fire a bunch of people, not something one can quickly think about how to have fun with that. How did you do this? Is it just in your mind you're like, "I'm going to have fun with this," or is there something tactically people can do to make something fun? **Anneka Gupta** (00:04:18): I think there were a couple of things that I did and I've continued to do. One is figure out and really look at the situation and ask myself, what can I learn from this situation? What can I get out of this that's a positive outcome even though it is incredibly challenging to be facing it right now? So that's one thing that I've done. The second thing I think that has been really helpful is in going into meetings or other situations where I was trying to figure out how to collectively solve some big challenge, figuring out how to bring humor into the meeting. Just starting it on a light note and that elevated my own mood and way I was approaching the meeting, but also adds a level of levity to the situation for other people as well, which I think as a leader is super important because it's not just about your own mindset, but how are you transferring that mindset to the people that you're working with and the people that are working for you. **Lenny Rachitsky** (00:05:12): Got it. So part of it is just like, "How do I add a little humor?" Part of it is just thinking, "How do I make this fun?" Is part of this just like this is not as important as people make it out to be and we could just have a little fun with this thing. It doesn't have to be like we're not curing cancer. **Anneka Gupta** (00:05:28): Yeah, definitely I think that helps. Reflecting on this too, I feel like a lot of it comes down to the amount of emotional and mental energy I can bring to solving a problem. And there's always so much going on in life, like personal life as well as professional life, trying to figure out how can I architect my day and time to maximize my energy and be able to bring my full self to work and to these difficult so that I can have that mindset to look at things more broadly versus operating from a place of scarcity. That may come down to simple things like making sure that I have lunch. Sometimes when things get so busy you're like, "Oh, I'm just going to grab a protein bar and I'm going to skip lunch." But I found that that really decreases my energy. Or, trying to do things that are really difficult late in the day. Five to 6:00 PM is my worst time of day and I know that about myself, so I'm not going to schedule in my most difficult meeting or writing up a strategy deck or something for that period of time because I know that that's not going to be my best and it's actually going to make it more difficult for me to get the work done. Being able to manage my energy levels and figuring out how to schedule my time for my energy has really allowed me also to figure out how to have that abundant mindset in all situations. **Lenny Rachitsky** (00:06:50): **Anneka Gupta** (00:09:33): Well, first of all, I think Paul Graham did an amazing thing by putting a name to something so many of us have seen in practice. And while he didn't in his article say this is exactly what this is, I think many, many people that I talked to were like, "Oh yeah, I recognize this." I recognize people that I've worked for, CEOs, that have done founder mode, great founders that have done founder mode poorly. And it opened up a level of discussion that I think is really valuable for everyone to be having, whether you're a founder or you're someone that works for a founder. **Lenny Rachitsky** (00:10:04): Okay, so I'm going to ask two questions around this. One is from the perspective of working for a founder and founder mode, the other is being a product leader in founder mode. So, first of all, imagine you've worked with a few founders that operate in founder mode. As a CPO, as head of product, that's often a difficult place to be between the founder and the team that are building the thing. What have you learned about how to effectively work as a product leader with a founder in founder mode? **Anneka Gupta** (00:10:30): So, I think when a founder's in founder mode and if they're doing it well, what they're doing is really deeply understanding the business and then figuring out when to use their power as a founder to either tweak things and send something in a slightly different direction or fundamentally innovate and completely change directions or completely innovate in a totally new area. Now I think the way to use that effectively as a head of product is to recognize that they have that power to figure out how to use that power to get the things done that you know are best for the company. So, I always think about I have all the people around me. Whether they're people on my team, my peers, or my CEO, these are different resources I have to go get a initiative done or get work done in the company. **Anneka Gupta** (00:11:23): And as having a founder that can effectively operate in founder mode means that I can go and have a conversation with the CEO and say, "Hey, look, we have this huge opportunity and these are the things that aren't working, and I need your help to help figure out how we can move the needle more substantially in the direction that we need to go." And so activating that founder, that CEO to really be able to push the initiative that I think is best by making them an ally in doing so. I think one aspect. The second aspect is, which often happens, it's very difficult for many people and I've had this happen to me many times, is when a founder is like, "Well, I have this idea," and then you may or may not agree that that's the best direction to go in and how do you navigate that kind of situation? **Anneka Gupta** (00:12:10): So, one is actually taking a step back and objectively saying, "Well, why are they pushing this?" Maybe it's the wrong mechanism to go actually get done a strategy that's quite important for the company. So having a really deep understanding about why are they asking this, what are they ultimately trying to get at and what is the objective that they're trying to get at and is this the right way to get at it? If the answer is no to that, then you can go have a conversation. If you know what the objective is, you can go have a conversation with that founder and say, "Hey, look, I know this is what you're trying to do, but maybe instead of looking at option A here of how we go about tackling this, we should have explored these three other options instead." And that can help you and help navigate that conversation. **Anneka Gupta** (00:12:53): Now sometimes it's difficult to even get to that kind of understanding of the objective because someone might be just super set in their ways of, "Hey, I really want to go after this opportunity. It's my pet project." Then you have to decide as a head of product, do I really want to fight this or do I just give in on this, let it go? And also make sure that we get the stuff done that's most important to the company. You have to make that judgment call as a head of product and decide what is really going to make or break the company. What's the hill that I'm going to die on and is this something that I can shift or is this something that is not worth shifting? Of course it comes down to the personality. I've been very fortunate that I've actually had very few of those situations where the founder has been like, "Hey, I really want to go in this direction and I haven't agreed, at least with what we're trying to go after, regardless of the mechanism behind it." **Lenny Rachitsky** (00:13:47): I really love the point you made, especially about how the founder could be this lever to get things done. When you identify something needs to change, the best way to change that is just have the founder go in there, tell everyone, "Hey, we're going to do this thing differently." It's such like a positive spin on how to leverage founder mode where a founder actually has a lot of power to change that other people in the company don't. Okay, so let's go from the other side. So, I was talking to Nikhyl Singhal who runs the Skip, which is a community you're part of about you. And he said that you're a leader who excels in founder mode, that you operate in founder mode a lot. And so as a product leader, what have you learned about just how to think in founder mode, operate in founder mode, leverage that approach to leading teams, leading product teams? **Anneka Gupta** (00:14:32): Yeah, I think it's often easy as a leader to say, "I'm not going to roll up my sleeves and get into the details of the business or ask a lot of detailed questions about the business because you want to empower people and make them successful." What I've found is that understanding the details of the business and asking questions and understanding to the utmost extent you can, what's working, what's not, what are the financial goals of the business? Are we on track to get there? How are we making decisions? Getting into that level of depth is super important, and then you can decide as a leader, what do you want to do with that information? So there's a lot of information that I collect about what's happening in the organization, the decisions that we're making that I don't do anything with at a point in time. **Anneka Gupta** (00:15:20): That's my choice to make, but I want the information because in understanding the depth and what is happening, I can decide where I actually think I need to go in deep and make either very significant course correction or a small course correction. Then the way that I think about how do I bring my team along for that so they don't feel like I'm coming in and stomping all over the work that they're doing or trying to re-adjudicate a decision, one, is how do I get in there early? **Anneka Gupta** (00:15:51): One of the tactics I use is I ask people to present their strategies for things that I think we may need to do a course correction on, and I have them come in and then I ask them questions and then I make suggestion. And I'm able to do that in a forum where it doesn't feel like I'm coming in and rewriting the entire strategy, but I'm giving them there an opportunity to present their best thinking and then trying to figure out how do I take that and make that better and make them feel like I'm making it better versus stomping all over and dismissing the work that they've done. **Anneka Gupta** (00:16:23): I pick a strategic set of areas. So I think about what is most important for the business? What's going to kill the business if we don't get right and what are the biggest opportunities for the business that we need to go after regardless of how difficult it is for us to actually execute on that? By doing that, then at least I have clarity in my mind and I can provide clarity to the team about what is most important and rally the troops around making that stuff happen if that is what is essentially right. And I'll have all the context because I've asked all the questions of why this is right for the business, why is this going to help us with increased margins or get better growth or get into a new persona if that's what we're trying to do as an overall organization. **Lenny Rachitsky** (00:17:04): So in that example, and I love this tactic, you have your team come in, you ask them, "Tell me what the strategy is for this thing that you're working on." What you've seen work is instead of like, "No, this is broken, this is wrong, this isn't going to work." Your approach is ask questions and hope that they see the flaws or gaps. Is that how- **Anneka Gupta** (00:17:24): Yeah, it's ask questions, but you can't always lead someone somewhere with asking questions. It's also sharing a hypothesis. So I might have a particular hypothesis about the business where I might see something like, "Well, I was talking to security leaders in our customer advisory board recently and I heard this piece of feedback and this is what it made me think about our strategy, what do you think about that?" And then let them say like, "Okay, yeah, actually I see this or maybe I have some follow up questions." **Anneka Gupta** (00:17:54): It actually opens a whole discussion where I'm still able to provide my perspective and point of view but not completely shut down the discussion. Because what I always worry about is a leader is I'm going to come in and say something, and because I'm one of the more senior people in the room, no one is going to say if they have a concern. And the reality is I'm not always right far from it, but I want to be able to seed an assumption and then have a discussion based on that and then figure out what the right outcome is about what we should do next based on that discussion. **Lenny Rachitsky** (00:18:27): Speaking of strategy, you shared with me that at one point in your career you got this feedback that you just weren't strategic enough and that that comment led you to research and dig into what does it mean to be strategic, and also just to level up your strategic mindset and the way you think about strategy. What did you end up with recognizing as being strategic? What is that in your work and in your research? And then how did you actually get better at this work of being strategic? **Anneka Gupta** (00:18:57): I got this feedback once in a performance review and then I actually got it as well a few years ago when I was interviewing for head of product roles and I thought I had made a lot of progress on it, but when I reflected back, I think it actually all came back to the same themes. Which was I think when people say "I want someone that's strategic," what they're really saying is "I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product." So that's number one. The second piece is, "I want someone that's going to champion and be a change agent to do things that may be hard but actually best for the long-term interest of the product or company, even though those things are not going to be easy to execute on." **Anneka Gupta** (00:19:45): And I think if you have one without the other, ultimately people are not going to see you as strategic. If you're really good at articulating the why, but you're only bringing small ideas to the table, then that's not strategic. If you're championing big ideas but you can't articulate the why behind them in a compelling and simple way, then you're not going to be seen as strategic either. So, that's the formula that I've come up with. This is what it means. And so I focused a lot on how do I make sure I do both of these things? How do I champion a few things that a really big ideas that are going to help change the direction of the company, and then how do I articulate that in a simple and compelling why? **Lenny Rachitsky** (00:20:26): That's such a cool simple way of thinking about this. Is there an example from your work that might illustrate some of this from a project you worked on or a product you built? **Anneka Gupta** (00:20:35): I can take some recent examples. We've been doing a lot of strategic planning for where do we want to be as a company over the next three years, and Rubrik operates in the cybersecurity space. It's a very fast moving landscape. There's a lot of places that we could go as a business, and one of the ways that I've exhibited this, and this is what I recommend to other people too, is sometimes it's really hard to come up with the compelling and simple why behind something and sometimes it's also really hard to come up with a really big idea out of thin air. So these things can be very challenging. The first step that I found as very useful, and I use this tactic every single day in meetings, is just summarization. So, bringing people together, lots of different voices into a room and hearing what they have to say and at various times in the conversation summarizing what people are saying and summarizing what that means in terms of the direction that we could go in. **Anneka Gupta** (00:21:34): And then that's a checkpoint of saying, "Okay, this is how I've synthesized what is happening. Is this correct or do we actually need to do another turn because we don't all agree with where we're landing here?" That summarization, even though I may not be adding a new idea into that, I found people actually view that as strategy. They view the effective summarization as strategy. So I think that's one element. Then what I've also found is that when I summarize what other people are saying and especially multiple different stakeholders, then I can think about offline and not in the context of right in the meeting, sometimes in the meeting too I guess, is how do I make this idea one click better? It's not about how do you do something radically, radically different, but taking ideas and then making it slightly better, slightly better. **Anneka Gupta** (00:22:25): When you think about that, especially from an outside-in perspective of what are the customer problems we're trying to solve and how are we going to take this to market, and don't worry about how difficult the technical implementation is going to be, then you start to get to these big ideas that can really be the change agent ideas. So, I've started doing this more and more and I think especially in the past three to six months, and I'm seeing a material difference in terms of the number of big ideas that we're going and pursuing overall as a company and also the quality of the strategic thinking that I can bring to the table, and it's been really exciting and rewarding. **Lenny Rachitsky** (00:23:02): There's so much you're sharing that resonates with other podcast episodes. For example, this idea of just going one click better. I had Roger Martin on the podcast where this book, Playing to Win, which is one of the more popular strategy books, and he has this concept of betterment as a way to work on strategy. A lot of people go huge with a big strategy and vision, and his advice is just find the thing that is the biggest constraint and bottleneck to your business right now and just make it better and that's your next step. And then just keep doing that and you'll end up in a much better place over time, even though it feels like you're just doing one little thing. And so I love this idea of just picking one thing and making it one click better. There's going to be an episode that comes out right before this with Alex Komoroske, and he has this concept of the adjacent possible and it's just find the next thing that's possible and focus on that versus some big lofty thing. So I'm just sharing a bunch of stuff, that's not a question. **Anneka Gupta** (00:23:56): That totally resonates though. **Lenny Rachitsky** (00:23:58): Okay, okay. Okay, great. And then the summarization idea, I love it. So tactical, basically any PM can do this just in a meeting just like, "Okay, let me just summarize to make sure everyone's on the same page." Funny enough, this is the feedback I get on this podcast and I haven't been doing this in our conversation yet, but I often try to summarize the person's point and everyone's like, "Oh, I love that you do that. That's so helpful." So I totally see the power of that in my experience. **Anneka Gupta** (00:24:22): It also makes people feel heard and especially when you have a lot of diverse voices in the room that may not agree on all things but have valid viewpoints, it helps bring people together and ultimately the diverse perspectives are going to yield better insights and better decisions for the organizations. You want that, but some people shy away from that because it's scary because you have to deal with a lot of conflict and it's a way to kind of move beyond the conflict and get to the heart of an issue, which in my mind, that's what the PM job is all about is getting to the very, very heart of a problem. **Lenny Rachitsky** (00:24:56): If someone wants to work on this skill of summarizing as kind of a tactic, can you give just an example of how you would do that? Is there like a phrase to use? Is there words or an example you could give of just like here's how it would look in a meeting? **Anneka Gupta** (00:25:10): Yeah. So, often if there's a lot of discussion going on, sometimes it can be a little hard to insert yourself. I still may insert myself and say, "Hey, let me pause here for a second and try to capture what has been said." This is what I've heard. I've heard that our customers are having these kinds of challenges. We feel like this is the way that we want to solve these challenges. We have a right to win in this way and therefore we're going to take this action. **Anneka Gupta** (00:25:36): Is everyone in agreement with that or is there some dissent about whether that's an accurate portrayal of where we've landed with this conversation? That's the way I'll frame it up and again, ending it on a question so that you're not coming in and just being like, "Hey, this is where we're at." But then inviting people to discuss and say "Yes," or "No, I agree with 90% of that or 10% off." And that helps move the conversation forward because sometimes you'll get stuck in these circular discussions that aren't moving forward and you need to figure out a way to move it forward. **Lenny Rachitsky** (00:26:11): And then you experience is just doing that makes you look more strategic and gives people the impression you're thinking strategically? **Anneka Gupta** (00:26:18): Yes. Yeah. **Lenny Rachitsky** (00:26:19): Awesome. **Anneka Gupta** (00:26:19): The other way you can do it is if you're in a room with someone and you have a whiteboard is actually summarize on the whiteboard while people are talking and then show your summarized framework or whatever on that. So that's kind of a good way to do it too. If you're having a hard time interrupting the flow of discussion or you don't feel as comfortable thinking on your feet and interrupting and then framing your point of view, you can do that. In Zoom you can also use a chat. I've done that very effectively and said, "I'm not going to interrupt the flow conversation. I'm just going to summarize in Zoom chat this is what I've heard, and this is what I think we're saying in this conversation." And then sometimes that'll get invited back into the broader conversation that's happening live on the Zoom itself. **Lenny Rachitsky** (00:27:05): That's a much lower stakes way of doing it, and I'm picturing all the PMs listening to this, they're going to start doing this and there's going to be all these summaries now in Zoom chats and everyone will be like, "Oh my God, why is everyone sharing?" **Anneka Gupta** (00:27:14): And then Zoom AI will start just doing it all for you. Then we'll have to think again. **Lenny Rachitsky** (00:27:19): And then PMs are over and AI replaced us all. **Anneka Gupta** (00:27:19): Yes. **Lenny Rachitsky** (00:27:22): Okay, so then just to close the loop on becoming more strategic, your advice is when someone's like, "Hey, you're not strategic enough. You need to be more strategic." Your insights is the two things to work on is one, be clear on the whys behind the ideas that you're working on and be very crystal clear. People may not be understanding why you're working on the things you want to work on, the things you're pitching. And then two is actually be the person that makes these things happen, not just put a doc out there. If you're not actually achieving them, people are going to think you're not strategic. **Anneka Gupta** (00:27:53): Yep. **Lenny Rachitsky** (00:27:53): Awesome. Okay. I want to talk about decision-making. You have a really interesting perspective on how to become a better decision-maker in relation to being kind of a historian, which I love this concept. Talk about that insight. **Anneka Gupta** (00:28:07): Yeah, so I was at my previous company for 11 years, so I kind of ended up becoming the historian. And when I joined Rubrik about three years ago, I came into an organization that had a lot of history that I just didn't know about. So one of the things that I decided to do when I joined the company was to really understand what happened in the past. What were the products that we launched that weren't successful? Why weren't they successful? What was the perspective on the history of how we've decided to develop the things that we did and why? What was the perception of different people in the organization? I tried to construct this past knowledge of what had happened and what were the decisions that were made and why were those decisions made, whether they were good or bad it didn't matter, so that I could better understand how to make decisions going forward and to learn from the mistakes that I didn't personally live through. **Anneka Gupta** (00:29:07): I think that's the part that's really important about being a historian. You can always be a historian. It doesn't have to be just when you join a company, but even today I'll hear about projects from many years ago that people will bring up and I'll be like, "Tell me about this project. What happened with it? How did we decide to do this?" And just really learn and be curious about it because that gives me more context into, well, what is it that we did poorly and how can we do that better? And also, what is the baggage that people have around trying to do something similar again? Because people always come with their baggage of, oh, this hasn't worked before, so why is it going to work now? And as a product leader, you're obviously putting in place a lot of thoughts and ideas around this is what I want to go achieve and these are the initiatives. And some people are going to come and say, "Well, we've tried that before." Especially you've been at an organization that's been around for a while. **Lenny Rachitsky** (00:29:56): I've been that guy. We've done this so many times. It didn't work. Why are we thinking about this again? Okay, so the advice is if you're new to a company especially, just study the past decisions that were made and share them out as a part of that and then as a side effect, it'll help you make better decisions because you'll have this history about what the company has done. I love that. Along the same lines of decision-making, I asked your former colleague Rachel Wolan what to ask you, and she said that your parting advice when she left to join a different company was it's not about making the right decision, it's about making the decision. That's like the things she remembered about you most, that parting advice. Talk about why that is so important and your insight there. **Anneka Gupta** (00:30:42): Very easy to get into analysis paralysis before making a decision and say, "Well, if I just had this one more data point, if I just knew this, then I could make a decision." But the reality is that you were always operating off of imprecise information as a product leader. What I've found is that once you commit to a decision, you actually learn more post committing to that decision about what's going to work and not going to work, and you move out of the hypothetical. And as long as your decision is like 70% right, you can iterate on that 20, 30% in either direction, but if you don't commit, then you don't actually get any new information that is high fidelity and high quality. So, I'm a big believer in making decisions... **Anneka Gupta** (00:31:28): I know you've had a few guests talk about speed is super important in organizations. Well, I think making decisions quickly and then being able to iterate on them is a form of that. Just make a decision. Don't make it uninformed, but have a strong hypothesis and then just keep testing whether that hypothesis is accurate or not and you'll shift here and there. You might build something that you have to throw away 20% of the work on, but that's okay. It's better than making no decision at all because you won't get any new information if you don't make any decision at all. **Lenny Rachitsky** (00:31:56): As a PM that might be listening to this, feeling like, "Okay, yeah, that sounds great." But then I make a bad decision and then Anneka is going to be like, "You messed up here. You've shipped the wrong thing here. It didn't work." How do you create a culture where people don't feel that and aren't as afraid of making bad decisions and making decisions with 70% of the information? **Anneka Gupta** (00:32:19): I think part of it comes down to making sure there's a strong hypothesis that everyone understands when you're making the decision. Or it might not just be one hypothesis, it might be a series of hypotheses and assumptions that we're making that are informing the decision. So it might be a hypothesis that this segment of customers is going to be willing to pay for this product because it's solving an urgent and important enough need for them that they're going to go do it and this is the evidence we have to find it, but this is also the stuff we don't know. **Anneka Gupta** (00:32:52): Then along the way, we learn whether that hypothesis is true or not. And so at the end of the day, if something didn't work out, we can go back to the original hypothesis and say, "Well, this is what we learned in this process that our hypothesis was actually not true, and we learned all of this after the fact." I think the way to make a culture of risk taking and people willing to make these bets and go out on a limb is to reward the learning versus the outcome. That's what I try to focus on is if we're constantly learning, it is okay if we make bad decisions, but we learn from them and we get better for next time. Even in making this bad decision, we learn something about our customers or our business that we otherwise wouldn't have learned that we can use in another context. **Lenny Rachitsky** (00:33:40): First of all, I love that this comes back to your strategic lesson of just if you have a strong why behind something, that's incredibly powerful and people will be confident that you're thinking strategically. Two, I was just at a talk with Zuck. He's being interviewed at the Chase Center, the Acquired Podcast at this whole event, and his main thing that he talked about that he values most in the culture of Facebook is learning faster than anyone else. Shipping stuff that isn't perfect, but just so that you can get one more turn and learn something faster than someone else. So, that super resonates that's Facebook's culture. Is there an example of something you worked on where you did that, where you kind of ship something that you weren't fully confident in and you learn faster? **Anneka Gupta** (00:34:26): Yeah, I mean, I think there's a lot because anytime you're shipping products, there's so many different things that could go right and wrong. There's a situation where we created a really amazing high value product and we decided not to monetize it, and then we realized after the fact, "Wait, we should have monetized it. So, we're trying to figure out how to package some new capabilities to monetize this thing that we know has a lot of value without taking away what we've already given to existing customers." So that was something we learned along the way that we originally didn't think, oh, we should monetize this, but then we realized that there's actually an avenue to do that after the fact. There's been other things where we've developed a set of capabilities thinking that it will solve for this new persona's problems, but then we misunderstood how easy it was going to be to go sell to that new persona within our own organization. I've made that mistake many times actually. **Anneka Gupta** (00:35:26): And so now I think now what I've taken from that is really know how you're going to sell something and who's going to do the selling before you actually go build out the product. Because if you don't have that right focus, you may build out the best product and yet it's going to get zero adoption because no one in your organization is ready to sell it. So there's tons of stuff like that where it's like been okay, yeah, we've learned something from this, and it's not all throwaway, it just means that we've got to do something differently for this product and we need to do something differently for our organization going forward. **Lenny Rachitsky** (00:36:01): **Anneka Gupta** (00:38:06): I try to embody the mindset of feeling like and believing that I can work with anyone. I think what I do when I hit a difficult personality and difficult personalities come in all shapes and sizes and forms is I really try to understand what drives that person. What is it that they really care about? Hopefully they care about something deeply about the company and making the company successful. Sometimes they care about their own personal career, how they're showing up, what people view of them. That's fine. I just need to understand what it is that they really care about, and then if I need something from them, what is it that I can do to motivate them to find what I need from them important? And trying to make that match of they have this desire kind of like building a product, they have this desire and how am I going to get them to care about the thing that I want to care about? **Anneka Gupta** (00:39:08): The other thing I do is instead of feeling like anger or frustration with the person and instead trying to shift that to a mindset of feeling gratitude and a positive emotion about them is I look at them and I ask myself what can I learn? Maybe I don't want to adopt their personality or operate the way that they are operating, but everyone has something that they can teach you, whether it's their communication style or the way they're able to marshal people together, the way they come up with visionary ideas, whatever it may be, trying to study that person and be curious about them, learn from them and then thank them for that and feel the generosity genuinely about what I got from this situation. It's easier to do sometimes than others, but I think it comes back to that abundant mindset. If you can approach it with an abundant mindset, then you can really consciously do this and when you actually learn something, you will feel the gratitude when you recognize that you are able to get something from that. **Lenny Rachitsky** (00:40:13): I love that this connects with your other original piece of advice of just turning something into this is going to be fun. Let's make this fun. And in this case it's like make it great. What can I learn from this person even though they're really annoying me and it's frustrating and don't want anything done? Then your other point of understanding what they want and kind of using that as a way to pull them in your direction, how do you figure out what they want? Do you have any tricks for just like, "Here's how I learn what this person's motivations are and goals are"? **Anneka Gupta** (00:40:42): Talk to other people that have worked with them before and have done so successfully. So that might be people that work for them because if you work for a person like that, you have to figure out and or you're successful working for that person, you probably understand what makes them tick. So that's one, or talk to people that are peers, anything like that to try to understand and build this view of this person that helps me empathize with them and also helps me understand what they may be wanting to get out of a situation and why. **Lenny Rachitsky** (00:41:16): I love that. Yeah, they don't have to be involved in that. You just ask other people, "What is this person's motivations?" And then the idea is connect what they want with the thing you're trying to achieve. Beautiful. I really love this idea of when you're frustrated by someone just reframing it to like, "I'm grateful I'm going to learn something from this person in our interaction, even though they're making life hard for me." I really love that. Another skill I hear you're really strong at, and this comes from another one of your colleagues, Hema Mohan shared that you're world-class at giving feedback, giving hard feedback, and receiving hard feedback. And so I want to just ask you, what have you learned about how to do this? It's very hard to give hard feedback. That's why it's called hard feedback. So from either direction, what have you learned about receiving hard feedback or giving hard feedback where someone actually hears Zoom doesn't get defensive? **Anneka Gupta** (00:42:07): The answer is so much, I've learned so much from it. So maybe I'll start with receiving feedback. So, on the receiving feedback side, I think it's very natural to feel upset, defensive, all the negative emotions when you first see a piece of negative feedback, whether it's you're reading it in a employee survey or you're receiving it in a one-on-one from a direct report or from a manager or from a peer. And I try to let myself just feel the things that I'm going to feel. Sometimes that's an emotional feeling, sometimes that means I want to step out of the room or it depends on who I'm talking to, but let myself feel the things that I'm going to feel. Then once that's passed, whether that's a few hours or a few days, don't react. Don't try to say, "Oh, I don't believe this." Listen. And then ask myself, okay, well where is this feedback coming from? Why am I getting this feedback? **Anneka Gupta** (00:43:07): And try to be super curious about it. And that might be going back to the person that gave me the feedback and maybe asking someone that's a peer somewhere in the organization that might have more context and flavor to what the feedback really is, just trying to learn. Then I can decide, do I think this is valid or not? Is this something I should do something about or not? Actually, all feedback I think is valid. People's feelings are valid, but it doesn't mean that you need to do something about all of those things. Going through that process and letting myself ride the emotional wave and not judging myself for that, but then not reacting and letting myself then figure out and come back curious. I think when you come back curious, people then want to give you more feedback because they know that you're listening and that you're hearing what they say. **Lenny Rachitsky** (00:43:55): So the advice is feel it, don't block it off and be like, "No, no, no, no, no, this isn't real." So fully let your body go through the roller coaster of feeling the negative feedback. Sometimes the feedback is just like, "No, this isn't actually a thing." Do you have any just heuristic of like I should actually pay attention to this deeply or just like let me wait for more data points? **Anneka Gupta** (00:44:15): Yeah, I think in product you receive feedback all the time for your organization or for yourself, and you can't make everyone happy. Everyone wants a different thing from product. So I think this comes up quite often where there's a lot of feedback for the organization or for you as a leader and you have to decide what to focus on and what not to focus on. I always try to anchor on, "Well, what is best for the company and what does the company need for me and for my team at this point in time?" There's stuff that is a must-have on that list, and there's stuff that's nice to have. Sometimes there's just too many must-haves to go deal with the nice-to-haves and you have to just be like, well, I know this is a problem, or I know we could be 10% better in this, but it actually doesn't matter as much as fixing these things that are really, really important and are really what's going to help my organization deliver what it needs to for the company and for the business overall. **Lenny Rachitsky** (00:45:13): In terms of receiving hard feedback, so you shared one example or I shared an example where someone said you weren't strategic enough. Is there another example of receiving hard feedback that you got that you're like, "Ugh, that sucks"? Either earlier in your career or more recently, anything else come to mind? **Anneka Gupta** (00:45:26): I mean all the time. So there's always hard stuff. Well, people will give feedback of, "Oh, I feel like we're not moving fast enough on our roadmap and priorities. We need to be doing more. Why aren't we moving fast?" Or- **Lenny Rachitsky** (00:45:47): Never heard that one before. **Anneka Gupta** (00:45:48): Never heard that one before, right? Or disparaging the direction that we're taking a certain product because they don't agree with it because a competitor is doing something else, but we've decided for our reasons that we're not going to go follow that path. There's always something that people have negative feedback about and sometimes I'm like, "Okay, this is an eye roll." I understand where they're coming from. I understand why they're giving me this feedback, but I also don't agree that we should change directions because of it. I don't know, some of the things cut deeper than others, but I think people are making personal statements about my team or they're feeling like, "Hey, the product team isn't listening to feedback, or the product team has a bad culture. Anneka isn't listening." Things like that cut deep and are a lot more... I know like physiologically they make me kind of seize up a little bit, but again, then I try to feel the things I'm going to feel and try to understand why are they saying that. Why do they really feel that and what does that mean behaviorally that I have to do differently or my team has to do differently or maybe just two people on my team need to do differently and someone is extrapolating this out to be a much bigger problem than actually is? **Lenny Rachitsky** (00:46:59): Awesome. Okay, and then we were going to shift to what you've learned about giving hard feedback so that someone actually listens and doesn't just put up a shield and like, "It's not real." **Anneka Gupta** (00:47:10): So I think in giving feedback, you can never fully control how someone else is going to respond to that feedback. All you can control is what you do, your body language and what you say. What I have found is that if I can convey, and I will say this very directly to people, I care so much about you and I'm giving you this feedback because I want you to be successful and I want you to be able to reach the pinnacle of what I know you can accomplish. And you do all of that setup and you don't just hope that they understand that, you actually explicitly say that and you show that in your body language, then it makes the other person much more receptive to hearing whatever you have to say. Then I think the other piece is that you've got to be direct. **Anneka Gupta** (00:47:57): The worst feedback is the kind of passive-aggressive feedback versus saying directly this is what you are doing or this is how you are being perceived in the organization, and here are the three things that you can do to change the way you're being perceived or to change the outcomes of what you're driving or become more strategic or whatever it is that I'm trying to give feedback on. I do a lot of prep before I give someone a lot of feedback. I really think about how can I frame this in a way that's going to resonate with them that doesn't come across as attacking them, but helps them understand why what they're doing isn't working or is being perceived poorly? And try to give them examples and even examples that I've personally had to go through myself of how I've approached those situations. And let them ask questions and brainstorm with them, be part of the solution versus saying like, "Here's all this feedback, now you go figure out what to do with it." **Lenny Rachitsky** (00:48:56): This reminds me of Radical Candor. Basically make people feel like you care deeply about them, but be very direct about what they can be doing better. Are there phrases or ways that you set up the conversation? You mentioned a few of just like, "I want to help you become the best version of who you could be and what you're capable of." Is there any phrases you find helpful that you come back to often of just a way to start the conversation? **Anneka Gupta** (00:49:21): Yeah, I think what I started with is like, "I care a lot about you. You have a lot of potential. I can see you doing these kinds of things. I can see you getting to where you want to go in your career." Sometimes I even start the conversation by asking them, "What do you want to do? Where do you want to go in your career?" And that will help me frame up which of these things are important. Because honestly, if someone wants to be eventually like a CPO, the feedback I'm going to give to them is very different than if they're like, "Hey, I don't really want to manage people ever. I just want to be the best I see I can ever be." I'm not going to give them the same feedback. And so having that conversation up front also allows them even before I jump into the feedback to give them their perspective of what they want and then I can tailor the conversation more to what they're looking for. **Anneka Gupta** (00:50:04): I think that has really helped as well make sure that I focus on the things that are going to really matter. During the feedback conversations, I also try to frame things as this is how you're being perceived than you are doing X. Because I think even though it's hard to hear, "Oh, hey, this person doesn't perceive you in the way that you may think," then we can talk about, "Well, what are ways that we can change the perception?" I also think it's important because sometimes people are like if you say, "Hey, I don't think you're X," and then they're like, "Well, yes I am." And if you're saying, "Hey, well this is how other people perceive you including me, but maybe this is not what you are intending," and you actually say that, you're giving them the benefit of the doubt of actually how they're trying to show up is different than how people are perceiving them. You can have a better conversation then around, "Well, what can you do to change that perception?" **Lenny Rachitsky** (00:51:01): You mentioned I see product managers, and this is a good segue too. You're a big deal, fancy chief product officer person. A lot of people listening to this podcast are early career PMs or trying to get into product. I want to ask a couple of questions along these lines. One is about getting into products. So, interestingly, you got into product the same way I got into product, which is you used to be an engineer and then you moved into product within a company, which is maybe one of the simplest ways to get into product potentially. For people that are trying to break into product management, what advice do you often give them of how they could go about doing it? I know there's never the silver bullet, but what's your advice? **Anneka Gupta** (00:51:41): I definitely think doing it within the same company is a lot easier than trying to switch companies and switch jobs at the same time because when you're within a company, you've already built credibility, hopefully. And if you haven't, then go crush it at your job so you build the credibility. Then you can start to raise your hand, interact with the product team, take on projects and do things that allow you to get some experience and build a relationship with a leader on the product team who then may be willing to take a chance on you to put you into a product role even if you don't have the experience. Especially when you're within the same company, you bring other things to the table. Let's say you're working in customer support, well, you have a huge amount of knowledge about what are the big problems that people are calling up the support team or opening tickets on the support team for, and that is valuable knowledge for being a product manager. **Anneka Gupta** (00:52:33): You're coming from the sales side, you're coming with a knowledge of how to sell the product, what really resonates, how do you do the objection handling, and that can be a valuable perspective. If you come from the engineering side, but you understand how the product is built and you understand that technical nuances of that well, that can also be a valuable way to enter into the product team. That way, even though you don't have the direct product experience, you're still bringing something to the table where you are going to have to get trained on core product management, but you're not going to have to be totally trained on the business or the technology. **Lenny Rachitsky** (00:53:06): So is the advice basically get a job in any function, not necessarily any function, but join a company however you can essentially and then push to try to get into the product team in some form? **Anneka Gupta** (00:53:19): Yeah, I think join a product adjacent function, which honestly pretty much every function is product adjacent, because what function does product not engage with, but as closely product adjacent as possible, and then yeah, find your way into the product world from there. **Lenny Rachitsky** (00:53:34): Ideally there's something within the company, there's some program I imagine that does this sort of thing. Some companies have something structured, some are just kind of ad hoc. Is there anything there you're just like should you talk about this in your interview just like, "Hey, I would really love to become product manager someday." Do you have anything along those lines that would help me get into that or not? Or should you not talk? **Anneka Gupta** (00:53:52): Well, I think it depends. For instance, when I joined LiveRamp, which was my previous company as a software engineer, I actually did say in the interview process I want to become a product manager I think. At that point I was still early in my career, I didn't know for sure, but I said that. Now that was a 20-person startup, so it was worth saying it because they didn't really have a product team and I wanted to put it out there that that was something I was interested in growing into. **Anneka Gupta** (00:54:17): If you're joining a 5000-person company, you're hiring manager is probably not going to receive it well if you're like, "Hey, I'm interviewing for product marketing, but really what I want to do is go into product." So, it just kind of depends on the company and the stage. You have to play that wisely. But I think once you're in a company, then finding a way to make a relationship with the product leader, or if you're in a startup that is really small and they don't have product management, well then you have the opportunity to take on projects for sure that are product management related because no one is doing that work. Really taking initiative to do that so that you can find an inroad into product management. **Lenny Rachitsky** (00:54:57): Kind of along these lines, you have a really unique perspective on new PMs because you teach product management at Stanford. You've been doing that for a while. I just want to ask you work with a lot of people that are new to product, thinking about getting into product, then get into product. What do you find are the things that new PMs or people getting into product most misunderstand about the role of PM or are most surprised by when they become product managers? **Anneka Gupta** (00:55:23): When we interviewed students as we were designing the class about what they wanted to learn, what was most surprising to me was that students would say, "Well, can you teach me how to use Figma? Can you teach me the tools that product managers are going to have to use?" What was surprising me about that was I don't think it's the tools that you need to learn to be successful. I think what you need to learn to be successful is how to take very ambiguous situations and consistently drive more and more clarity over time. So, it was interesting to see this mismatch between what people said they wanted to learn and what I felt they actually needed to learn. **Anneka Gupta** (00:56:03): Now, having taught this class for a few years now, I think talking to students who have then left and become product managers, they've seen a lot of this in practice now and I think they understand that, but there is this mismatch of people who haven't been in product management saying they want to go and thinking that they need to learn some tools or process versus the mindset and the skills required to clarify ambiguity. **Lenny Rachitsky** (00:56:29): Along those lines, I actually saw you somewhere in a talk or maybe something you wrote talk about how creating this class and creating the curriculum helped you crystallize your own thinking on product and helped you crystallize the mental models of becoming a product manager. Is there anything that you recall from that time of like here's something that's really helped me understand about this function and the skill as you were putting together the class? **Anneka Gupta** (00:56:51): Yeah, I know anytime you're teaching something, you have to figure out a way to synthesize it for another audience, and so many of us have learned product management just figuring it out on the job. I don't know if there's a particular framework that I would say came out of that, but what I found very interesting was seeing the questions that people asked in the class and then feeling like, "Oh, I understand how to answer this question. I can provide an example for it." That was super interesting to me because I didn't expect that coming out of the conversation. Yes, there's frameworks we developed to talk about ideation and product discovery and all of that, but I think those are fairly flexible frameworks. **Anneka Gupta** (00:57:33): What was most enlightening was being able to crystallize the answers to some of these questions, whether it was about how do you interact as a PM effectively with engineering or what happens if the data shows you that it doesn't matter which direction you pick, like there's merits to both ways. How do you actually go about making those decisions? It was very interesting being able to then have those conversations with students and bring in the real life examples. And I found in some situations that actually go back to my own team and share the same answer that I came up with in class, I was like, "Oh, this is actually a valuable thing to share with my team back at my company." **Lenny Rachitsky** (00:58:15): Reminds me of the recent chat I had with this guy Alex Komoroske, where he talked about how oftentimes talking with people helps them uncover new insights that he had in his head and then he writes them down as soon as he says something that's really clever in any way. He's like, "Okay, I'm going to remember that now." Coming back to how to become a PM, so you see all these people getting and taking this class want to become product managers. I know they're like Stanford students and people more likely hire Stanford people. But I guess in terms of how they end up becoming PMs, if you were to look at the pie chart of the people that end up getting a PM job, what's the biggest chunk? Is it they join at some other function and then move into product? Do they just join as a junior PM somewhere? How are people actually getting into the PM role in that class? **Anneka Gupta** (00:59:00): Yeah, I think very few are directly going to an established company and becoming a PM directly, so I would say a big chunk of them. Some of them are, but many of those then had PM experience to begin with or had engineering experience and then went to a technical company into a PM role. The vast majority of them are joining product adjacent roles or they're going to small startups where they might be doing product management, might be the first product manager, or they might be doing product management plus plus, chief of staff, something like that where they get to put their hands in product management, but it's a super small company. So I think those have been the two most successful paths to get into product. **Lenny Rachitsky** (00:59:40): Awesome. That's a really interesting lens into how people actually get into this role. Potentially final question, but we'll see where it goes. I have this recurring segment on this podcast called AI Corner where I try to get a sense of just how people are finding AI tools useful in their work, in their life. So, let me just ask you, is there anything you've found useful in some AI tool in how you work? Like something you found that helps you work more productively, more efficiently, either you or people on your team? **Anneka Gupta** (01:00:08): One way that we're using AI today is summarizing our user research calls. So, that has been really valuable because we're doing all these calls all the time, we're getting a ton of rich insights. Some of those rich insights are related to the specific project that we were doing this call for and some of them aren't. And now we have that summarized and tagged in a way where you can look up any sort of thing that you want around the calls that we've done and it'll find you the call, it'll find you the context, it'll find you the transcript and summarize exactly what we've learned from that call. So we're starting to use that more and more. It's very powerful capability. I definitely think that that kind of summarization of information for PMs is a big unlock for organizations and I think we're still in the very, very early days of AI making a meaningful difference to the way that PMs do their work. **Lenny Rachitsky** (01:01:01): Is there a specific tool that you love to help you with that that you may want to give a shout-out to or is it something you guys built? **Anneka Gupta** (01:01:07): Yeah, we use Dovetail and it's been fantastic. Connects into all of the Zoom calls and everything, it does a great job with summarization, with search, everything. **Lenny Rachitsky** (01:01:18): Awesome. I love it when someone recommends a very awesome sponsor of the podcast. Dovetail is ongoing and excellent sponsor, so I'm really happy to hear that. Amazing. Anneka, is there anything else that you thought you wanted to share or that you want to leave listeners with that you think might be helpful before we get to a very exciting lightning round? **Anneka Gupta** (01:01:38): The mindset that you bring to your work is actually the most important thing over anything else that you can do. And if you are approaching every situation as much as possible with the positive mindset, you can do more than you could ever possibly hope to achieve. **Lenny Rachitsky** (01:01:56): I'm going to pull on this thread because this is such a powerful point and I think it's easy to just hear that. It's hard to learn to do it. Do you have any advice on just how to build that mindset? Like it connects to many of the things you said: how can this be fun? How can I be grateful to this person that's annoying me and the things that they might teach me? Is there just anything you've done that has helped you build this mindset? **Anneka Gupta** (01:02:20): Journaling is very powerful. So actually growing up I journaled every single day of my life from when I was 13 to when I was 23. And while I cringe to go back to read any of those, I think what it helped me do and build a practice around that I still do today is when I have a lot of thoughts going through my head, especially negative thoughts, just putting them all down on a piece of paper, writing them on my phone and trying to explore why am I feeling this way? Why am I getting triggered? What is it about the situation that's making me feel so strongly? **Anneka Gupta** (01:02:56): And when I put it down on paper, then it takes this thing that's abstract and things that I'm ruminating on and actually makes it possible for me to break it down and understand, "Well, okay, this is something I may feel, but the why behind it is a little irrational, so let me let this go." I realize that this isn't rational way to think about this. Whereas other things I start to uncover, well, what is it about the situation and what is it that I need to do differently? What's within my control and what is it maybe that I need to go talk to someone about and say, "Hey, I need you to do this differently to be able to make myself feel better and make the situation better." **Lenny Rachitsky** (01:03:34): It's interesting this is another thread that's been coming up a bunch on the podcast recently that when something is bothering you or something is hard, the more you actually listen to that part of yourself and dive into it and explore it and give it a space to share and talk, the less power it gets and the more space is created for the stuff you actually want to take space. It's not what you would expect because usually it's like, "No, shut up, everything's fine." But the more you actually hear that out, the easier things get. So, I love that you share that. **Anneka Gupta** (01:04:09): It's like doing cognitive behavioral therapy on yourself. That's how I think of it. I've never actually done cognitive behavioral therapy, but I've read a lot about it and sometimes when I go through this, I'm asking myself the same questions that I think are asked in those settings. **Lenny Rachitsky** (01:04:26): Love that. All right, Anneka, is there anything else that you wanted to share or leave listeners with? **Anneka Gupta** (01:04:29): I think that's all I can think of. **Lenny Rachitsky** (01:04:31): Well, with that, we've reached our very exciting lightning round. Are you ready? **Anneka Gupta** (01:04:35): I'm ready. **Lenny Rachitsky** (01:04:36): All right. First question, what are two or three books that you've recommended most to other people? **Anneka Gupta** (01:04:41): The Hard Thing About Hard Things by Ben Horowitz, such a great book, great again about mindset of how to approach hard things. Second is I'm a huge fantasy sci-fi fan, so I love Brandon Sanderson's books. I highly recommend those to people as well. **Lenny Rachitsky** (01:04:57): All I know about him is I saw videos of him after COVID where he just said, "I wrote five new books during COVIID." I was like, "what is going on?" **Anneka Gupta** (01:05:03): He is someone that is at the top of his craft and I admire people so much that are truly the elite in what they do, and he's truly the elite in what he does. He writes a lot about writing, he podcasts a lot about writing. It's pretty impressive. **Lenny Rachitsky** (01:05:17): And he writes fantasy books, is that right? **Anneka Gupta** (01:05:18): He writes fantasy, yep. **Lenny Rachitsky** (01:05:20): Okay, cool. It feels like a lot of books to read though. I'm just like, "Oh, my God, so many books." Okay, great. Next question, do you have a favorite recent movie or TV show that you've really enjoyed? **Anneka Gupta** (01:05:31): Again, on the fantasy sci-fi track, I really like Fallout, which is a dystopian show based on a post-apocalyptic, post-nuclear war world. It's very entertaining. **Lenny Rachitsky** (01:05:42): Yeah, it's just very quirky and fun. **Anneka Gupta** (01:05:45): Yes. **Lenny Rachitsky** (01:05:46): And unexpected. Awesome. Do you have a favorite product that you've recently discovered that you really love? **Anneka Gupta** (01:05:53): My eight-foot iPhone charger. So I have a cord that's very long that allows me to move around the house and do stuff while my phone is charging because my phone is always running out of batteries. So, highly recommend getting a super long charging cord. **Lenny Rachitsky** (01:06:10): I've got one of those and I know exactly what you mean. Do you have a favorite life motto that you often come back to find useful and work during life? **Anneka Gupta** (01:06:18): I think it comes back to dealing with lots of different types of people. I really try to remind myself that everyone has something to teach and everyone has something to learn. I think that helps not only think about how you interact with other people, but also combat imposter syndrome because you have something to bring to the table and teach as well as anyone else, no matter what your age is, no matter what your background, and leaning into that and realizing that people can learn from you and you can learn from others in every single situation. **Lenny Rachitsky** (01:06:51): Final question. I heard that you're a big fan of Isaac Asimov. Do you have a favorite Asimov book, one that you'd think if someone were to explore his canon, they might want to start with? **Anneka Gupta** (01:07:01): I really like the Foundation series, so starting with that is really good. It's a very different style of writing. You kind of have to stick with it, but it's good, I promise. **Lenny Rachitsky** (01:07:11): And I'll build on that and say, "Don't watch the show because the show is so different from the book series." I don't know if you've seen it and- **Anneka Gupta** (01:07:16): Yes, I have. **Lenny Rachitsky** (01:07:17): ... not nearly as good. **Anneka Gupta** (01:07:17): Okay. **Lenny Rachitsky** (01:07:18): I was just like, what is going on? This is not the story. **Anneka Gupta** (01:07:20): Yeah, very different. **Lenny Rachitsky** (01:07:21): What are they doing? Amazing. Anneka, this has been amazing. We covered so much ground. I feel like this is going to help a lot of people. Two final questions, where can folks find you online if they want to follow up on things, maybe ask you questions or just check out the stuff you're up to and how can listeners be useful to you? **Anneka Gupta** (01:07:38): You can find me on LinkedIn, follow me, DM me. I would love to connect. The way you can help me is we're actually redesigning our Stanford class right now for PMs, and I would love to hear from you if you don't have any PM experience, what is it that you wish a class could teach you? And that would be super helpful for me as we're redesigning this class. Thanks. **Lenny Rachitsky** (01:07:59): Amazing. And the way they could share that is DM you on LinkedIn or Twitter? **Anneka Gupta** (01:08:03): Yes. **Lenny Rachitsky** (01:08:06): Easy. Amazing. Anneka, thank you so much for being here. **Anneka Gupta** (01:08:07): Thanks for having me. **Lenny Rachitsky** (01:08:09): Absolutely. My pleasure. Bye everyone. **Lenny Rachitsky** (01:08:13): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [5/17] How to see like a designer: The hidden power of typography and logos | Jessica Hische (Lettering Artist, Author) **Jessica Hische** (00:00:00): Most people are better at understanding the feelings and sensations that typography and logos give us than they give themselves credit for, because what we are as people are endless absorbers of patterns, and information, and all this kind of stuff as we move throughout the world. We don't take time to sit and digest it, but it's still coming in and getting logged, and so even as a non-designer, I think you can look at examples of logos where something's not quite right and be like, "Something's not right here, I just don't know how to name it." But I think a good exercise is just like looking at fonts that are available in the world and asking yourself, "What feeling does this give me?" **Lenny Rachitsky** (00:00:47): Today, my guest is Jessica Hische. Jessica is a design legend, and it was such an honor to both have her on this podcast and also to work with her on a refresh of my newsletter and podcast logo and brand, which is launching around the same time as this episode comes out. Jessica is a lettering artist specializing in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, the United States Postal Service, Apple, Nike, Tiffany and Company, The Gap, and Penguin Books, and her work has been featured in design and illustration annals, both in the U.S. and internationally. She's helped create logos for Philz Coffee, Eventbrite, and Mailchimp, is a best-selling children's book author, and if you live around the Bay Area, you've seen her work all over the city without knowing it. In our conversation, Jessica shares the process that she went through to update my logo and brand for my newsletter and podcast. **Jessica Hische** (00:02:19): Happy to be here. **Lenny Rachitsky** (00:02:21): I thought it'd be good to start with asking you just to describe what it is you do, because you're very atypical of the kinds of guests I have in this podcast and you also have very unique skillset. **Jessica Hische** (00:02:32): Yes. Well, I will describe what I'm most prominently known for, because I'm a person who just does a lot of things, but the thing that I do the most professionally is custom typography, like bespoke lettering pieces. That translates to working for all kinds of things. Sometimes it's for film and television. I've done movie titles and things like that and television credits and stuff. Sometimes it's book covers. Actually, a lot of times, it's book covers, and then a big part of my business is doing logos, and logo refreshes, and things like that, so basically being the person who knows all the things so you don't have to have that person on staff when it comes to typography. **Lenny Rachitsky** (00:03:17): **Christina Gilbert** (00:04:21): Yes. Thank you for having me on, Lenny. **Lenny Rachitsky** (00:04:23): What is the latest with OneSchema? I know you now work with some of my favorite companies like Ramp, Vanta Scale, and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs. **Christina Gilbert** (00:04:39): Yes. We just launched OneSchema FileFeeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP folder. We see our customers all the time getting stuck with hacks and workarounds, and the product teams that we work with don't have to turn down prospects because their systems are too hard to integrate with. We allow our customers to offer thousands of integrations without involving their engineering team at all. **Lenny Rachitsky** (00:05:01): I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema, and not just to build it but also to maintain it forever. **Christina Gilbert** (00:05:12): Absolutely, Lenny. We've heard so many horror stories of multiday outages from even just a handful of ad records. We are laser-focused on integration reliability to help teams end all of those distractions that come up with integrations. We have a built-in validation layer that stops any bad data from entering your system, and OneSchema will notify your team immediately of any data that looks incorrect. **Lenny Rachitsky** (00:05:32): I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us. If you want to learn more, head on over to oneschema.co. That's oneschema.co. **Lenny Rachitsky** (00:05:47): Part of the reason I was excited to have you on this podcast is that I was lucky enough to get to work with you on a refresh of my logo and brand for my newsletter and my podcast, which I'm very, very excited about. It's actually going to be launching right around the time of this episode going live, so this is, in part, a celebration of the new look, and logo, and brand. I thought it'd be an awesome excuse to bring you on the podcast and give an inside glimpse into the process of updating a logo and a brand. Partly, because I think it'll just be people are like, "What the hell? How did this change? Where did this come from? Why this versus that?" and also just for people that are thinking about this for their own product or business, to understand the process and understand when it might be right for them, when it might be not right for them. Broadly, how does that sound? **Jessica Hische** (00:06:32): Sure. Yeah, of course. Everybody that starts a company knows that they need a logo. That is a big thing. Some people start a company and think the logo is going to drive the culture of the company, which I don't think that that is true. I think that the product itself, and the team you build, and the people you put together are the thing that should be driving things forward, but I do think the logo and the brand assets can generate a lot of both internal and external excitement and just tell people what to expect from the thing that they're about to engage with. Some people say don't judge a book by its cover. I'm the opposite, where any book... The cover of the book should be giving you incredible insight into what is on the interior of the book and setting the tone and setting the vibe so that when you open the book and read the book, it's a symbiotic thing where you're like, "Oh, I understand what I was getting into. This got me excited about starting it," and whatever. It keeps that ball rolling. **Jessica Hische** (00:07:34): But with the refresh work that I do, a lot of people start companies and they have a certain amount of money. If they're bootstrapping it, they have less. If they get venture money, they have a little bit more. But what they don't want to do is spend venture money on a massive brand exploration when you're still in the hiring process, you're still trying to get early stage engineers, and all that kind of stuff, and so I am sort of a weird contrarian in this way in the brand world where brand people are like, "Brand is everything. You need to take a significant investment in brand because that guides the vision of the product or whatever." But I think being a bit more of an insider within the tech world, I understand that sometimes people start companies and have an intention to do something. **Jessica Hische** (00:08:24): While they're doing that, they're building the team, they're doing cool stuff, but then the company has to pivot for one reason or another, whether a competitor immediately comes out with a thing that you're doing or the technology that you're doing gets postponed, whatever's going to feed into it, and so if you invest super heavily on the whole brand vision from the jump, sometimes it's like throwing away money if you have to pivot. What I love about the work that I do is that I understand that a lot of people have to just have something to put on decks and have something to put on a holding page or whatever, and internal teams are totally capable of doing that early work. But then if it does become successful, you don't want to get locked into whatever it is that you had to throw together before an investor meeting or something. **Jessica Hische** (00:09:15): I come in then to take the existing vibe and smooth it out, address any of the concerns that came up. A lot of times, it's really utilitarian stuff like this doesn't scale well, or this thing falls apart in this context, or we never had a good avatar version of it, or whatever. Sometimes it's really specific utilitarian fixes, and sometimes it's just about growing it up and sophisticated it without losing what was there in the first place that people got excited about. **Lenny Rachitsky** (00:09:46): To give people maybe a couple more tactical piece of advice here, what's a sign that it's maybe time to do something with your logo and brand from you took a first pass, it's good enough, your wife made one, your husband made you a logo, it's like, "Well, this is great. Let's just go with this"? What's a sign that maybe it's time to, "Okay, we should actually at least uplevel this, not necessarily hire studio but takes something to make it better"? **Jessica Hische** (00:10:10): Well, one of the things is if, suddenly, you're starting to deal with the greater rollout of the look and feel of the brand. If you, at first, just basically had a really beta website and small version of the app but you're about to do a new one that kind of updates and expands it, that could be a really good time to roll it out. One of the things that a lot of people do when they're starting a company is that they'll make a logo with a font that is really popular or widely available or free. If you are about to, let's say, print a bunch of swag for new hires, or you're hosting a conference, or whatever is that event where suddenly you're going to physically invest money in making stuff with your brand on it, that might be a good time to do it. **Jessica Hische** (00:11:03): One of the reasons why I tell people why having a custom logo or custom typography can really matter is that if you're using something that's available to everyone, the chances of someone else coming in and copying you are very easy and high. You might be one of these lucky companies that just out the gate is outrageously successful, but with success comes people climbing up behind you trying to copy your success. If that success is very easily copyable and people will try to trick your customers into coming their way by repeating the things that you're doing, including the branding, one way to avoid that is by doing something that's more customized when it comes to the logo and brand. **Lenny Rachitsky** (00:11:47): Let's actually talk about the work that you put into updating my logo and brand. From that, we can spin off into lessons and insights that you have along these lines. Overall, just high level, what's the process you go through to go through a logo refresh? **Jessica Hische** (00:12:01): Sure, of course. Super high level, it's figuring out what the goals are. Some people have a goal where they want their customers to not notice it at all. They're like, "Oh, everybody loves this, but I, the person with a design eye, can see all the problems with it. I need to roll something out that fixes the problems that I see but that no one else really notices." If that's one approach to it, which is a very close in refresh where we're just trying out little things to make it feel custom or fixing things that have come up when stress-tested, whether it looks crazy when you scale it and looks like horsey and heavy-handed when you scale it too big or when you scale it too small, you lose a lot of legibility and stuff like that. That's what would be a really close in exploration. **Jessica Hische** (00:12:53): For other people, they might have bigger goals where they're about to pivot the company to try to attract a different audience or things like that. They might have this really cool and successful group of people that are super users but they're trying to expand it, so then it's about, "What can we do to shift the vibe to make it include these new people without excluding our core folks?" My first round is figuring out what that scope is, how experimental, how broad are we going to go for that first round, because then everything else cascades from there. If we go really broad for the first round, then we're in this process of narrowing down the scope as we go down. Whereas if we go really close in for the first round, we're already just talking about really technical stuff. **Jessica Hische** (00:13:45): This is another thing that is a little bit unique to me that not everybody else does, but I will hand off files to clients to try in situ really early on if what we're trying to do is solve utilitarian issues. Most other people are like, "No, you don't get the files until we do the final because I don't want you to run away with this or whatever." There has to be some trust with it. Yeah, figure out what we're trying to accomplish and always keep those goals in mind, and then scope out the process based on what those goals are. For each round, we're addressing different things. First round might be about just capturing the overall look and trying things as broad as we can, and then the next round is, "Okay. Well, now we have generally a look that we want, but is it the right weight? Is it the right letter height? Do we have enough details?" That kind of thing, and then we get narrower and nerdier as we go along in the process. **Lenny Rachitsky** (00:14:45): Awesome. In the experience of my podcast logo, I was an ass. At the end of it, I'm like, "No, this isn't right," because we narrowed, narrowed, narrowed, and then I was like, "No, I'm not feeling it," and then we unnarrowed it and went back. [inaudible 00:15:02] **Jessica Hische** (00:15:01): That is not an uncommon experience though. This is why there's a few things that I'm not opposed to that I know people that are very opposed to. I'm not opposed to Frankensteining options together. To me, it's like I'm giving you a menu of all the things that we can do, but I'm like a chef that puts a menu together where you can combine different appetizers and different mains and they all still make sense. Some people will give you a menu and if you try to do that, it's insane and it tastes terrible. But for me, everything that we're doing, I feel like, mixes and matches fairly well, and I will let you know if it doesn't. **Jessica Hische** (00:15:37): It's not unreasonable for clients to go down one path and then use that as validation or confirmation that something that we did much earlier was actually the right way. In that way, if a client ever asks me to do something, they're like, "Let's see it in purple or whatever." There's designers that will really fight you tooth and nail, because they're like, "That is wrong, that is wrong," but I know that some people just have to see it before they can let it go. Sometimes you have to walk down a path before you're able to understand what the right thing to do was all along. **Lenny Rachitsky** (00:16:10): That's exactly how it felt for me. Going back to the goals, the different goals people have when they're exploring this, you mentioned there's just little problems with the logo, it doesn't scale, it doesn't print well, that kind of thing. Another goal is people are pivoting and they want to change the vibe and the feel of the brand. What other goals might appear that you've come across why people want to do this? **Jessica Hische** (00:16:31): Well, sometimes there's a legibility issue that is really glaring once you see it and then people are too close in to notice it, so this is why it's like you have to show it to a lot of people that aren't familiar with looking at those letter forms and stuff. The one that came to mind immediately when you asked was when I did a refresh for Jeni's Ice Cream, which is a really amazing ice cream brand based out of Columbus, Ohio. They had a few utilitarian things in mind. They had this long J that created this pocket of white space underneath it that made it really hard to design with, but then the biggest glaring one was that they decided to make the apostrophe of the Jeni's over the I as a cool thing. It made the word look like it said penis because of the way that J was drawn. **Jessica Hische** (00:17:18): It had a little loop at the top of the J. That was the most specific fix that I've ever had to do, is make the logo not say penis anymore. But yeah, I feel like a lot of it is misreads. When you think about logos and things like that, you want it to be something that, at a super fast glance, people can read it right away. That doesn't mean that everything has to be simple, but it just means that everything has to be incredibly legible, especially when you're starting a new company or you have a less recognizable brand. Because eventually, you become a household name and then people can look at just the color and recognize that it's you or whatever, but it takes a long time building equity before you get that. Until that, it's really important that the legibility is just super tight. **Lenny Rachitsky** (00:18:04): Let's talk about actually thinking through my new logo and brand. Can you just talk about what you had in mind as you started to explore directions and we started narrowing what was the mindset, and the approach, and the vibe? **Jessica Hische** (00:18:18): I think with the Lenny's brand, you are what I would call a person that has a beloved fan base that we don't want to exclude or offend by shifting gears super crazily. When I was looking at redoing your brand, it was about what's here that we can look at that we should keep or at least explore keeping in order to make sure that it still feels the same on the other side? We didn't want to do anything super drastic. Some of the things to think about in that way are you have this sort of handwritten approach to a lot of the parts of your brand, and I was like, "How do we do something that feels handwritten, that feels like it could jive with the handwriting scripts and stuff that you were using but might feel a little bit more refined moving forward and in a way that could blend with illustration so that the illustration and the letter forms all feel like they were created by the same hand?" **Jessica Hische** (00:19:17): A lot of times for me, when it comes to doing an exploration like that, it's about how do we make sure everything feels like it was created at the same time and not that we just tacked on new things? Figuring out how to blend everything together is important. Color was also a big one. I feel like people's color stories are something that is an immediate read, where if you blur your eyes and look at a brand, you can recognize it by its color, and so I think keeping your color similar was a big one too. But then I really wanted to try different approaches with the typography, doing stuff that was a little bit more clean, doing stuff that still had a bit of a funky edge to it. Because your original Lenny's podcast type had this sort of cut papery, a little bit off kilter vibe to it, and so trying to capture that but with new cleaner typography. That was really fun. **Jessica Hische** (00:20:13): I was using a typeface Degular as part of it, which has a nice wonkiness to it. It was drawn by a friend of mine, James Edmondson, who I love all of his stuff. That was one of the things that we approached because I felt like it could capture the look of the original cut paperesque type. But yeah, it was really fun to try a lot of different things and work within the iconography that you had used on a few stuff with the microphones, and also marshmallows, and campfires, and all kinds of things, and just trying to make a more unified system. **Lenny Rachitsky** (00:20:47): Are there things that didn't work as you tried to explore this process that you recall, that might be worth sharing of just like, "Oh, that was a cool concept," but didn't quite work the way you thought? **Jessica Hische** (00:20:57): With working on this refresh, so much of it was thinking about what are the immediate uses of the logo. Your logo, you have these very specific uses that you need it for, the avatar for the podcast being a top one. Some people, they'll design a logo and then have these illustrative versions of the logo that get rolled out for other things, but I feel like those layouts were actually more important than even just having a basic letterhead-esque logo. That's an interesting way to approach it, because usually, it's like let's start simple, and expand, and make it crazier. I felt like we had to always keep those things in play, so it was designing brand assets while also designing the logo. Sometimes you'll see examples of that in early explorations just because it makes it feel real to the client. **Jessica Hische** (00:21:53): That's why there's always the tote bag. You got to put the logo on the tote bag and then it feels real or whatever. But in our case, we had really specific uses that needed to get explored very early on, and that made it a slightly different process for me. In terms of things that didn't work though, I think just trying to work on the level of detail within the illustration and type so that it could shrink down, because we knew... One of the primo examples of the logo being used was on that podcast avatar, and some of the versions felt a little bit too detailed to shrink down that much. Trying to get the balance of that, having the illustrations feel illustrative and whole, but not when they scaled up, to feel too simple like we just pulled it from a icon library. I think that was an interesting challenge. **Lenny Rachitsky** (00:22:46): One of the impetuses for changing my logo, for motivating me, is my wife's a designer, as you know. She's got strong opinions about my logo, and she always was making fun of my logo saying it looked like a clip art fireplace that anyone just could just plug and play. She's always like, "Oh, that's so bad. You got to change it." That was one of the motivators. I think I might have shared that when we started working together. **Jessica Hische** (00:23:08): Yeah. Also too, I think that really talks to what I was saying earlier about making sure that everything feels like it was created together rather than it feeling like these disparate elements, because I think you can have an icon or logo that is quite simple as long as the rest of the brand matches that simplicity. I think, for you, the biggest thing was making the illustration and the typography just feel like it came from the same universe instead of feeling like these separate elements. When I first moved to San Francisco, I moved to San Francisco from New York, and as a New Yorker, I had an apartment with a full kitchen that never got used. I just ate at restaurants and did takeout for the seven years or whatever that I lived in New York. **Jessica Hische** (00:23:51): Learning to cook, at first, when you learn how to cook, it's like you're making a pot full of ingredients and none of the ingredients are actually working together. But then the more you do it and the more you understand how these things are meant to blend and cook at different temperatures at different times, you start having this cohesive dish rather than hot ham water. You know what I mean? I feel like a lot of clients come to me and they have hot ham water when it comes to their brand. It's just about turning that into a soup, something that feels real. **Lenny Rachitsky** (00:24:25): I want to take a quick tangent. Most people listening to this podcast are not designers. They're product managers, founders, engineers, and folks building product. I've always wanted to see the world through the eyes of a designer, because there's so much I don't see and there's so much that affects how I think about something that I don't understand when I look at a logo, and so I thought it might be helpful just to spend a little time helping people see a designer a little bit. Let me just ask you this question. When people look at a logo or a brand, what are just elements that make it what it is, that make you feel the thing you want to feel that we may not recognize? **Jessica Hische** (00:25:06): I think most people are better at understanding the feelings and sensations that typography and logos give us than they give themselves credit for, because what we are as people are endless absorbers of patterns, and information, and all this kind of stuff as we move throughout the world. We don't take time to sit and digest it, but it's still coming in and getting logged. That's why if you see something funky in the world, you're like, "That's weird. I don't like that. I don't know why I don't like it, but I know I don't like it." I think even as a non-designer, you can see that in typography. The whole being able to recognize patterns thing, I talked about this a bit at config, it's like it's a safety thing. Looking into the world, your eyes can spot that thing that's a little bit off, and that thing that's off feels not safe to you. **Jessica Hische** (00:26:08): It's thinking about when we look at a meal and there's a thing on the plate that looks like it's moldy or something like that. You understand that doesn't look right to me, this doesn't smell right to me. Your body knows it before your brain knows it. Even as a non-designer, I think you can look at examples of logos where something's not quite right and be like, "Something's not right here, I just don't know how to name it." But I think a good exercise is just looking at fonts that are available in the world and asking yourself, "What feeling does this give me?" and just write them down. It doesn't matter, just give yourself permission to say whatever is happening in your mind, the first thing. Don't overanalyze it. Just look at it and be like, "That feels calm to me. That feels exciting to me. That feels whatever to me." **Jessica Hische** (00:27:00): The more you do that, the more you can start seeing similarities in the ones that feel exciting, and the ones that feel calm, and the ones that feel whatever, and then get into analyze mode of, "Oh, these 10 things that I said feel calm are a lighter weight, have more generous spacing, have rounded edges, have rounder bowls to the letter forms." You just start seeing commonalities between the things. It's just about seeing them all together to understand what those similarities are. I think anybody can do that. I mean, you're not going to have the language of the leg of the R and the tittle of the I. Don't worry about that. You don't have to know typography language to think about it, but anybody's capable of doing that. It can be really fun to just stop and ask yourself and notice. **Lenny Rachitsky** (00:27:58): This is great. I want to go actually a little deeper. What I'm hearing is look at something, tap into the feeling you feel when you look at it, actually pay attention to it because there's wisdom in that. The specific things that you pointed out that impact that feeling are, you mentioned, spacing between the letters, the edges. I imagine there's just the color of it. What other specific elements impact the way someone feels when they look at a logo? **Jessica Hische** (00:28:26): There's the width of the letter, so if it's really narrow versus really wide. I always think about the width, the weight, [inaudible 00:28:35] facing, sort of detailed treatment of things, whether things are very hard and jagged or soft and how soft it is. Sometimes we just add a tiny bit of softness so that it just feels printed. You can take a typeface like Helvetica, just the one everybody knows. But if you take Helvetica and just ever so slightly round the edges just a little bit, all of a sudden, you have this typeface that feels more vintage, or softer, or whatever, because we're perceiving it, we would perceive it if it were printed on paper versus perceiving it as this hard geometric piece of technology that we're viewing. You know what I mean? **Jessica Hische** (00:29:20): I know that it's because when you look at stuff printed on a page, it bleeds into the paper a little bit, which means that that softness reminds us in our bodies of a thing that we've seen that was printed. It's cool to sort of walk back your feelings also. You'll look at something and go, "That feels like this," and then ask yourself why does it feel like that. It might be because you saw it on a flyer for a band when you were 22, and it brought out that feeling in you of what it felt like to be 22 at that thing. That's a very specific feeling to you, but it can inform your decisions about design, because you can be like, "Oh, I'm not that much of a special snowflake." Other people might have that same reaction but have different experiences that are adjacent to that reaction. **Jessica Hische** (00:30:08): It's cool because you are reverse-justifying decisions. I think that's a really fun exercise to do, is to Song Exploder your intuition. You make a decision intuitively or look at something and intuit what you feel from it, and then really try to dive in, "Why do I feel that way? What could this have reminded me of that made me feel that way?" You have to be just so forgiving and loose with yourself as you do it because then you'll get into some really weird stuff, and that's really great inspiration juice for picking other things. **Lenny Rachitsky** (00:30:51): I love the exercise that you gave. The one you gave earlier is look at a bunch of fonts, look at your font folder. Is that a place to go, just open up your font folder and just go through them? **Jessica Hische** (00:30:55): Totally. Look at your font folder, or go to MyFonts, or a place where there's a ton of fonts, and just search for something. Search for sans serif or whatever. Search for a really basic category of fonts. Serif, sans serif, script, whatever, the top level edge of stuff, and then just page through, page through, page through. Screenshot stuff that you like and make a folder full of screenshots, and then you can take those screenshots and start categorizing them. "Oh, this one feels feminine. This one feels masculine, this one feels aggressive. This one feels whatever." Just take some notes on it. Then, you ask yourself, "Well, why did I feel that way?" You're like, "Oh, well, this feels feminine because it reminds me of wedding invitations," and wedding invitations feel inherently bridey versus groomy. All of a sudden, you're like, "Okay. Well, now I know that if I'm going to use a script for something, this zone of script feels very wedding, so maybe I avoid that for this brand that's actually a cutting edge food packaging company or whatever because it feels too aligned with that industry." **Jessica Hische** (00:32:10): Stereotypes are real and trends are real, and what can sometimes happen is some industry usurps an entire style for a period of time. If you use anything within that style, it's like you're aligning yourself to that industry. I mean, everybody that does branding, one of the things that they do is they analyze the competitors of the company. You just look at a landscape of what are all the competitors doing, what is their visual vibe, and do I lean into that or do I avoid that? If I lean into it, then I'm immediately getting this... Everyone that looks at it understands I'm a FinTech company because I look like a FinTech company. If my whole thing is I'm trying to be divergent from that, I'm trying to show how different I am from the status quo, then you use it as a reactionary thing of I want to do nothing like that and do something really different so people understand this isn't just another FinTech company. **Lenny Rachitsky** (00:33:09): Yeah. I'm thinking green. The color green has to be a part of the logo if you want to be a FinTech company. **Jessica Hische** (00:33:13): Yeah, exactly. If you're trying to be weird, then you're like teal. **Lenny Rachitsky** (00:33:19): On this topic of seeing a designer, is there any other tip, just before we move on to a different topic, of just how someone could learn to see a designer a little bit more? **Jessica Hische** (00:33:30): Yeah. Another thing to notice, because I'm assuming you're... Product people, I feel like a lot of product people end up having some engineering background, whether or not they're engineers themselves. They have to interface with the engineers and they build stuff, and so they come at it from a data standpoint. I can always tell when there's an engineer that has suddenly got taken an interest in type design and is now a type designer, because everything is very, very regular. You can draw a grid on top of everything and the lines all line up perfectly. You see lots of reverse justification of that when people are making logos and they have a more engineering background. The thing to notice, that is interesting within type, is that, yes, you're absolutely following rules, but you're breaking those rules quite often to correct for optical tricks. **Jessica Hische** (00:34:24): If you look at a geometric sans serif, for instance, that's like a category of sans serifs, and they're meant to have a lot of really strong geometry, be very regular, like most of the sans that you think of that you're like, "I'm in love with this over the last 10 years," like geometric sanses. But when you really start to examine them, you notice that there's all these little things that people are doing to make them look perfectly geometric even though they are not mathematically perfectly geometric. That's another thing that you can do, whether you're doing it in Figma or doing it somewhere else, is just type out a couple of lowercase letters. Lowercase specifically are really good for analyzing this because they're smaller than the uppercase letters. You usually have to accommodate for the weight a little bit differently. You'll notice that when strokes combine, so say I have an A and I'm combining the lower bowl of the A, I'm going to get a little thinner as I come into that. **Jessica Hische** (00:35:23): Or say I have a two-storey A, so a two-storey A is the one that's like this and then a bowl, you might notice that this vertical of the A there, the bowl actually eats into that stroke a little bit to erase a little bit of that added weight that would've been perceived optically had you kept everything perfectly regular. It's weird because you end up creating something that's perfect and then have to make it not perfect in order to make it be perceived as perfect. That's another just fun thing to start noticing. You notice it a lot more on typefaces and typography that is heavier in weight, because when things are heavier weight, you're constantly managing these really inky moments where things join together and you have to subtract a bunch of weight from that so that it doesn't get perceived as this dark mark where the letter is happening. **Jessica Hische** (00:36:22): I think about lowercase Rs and lowercase Ns, where the shoulder of the N or the R comes out, sometimes the top of the R is actually narrower at the top than it is on the bottom, and that's to try to subtract some of that weight in there where that join happens. Anyway, that's just a fun thing to notice that you have to do that. Once you start seeing it, you start seeing where it happens more often, and the answer of why it happens is because correcting for this optical weight issue. You're like, "Oh, man. Now I have x-ray vision. I can see all these weird things I've never seen before." It's very fun. But anyway, a lot of people, when they first start out doing typography, whether you're an engineer or whether you are a designer, they don't account for that. I can always just look at something and see whether someone is truly an expert at typography or whether this is a fun hobby for them when they're pretty fresh at it. **Lenny Rachitsky** (00:37:20): The exercise here is open up Figma, start typing, and make it really big so you can basically see the font really zoomed in. **Jessica Hische** (00:37:20): A single letter. **Lenny Rachitsky** (00:37:27): A single letter. **Jessica Hische** (00:37:28): Make a single letter the whole page and then just draw some vertical lines, or do the thing where you draw a little circle or whatever and see if that circle is the same size at the point where two strokes join together or the point where the stroke is just vertical and on its own. You'll notice that there's differences even in typography that's meant to look extremely rigid and geometric. **Lenny Rachitsky** (00:37:53): I want to come back to my logo just to close the loop there. Talk about just the final result that we landed on, and why you think that was the final answer, and what you think people might get from it, whatever comes to mind. **Jessica Hische** (00:38:07): Yeah, totally. I think the final answer or the final logo, we took it down a lot of different paths trying to see where it was going to land, but ultimately ended up keeping it pretty close to home and really focusing on that asset of the fire. We tried so many different versions of it's microphones with the fire and marshmallows with the fire, et cetera. It was just about sometimes the simplest solution is the correct solution. I don't know, I just feel like in terms of what we were doing for blowing it out and making it really cohesive, we went a lot of directions where there might've been multiple versions of the logo depending on the scale and ultimately ended up in a place where it's much more in line and consistent across the bar. **Lenny Rachitsky** (00:38:55): Yeah. Maybe what I'll do is we'll share, I don't know if you're comfortable with that, we could just share all the iterations somewhere that we went through. **Jessica Hische** (00:39:01): Oh, yeah. I love sharing iterations. It's very fun. Yeah. **Lenny Rachitsky** (00:39:03): Okay, cool. Sweet. The biggest issue we had with the podcast logo specifically is, originally, I was thinking the mic made sense to differentiate it from the newsletter. At the end of it, it's just like, "Why do we have this freaking mic in there? It just feels strange." That's where we revisited the whole idea and killed the mic and went back to a different version of the fireplace but with marshmallows. **Jessica Hische** (00:39:24): Yeah, I love the marshmallows. **Lenny Rachitsky** (00:39:26): Awesome. I love it. That was my wife's... My wife loves the marshmallows also, and it's so versatile. We can use it in so many different ways. **Jessica Hische** (00:39:33): Indeed. **Lenny Rachitsky** (00:39:34): I guess maybe one last thread there is we explored handwritten typography that you created from scratch, and then there's the block letters. Maybe just thoughts on those two options and benefits and why go one direction versus another? **Jessica Hische** (00:39:51): The handwritten one, I really liked because I felt like we could bring the line quality of the illustration into the handwriting, but then the only problem with the handwriting is that if you want to blow that out, if you want to include other handwriting throughout the rest of the brand, finding something that matches that perfectly without creating a custom typeface is a whole thing. I really like being able to combine the two, where we have this broader visual vocabulary that we can pull from, because you're going to have headlines, you're going to have subheads, you're going to have all these other uses for typography moving forward. If you just have one thing to pull from, it's a lot harder to work with. It's just nicer when you have a few elements to play with. It's like having a wardrobe. If you have only one shirt and one pair of pants, there's only so many things that you can do. But if you have all these things that work together and can recombine, then you can blow out a brand system much more easily. **Lenny Rachitsky** (00:40:44): Yeah. That's one of my favorite things about working with you, is you create all these different variations of ways to use it. It doesn't always have to be the handwritten one. It could be the blocky outlining one. It's not like, "This is it, don't change anything about this. This is the only way to use it." **Jessica Hische** (00:40:57): Well, part of that is because some brands, if you have a massive company, like hundreds of employees generating hundreds of things, sometimes having too many assets can overcomplicate stuff. Because unless you have a really, really well-written brand book outlining how to do everything that people are adhering to very closely, you can get the assets running rampant throughout all of the stuff and being used incorrectly. But because you're not a massive company and you have creative control over the things that are happening and can help direct that, we can be much more playful with the assets and give you the ability to use things in different ways. It depends on how much you trust all the people that are handling your assets. **Jessica Hische** (00:41:43): I am of the mind that you shouldn't need a 500-page brand book in order to direct how the brand is used moving forward, and that if you do, the brand might be quite complicated, or there might be even just parts of the logo that make it difficult to work with. My goal always when designing a logo is to design a logo that's so easy to use that you don't have to be an extremely skilled designer to design well with it. That's my number one goal, because I know not everybody is going to be at a stage where they have an internal brand team or a designer that's a rock star designer that can work with really complicated assets and make them look good. **Jessica Hische** (00:42:28): I just want the assets to teach you themselves, by just how they exist, how to use it. You, as a person that has any taste whatsoever, and hopefully people that you're hiring for any job at your company have some degree of taste. If you hire an engineer, they have to have taste about how that happens. If you hire a marketing person, they have to have taste about how that happens. They should be able to look at that and intuit most of the way that you should be able to use it without being explicitly told, "Do not do this." **Lenny Rachitsky** (00:43:01): **Jessica Hische** (00:44:31): Yeah. Well, there's different companies. There's companies where brand is literally everything, where they're doing something that's not crazy innovative in the first place and the brand is the thing that is the whole company, and that's fine. That's a completely valid way to do stuff. It's like people that can take in information and recommunicate it in a way to another audience or whatever that they hit that audience in a way that the original information couldn't do. Think about all of the people who write books on psychology, and medicine, and all kinds of stuff that write it for a broader popular audience. They're the ones reading the medical papers, they're the ones digesting all of this really huge complicated data, and turning it into something that normal people can read. I think that there are companies that are doing that. They're taking a thing that is not innovative or isn't like they're not the only ones doing it, but they're repackaging it in a way that takes that and makes it so accessible to so many people. **Jessica Hische** (00:45:34): In that case, brand can matter immensely, where the brand really is the thing that shows people that the thing that you're doing has value. But for a lot of people, the brand should be somewhat invisible so that the thing itself becomes the star. If we think about the experiences that we have using products, sometimes there's products where there's a ton of fun and delight built into how you use it, and that can happen through brand through design choices and things like that. Sometimes the delight is the fact that nothing is getting in your way as you're using that product. You just figure out what's your ethos of your company. Is the whole thing about doing a thing well, doing it simply, and making sure that everything gets out of the way of that experience, or is it like we're trying to generate this delightful thing or we're trying to open it up to a new audience or whatever? Depending on whatever that goal is, brand can have a different place in that equation. **Lenny Rachitsky** (00:46:42): I think some of this unique perspective on the power brand and the need for it in tech companies comes from you're not like a tech person. You work with tech people, you work with tech companies. Do you feel like that has an impact on the way you think and the value that you bring to companies to give them this very outside perspective? **Jessica Hische** (00:47:01): I mean, most of the folks that I know that work in brand or traditional graphic design, print design, they don't necessarily have a lot of insight into how building companies works. They're not friends with a ton of startup founders and things like that. I've just had been in this very fun position being like everyone's token creative person in The Bay for a while, and this been for a long time. I remember speaking at a Silicon Valley event that was women in Silicon Valley in 2009 or 2010, something like that. It's interesting to be a person that has never actually, themselves, worked at a tech company but felt so involved and understanding about how all of that works. My partner, the reason why we're in The Bay is because he got hired by Facebook back in 2011. We were olds at the time. Take that with a grain of salt, don't judge me. **Jessica Hische** (00:48:02): Because we were 28, 29 coming over to work at Facebook and everybody there was 23, 24, and so all the people that we ended up meeting in The Bay were more people our age that were moving on to start companies and things like that. We just got to see that perspective so clearly of what it is to branch out on your own, to fundraise, to do all this stuff, to pivot, to do little experimental apps and see where that goes to get acquired as a team versus getting acquired as a technology or whatever. I've been able to see that in a way that I feel like a lot of people that do my job don't get to see. That makes me very sympathetic and towards what it is to want to build a brand as a founder. I understand that you have limited resources and those resources aren't necessarily going to get devoted to doing a $200,000 brand exploration, because when you have $500,000 of money at all for a year to try to get things going, you certainly should not spend half of that money on branding. **Jessica Hische** (00:49:12): That's my opinion, but that's not to say that brand can't be important and can't come in at some level or can't be thought of as a partnership between you and someone else where... There's this whole idea of fractional leadership now, which I feel like hasn't really infiltrated my world as much, but I don't know why it hasn't, because most people don't have internal comms teams, internal brand teams, until the company is very mature. The idea that you could bring someone in who is a real expert in whatever it's that they do, just as you need them, and they just get consultant equity kind of thing, that should be more present because people don't necessarily need to have internal brand teams for the first six months to a year of when they're doing stuff unless they grow really significantly. **Lenny Rachitsky** (00:50:05): Along these lines, you have a pretty unique way of pricing your work. For people that may want to explore this with you, share whatever you can about just how you think about pricing and ideally even an order magnitude of pricing so they're like, "Oh, okay. We should actually do this." **Jessica Hische** (00:50:21): To go back to the process how it's always about figuring out what people are trying to accomplish, so a lot of my process scales depending on how broad of an exploration that we're doing. The way that I treat it is I treat my branding work not dissimilarly to how I treat commercial lettering, which is atypical. Brand people, what they typically do is because the client has to own the assets outright at the end no matter what, they tend to do is bill everything that the client owns everything as you are moving along. It's all sort of work for hire, but the idea being that it's a buyout of everything that is being made. What that means is that when a branding agency is pricing stuff for you, they're taking the buyout rights and baking it into every round of work so that every round gets more expensive because you are owning all of the work. **Jessica Hische** (00:51:14): What I do is I treat it much more like a commercial lettering project where I say, "You have to own the rights to this eventually, but hey, let's break that out and let's keep the creative process lighter and less expensive so then we have more room to explore. So then if some stakeholder comes in last minute and blows everything else up and we need to start over, you haven't already paid to own everything that we've created, you just pay to own the thing that we create in the end that gets chosen." I really like the idea of keeping the creation process more flexible and to try to scale to what people need versus having a really rigid way of approaching everything. Sometimes people will bring me on really early in the process, where if they have an internal team or if they're working with an external agency or something, they want me there from the get out. **Jessica Hische** (00:52:04): Some people are like, "We have no money and we are going to try to do this as much as we can inside of our business, but then can we hire you at the end to make it look good? If we can get everybody bought in and get it 80% of the way there." Depending on what people's budgets are, I have different ways of working, or just depending on what their needs are. Because my whole thing too is I don't want to step on anybody's toes, because sometimes companies have these really amazing designers that are working in-house, and it sucks as a designer who started at a company and thinks that you might be able to get a chance to work on what is considered the most important asset in terms of the brand and they just farm it out to someone else instead of letting you touch it. To me, that's a recipe for anything that I create to be immediately killed, because someone inside is going to be like, "It's time to shine," and then they're just going to kill all my work. **Jessica Hische** (00:52:56): I'm always like, "How do we collaborate? How do I make it so that I'm an asset to you? Not that I'm trying to step on your toes, not that I'm trying to take over what's the cool juicy work from the people who inside that are really excited to do it." I just want them to feel as bought in as I can be. But yeah, it becomes interesting. I feel like I get told by branding people that I'm too inexpensive because they're like, "Oh, for what you do, it should be 60 or $70,000 at a minimum to do all this kind of stuff." I'm like, I feel like the majority of the projects that I do end up being between 25 and 35, but depending on how you bring me in, it can be less if it's just as a consultant. It's not out of the realm of possibilities to hire a proper crazy expert at stuff. It's not like you're thinking about sinking half a million dollars into the brand. That's a very different experience. **Lenny Rachitsky** (00:53:51): Awesome. Thank you for sharing that. Before we get into other stuff that you do, because like you said at the top, there are many other things you do outside of this specific time of work, is there anything else you think might be helpful or important for people to know about working with you on a logo refresh or just thinking about logos and this whole space we talked about? **Jessica Hische** (00:54:11): The best thing is just seeing what's there and really being able to understand what's not working about it and what your goals are. Like I said with that reverse justification of intuition, I think if you know that the logo is not quite where you want it to be, just spend a couple days asking yourself why. "What is the thing about this that bothers me?" Don't get specific. Don't be like, "The way the R is," or whatever. Maybe that's the thing that we talk about down the line, but always think big picture before you think minutiae, because sometimes people think that... They'll throw a bunch of minutiae stuff at me, but it's because they haven't really stopped to think about what is the overall thing that's bothering them. **Jessica Hische** (00:54:59): You just never get there if you're always trying to address detail before you address the big picture stuff. You have to just always start super top level, and really ask yourself very broad questions about why you think it's not working, and then go tighter, and tighter, and tighter, and be like... It really could be like, "This C has always bothered me," and then we can get real specific about that when I'm doing the refresh. But I think I also need to understand the overall reason why we're doing this, not just the little bugaboo that bothers you specifically but might not bother anybody else. **Lenny Rachitsky** (00:55:35): Yeah. When I was thinking about this, it feels like my whole feeling was this could be better. That's all it was for me initially, is just like I feel like it could be a lot better. I imagine that's enough for some people, just like, "I think this could be better," and then here's things [inaudible 00:55:50]. **Jessica Hische** (00:55:49): Yeah. That's definitely enough for some people, because I think sometimes... I think you, specifically, had a very clear vibe going on with all of your brand stuff. Some people, it's totally like a mishmash grab bag of random trends and there's no real voice that's coming through. But I feel like you've been doing this for a while, and when you see everything together, there's definitely a very clear vision and vibe that you get from everything. I always tell people that having terrible vision can be your best asset when it comes to logo and brand, because it allows you... **Jessica Hische** (00:56:30): Just take your glasses off if you have terrible vision, and look at it, and get the feeling when you can't see the detail. You have to be looking at it with blurred eyes. What is the overall look of this thing? Just trying to get as broad and noodly as you can with it instead of it being about those really specific one by one stuff. I think when you blur your eyes on your brand, there was a really clear cohesiveness to it already. It was just about massaging it into a more consistent professional-looking place. **Lenny Rachitsky** (00:57:07): Well, I can't look at the old logo anymore now that I've gotten this thing coming together, so I'm really excited for this to come out. Just a couple closing questions. One is you have a lot of other stuff going on that is not just typography and logo refreshes. You have children's books, you do lettering for classics, you have a store in Oakland. Talk about all these other things you got going on in case it might interest people. **Jessica Hische** (00:57:32): Sure. Yeah, of course. I'm based here in The Bay, as we've talked about, and I have a studio in Downtown Oakland. My studio is like Barbie's creative Dream house, where the top floor is my office, that's where I'm right now, and then the bottom floor on one side is a workshop. I do a lot of printmaking. I went to college at a school that was very focused on interdisciplinary work, and I feel like I bring a lot of manual analog processes into my work a lot. I find it really important to make physical things as a part of my creative process, so I do a lot of printmaking. On the other side downstairs is a brick and mortar store. I've always wanted to have a brick and mortar store because, as an artist, I think having people have a physical connection to your work can be really important. **Jessica Hische** (00:58:20): I think one of the reasons why people hire me to do things for them is because one of the gifts of working with someone that is a real nerd professional about whatever it is that they do is that they bring you along the journey and give you the language to talk about the thing through their eyes and through their experience. To me, the funnest thing for me is actually telling clients and teaching them about all the things that we are doing along the way so then they go out into the world as a newly-minted type nerd and can communicate all of these things to other people. That connection is just really important. The connection to the work, the story behind it, I feel like that's one of the ways that we create lasting work, is understanding that the work exists because there's a story behind it. Things, if they're just created because of the aesthetics or they're just created quickly or whatever, it's really easy to discard them because there's not a story behind it. **Jessica Hische** (00:59:22): But if you think about all the objects in your life that have followed you throughout your life, what's a thing that you've had since you were in fifth grade or whatever that is still magically in your possession in your house? You have that because the story of that thing is so important to you. I think that the work that we create, the design that we create, can have that. It can be imbued with so much story and meaning, that when we think about moving on from it, we're like, "Ugh, but this." I think that's one of the ways to build a lasting brand, is to just make sure that the story of creating it feels so real, and visceral, and important. The store is a way for people to have a physical connection to other work that I create, like the prints and things like that. **Jessica Hische** (01:00:07): With the kids' book stuff, that's also about creating lasting stuff. I like creating physical things in the world. I like repackaging things that I've learned in therapy in a way that kids will appreciate and enjoy. I'm just always thinking about what's a way that I can say a thing that has been said before but hasn't been said in this way. If I can turn that into a physical object that people can have and appreciate, all the better. But yeah, I don't know. While, professionally, what I do is considered very niche, I feel like all the things that I do are quite diverse, because they tickle different parts of my brain. I have to use my hands in different ways and my mind in different ways. It's how I've been able to generally avoid feeling burnt out as a creative, is just being able to move on between different kinds of work and just feel excited about different things at different times. **Lenny Rachitsky** (01:01:05): For folks that want to maybe check out the store, how do they find it? It's called Jessica and Friends, is that right? **Jessica Hische** (01:01:08): Yes. It's called Jessica Hische and Friends. **Lenny Rachitsky** (01:01:10): Jessica Hische and Friends. **Jessica Hische** (01:01:13): You can just Google JH&F. **Lenny Rachitsky** (01:01:14): Google Maps, yeah. [inaudible 01:01:17] **Jessica Hische** (01:01:18): Yeah. I put JH&F on as a part of the Google Maps name so I don't have to spell my name to strangers, because I have a weird German spelling last name. I also have a second store called Drawling, which is drawing with an L thrown in there. That one is an all-ages art supply store that's sort of a kids' art supply store. That one grew out of JH&F as well. Those two stores exist. With my books, if you just look up my last name on any of your favorite booksellers, you'll find me. **Lenny Rachitsky** (01:01:49): Last question. I'm just going to throw this out there in case something interesting comes up. We have a segment on this podcast called AI Corner, where I like to see how people have found ways to use AI in their work, in their life to be more productive, do cool things. Is there some way that you've found a way to use AI in the work that you do that makes you do more interesting stuff? **Jessica Hische** (01:02:09): A little bit. I am in this really interesting position in terms of AI where my partner works at Meta on GenAI stuff. He's a director on the GenAI team at Meta and is very bought into AI as a whole thing. I am a little [inaudible 01:02:28] about its impact on a lot of the things that we do. I think, overall, it will become a tool and be very useful, especially in a lot of different fields. But I think this timeframe in which it's more novelty is going to have not the best impact on things like illustration, but eventually, we'll all come out of it and it'll be fine. In terms of how I've been able to integrate it into my process, I did some work for Salesforce last year where the theme for Dreamforce was going to be very AI-driven. I felt like I needed to explore AI as a part of the generative process for creating that art. **Jessica Hische** (01:03:08): I did have fun creating custom lettering and then trying to run it through stable diffusion to get stable diffusion to generate instances of my lettering in different styles. We were making these clouds. We ultimately didn't end up using it, but it was still really neat to see. I could see the validity of that in the creative iterative process. I think the biggest thing for me is that I find that the sloggy, slow dregs of work is very fulfilling to me, that a lot of the evangelists of AI are like, "Oh, imagine if you could spend all of your time high level thinking, and coming up with the concepts, and guiding the vision, and whatever, and then just get AI to do everything else that you don't care about." For me, that just sounds like not the most holistic approach to how I work, because the reason why I do all the things that I do and why my process is the way that it is because while I love thinking and I love coming up with conceptual stuff, I find it to be very cerebrally taxing. **Jessica Hische** (01:04:17): I need a break from that by doing the more low-key production end of stuff. That's my favorite part of the process, is we know what we're doing, and now it's just about going in. When it comes to judging logos, for instance, the days that I spend knowing exactly what I'm going to do and all it is me just moving little Bezier handles around and getting it feeling right and whatever, those are pure therapeutic zen for me. I think I will always have that as a part of my work and will probably not have AI be outputting that part. But I have been able to have it be helpful in the iterative process a little bit, both through generating sketches with that project and then also through a lot of stuff with writing with my kids' books and things like that, is coming up with lists of words and concepts that are adjacent to each other, whatever. **Jessica Hische** (01:05:17): I have found that Claude and ChatGPT are very good for things like that. I'm working on another kids' book now, and I'm trying to think of the directions that it can take. One of them is sort of illustrating different feelings and things like that. I could sit there and brainstorm what are the different emotions or whatever, or I can just ask Claude like, "List 50 emotions," and then I can cherry-pick the ones that come up that feel right. I do find it's really good for that early brainstorming stuff, and that's been really nice. **Lenny Rachitsky** (01:05:50): Is there anything else that you want to share or leave listeners with before we get to our very exciting lightning round? **Jessica Hische** (01:05:58): Yes. Well, I do have a new kid's book coming out in October. **Lenny Rachitsky** (01:06:02): Oh, [inaudible 01:06:02]. **Jessica Hische** (01:06:02): Aside from all the logo stuff, please do check out my kids' books. It's called My First Book of Fancy Letters, and it is like a new spin on an alphabet book, but instead of it being an alphabet book for brand new babies, which you could totally buy it for brand new babies because it is very simple, and fun, and they'll like the bright pictures, it's for the age where kids can recognize letters but can't necessarily read and write yet because they get so into seeing letters drawn in these different styles and imagining what other letters could be drawn in. Each of the letters is drawn to represent the word that it sounds like. Letters can be athletic, bubbly, or creepy, and then it's like, "Well, what does a creepy C look like?" **Jessica Hische** (01:06:49): When kids are starting to understand letter sounds and recognizing letters, they can start thinking about what other words start with that letter sound, and then they start listing stuff out and become immediate over-the-shoulder art directors. It's been really fun showing it to other preschoolers, and TK, and kindergarten kids, because they're immediately like, "Well, R should be a river. It should be a river." I'm like, "Well, how do you draw a river?" It becomes this fun imagination exercise too, so definitely check that out. It's up for pre-order now and comes out October 22nd. **Lenny Rachitsky** (01:07:21): That is so delightful. I know you have multiple kids. Do you start to see the idea with one age of kid and then by the time the next kid reaches that age, it's ready and published? Does that work timing-wise? **Jessica Hische** (01:07:31): Yeah, the only thing is both of my... Well, my oldest child is a real super reader. She's always ahead of the game. The second that she could read, she was like, "Oh, picture books are for babies." Now she's reading, she goes into Pegasus books and is just like, "Where are your books for teenagers?" They're like, "You're nine. We're not going to show you that, but here are the middle grade books or whatever." There is a little bit of that. You are a parent, but you are a parent of a very young person. Kids don't want to buy anything you're selling as a parent. There's a little bit of that where I feel like I get so many wonderful letters from other families about how it's their favorite book, and they read it every night, and it's so important, and then my kids are like, "Yeah, yeah. It's just mom's book, whatever." **Lenny Rachitsky** (01:08:23): Yeah, that's bittersweet. Well, with that, Jessica, we've reached our very exciting lightning round. Are you ready? **Jessica Hische** (01:08:30): I'm ready. **Lenny Rachitsky** (01:08:31): Speaking of books, first question, what are two or three books that you've recommended most to other people? **Jessica Hische** (01:08:36): Rick Reuben's creativity book is so good. Definitely recommend that. I haven't listened to it on audiobook. I read the physical book, but I also heard the audiobook is very zen. I feel like it's just a very good palate cleanser in terms of being an artist and creating because it feels both high level but also very actionable, so really recommend that. In terms of learning about and understanding typography, there's this book called Inside Paragraphs by Cyrus Highsmith. It's very small and very digestible. You can read it in one bathroom visit, and it's illustrated really well. It has cool illustrations. If you want to learn about some basics of type and typography, it's a really great book, and incredibly accessible, and not like reading Bringhurst or something like that, so big ups to that book. Oh, what's another book? **Jessica Hische** (01:09:33): I don't know. I feel like I'm just going to end up recommending all the books that I'm currently reading. This month, I read both Patti Smith's Just Kids, which I loved also and was also... I feel like I'm reading a lot of books about being an artist more so than being a designer. That book, I found really interesting, just hearing her story of moving to New York and having nothing. Just trying to be an artist, and make art, and having that be the thing that drove everything that she and Robert Mapplethorpe did. I don't know, I just feel like I'm looking for ways to get out of my very business-driven sensibilities around art making and get into a space that's more loose, and free, and driven by passions and feelings more so than necessarily career-based milestones and things like that. This is a wild card one too. I just finished The Emperor of All Maladies. I'm just a big fan of reading things about human biology and things like that and found it totally fascinating, so do read that one too. **Lenny Rachitsky** (01:10:40): I can't help but ask, how do you have time to read, raise children, work on so many projects, have a run a store? What is your secret? **Jessica Hische** (01:10:50): Well, you get pretty ruthless about your schedule when you're a parent, where when you're at the office, you are just heads in working, and so I think just trying to stay as focused as possible in that way. I do this thing where I bounce back and forth between projects a lot as I'm losing steam, and so having multiple things to work on keeps me motivated to keep working. I think it's kind of an ADHD thing, where I will start my day one way and then as soon as I start losing steam, I switch to a different thing, lose steam, switch to a different thing, lose steam, switch to a different thing. Rather than taking breaks, I just take a break by working on something that feels fresh. That can be super helpful. **Lenny Rachitsky** (01:11:35): That's an awesome tip. **Jessica Hische** (01:11:36): Yeah. I mean, it's incredible. I also would tell people when I had first started out, I had a full-time job and then was doing freelance in the evenings. People were like, "How do you not get burnt out, whatever?" It's because my day job was so different from my night job that it felt like I was doing two separate eight-hour shifts instead of one continual sixteen-hour shift. I think that's something to sort of think about, is that there's always going to be things that need to get done as a part of your work or things that you're interested in and passionate about. Just having enough diversity in what that means is going to allow you to maintain enthusiasm for doing all those different things for much longer. Actually, the more homogenous your life and career and job is, the faster you're going to burn out, so just making sure that you have enough variety and all the things that you do. **Lenny Rachitsky** (01:12:27): That was an awesome tip. I'm glad I went there. Okay, back on track to our lightning round. Is there a recent favorite movie or TV show you've really enjoyed? **Jessica Hische** (01:12:34): Severance was my favorite TV show I think I've ever watched. **Lenny Rachitsky** (01:12:38): The second season's coming out. **Jessica Hische** (01:12:40): I know. That came to mind because I knew the second season was coming out, so I'm just really excited about it, but I think that was probably tops for me. **Lenny Rachitsky** (01:12:48): Is there a favorite product you've recently discovered that you really love? **Jessica Hische** (01:12:51): Oh, yeah. Well, there's a few things. Well, there was one that's just a super random one that was just pure delight. There's a Japanese brand, Penco, and they make a lot of wonderful stuff. I carry a lot of their stuff in my store. One of the things I bought recently from them is a pen cup, a pencil cup. It's ceramic, but it looks like a paper bag, a lightly crumpled paper bag, and then it just has printed on it Penco, whatever. I just really like it when you take an existing object and give it a new form. I find that to be very delightful, and so that was, I think, one of the things that I really loved recently that I bought for the store. **Lenny Rachitsky** (01:13:28): Awesome. Pick two more questions. Do you have a favorite life motto that you often think about, come back to share with folks, find useful, and work your life? **Jessica Hische** (01:13:38): It's funny being a lettering artist because I'm not much of a quotes gal, all things considered. I should be because I could make a million dollars by just making "live, laugh, love" pillows or whatever, but I am not usually continually collecting quotes. But I was just at a conference up in Portland called XOXO, and one of the presenters showed a quote on the screen that resonated with me more than most things that I've seen in recent memory. I feel like this is my new... It was one of those quotes that I was like maybe I should get a tattoo of that. When it gets to that level where you're considering a tattoo, you're like, "Okay, that's official." It was "hope is a discipline". I just really loved that. It's by Mariame Kaba or Mariame Kaba. **Jessica Hische** (01:14:25): The idea that we have to choose to create positivity, that it's like a choice, and that in order to dream of these things, you can actually create structure and discipline around it, and that it's not just something that is just inherent and comes, you have to actually have a practice around being hopeful and positive. I just really liked that as a concept because I feel that way just about navigating through life, that everything that we do is a choice and that we can choose to frame things one way or frame things another way. Understanding that you have power in that, I think, is really important, and so I just really loved that. Hope is a discipline. **Lenny Rachitsky** (01:15:14): I really love that. I love any quote that inspires you to not feel like a victim, and gives you agency, and reminds you that you have agency over. **Jessica Hische** (01:15:23): Exactly. That's, I think, was the biggest thing for me is just... Because I feel very well-resourced in being able to deal with hardship because I'm always able to recontextualize and reframe. I think part of that is doing so much intuition justification, which is what we talked about, is walking through things, being like, "Why is this? Why does that happen, la, la, la?" When something bad happens, it's understanding why it happened and then understanding the paths that it can take forward and the different attitudes that you can bring to it that can help you come out of it. **Lenny Rachitsky** (01:15:59): That's beautiful. Okay, final question. I know that you recently remodeled your home. It's quite stunning. You share photos of it online. You worked with this amazing architect to help make it as amazing as it is. As a designer, here's the question, how do you find the balance between trusting someone, their own perspective and design approach, versus pushing into a direction you think that it should go? How do you find a balance as a designer? **Jessica Hische** (01:16:28): Well, I actually feel like it's quite easy for me to trust people to do their own thing, because as long as I go to them as being like, "I appreciate you and your vision and that's why I'm paying you," then the last thing that I want to do is micromanage them, because the reason why I'm paying them is because I don't have the bandwidth to do that myself. Because honestly, I'm one of those people that if I had nothing going on, if my job totally blew up or whatever, I would probably be one of those people that just specialize in a different thing every six months and would be like, "I'm going to build a house now from the ground up. I'm going to do this from now, whatever." I just feel very capable of doing anything that I want to do because I understand that I can find the resources for it. **Jessica Hische** (01:17:16): When I hire people to help me do a thing, it's because there is this implicit trust in what they do and that that's why I want to work with them. With the house, I definitely had opinions about stuff. But in general, I'm just like, "Hey, this is your thing. You're the expert. What do you think? Let me give you the parameters and the things that we have to think about. Because you know more about wood resources, and you know more about the cabinet spacing, and whatever, you tell me what you think is going to work best based on all these things that I laid out for you." I found it to be quite easy. I only got really wigged out about a couple of different fine tune-y stuff. **Lenny Rachitsky** (01:18:01): I imagine architects and designers are like, "Oh no, it's going to be a designer I'm working with. They have opinions." I'm glad it wasn't that bad. **Jessica Hische** (01:18:09): I feel like my strength with the work that I do in general is just being incredibly decisive and understanding that there's 10 good answers to every one question. Some people are real maximalists about decision-making and need to look at every gray sofa that exists before they can choose the one gray sofa. Whereas I feel like I can look at 10 gray sofas and go, it feels like there's two or three categories of sofa here, and then within those categories, there's a couple of good options. Here's a brand that I recognize is known for being of high quality. That one's good enough. I can get to it really quickly, and I feel like not everybody can do that. And I think that that permeates through everything that I do in my life. It definitely is a huge part of the logo work, because you really can do anything when it comes to typography. **Jessica Hische** (01:18:57): It can go in 50 million directions. It's just about having someone tell you, "Yes, we could take this anywhere, but these are the valid paths. If we go down this path, this is the most intuitive and most correct way to do it that is closest and most accessible to us. We can noodle on it until kingdom come, but do we have to? This is good." I don't know. I feel like there's some weird knowledge around understanding that nothing is ever 100% perfect, and the most you can aspire and get to is 99.8 or whatever. That last 0.2%, you could spend your whole life trying to do that, or you could move on and do other things and understand that it's nearly perfect. **Lenny Rachitsky** (01:19:49): That is really good advice and a freeing piece of advice. Jessica, it's been an honor to work with you on this logo. I am really excited for people to see it, for it to be the new look of everything I'm doing. Two final questions. Where can folks find you online if they want to learn more and potentially work with you, and how can listeners be useful to you? **Jessica Hische** (01:20:07): Oh, yeah. Of course. I have a website that I occasionally update. It is jessicahische.is/awesome. You'll notice I have a bunch of weird URLs on my website. That's a place to find me. Otherwise, I am on Instagram and Threads a lot. I was formerly a very active Twitter person, and now I'm not really there so much and I bop around with the Twitter clones, but I'm on Threads quite a bit. Instagram and Threads are good for social. Email, I'm easy, hello@jessicaHische.com. What your readers could do for me, I think it's the work that I do in terms of the logo refresh stuff. I feel like this audience is just totally my perfect audience for it because you guys are all a bunch of smart, awesome founders that want beautiful logos, but understand that sometimes you just got to get that first viable option out the door. Once you're ready, you come to me and I help you and it's great. **Lenny Rachitsky** (01:21:12): A match made in heaven. Jessica, thank you so much for being here. **Jessica Hische** (01:21:17): Happy to be here. Great convo. **Lenny Rachitsky** (01:21:19): So good. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [6/17] Meta’s Head of Product (and 29th employee) on working with Mark Zuckerberg, early growth tactics, why PMs are like conductors, and more | Naomi Gleit **Naomi Gleit** (00:00:00): I really believe in frameworks for things that helps drive extreme clarity. I work on a lot of different projects. A lot of times I'm ramping up a new project, I'm like, "Where can I learn what I need to learn about this project?" I ask five different people, get five different answers. That is unacceptable. Of course, I'm sure there's hundreds of docs associated with the project, but there needs to be one canonical doc. Everyone should know exactly where the canonical doc is. That's the one place I can go to get all the information I need about a project and it will link to all the other docs, things on the canonical doc are. **Lenny Rachitsky** (00:00:33): Today my guest is Naomi Gleit. Naomi is head of product at Meta. Other than Mark Zuckerberg, she's the longest-serving executive at Meta. She joined what was then called Facebook as employee number 29 and has been at Meta for almost 20 years. She's seen the company scale from 30 employees to the one and a half trillion dollar business that it is today. Naomi does very few podcasts and interviews and so I was really excited to chat with her and have her on this podcast. In our conversation, we dig into the many lessons that she learned from Facebook's early and legendary growth team, her superpower of taking really complex and gnarly problems and projects, simplifying them and delivering results. We also get into leadership lessons she's learned from Zuck, including his recent transformation into possibly the coolest CEO in tech. Also, why PMs are the conductor of product teams, some very tactical tips for running meetings, writing docs, working out, getting better sleep, and even how to get more protein in your diet. **Naomi Gleit** (00:02:00): Thanks so much for having me. As I told you earlier, I refer your podcast all the time and so I can't believe I have the opportunity to actually talk on it. **Lenny Rachitsky** (00:02:08): Wow, I'm so flattered. I never get tired of hearing that. Appreciate you sharing that. I want to share a couple of tidbits about you because it's pretty crazy when you see this list. Okay, so you are Meta's longest serving executive other than Mark Zuckerberg. You're employee number 29 at Facebook. You've been there for over 19 years. Sorry, at Meta, formerly Facebook. **Naomi Gleit** (00:02:35): I do that all the time. That's what happens when you've been at Meta for 19 years is you can't get the name right. **Lenny Rachitsky** (00:02:42): Okay, good. I won't feel bad about that Then and then the last thing is just you've been at the center of some of the most foundational products that Meta and Facebook have worked on, including working on the early growth team and thinking about the early growth strategy. Basically you've been there from employee number 30 to today, a one and a half trillion dollars company, one of the largest companies in the world today. Very few people have ever seen this sort of growth and scale from the inside. **Lenny Rachitsky** (00:03:09): First of all, I guess let me just ask this, do you ever reflect on this and just realize like, "Holy shit, what a journey I've been on. How wild."? **Naomi Gleit** (00:03:16): It is a great question. I would love to say that I reflect on it. The truth is I think I barely have time to reflect right now. I'm thinking about all the things that I need to do on my to-do list, so I'm pretty in it still. Even after 19 years, I am really focused on the work that I need to do. I do honestly have moments where I get to reflect. For example, on this podcast. Sometimes people do ask me and I think especially as I approach the twenty-year milestone, my twenty-year Faceversary, I'm sure that will give ample opportunity for me to look back. **Lenny Rachitsky** (00:03:55): Such a classic product manager answer. I have too much to do- **Naomi Gleit** (00:03:55): Too busy. **Lenny Rachitsky** (00:03:59): I have to think about this. Yeah, I got to hit some goals here. **Naomi Gleit** (00:06:54): Facebook as part of being an academic, researching Facebook, also being a Stanford student using Facebook. I was like, "I really want to work here." Facebook had just moved to Palo Alto. Mark had driven across country I guess, and arrived in Palo. Alto opened up an office at 443 Emerson Avenue or Emerson Street. It was right above the Jing Jing's Chinese restaurant in downtown Palo Alto and I just went to the office sort of cold called the equivalent of just walking into the office and seeing if there were any available jobs. There were not. I think I did that maybe five to 10 more times. **Naomi Gleit** (00:07:31): Eventually, there was an opening to interview for Sean Parker's personal assistant. He was at the time I think the president. I did interview and I did not get the job. A few months later I found out about a marketing role that was available. And one interesting thing I haven't really talked about was I got an offer from Facebook. I also got a competing offer from LinkedIn, and so at that time I made the choice to go to Facebook because I was interested in the social networking aspect of it. Why was I so bullish on this website at the time it was www.thefacebook.com. Why was I so excited about this thing? **Naomi Gleit** (00:08:12): I think it's because I definitely saw that there was product market fit. I saw that students at Stanford were obsessed with it, but it also had a long list of colleges that were really excited and on the waiting list to be accepted onto Facebook, and so there was this product market fit piece and also a huge demand from other audiences, other colleges, but our younger brothers and sisters were also sort of interested about Facebook and it seemed like it had this much broader appeal. So that's what happened. I got the marketing job. Cheryl also talks about when you are on getting a rocket ship, don't ask what seat. That was my foot in the door and here we are 19 years later. **Lenny Rachitsky** (00:09:02): I was just going to say that that's such a good example of what she recommends of if you can get a seat on a rocket ship, don't ask which seat. And I love the Sean Parker piece. I did not know that. That's hilarious. What a different life would've been if you got that job and went down that track. **Lenny Rachitsky** (00:09:18): So a couple of takeaways here for people that are trying to pick where to work, what I love about your story is one is you just had so much. You just had confidence that this business would work and you just knew that you wanted to get on this rocket ship. You saw attraction. So that told you I guess that added to this confidence that this was going to work out. And then you said that you walked into the office kind of cold, not even cold emailing or calling, but cold arriving. Five to 10 times you said? **Naomi Gleit** (00:09:45): Yeah, it was pure just refusing to quit. I think I just walked into the office, I talked to the person at the front desk, "Is there anything that I can do?" They weren't hiring non-technical people. I didn't have a computer science degree. I wasn't technical. I had this bachelor of arts degree and that's why the personal assistant in the marketing role eventually did open and was something that I thought I could be qualified for. **Lenny Rachitsky** (00:10:12): Cool. I think that's such an empowering lesson of if you look at someone like you and they're like, "Oh, she was so early at Facebook, how lucky," clearly wasn't luck. You knew you wanted to work at this company. You put a lot of effort into making it happen no matter the job. I think that's a really good takeaway and lesson. So if there's a company today that you are excited about that you're just like, "This is going to be a massive success," what I'm hearing is just do everything you can to try to land a job there and eventually you'll be in a role you actually want. It doesn't have to start there. **Naomi Gleit** (00:10:41): When I got to Facebook, I knew I wanted to build. As someone who wasn't really technical, I wasn't going to be an engineer or a coder. I wanted to work with the engineers and the coders to build products. I thought product management was the right function for me, and so my dream was always to be a PM and it wasn't luck as to how I ended up becoming a PM. I sort of took the same approach showing up at the office asking if there were any roles. **Naomi Gleit** (00:11:08): By then, we had moved to 156 University and all of the PMs and engineers worked on the second floor, and I was working in marketing, like I mentioned, and I worked on the third floor and all the business functions worked on the third floor, and my goal was to be a PM. I ended up going, sort of the analogy, I went to the second floor most days after work, asked if there were any projects that I could help out with. **Naomi Gleit** (00:11:34): It was very early days. There was always more to do than people to do it. And so eventually I picked up a few projects, helping with program management, giving my product feedback, and by the time that I actually applied formally to be a product manager, I had been doing the job voluntarily, almost informally for a few months. **Naomi Gleit** (00:11:58): And I remember this because I had a seat on the third floor. I picked up all the stuff on my desk, put it in a box, walked down to the second floor once I got the job to become a PM. And when I got to the second floor, I distinctly remember everyone on the second floor standing and clapping. And so it was a big standing ovation. I'll never forget, Boz was there, by the way. I know Boz has been on your podcast, but even Boz was there sort of standing and clapping. And so I guess to the lesson that you were trying to extract from my story, I do think I sort of tried to create the luck by not giving up and just repeatedly cold calling or cold showing up or cold volunteering until I sort of was able to make it happen. **Lenny Rachitsky** (00:12:51): Amazing. Again, very empowering. It's not just like, "Oh, there's these people that just get lucky they land this PM job." It's like you landed at the company. I want to be a product manager, which is interesting. Most people don't grow up in I want to be a product manager. That's like a rare thing people even want, especially that early on. So it's interesting that you already knew that, but you basically did the job. You did the job of PM before you had the job, and by the time you actually asked for it, you've been doing it for a long time and you could show, "Hey, look, I'm actually good at this. I can do this job." Awesome. **Lenny Rachitsky** (00:13:22): By the way, I love the Boz connection. I'm finding that Boz is connected to the most guests of this podcast in so many different ways. **Naomi Gleit** (00:13:29): Really? **Lenny Rachitsky** (00:13:29): Curious. Yeah, like Ami and- **Naomi Gleit** (00:13:32): Oh yeah. **Lenny Rachitsky** (00:13:33): And a few other people. It's just interesting. There's a Boz spiderweb of connections throughout this podcast so far. Okay, so I'm going to fast-forward to today. So your role today is head of product at Meta? **Naomi Gleit** (00:13:46): Yes. **Lenny Rachitsky** (00:13:46): What does that mean? What do you do at Meta today? How would you describe your role? **Naomi Gleit** (00:13:52): There are a few thousand PMs at Meta. They do not all report to me. I would say a few hundred of them report to me on the teams that I directly manage, but I feel responsible for the entire PM community at Meta. There are things that we do centrally, things like PM performance, PM culture PM onboarding and training, and that's the kind of thing that I look out for. **Naomi Gleit** (00:14:16): Obviously I wanted to be a PM. Head of product is my dream job. I am deeply supportive of the PM function, and so I really care and I think PMs are a huge point of leverage in a company for how we can actually get stuff done and help accomplish the company's goals. And so I sort of focus on PM as a really important exponential lever for doing that. **Lenny Rachitsky** (00:14:45): I love that. Okay. I'm going to come back to what you've learned about what makes super successful PMs, what makes you really successful. I want to take a tangent to Zuck. **Naomi Gleit** (00:14:54): Please. Yes. **Lenny Rachitsky** (00:14:56): So you've known Zuck for over 20 years at this point, and I just have to ask a few Zuck questions because people are always curious to learn from what has worked so well for him. The first question is just there's been a pretty profound transformation in Mark over the past few years, both in terms of how he leads and also just in his coolness and vibe factor. What are your thoughts on just this transformation and how he's been able to pull it off? **Naomi Gleit** (00:15:22): So I've always said that there is the biggest gap of anybody I know between what people think of Mark and who Mark really is. And so I think this is the Mark that I've known for the past 20 years and the world is finally getting to see what I've been lucky enough to see. And that gap that we've talked about is really starting to close. **Naomi Gleit** (00:15:46): How did we get here? I always say Mark is a learn it all, not a know-it-all. He is the fastest person at upskilling of anyone I've ever met. He used to do these annual challenges. One year I did them with him, it was learning Chinese, and within a year he was able to basically achieve an eighth grade fluency in Chinese. And that's just one example. Obviously, he's gotten incredibly great at guitar, MMA, a lot of his passions, but he's also gotten a lot better at some of the professional skills. And I think negotiation, public speaking is one of those. I think before in the early days, it just wasn't something that he was very comfortable with. He's talked himself about coming across as a little scripted. I think he was not confident and pretty careful about how he showed up and he's upskilled here. He's just gotten a lot more comfortable, and so people are able to see who he really is. **Lenny Rachitsky** (00:16:44): He was also like, I don't know, 20 something when he started Facebook and now he's running a 80,000 person org. I could see the emotion habits. **Naomi Gleit** (00:16:52): Yes. I think he might've been 19 or 20 when I came. **Lenny Rachitsky** (00:16:56): Oh God, that's insane. So yeah, I could see why someone would change. I was at the Acquired podcast Chase event with him being interviewed, and he's just such a cool dude now. He just has these big shirts with his own letters on it, his own phrases, his chain. What a cool dude. **Naomi Gleit** (00:17:16): His long hair. **Lenny Rachitsky** (00:17:17): His long hair. **Naomi Gleit** (00:17:18): His watch. Yeah, I was at that event too. I thought it was great. I think, yeah, that's the no gap between who Mark is and what the world sees. **Lenny Rachitsky** (00:17:30): I love that. Is there something about Zuck that you know that most people don't know? Something that would surprise us? **Naomi Gleit** (00:17:37): The one thing I would say about Mark is I think people know he's married. He has three daughters. He's a really great dad, he's a really great husband. I would say he's also a really good friend. Maybe that's something that I can sort of speak to from experience. He's just an incredibly thoughtful friend. There was a period in my life, I think it was 10 years ago when I was going through just sort of a really hard time. I had come out of a breakup, but Mark saw that I was having a hard time. He asked me if I wanted to volunteer to teach a class in East Palo Alto after their school day. **Naomi Gleit** (00:18:15): And in retrospect, it's pretty funny, but Mark and I taught a class about how to build a business. So you had the CEO of Meta teaching this class to a bunch of middle school students, and we got really close to them through that process. We made some really important mentorship connections. For years, we met with them. I think we still continue to, even though they've now at this point graduated from college and have real jobs. **Naomi Gleit** (00:18:43): But one of the lessons that we taught during that class that I remember Mark distinctly writing on the whiteboard, or not the whiteboard, there actually was chalk, it was with chalk on a chalkboard with the four life lessons. That was one, and I kept these for myself as well, love yourself. Two, only then can you truly serve others. Three, focus on what you can control. And four, for those things never give up. **Naomi Gleit** (00:19:12): And that was sort of his life lessons, four steps to how to approach life. And we actually made stickers for these four steps that the students could actually put on their composition notebooks as a reminder. And I think obviously that has really helped me over time, but I think that in that you can see some of what I think we all see in Mark, for example, for those things never give up. He has that aspect of him and it makes sense. For me number three is really the hardest, which is focus on what you can control. I think I probably think I can control more things than I actually can. **Lenny Rachitsky** (00:19:53): So do we all. I love that he was sharing that in a class on how to start a business, this life advice. **Naomi Gleit** (00:20:00): Totally. **Lenny Rachitsky** (00:20:02): Oh man, that's amazing. I want to chat a bit about, so at this point is 86,000 employees, something like that. That's what I found online. So he has to run this massive org as this CEO, one person. I know that one way that he does this, he has something called a small group. Is that the term? **Naomi Gleit** (00:20:24): Yes, small group. **Lenny Rachitsky** (00:20:25): Okay, cool. So he's got the small group that he calls it and it's essentially is like core execs and this group meets regularly, and that's kind of how he's able to manage the entire org through this small group. For people that are struggling to run an increasingly larger org, are there any tidbits from how Mark and the small group operate that might be helpful to folks? **Naomi Gleit** (00:20:47): Sure. So I think the first thing is small group is sort of the leadership team. It's the leaders working on the most important projects at the company, sort of independent of reporting structure and stuff. It's like who are the leaders on the big most important projects or functions? They will be represented in small group. **Naomi Gleit** (00:21:08): What makes this group unique? A lot of them are people like me, people that have been there for a very long time. So I think the tenure of small group is really rare. Why I think that's important is you have a lot of people that are motivated by mission rather than climbing the corporate ladder at this point. And so there are a lot of what I call disagreeable givers. **Naomi Gleit** (00:21:34): So just to back up, I don't know if you've heard this framework, but I think I learned this from Adam Grant during an executive learning and development session, and he was saying that if you think of a two-by-two, there's people who are agreeable and disagreeable, and then there's people who are givers and takers. **Naomi Gleit** (00:21:52): And the most dangerous kind of person to have in an organization is an agreeable taker. And what that means is an agreeable person, super nice, everyone likes them, really easy to get along with, but they're a taker and maybe their motivation is more self-interested rather than what's best for the company, which is how I would define a giver. And the most precious person in an organization is the disagreeable giver. Those are the people who are really motivated to do what's best for the company, but they can be a little bit disagreeable in the sense that they may not say what you want to hear. They may push back on things, they may fight for things. And so I think small group is characterized by a lot of disagreeable givers and I think that's really important for an organization. **Naomi Gleit** (00:22:41): One thing I think Mark has done really well in general is just have a culture, including on his leadership team, of people who give him feedback. I think a lot of times as you get more successful or as you have more fame or if you have more wealth, you lose having an accurate feedback loop. And people may not want to be a hundred percent honest with you for various reasons. And Mark has tried to ensure that he himself has an accurate feedback loop, or we as a company have more of an accurate feedback loop by surrounding himself and our leadership team and creating a culture of giving direct and honest feedback. So that's some of the unique properties of small group. **Naomi Gleit** (00:23:25): From a process perspective, we have one weekly sort of strategic meeting. It's more open-ended, there is time for discussion. It's longer and it's sort of more unstructured. We also have one weekly operational meeting, which is highly structured where we go through all of the priority projects. The person who owns each of the projects will actually speak to the weekly updates for that project. And it's very operational and tactical. **Lenny Rachitsky** (00:23:55): Awesome. I just love this name, small group. It's just like a cozy name. It's not like executive staff or ESA after all these terms people always use. And that's just our small group. **Naomi Gleit** (00:24:07): Totally. **Lenny Rachitsky** (00:24:09): And then this framework you described, it sounds a lot like radical candor of challenging directly, but caring deeply. **Naomi Gleit** (00:24:16): Yes. **Lenny Rachitsky** (00:24:16): Where being disagreeable, but being constructive and additive. Is that the term? What was it? Disagreeable, but? **Naomi Gleit** (00:24:23): A giver. **Lenny Rachitsky** (00:24:24): Giver? Yeah. **Naomi Gleit** (00:24:25): Yes. **Lenny Rachitsky** (00:24:26): Okay. That's great. **Naomi Gleit** (00:24:26): Yes. **Lenny Rachitsky** (00:24:28): If there's nothing here, totally cool. But is there something that you changed Mark's mind about? You've talked about he's good at seeing new data and being like, "Oh, okay, I see, I see." Or is there anything that you were successful there that is an interesting story? **Naomi Gleit** (00:24:42): One of the things that we did in the early days on the growth team, because I'm not sure that necessarily when we talk about this sort of legacy or the history or the lore around the growth team, and this may not be a direct answer to the question, but it didn't really necessarily- **Naomi Gleit** (00:25:00): And this may not be a direct answer to the question, but it didn't really necessarily come from Mark. Mark wasn't like, "You guys should create a growth team. Here's how you should operate." And so I think in some ways we established and grew a growth team and Mark got on board or saw the value in it and was a huge proponent of it, but I'm not sure it necessarily originated with him. And indeed, I think sometimes the focus on being so data- driven might've been something that myself, Alex Schultz, Javier Olavon, these are some of the original people that were on the growth team and that my closest coworkers now may have really pushed on and highlighted the value of for Mark. I'm happy to talk about the growth team, which is something I get asked a lot of questions about, if you want. **Lenny Rachitsky** (00:25:53): Yeah, I'd love to. That's exactly where I was about to segue since you brought that up. So the Facebook growth team, it's a legendary team. I think it was probably the first real growth team in tech. The team developed some of the most core growth levers and techniques that companies use today, and so I'm really excited to chat a bit about this and what you learned from that time. One thing I wanted to start with is there's this legendary activation metric that you all had, the goal was to get, I think it was seven friends in 10 days or something like that. Is that a real thing? Is that what you guys actually did? Anything more there for folks that are like, "Oh, we got to come up with something like this"? **Naomi Gleit** (00:26:30): Sure. So yes, seven friends in 10 days was a thing. 10 friends in 14 days was also a thing. They're the same thing, they're just different points on a retention curve. I would say the key insight here is when we started the growth team, I think we were pretty focused on acquisition. We had a notion though of growth accounting, which looks at what's our net growth every day? And that would look at the number of new users that registered minus the number of users that actually went stale. So after a 30-day period, that's how we define it, they no longer logged in. And then plus the number of users that resurrected, which is after 30 days they came back. And what we found was the churn in resurrection lines were actually much larger than the new user line, which implied to us that retention and driving those two lines was actually our biggest lever to drive net growth. **Naomi Gleit** (00:27:22): And so while we were focused on acquisition, a lot of our focus shifted to be around engagement and retention. How do we drive engagement and retention? We look at the variables that correlate most with that outcome. What we found was friending. And so those two magic moments, having seven friends in 10 days or 10 friends in 14 days really just map to when we feel like your likelihood of being a retained user goes up because you've seen the value in Facebook. And it makes sense, Facebook is much more compelling if you have 14 friends. And the other thing around 10 or 14 days is we wanted it to happen quickly, we wanted to have you experience the magic moment soon after you had registered on the site to prevent you from churning and then us having to resurrect you again. **Lenny Rachitsky** (00:28:17): One of the most interesting lessons from this activation metric that people talk about, because right now everyone's like, "Yeah, of course retention is what you need to focus on. That's what product-market fit is." I think right now that's what everyone knows. I love that you guys basically figured that out, was one of the first times of, "Here's how we understand if our product will last and how to grow retention because it matters most." And retention cohort curves I think was one of the innovations y'all thought about early of just like, "Here's how we track retention, people joining at a certain time, how long do they stick around?" **Naomi Gleit** (00:28:48): Totally. And that was Danny Ferrante who really came up with the growth accounting framework, which I guess is quite obvious, but the plus new minus stale plus resurrected. The thing that I feel like may be valuable for PMs and is one of my Naomi-isms is I think what the growth team really pioneered was being data-driven and product-driven, especially in an area that was historically more of a business function. So I think at that time a lot of the growth in new users was expected to come from marketing or comms, whereas the insight that we had is actually the product is the biggest lever to drive growth, and that means we should have a product and engineering team working on optimizing things like the registration flow, the invite flow, the new user onboarding, getting you seven friends in 10 days. **Naomi Gleit** (00:29:43): One of my Naomi-isms is really understand, identify, and execute. That framework came from 2009 where the growth team at the time, it was fledgling and it just started, was focused on only instrumenting data. And Alex often wears a shirt that says, "I guess when you can know." We just didn't have the data that we needed to make informed decisions to know really what were the biggest levers to drive growth. And so in 2009 in January, we basically stopped doing anything on our roadmap except data instrumentation. And that's when we instrumented every step of the registration flow, instrumented every step of the news or onboarding experience. We knew where there was drop off. And so we understood, which allowed us to identify what were the key opportunities to drive growth and maybe, hey, it's increasing friending in the user experience or 20% drop off on registered users at the email confirmation step, how can we address that? These are the opportunities that we identified and then we would execute by building products. **Naomi Gleit** (00:30:50): So having this data-driven product-driven approach to what I think historically was more of a business responsibility at a company was sort of the special sauce of the growth team. We eventually extended that approach. I think that approach started with the growth team, but we extended to other areas. So for example, one of the projects that I took on after growth was social impact. And instead of what I think a normal company might do, which is start a corporate social responsibility wing, we decided, no, we're going to take a data-driven product-driven approach to driving social impact. Instead of having a foundation that's distributing money, we're going to build a product that actually raises money from our community. And many years later we've raised billions of dollars from the community for charity. So that's sort of the approach that I think is unique about the growth team that expanded to other areas and that I think that the company in many ways has taken to most of the problems that we face. **Lenny Rachitsky** (00:31:55): That's such a good point. And I almost took that for granted, but there was such a huge shift that y'all started from moving from marketing being the driver of growth to product and data and experiments and all that stuff. And so I think that's such a good reminder that, fun fact on the social good team, I'm really close friends with the designer that was on my team, his name's Mickey. He was on that team for a while and really enjoyed and yeah, really enjoyed working with you. Fun fact. **Naomi Gleit** (00:32:22): Oh, that's so great. I remember Mickey, what is his last name? **Lenny Rachitsky** (00:32:26): Settler. **Naomi Gleit** (00:32:27): Okay. Yes, I definitely remember this, yes. And social impact is just one thing that I think I'm really proud of. And again, remember social impact used to be a business thing. You would create this corporate social responsibility part of the company that was very separate from the product and engineering team. **Naomi Gleit** (00:32:48): Another thing that we did in the early days was there was a juncture where it was like, "How are we going to translate this site?" And I think we could have taken more of a non-technical traditional approach and had professional translators translate the entire site into the different languages, and instead sort of what the growth team suggested was why don't we build a version of Facebook that allows you to make translations in line? And so the community of people using Facebook at the time who actually knew the product the best could actually insert translations and there was a whole system that we built around how to up-rank the best translations and down-rank, sort of like Wikipedia. And to this day, we have over 100 languages supported. So we're always trying to find these product technology solutions to these sort of traditional problems. **Lenny Rachitsky** (00:33:39): I totally remember that, where it's like you ask your users to help translate the site. **Naomi Gleit** (00:33:43): Yes, yes. **Lenny Rachitsky** (00:33:46): I want to come back real quick to the activation metric because it's something that a lot of people somewhat misuse and think maybe incorrectly about. So to come up with an activation, as you described, you basically figure out what's the regression of if someone does X, retention increases, and so let's focus on getting them there. And a lot of people struggle with coming up with that metric. Do you have any thoughts on just how important it was to have that very specific activation milestone of seven exact friends in exactly 10 days versus the value of just having anything that is a rallying point for everyone to focus on and drive? **Naomi Gleit** (00:34:19): I think the majority of the value is in the latter, is just having extreme clarity around the goal and that allowed everybody to work towards optimizing the same goal. You're right, we did sort of just pick a point on the curve. I think it could have been any of those. And indeed, as part of preparing for this, I was like, "Was it seven friends in 10 days?" I had to go back and I asked a few people that I worked with back in the day and they were like, "Well, I thought it was 10 in 14." I mean, I think it doesn't matter, it's just that we picked one of them and what mattered there was we had the same goal, what mattered was that it was a retention goal or an activation metric. **Naomi Gleit** (00:34:59): And one of the most important things that actually came out of having that goal was building a new user experience. Believe it or not, when we first launched Facebook, I wasn't around then, but in the early days of when it was just a college site, we didn't need a news or onboarding. We didn't need to explain to people that they had to find their friends. They were sort of automagically connected to everyone on the college campus and sort of knew how to use this product, it felt very intuitive. Again, we were college students building a product for other college students. They were sitting next to each other in libraries or at desks and sort of through osmosis understanding how the product worked. **Naomi Gleit** (00:35:38): It was more when we launched the ability for teens to register and then work networks, and then in 2006 open registration where we started getting all kinds of people with any email address, before it was .edu or a microsoft.com email address that was required in order to sign up for Facebook and then anyone with any email just could register including people like my dad and my grandma that we realized, wow, in order to get people to this magic moment, how are we going to do that? What's the most effective way that insight resulted in building a new user experience? I remember it was just like step one, upload your profile picture. That was really important so people could find you and know who you were. Step two, find your friends. That's where a lot of the contact importing and people you may know and, "Here are other people at your school and here are mutual friends." That step in the news or experience ultimately became one of the most important drivers of that activation metric that we talked about. **Lenny Rachitsky** (00:36:40): I love that you shared that, such a recurring theme on this podcast, the power of onboarding, the value of investing in onboarding and the ripple effects of opportunities there. I love that you also were kind of like the first like, "Onboarding, that's a thing, we need onboarding." **Naomi Gleit** (00:36:55): I know. I mean, I remember the day where I was like, "Do we need to explain to people how to use this? Is it not obvious?" And it's like my dad's like, "I don't understand this whatsoever." My dad would go on to become Facebook's biggest power user because I always beta tested everything with him. But that was not obvious to us at the time in 2006 that we had to explain to people how to use Facebook. **Naomi Gleit** (00:37:25): And again, remember that it's fun talking about this because obviously the product has evolved so much, but the principles are relatively the same. It was thefacebook.com, eventually it became facebook.com, but eventually we built a mobile app and then it was mobile first product, and then it was about mobile photos, and then it was about mobile videos. So over time, the technology has really changed, but the core use case that we really need to educate people on, which is how to connect with their friends on Facebook and whatever iteration or product is the same. And so obviously we still have an onboarding today and it's relatively the same principles, like get a profile picture and find your friends. **Lenny Rachitsky** (00:38:12): Along those same lines, just maybe a last question around the growth stuff that you worked on for folks that are thinking of driving growth, working on onboarding maybe specifically just are there any lessons from things that worked super well when you were looking to accelerate growth of the Facebook early on that you think people are maybe sleeping on as lepers and tactics that worked back then that might still be really powerful today? **Naomi Gleit** (00:38:36): Well, definitely the understand, identify, execute. I would just ask yourselves, do you have the data that you need to know what you need to do on growth? And if not, definitely take the time to instrument that data. **Naomi Gleit** (00:38:49): The thing that, I think we were relatively lucky, I talked about why I was bullish on Facebook in 2005 even was because there was product-market fit. And so for us growth, as much credit as we give to the growth team, I'm actually not sure how much credit we deserve and how much incremental growth we drove above and beyond the fact that this was a product that had product-market fit and we benefited in a huge amount from having high demand for the product. **Naomi Gleit** (00:39:23): So at every step, and I talked about the growth team, the projects that we were working on were really at a high level around removing barriers. There were macro barriers, like the first project I worked on was high school students on Facebook, which is an interesting story in and of itself because at that time we almost created a separate website called Facebook High just to keep them separate from the college students. But at that time we were like, "No, this is one graph. This is one community. College students have friends and people they're connected to of all different ages. Why bifurcate the graph?" And obviously we've maintained that principle ever since. **Naomi Gleit** (00:40:04): But it was about removing barriers. So you had to be a college student, then you had to be a high school student, then you had to be in a work network, then you had to have any email address. One of the next projects I worked on was not everyone has access to a smartphone, how can we remove the barrier of having access to a smartphone and building more of a rich Facebook experience for someone that was using a feature phone or a lower-end device? Internet.org, what about removing the barrier of having access to the internet or being able to afford a data plan? And so those are the macro barriers that thematically the growth team has worked on. **Naomi Gleit** (00:40:40): What I would say is maybe applicable is really the micro barriers. All of the work that we did on growth around optimizing the flows were really about removing micro barriers. One of the things that I thought was just so elegant was after we did that 2009 instrumentation of all the flows, the product flows relevant to growth, what we found is 20% of people aren't actually confirming their email. We tried sending them an SMS, so maybe they would confirm the SMS instead. What we found was a lot of people are actually still clicking on notifications that they're getting, but because it wasn't the specific confirmation email, we weren't able to confirm the account. **Naomi Gleit** (00:41:21): And so what we did was allow people to get notifications even as an unconfirmed account, and then if they clicked on any of those notifications, that would count as an account confirmation as well because they proved ownership of the email. It's just removing a micro barrier of having to go find the confirmation email, click it before you can do anything on the site. So I do think we've been relatively lucky in having a lot of high demand That meant that we could focus on just removing micro barriers. And then on the growth team, a lot of the iterations and optimizations were about removing just sort of friction. **Lenny Rachitsky** (00:41:56): I love that framework of micro barriers and macro barriers, just thinking about ways to make this accessible to more people and also just helping them get through the flow faster. I also love your point about how a lot of growth teams get a lot of credit for growing a business when really in many ways it could have done really well even without that team potentially because product-market fit was so strong. I think about this with Airbnb honestly as just such after it gets to a certain point, such good product-market fit that who knows what would've happen if there was no one working on growth? It probably would've been okay for a long time. **Naomi Gleit** (00:42:27): Totally. And then maybe where we do sort of see the impact is maybe something like the translations thing that we talked about. With the macro barrier, removing the language barrier, and so maybe the approach we took meant that we supported 100 plus languages instead of whatever the professional translators, we have the long tail of languages so that last person who's still speaking a near extinct language can still use Facebook. But yeah, I think that's right. I sometimes think that maybe some of our efforts were really more on the margin of a bigger trend around product-market fit. **Lenny Rachitsky** (00:43:06): Final little thing I would just want to highlight again that you said that I think is so important, and I've always thought is true and I love that you confirmed it, is that the activation metric that you all rallied around the biggest value of it wasn't this is exactly the right regression connection to retention, it's more that we have something we are all going to focus on, and that is where most of the impact comes from is let's get more people to that point, whether it's perfectly right or not, it doesn't really matter. **Naomi Gleit** (00:43:32): Yes. **Lenny Rachitsky** (00:43:32): Love that. And I think that's really freeing to a lot of people because they're like, "Oh, we don't know if we're going to be as perfect about this versus let's just drive some growth and get people who are good enough thinking on that." Okay, great. **Lenny Rachitsky** (00:43:45): You mentioned Naomi-isms, I want to segue to that. So let me first read a quote. So I asked Adam Mosseri, who is Head of Instagram, what to ask you. I know you guys work together on a bunch of stuff. Here's how he described you, "Naomi is called the conductor here at Meta. She has an incredible ability to handle the most complex projects and problems and bring the right people together to simplify and solve them. She is very firm yet kind. Her standards are extremely high, and she sets the bar." Also many other people that I messaged said very similar things about you, about how you're incredibly good at taking very complex problems and getting shit done, getting them done, simplifying them and getting them done. **Lenny Rachitsky** (00:44:27): So I want to spend some time understanding what you've learned about how to do this well. What are the skills you've collected that allow you to take really complex problems and get to a solution, stay kind but firm and take on these really hard challenges? So maybe just broadly, I'm curious, what are some of these skills that you have built that allow you to do this? **Naomi Gleit** (00:44:51): Yeah, well also that's very kind of Adam. I adore Adam obviously, he is one of the tenured people in small group and I've actually gotten the opportunity to work even more closely with him than usual. We recently launched something called Teen Accounts and Adam and I worked very closely on that. **Naomi Gleit** (00:45:10): In terms of how I do the things people say that I can do, I really rely on Naomi-isms. Like I said, and actually I refer your podcast out a lot because there isn't just a PM university that I can send people to, there isn't a formal training that people can get to become a product manager, and that's where Naomi-isms came from. It was stuff that I learned on the job from other people, including from Adam, that I found myself repeating over and over again. "A good PM looks for a way to make that more efficient," for me, that was writing them down, people started calling them Naomi-isms. I started sharing them internally. And then I think two years ago, I also started sharing them externally. **Naomi Gleit** (00:45:52): Adam referred to me as a conductor, that's one of the Naomi-isms, in my role as Head of Product, I want to educate the PM community about what is PM? It's the most common question I get from PMs and non-PMs, "What do PMs do? What makes a great PM?" And what I say is a PM is a conductor. It's as though the team that you are a PM on is an orchestra. There are many different functions in your team that includes legal policy, comms, data analytics, engineering, design, much like there are many different instruments in an orchestra. And as a PM, your job is to make sure everyone's playing their part correctly, every section in the orchestra is playing their part, but at the same time, they're playing together, they're unified in the music that they're producing and that they're playing at the right tempo. **Naomi Gleit** (00:46:48): And a lot of times I think people use music analogies or vocabulary to describe the work, and that includes things like people being in harmony, like a good team, a good PM, a good orchestra is in harmony, they're in sync, they're at the right tempo, they have the right cadence. That's sort of how I imagine what a PM does at work. Important characteristics are the PM is not the star of the show. Indeed, conductors don't even say anything during the performance. And also, I would at the same time give PMs little metronomes and conductor wands. This was something that I used to do when we were smaller., Just to sort of take the analogy way too far. **Lenny Rachitsky** (00:47:29): That's so funny. You actually gave him conductor wands and metronomes? **Naomi Gleit** (00:47:32): Oh yeah, just to wave around. Yeah, I love that. **Lenny Rachitsky** (00:47:35): I would love a conductor wand. **Naomi Gleit** (00:48:57): So PM as conductor is sort of how I describe the product management function, but one of the key Naomi-isms that I think is really critical to getting stuff done is what I call extreme clarity. I think our jobs are super hard. Extreme clarity means everyone's on the same page. It definitely doesn't mean that they all agree with each other, but they just have the same understanding of the facts. So we can disagree, but we all believe in the facts, which is that there's A, B, C, our options are X, Y, Z and here are the trade-offs 1, 2, 3. That kind of shared understanding is what extreme clarity is. **Naomi Gleit** (00:49:36): That came from a place of just being in many meetings, on many emails, in many situations where I felt like we actually agree on something, the nature of this conflict is a result of misunderstanding. And that seems like an incredible waste of time. And so we want to have extreme clarity so we can just focus our conversations on things when we actually agree, not when we are misunderstanding each other. There are a lot of tactics that I use to drive extreme clarity. **Lenny Rachitsky** (00:50:03): Yeah, I was going to ask how you do that, that sounds great. **Naomi Gleit** (00:50:00): ... Tactics that I use to drive extreme clarity. **Lenny Rachitsky** (00:50:03): Yeah, I was going to ask how do you do that. That sounds great. How does one get to extreme clarity? **Naomi Gleit** (00:50:07): So another name I'm using is canonical everything, so that includes canonical nomenclature, I often talk about canonical nomenclature. One way to ensure extreme clarity is we have the shared vocabulary. I've been in a lot of situations where people are using the same or different words to describe the same or different things, which results in talking past each other. One of the most egregious examples of this is when I was working, I was in a conversation around how our reviewers and global operations were performing, and we were using consistency and accuracy interchangeably. Consistency refers to how often different reviewers agree on the decision. Accuracy refers to how often the decision is correct according to ground truth. Those are very different things. We don't want to optimize for consistency because you could be consistently wrong. We want to optimize for accuracy. **Naomi Gleit** (00:50:56): And so that is what canonical nomenclature is literally writing out all the words in their definitions, so when we communicate, we are using the same vocabulary. I really believe in visuals. I think sometimes just having a conversation or a big meeting where people are talking, I'm just not very auditory, I'm a very visual person, it's hard for me to follow along just by listening. I will often have a visual in a meeting. I will leverage that visual to literally real time edit what is being decided. For example, if we have multiple options, I will edit the slide that's being projected to say, "We decided on option one, here are the next steps, 1, 2, 3." A lot of times people are saying, "That's not what I heard. I heard this as a next step, or I heard that as a next step." I love that because that avoids leaving the meeting and being like, "I don't know what we agreed to. I heard this, you heard that." No, actually we haven't agreed upon set of decisions and next steps that we all real time edited and looked at together. **Lenny Rachitsky** (00:51:54): Just to double click on that one real quick, so what you're describing for the visual is you're presenting here's our options, here's our three options on a slide. You all decide we're going to go with option two, you edit the slide with a star, here's what we chose, and then maybe change some stuff. And this is exactly to your point of extreme clarity, people can see clearly this is what we're choosing. If they disagree and don't realize that's what's happening, it'll be really clear. **Naomi Gleit** (00:52:17): Totally. **Lenny Rachitsky** (00:52:18): Awesome. **Naomi Gleit** (00:52:19): And one thing people make fun of me a lot for that I think is just a great example of extreme clarity is I never use bulleted lists because you can never refer to a bullet. I always use numbered lists because you can always in the visual in a meeting as referenced in number two, I have feedback on that, versus the third bullet, two up from the second, whatever, that is not extreme clarity. So it's very, very small tactical things to bigger things like canonical everything. But I can be a little bit strict. **Lenny Rachitsky** (00:52:54): I love that very tactical tip and that is awesome, that's exactly the stuff I look for. Is there any other very nuanced tip along those lines that is helpful in extreme clarity or canonical everything? **Naomi Gleit** (00:53:09): Canonical everything... And stop me if I'm getting too wonky, I can really get into this. **Lenny Rachitsky** (00:53:16): We got a ways to go. **Naomi Gleit** (00:53:18): When I had a face bursary, along the years people have given me posters and the posters say these Naomi-ism, so extreme clarity is one, canonical everything is another. I think people really associate me with canonical, canonical, canonical. I always want a canonical doc. This came from a place of me I work on a lot of different projects, a lot of times I'm ramping up mid-project, I'm like, "Where can I learn what I need to learn about this project?" I ask five different people, get five different answers, that is unacceptable. Everyone should know exactly where the canonical doc is. That's the one place I can go to get all the information I need about a project and it will link to all the other docs. Of course, I'm sure there's hundreds of docs associated with the project, but there needs to be one canonical doc, and that canonical doc really has to have the basic information that you need to know. **Naomi Gleit** (00:54:05): For any project, the basic information that you need to know is what are the discrete areas of work, I call those work streams, this is pretty obvious. Who are the owners on those work streams? So for every work stream there's an owner. Again, it seems pretty obvious. Sometimes I'm like, "Who's owning this?" And it's like people don't know. That's why I think it's very important to have a single-threaded owner. We used to call this a directly responsible individual or a throat to choke. We obviously don't say that anymore. Single-threaded owner, every work stream has a single-threaded owner. Sometimes work streams are really big. You have sub work streams underneath them. Everything canonical needs to recurse, so you should have an owner or an STO for the sub work stream. The other things on the canonical doc are what is the process by which the people on this team work together. **Naomi Gleit** (00:54:54): I hate pairwise conversations. I feel like they're a waste of time. I feel like you could have four conversations with four different people or one conversation with all four people. Everyone has the same context. Ideally there's a visual in that meeting and you real time edited it, there is extreme clarity. The canonical doc will have what is the canonical meetings that people have, what is the canonical email list that you're going to use, what is the canonical workplace chat. Let's not reinvent the same audience 10 different times with different permutations of the people on the working team. Let's just have one canonical chat. And then often the canonical doc will have the canonical nomenclature. I really believe in frameworks for things that helps drive extreme clarity. A framework is best understood when there's a visual representation of the framework in my mind, and so we'll have canonical visuals and that's what I mean by canonical everything. So anytime I start on a new project, everyone knows to send me the canonical doc. **Lenny Rachitsky** (00:55:52): I love this. If you come into a that you've given that's really gnarly and complex, what do you find are the first couple things you do that make a big dent on helping everyone align and understand what happens, what they should be doing and what they should be prioritizing? **Naomi Gleit** (00:56:12): A lot of times I'm simplifying. A lot of times there isn't a canonical doc and so I'll go through the process of creating that, but I think that really falls under the simplification thing. I often go into a project, everyone's operating at a PhD level, I'm coming in at a kindergarten level, and so I need to understand... It's almost like all of this complexity we're at a PhD level, I need to create the curriculum, go back to basic building blocks for the kindergarten level, how do I explain that and understand this project at a kindergarten level. It doesn't mean I want to oversimplify, that's not what a simplifier does. They're not oversimplifying, but what they are doing is identifying the most basic building blocks of a complex problem and then unfolding, or revealing or building on top of them additional complexity and details as you go along. **Naomi Gleit** (00:57:06): And so sometimes I talk about a school pyramid, but I need to establish the kindergarten curriculum and then the elementary school curriculum and then the high school curriculum and then the college curriculum, and then we can operate at the PhD level. But oftentimes people on the project are at really different levels of understanding or complexity. And until we have what we call the school pyramid, the curriculums for every level of the project, it's really hard to make progress. A lot of times that process of simplification will often identify what are the most important things to deal with on the project. **Lenny Rachitsky** (00:57:48): And so what I'm hearing is when you come into a project and the way you simplify is you start putting together a doc that describes these things you're talking about, here's the work streams, here's the owners, here's the process, here's our canonical meeting style, and that reveals here's what matters most and where there's confusion. **Naomi Gleit** (00:58:07): Yes, yes. Yeah, that is. And a lot of times what needs to happen in the project is sometimes there's a strategy or an execution issue and sometimes there's a people or a process issue. I would say 80% of the time I think it's a people or process issue. And that refers to not having the right people on the project, or having the right people but not having the right process by which they work together, a strategy or execution issue. When we get to that, I first try to tackle those or in general I think it's really important to have perfect execution. I want to make sure a project is perfectly executing, because only then can we really reevaluate whether or not this strategy is right or wrong. We're in the worst of all worlds where we are imperfectly executing and therefore, at the end of the day, the project might fail, but we don't know why. **Naomi Gleit** (00:59:02): Is it because the strategy was right or wrong or is it because the execution was poor? The ideal case is the strategy was right and you perfectly executed on it. The next best case scenario is the strategy was wrong, but you perfectly executed on it, because then you learned the strategy was wrong. Revamp the strategy and try again. **Lenny Rachitsky** (00:59:22): You're really in the PM part of my brain. I feel like most PMs listening are like it has clean documents, really simple processes, there's one person to charge, it links to everything. It just feels good. **Naomi Gleit** (00:59:34): Totally. And, again, sometimes I feel the need to defend that the process is not for process' sake, it's ultimately to help us all move faster and work better. So hopefully that comes through. But I deeply believe that it is through this approach that we can move faster. And you have to prove that nobody wants more process and more meetings and more, but my goal is that with this we're actually simplifying process and getting less meetings and just making things clearer and ultimately moving faster. **Lenny Rachitsky** (01:00:08): I'm going to read another quote from another one of your co-workers, Charles Porch, he's vice president of global partnerships at Instagram and he basically said what we've been talking about, some of the biggest strategic bets and biggest swings Meta has made have had Naomi at the helm. No one can hurt cats, drive clarity, and get to outcomes more seamlessly than she can. She's legendary within Meta for her canonical documents. **Naomi Gleit** (01:00:33): Great. **Lenny Rachitsky** (01:00:34): Maybe just following this thread a little bit further, what's the gnarliest project that you've worked on that would be a good example of you coming in and helping simplify and get it over the finish line? **Naomi Gleit** (01:00:47): Well, Charles may be thinking of the most recent project that we worked on. I don't know if it's necessarily the gnarliest, but it's definitely one of the most cross-functional projects that I've worked on before. Basically every team at the company in some way works on youth. And last week we actually launched teen accounts, which was a very complex project. Again, it involved the Instagram team, the central youth team, the different teams working on various aspects of this, every function, legal policy, comms, marketing product. And I think we definitely leveraged a lot of these Naomi-isms. And just to give you a sense of what teen accounts is, it was basically putting all teens into the safest settings by default on Instagram. And the reason I'm working on this, I work across multiple teams at Facebook, so obviously Adam is the head of Instagram and I work closely with him on this, like I was referring to yesterday. **Naomi Gleit** (01:02:02): But this is something, these teen accounts, is something that we are thinking about how we expand to the other apps that we have, including Facebook and WhatsApp and Threads. And I tend to work on projects that are across our family of apps and future platforms, and that's why I was involved in this. But basically what teen accounts does is put teens in these safest settings. It's super focused on trying to address parents' biggest concerns around their teens on social media. This has obviously been a really big topic. We've had a lot of these features and tools. What this launch did is simplify things, standardize things, and add a lot more functionality that gives parents control. **Naomi Gleit** (01:02:42): I think the thing you really need to know is that for under 16-year-olds, if they want to change any of these defaults, they're going to have to get their parents' permission. And so it's interesting that we're really going to create an incentive for teens to get their parents involved and to actually set up parental supervision, especially because one of the default settings is a private account. So there's tens of millions of teens that currently have public accounts today that we are going to automatically transition to private accounts unless they get their parents' permission to stay public. And so it's a relatively big shift, fundamental change for how Instagram works for teens, and I would say one of the more complicated projects that I've worked. **Lenny Rachitsky** (01:03:28): Yeah, and it just launched, right? **Naomi Gleit** (01:03:30): Yes. **Lenny Rachitsky** (01:03:31): As a new father, I'm excited for you all to be working on these sorts of things. I don't need it yet, but I'm glad it's going to be there. And it's funny how Meta and Facebook is in this world where people complain about teens using social media and then you work on making the product better for teens and kids using social media, and then it's like, "Facebook's getting teens on social media." There's no way to make it feel good to people. No matter what you do, people are going to complain. That's what- **Naomi Gleit** (01:04:00): Totally. And I think the goal of this launch was to orient ourselves and really there's a lot of complaints, there's a lot of different voices. I think we just are focused on parents. We think parents know best. Every kid is different and parents know their own kid the best. So that has been our north star in terms of the approach here. When I talk about teen accounts, as product people I think one thing that you would appreciate is the thing that I think is really important when it comes to teens on the internet is really having an understanding of how old someone is when they're using our apps. And it's important that we know how old they are because then we can put them in an age-appropriate experience. So now we have teen accounts, we want to put all teens into teen accounts. **Naomi Gleit** (01:04:49): We all know sometimes teens lie. That's been the biggest feedback that we've been getting is teens are really smart, they're going to find workarounds, they're going to be creative, they're going to lie about their age. And as a product person, the way that I think this should really work is that instead of everyone entering... Teens use, on average, 40 apps, instead of Instagram and the other 39 apps that teens use trying to verify the age of the person using their app is for two companies to do this, which is Apple and Google, they do collect the age, they should make that available to developers. And we ask for information from the device all the time with user consent, can Instagram have access to your camera, can Instagram have access to your location information? Apps should be able to ask, can Instagram have access to your birthday? And that would, I think, elegantly from a product perspective, from a simplification perspective, from a privacy preserving perspective and what's easiest for parents, that would be the right product solution to solve this problem around age that we're all trying to grapple with right now. **Naomi Gleit** (01:05:56): And there's a lot of stuff that we're doing. Part of the reason that this project was so complicated, and I mentioned the age team, is we're building classifiers to try to predict how old people are based on not just the age that they've stated, but based on who they're talking to, what kind of content they're looking at, what the age of the people they're connected to is, do we think that this is actually an adult like they say, or is it really a teen. And so we're doing a lot to try to predict age or prevent people from lying about their age, but I think this would be a really big win for the industry. **Lenny Rachitsky** (01:06:31): Makes sense to me. **Naomi Gleit** (01:06:33): Okay. Thank you, Lenny. **Lenny Rachitsky** (01:06:38): So to close out this portion in this chapter of our conversation on Naomi-isms, I know something else that you're really good at that I've heard from a few people is running meetings, something that a lot of people always want to get better at. Any tips? What have you learned about running a great meeting? **Naomi Gleit** (01:06:54): A meeting is a high value and it's high cost amount of time, and then I want to make sure it's as productive as possible. What I will do is send an agenda 24 hours prior to the meeting. That agenda will include a pre-read. I've talked to people who if the pre-read is not attached to the calendar invite or associated with a meeting at least 24 hours in advance, they will cancel the meeting. That just goes to show we want everybody in the meeting to have full context, have read the pre-read. Often what will happen in the previous 24 hours is because we're all sending pre-reads on Google Slides, there will be a lot of conversation and questions that get hashed out leading up to the meeting. During the meeting, like I said, I think it's really important for a group of people to be looking at something and anchoring people on something. **Naomi Gleit** (01:07:48): If somebody joins the meeting, say, five minutes late, they should know exactly where in the agenda you are in the meeting and what is being discussed based on catching up from the visual that's being projected. Usually a meeting can be and hopefully a meeting is really either is a decision meeting. So if there is a decision, I need three options and I need a recommendation that should hopefully help focus the meeting. And then, like I said, I will real-time edit the visual such that we document and have extreme clarity on what is the option that we agreed on and any next steps that we also agreed to. **Naomi Gleit** (01:08:28): After the meeting, anyone who wasn't in the meeting, that's fine because within 24 hours post-meeting I will send the notes, reply all to the meeting invite and send the notes. So just tactically, I use the calendar invite as the canonical unit by which to handle all of this communication because a lot of times meetings are one-offs, there isn't an existing email or chat thread that maps perfectly to the audience of the meeting, so for me that is the meeting or the calendar invite. So I'll click on the calendar invite, reply all, include the pre-read, pre-meeting, and then do this reply all again post-meeting 24 hours with the notes and the decisions and the next steps. **Lenny Rachitsky** (01:09:11): I love this. So many very specific tactics here. I love it. This is food for my brain. I love the always have three options and a recommendation, that's such a simple thing to recommend, but such a powerful way of operating as a PM, just like, "Here are the options, here's what I recommend, here's why." **Naomi Gleit** (01:09:29): Oh, one thing I forgot that I learned from Guy Rosen, he is our chief security officer, is when you have three options and a recommendation, in terms of evaluating the options, I don't love pros and cons. It's a flat list of text. It's hard to just get the big picture from that. Oftentimes we'll use a traffic light. That means that the three options are three rows. The columns in the table will be criteria by which to evaluate the options. Those could either be functions. So for example, if I have three options as the rows, column one could be the legal perspective, column two could be the policy perspective, column three could be the privacy or product perspective. Alternatively, the columns could map to different criteria like what we're optimizing for. So it could be the user experience, it could be the engineering feasibility, it could be the internal complexity, whatever are the criteria should be laid out in the columns. **Naomi Gleit** (01:10:31): And then obviously it should be color-coded, red, yellow, green based on how it stacks up against those criteria. And what this allows is to get back to the point of the visual is you can quickly look at the three options, see where's the most red, and rule that out. Ideally, the recommendation has some combination of the more green or yellow than the other options. And then obviously within these cells you can spell out the specific rationale for the coloring. But I think this is a really good way to run a meeting and just create extreme clarity around how you're evaluating the options in a way that a flat list of pros and cons just doesn't. **Lenny Rachitsky** (01:11:12): What other podcasts would have this level of detail of how to run a discussion on a decision? And this is exactly what people want to hear, so I love it. So product market fit for listeners of this podcast. I love it. I love it. And obviously the reason this is more effective is it's not just like, "Here's a quick sentence on the pro and con." It's like, "Here's what I actually think this is good or bad for the things that matter to the business." **Naomi Gleit** (01:11:39): That's exactly right. **Lenny Rachitsky** (01:11:40): So that makes tons of sense. **Naomi Gleit** (01:11:41): It also gives people a framework to plug into. A lot of times the creation of a pre-read for these discussions involves many different people from many different teams and functions. If you have a traffic light, they can own filling out their cell, they can own the rationale behind the legal position on option one, two, and three. And, in general, I'm super into frameworks that allow people to plug into and clearly represent their point of view. **Lenny Rachitsky** (01:12:08): I love it. Final question, completely different topic. I saw a Wall Street Journal story about how you exercise and your exercise regimen, and how important that is to your life and career. Now, most people don't have a Wall Street Journal story about their exercise regimen, especially a tech worker. And I know this is just important to your work, and they wrote that this basically helps you become better at your job. Any advice there for folks that want to lean into exercise, exercise more for how to actually do that? Because your advice is this actually makes you better at work and life. **Naomi Gleit** (01:12:44): People are always like, "What are you training for?" And I'm like, "I'm training for life." I have four musties, it is eat, sleep a long time, and exercise. Those are the things that I need in order to perform. And the other areas of my life seems pretty obvious, but until recently I actually did not prioritize sleep. My boyfriend is actually super into sleep and we have the Eight Sleep, we have eye masks, we have blackout shades, we have good sleep hygiene, and so I'm getting much better at that. But exercise is something that I've always been on top of. Alone time is also a musty for me because I'm an introvert, I need that time to recharge, otherwise I think I get weird around people. **Naomi Gleit** (01:13:28): In terms of how I prioritize it, it's a non-negotiable or table stakes, every morning I have to work out. I am also lucky enough to work in an environment where I can wear workout clothes to work, which I often do. I think working out is sure the hour of the day that I'm doing my exercise, but I also view, like I said, life is a workout, performing at work is a workout. I need to be able to move. I need to feel comfortable. It's very physical, I think, especially if you're trying really hard to be a conductor, and I'm running around with a metaphorical conductor wand, I need to be able to move. A while ago, and that's what the Wall Street Journal article was about, I set a goal of doing five pull-ups. I'd read somewhere in an article that less than 1% of women can actually do. I think having a goal is really helpful. **Naomi Gleit** (01:14:22): That's something that I worked on, and anyone can do this truly if you train for it. I think it's potentially more technique for me than strength per se, and I worked up towards that goal. I think exercise, in addition to all of the physical benefits, primarily has a mental health benefit I think for me. And also there are just a lot of lessons that I think I take from exercise. For example, I think being able to do five pull-ups taught me I can do hard things in this really narrow, measurable way, which gave me confidence in other aspects of my life. **Lenny Rachitsky** (01:15:01): I had a friend who her goal was... **Naomi Gleit** (01:15:00): Another aspect of my life. **Lenny Rachitsky** (01:15:02): I had a friend who her goal was do one push-up. **Naomi Gleit** (01:15:06): One push-up. **Lenny Rachitsky** (01:15:06): She's like, "I want to be able to do one push-up" and that was really motivating to her. And then she finally got there and then she could do more. **Naomi Gleit** (01:15:12): That's awesome. **Lenny Rachitsky** (01:15:13): Yeah, similar. I have so many notes here as that you were talking. The other is sleep advice. So eye mask. I have an awesome eye mask that I'll recommend in the show notes. It's funny. **Naomi Gleit** (01:15:23): Please. **Lenny Rachitsky** (01:15:24): What is that? Of all the things I've recommended in all the various places I get the most comments about, "Thank you for this very specific eye mask. It changed my life." It's like WAOAW, it's one Tim Ferriss has often recommended. **Naomi Gleit** (01:15:36): Okay. **Lenny Rachitsky** (01:15:37): W-A-O... I'll link to it in the show notes, but it's- **Naomi Gleit** (01:15:39): Oh, great. **Lenny Rachitsky** (01:15:41): WAOAW, let me look it up real quick 'cause people are going to be like, "Oh, I got to get it." WAOAW eye mask. **Naomi Gleit** (01:15:46): The one that we have has cushions around the eyes such that it's not flush against your eyes. **Lenny Rachitsky** (01:15:54): Yeah, this is the same. Okay. **Naomi Gleit** (01:15:55): Oh great. **Lenny Rachitsky** (01:15:58): W-A-O-A-W sleep mask on Amazon. It's 13 bucks and amazing. My wife and I both sleep with these eye masks. It's ridiculous until you're like, "I can't sleep without one now." **Naomi Gleit** (01:16:10): Totally. Well there's a lot of research that even ambient lighting results in lower quality sleep. So I think that's why the blackout shades and the eye mask just help ensure it's truly dark. **Lenny Rachitsky** (01:16:20): Yeah, I was just watching a podcast and the advice there is even your smoke alarm with a little light is too much light. You need to cover that up to create real darkness and why not just wear an eye mask? You don't have to worry about any of that. **Naomi Gleit** (01:16:35): Totally. **Lenny Rachitsky** (01:16:36): Okay, and then one thing I didn't mention when you're talking about the conductor, the PM as a conductor, that's exactly the metaphor I've always used my entire career when people ask me about what is product manager? So we're alike. **Naomi Gleit** (01:16:46): Really? **Lenny Rachitsky** (01:16:47): Yeah, I have all these slides of here's the PM and it's like a symphony and the conductor standing there. **Naomi Gleit** (01:16:52): Lenny, do you know how happy that makes me? Because I feel like sometimes people are like, "That sounds crazy," but the fact that you actually came to that same conclusion makes me... Why did you come to that conclusion? I'm just curious **Lenny Rachitsky** (01:17:09): Because as you said, the PM's not making the thing. They're just helping each of the people who are the most talented at their very specific skill do the best possible work and their back is to the audience. They're trying to stay out of the way even though they come in, everyone claps for them, the outstanding event, and then in theory they could step in a little bit to help out when they can pinch it on design here and there and research here and there, probably not engineering. So those are the reasons and they're not in charge. The chair wind violinist is the actual person that's making the music and the best at this thing. **Naomi Gleit** (01:17:48): It's so great to hear somebody else talk about this too. Thank you. And I think that that is really how I view my role and what I do and I think maybe just hearing you talk about it reminded me why I think I put so much emphasis on just elevating the people on my team and the people around me and candidly, one of the development areas for me, and it could be downstream because I do have this analogy of how to be a PM, is that the growth feedback or the constructive feedback for me is really learning when to lead from the front more. Maybe when to be less of a quiet conductor that's really elevating the first chair violinist and be more front facing. **Naomi Gleit** (01:18:39): I think a lot of my approach and my leadership style is really leading through the people on my team and helping grow them. And a lot of times I think that they're dedicated, they're experts, they know particular areas. Obviously as a head of product, I manage a portfolio of different projects of which each of them has the incredible leader on it. And so oftentimes I'm just really trying to lead from behind and help them be as successful as possible. But there is a time and a place when maybe that silent conductor needs to take more of a vocal and front facing role. **Lenny Rachitsky** (01:19:16): I know exactly what you mean. I had the same problem when I was a PM because there's always this fear that PMs in charge and telling everyone to do. And so I had the opposite of like, "Okay, and that's not me. I'm going to just let you do the things you think are best and I'll just make sure the best ideas come to the surface," and I have to learn exactly the same thing. Sometimes people just want you to point them in the right direction and make the decision in the end. And the best PMs are people that have the best opinions about what is going to work, how intuition of what users need, have strong product sense and all that stuff. I've had this post that I'm trying to work on along these lines where there's this reaction to PMs aren't the CEO of the product. **Lenny Rachitsky** (01:19:56): They're just like... No, don't call yourselves that. I think it's the opposite. I think PMs actually should think of themselves as the CEO of the product, not in terms of they are in charge and can fire people and manage people, but they're the closest heuristic for what the CEO and the founder wants. They think of what does the business need, what is going to help the customers, what's going to help us grow? And I think the PM is the closest to that role and so I think it's important to think of that role as that even though you're not technically in charge. **Naomi Gleit** (01:20:25): And maybe you could call it something different, but I totally agree with that sentiment. I think we were trying to push against the criticism that PMs were bossing everybody around, but actually I think you- **Lenny Rachitsky** (01:20:42): There's baggage there. **Naomi Gleit** (01:20:43): There's baggage there. I call it, there's something called the great non-technical. There was a period of time at Facebook where I think the PMs really had to prove their value to the engineers and show that we were not slowing things down with all this extra process. You can imagine an engineer hearing me talk about how to run a meeting and all the canonical docs and just be like, "What? This sounds terrible." So yeah, we had to prove that, but I actually do think the PM is the closest to really channeling what the CEO or the founder wants. Another thing that I've worked on and that I'm working on is really developing a much stronger first-party perspective. It's not enough for the PM to run this people in process that we talked about. Obviously I love that stuff. I lean that way, but at the end of the day, a PM cannot outsource their perspective or delegate their thinking through people and process. **Naomi Gleit** (01:21:46): And so for me that has been a learning curve and I am trying to, as someone who's very consensus driven, I want to hear all the different opinions from all the different people. I can still do that. I can still through people in process talk to all the different folks working on a project, hear their first party perspectives and then use all of that to synthesize my own because it will be unique given my role on the team and just what I'm trying to optimize for and really make sure that I both develop that first-party opinion and communicate it clearly. And like you said, the best PMs I think can do it all. **Lenny Rachitsky** (01:22:27): Just to follow this thread, one thread further, because this is something I think a lot of product managers work on and are told to work on, is there anything you've found to be helpful in building this skill in yourself that might be helpful to folks that are working on it? **Naomi Gleit** (01:22:39): I'm lucky enough because I have a big team. I have someone who helps me schedule my time and I used to goal that person and goal our work together on just being as efficient as possible. But now what I am goaling that person and what we're trying to accomplish here is giving me as much time to develop a first-party point of view. And so what is the most effective way to do that? And for me it is having two to three hour blocks of time where I can actually sit, think, have space, but maybe something that's different about me than other people is its very, very helpful for me to talk to maybe one or two people, not be in a big meeting with 40 people, trusted people. **Naomi Gleit** (01:23:28): I have an incredible person on my team that I talk to that I think really helps me clarify my thinking. And so to go back to the beginning, just I'm trying to find blocks in my day that I can spend time thinking and also within those blocks, they don't have to be alone time. They can also be scheduling my chief of staff and my head of data to bounce ideas off of as a sounding board because that is the process that I know best for me in terms of really developing a first party perspective. **Lenny Rachitsky** (01:23:59): Such a good tip. It makes sense if you're just spending all your day coordinating in meetings, checking things, reviewing things, you have no time to actually think about what you think is the right move and answer and strategy and next step. And so that's a really good tip. If you're finding that you don't have time to think about what you think is the right solution and the right strategy and the right product decision, fine, just block time to think about this stuff. I have these deep work slots in my calendar. I've written about this a few times where it's three hours and the invite, I don't know if you can do this these days, but it was just, if you book time during the slot, I will slap you. Nobody did. **Naomi Gleit** (01:24:42): That's amazing. And I think for me, some people might need three hours on their own. I think for me, and I don't know about you, talking things through with one or two people really helps me as well. So sometimes it was almost quite challenging for me to think of going into a room by myself for three hours and then I was just going to figure it out on my own. This is like, and I don't know how people help people think strategically the best, but it doesn't have to necessarily be alone. **Lenny Rachitsky** (01:25:16): That's a great tip. Just have a sparring partner. **Naomi Gleit** (01:25:17): Yes. **Lenny Rachitsky** (01:25:17): Someone who is just interested in exploring ideas and not just have a clear agenda. I love that. Okay, Naomi, I love this tangent we went on as we were wrapping up. **Naomi Gleit** (01:25:29): I know, totally. **Lenny Rachitsky** (01:25:30): That was amazing. There was a lot of good stuff that we covered there, but I know you have to run. So before we get to our very exciting lightning round, is there anything else that we haven't covered that you wanted to cover or share? **Naomi Gleit** (01:25:42): Honestly, I think I just did it. I didn't even realize I wanted to talk about that, but it just all came out. **Lenny Rachitsky** (01:25:47): I love it. I love that. Those are the best nuggets. With that, we've reached our very exciting lightning round. Are you ready? **Naomi Gleit** (01:25:54): I'm ready. **Lenny Rachitsky** (01:25:55): First question, what are two or three books that you've recommended most to other people? **Naomi Gleit** (01:25:59): I really love narrative nonfiction, so I like the Eric Larson books. They're a very compelling and page turning way to learn about history. I recently read Devil in the White City and there was also one about Churchill's first year by Eric Larson. Another book that just the canonical book that I often recommend is Sapiens. I think he's a great example of what we talk about when we talk about simplifiers. He took a very complex subject, which is all of human history and tried to pull out the nuggets. I think his thesis that what differentiates humans from other forms of life is really our ability to tell and believe in myths or stories, and he cites money and religion as examples, but also there's a graphic novel version of Sapiens and so he almost has the PhD level and then he literally has the high school level, which is a graphic novel version. **Naomi Gleit** (01:26:57): He also has Unstoppable Us, which I think is a kid's version, and so clearly here is someone who is a master. There's a James Clear thing that a friend, Shirley, told me about where it's like if you're a beginner, you have ignorant simplicity and intermediate has functional complexity, and then a master of a topic has profound simplicity. And that's what I feel like Noah Yuval Harari really has because he can go all the way up and down this cool pyramid in terms of explaining this really complex topic. **Lenny Rachitsky** (01:27:31): What I heard about him is that he goes on a one-month meditation retreat every year where it's just him silent meditation retreat, and people ask him, "How do you have time to do that when you have so much work to do?" He's like, "The only way I'm able to achieve these books where I synthesize all of human history into a story is because I do that. Because I can clear my mind and just be." **Naomi Gleit** (01:27:53): And Lenny, to our previous conversation, that is how he himself is best. That's what he needs to do. I might need two to three hours a day and a sparring partner, Noah Yuval Harari needs a month in silent meditation. **Lenny Rachitsky** (01:28:07): Great point. Everyone has their own way of unlocking their brain. On Devil in the White City, a fun fact. When I read that, I was like, "I need to go to Chicago and see the stuff that they wrote about in this book about the World's Fair." And so I went to Chicago and- **Naomi Gleit** (01:28:21): You did? **Lenny Rachitsky** (01:28:22): Because of that book, yes. **Naomi Gleit** (01:28:25): Wow. Have you read the Splendid in the Vile? **Lenny Rachitsky** (01:28:28): Yes. That was the- **Naomi Gleit** (01:28:29): Churchill. **Lenny Rachitsky** (01:28:29): About the Telegram, right? Yeah. Right? **Naomi Gleit** (01:28:32): Oh, no, it was was Churchill's first year, but he has like six books. I haven't read all of them. **Lenny Rachitsky** (01:28:37): Okay. I think it was either that one or it was something about a telegram. I did read... It was less good though, is was what I find. I found the Devil in White City was- **Naomi Gleit** (01:28:43): The best. **Lenny Rachitsky** (01:28:44): Was the best. Amazing. Okay, we'll keep going. Second question, do you have a favorite movie or TV show you've recently watched that you really enjoyed? **Naomi Gleit** (01:28:52): We just watched Shogun. I thought it was really good. Have you seen it? **Lenny Rachitsky** (01:28:57): I have, yes. I loved it. Very gruesome but amazing. **Naomi Gleit** (01:29:01): Yeah. I was. I had to cover my eyes for some of it. And then we also, the movie that we just watched was Dune Two. Chris Cox, who's our chief product officer, actually recommended that as one of the best films that he's seen recently, and I really trust his opinion on that. So we caught up by watching Dune One and then watched Dune Two, and it was really good. **Lenny Rachitsky** (01:29:21): I watched that in IMAX Theater in San Francisco, this insanely large screen and highly would recommend that. I don't think it's still out there. Yeah. [inaudible 01:29:30] ridiculous. Amazing. I think there's another one coming someday. **Naomi Gleit** (01:29:34): Oh yeah, yeah. Dune Three. **Lenny Rachitsky** (01:29:36): Dune Three. Just keep them coming. Next question. Do you have a favorite product you recently discovered that you really love? **Naomi Gleit** (01:29:46): Well, I'm going to check out that eye mask thing that you recommended, the WAOAW thing. **Lenny Rachitsky** (01:29:49): That's it. **Naomi Gleit** (01:29:51): I know it's super expensive, but have you tried the Eight Sleep? **Lenny Rachitsky** (01:29:56): I have. My wife doesn't love it. She doesn't like the noise. It's like a very slight noise when it starts up, but it wakes her up, so we don't have it anymore. **Naomi Gleit** (01:30:07): And I noticed that too. I think maybe they just released the latest edition. One of the features that is the killer feature for me is that it does a vibrating alarm so that when I wake up at 6:00 A.M., I do not wake up everyone in the house at 6:00 A.M., and so it's a thermal alarm. It makes the bed on my side hotter and it also slightly vibrates underneath my ear to wake me up. **Lenny Rachitsky** (01:30:32): It's under your ear. I remember vibrating my whole part of the bed. I wonder if that's a new feature. **Naomi Gleit** (01:30:37): Maybe this is like... I'm on version three, maybe there's a version four. I don't know. Maybe that was version one. **Lenny Rachitsky** (01:30:43): Yeah, that's so funny. A nice thing about my life right now is that because I have no meetings or boss, I don't need an alarm. **Naomi Gleit** (01:30:52): That's awesome. **Lenny Rachitsky** (01:30:53): However, it's amazing. However, we have a young kid and he wakes up at 6:00 to 6:30, so that's my alarm usually. **Naomi Gleit** (01:30:58): Oh, and then the other thing I wanted to mention, I don't know if you have this problem, but I'm trying to get a hundred grams of protein every day. I think a lot of my friends and I are focused on protein consumption right now, and so my trainer who helped me actually do the pull-ups and the push-ups started a protein products company called Promix that I really love, and he has this Rice Krispie treat thing that I usually eat every morning and gives me 15 grams of protein. **Lenny Rachitsky** (01:31:30): I just bought that. **Naomi Gleit** (01:31:32): What? **Lenny Rachitsky** (01:31:33): Yes, I was reading, Kevin Rose had his favorite, his health stack, and I don't know if that's the brand, but it's exactly a Rice Krispie thing with 15 grams of protein. So I'm pretty sure that's it. **Naomi Gleit** (01:31:45): I'm pretty sure that's it, because the Rice Krispie part of it is very unique, so let me know what you think. I really like the chocolate chip flavor. **Lenny Rachitsky** (01:31:52): I hate them and I love them, so that's a really good tip. I just saw a funny TikTok where it's like I never thought when I'd grow up in be an adult, I'd be thinking so often about protein and how much protein I should be eating. **Naomi Gleit** (01:32:05): Maybe this is 40, I don't know. I'm not sure for me, but yes, I've been thinking a lot about protein. The other thing I really like is canned seafood, which has a lot of protein. So something called Fish Wife has, it's just Hipster, like Chicken of the Sea. **Lenny Rachitsky** (01:32:23): Oh yeah, they're very cute. Yes. My wife gets those. Another protein tip, they were a former sponsor, but no longer, but it's an amazing protein tip. Maui Nui venison beef sticks. It's 10 grams of protein and it's a delicious venison beef stick. **Naomi Gleit** (01:32:39): Thank you. **Lenny Rachitsky** (01:32:40): There we go. **Naomi Gleit** (01:32:40): Look at what we've become Lenny. **Lenny Rachitsky** (01:32:45): Just protein obsessed. It's just going to be so protein rich. Amazing. Okay, what else we got here? Okay, two more questions. Do you have a favorite life motto that you often come back to and find helpful in working life? **Naomi Gleit** (01:32:56): Last month we were watching, or I guess two weeks ago, we were watching the US Open and we discovered that as people come through the hallway to come onto the court to play, the players all passed the Billie Jean King sign that says Pressure is Privilege. And I really loved that because I think just with the Teen Accounts launch and just a lot of the more public facing stuff that I have done recently, I do, like we talked about, get nervous, and I think Pressure is Privilege just reminds me that a lot of this stuff is a really incredible opportunity that I have and to be grateful for it. I can still be nervous, but also recognize and be grateful for it. **Lenny Rachitsky** (01:33:48): I love that. Just to remind yourself that you're lucky to be feeling this pressure because that means something is important. Slightly different version of that is Zuck at the event in the Chase Center that you were also at had the shirt that said in Latin- **Naomi Gleit** (01:34:02): Learning through suffering. **Lenny Rachitsky** (01:34:04): Learning through suffering. Perfect. **Naomi Gleit** (01:34:09): Learning through suffering. I like that one too. I mean, I think he spoke a little bit about this being an entrepreneur is really, really hard. **Lenny Rachitsky** (01:34:23): They had the Jensen line about people asked him if he'd start Nvidia again, and his answer was like, "If I knew how insanely hard and stressful this was, I would not." Very, very honest. Okay. Last question. So Charles, your former colleague, told me that you're an incredible surfer- **Naomi Gleit** (01:34:42): Oh. **Lenny Rachitsky** (01:34:43): And that you design your life almost around where and when you can go surf. **Naomi Gleit** (01:34:47): Yeah. **Lenny Rachitsky** (01:34:48): Any story or lesson or I don't know, takeaway from surfing and the impact that's had on you? Lessons about surfing? **Naomi Gleit** (01:34:58): So I think surfing and life have a lot of parallels. It is an incredibly mental sport for me. The biggest thing that I can do to improve my surfing is to improve my confidence. And so when I'm going for a wave, a lot of times I will hesitate or pull back or. Instead, the best thing that you can actually do in that situation is stand up into your fear, is to ride the wave. That is the safest thing you can do. That is the thing that you're actually supposed to do, but on every dimension, that's the right thing. And so it's almost, I guess the motto there is stand up into the fear when you're going, you're about to catch a wave and actually the things that you can do when you're afraid, for example, like I said, pull back or throw your board are actually quite counterproductive and actually unsafe and could lead to more injury. And so it's just another reminder that you really need to commit. Stand up into your fear. **Lenny Rachitsky** (01:36:04): I love it. Stand up into your fear and pressure is a privilege and learning through suffering. Naomi, this was so much fun. I'm so happy that you agreed to do this. Two final questions. Where can folks find you a line? Where they find Naomi-isms, and anything else you want to point folks to and how can listeners be useful to you? **Naomi Gleit** (01:36:21): So believe it or not, I have Naomi.com. I know Boz has Boz.com. I bought that URL, I think maybe 20 years ago, 15 to 20 years ago from a farmer actually whose wife's name was Naomi rather, and his wife was not using it. And so I got it for quite a steal. And I'll just say that I've had other famous Naomis, much more famous and much more well known than I, who would like to have Naomi.com make offers for this URL. But I really like having just a home on the internet where I can put my Naomi-isms. They're also available on Instagram, Naomi Gleit. **Naomi Gleit** (01:37:03): How can listeners be useful to you? I think Lenny, I mentioned this before we got on the call, I don't tend to do that much public speaking or talking about Naomi-isms. I did some of it two years ago when we first launched but I, as a result of being on the podcast and stuff, would love to do more of this. And so I think any feedback on what listeners would like to see or hear from me, questions that would give me a reason where I felt like it would be useful for me to do more on Naomi-isms would be super helpful. **Lenny Rachitsky** (01:37:37): Sweet. So if you have any of those, leave them in the YouTube comments is usually the easiest place for folks to leave that. Naomi, thank you so much for being here. This was so much fun. **Naomi Gleit** (01:37:45): Thank you, Lenny. **Lenny Rachitsky** (01:37:47): Bye everyone. **Lenny Rachitsky** (01:37:50): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [7/17] Shreyas Doshi Live **Lenny Rachitsky** (00:00:02): Today, I am super excited to bring you a very special episode with Shreyas Doshi, recorded live at the Lenny and Friends Summit in front of 1,000 people in San Francisco. This is Shreyas' second time on the podcast. His first visit is the third most popular episode of all time of this podcast, and I love that Shreyas was game to try this. **Lenny Rachitsky** (00:00:20): In our conversation, Shreyas shares three questions plus a bonus question that he wished he'd asked himself sooner in his career. We talk about why product leaders are so busy, why the job is so frustrating, why it is so central to build good taste, and also why you're probably not listening as well as you should be. This was so much fun, a huge thank you to Shreyas for doing this. **Lenny Rachitsky** (00:00:41): If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and helps the podcast tremendously. With that, I bring you Shreyas Doshi. Shreyas, thank you so much for being here, and welcome to the podcast. **Shreyas Doshi** (00:01:01): Thanks, Lenny, for having me. This is amazing. **Lenny Rachitsky** (00:01:04): I was going to ask, we recorded our first episode, I think two years ago, and I was in a tiny room in my house. I don't know where you were, but it was very not like this. Thoughts on the setup of this episode? **Shreyas Doshi** (00:01:18): So first, the Lenny Empire keeps growing, which is amazing to see. And second, as I was coming up here, somebody told me this used to be a car dealership, and I actually realized I purchased my car here. **Lenny Rachitsky** (00:01:34): What? **Shreyas Doshi** (00:01:36): So crazy, only in SF. **Lenny Rachitsky** (00:01:38): What kind of car was this? Say more. **Shreyas Doshi** (00:01:40): It was a Honda CR-V. **Lenny Rachitsky** (00:01:42): Okay, wow. I am told this venue was also used for... Jimi Hendrix performed here, and Aretha Franklin performed here. So it's like Jimi Hendrix, Aretha Franklin, Shreyas. **Shreyas Doshi** (00:01:56): There we go, that's going up on my Twitter bio soon. **Lenny Rachitsky** (00:02:02): Okay, so usually, when we talk, you're full of ideas and you're full of answers. When we were preparing for this, you told me, "I have questions, I have questions I want to ask." **Shreyas Doshi** (00:02:16): You know, reflecting on my career as a PM leader over the years, there are some questions I wish I had asked myself sooner, but I did not, and I had the great luck of having a life, a PM life full of suffering, and I have zero complaints about it. But as I look back, I feel like there are some questions that even if I asked myself some questions, those questions, I wasn't honest to myself about the answers. So that's what I thought I'd do, is share the questions that I wish I'd asked myself sooner. **Lenny Rachitsky** (00:03:05): Awesome. **Shreyas Doshi** (00:03:06): Yeah. **Lenny Rachitsky** (00:03:06): Love that, okay. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise features, like SAML authentication and SCIM provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by WorkOS, including ones you probably know like, Vercel, Webflow, and Loom. **Lenny Rachitsky** (00:03:41): WorkOS also recently acquired Warrant, the Fine Grained Authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale, while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features, like single sign-on, SCIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to 1 million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. **Lenny Rachitsky** (00:04:29): This episode is brought to you by Paragon, the developer platform for building native, customer-facing integrations with third-party apps. Are native integrations on your product roadmap? Whether it's to ingest context from your user's external data and documents, or to sync data and automate tasks across your users' other apps, integrations are mission-critical for B2B software products today. **Lenny Rachitsky** (00:04:50): But building these integrations in-house cost an average of three months of engineering, according to the 2024 State of Integration survey, which results in difficult roadmap trade-offs. This is why engineering teams at Coffee AI, AI21, and over 100 other B2B SaaS companies use Paragon, so they can focus their efforts on core product features, not integrations. The result, they've shipped integrations seven times faster, all while avoiding the never-ending maintenance that comes with rolling your own integrations. Visit useparagon.com/lenny to see how Paragon can help you accelerate your product's integration roadmap today and get $1,000 in credit on their Pro and Enterprise plans. That's useparagon.com. **Lenny Rachitsky** (00:05:37): What's the first question? **Shreyas Doshi** (00:05:39): Right, so let's see, the first question is why am I so busy? Why am I so busy? And the background is that I have spent most of my career just being completely stressed out, just absolutely stressed out every day. And there were many reasons for it, but one of the core reasons was I was always super busy, and there was always work I felt like I couldn't do that I wanted to do, and so I would go home at the end of the day, and even if I had worked hard, I'd just feel dissatisfied. **Shreyas Doshi** (00:06:27): And so that was a constant fixture of my life as a PM, PM leader, and it's only... So I did product work for about 20 years before I started this new chapter of my career. And I think I only fixed it in the last three or four years of my career as a PM leader. But that means that there were about 16 or 17 years where I was just incredibly busy, and because I was incredibly busy, I was extremely stressed, and even though I was doing a good job, I was not feeling very good inside. And then, that showed up in my body, like all sorts of pains and aches I realized were actually not physical pains and aches. They were pains and aches from the stress. **Lenny Rachitsky** (00:07:15): It's like health issues that you had? **Shreyas Doshi** (00:07:16): Yeah, yeah, minor stuff. I mean, relatively minor stuff, but playing tennis, and you pull your back muscle, and now you are horizontal for three days, doesn't feel good. **Lenny Rachitsky** (00:07:31): Who here is very, very busy, and is just way too busy? Raise your hand. **Shreyas Doshi** (00:07:36): That's it? **Lenny Rachitsky** (00:07:36): Yeah, I know. **Shreyas Doshi** (00:07:37): Whoa. **Lenny Rachitsky** (00:07:39): Everyone's like [inaudible 00:07:39] everybody. Yeah, people were like, "Yeah, yeah. I don't have to raise my hand, I'm busy." Yeah. Okay, keep going. **Shreyas Doshi** (00:07:50): Yeah, and so here's the thing, when we talk about being busy, and managing your time, energy, all of that, I mean, this is a group of senior product people, so you all know that. Take tips and techniques, like maintain a to-do list. I found the LNO framework very useful for me, which I've shared before. I used to like working out of a calendar, those types of things. And I think you're all familiar with those things, but what I wanted to call out is that, at some point in our product career, we reach something, we reach an immovable force that will just overwhelm us, no matter what we do. **Shreyas Doshi** (00:08:39): And that force is a scope. Okay, so as we grow in our product career, our scope grows, and we kind of like that, which is all great, but at some point, if you haven't already gotten there, many of you have, but for those of you who haven't, you will get there, where your scope will be so large, that no matter what you do in terms of efficiency, whatever framework you use for prioritization, whatever framework or tool you use to manage your to-do list, whatever tools and techniques you use, whatever prioritization you do, your scope is so large that you are still going to be incredibly busy. **Shreyas Doshi** (00:09:21): And so that's what I faced, like I was saying for the first about 16, 17 years of working on products, and only in the last 3 or 4 years was I able to kind of find some answers on how to deal with that scope. And so perhaps we can talk about that, what do you think? **Lenny Rachitsky** (00:09:43): Yeah, so you're basically saying there's all these productivity tricks, ways to do more faster. And no matter how many of these tools you've got, you are just going to take on more and more work, and they'll peter out? I'll say many of my most popular newsletters posts are, "Here's productivity tricks and tips." And so people are always looking for these. And I'm curious to hear where you go with this, of just like that is not the answer long term, there's a different approach? **Shreyas Doshi** (00:10:08): Yes, and so the challenge is the following. How many of you are going through some kind of annual planning right now or you're planning on going through annual planning? Please. Everybody loves annual planning, great. So let's take annual planning. If you are a high-level manager, leader within a company, what does your month look like? Or in some cases, unfortunately, what do your two or three months look like when you are going through annual planning? It's all these kind of spreadsheets to fill out, and meetings to have, and dependencies, and priorities, and stakeholders to meet, and so on. And so I noticed, for instance, that at some point, that was making me really busy, and then that was making me feel guilty now, because I had my team to look after and to support, and then I had product decisions to make and various other things, and I've gone on some planning retreat or whatever. **Shreyas Doshi** (00:11:15): And there you go, you last four, five, six, weeks, does that sound familiar to folks? Yeah? Okay, so I noticed that I needed to change that at some point, and actually found a solution, again, late in my career, but I found a solution, because I asked myself this question, which is, "Why am I so busy? I'm doing all the efficiency things, I'm managing my to-do list like a champ. I have my calendar set up just right. I have my routine set up just right. I'm working out so that I'm engaged at work, I'm productive, I'm doing all of that. Why am I so busy? Oh, it's planning season, and that is supposed to take up four to six weeks." And this was at Stripe when I encountered this. So that is supposed to take up four to six weeks. **Shreyas Doshi** (00:12:03): Well, I realized that you don't have to do that. And so at some point in my time at Stripe, what I realized is the following, we go through a whole all sorts of just rituals around planning for four to six weeks. Then, we emerge and we share our plan with our executives. You know the questions they're going to ask, like, "If money were no concern, what would you do? What is your ambitious plan? So if we gave you five more engineers, what would you do? What other things would you include in the roadmap?" Right? The standard stuff. And so you emerge, you do your presentation, and then you publish the plan, and then you start the new year with a lot of enthusiasm and a lot of excitement. And January goes fine, until you get three customer escalations for features that were not in your plan. And so now, you try to figure out how you're going to revise resources. **Shreyas Doshi** (00:13:03): You go talk to some dependency team that's going to sort of support these new features from these customer escalations. And you go through that process, and you revise your plan again. And then, usually by the time it's last week of February, everybody's forgotten the actual plan. And now, we are executing off of some other list somewhere. And by the way, when you mention this at times, politely of course, you might mention like, "You know, I'm noticing we are not actually really using the plan that we spent four to six weeks minimum doing." And then, some smart person in the room chimes in with, "Plans are useless, but planning is everything." **Shreyas Doshi** (00:13:52): I don't know, Eisenhower, somebody else, I don't know who said this, "Plans are useless, but planning is everything." Nobody knows what it means. Nobody knows what that means, but everybody appreciates, "Ah, plans are useless, but planning is everything." Right? So I went through a few years of this. And then I go, "You know what? I'm going to bend some rules here." And so what I realized, Lenny, is you don't have to go through these four to six weeks, and it was an accident. Basically, what happened is around that time, the product I was working on, Stripe Connect, it's like a major product for Stripe, major, major business for Stripe. And I had put together a product strategy, like a real product strategy for this product. **Shreyas Doshi** (00:14:44): And so this must have been earlier in the year. And so now, planning season came along. And the interesting I found is that because I had a real product strategy, not one of those fake ones, a real product strategy that I had gotten alignment on with everybody, my planning for this major product for Stripe took me like three days. Right, so while a lot of my peers, unfortunately, for their own products, were in this four-to-six week cycle of planning, and meeting, and blah, blah, blah, I just put it all together in three days, and whatever artifacts were needed, I put them together. **Shreyas Doshi** (00:15:27): I did not fill out some templates. That's where it's about bending the rules, because if a template doesn't make sense, why should I fill it out? There's no need to fill it out. And so that's when I realized that actually, if you have a real product strategy, a real one that everybody is aligned with, that you have got pre-alignment on, then a lot of this nonsense we tend to do with annual planning actually goes away. Now, you still have to do some resource allocation and all of that, but even there, you don't need that false precision. How many of you have gotten into arguments about, "So should it be eight engineers for this team in 2025, or nine engineers for this team in 2025?" **Shreyas Doshi** (00:16:11): Like, who cares? We all know that even those numbers that we set up, we don't actually follow through on them, as 2025 happens. So that's just an example of where we spend a lot of time on things that we think are strategic, that we think are important, but actually, we ought to spend that time on other much higher leverage things. Right, now it does require some upfront work, in this case upfront work on a clear product strategy that everybody understands, that everybody's aligned on. But frankly, if you have that, planning should be a breeze. **Lenny Rachitsky** (00:16:49): So what would be your kind of tactical tip for folks that want to do this better? I know there's probably a billion examples of these sorts of things you shared, so planning is an example. Folks that want to be less busy, maybe on that one is it give yourself very little time, and focus on strategy, and let that be the plan, basically, versus every single person and their roadmap for the next six months. What's the piece of advice you'd share there? And then, I want to move on to the next question, because I want to make sure we get through all these questions. **Shreyas Doshi** (00:17:18): Yes, there's definitely a specific tip, which is if you do have a strategy that will make a lot of your prioritization problems go away, it will make a lot of planning problems go away. And even if you do have some escalation from sales, which you will, or from support, or somewhere else, you now have at least a more rigorous framework to figure out what to do with that escalation. So there's definitely that. **Shreyas Doshi** (00:17:48): But I think other thing I want to share is that, and this was my other realization as I asked the question, "Why am I so busy?" is I realized that I am so busy because I'm not making good product decisions. Okay, now, you have to understand, by this time I'm like 15 years into building products and whatever, 11 years into being a product manager. And so I think I'm pretty good. That's my kind of self-image. But then, again, if I'm being honest to myself, I'm not making as good product decisions as I can. So can I share an example of that? **Lenny Rachitsky** (00:18:32): Please. **Shreyas Doshi** (00:18:34): So what I noticed is that you have a meeting about some product feature that somehow is requested or is really important, whatever the case might be. And so you have a meeting with some stakeholders and your engineering team, designers, et cetera. And then, you're trying to decide, "Should we build this or not?" And somebody says, "You know what? Why are we doing a meeting for this?" I read somewhere or I heard Bezos say that two-way doors, it's a two-way door. You quickly make a decision. Like, just quickly make a decision and move on. This is a two-way door. And so you say, "Yeah, that's right." And any time we hear something like that, two-way door, you're like, "Oh, that person's really smart, so I want to be like them." **Shreyas Doshi** (00:19:32): So I noticed that myself and my team, we were making these kinds of decisions without very clearly thinking through customer motivation, very clearly thinking through differentiation, very clearly thinking through a distribution approach for whatever this feature is. And while it sounds like, "Oh, of course you should be doing this," I guarantee you this is not how most product teams work. They're talking about, "Well, is Bob the engineer going to be free? And when are they free? And if they are free, then let's build the feature." That's kind of how a lot of product decisions happen. **Shreyas Doshi** (00:20:11): The challenge here with this kind of approach, and again, this is what happens in practice, I'm not talking about whatever theory you read, this is what happens in practice. So when you follow this approach and you assume that, "Oh, this is a two-way door, we can kill the feature," in reality, it doesn't work out that way, because here's what happens in reality. So in reality, you commit to the feature, and it's going to take five, six weeks to do it, and then a couple more weeks to make sure, to ramp it up, et cetera, right? And so now the feature is out, and now you have your Q1 QBR, right? Say two months from now you have your Q1 QBR, and you're going to present your business review, whatever. You're going to present what you did, "What did you do last quarter? How are your ships performing from last quarter?" **Shreyas Doshi** (00:21:03): And so now, it's time to talk about this feature at the QBR, because you have to share that/ Now as you start talking about this feature, the CEO will ask, "So yeah, we launched the feature. I'm very glad we launched this feature. How is it doing?" And you want to be able to say, you are the PM leader, you want to be able to say something smart, and something that makes you look competent. But the challenge is the feature hasn't had much adoption. So I'm not going to ask anybody to raise hands, but I think most PMs are familiar with this conundrum. And of course, we are verbally very agile as product leaders. So what we say is we don't have data, so we use favorable anecdotes. **Shreyas Doshi** (00:21:53): And so we say, "Yeah, we launched the feature, and you know what? This customer from this company really loves the feature." And we put in an anecdote, it's like, "Life-changing feature." It doesn't matter that they're the only person using it. That doesn't matter. "Life-changing feature," right? We use data when it favors us, we use anecdotes when it favors us. So anyway, so we present that. Now. we do have the sales counterpart in the room too, our sales counterpart, and they say, "You know what, though? We are still not winning many deals because of this feature." And so of course the CEO asks, "So what's up? Why aren't we winning deals, even though we have the feature?" **Shreyas Doshi** (00:22:30): So the people on the customer side usually we respond, "Well, I'm glad we have the feature, but it's not full featured yet. We need all these other bells and whistles to meet the table stakes." So now, what happens? Somebody uttered the word, "Meet the table stakes." Now, it's over for you, because now, the only response you can give is, "Oh, yeah, that's already part of the plan." And now, you put your engineering leader on the spot and you say, "Alice, isn't it? Haven't we allocated engineers to it already?" And so now, Alice has to come up with some response, which is like, "Yeah, yeah, yeah, Carol and David are going to work on it. It's slotted for one of these sprints." **Shreyas Doshi** (00:23:19): And so now, you exit the QBR, you high-five each other. Well, "Good job, team, great job," et cetera, et cetera. But now, you have signed up for even more work for a feature you should not have built in the first place. That's why we're busy. And through a product leader's life, what happens is we just accumulate all of this debt, feature after feature. So I guess what I'm saying, Lenny, is one of my other tactical tips would be sometimes it is useful to pause for two minutes, or two days, or two weeks before making that decision, right? Because frankly, most doors that look like two-way doors are actually one-way doors. They are two-way doors at Bezos' level, but as a PM leader, for you, they are a one-way door, and that's making you busy. **Lenny Rachitsky** (00:24:18): Wow. I feel like you're a stand-up comedian/product manager. That was incredible. **Lenny Rachitsky** (00:24:28): This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now, you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance, alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta AI. **Lenny Rachitsky** (00:25:02): Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's vanta.com/lenny. **Lenny Rachitsky** (00:25:21): I know it's Spotify, I heard one of their core values is, "Talk is cheap," but it's the virtue version of that. It's like, they actually prefer to talk more, and I think that's exactly what you're saying. Basically, spend more time on these things that seemingly seem just small little ideas and experiments. **Shreyas Doshi** (00:25:37): Yep, thinking is cheap, so you should do more thinking, not less. **Lenny Rachitsky** (00:25:41): Amazing. Shreyas, what's your second question? **Shreyas Doshi** (00:25:45): Yes. So my second question, I have to get the words right, do I actually have good taste? Do I actually have good taste is my second question. And for me, I asked this question after, again, all of these things... By the way, everything I say, I have been that guy, I've made that mistake. So that's why I just have to admit to myself that, yes, I have made these mistakes. And one of the mistakes I made, this was when I was at Google, and I was relatively new to product, about less than five years. And at Google, there's some parts of Google where you would be told as an early career PM that like, "We don't do strategy here. Strategy is for MBAs, okay? We are all about execution, okay?" **Shreyas Doshi** (00:26:47): So I'm in this environment, I'm naïve, and I look around me and I'm like, "Google is the most successful company on the planet," at the time, and they are saying this, and I'm hearing this consistently, so it must be right. It must be right. And so I start saying it. I start saying, "Oh, yeah, execution is everything, and we don't do strategy around here." And I even remember there were not that many PMs, but there was a PM at Google who was kind of like the same level as me, but he just had much more wisdom than me. And he was trying to nudge me into... Like, I was managing a product. And he's like, "Shreyas, what is your strategy here?" And I was like, I told him the same thing. Like, "Oh, no, no, what are you talking strategy? We don't need strategy. We just need to get shit done." That was the thing. **Shreyas Doshi** (00:27:42): And so I kept repeating that mantra until I got to Twitter. So this is Twitter right after their IPO. And I saw Twitter had an incredible asset, which is the product and the network effects. It had other incredible assets, including the brand. It had other assets that were great, including the talent. And yet, this company was struggling, the product was struggling. And even if it wasn't struggling, it was making a lot of money. But the point is it was not meeting its potential. So that's when I realized, and it wasn't like some sudden realization, it took me six to nine months of being at Twitter. This is circa 2014. That's when I realized that, "Oh, my gosh, Twitter's biggest problem is a product strategy problem. The reason they're struggling is they don't have a real product strategy." **Shreyas Doshi** (00:28:38): Now, of course, attempts were made to create a product strategy, but it wasn't a real compelling, cohesive product strategy. So that's when I realized the folly of like, "Oh, wait a minute..." I was at Google six years. I spent most of those six years saying like, "Ah, strategy's useless. There's no point to strategy. Execution is where it's at. "I'm like, "No, actually, I was wrong." And that got further solidified as I went to Stripe, and I was kind of now growing earlier stage products and trying to make them highly, highly successful. I saw an even greater value and importance of having a clear strategy. And so that made me realize, basically... **Shreyas Doshi** (00:29:29): You know, we talk about taste, we all talk about taste, and it's about the beautiful pixels, and the perfect product, and the whatever else, the Steve Jobs-esque passion, and all of that, whatever it is. And yes, taste is about that, but I think there is something that we as product leaders, and certainly I did, needed to recognize about taste as just a factor in pretty much everything we do, which is like, do we have good taste around the beliefs we choose to create within ourselves as product leaders? And then, those beliefs end up dictating everything we do, including how we manage, how we lead, how we make decisions. And so it's that taste I'm talking about when I say, "Do I really have good taste?" **Shreyas Doshi** (00:30:28): And when I asked myself this question, and again, I really had to dig deep. It wasn't easy, but at some point I realized that no, actually, I don't have good taste. I don't have good taste in how I choose to evaluate things that come my way. Again, not in terms of the product, because by that time I had skills to say, "Well, this should not be a two-step flow. This should be a three-step flow," whatever the case may be. But I still did not have good taste in terms of how I choose what are the things I choose to believe, how do I learn, who do I learn from, what content I learned from, what content I resonate with? And then, I went on this journey to try to develop that better taste. **Lenny Rachitsky** (00:31:21): What I'm hearing is people focus maybe too much on the output, like the experience, these experience design taste versus what they choose to take in as informing their taste, and what they see as an example of great and correct. Is that what you're saying? **Shreyas Doshi** (00:31:37): Yeah. And look, taste is about the ability to identify what is really good, without needing to see its results, because, look, it requires zero taste right now for anybody to say, "Oh, that CEO of NVIDIA is a genius, right? Jensen is a genius." If you are saying that in 2024, it actually requires zero taste, because you can just look up NVIDIA stock price. It requires zero skill. But to be able to say that in 2010, you have to realize Jensen Huang didn't change much between 2010 and 2024. So Lenny, even in sports, there's this saying, "Game recognize game," and that's about taste. **Shreyas Doshi** (00:32:59): But what we need to understand is it's game recognize game before the game is called, right? Like, game recognize game in the practice session. Because it takes no genius right now to say, "Well, Patrick Mahomes is great quarterback," or, "Virat Kohli is a great cricketer," or whatever else. It requires no genius to do that. It requires zero taste. So I also believe some of us, especially as we get more senior, and we get more successful, and we just get a lot more scope, and responsibility, and a lot of accolades, we become these tough graders. Like, "I don't like anything," right? Like, "Ah, this is crap, this is crap, this is crap." Again, that requires zero taste. Anybody can say that. Anybody can just say, "Everything is horrible." **Shreyas Doshi** (00:33:53): So I do think there is something about being able to understand that, and I think I'll share some examples. This two-way door thing, so let me just share a few observations, if I might. So the first one is we get overly excited about cool metaphors, okay? Like, one-way door, two-way doors. There's some guy, I don't know who it is, I just read somewhere, there's some guy who had written a blog post about this idea, but he called it reversible and irreversible decisions, and it was the same idea. And I think somebody was lamenting that that did not catch on, reversible and irreversible decisions. But what caught on is two-way door and one-way door. What's the difference? The only difference is you got attracted to the catchy metaphor, and the other one is the authority bias, because Bezos said it. **Shreyas Doshi** (00:34:58): Take another example, we get very impressed with alliterations. I'm serious, we get very impressed with alliterations. Okay, so how many of us love fail fast? Fail fast, okay, nobody's going to raise hands now. Okay, fine. Maybe you truly don't love fail fast. How about fast follow? How many of you love fast follow? Let's consider that, like fail fast, "We're going to fail fast." What if that thing were called fail quickly? It's the same meaning. Do you think you would be as attracted to that idea if it were called fail quickly? **Lenny Rachitsky** (00:35:44): No. **Shreyas Doshi** (00:35:46): Probably not, so what changed? The only thing that changed is one is an alliteration. So I see this in everything. Like, let's see, the other one is we also get very impressed with complicated charts and math we don't understand. And some of you product leaders who are at the top of the game, you actually use this as a strategy. So as I realized that here's the outcome of that, asking myself that question, was that what I realized is everybody says, "Oh, I'm a first principle thinker. I am a rigorous thinker," whatever. **Shreyas Doshi** (00:36:41): But I realized that if I really want to be that, I have to shed a lot of these just patterns that were just built in me, and I kind of have to evaluate the idea separate from all of its social proof, and authority proof, and whatever else. And that ended up being a meaningful change in my growth as a product leader, because the moment I started shedding these kinds of social proofs, and authority proofs, and all of that, it just made me a much... We all again think we are critical thinkers, but we are not, right? So it made me a more critical thinker. **Lenny Rachitsky** (00:37:31): I want to move on to the next question, just so we can get through some of these questions. Before I do, can you just show people your notes real quick, just like show it from a distance? This is how Shreyas plans for something like this. There's color coding, I wish I understood what was going on there. **Shreyas Doshi** (00:37:49): People ask me, "What's your favorite note-taking app?" It's a common question I get, and I say this, right? It's a $5... Like I guess the pen costs $3, and I think the Office Depot clipboard costs- **Lenny Rachitsky** (00:38:00): Wait, doesn't that pen... Does it have the different color clicky thing? **Shreyas Doshi** (00:38:02): Yes, yes, yeah. A [inaudible 00:38:04]. Yeah, exactly. This is great. **Lenny Rachitsky** (00:38:06): That's going to be another podcast episode. Okay, so we want to try to do two more questions. We have six minutes left. The last one's a bonus, so maybe we touch on it briefly. Shreyas, what's your third question? **Shreyas Doshi** (00:38:18): So my third question is why does my job feel so frustrating? Why does my job feel so frustrating? And it goes back to the point that, look, I loved, loved my PM leadership job. I just absolutely loved it. And I think looking back, I would not have exchanged it for anything else, any other experience. That said, there were daily frustrations. There were daily frustrations in that job, and a lot of it has to do with the fact that the PM leader's job is extremely lonely. The PM's job, the PM's on your team, their job is also lonely. But a PM leader's job is further lonelier. So there's that. There's also what I learned at the time when I started asking this question is that our jobs get frustrating when we behave, most of the time, in misalignment with our superpowers and who we truly are at our core. **Shreyas Doshi** (00:39:32): Okay, so for me, as I was evaluating that question, it's like, "Why am I getting frustrated every day? I love the job, I love the macro, but I do not like the micro. And so why is that?" And that's when I actually... There's a simple framework that I've shared, which is you can be doing your work at three levels. Product work happens at three levels. There's the impact level, there's the execution level, and there's the optics level. My epiphany as I was exploring this question was I have a preferred level at which I like to operate, but if most of the day, and most of the week, and most of the month, I am forcing myself to operate in not my happy place, in my non-default level, that makes me very frustrated. **Shreyas Doshi** (00:40:33): So many product leaders, their happy place is the execution level. In my case, my happy place is the impact level. So that is fine. Your happy place can be whatever level, it doesn't matter. But the point is, as you go higher up in the corporate ladder, no matter what kind of company it is, you are now going to have to spend a lot of time on optics, at the optics level. And I have willpower, I have the skills to do it, I have all of that. So it's not about willpower or skills, but willpower is finite. So as I spent day in and day out, just mostly doing optics work, I realized I was not happy and I was getting frustrated. And so that's when I realized the solution, which is I have to abandon the traditional path, that like, "Oh, after this level, I'm supposed to do this, and then I'm supposed to do this, and then this is what society expects. This is what my mom expects. What will people say on LinkedIn when they see my LinkedIn profile?" Like, "Oh, he has this progression, this, and then what stopped? Why did it stop?" **Shreyas Doshi** (00:41:49): So when I realized this, I said, when a team grew to a certain size, so when I was at Stripe and I realized this, when the team I was managing, it had a fan out of about 50 people, so this includes engineers and everything, I said, "This is enough." Because for me, any time a team goes to like 50s, and 100s, and beyond, it is a law of corporations that you're going to have to spend a lot of time at the optics level. So instead of just pushing, pushing through against who I truly am, what did I do? I just went back to more of an earlier stage product, and then I was fine with like, "You know what? I'm not going to just play the corporate game," as an example. **Shreyas Doshi** (00:42:34): So I guess my suggestion would be identify your superpowers, and like Shakespeare said, "To thine own self be true." Just be honest to yourself. Operate your career and make your career decisions not out of expectation, not out of envy, like the LinkedIn envy of like, "Oh, this person is at a different level. We both went to the same grad school, so I got..." No, identify your superpowers, because if you identify your superpowers and work in accordance with them, you will do the best work of your life. You will love it, and you will be great at it, and you won't have that frustration. **Lenny Rachitsky** (00:43:23): I wish we had an hour for every single one of these questions, I feel like there's so much more to get into. We have 40 seconds. Do you want to touch on your last question or do you want to leave that for a follow-up discussion? **Shreyas Doshi** (00:43:35): Let's touch on it, let's touch on it. **Lenny Rachitsky** (00:43:37): Okay, we got to go though in 30 seconds. **Shreyas Doshi** (00:43:38): All right. My last question is am I really listening? Okay, and this is perhaps the hardest one for me, because I thought, of course I'm a good listener because I listen, then I recap, and I make eye contact, and I tell them, "This is what I heard," And all of that nonsense. I realized there is an entirely other level to listening, which once you understand that there's an entirely other level to listening, that is what enables you to be a world-class leader. And so that is what I guess my last takeaway is, is ask yourself, "Am I really listening?" If you want resources, there are very few people who actually talk about what that real listening means. I would refer you to what Rick Rubin says about listening, I would refer you to what [inaudible 00:44:30] said about listening, and what Drucker said about listening as some pointers. **Lenny Rachitsky** (00:44:36): Amazing. Shreyas, you said you were going to hang out for the next hour somewhere. You want to share that real quick, and then we'll get off? **Shreyas Doshi** (00:44:42): Yes, I will maybe try to hang out in the back part of the room. **Lenny Rachitsky** (00:44:46): Be quiet back there, too. **Shreyas Doshi** (00:44:47): Yes. **Lenny Rachitsky** (00:44:47): Shreyas, thank you so much for being here. **Shreyas Doshi** (00:44:50): Great, thank you. Oh, should we take a picture? **Lenny Rachitsky** (00:44:54): Oh, yeah. We're going to take a quick selfie. **Shreyas Doshi** (00:44:59): We're going to take a picture. **Lenny Rachitsky** (00:44:59): There we go. They're going to turn lights on, I think. **Shreyas Doshi** (00:44:59): Oh. **Lenny Rachitsky** (00:45:00): Okay. **Shreyas Doshi** (00:45:03): All right, folks. **Lenny Rachitsky** (00:45:07): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [8/17] 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google **Lenny** (00:00:03): There's no one out there today who shares more wisdom, more consistently on the art of product management than Shreyas Doshi. Shreyas came out of nowhere a few years ago and started tweeting gems of insight about building product and the role of product management, and rightfully so, has built a huge following on Twitter. What I love about Shreyas is that his insights are often framed in really memorable and interesting ways and they're often contrarian and not ideas that you've heard elsewhere. Shreyas has worked at some of today's most important tech companies, including Yahoo, Twitter, Google, and most recently Stripe, both as an IC and a manager. And his advice is always rooted in his real life experiences at these companies. **Lenny** (00:00:48): In our chat, we focus on five topics and go deep on them. We talk about the power of pre-mortems. We talk about how to best use your time as a product manager. We look into the three levels of product work and how getting them wrong often leads to tension on your team. We dig into why most execution problems are really strategy problems. And we talk about a common pitfall in prioritization. And if you listen to the end, we actually throw in a bonus topic. I really appreciate that Shreyas made the time for our chat and I cannot wait for you to hear it. **Shreyas Doshi** (00:03:48): It's great to be here, Lenny. **Lenny** (00:03:49): So we strategized about how to make this podcast as concretely useful and actionable for as many people as possible. And so, we decided to do is instead of a regular interview where we talk about a lot of stuff, instead we're going to go deep on five of your ideas, teachings, lessons that you've shared on Twitter that have stuck with me, and I know have resonated with a lot of other people and we're going to call it the five big ideas from Shreyas Doshi. Does that sound about right? **Shreyas Doshi** (00:04:14): Sounds great. **Lenny** (00:04:15): Okay, cool. So before we get into that, before we get into the meat of all this stuff, you share a lot of wisdom on Twitter, but you don't share a ton of about yourself and your background, where you grew up, where you're born and things like that. So I'd love to learn a little bit more about the human that is Shreyas. And so, maybe we start there, where were you born, where'd you grow up, what'd your parents do for work, what did you want to be when you grew up? **Shreyas Doshi** (00:04:36): So I was born in Mumbai, Bombay, India, and I lived there for the first 21 years of my life. I actually did not really even get to see many parts of India while I grew up in India and basically just was in Mumbai the whole time. And then I moved here to the United States for graduate studies at age 21. My parents, my father was a businessman, and so, he started his own business. He manufactured spices and marketed them. So growing up, I saw him work on packaging and pricing. And when he was short on staff, I used to be packaging the spices into the little box or creating some marketing material for him, not the creative part, but the grunt work. So I grew up in that environment where the lines between what was my dad's business and our personal lives were very blurred. **Shreyas Doshi** (00:05:32): My mother just growing up as a homemaker, and so, my dad was largely just busy and all consumed in his business. And I ended up spending a lot of time growing up with my mother. And so, both of them have had a pretty significant influence in different ways, but both significant influence on who I am. When I grew up, I changed that a lot. I think when I was very young, one of my uncle is a doctor, so I saw him and I was like, "Oh, maybe I should be a doctor." And at some point later, I changed that. In high school, I took French and I ended up being really good at it, surprisingly good at it, and I was very passionate about it. **Shreyas Doshi** (00:06:10): So for a while, I was thinking, "Oh, I'll maybe teach French after graduate from college. Maybe I'll go to France, learn the language a little more. And maybe I'll teach French." That lasted for a few years and turned out that I ended up not pursuing that, and instead, got a degree in computer engineering. Partly, I think because in India back then, if you were good at science and mathematics, you would usually take up engineering. And so, that's what I ended up doing. I was also quite passionate about computers, so maybe that was part of it. But once I started on that path, it became much clearer what I wanted to do. **Lenny** (00:06:50): How's your French these days? **Shreyas Doshi** (00:06:51): Very bad. Sad to say, my son is now taking French and I am just embarrassed at my inability to assist him in any way, other than to point out some conjugation errors. **Lenny** (00:07:04): So you said you studied computer engineering, that's what you moved to the US for, how did you move from that to product? **Shreyas Doshi** (00:07:11): So, I started my career as an engineer, or well, backtracking, so I completed my undergrad in India, came here to the United States to pursue a PhD in computer science. About one month in, I realized that PhD in academia wasn't for me, so I decided that I was going to drop out of the PhD program. And once I dropped out, this was like 2001, 2002 so the climate was very different, there were basically no jobs for tech people. Certainly there were no jobs for people who required a visa, which I did. So it was very difficult, but I ended up working as an engineer at a couple of startups and that started my career in tech. I was an engineer for about four or five years. And when I moved here to the San Francisco Bay Area, I got a little taste of product management. **Shreyas Doshi** (00:08:00): So, I was part of this team that used to be Loudcloud, and they were acquired by a larger company EDS at that time, so it was a startup team within a larger organization. And I was an engineer there and I just started doing some product work. And I found that my managers over the time would send me to customer meetings. We had an internal product, so these were internal customers. And I thought it was a little surprising because I was fairly junior and I was an engineer, but I was like, "Okay, I'll just go to the customer meetings." And I really enjoyed that. I really enjoyed understanding what our customers were trying to do, helping them out. I also enjoyed thinking about creative ways to solve their needs and whatnot. So, that was my taste of product management. **Shreyas Doshi** (00:08:40): For about a year, I was doing the product job without having the title and I was also the engineer. So I was in this great state where I'd figure out what needed to be built and I would just build it myself. So, that's how I started. And at some point during that one year, I realized that while I was a good engineer, I was perhaps a top 20% engineer. I realized that I would never be a great engineer, that I would never be a top 10% engineer because I saw those engineers, the fortune of working with them, and I just could tell that I couldn't be that. And I increasingly got interested in this product thing, so I said, "Okay, let's try out this product thing." And so, that's really what started my product career. And I think what I have to be really thankful and grateful for there is the people who gave me a chance to do the product work and there were many people involved. And so, I think without their support, it would've been much harder for me to become a product manager. **Lenny** (00:09:34): I didn't know that you moved from engineering to product and your journey is very similar to mine where I was also an engineer. And once I got to Airbnb, I was like, "Okay, I am not good. And I will not last as an engineer at a company like this. And I should think about what other options exist." And it worked out great. And so, I wonder how often that happens of PMs moving into PM because they aren't going to make it as an engineer. **Shreyas Doshi** (00:09:57): I think it might be a common occurrence because engineering is a really great job, particularly on empowered teams, as an engineer, you can do a lot. You don't have to just write code, but you can do a lot. And so, I also think it's a great place for people to start their career if they have a technical background and if they enjoy the part about building software. Because sometimes people will ask me, "Hey, I'm doing this technical degree, whether it's computer science or something else, but I want my first job to be product management." And I often respond with, "Tryout engineering because, again, in many companies, fortunately these days you can do a lot more than just the core engineering job. And so you get exposure to many different things. And once you do that, you can decide what path to pick." **Lenny** (00:10:44): It's such a bonus to have that background as a PM. I wanted to go back, so you mentioned that you worked at Loudcloud. I had no idea. That was Marc Andreessen's second company, right? **Shreyas Doshi** (00:10:53): Yes. I joined that team. Again, this was a time when there were very scared jobs in the valley and I was interviewing with them for nine months or something like that, and they had just been acquired by EDS. So they split into two companies. One got acquired by EDS and the other became Opsware, which was the product company. And so, I joined the Loudcloud part of that organization. **Lenny** (00:11:17): Got it. Is there something that you took away from that company? Was Marc Andreessen still working there? And I think Ben Horowitz also. **Shreyas Doshi** (00:11:24): Yeah, they were still there, they were working on the Opsware side. Again, because even though I was hired as an engineer, the non-engineer task I was given was to manage a relationship with Opsware because the way that split worked is EDS would use Opswares data center automation technology, and my team was responsible for deploying and supporting that technology for EDS. And so, I was given this role of managing the vendor relationship and I have no idea. I'm in my early 20s, I have no idea how to manage vendor relationships, but I ended up doing that. **Shreyas Doshi** (00:11:59): And as part of that, I got an opportunity to work with many folks over at Opsware, including folks on the leadership team there. And that was my first experience of what a really highly talented and energetic team looks like, both on the Opsware side, like I said, I worked with a number of people there, but also on the former Loudcloud side who were my team members. And that magic, a very high caliber team, people who really great at their job and brought high degree of energy and collaboration to their work. I was just lucky to have been part of that team early on. **Lenny** (00:12:32): And then following that, you worked at a bunch of really important well run successful companies, Stripe, Twitter, Google, Yahoo, what's one thing you took away from each of these companies that you've worked at that has stuck with you? You share a lot of this on Twitter, but if you just think about somebody took away from each of these companies or even the founders that ran these companies, what might those be? **Shreyas Doshi** (00:12:53): Yeah, let's do this rapid fire style because you know me, I could spend an hour just talking about this topic. But just starting with Yahoo, I think I learned the importance of building multiple services under a single account. I think that was the one Yahoo ID was such a powerful thing. It wasn't easy to pull off back in the day and Yahoo was perhaps the first company that pulled it off really well. And so, that idea of bundling under a single account, which then Google really did extremely well later on was something that I got to experience very first hand because I was working on the identity team at Yahoo. Google taught me the. **Lenny** (00:13:33): Real quick on Yahoo because it makes me think about it. I remember they tried to do that with Flickr and they had a bunch of trouble with that, people on Flickr didn't want to log in with Yahoo, is that right? **Shreyas Doshi** (00:13:42): Yes. That's the story of every acquisition that are some raving fans of the service that are perhaps not entirely happy about their beloved service being acquired by a large company. In fact, we encountered this at Google as well. If you remember YouTube accounts used to be separate from Google accounts or Gmail accounts. And at some point, Google decided that you should be able to use your Google account to log into YouTube, and also over time, that everybody who uses YouTube should have a Google account. So they went through a multi-year migration of accounts, and they had similar backlash. The interesting part though, is nobody remembers that now, people happily use YouTube. So this is one of those things where sometimes it's painful in the short-term, even though it might actually be the right answer over the long-term. **Lenny** (00:14:36): Great advice. Okay. Sorry I cut you off. Google. **Shreyas Doshi** (00:14:38): Yes. Google, I think the main thing I learned was the power of thinking really big. And I know it sounds like a platitude, but really big. And I only actually realized that when I left Google and I started working with the other teams and these were all capable teams and I was struck by how many teams just limited the potential of what they could achieve. And I think Google helped people think big by default. And so, I think the six years I spent at Google really helped me understand that really well and just make it a normal part of how I operated. So that was really useful for me. **Lenny** (00:15:18): Is there an example at Google that some of you worked on that was like, "Holy shit. This was going to be big or let's think bigger about this"? **Shreyas Doshi** (00:15:25): Well, as with anything, there's pluses and minuses. So I worked on the ads team at Google for a number of years and there was this unwritten rule of thumb that, hey, if it's not going to generate more than $100 million in revenue, it's not worth talking about it. Because the ads business was growing so fast and was so large that we would regularly not pursue opportunities that were just quote $100 million. So why do that? That's because Google had access to billion dollar opportunities for it as business. So they were very clear on pursuing the big opportunities. And in some cases, these opportunities were not obvious, so we had to create those opportunities. If you think about some of the innovations Google brought over the years in monetization, including things like video ads and whatnot, those were not obvious opportunities, but Google decided that it wanted to pursue those big opportunities. **Shreyas Doshi** (00:16:22): And in order to do that, it had to sometimes just let go of these seemingly smaller opportunities. So that tendency to think about, well, yes, there is $10 million business here, but can we make it $100 million business? Or there is a $1 million business here, can we make it a $10 million business? What does it take to make it bigger is a habit, I think, that got ingrained for me at Google. Now, of course, there's the other side of it, which is, I think, Google missed out on some trends simply because of this filter or this high bar where sometimes it's not clear if something is $100 million opportunity or $1 billion opportunity. So that is a downside of this. What I mainly took away is for instance, even at Stripe, when I joined, I was just thinking a lot bigger about the business. I was responsible for Stripe Connect and that helped us make different decisions about what to prioritize and at what pace to go after it. So, that was Google. **Shreyas Doshi** (00:17:21): Moving on to Twitter. I think at Twitter, the main thing that struck me with all the challenges, they had infrastructure challenges and also some challenges around leadership and culture is just the stickiness that comes with combining network effects with core product differentiation, because Twitter had both. We talk about network effects all the time and I don't have much more interesting things to add beyond what's already added. But this combination of core product differentiation, because if you think about it, there's still no product like Twitter, despite now being a long time since the product was launched. And that core product differentiation combined with network effects has what enabled Twitter to have the staying power it's had. And I think unless something terrible happens, I think Twitter will be around for a really long time. So, that's something I got to observe very closely when I worked at Twitter. **Shreyas Doshi** (00:18:13): And then at Stripe, I think the main thing I took away was that when you combine high energy sound judgment, low ego and small teams, you just get magic. And so, Stripe wasn't by any means flawless, but I saw that combination of high energy sound judgment, low ego and small teams more at Stripe than any other place I've been at. And so, that was very impactful and my growth and thinking as a leader. And I can go on with the founders, because I know you had asked that question. **Lenny** (00:18:45): Let's do it. **Shreyas Doshi** (00:18:46): Okay. With regards to the founders and what I learned from the founders, Yahoo, I didn't work much with the founders. At Google, I had some interactions. I was in meetings with Larry, Sergey, Eric Schmidt. And I think particularly if I were to pick one thing, I really appreciated Larry's strategic insight and particularly his ability to simulate the future to make better decisions. And so Twitter, I just overlapped very briefly with Jack's comeback as CEO back when he came back. And I think I was struck by his ability to listen and ask great questions in a few meetings that I was with him. And so, I was really impressed like he would just listen a lot more than you would expect, say, the CEO to listen. And then he would just ask one vital question and that's something I've tried to use in my leadership style ever since I saw that. **Lenny** (00:19:38): Is there an example of that or a story of that happening that you think about? **Shreyas Doshi** (00:19:42): I forget the details and they're not that important anyway. But there was a time when we were discussing a potential acquisition and I was on the fence on that acquisition, it would be something that my team would acquire, Jack was in the room. And I remember we went through as is common in many corporate settings. We went through all the pros and cons and all the intellectual arguments and the strategic arguments and the metrics arguments and all of that. And Jack was just listening through all of that. And then I remember very distinctly, he asked me one question which was something to the effect of, how does this make our users love Twitter more? Simple question. But then at that point I realized, yeah, we never really talked about that because we were so engrossed in all the other stuff. And we talked about it as a proxy because we were talking about metrics and impact and integration and those sorts of things. **Shreyas Doshi** (00:20:40): So I still remember that. I still remember him asking a simple question. Frankly at the time I did not have a good answer to that question. So that was a lesson for me to get more rigorous about my own thinking. **Lenny** (00:20:52): That's a question that a lot of PMs would hear and be like, "Oh my God. Come on, man. We're trying to move some metrics here." But I love that you took that as like, okay, I really find this really important. And this is a really important question to think about and as a lesson of how to approach this kind of stuff. So I love that. I think you were going to talk about Stripe too, right? **Shreyas Doshi** (00:21:08): Yes. Stripe, I worked a lot with Patrick and John. John was my manager for a while. And from John, I learned a lot about marketing. John is a master marketer. Among many other things that he's absolutely great at, he's just a great marketer. And I just learned a lot about how to think about talking about the product in terms that, again, obvious stuff, but talking about product in terms that customers really understand. And then sometimes emphasizing things that we as product people might not think are really important, because maybe we didn't spend much time on building it, and we want to talk about things that we spent a lot of time that are truly innovative, etc., etc. And John would often make, again, these observations about, well, if we just talked about the product in this manner, that will likely resonate a lot more with customers. **Shreyas Doshi** (00:22:00): And that got me thinking a lot about how I need to reframe my approach to basically separate the effort involved in building something with the effort you want to put behind talking about said thing. And that doesn't have to be the same features that you talk about. So, that's something I learned a lot working with John. From Patrick, I think the main thing I learned was just how to think and communicate more clearly. Patrick did that extremely well. And then overall from both, I learned the importance of setting the culture you want, simply by consistently being an example of the behaviors you want to replicate in the organization. So instead of talking about values, I saw both of them just live the values that they wanted the company to replicate, especially as the company was scaling. So, whether it's a culture of being user centric or it's a value around humility, they just lived those values so consistently. And I think that consistency spoke louder than anything that you might write on a poster on the office walls. **Lenny** (00:23:08): It's just hearing you describe all these companies and all these founders that you've worked with, it's pretty incredible to set of experiences that you've had and the primordial soup in which you became a PM. And it explains a lot about how you're able to squeeze so much wisdom and insights about the role of product management and the art and skill of product management, because you've seen so many ways of doing it and so many companies that have done in different ways. And so, it's a good segue to shifting to talk about the five big ideas. The first is around this concept of pre-mortems, this is something that stuck with me when you tweeted it. I think it was a couple years ago at this point and I see it come up occasionally in your tweets and amongst people chatting your super follower threads. And so, I also like that there's something you can actually implement and act on pretty quickly and see impact. And so, curious to hear your thoughts on this idea of pre-mortem just unpack this idea for folks. **Shreyas Doshi** (00:23:58): We're all familiar with a post-mortem or as they call it in the military, I think, after action reviews. So every company I've worked at, we've had some form of post-mortem when a launch had problems or an initiative did not go as planned or we suffered an unacceptable system downtime. Somebody would say, "Oh, we need to post-mortem that." And over the years, I really saw the effectiveness of a post-mortem. Some really great insights came out of a post-mortem about what went wrong and what we could have done better. And as I saw the effectiveness of a post-mortem, that's what made me wonder, why do we need to wait until after things go wrong? Because why can't we extract some of these insights before they go wrong? And it was around that time that I discovered the idea of a pre-mortem. I learned about it from an Harvard business review article written by Gary Cline. **Shreyas Doshi** (00:24:50): And the idea is simple, which is when you are working on an important project or initiative, you get together with your team early on in the products or the projects' life to see in advance what could go wrong. And the way I describe a pre-mortem is that if you do a pre-mortem right, you will not have to do an ugly post-mortem. You might still do a post-mortem to learn, but odds are very high that it is not going to be a bad post-mortem. And the genius of the pre-mortem ritual is the initial prompt. So it's not just about like, well, what could go wrong? The initial prompt is the genius, which is the prompt starts with, imagine this project that we are working on has failed six months from now, or this launch we are doing has miserably failed. Let's just all imagine that. Now, let's work backwards from there and ask ourselves what went wrong, what could have contributed to this utter failure. **Shreyas Doshi** (00:25:47): And that's how a pre-mortem meeting will start. The leader will start with this prompt. And then the way the meeting goes is you ask your team members to share what could have caused this utter failure, and the magic of this type of approach where you work backwards from a failed outcome. A hypothetical failed outcome is that it just somehow enables two things. One is much greater psychological safety for team members to talk about things they're concerned about, but that they were just hesitant to bring up because nobody likes to be negative in modern organizations, everybody wants to be optimistic and positive. So a pre-mortem setting gives everybody the license to actually think about what can go wrong. So, that psychological safety is a big, big factor in why a pre-mortem works. **Shreyas Doshi** (00:26:40): And what I've found is at Stripe, I did this regularly with launches that my team was involved in. Sometimes some teams or some people were just surprised or skeptical like, how is it really going to work? And then we go through the pre-mortem meeting and there's a whole process that we can talk about. But as we complete the meeting, I ask everybody, so how did that go? And just everybody is smiling, even though we've spent say 30 minutes or an hour, just talking about terrible scenarios of things that could go wrong, but everybody's feeling a little lighter because its great catharsis for them. So that becomes really important. **Shreyas Doshi** (00:27:14): And the last kind of thing I found with pre-mortems now that I've done them with various other companies as well, that I advise and whatnot is the shared vocabulary and the shared vocabulary that you get about being able to talk about things that will fail. So I have a specific approach, which is I ask the team to talk about three things. Each member on the team should bring up three things. One is a tiger. So you can bring up tigers in the shared doc that we create. And a tiger is a threat that will actually kill us, just like a tiger would. So these are actual problematic things that could be really harmful to the product or the project. So, that's a tiger. **Shreyas Doshi** (00:27:51): The other is paper tiger. So this is a seeming threat that others might be worried about, but you're not worried about. So that's the paper tiger. And then the last one, and I think this one was also used at Airbnb in other ways is elephant. And the elephant in the room that nobody is talking about. So it might not be a tiger, it won't kill us, but you're still worried that we are not seeing reality as it is that. And so, an elephant could be like, well, we are assuming that just because we launch this and do a bunch of PR that we'll get users, but are we sure we're going to get users? That's the elephant in the room that nobody is talking about that, again, this gives you that psychological safety to bring it up. **Shreyas Doshi** (00:28:28): And then what I noticed as I ran pre-mortems is that in future meetings that the team had where I wasn't even present, people started talking about, "Oh, I have this tiger. Can I bring up this tiger?" And all of a sudden it became okay for people to bring those things up, which I think is perhaps the best part about a pre-mortem is that shared vocabulary. **Lenny** (00:28:45): Such a simple idea that is clearly going to benefit you and your team. And it's interesting that people don't often do this, or haven't even thought about doing this. And so, just to get a little bit deeper, how do you actually execute this meeting? Who do you invite? What are the questions you ask? When exactly do you do this, that kind of stuff? **Shreyas Doshi** (00:29:02): And so, as I started doing pre-mortem, they got more and more popular at Stripe, other teams started doing them, and then afterwards I helped some startups also do pre-mortems. And at some point, I decided I should just write down my template for pre-mortems. So I worked with the folks at Coda to create a Coda doc, which you can find, and we can put in the show notes if possible, basically that's an entire template for how to run pre-mortems using this method that I talked about, including tigers, paper tigers, elephants, all of that. The main thing about a pre-mortem is to include people from every function that is going to be involved in, say, if you're doing a launch. And so, if it's a really large launch, sometimes I will separate it into two groups. One is everything related to the engineering side of things. Usually the engineering team is fairly large, so you can bring in every engineer. So, that's really important. Every engineer needs to be in the meeting, and so, it might be a meeting of 10, 15, 20, whatever engineers, and maybe a PM, maybe a design counterpart, and so on. **Shreyas Doshi** (00:30:07): That's just focused on the product engineering side of things like what could go wrong. And then again, for a large launch, I like doing a separate pre-mortem for the go-to-market side. And so that will involve sales team, support team, marketing team, involve design team. Some of the core engineering leads will also need to be at that meeting. Over there, we'll talk about more of the go-to-market risks. So that's what I like to do for a very large launch. **Shreyas Doshi** (00:30:35): For a smaller launch, I just like to do one meeting where everybody is present. And like I said, start with the prompt of, imagine this has failed. So as the pre-mortem meeting leader, it's my responsibility to share the prompt. And then I like doing these pre-mortems where we alternate between speaking and quiet time. So I'll share the prompt and then I'll say, okay, now the next five minutes or the next 10 minutes is quiet time where I already have that template, like the quarter doc where people start entering their own tigers and paper tigers, and elephants in a way that nobody else sees. And so, people do that, and then we go around the room and share. **Shreyas Doshi** (00:31:11): And the one other innovation I added as I did this often was also, after people shared, I ask people to pick the tiger that they find more scary, but that somebody else mentioned, so not their own tiger, but some other tiger that somebody else mentioned that they found more scary. So, that ends up being people basically are voting. And then as the pre-mortem leader, it's my responsibility to take all of that output that the team has generated in this document and then prioritize. Because again, the point is not to solve every problem, the point is to identify threats that we are not talking about openly or that we might just be missing, or we might be assuming that somebody else is going to deal with it only to find nobody was thinking about it. So then I like to create a pre-mortem action plan and then share that with the team and keep myself as the leader accountable for actually making progress on it. **Lenny** (00:32:04): Having started doing this, have you noticed a less need for post-mortems, basically projects failing less than having less problems? What impact have you seen executing on this idea? **Shreyas Doshi** (00:32:13): Absolutely, I've seen us identify certain issues that just wouldn't have come up and likely you can't really run a simulation and see what that actually looked like in real life. But those likely would have resulted in a problematic situation afterwards. A great example is sometimes you'll see a company announce something and they have massive backlash. And then one reasonable observer might say, "Well, how did this company miss this?" because what happens is they have the backlash, then the company realizes, "Oh, we have this backlash." Then they start doing damage control. They sometimes might even backtrack and undo whatever they did. They'll say, "Sorry, we didn't think about these issues. Give us some more time and we'll come back, and we'll perhaps relaunch the feature, but in a better way." **Shreyas Doshi** (00:33:00): To the casual observer, it may seem like that it should have been obvious and sometimes it's not, but oftentimes I agree, it should be obvious to these teams what issues these things are going to cause. In fact, it is obvious to some team members, but the problem is that they perhaps haven't created that psychological safety and that vocabulary to be able to talk about it in an objective way and to decide with intent, are we going to solve for this or not? So I do see a lot of those scenarios in our industry, which end up just actually wasting a lot of time. Whereas pre-mortem is a very inexpensive way to see these things because all it is is one meeting followed by some work that the leader needs to do to prioritize, followed by some mitigating actions, which you would've had to take anyway. So that's why I'm a huge fan of pre-mortems is, it's one of those very low downside, but very high upside things that I've experienced. **Lenny** (00:33:54): I'm excited to see those template, I haven't seen yet. I don't know that you put one together, so that's awesome. And we'll link it in the notes of this episode. I want to move to our second big idea, which is about something you've called LNO framework, which is all around prioritizing your finite time as a PM and as a team. And so, I'll just kind of turn that over to you to share what that's all about. **Shreyas Doshi** (00:34:15): Yes. And so, I'm going to share a short personal anecdote related to the LNO framework, which is that when I just joined Google as a relatively new PM, this is back in 2008, for the first three years, I was overwhelmed and stressed. And that was because, one, I was a new PM in this really high performance environment. I was working on some important products and launches and I just had too much to do. And I looked back at that time and it was perhaps the most stressful time of my career, where I would long hours, etc. But even at the end of the day, I'd feel highly dissatisfied because my to-do list was endless and I wasn't able to make a dent on it, and I was also a little bit of a perfectionist, so I was like, "No, no, no, I need to do this well." **Shreyas Doshi** (00:35:02): It was just constantly I would come home and talk to my wife and basically just complained to her about how I'm not able to make progress or as much progress as I want, then that was accompanied with not being able to sleep very well because I was concerned about how much output I was producing and whatnot. And so, again, very stressful time in my career. And then things changed when I discovered the ideas related to this LNO framework in a block post. Unfortunately, I can't even find that block post somewhere, but it had some ideas that I took and then created this LNO framework on myself, which is essentially that as a product manager or as anybody in a creative high impact high leverage role, all your tasks are not created equal, there are actually three type of tasks that you end up doing in such a role. **Shreyas Doshi** (00:35:56): So there are L tasks which are leverage tasks. And the L tasks are such that when you put in a certain amount of effort, you get 10X or 100X in return in terms of impact. So those are L task, leverage tasks. Then there are neutral tasks, so that's N. And those are tasks where you basically get what you put in, or just a little more than that. So you put in 1X and you get 1.1 X, those are neutral tasks. And then there are overhead tasks where, again, in terms of impact, you get back a lot less than you actually put in. And it turns out that many people who are ambitious or are perfectionists like myself by default treat each of these types of tasks the same way, and therein lies the problem. So this was the epiphany for me back at Google when I discovered some of these ideas. **Shreyas Doshi** (00:36:47): And what I realized is that among the things in my to-do list that are actually only very few L tasks, and so, it made sense for me to focus a lot on those L tasks, to take on those L tasks when I was feeling most productive, most energetic during a certain time of the day.And for the L tasks, let my inner perfectionist shine because I'm going to get so much more in return. It makes sense for me to spend that time on that PRD, for instance, related to an important feature that will meaningfully impact our revenue. I'm going to spend more time on that than I ordinarily would. So now, where does that more time come from because it cannot come from just working more hours? Well, it comes from spending less time on N tasks and O tasks. And so, there are some tasks that you do. Classic example of an O task is say an expense report. Sounds silly, but I used to try to make my expense report really good. **Shreyas Doshi** (00:37:47): And sometimes that made no sense like, "No, no, no. I need to do that." And again, this is the silliest example, but there are many examples. And something I realized is that the same type of activity can actually be either an L task or an N task or an O task. So what's an example? So say a classic PM task activity of filing a bug report. And so, many companies have these bug templates, etc., etc. that you use to file a bug report. Well, it turns out that filing a bug report depending on the situation, depending on what type of bug it is can actually be an L task high leverage task, and over there you want to file a very detailed explicit bug report. And in other cases, might actually be an O task where you don't fill out the template that diligently and you don't add 15 screenshots with annotations, instead, you just have one screenshot and you hit submit on the bug report. **Shreyas Doshi** (00:38:43): So that shift. Usually for the same type of activity, we provide the same type of engagement. The last example I'll use to illustrate this is taking notes. It turns out even taking notes, taking notes synthesizing them, and then sharing them can actually be an L task, an N task or an O task, depending on what type of notes they are. So, after I understood this, previously, I would just send all notes. I tried to make them really good, which took a lot of time. But then I realized, well, this is a meeting where, yes, I need to send notes, but again, it's like, it's just standard stuff, I just need to quickly list out. People need to really know is the three action items that came out of the meetings who owns them, that's it. **Shreyas Doshi** (00:39:23): And it is not about something highly strategic or controversial. Well, in that case, I'm just going to send the notes out the moment the meeting is over, I'm just going to hit send because I've already taken the action item. I'm not going to try to make my notes look great so that others can appreciate, "Oh, Shreyas always sends great notes." On the other hand, if it was a product review with the CEO about a very contentious topic that you have gone back and forth multiple times, and now you made a decision about something, you want to perfect those notes before you send them out, you want to get the language right, you want to be very clear on what the decision is, so there's no room for misinterpretation, so you don't backtrack afterwards or people say, "Well, but I thought we'd said this." That's a case where it's an L task. And I would say just spend an hour or even two hours perfecting those notes because it's an L task. So, hopefully that helps illustrate some of the ideas behind the LNO framework. **Lenny** (00:40:18): Yeah. And that last piece is a really good segue to the next big idea around optics and the important optics. **Shreyas Doshi** (00:41:43): Yeah. So, turns out that the L tasks, PMs implicitly just deep down they know what their L tasks are, because those are the tasks that are bothering them the most because they are not doing them or because they're not doing them as well as they know they should. So, the classic example of this is the case where a PM will say, "I know I need to work on getting our strategy right, but I don't have time because I'm busy firefighting. I'm busy just dealing with all these execution issues. And I just don't have time to work on the strategy piece." Sometimes we console ourselves by saying, "Yeah. That's because we have all these things going on this month, but trust me, next month, we're going to have ample time and I'm going to just spend a whole week working on strategy." Well, the next month rolls around and it's the same thing, you've got other issues. **Shreyas Doshi** (00:42:38): The reason we procrastinate on these tasks are, one, because we know that they're L tasks, we know the impact they'll have, and we are a little scared. That's one. The second is they require dedicated attention. And again, we are afraid about whether we'll have anything interesting to say. That's the deep fear. Why many people procrastinate on strategy? Because deep down, they don't know if they can formulate a good strategy. So time becomes a convenient excuse for us where we say, "Well, it's not me. It's just, I don't have time to work on it." And by the way, everything I say here, I have been that person. So I have been that person who's procrastinated on an L task, whether it's the strategy or whether it's writing the PRD for this really difficult feature, or it is working on aligning two teams where that alignment would create a lot of impact, but it's hard, it's an L task, but I don't do it because I don't want to deal with this other person, this manager I love to collaborate with to make it happen. **Shreyas Doshi** (00:43:46): And perhaps, I don't know if we'll get along. I don't know if I can have that tough conversation. And so again, it's an L task, but I'll try to apply bandaids instead of just tackling it head on. So, this is tough stuff. And what I've found useful there is two things, two tactics make a huge difference in helping us target L tasks better. One is the idea of placebo productivity. So, what I do is before I have to tackle an L task, that couple of days leading up to it, I do all these placebo productivity tasks. Basically, I intentionally do N tasks and O tasks. I fill up my day with N and O tasks. **Shreyas Doshi** (00:44:26): And I keep reminding myself, "Yeah, you're just doing neutral and overhead tasks." Because then that just tricks me into thinking, "Okay, if I've been doing this placebo productivity task for the last two days, now, it's the right time for me to do this L task." So that's one tactic. The other is change of location. Nothing, for me, at least fights my procrastination for L tasks better than changing the place from which I'm working. So if I normally work from this desk, the appointed day I did my couple of days of placebo productivity tasks, and on that appointed day, when I'm slated to do an L task, I will actually go out and work from somewhere else, whether it's a coffee shop or a co-working space or some other space. And I find that change of place just forces a focus and a shift in mindset that helps me bang out that L task very quickly and do it really well. **Lenny** (00:45:16): That are some great advice. There's so many layers of advice in that answer. Your point about the high leverage tasks being the task that you know you should do, but don't want to do, makes me think of a quote that I always come back to that the cave you fear contains the treasure that you seek. And I often find that to be true. And it's this reminder to just wherever the compass is pointing where it's most difficult, it's probably where the biggest opportunity lies. And so, that's a really good reminder of all that. **Shreyas Doshi** (00:45:40): So wise. Yeah, pay attention to your fears because they're telling you something. **Lenny** (00:45:44): Speaking of fears, our third big idea is around the three levels of product work. Basically the three things that a PM should be focused on and how often when you're not aligned on what is most important to you and your team, it often leads to conflict. And so, I'm excited for you to unpack this idea of these three levels of product. We can all share what they are impact, execution and optics. And when I saw this for the first time, I always come back to these three things, because it's so simple and so accurate. And so, I'm excited for you to unpack all this. **Shreyas Doshi** (00:46:12): This idea that there are three levels of product work, impact, execution, and optics. Once you understand it, it explains a lot of what you see on product teams and organizations in general. And so, perhaps start with an example that most product people, product leaders and founders are used to seeing, and something I've seen dozens of times in my career that there's a product review, say, where you as a PM are presenting to the CEO. And as you're presenting what the plan is, obviously since this is a real world product, there's going to be some compromises that you're taking. And so, the CEO perhaps asks about, "Okay, well, why is our customer service response time going to be so high in this case?" And you've thought about it, it's like you did not think about that issue, but that is a good reason why. You talk to the VP of customer support and they don't have the funding this quarter to support your product fully, which will then result in a poor customer service experience for this kind of new product that you're launching. **Shreyas Doshi** (00:47:16): But then you've agreed. You've used your skills of influence to agree that, okay, next quarter, they're going to allocate a lot more people to your product so that the customer service experience will get better next quarter. And so, the CEO asks, "Why is the customer service experience going to be poor here? Or they make a remark like that." And then you reply with all these good reasons. Again, good reasons. And needless to say the rest of the product review doesn't go as well. And after the product review, you wonder what happened. Maybe you ask your manager what happened and particularly you're wondering why couldn't the CEO see a very rational argument about why you can't do this at launch. **Lenny** (00:47:57): Never happened to me. Never happened. **Shreyas Doshi** (00:47:58): And so, it's like, why doesn't he or she see that? And the reason is that you are thinking at different levels. So you as a PM perhaps are fixated as you are dealing with this launch or this project, you are fixated on the execution level, which is what does it take to get something done? And how can I do it? How can I hit the next milestone? Those are all the things we tend to think about when we are thinking at the execution level. The CEO on the other hand is approaching it from the impact level. And particularly perhaps in this case, what is the impact to the customer experience? And often CEOs are the ones, or founders are the ones that are thinking about, what is the impact to our brand? And so the CEO is thinking at the impact level, you're thinking at the execution level, there is that mismatch. **Shreyas Doshi** (00:48:46): We litigate the minutiae of whatever issue we are discussing, but we never really recognize that it's because we are default thinking at different levels. And so, this realization helped me better understand why there were conflicts between two very smart and well intentioned people or groups within a company. I was myself guilty of this as well earlier on in my career, time and again, I noticed that we can, again, keep litigating the specific issue without understanding that, "Oh no, there's actually just a fundamental mismatch." And it's not like people are stuck at one level and can never think at a different level, it's just that we tend to default to certain levels, and that's like sometimes our preferred level. We can switch levels, but that requires a nudge sometimes. And so, that observation helped explain a lot of things, including what kind of people an organization will promote? Does it promote people who default operate at the impact level? Does it promote people more who default operate at the execution level or at the optics level? So, it has very wide ranging impacts on just overall how an organization functions. **Lenny** (00:49:59): What's an example of optics? And when optics matters, when you might not be thinking about the importance of that? Just impacting that one a little bit. **Shreyas Doshi** (00:50:06): Yes. So, optics is about creating awareness of the impact and the execution that you're doing or your team is doing. That is the most compact definition I can come up with for optics. And optics is a good thing. So I'm not saying don't think about optics whatsoever, I think it's actually important to think about optics. And now I'm talking about just internal optics. External optics is an entirely different thing and that's like marketing PR and that's definitely highly important. But even when we talk about simply we limit scope to internal optics, I'll make the observation that you should be spending some time on internal optics because it creates energy, it creates awareness, it creates excitement, it creates opportunities for feedback. Those are all really great things and they will enable greater impact and better execution for you. **Shreyas Doshi** (00:50:57): The challenge with optics is that in certain organizations that balance gets thrown off, where optics sometimes becomes the goal where somehow implicitly the organization or its culture has indicated to it's people that as long as you do the optics well, you are going to be fine, you are going to be appreciated here, you're going to be rewarded here as long as you do the optics fine. **Shreyas Doshi** (00:51:22): And it's not like the organization woke up in the morning and said, 'This is the culture we want to create." It just happens again through little actions that occur every day, it happens through who you hire, who you fire, who you promote and what kinds of things do you appreciate at all hands as the CEO or the founder. Do you appreciate a launch? Do you appreciate results? Do you appreciate, I don't know, an awesome status update that somebody sent? So a status update doesn't on its own accomplish anything. I mean, they are important, but a status update is an optics activity. Now, it is a necessary optics activity, but if you start appreciating the necessary optics activities, constantly, the signal you are sending to people is, 'Oh, you got to focus on this optics activity." So then, that becomes the goal and that can be really harmful. **Lenny** (00:52:09): So there's these three levels of product work. Do you have advice for, should I just default to one of these normally based on just as a PM, I should always be thinking about impact or is it more, just make sure you're aligned with your leader with your team? Is that the more important takeaway? **Shreyas Doshi** (00:52:23): Yes. I think that's the more important takeaway is again, it's about now we have a vocabulary that we can talk about in an objective manner without pointing fingers. It's like, 'Oh, you tend to be fixated on all these execution details and that's not the right thing." That's the type of feedback sometimes that gets shared. So now you have vocabulary to talk about this and once you have that, you can, as a team, decide what is most important given your context. I'll give you an example. For early stage teams, of course, they need to be thinking about the eventual impact, but what they should actually, I think, most early stage teams should actually optimize for execution. Assuming that they have come up with a reasonable hypothesis about what's going to win, their main emphasis needs to be on execution because you will not see impact readily on a one week horizon or a one month horizon or perhaps even on a quarterly horizon. **Shreyas Doshi** (00:53:20): So that's an example of a situation where let's be explicit, we need to get great at execution. We have a set of core insights that were informed by our desire to make an impact. But now that we are responsible for converting these insights into a product, let's be largely operating at the execution level, as an example. Say there is a platform team and that platform team has had some issues lately with availability that has disrupted some other teams within the company and their products. Perhaps that platform team should have a conversation that, 'You know what, yes, we need to focus on impact obviously to avoid this negative impact, but also let's pay some more attention to optics because we haven't been communicating with teams as much teams that rely on us. So let's create a better communication channel with them. Let's create better status updates for them," and whatnot. So again, the point is not so much like, "Oh, this is the right level and all other levels are wrong," it's about being sensitive to what's right in this situation. **Lenny** (00:54:21): So you talked about execution and how maybe for early stage startups that might be default the most important type of work to be focused on. And that's actually a really good lead way to our fourth big idea, which is a provocative tweet that you put out a while ago that you said, "The most execution problems are actually strategy problems or culture problems." And so, I'm excited to hear a little bit more about how you discovered that and what that means and maybe how to address those problems. **Shreyas Doshi** (00:54:49): And so, I realized this somewhat late in my career as a leader, most execution problems that I encounter in a high performing environment where everybody has the right intentions are actually not execution problems, they are either strategy problems or interpersonal problems or cultural problems. And so, just to illustrate it, I'll make the observation that many leaders are extremely busy in such environments, whether it's a fast growth startup or a fast growth larger company, they're extremely busy, they're usually overwhelmed. Like I said earlier, I was one of those people. Take a deeper look at what they're engaged in. And I got a chance to look at it with my peers that I was mentoring or coaching or people on my team, PMs or PM leaders were extremely busy and usually overwhelmed. **Shreyas Doshi** (00:55:36): I noticed two things, that what made them busy is two things. One is that somehow the organization had imposed very high optics requirements. So they had to do a lot of optics related work, show up at certain status meetings and blah, blah, blah. So we talked about that. So let's leave that aside. But the other reason they're so overwhelmed is that they're constantly solving execution problems. So they solve the most important ones, the new ones come up and they solve those. And then there are two new ones to solve and on and on, it's a classic guacamole. And as I noticed that, and I'll share a concrete example of where this might happen, where an execution, a seemingly execution problem surfaces, so say two teams are misaligned. They need to work together where they're misaligned. Everybody knows it. And that is affecting our execution. That misalignment is affecting our execution. It's affecting our ability to hit our OKRs, it's affecting their ability to hit their OKRs. **Shreyas Doshi** (00:56:32): So as a leader or say, you are a director of product or VP of product responsible for one of these teams, you now charge with fixing this execution problem so we can move faster. So you do a dozen meetings to figure out what's going on, you try to diagnose the issue, how to better align. And then you talk to your peers on the other side, and then you decide, "Okay, here's what we're going to do to solve this execution problem. We are going to create a new review process." And so, we are going to create this process and we are going to review priorities on a regular basis across these two teams. And then we are going to also as the managers of these individual teams to do regular one-on-ones so they can stay in sync. So this type of scenario is extremely common, again, especially in high growth organizations that want to accomplish a lot. **Shreyas Doshi** (00:57:19): You'll come up with this solution after many meetings and a lot of work, a lot of conversation. And so, as I grew as a leader, I got increasingly curious about this type of situation. And when I looked at it more closely, I started realizing that what looked like an execution problem, this misalignment and this causing execution issues wasn't usually an execution problem. Instead, it was a strategy problem in some cases, because the reason we are misaligned is because we are pursuing different strategies or that is more often the cases, the reason we are misaligned is because we don't know what the strategy is. So, we don't know what the strategy is. We craft some OKRs based on what makes sense. The OKRs are not very well aligned. We don't have a sense of priorities, and we also don't have a sense of what we do when reality changes. **Shreyas Doshi** (00:58:09): This is all stuff that a clear correct strategy should help inform. But actually this lack of strategy is what's causing this misalignment, it's not because they're not meeting regularly. And what happens in these meetings is, again, you're arguing the minutiae of like, "Well, are you going to work on this feature? I depend on this. Or can you swap two engineers from this team?" All of this stuff that PMs are very familiar with. You're talking about all the small stuff, but nobody recognizes that like, "Can we fix that?" So, as I started seeing this often was a strategy problem, sometimes it was not a strategy problem, it was a culture problem. So, what is a culture problem in this situation where two teams are misaligned? **Shreyas Doshi** (00:58:49): It's basically that you have a problem where you have set a culture that you are supposed to mainly optimize for your OKRs. In a culture like that, it becomes really hard to allow two teams to work better together because if one of the teams doesn't hit their OKRs, because they were helping rightly for the sake of the company, they were helping this other team that team's manager is going to get his or her wrist lap at the next performance review. **Shreyas Doshi** (00:59:17): So, that is a culture problem. Now, you can set up the meeting and you can request all the syncs you want between these people, it's not going to solve the culture problem, the execution problem is going to manifest in different ways a month down the road. So that's like an example of a culture problem or it could be an interpersonal problem, and this is actually quite common. It's simply that these two people cannot get along. The two team managers do not get along and they just constantly might be creating friction. And so, as a leader, it is important for you to spot that and then coach them through their differences, coach one or both of them through that so that they can better work together. When you solve that, you won't need that monthly review meeting and all these things and 50 other things, because they're not going to work anyway. So that's just one concrete example of team misalignment, which is often viewed as an execution problem, but is not an execution problem. **Lenny** (01:00:10): Are there signs that tell you where dates are slipping, people are surprised? Of execution problems that you have, are there signs that maybe it's one of these other factors? Or is your experience like it's almost always one of these other things? **Shreyas Doshi** (01:00:23): So there are some problems that are truly execution problems. So, an example of that is say you have infrastructure issues, your infrastructure is just old and it can no longer sustain all the usage that you're getting, that will cause execution problems where you'll move slower or you will have outages or high latencies or whatever the case is. That's an execution problem. Another such example of what is really an execution problem is you have a skills' gap. You have say engineers who are not particularly skilled in a certain technology or a certain type of scale that happen to be working in that area, well that is going to create execution issues or you have a PM who is more of a zero to one person, but now you made them responsible for this scale mature initiative, so that's a skill gap and that can cause execution problems. **Shreyas Doshi** (01:01:18): So, there are very concrete instances where there is a real execution problem. It's just that in high performing organizations that are growing really fast, we ignore the other factors that might be at play. And so, now what tells me if something is seemingly an execution problem but not actually an execution problem, a sure far way of identifying those is when you put on a bandaid and the bandaid falls. So, many organizations that are constantly just solving the same problem over and over again like, "Oh, we can never get along. We can never get these two teams to work together. **Shreyas Doshi** (01:01:49): This team is always slow." And so you put the bandaid, but the bandaid doesn't work. So an organizational memories tend to be surprisingly short. So we forget three months ago we put this bandaid and it's no longer working, we just approach it as, "Oh, let's create a new solution." So voila, there's a new meeting. And so that's where that honesty is important. And memory is important, that no, no, no, this is a bandaid we put, but the problem still exists. So it's probably not an execution issue. I **Lenny** (01:02:15): Love that visual of a bandaid falling off. Okay. So, this it's segue to our fifth and final big idea, maybe the most mind bending of all your ideas that I want to talk about. And it's about prioritization and you make this really interesting point that instead of thinking about the highest ROI work you should be doing, which is how I've always thought about it, how I think most PMs think about prioritization. Your point is you should think about it from a minimizing opportunity cost perspective versus an ROI perspective. And so, I'm excited to hear your take on this and where this idea came from. **Shreyas Doshi** (01:02:47): Yeah. I think I learned this by just observing Patrick at Stripe, particularly over the last couple of years that I was there. And then I encapsulated what I learned and observed in this tweet, which is when you are in a high leverage role, you should stop doing work that simply provides a positive return on investment, ROI. And you should start focusing on work that minimizes opportunity cost and what drives that is the observation that in a high leverage role, so product management is good example of a high leverage role, founders by definition are in a high leverage role, engineering leaders, design leaders, designers, these are all fairly high leverage roles. And in a high leverage role, there will be hundreds of things that you can do that will provide a positive ROI. And what is positive ROI? It's simply that the value created is greater than the value of your time that essentially will ensure positive ROI more than zero. **Shreyas Doshi** (01:03:48): So, the problem is you should not be doing most of these things. And the reason this ROI mindset is suboptimal and perhaps even harmful in high leverage roles, the formula for ROIs value created minus cost of your time divided by the cost of your time. So, the cost of your time is in the denominator. And just for the sake of simplicity, let's just call it time taken. So when the time taken to do something is in the denominator and whether it's at an individual level or at a team level, what we end up doing to get high ROI on our work is we end up trying to decrease the denominator. So when it's a ratio and you decrease the denominator, the value of the ratio grows. And so, how do you decrease the denominator in this case where time is the denominator is you start working on things that take less time. **Shreyas Doshi** (01:04:36): So you start working on the low hanging fruit. You start prioritizing the quick wins. And the quick wins are very popular. Any team meeting or sprint meeting, "Oh, that's a quick win. Yeah, let's do it." And I don't have anything against quick wins. The problem is we just fill up our plate with quick wins. And while that may be fine, in most cases, in most situations in high leverage roles, you miss the upside and you miss the opportunity that you could have gained by focusing on other things. Let's take opportunity costs now like, how do you calculate opportunity costs? Opportunity cost is simply the value of the optimal option minus the value of the chosen option. So the difference between what could have been the optimal option to pick and the option you did pick is the opportunity cost. So you need to minimize the opportunity cost, meaning you need to be working on the optimal things. **Shreyas Doshi** (01:05:27): So when we reprogram ourselves to think in terms of opportunity cost, we are no longer thinking, "Oh, is this a good use of my time?" Instead, you are thinking, "Is this the best use of my time?" And it's a subtle but profound shift in our thinking. Because when we think about opportunity cost, we will pick certain things that we would've never picked if we just had it the ROI mindset. And again, this applies equally at the level of individuals of the work we decide to do as individuals on a day-to-day basis and the work we do with our teams, the things we prioritize. So that's the basis of this statement that you should try to minimize opportunity costs and focus on those things rather than simply chasing positive ROI. **Lenny** (01:06:09): Is there an example that comes to mind when you did this or maybe did it the wrong way that helped inspire this idea? Or is this just more of a broad lesson that you've learned over time? **Shreyas Doshi** (01:06:18): Oh, I mean, I saw that all the time, the work I did at pretty much every company. And again, I've been guilty of this myself where I think typically the type of situation where I have seen this as an example is you are trying to prioritize the next quarter. There are five sure things you can do that will have small to medium impact, and it's very clear. And then there are two ambiguous things that perhaps deep down you know you should pursue them, but you don't end up picking them because it's, again, you're satisfying yourself by observing, "Oh, each of these is positive ROI. Each of these five things that we can do that are very well defined as positive ROI." And so you don't touch those two things. Now, it could be that one of those things could meaningfully change the trajectory of your business, but doing that requires more work to figure that out, to flesh it out. **Shreyas Doshi** (01:07:11): But we convince ourselves that positive ROI is great. And so we make ourselves busy and this is what I have seen myself do, I've seen other teams do. And certainly when I sit down with PMs often or even founders, I find that there is this gravitation towards these types of tasks, which are simply providing positive ROI. So it shows up most often in our planning, essentially. And again, I'm not against things that are quick wins or things that provide positive ROI, but I always want to check what are some big opportunities that we are not paying attention to by default and under what scenarios can we start chasing that. **Shreyas Doshi** (01:07:50): So when I started working on Stripe Connect, which is a major, major product for Stripe and a large business for Stripe, there was a time when I noticed when I just started working on it, I noticed the team was working on a lot of positive ROI things. And I came in and it just simply instigated that like, "Hey, how about we work on this big scary project? Because I was hearing from customers that there is some need and that the instinct that this need is going to grow over time of being able to manage marketplace payments in a more flexible way." And we wouldn't have looked at it if we were just focused on positive ROI, but as we started looking at it, we realized, "Oh yes, this is a huge opportunity." And we were able to then pursue it because we were of shifting the mindset from just positive ROI to minimizing opportunity cost. **Lenny** (01:08:35): One more question along this line, just tactically, every PM ends up with a spreadsheet of their ideas and ROI and cost and benefit and all that stuff. Do you recommend folks create a column for opportunity cost or is this more of a broad thought process you go through when you're looking through your list of ideas? **Shreyas Doshi** (01:08:51): Yeah, it's more the latter. I do not recommend trying to quantify opportunity costs because it's a lost cost. Instead, what teams need is just sometimes the freedom and sometimes just permission to explore and attack these things that minimize opportunity costs. And so, as leaders, that's the best thing we can do is to give the teams that freedom or the permission to pursue these things and the way it manifests. And the way I've tried to do it is when we are planning, I often give guidance to the team around what percentage of our time we want to spend on what type of activity. And I learned this from Google's classic 70-20-10%, where during its fast growth years, Google had the 70% search and ads, 20% apps, which was things like Gmail and whatnot, and 10% on other big bets. **Shreyas Doshi** (01:09:45): So, I have found that approach very useful during planning. Again, depends on the context, but when the team is starting to plan the next quarter or the next half or the next year, my role as a leader is hopefully I've already clarified the strategy so they have that as an input. But the other thing that I see in my role as a leader is to clarify the rough allocation. So what I'll share as a guidance with the team is given our situation and given our strategy and given what's going on in the market, I would like us to target about 60% of our time on incrementals. And by that, I mean incremental features that improve users' lives on a day-to-day basis. So these are actually high ROI things that we do, and again, these numbers are whatever they are, pick whatever is right for you, but 60% I want to go towards incrementals. 30% I want to allocate towards big new initiatives. **Shreyas Doshi** (01:10:43): And because it's 30%, it can't be five big new initiatives, it's probably one or two. And then 10% I'd like us to allocate towards stability and infrastructure. So this is the guidance I'll share with the team. And then I will ask the teams to create their plans and proposals based on this guidance. So, this gives people the space to say, "Okay, we do have this 30%, so there's no sense putting in more high ROI tasks in there or quick wins in there." And I think just the simple guidance enables the team to just do the right thing. And I often get surprised with all the awesome stuff they come back with. **Lenny** (01:11:18): I really like that rule of thumb, what an excellent nugget to include along with this big idea. I'm realizing we're going for an hour and a half now, and I don't want to suck up all your time. So there's this idea that I think it might be a really good one to end on. It'll be a bonus sixth big idea around high agency and the importance of PMs being high agency. And the reason that it stuck out to me is this, I found to be really important in my career. And I think led a lot of the success that I saw along the way is just always feeling like I have agency and feeling ownership of what I was doing and where I was going. And so, I'm curious to hear your take on this and to dive into this trade of high agency and how important that is for PMs. **Shreyas Doshi** (01:11:55): I think Eric Weinstein coined this term high agency, which once I discovered it resonated a lot and aligned with some of my ideas and the way I had defined this concept in my head for many years, that high agency is about finding a way to get what you want without waiting for conditions to be perfect or otherwise blaming the circumstances. And so, we've all seen such people, they just either push through in the face of adverse conditions or often they manage to reverse the adverse conditions to achieve their goals. And so, while this is an important trait for many areas in endeavors, I think this is particularly important for product managers because as product managers, we are constantly fighting adverse conditions, not enough resources, challenges with legacy infrastructure, staffing issues, customer problems, and on and on. There's no dirt of problems to solve as a product manager. **Shreyas Doshi** (01:12:55): And I noticed consistently over the years that as I started thinking about what differentiates the PMs who've had just a large impact and even more important than just impact to the company or to the team, PMs who've surprised me in a positive way, PMs who've really exceeded expectations, exceeded perhaps their own capabilities on paper. You see somebody's credentials on paper and then you see their work and their impact. And there's a big difference between what you might assume on paper and the impact they're achieving. And also, the reverse of that, which is sometimes you have PMs who just have tremendous potential. They look great on paper and you know when you're working with them or you're managing them that they're not achieving that potential, they're nowhere close to achieving that potential. And as I look at both of those situations, it became clear to me that high agency was a big contributor, which is the PMs in this first category were despite all the disadvantages and other things, they just took strong ownership. **Shreyas Doshi** (01:13:56): So ownership is one component. Ownership mindset is one component of high agency. They took strong ownership and then they creatively executed through the challenges. So a creative execution is another aspect of high agency and they did that with a high degree of resilience, which is a third aspect of high agency. And so, as I realized that it became very clear as to why this was happening. And then it's one of those things that once you see it, you start seeing it in people much more clearly. And so, that's when I wrote about the PM version of high agency, I think that's why it resonated with a lot of people because, again, it gave vocabulary to people for what they already understood and they had seen it, but did not have the words for. **Lenny** (01:14:38): I think that's a really good way to wrap this up, just leaving people at that point of just the empowerment, basically taking responsibility, feeling high agency resiliency. Shreyas, this has been incredibly illuminating. I suspect this is going to be helpful to a lot of product managers and even non-product managers. And so, just two last questions, where can folks find you online if they want to reach out or learn more and then how can listeners be useful to you? **Shreyas Doshi** (01:15:00): Yeah. So follow me on Twitter and just @shreyas. If you don't have a Twitter account, follow me on LinkedIn, you can just find me there Shreyas Doshi. If you really enjoy the tweets and want to see more, then you can super follow me on Twitter. So this is a smaller community that I'm really enjoying of product managers, founders, product people, designers, engineers, etc. where we go much deeper into these types of topics and more. And if you'd like to learn more about my views on various things related to product, super following me perhaps is a great way to do that. **Shreyas Doshi** (01:15:36): And in terms of other things I'm working on, I am going to be launching a course on product sense and product management later this year, so be on the lookout for that, if that's of interest. And then lastly, I think the best help I can ask for from listeners is just if any of these ideas resonated with you, share them with others. And of course, if there are questions, feel free to ask. But I think my mission here is to really help perhaps bring greater clarity on what is going on around us when we are working in teams and working on projects and products. And so, I really like it when people share the ideas, whether it's on Twitter or publicly, or even with others privately. So that is perhaps the best thing you can do, help me in my mission. **Lenny** (01:16:22): Amazing. What a beautiful way to end it. Shreyas, thank you so much for this conversation. **Shreyas Doshi** (01:16:27): Thanks, Lenny. This was a blast. Thanks for having me. It's really a privilege and I am looking forward to another conversation sometime in the future. **Lenny** (01:16:35): 10 big ideas by Shreyas Doshi coming up. I'm really excited about that, too. Thank you again. **Shreyas Doshi** (01:16:39): Great. Bye. **Lenny** (01:16:41): That was awesome. Thank you for listening. If you enjoy the chat, don't forget to subscribe to the podcast. You can also learn more at lennyspodcast.com. I'll see you in the next episode. --- ## [9/17] Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify) **Archie Abrams** (00:00:00): When you have teams naturally break up the world into different funnel stages or different points in the journey, it gets very seductive to look at my part of the funnel and what's my conversion rate through that part of the funnel, right? And then the team starts to optimize for that conversion rate as their north star. But in practice, it's actually almost always easier to just make it harder to do the thing right before your step in the funnel to increase your conversion rate. Instead of I'm trying to convert a bunch of people, I just want more people to get activated. **Archie Abrams** (00:00:32): And then once you start thinking that way, you realize actually the best way to get more people to get to a step is just get more people in the door in the first place. That will always hurt your conversion rate, but it may actually give you more people on the outside. **Lenny Rachitsky** (00:00:48): Today my guest is Archie Abrams. Archie is VP of product and head of growth at Shopify, where he leads an org of over 600 people across product, design, engineering, data ops, and growth marketing. Shopify is both an incredibly unique and also an incredibly successful business, and they do things very differently. And as a result, there's a lot that we can learn from how they approach building product and driving growth. **Lenny Rachitsky** (00:01:12): Some examples include their priorities in product roadmap are driven by a 100-year vision that comes from Tobi, the CEO. And the core product teams don't have metrics or KPIs. They're essentially banned. And instead, decisions are made based on taste, and intuition, and building towards this long-term vision. Also, the growth team optimizes for churn, which is unlike any other company I've ever come across. And once you hear why, this will make a lot of sense. **Lenny Rachitsky** (00:01:38): Also, they keep long-term holdouts for every experiment they run, and they automatically look at the impact these experiments have had on the business a year later, two years later, and three years later, and then revisit these decisions down the road. **Archie Abrams** (00:02:38): Thanks Lenny. **Lenny Rachitsky** (00:02:38): Excited to be here. Okay, so what I want to do with our time together is to basically do kind of a living archeology of how Shopify grows and what you specifically have learned about growing a company like Shopify into this just juggernaut of a business that it's turned into. To give people a little bit of a sense of just how large Shopify has gotten, so maybe surprising them about the scale of this company at this point. Could you share some stats about the scale of the business at this point? **Archie Abrams** (00:03:09): Yeah, absolutely. So overall, we're about 10% of e-commerce in the United States. So basically if you're not buying an Amazon or Walmart, you're probably buying on a Shopify-powered store. And behind the scenes globally, we did about 235 billion in GMV in 2023, which is roughly the size of the economy of Finland. So we've got a big economy and big impact happening from Shopify. **Lenny Rachitsky** (00:03:37): Wow. I think interestingly with Shopify, it's kind of this behind the scenes tool, and so I imagine many people have no idea they're using Shopify a lot of time when they're buying stuff online, and I think some of these numbers kind of creep up on people with just how large a company like Shopify has gotten. **Archie Abrams** (00:03:53): 100%. **Lenny Rachitsky** (00:03:56): **Archie Abrams** (00:06:48): The way we think about churn is really going back to Shopify as a kind of our mission and what we want to do, which is to increase the amount of entrepreneurship on the internet. And so as a business, we want to make it as easy as possible to get started with your online store, with your business. **Archie Abrams** (00:07:06): But most businesses do ultimately fail. And so the way we look at it is can we lower the barriers to getting started and get as many people in the door trying their hand at entrepreneurship? If we do that, again, many of those businesses, many of those folks will maybe on their first attempt not be as successful, but we're going to have a set of merchants who go on to become extremely big businesses, the Allbirds of the world, FIGS, etc. **Archie Abrams** (00:07:36): And the way the Shopify business model works is we do charge a subscription, but most of our revenue comes from payments, which is tied to directly to a merchant's success. So in a given cohort of merchants, a lot of people will start. Some of those people on their first attempt that's entrepreneurship might not succeed, but the folks who do go on to be successful will make that entire cohort of merchants who started something that makes Shopify as a business extremely successful. And that's why we lower the barriers to get started and help folks grow, and those winners make the whole thing work. **Lenny Rachitsky** (00:08:12): I love that. So what I'm hearing is it's not that you don't want people to stick around, it's not that you don't want people to succeed. It's that you're not optimizing every new shop for sticking around long-term. It's basically make it as easy as possible for people to try it. And all you need is a few big wins for it to all work out. **Archie Abrams** (00:08:33): Correct. And that's really a different insight than most SaaS companies that they get a customer, they really never want that person to leave. And we want to lower that barriers to get started and be successful. **Lenny Rachitsky** (00:08:44): One of the main reasons companies focus so much on churn and retention is because it costs them a lot of money to drive new customers and users. I imagine there's almost an implied it's really cheap for you all to find new customers because of maybe the brand and word of mouth. Is that true? **Archie Abrams** (00:08:59): I think that definitely has some dynamics. I think the bigger factor is the monetization model. For most SaaS companies, they're making from a subscription, right? 29 bucks a month is the only way that they're going to really monetize. Whereas our business works, you have folks who are paying a subscription. But as folks get bigger, because we're monetizing on that GMV that that merchant is producing or the revenue the merchant is producing in the form of payments and other services, it allows us to grow with the merchant in those really successful merchants, make the whole system work well. **Lenny Rachitsky** (00:09:34): Got it. So basically, your net dollar retention or network revenue retention is just absurd for the winners and it makes up for all the losers slash not losers, people that have tried to build an online- **Archie Abrams** (00:09:44): Yes, tried and haven't been very successful. When you can think of the other parallel is in angel investing, right? Most of angel investments are not going to work out, but the couple that do make that entire investment portfolio successful. **Lenny Rachitsky** (00:10:00): With retention not being the primary goal and the metric you guys focus on optimizing, how do you know if you're doing well? Is it some number of these winners have to come out every quarter, every year? How do you think about progress and achieving, and success basically for growth? **Archie Abrams** (00:10:18): This way is thinking about a cohort of users we acquire in a given time period, say a quarter. And then over the next year, two years, three years, four years, five years, how much GMV have those merchants produced in total? Not about per merchant basis, but in total, did that cohort generate GMV? And if they generate GMV, that will translate into revenue and gross profit and all of those things that we can then use to reinvest in growing the business. So it's really looking at the total value, but on that GMV basis. And GMV is a power law based metric. And so it's really that power law that drives the success of each cohort. **Archie Abrams** (00:10:56): Again, going back to investing, same thing there. Each vintage from a fund, how much did that return as a fund? And it's really driven by the few really successful outliers. **Lenny Rachitsky** (00:11:09): So this begs the question, that sounds like a very long feedback loop. And I don't know what I do with that information if five years from now, "Oh okay, that was a really good idea we did five years ago." **Archie Abrams** (00:11:18): Correct. **Lenny Rachitsky** (00:11:19): Comment on that. It touches on something you said about how metrics aren't actually a driver of how you all think at Shopify, so take that wherever you want to go. **Archie Abrams** (00:11:26): Yeah. So it's interesting. I think with Shopify, we very purposely set up different parts of the org to think on very different time horizons and with very different ways of thinking about how to build product and the like. Very different than a lot of companies that typically, have maybe one kind of unified, there's one north star that the entire company is rallying around. **Archie Abrams** (00:11:49): And so there's three major product groups at Shopify. There's core product which is basically building the 100 year, the right things for commerce 100 years from now. There's merchant services which is building things like payments, shipping, the tools that entrepreneurs need to be successful with a more shorter or medium term horizon. And then growth is really thinking about that end-to-end customer journey. How can we bring folks on and make sure they're successful? **Archie Abrams** (00:12:19): And then from a metrics standpoint, we do have obviously some leading indicators in growth that we're looking at on a given experiment or what have you. But the key in what we try to instrument in our experimentation is the ability to really look at longterm effects of experiments. **Archie Abrams** (00:12:37): So we constantly will relook at an experiment a year later, see that the way the GMV curve for the distribution was different than we might've originally thought. And that'll actually change what we do from that previous experiment. And so there's a lot of longterm monitoring of experiments over these very long time horizons to both inform what those input metrics are and more importantly hold ourselves accountable to, did we actually move what we cared about, which is that longterm GMV, in the right way? **Lenny Rachitsky** (00:13:12): Wow. Okay. I want to spend more time here. So the way you're describing it is the way the business operates is you think, what is our 100-year plan? How do we think, where does this need to be in 100 years? And with that, it allows you to run these long holdout experiments to see, is something we're doing impacting the business broadly? And because you think so longterm, you can take a year, or two, or three to see if there's an impact and then make adjustments versus I'm having to drive a certain metric every quarter, every year. **Archie Abrams** (00:13:47): Correct. And I mean on growth, we're definitely in the... We want to drive metrics on a short-term basis and we can do that obviously, but we have the luxury, and the way Tobi thinks about the world and the way we operate, to really think about these longterm effects and make sure that we're holding ourselves accountable with these longterm holdouts, and then constantly refining the input metrics that we're using and getting a lot smarter about that. But because we take that long horizon, it allows us to be better in the short term and just get a lot smarter. **Archie Abrams** (00:14:17): And a lot of counterintuitive things. And I would encourage everyone, if you can, look at some of the experiments that you thought were your biggest winners. Look at the downstream metrics for a year, two years on that experiment. And I'll bet you'd be surprised how many times the metric is different than what you thought it would be after a year. **Lenny Rachitsky** (00:14:36): Because where people just make a call at a certain point in time, here's the list in it, here's the list experience. I love this, because very few people have experiences running a longterm experiment, and so this is a really interesting insight that you're sharing that, I guess how often do you find this to be true in your long-term holdouts, where things end up being very different downstream? **Archie Abrams** (00:14:59): I think there's probably two things that have been very common. And I would say in quite a few cases, you get a lift on a metric up front, a more short-term metric. Number of people who become a paying shopper, number of people who make their first sale in Shopify. And then you look a year later, and there's actually no incremental lift on GMV from that cohort. **Archie Abrams** (00:15:21): And so I think it actually trains, a lot of us in growth are looking at these short-term metrics. A lot of the time it's actually more pull-forward effect, than you fully realize or an incremental user that's just really not worth that much. So that's one. **Archie Abrams** (00:15:35): And then two, so this effect size goes away. There are cases where the experiment has flipped the other way. And then there are cases, and these are the most interesting ones, where you realize that you uncovered a pocket of merchants that are actually extremely valuable entrepreneurs who go on to be successful, that you missed in your normal short-term measurement techniques. And so all across the board we see that. But actually the most common is it actually isn't a long-term lift from a lot of things that you might think of the short-term are. **Lenny Rachitsky** (00:16:16): Is there an example in that second bucket of what you mean when you say there's a pocket of valuable merchants? **Archie Abrams** (00:16:22): Yeah, I think a lot of this has to do with, we call it monetary friction. So one of the hardest things to do with a business is when you're getting started, is you might not have any revenue coming in, and you are kind of bootstrapping, which in Shopify's case might be 39 bucks a month. But still, it's a real expense. **Archie Abrams** (00:16:43): And so typically when you can lower the barriers to monetary friction in some form, that could be all sorts of monetary friction early. The common belief is that we'll usually get lower quality folks coming in the door, because usually discounts are associated with lower quality. **Archie Abrams** (00:17:03): If you think about in a business case, if I give you a little monetary boost and reduce that monetary friction, I can actually causally change your ability to become successful, because I've given you a little bit more time to try that idea a little bit longer. I've given you that opportunity to move your business over to Shopify. And so often in those types of experiments you see that you've basically unlocked a class of people who might've given up without reducing that monetary friction **Lenny Rachitsky** (00:17:35): Interesting. And giving them time to actually make it work. **Archie Abrams** (00:17:39): To make it work. **Lenny Rachitsky** (00:17:40): Okay. So just roughly, do you have a sense of how often you find no effect after a year that you saw early impact? Just to ballpark that. **Archie Abrams** (00:17:50): Yeah, it's in the 30 to 40% range. **Lenny Rachitsky** (00:17:51): Okay. I think you're tearing the heart out of so many growth people right now, and nobody wants to hear this that works on growth where you're saying potentially a third of the experiments they're running today that are showing lift probably don't have that same... Don't have any impact down the road. **Archie Abrams** (00:18:09): Yes. Unfortunately, I think that's brutal. Probably more common than we like to believe. **Lenny Rachitsky** (00:18:15): Yes, and nobody wants to hear this, except people that you should want to hear this because if you want to build a business that grows and need to grow, it's better to know to learn that now. **Archie Abrams** (00:18:28): Yeah. **Lenny Rachitsky** (00:18:29): Okay. So for people that can't run whole long hold that experiments, I guess is there anything that you find is a good early indicator that might be the case? Most people don't have time to sit around and wait a year or two or three. They're not thinking 100 years. **Archie Abrams** (00:18:43): I mean I think end of the day that is going to be the most effective and you actually learn the most. I think it is, though even in shorter term horizons, really being as specific as you can be about what are the early signs of success in your product, and making sure you instrument those. And then making sure, particularly up funnel experiments, you are actually looking at the further downstream metrics to make sure you have some understanding of what's moving down. **Archie Abrams** (00:19:17): So as deep as you can go in the funnel for as long as you can wait. Do that. And if you can't, you know what I would say? Still you should just bet on, if something is showing lift up funnel, still ship it and it's probably not going to hurt you, but don't overestimate the amount of impact that this is having. **Archie Abrams** (00:19:34): So it's funny, two things here is, my recommendation to folks is don't think, "Oh my goodness, I have to wait all this time." Because if you didn't move the short-term impact, you're not going to have the long-term lift. So still ship if it's short-term lift. Just be reasonable that if you can measure it longer term, you'll get better about identifying what things are that are really impactful. **Lenny Rachitsky** (00:19:57): Got it. And so it may be positive initially, but often neutral. Rarely is it neutral initially and then positive down the road? **Archie Abrams** (00:20:09): There are some cases of that, but it's rarely... I've seen neutral be positive, but I haven't seen negative. **Lenny Rachitsky** (00:20:15): Got it. Okay- **Archie Abrams** (00:20:16): That resulted positive. **Lenny Rachitsky** (00:20:17): Got it. Okay. So that's reassuring. You're not harming the business, but you're probably getting a lot more credit than you deserve as a growth team shipping things that are- **Archie Abrams** (00:20:27): Likely. **Lenny Rachitsky** (00:20:28): Likely, right? **Archie Abrams** (00:20:29): Likely. **Lenny Rachitsky** (00:20:29): And there's also just trade-offs to moving on and on balance, you're probably doing good things if you continue to ship things that are showing positive. Right? **Archie Abrams** (00:20:39): 100%. **Lenny Rachitsky** (00:20:40): Okay. This is awesome. For people that want to run long-term holdout experiments, I imagine you've built your own experimentation system internally? Yeah, we have. **Archie Abrams** (00:20:50): Yeah. **Lenny Rachitsky** (00:20:51): And is it basically you hold out 10%, say it was some percentage of users from seeing the new change? Is that how you approach it or is there a different way of approach? **Archie Abrams** (00:20:59): Two things. We have two layers of holdouts. So one is more the holdouts of every change in a quarter, holdout 5% across the board. Second is for changes that only affect new merchants, what we'll do is we'll take that group of folks, let's call it 50/50 split, and then run that for a few weeks. And then what we're doing, we look at the long-term effects is actually ship the winner to 100%, but we're looking at the cohort of folks who was assigned to the experiment. We're going back and looking at those people who were assigned a year later. **Archie Abrams** (00:21:36): So it allows us to still ship, get stuff out, but we've kind of held the experiment in a way that allows us to see those long-term effects just for the cohort that was exposed. That only works if you're doing it on new users. For existing, it's a little more complicated. That's okay. And then in our experimentation tools, all experimenters are paying that three months, six months, nine months, 12 months with here are the updated results. So you can't really get hide from, what did this really result in over a longer term horizon? **Lenny Rachitsky** (00:22:10): So your tool is email everyone that's involved with the experiment of here's what this cohort is doing now. **Archie Abrams** (00:22:16): Correct. **Lenny Rachitsky** (00:22:16): I love that. Okay, that's awesome. It's interesting that you use kind of these cohort curves for GMV, and is that the core metric you look at to see? **Archie Abrams** (00:22:25): There's a few GMV, obviously gross profit. But GMV is kind of like a key determinant of long-term success. **Lenny Rachitsky** (00:22:35): So it's interesting. Most people use cohort retention curves. You're using cohort because you don't look at retention. You're looking at for GMV over time. So that's really interesting. **Archie Abrams** (00:22:45): GMV over time, which correlates better. And there's a retention in profit. And then really the absolute number of merchants who are on the platform and then reaching certain GMV. **Lenny Rachitsky** (00:22:56): Okay, I'm going to not keep falling this path. We can go on and on. While we're in the topic of experiments and what you've done, I'm curious if there's any examples of big wins that your team has shipped that might inspire people as they're thinking about launching experiments. I know there's probably some trade secret stuff you don't want competitors to know, and I know this is particular to Shopify and a platform in eCommerce. But I guess is there anything that would be worth sharing of like, "Here's a huge win that maybe we didn't expect." **Archie Abrams** (00:23:25): Going back, there's always a lot of value in thinking through monetary friction as I mentioned. That's always going to be something to export. Trial dynamics, different types of incentives, all of those things are very impactful. **Archie Abrams** (00:23:39): I would say on things that are maybe more practical and for everyone, there's an enormous amount, and we do see these with long-term effects. But just the nuts and bolts of sign up, collecting the right information. And you usually want to collect more information than most people think you do in your sign up flow. If you can then leverage that to personalize the guidance. And this is for SaaS product, the guidance that someone can get when they onboard into Shopify. **Archie Abrams** (00:24:09): So whether you're coming on, Shopify is a very diverse product, in-person selling, online selling different channels. There's the nuts and bolts of get more information from folks, build trust in there, give them right amount of guidance when they come on in a personalized way. **Archie Abrams** (00:24:25): And that may sound like, okay, that's kind of obvious. But the amount of impact by just nailing those flows has never ceased to amaze me and setting up that person for long-term success. So monetary friction. Then just really good onboarding, personalization, a well of opportunities there. **Lenny Rachitsky** (00:24:49): I love that onboarding comes up every time I ask anyone where they've seen ongoing success and opportunities, particularly in actually surprisingly driving retention. It's interesting that that's not what you look at, but it turns out that's one of the biggest levers for increasing retention. Interesting that even for a company that doesn't look at retention, that's a big opportunity. **Archie Abrams** (00:25:07): Yes. Yeah, it's really because it's setting people up, for Shopify's case, I think the big thing about all of our metrics is... What we get very nervous about is the easiest way to increase retention is always to constrict the funnel stage one above the retention metric you're trying to optimize for. **Archie Abrams** (00:25:27): The simplest way to increase my signup to activated thing is just make it harder to sign up. Nuts and bolts, that will always happen is when you have teams on that local conversion rates, you get all these weird team incentives, because they're optimizing to basically implicitly make it harder to do the step before them. **Archie Abrams** (00:25:49): And because we focus on that long-term GMV, number of merchants who are successful, orienting every team to think about the total number of people, not the rate, but the total number of people who got to the end of their part of the journey is a very powerful way to incentivize people to do the right thing in terms of getting people set up versus do the, "I'm going to constrict the funnel step right before me to make my local conversion rate look better," which is the bane of my existence but something I see a lot of teams, implicitly or explicitly do when they get too focused on rates as a way to think about the world. **Lenny Rachitsky** (00:26:32): Incentives. What a power. **Archie Abrams** (00:26:34): Incentives, what a power, what a lever. **Lenny Rachitsky** (00:26:36): I definitely want to chat a little bit more about metrics. I know you have a really interesting take that's kind of built on what you're just talking about. But first of all, you mentioned this term monetary friction as one of the levers that you've seen success with. Can you just describe what that actually means? **Archie Abrams** (00:26:48): Totally. So things like trial, trial dynamics, trial length, trial amount. It means incentives. So what is in your product? What do people value and need in order to be successful? So in Shopify's case, that might be app score credits or things like that, but those are the two forms of monetary friction we talk about and then of course actual price point. But that's what the larger bucket of monetary friction is. **Lenny Rachitsky** (00:27:16): So let's follow this thread of metrics. You're big on absolute numbers and you've been talking about this already, versus percentages and ratios. Talk about that and how you encourage your teams to think about metrics. **Archie Abrams** (00:27:29): Yeah, I think one of the things that I think happens particularly in large, in Shopify's growth order, it's about 600 folks. When you have teams naturally break up the world into different funnel stages or different points in the journey, it gets very seductive to look at my part of the funnel, and what's my conversion rate through that part of the funnel? And then the team starts to optimize for that conversion rate as their north star over a longer time period. I'm going to try to move my conversion rate from 10 to 12% or what have you. **Archie Abrams** (00:28:04): But in practice, I talked about it's actually almost always easier to just make it harder to do the thing right before your step in the funnel to increase your conversion rate. If I make it harder to sign up, it's going to be very easy to increase sign up to activated rate, because I just have fewer people and the people who made it through our higher intent. **Archie Abrams** (00:28:23): And so I see teams get really stuck when they are trying to optimize conversion rate, but they just make it harder to do the previous thing. Versus everyone is thinking about absolute number of people who made it through their "stage" of the funnel. So instead of I'm trying to convert a bunch of people, a conversion rate, I just want more people to get activated. **Archie Abrams** (00:28:48): And then once you start thinking that way, you realize actually the best way to get more people to get to a step sometimes, and often they just get more people in the door in the first place. So make it easier to sign up or reduce friction. It's the opposite. **Archie Abrams** (00:29:05): Because that will always hurt your conversion rate, but it may actually give you more people on the outside. And a lot of teams get very nervous, their retention rate went down, their LTV went down. Oh my goodness, is this this going to affect our ability to pay? No, your CAC also went down by probably more. And so now you have the ability to likely spend more and you have more people through the door, getting to each point in the activation or the immersion journeys. **Lenny Rachitsky** (00:29:33): What I'm hearing is essentially teams are gold not on increase, lift this conversion step by some percentage. It's drive some absolute number of new merchants, potentially. **Archie Abrams** (00:29:45): Merchants, yeah. Exactly. **Lenny Rachitsky** (00:29:47): This is a good segue to I want to hear how you structure your growth team at Shopify. Essentially, what's the raw structure, what are the different teams, and what do they focus on? And then what are the functions within each teams? **Archie Abrams** (00:29:59): We have two big groups within growth. So one is what we call growth R&D. So this might be what you traditionally consider product design engineering, data, your traditional product teams. Then we have growth marketing, which in Shopify's case is paid acquisition, media buying, affiliate marketing, email, content, and SEO. So that's growth R&D, growth marketing. **Archie Abrams** (00:30:23): Within growth R&D, three pillars. One is what we call growth products. And so this is basically everything from landing pages, sign up, onboarding, monetization. So trial, incentives, the like, all the way through to what we call our home feed, our engagement to basically get more merchants. Again, not necessarily to retain, but to keep giving entrepreneurship a try to become bigger and bigger businesses. So that's growth product, the full life cycle there. **Archie Abrams** (00:30:56): Second is what we call our enable pillar, and this pillar is building tools for both growth and the rest of Shopify. So things like experimentation platform, our communication platform, our business intelligence tooling that powers a lot of what we're doing, our more tech work to support our growth marketing team. **Archie Abrams** (00:31:14): And then our third bucket, which is maybe a little different from most growth teams is actually our customer support, groups within growth. We want to think about customer support as part of this merchant journey of coming on, giving entrepreneurship a try, all the way through to here's the support I need as I'm becoming a multi-billion dollar business on Shopify. So those are the three big growth product buckets. And then within growth marketing, it's a more traditional channel setup. Paid, all the different channels online, offline, SEO, email, and affiliates. **Lenny Rachitsky** (00:31:49): Super cool. Okay. So within growth RD, I just took notes. I'm going to summarize what you just shared, which is awesome. So there's three big buckets. One is growth product, which essentially is onboarding. It feels like it's like the top of funnel, get people in. Well okay, so growth marketing feels like that's super top of funnel bring- **Archie Abrams** (00:32:07): That's super top funnel. **Lenny Rachitsky** (00:32:08): Yeah. Okay, got it. So growth marketing, drive people to Shopify.com. Then within RD team, growth product takes that user and tries to get them to activate it. Enable helps... It feels like that's like internal tooling and ways to make the teams internally more efficient. **Archie Abrams** (00:32:27): Correct. Both growth and outside growth. **Lenny Rachitsky** (00:32:29): Awesome. Okay. And then the customer support team, that's really interesting. So there's a customer support product team that helps new merchants be successful. And does that include actual customer support agents? Is that within that team? **Archie Abrams** (00:32:46): That's not. We build a tooling to make those support advisors superheroes. And then on the help center, all of our AI stuff to make a great customer experience for people who are just engaging in a self-serve. So it's the tooling and the experience for merchants. **Lenny Rachitsky** (00:33:03): Okay. So with these teams, is there anything you can share about just how you think about metrics/goals for these different buckets? We don't need to get too deeply, but does everyone basically have an absolute new merchants goal or is it a little different? **Archie Abrams** (00:33:18): So yeah. So at the highest level we think about that total cohort value. We bring in a set of merchants in a given year. How much GMV, how much that set of merchants worth over the next three, four years to Shopify? And that's the most important thing that we want to focus on. And then that of course, from an efficiency standpoint, that of course meeting our payback guardrails and all of that. So that's the macro growth perspective. Cohort value over cost and payback. So that's the macro point of view. **Archie Abrams** (00:33:52): And then within growth marketing, each channel operates with certain guardrails around their LTV CACs. Same thing for content and SEO. That operates with kind of a guardrail model for each piece of content. How much is that going to come back and down the line? **Archie Abrams** (00:34:09): For growth products, it's also a combination of total GP incremental cohort value that's produced from those teams. So everything is basically going to be measured on from an experiment, ideally measured over a very long time period. What was the incremental cohort value lift that this generated? And that's how we think about and measure the impact of each of those sub teams along the way. **Archie Abrams** (00:34:40): Each of those have a civic part of the funnel they play with. But because they're measured on absolutes and they really think about that absolute value, we don't get caught into, did your conversion rate over the course of this year go up or down? It's kind of irrelevant. What was the sum of the impact over a long period on that total cohort value that we're trying to produce from before merchants? **Lenny Rachitsky** (00:35:01): And the way you come up with this goal I imagine is you have a forecast of where things would go organically, and then here's the lift we want to see from the work this team does this quarter, this year. **Archie Abrams** (00:35:12): Correct. And then we're going to measure against for each experiment, did it actually get to where we expect that lift to be? **Lenny Rachitsky** (00:35:21): And those experiments again, are those all long-term holdout experiments where you look wait a year or some- **Archie Abrams** (00:35:29): We call. We call the experiment after three weeks, but in all cases, the group is held, we watch them. And that's where that ping comes back, every experiment is watched. And that ping comes back three, six months, 12 months to re-look at was this actually successful? **Lenny Rachitsky** (00:35:42): Okay, cool. **Archie Abrams** (00:35:44): So that creates the loop of shipping value quickly, but making sure we're holding ourselves accountable to did this actually produce results over a long period, or did it actually just have this neutral effect? It's like, oh, then we can learn from that and get better. **Lenny Rachitsky** (00:36:01): **Archie Abrams** (00:37:38): 30. Yeah. **Lenny Rachitsky** (00:37:39): Yeah. Okay, so it's still roughly, yeah. **Archie Abrams** (00:37:42): And it's great learning and that's why we take it. It's like, wow, okay, now we really uncovered something and it's such a successful discovery. Wow, okay, we thought this thing. But now we learned it actually wasn't as true as we thought. Cool. What can we take from that and be smarter next time so we don't just double down on the wrong things? **Lenny Rachitsky** (00:38:02): That's so interesting. And again, and you mentioned most of the reason this is the case when something doesn't show lift down the road is it's pulling forward success that would've been seen later on its own if you had not even shipped this thing? **Archie Abrams** (00:38:14): Correct. **Lenny Rachitsky** (00:38:14): Awesome. Is there an example by any chance that comes to mind of something like that that's just like, "Wow, that was a big win. And then oh I see we just pulled forward some revenue from the future." **Archie Abrams** (00:38:25): So I think one good example is something around payment failure notifications. So one of the things that a lot of teams have or see is we call Dunning effects where somebody might have a payment not go through, a credit card that doesn't go through. So we did a bunch of experimentation around, hey, how can we alert people that their credit card is failed, their payment attempt failed? **Archie Abrams** (00:38:47): And that's a typical growth win, usually produces a lot of short-term impact. And that's what we saw here. We were doing much better alerting, reminding people, sending them a million emails about it. Cool, we got some pretty major lift. **Archie Abrams** (00:38:59): You look back six, 12 months. There was really no long-term lift. And why is that? Because there's really a little bit of a selection bias there that people who were letting that payment fail probably weren't actually that dedicated to this entrepreneurship craft. They may have updated their credit card, but they still really weren't in it. **Archie Abrams** (00:39:22): And so that was a good example of in a bunch of this stuff around payments, even "preventing" churn where you look, it's six, 12, 18 months. On a GMV metric, not a lot of lift over that long-term horizon. **Lenny Rachitsky** (00:39:37): I love this example. I could see so many people having run experiments like this and like, "Oh, we found such a huge win. This team's killing it. What a great idea. Of course this makes sense," and then turns out it's nothing long term. **Archie Abrams** (00:39:54): Which is great. We were going to spend a lot of time, okay, what else can we do here? It's like, no actually bigger fish to fry in a lot of other areas. So it helps the team just feel really good that their work is really the things that were good. **Archie Abrams** (00:40:13): Another one that went the other way, which was really interesting was in our online store, and this might be if you use Shopify, we have sections and blocks that come pre-configured. And so we tested, okay, if we give you a pre-configured block of you should have an image up top, then a text banner, and then a collage with your products. That should help folks understand what to do when they're building the online store. It actually had no lift in people converting to a paying merchant. **Archie Abrams** (00:40:48): However, when we looked longer term on that six months later, it had a pretty massive impact on the number of people who were selling and producing GMV. And why is that? Because it didn't likely really influence anyone to buy Shopify or pay for Shopify. But the people who used it created better stores that were higher converting, and so they got early sales. They actually converted one of their visitors and they got momentum, and they stuck with entrepreneurship a little bit longer. And we saw that in that opposite way. **Archie Abrams** (00:41:21): And so this is an example where that neutral, and so we tend to ship neutral. It's like it could be positive and so let's let it go if we have good intuition about it and it'll turn. So we've seen a bunch of these things go in very different directions. **Lenny Rachitsky** (00:41:36): This is so fascinating. I didn't realize that you ship neutral experiments. That's an interesting insight. So it's like if you feel good about it and it's neutral, you ship it? **Archie Abrams** (00:41:45): In our culture of the kind of aim heavy, if the intuition is right that this probably is helping merchants, why do we start with that the original control is better if it's neutral? Let's start with, what would we have shipped if we were a blank slate? And if it's neutral, actually neither is better, so let's just pick the one we feel better about and ship that. **Lenny Rachitsky** (00:42:03): Makes so much sense. Oh man. Okay, so let's talk about this a little bit more. So this aim heavy concept, this idea of thinking 100 years out, can you just share more about that insight and that philosophy? I know it sounds like it comes from Tobi of how he likes to think about the business. **Archie Abrams** (00:42:18): Totally. It is all Tobi of really making sure Shopify is so oriented around, we are here to build 100 year company. And so the decisions we're going to make are really oriented towards the long-term success of merchants, of Shopify. Embedded in all of our principles are make the best product in the world, make money to do more of one. Never reverse principles two and three. In every kind of executive meeting, every town hall, that slide comes up. It's like you've been at Shopify, you've probably seen that slide 10,000 times. But it's an important reminder job is to build the best product for merchants over the long period of time. And then all of the metrics and the make money part of it, secondary to that. So what we care about is that long term piece. It ties a little bit to that original conversation about entrepreneurs and being the core of why we just want more people to start businesses and go. **Archie Abrams** (00:43:15): It's very seductive I think in most companies, including in Shopify because we can support large enterprise businesses today, right? Big brands who want to get off an outdated solution and come over to Shopify. It's very easy to just say, "Oh, that's very concrete." There's an existing business, we want to have them come join Shopify. **Archie Abrams** (00:43:40): And in the short term it feels really good. It brings a lot of revenue right away. But if you're thinking about the long-term 100 years from now, guess what? All of the big brands of today be out of business. And many of them will be out of business in 30, 40, 50 years. The real success of Shopify is getting every business to start with us and go, but making that type of an investment and being so focused on that entrepreneur segment and making it easier is how we build a very, very long-term oriented company. So just even how we do capital investment, how we do product decision-making comes back to, hey, we can't chase the short-term. Even more concrete things. **Lenny Rachitsky** (00:44:24): Is there an example that comes to mind where you did that where something short-term looked like, "We should definitely do this," but we're thinking thinking 100 years out so we're going to approach it this way? **Archie Abrams** (00:44:35): It's kind of very much just imbued in the culture. Almost everything kind of feels that way. And I'll give, practically speaking, every six weeks all the R&D group leads we get together and we sit with Tobi and each other and review every single project across the company. Every six weeks, every single R&D pull up the dashboard, and look at it. **Archie Abrams** (00:44:56): And in that conversation, so much of the conversation is about both the technical how. How are we building this in a way that allows for Shopify to have optionality in the technical decisions that we are making? And I think for Tobi, one of the things I've learned and so is that how, the technical architecture determines strategy in a technology company even more than the what and who we're building for. If you build the right technical how and set yourself up to have a platform that can be adaptable, flexible, that is incredibly valuable over the long term. It means we will sometimes take longer to ship a feature. It means we'll not chase certain deals or what have you, but we're going to kind of make that investment. And it comes through in all of our reviews and just how we got to do our work together. **Lenny Rachitsky** (00:45:53): Wow, that is really unique. I've not heard of that where how... Usually it's the opposite. Let's not worry about how we're going to build this thing. It's why are we building this thing and then when are we building it? And not just the architecture is the most important thing. **Archie Abrams** (00:46:09): Yeah, I mean in the last one, it was great. We had a 30-minute discussion about how to build CSV importers for people coming over from different platforms, and it was all about are we using open source library, doing it internally, are we doing it in the core code base? Are we building a separate first party app to do it? It was incredible detail. **Archie Abrams** (00:46:29): This is what's amazing about Tobi. The technical detail of how we're going to do this was incredibly important to get right, to kind of set up this type of infrastructure. And most companies it'd be okay what, you're going to make it easier for people to migrate their data over. Cool. Team, go figure out how. And if team does figure out the how do we work on it with Tobi and the details, because the how is so important to how we build for the future. **Lenny Rachitsky** (00:46:54): That's fascinating. And usually it's how do we do this as quick as possible, because CVS importing is not our core differentiator. It'll just build something good enough, we'll ship it, we'll move on. **Archie Abrams** (00:47:02): Correct. **Lenny Rachitsky** (00:47:02): Totally the opposite. That is fascinating. What's also really interesting about this is I think about Brian Chesky at Airbnb where I worked for a while and his... So one, he also had this idea of the 100-year vision and thinking for the future way out in 100 years. But interestingly, since he's a designer, he had a very different focus. So Tobi, he was an engineer. He still codes from what I can see on Twitter, he still- **Archie Abrams** (00:47:24): Absolutely. **Lenny Rachitsky** (00:47:26): So I could see why his brain goes there and why he's really strong in the how. Brian on the other hand is very focused on the experience and making sure the design is amazing, and the app is exactly what he wants it to feel like. It is very experience oriented. So it's interesting that these founders lean into the thing that they're strong at, and understand deeply, and that ideally connects with the way this business specifically wins and grows. And it makes sense a platform, I could see why engineering would be so essential to get right. Travel, hospitality, consumer app. I could see why design is so important. **Archie Abrams** (00:48:03): 100%. **Lenny Rachitsky** (00:48:04): Fascinating. One more tidbit that I've heard about how you all think about this is metrics. And you mentioned before we started recording that a lot of the company doesn't actually have metrics that drive what they build, especially within the core business, which I think surprised a lot of people. Most people are like, "Every team needs a metric and a KPI, and this is how we measure progress and this is how we know if they're doing well." Talk about just how that works, how most of the companies doesn't have a metric. **Archie Abrams** (00:48:31): Yeah. It's funny, we ran against KPIs are basically banned as OKRs or banned and all that. And so certainly, in growth you have metrics, but they take a different form. And then in core, it truly is, do we have conviction that this is the right technical foundation to build the future of commerce? And that is built through certainly looking at data. So it's not that teams are not looking at data and using it as a piece of their puzzle, but it's not the overriding. And when we go to ship a feature in core, it's not like a team is held accountable for this metric over this six months. It's much more, did we ship the right thing? And we're going to kind of get at that through a variety of lenses. Could be some of that could be data, qualitative, just our own product sense of what's good or not. **Archie Abrams** (00:49:24): And so I think the upside of that is I think we tend to ship things in core and that are incredibly forward-facing and we take more risk. I think to acknowledge some of the downside of it though is sometimes conversations get extremely subjective about what is the right thing to do. And so that requires the right way of having good discussions, openness from all leaders and from teams to debate those things. But it does result in some squishiness, which again has its pros and cons, but taste is what drives a lot of what we're shipping in core. **Lenny Rachitsky** (00:50:05): Yeah, I'm glad you touched on that. I was going to say, okay, everyone would love this idea of just build things that we think are awesome. It's going to be great. But then you build a whole org with teams and people building stuff. How does one know if they're building things that are good and helping versus not? **Lenny Rachitsky** (00:50:21): And you're pointing out there are pros and cons to that. The pros is we're not optimizing for some short-term wins and driving some poor metric. The con is you might ship stuff that... There's a lot of subjectivity, and people may not agree, and it's a lot of squishy stuff. **Archie Abrams** (00:50:39): Yeah, totally. Glen, who's heads of core product, I mean one of the things that's so impressive about Glen and that core team is they go incredibly deep into every single release that is shipped. And so you do have a central eye on the quality and how it all fits together. **Archie Abrams** (00:51:00): And so that I think helps make sure there's a consistent kind of bar for taste. A bunch of folks Tobi obviously that can enforce that. So it's subjective, but it's objective in the sense that it's kind of a small number of people who really hold what that bar is and needs to be. I think if it's just subjective, let's just ship what we want without a couple people really holding that quality and that taste bar, that's where things go really sideways. **Lenny Rachitsky** (00:51:31): Awesome. That's exactly what I was going to ask is, who's the ultimate decider of taste and what is good? And so it sounds like basically Tobi above, and then he's kind of deputized Glen and relies on him to make a lot of these final calls. And then I imagine Glen has some folks that he kind of deputizes to make smaller decisions along the way. Or not, or he's very involved in everything. **Archie Abrams** (00:51:55): And I think this is the fun thing about Shopify. Literally we have our own internal project management system that's been kind of crafted just for Shopify and every shift- **Lenny Rachitsky** (00:52:03): What is that called by the way? It's got a cool name, right? **Archie Abrams** (00:52:06): GSD. **Lenny Rachitsky** (00:52:07): GSD, yeah. [inaudible 00:52:10]. **Archie Abrams** (00:52:10): Yeah, get it done. **Lenny Rachitsky** (00:52:11): That's what I remember. **Archie Abrams** (00:52:12): So get shit done. And every project, so you got a core project, you have emergency service, you got growth project. And the expectation is that the group leads. Every single project that goes out has a few minute video with Figmas and everything, and everything that shipped. Needs to be okay-toed, so approved by the group lead. There's nothing that can ship without that okay-to approval. And that okay-to approval has to be Glen, Carl, myself with different groups. And so that is how everything is reviewed. Now of course there's great amazing teams that do amazing work, but it is that that's how the system works. **Lenny Rachitsky** (00:52:50): And okay-to specifically means someone above reviews it or all this whole team, everyone looks at it? **Archie Abrams** (00:52:56): No. So Glen reviews the core stuff. Carl reviews the MS. Okay-to. It's interesting. **Lenny Rachitsky** (00:53:05): It's basically Glen is founder mode and not as a founder where he's involved in all the details, has final say. So this is a really cool example of founder mode, but not as a founder. **Archie Abrams** (00:53:15): Correct. **Lenny Rachitsky** (00:53:16): In the way you guys operate. And I imagine sometimes Tobi disagrees with Glen and then they talk about it and things get ironed out. **Archie Abrams** (00:53:22): Totally. And that's why we come together every six weeks, everyone in person to review every project so we can hash out those disagreements. Go through all the core projects, all the merge service projects, all the growth projects. And it's a great forum to say, "Hey, here's where we disagree," really on the how and the tactics of what's happening. And we can flag those things, have good debates about whether there might be misalignment. **Lenny Rachitsky** (00:53:43): Amazing. What a unique way of working. I'm so fascinated by all this. So what I'm hearing essentially within Core, Glen and his team come up with, "Here's what we're going to build the next quarter." You guys have twice a year releases, is that right? Or is it every season? **Archie Abrams** (00:53:58): Yeah, so big additions. Twice a year. Obviously continually shipping, but we package them twice a year in a big bang. **Lenny Rachitsky** (00:54:05): Big launch. Yep, I've seen those. Okay. So he's like, "Here's what we're going to do in the next release. We're just going to build this because we think this is right. And we're not driving a specific goal. We're building for 100 years in the future. Let's just build it." And basically you build it. He's like, "This is great, not great, iterate until it's this good," and then ship. And great. Okay, this is great. Okay, so then there's that team, and then there's your team, which is drive some freaking numbers, drive growth, hit these goals. How do you collaborate across these two teams? Do you have a model for how you work together? Because these feel like very different ways of working? **Archie Abrams** (00:54:41): Yeah, honestly, it's been one of the things I'm very proud of. We built a really great partnership for the last three and a half years, because it's intentionally meant to be almost at odds, and that's part of the structure of how we want to work. **Archie Abrams** (00:54:56): But it comes from, I think, a place of respect on both sides. And I'd say for anyone, it's okay, here's what growth is going to do. We're going to do it in a way that is high quality, that is shipping really good stuff for merchants. We're probably going to approach it in a faster way. We might disagree on things, but we're going to have reasonable paths to handle that conflict. **Archie Abrams** (00:55:17): And so while there's no magic bullet, it wasn't like these are the surfaces that growth can touch, these are not. It was like you can go anywhere in the product, but let's go figure out how to work together to figure out that quality bar to understand when you're going to be different on it, on the quality bar to get something out to learn, and just building trust along the way that we're actually going to ship high quality things and we ship it to 100% and move. And so a lot of great work on the team to make those relationships really strong. **Lenny Rachitsky** (00:55:47): Got it. So basically, you guys are like, "Moving this button over here is going to drive so much growth," and then Glen's like, "No, this is not acceptable. We don't want a button here. This looks terrible. Everyone's going to hate it." So that's the healthy tension. I'm describing a combative- **Archie Abrams** (00:56:01): [inaudible 00:56:01] totally. And it's like, okay, so how are we going to work to figure this out? It might be, "Hey, we're going to move the button. Hey let's run the test," but see the short-term lift. You know we're going to monitor it long term. You know when we ship it, it's going to be high quality, high quality polish. And you trust us to make those trade-offs. **Archie Abrams** (00:56:19): I wish I had a better answer of it's very human. It's very that trust that's that's very important in any of these. I think growth with other teams is like, there's no replacement for just the human trust and then following through on commitments of no, we are actually going to make this thing really good. **Lenny Rachitsky** (00:56:38): Is there an example of that, that comes to mind where you had something that was you thought was going to drive meaningful growth? You showed it to Glenn, he is like, "No, don't know about this." And then either you iterated or you just forget it, this isn't right for the platform even though it's going to drive some meaningful growth? **Archie Abrams** (00:56:54): The place that we often come back to is, and this is with I think Tobi is great, Tobi and Glen, is on wizards. So wizards- **Lenny Rachitsky** (00:57:07): Onboarding carousels. **Archie Abrams** (00:57:08): Onboarding carousels. Some way that basically has folks get set up by not using the actual product. And so we've always kind of danced around and we have very specific no wizard principle, but I think that sometimes the tension is wizards can serve a purpose in certain circumstances, but we've avoided doing that. But we've always worked to try to make the principles of what a wizard does really well, which is it simplifies the product into something that allows people to have a lower bar, to try to work with core to bring that into the actual experience itself. **Archie Abrams** (00:57:52): So the example of that experiment I mentioned to you of giving pre-filled sections in the online store editor, you could have solved that in a wizardy way of, "Enter a few things, and we're going to generate these sections for you." Instead, we actually took those pre-generated things based on what we know about you and put it into the actual project experience itself. **Archie Abrams** (00:58:15): So it tried to get at some of the principles of what a wizard can do well without avoiding the wizard principle, without creating actual wizard. So that's been some of the, how do we work together to get the intent of what the growth ideas but in a way that's consistent with the way we want to build in core? **Lenny Rachitsky** (00:58:34): Got it. And I get why that you think about this a lot because you talked about one of the biggest levers is onboarding and helping more people get activated, and so I could see why you spent a lot of time thinking about how do we help more people succeed there. **Archie Abrams** (00:58:46): Yes. **Lenny Rachitsky** (00:58:48): I want to ask your insight on this idea that people might be listening to this and feeling like, "Oh, we need to build a team that just builds great product and is not constrained by metrics and driving growth." Short-term thinking, long-term thinking, 100 years. This is inspiring I think to a lot of companies because the sounds great. **Lenny Rachitsky** (00:59:08): What do you think it takes to make something like that work? Because in a bad case, this team just sits around and builds whatever they want, and the rest of the company's like, "God damn, this sucks. I have to show success in metrics and moving a metric in this team, over there just build beautiful things." Is it like you need a founder like Tobi, that prioritizes this and values it and has a very good taste and intuition? What do you think are important elements of something like that, of this approach working at a company based on what you've seen? **Archie Abrams** (00:59:37): Yeah, I think it needs to have a very opinionated founder set of people who are driving what good looks like. And I think Shopify a few years ago and before maybe sometimes drifted into the mode of, "We are just going to build stuff and each kind of team is just going to build stuff not really accountable for it," and that is a very, very bad state to end up. So I think you either have to use, my sense is metrics as accountability, which is the most common kind of way to drive accountability and focus. Or extremely strong founder or set of folks who have extremely strong opinions on what good is and what taste is. If you have one of those two, you can make it work, but the worst case is let's just go build a bunch of cool stuff in kind of a haphazard way. That I don't think would work. **Lenny Rachitsky** (01:00:30): Yeah, this is great. So either you need metrics to tell you you're doing the right thing or really correct and good taste in your founder. **Archie Abrams** (01:00:42): Correct. **Lenny Rachitsky** (01:00:42): Cool. I think that's a really good way of... And I imagine every founder is going to think, "Oh, that's me. I have this, I can do this." I think it's rare in real life. It's rare that you're like a Tobi, or Brian Chesky, or Elon. **Archie Abrams** (01:00:43): 100%. **Lenny Rachitsky** (01:00:57): Yeah. It's hard to internalize that, but I think that's the reality. So most people will be more successful building things that are driving metrics they can track in an experiment. **Archie Abrams** (01:01:07): Yes. **Lenny Rachitsky** (01:01:08): Awesome. This is very fascinating. I'm so happy we're spending so much time on this. Okay, there's a few other random things I'm going to touch on. One is sales. So historically, Shopify has been very product-like growth, very organic. Go check it out, sign up, shop a store, start a store, grow. And you guys have layered on sales. In a sales motion that's an increasing part of your business. What have you learned about your team, the growth team working with sales and making that a successful relationship? **Archie Abrams** (01:01:36): Yeah, no, it has been great over the last couple of years as built out, the sales order has added a whole new kind of motion to Shopify. As Shopify's product got better, it can serve the biggest companies in the world. It's like the natural evolution. Well what are you going to do that for people to grow up on Shopify and to be the biggest companies, but we're also going to take folks another platform, bring them over. **Archie Abrams** (01:01:57): For growth in sales, I think the biggest learning from the the R&D side at least has been the scale is very different with sales, and so it's really hard to use as much quantitative data to make growth, to make some of those decisions. **Archie Abrams** (01:02:18): And so a lot of it has been building much more qualitative insights working with merchant success, sales about the challenges they're facing and onboarding a large customer. So how do we build import tools that work for them? How do we make sure they have the right guidance in the product for a very different set of use cases? So a lot of it has just been very much empathy building with sales about what that merchant journey looks like, and quite frankly challenging ourselves to think differently. It's been one thing. **Archie Abrams** (01:02:49): And then second, we kind of built two very distinct funnels for a little bit. There's a sales funnel. You come in, you contact us, that's it. There's no mention of self-service, there's no this. There's just drive MQLs, boom. Then there's the self-service thing. There's no mention of sales anywhere. **Archie Abrams** (01:03:05): So one of the last thing the year, last year we've been really doing is how do we create these hyper journeys where there is... We shouldn't force the merchant to choose, do you want to talk to sales? You want to do self-service? Should give them the options, whatever path that they want to go on. **Archie Abrams** (01:03:19): And so a lot of that has been building into the self-service journey over to sales and then from sales into self-service. That's broken a lot of metrics in the business. That's broken a lot of ways people have thought about their jobs, and so there's been a lot of cultural resetting and just getting smarter from a metric standpoint about, how do we measure this thing of hybrid journey? They came in via self-service, they went over to sales. How do we value each of those components in the process? And transparently, that's something we're still getting better at, but it's really important to get there. **Lenny Rachitsky** (01:03:55): Is there an example of something that broke that would be illustrative of what you're describing? **Archie Abrams** (01:04:01): Yeah. So I think that breaks is drive someone from an ad over to self-service. We typically look at only the self-service LTV of that person. But what happens if they come in, they sign up via self-service and then they go talk to sales? They get changed to a sales driven merchant, which means that that value of that merchant, which is usually actually quite large, does not get associated back to that ad campaign. Oh, guess what that means? That means you would probably reduce investment on that ad campaign because you weren't valuing that. Our system had two different models for calculating LTV. Sales driven one, and a self-service one. Uh oh, we're going to make suboptimal investment decisions now by kind of moving things around even though it's the right thing to do. **Archie Abrams** (01:04:55): So a lot of it's in rebuilding all instrumentation, how we do LTV modeling, how we do attribution, how we do incrementality testing across each of those different types of outcomes, because it was not an intuitive thing for us originally because we had built all of these systems with a much more siloed view. **Lenny Rachitsky** (01:05:16): Yeah, basically attribution gets a lot more complicated. Are you going in a multi-touch attribution direction or is there something even more clever? **Archie Abrams** (01:05:26): My rant is I am... Multi-touch attribution as its place. I think ideally what we want to get through is what we really care about is incrementality. So incrementality is kind of the gold standards, for people who are less like attribution measure is, how do you assign value to a given touch point, right? Click, a view, etc. But it doesn't tell you causally what drove something. That's where incrementality tells you. Incrementality test is basically don't show ads on meta for certain number of people. Show it to the other set, see what the lift is and the outcome. **Archie Abrams** (01:06:04): A lot of what we're doing is trying to get a lot, is continuing to get even more sophisticated in incrementality measurement for not just self-serve outcomes, but for self-service outcomes that then drive to sales for sales specific outcomes. And as soon as we have that kind of incrementality at the channel level, we can get a lot more sophisticated in terms of our bidding, budgeting, and all of that. But that's really the key thing we want to get to. **Lenny Rachitsky** (01:06:35): There's certain topics that alone can be their own podcast conversation to just dive deep into this stuff. But I'm going to stop myself and I'll go further down that track. Let me touch on a couple more things before I let you go. **Lenny Rachitsky** (01:06:46): One is marketing. So we talked about sales, marketing. You guys don't have a CMO, there's no Shopify CMO. Instead you embed marketing leads within the org. For folks that are trying to grapple with that, should we hire CMO? Should we do something else? What have you learned about maybe the benefits and also maybe some downsides of approaching it the way you guys have approached it? **Archie Abrams** (01:07:07): The benefit is, so there's growth marketing who sits in growth, there's revenue marketing who sits over closer to sales. There's a brand team under Harley who does amazing work. Our president. There's marketing embedded in core and PMM, sit with the product managers there. There's shop marketing on a consumer side. So marketing is truly everywhere in the org. **Archie Abrams** (01:07:28): And I think the benefit of it is it's closest to the primary goal that those marketers are trying to do. They sit with growth so we can focus on that self-service motion. Harley is an amazing communicator, so brand sits with him so he can have a lot of influence over that. And so I think it sits with the people its most relevant outcomes are driving, which is great. It allows us move faster with less kind of coordination. **Archie Abrams** (01:07:58): I think it only works because Tobi and Harley has such amazing intuition on what the brand is, needs to be, and all of that. Some of what the CMO does of kind of creating the cohesive story of Shopify it held in their heads and they have the pen on that. **Archie Abrams** (01:08:19): And so that allows then, that piece of that CMO's job to not be as important at Shopify. But the other pieces are obviously critical, but they can be now closer to the action and where they're going to drive the most impact. The downside is things are sometimes very messy. So that's... **Lenny Rachitsky** (01:08:40): It's another example where the founder, their background and interest in skills can impact significantly the way the work is structured and who you hire and don't hire. Okay, one last question. Totally different topic, discounting. So you worked at Udemy for a long time. And from what I understand, discounting was one of the key reasons Udemy succeeded and one of the big differentiators. I'm curious what you learned about discounting, the power of discounting as a growth lever. **Archie Abrams** (01:09:09): Yeah, so Udemy is a very an online marketplace for online courses. So come on course. And I think what was happening in I started, and we were there 2012-ish was people were like, "What is this online course thing? I don't really understand what it is. I don't understand what the value is and what I'm willing to pay." **Archie Abrams** (01:09:30): And so what discounting has a really powerful effect on is it can signal value with a high list price, but then bring something down to an affordable price. And that may seem like of course that's obvious, but in online courses what was important is the list price would be high at 100 bucks. So it's associated with a college course. But what people really value this thing as was a book. **Archie Abrams** (01:09:54): And so you could signal very high, signal quality through price, which was very murky at that point in online learning. Signal value through price. Discount it to 10 bucks, or that was a typical Udemy deal. And then so 99% off, 90% off. We might see fire sales, but it changed the value in willingness to pay and then it tapped into the fact that, and still is education is very aspirational. **Archie Abrams** (01:10:23): And so what a lot of people missed in education is yes, we want people to actually take the course, but that's actually in many cases not the job to be done. That there's an emotional job that's even more important, which is I'm feeling like I'm making progress in my educational journey, and just the act of purchasing a course or the act of buying a book is progress. **Archie Abrams** (01:10:47): And so if you can make it very enticing, very high value thing, cheap, urgency, you can let people make that emotional journey by the act of purchasing, which then allowed us to actually have very good retention. Because you could keep coming back to that emotional job over and over again, which just counting with urgency allowed us to do. **Lenny Rachitsky** (01:11:10): Amazing. Well with that, we reached our very exciting lightning round. Archie, are you ready? **Archie Abrams** (01:11:15): I'm ready. **Lenny Rachitsky** (01:11:17): First question, what are two or three books that you recommended most to other people? **Archie Abrams** (01:11:21): So one, I love to go back to marketers who wrote in the 1920s. And so one that I love is Scientific Advertising by Claude Hopkins. So it's basically one of the first direct marketers that came out and he innovated on some of the concepts of copywriting and just how you sell a product around can't make this product, can't sell the product, can you tell the product will help the customer achieve their goals? And so it's really fun. I find it really fun to go back in time, because there's a lot of really good first principles thinking that I think we've actually lost in more modern stuff where it's like personalization band, it's optimization, all this stuff. Where it's like how do you actually write and sell things really effectively? Scientific Advertising, it's a great book. **Lenny Rachitsky** (01:12:09): It's just like the name alone, it sounds really cool. Especially for someone in your shoes that feels like the perfect book for your role. And I think there's so much wisdom in just the thing someone figured out many years ago about what convinces people to buy something is still true and people overcomplicate it. Just going back to the original is often really useful. **Archie Abrams** (01:12:28): Totally. And The Perfect Mile about the chase for sub four minute mile by Roger Bannister and a few other folks is just a wonderful... As a runner, it's a really fun book to read about perseverance, how these folks really, they all competed to get to that really amazing goal of under four minutes in a mile. **Lenny Rachitsky** (01:12:52): Awesome. Do you have a favorite recent movie or TV show you really enjoyed? **Archie Abrams** (01:12:58): I went back in time and I watched for the first time actually the entire season or all the episodes of The Sopranos, which was quite fun. Highly recommend. I did that in The Wire in the last six months. **Lenny Rachitsky** (01:13:13): It's a lot of watching. **Archie Abrams** (01:13:14): It's a lot watching. Work out in the morning on my elliptical or bike, so it's a nice- **Lenny Rachitsky** (01:13:20): That's smart- **Archie Abrams** (01:13:21): Workout show. **Lenny Rachitsky** (01:13:22): That's a good motivator to just work out out something. I got to watch the next episode. The Wire, it's hour long episodes and five seasons times 20. I think it's 22 episodes per season, right? **Archie Abrams** (01:13:32): Yeah. **Lenny Rachitsky** (01:13:33): Oh geez. It's a lot of watching and I did that once and I was like, "I've got a lot of episodes to watch," but incredible. Okay. It's funny you should say The Sopranos. I feel like a number of people recently told me they're watching the full Sopranos again. It's like a trend recently for some reason. **Archie Abrams** (01:13:50): Oh, interesting. **Lenny Rachitsky** (01:13:51): Anyway, do you have a favorite product you've recently discovered that you really love? **Archie Abrams** (01:13:54): So the AI music creator. My kids and I... I'm the least musical person in the world and it's been amazing. My kids and I will create songs together about our days, about what's going on. So it's just been really fun to be able to have a musical experience for a non-musical person, and have that creative experience for them and it's been really awesome to use. **Lenny Rachitsky** (01:14:15): Suno is Insane. I think it's Suno.ai, folks want to check it out. It's just such a fun party trick too, just to write a song on the spot about something that you're thinking about. Awesome. Two more questions. Do you have a favorite life motto that you often come back to, find helpful and worker life? **Archie Abrams** (01:14:31): Yeah, I often come back to the plan is the plan until it's not. And it's basically like we have a plan. It's the plan, it's our best, let's commit to it. But acknowledge it might change and we'll deal with it then. But if the combination of we have a plan, stay focused on that, with also the acknowledgement that you need to be flexible, and try to combine those two sometimes contradictory things of focus plan with we got to be able to react in an effective way. **Lenny Rachitsky** (01:15:01): Reminds me of strong opinions loosely held as a concept. **Archie Abrams** (01:15:07): Totally. **Lenny Rachitsky** (01:15:08): Awesome. Okay, final question. So I asked your wife what to ask you when you came on this podcast and she suggested that I ask you about your late father who had a lot of impact on your leadership style. So here's my question, what did you learn from your dad that impacts the way you work today? **Archie Abrams** (01:15:26): Yeah. My dad a lot is a father, and he was an entrepreneur in technology. And I think one of the things that I so appreciate about his leadership style was the empathy, and curiosity, and kindness that he showed in everything. And I hope in some of the stories that of him, it's like no matter who anyone was, curious, love to engage and learn from. And I hope that's something that I try to take inspiration from is just be with everyone kind and learn from everyone you're with and around. So something I think about a lot. **Lenny Rachitsky** (01:16:08): That super resonates. He sounds like a wonderful human as are you. Archie, this was wonderful. We touched on so much. We covered so much. I feel like we could go on for many more hours. Maybe we'll do round two as you learn more things at your time at Shopify. Two final questions. Where can folks find you online if they want to potentially reach out or follow the stuff you're up to, and how can listeners be useful to you? **Archie Abrams** (01:16:30): So not super on social media. But on LinkedIn, check me out, send me a message. And then yeah, if folks are hiring a bunch of folks, growth marketers, PMs, engineers, data folks, UXers, you want to work at Shopify and growth or other parts? Fully remote. So we'd love to have great people join. **Lenny Rachitsky** (01:16:54): Awesome. And that last point, I think I'll just highlight one of the few remaining fully remote tech companies that is not returning to work. Returning to the office [inaudible 01:17:05] work. Definitely work. **Archie Abrams** (01:17:07): Yes. Yes. **Lenny Rachitsky** (01:17:09): Amazing. And sounds like basically you're hiring across all functions. **Archie Abrams** (01:17:12): All functions. **Lenny Rachitsky** (01:17:13): Perfect. Archie, thank you so much for being here. **Archie Abrams** (01:17:17): Thank you Lenny, it was fun. **Lenny Rachitsky** (01:17:19): Bye everyone. **Lenny Rachitsky** (01:17:21): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [10/17] Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) **Lenny Rachitsky** (00:00:00): You're one of the first 10 employees, you're the first product manager. It was when you joined, the founders didn't really have an idea figured out yet. When they landed on an idea, and then ended up being wrong, ended up not working. Six weeks after you joined, there was a pivot. **Raaz Herzberg** (00:07:01): At the time, we didn't really have a solid product yet. We would have 10 to 15 meetings every day with potential customers. I was hired as the first product manager. I sat in on those calls. **Raaz Herzberg** (00:07:01): I still did not exactly understand what we were going to build, which was confusing, because I was a product manager, so I was supposed to start building it, and so, at some point, it was like, "I have to ask, what exactly are we doing here?" And that ended up pivoting us around to cloud security. **Lenny Rachitsky** (00:07:01): So things started to click a little bit more, you started seeing enthusiasm. Can you talk about just what that phase was like? **Raaz Herzberg** (00:07:01): We really felt the type of questions change, right? Silly. The call sounded like, again, "How are you pricing this, or when can we start doing a POV?" I think naturally, as human beings, you have a bias to look for affirmation, versus a bias for what you don't want to hear. **Lenny Rachitsky** (00:07:01): You started as an engineer, you moved into product, and now you're marketing, which is not a traditional path. **Raaz Herzberg** (00:07:01): I had a ton to learn about marketing, with what I knew really well, with ... **Lenny Rachitsky** (00:07:01): Today, my guest is Raaz Herzberg. Raaz is chief marketing officer and VP of product strategy at Wiz. Before moving into marketing, Raaz was an engineer, and then, for most of her career, was a product manager. Prior to Wiz, Raaz led security products in Microsoft, including Azure Sentinel, and with Wiz, moved from VP of product to CMO. **Lenny Rachitsky** (00:07:01): If you haven't heard of Wiz, it's not only the world's fastest growing security company, it's also the fastest growing software company in history, hitting 100 million ARR, just 18 months after founding, and then, just under five years after founding, was rumored to be exploring an acquisition by Google for over $23 billion. **Lenny Rachitsky** (00:07:01): Even more wild, as you'll hear in our conversation, the team initially went in circles on what they wanted to build. And it took them awhile to actually land on the idea that is basically the most intense product market fit of any B2B company ever. **Lenny Rachitsky** (00:07:01): In our conversation, Raaz shares what signals told her and the team that the original idea wasn't going to work, and that what changed in their conversations, when they finally found product market fit, why she moved into marketing, and what she wished she knew as a product leader from her new marketing lens, also, her perspective on marketing, and what marketing people often get wrong, and why CMOs often fail. Also something she calls the dummy explanation. Why you need to pay attention to where the heat is within the organization. **Lenny Rachitsky** (00:07:01): She shares her most contrarian take on leadership, and so much more. This was such a fun episode, and there's so much to learn here for product leaders, for marketing leaders, and for founders. **Raaz Herzberg** (00:07:01): Thank you for me. **Lenny Rachitsky** (00:07:01): So I want to start by giving a little context on Wiz, for folks that aren't super familiar with the company. You launched just under five years ago, at this point. Within 18 months, you all hit a hundred million ARR, which is the fastest growth rate in history of any software company. It's faster than the two other companies I've had on the podcast, that also claim to be the fastest growing software companies, Deal and Ramp. You guys grew even faster. **Lenny Rachitsky** (00:07:01): I read that you are at over 500 million ARR now. I know it's also not confirmed, but a certain company that rhymes with Loogle, offered to buy you guys for $23 billion, and y'all turned that down, decided to stay private. And also, something like 50% of Fortune 100 companies are customers of Wiz. **Lenny Rachitsky** (00:07:01): Is there anything I missed? Anything I got wrong? **Raaz Herzberg** (00:07:01): Never heard of that Loogle company, but other than that, yeah. **Lenny Rachitsky** (00:07:01): Okay. Okay, great. We're going to come back to that. What's even crazier is in spite of that, when you joined the company, you were employee, something like, number seven? **Raaz Herzberg** (00:07:01): Yeah, we kind of started, I feel like, the founders, and the first six, seven employees, we just started at once. **Lenny Rachitsky** (00:07:01): **Raaz Herzberg** (00:07:01): Yeah. Yeah. **Lenny Rachitsky** (00:07:02): And what I read is that when you joined, the founders didn't really have an idea figured out yet, when they landed on an idea, and it ended up being wrong, ended up not working. Six weeks after you joined, there was a pivot. **Lenny Rachitsky** (00:07:02): So the fact that that was true, and you went from this, "This isn't working," to boom, $100 million dollars AR, I want to spend some time here, because I think there's a lot people can learn here. **Lenny Rachitsky** (00:07:13): So let me just ask, looking back at that point when the idea wasn't working to realizing, "Hey, maybe this is a better idea," what do you remember are some signals that told you this isn't working, and okay, maybe this is, because a lot of founders are in that stage with their products? **Raaz Herzberg** (00:07:31): When we started, it wasn't even Wiz. The company was literally officially founded as Beyond Networks, because there was this idea of, "Hey, we want to do something in the network security space." **Raaz Herzberg** (00:07:43): Actually, myself and the founding team, and also, the other five engineers that started with us, we actually all came from a background of building cloud security products before, but this time it was like, "Okay, we actually don't want to do cloud security, we want to do network security." **Raaz Herzberg** (00:08:00): What happened was in those initial few weeks, it also, we started was literally, exactly, Wiz was founded together with COVID. It was that March when the whole world shut down. Suddenly, everything went terribly, terribly strange on all of us. That's when Wiz started. **Raaz Herzberg** (00:08:19): So it was like, our days looked like talking to 10, 15 customers. Wiz is a B2B product, the buyer is the CISO, the people, the person that owns basically security for the entire company. So we would have 10 to 15 meetings every day, with potential customers. **Raaz Herzberg** (00:08:39): At the time, we didn't really have a solid product yet, but we had an idea, and the deck explaining our idea, and what we're going to build, and why. We were all a very technical group of people, and especially, our founding team, a staff, our CEO at Wiz. Before Wiz, he led the entire division of all of the Microsoft cloud security products. So they're very, very impressive, very technical, very well known and respected in the industry. **Raaz Herzberg** (00:09:09): And so, we would join a call, and kind of present and walk through our idea, and the person on the other end would be like, "Oh, it sounds interesting. Oh yes, sounds interesting, we'd love to hear more. Yes, perfect. Sounds interesting, we'd love to hear more." And you finished calls with a good feeling, like the person said, "Oh yes, interesting, interesting." **Raaz Herzberg** (00:09:32): But like you said, I was hired as a first product manager. I sat in on those calls, sometimes officially participating, sometimes, even, not officially participating, but listening on all of the calls, and I finished a couple of weeks of that, which is a lot of calls, I think, two weeks or something. I still did not exactly understand what we were going to build, which was confusing, because I was a product manager, so I was supposed to start building it, in some ways, go to the dev team and start building it. And that was a point where I felt like, "I don't know what we are talking about exactly." **Raaz Herzberg** (00:10:10): Now, I really thought, "I don't know what we're talking about. I thought they all understood what we're building, and I thought every customer we had in the call, understood that we were building." It's just that I did not understand what we were building. **Raaz Herzberg** (00:10:24): At some point, it was like, "Okay, I have to ask. What exactly are we," like, In the details, right? Not in describing a big problem, in a high level, big potential approach to solving it, but what exactly are we doing here? **Raaz Herzberg** (00:10:44): And I think that that ended up opening a really deep discussion of, "Okay, wait, maybe we are telling a bit of a broad story, and maybe the person on the other end is not going to tell you." They're not incentivized to tell you, "You know what? I don't know what you're talking about." **Raaz Herzberg** (00:11:02): It's really, I guess they felt a bit like me in some ways, and they were like, "Oh, it's a really smart group of people. I'm sure they're building something interesting." So yeah, interesting. They're not incentivized to really dig, deep dive into the problems, right? **Raaz Herzberg** (00:11:14): So I think that opened up a discussion for us, and we kind of understood that we were listening in the wrong way, maybe, that we were looking for positive reinforcements, but not really listening intently to signs of deep enthusiasm, and that ended up pivoting us around to cloud security. **Lenny Rachitsky** (00:11:31): There's so much to learn, just from the short story, and I want to get into what you started hearing that made it sound like, "Okay, wait, maybe this is a better idea." But first of all, just the fact that you're doing 10 to 15 calls a day, you said? **Raaz Herzberg** (00:11:41): That was a bit of, in some weird way ... Again, Wiz was founded in that terrible March, where the world closed down. It seemed, at the time, a really bad time to start a company. Markets were frozen, and everything. **Raaz Herzberg** (00:11:55): Even my mom, which knows nothing about what exactly I do or why, I mean, I left Microsoft to join Wiz, even my mom was calling me and telling me, "This is not a good time to join a startup." But it ended up being in some ways, like an advantage, because everybody were home. Suddenly, everybody were home, no meetings, no travel. **Raaz Herzberg** (00:12:15): So suddenly, C-Sales, which are busy people, and we started, originally based in Tel Aviv, so we couldn't even fly, but suddenly, it didn't matter. Because, I mean, everybody's home. So yeah, we took 10-15 calls a day, back to back to back. **Lenny Rachitsky** (00:12:30): I think that alone is a really important lesson of just, that's how you discover something that isn't working/find the thing that is working is, do many, many calls. **Lenny Rachitsky** (00:12:38): That is a lot of calls. I don't even know how someone has time to do 10 to 15 calls a day. But again, I think that's how you do this. So I think that alone is a really important lesson for folks to take away. **Lenny Rachitsky** (00:12:46): I love this point, that people are going to try to be nice to you, especially if they think you're really smart, and especially if you're describing things that might be helpful to them, but what you're sharing is, you need to not trust, that often is deceiving. **Lenny Rachitsky** (00:13:03): Talk about what it felt when it moved from just, "Oh, this is cool, this is nice, and maybe let's talk more," to, "Oh, maybe this is actually something they'll buy." **Raaz Herzberg** (00:13:12): We really felt the type of questions change. Suddenly, the call didn't end, was like, "Oh, this sounds super interesting. Sure, please update me. I'd love to hear more." Certainly, the call sounded like, "Wait, again, how are you pricing this? How much will this cost?" Or, "Wait? When can we start doing a POV? How long is a POV?" Or somebody would finish the call, and be like, "Okay, I know exactly who I need to connect you to in my team." **Raaz Herzberg** (00:13:35): Those are really strong indications that are the type of indications we learned to look for. Although there's something I think, at the beginning of a company, it's very scary. I think naturally, as human beings, you want to get affirmation from the other side. **Raaz Herzberg** (00:13:53): So you're actually, you have a bias to look for affirmation, versus a bias to look for what you don't want to hear. That's just natural, being a person. **Raaz Herzberg** (00:14:04): So I felt like, that is what we ended up really being in tune with. "No, I have to understand. They're intently interested. They want to connect me to somebody. They want to know how much this costs." **Raaz Herzberg** (00:14:15): If somebody just tells you, like you said, "Oh, super cool, yeah, I want to take this as a good sign, but I shouldn't." **Lenny Rachitsky** (00:14:23): It's almost like you need to see them pushing for the next step is what I'm hearing is, "Let's do a POV, what's the next step to do this? I want to connect you to this person, to talk further about this," versus just, "Oh yeah, this is awesome. Thank you." And then, okay, bye. **Raaz Herzberg** (00:14:34): Yeah, exactly. And also, in B2B, that is really the process you have to take, after you have to get connected to the actual team that will test the tools, will deploy it. There needs to be real passion about doing something, and I guess that is the difference. It's real passion about, "Hey, I want this right now." **Lenny Rachitsky** (00:14:54): The other point you made is that you were the person, nobody was saying this thing that was this elephant in the room, almost of, "What are we even building? I don't understand what's happening here." **Lenny Rachitsky** (00:15:05): I read somewhere that you were like, you told, "I need to quit. I don't understand what this is, and I'm not the right person for this role," and it turned out, nobody understood exactly what was going on. Can you share that story? **Raaz Herzberg** (00:15:17): It's funny, because it's a story that some of the founders tell, and they tell differently. They tell, "She came to us, and she was like, we have to rethink," but that was not my perspective at all, right? My perspective was genuinely, "Okay, I have to confess, that was my perspective." **Raaz Herzberg** (00:15:38): I was sure that I was the only one not understanding. It's hard to get the courage, I guess. Sometimes, it's hard to get the courage to say, "Actually, I don't understand." But I think by now, in my career, it's my favorite question. **Raaz Herzberg** (00:15:56): I feel like I say, "I don't understand," a lot of times a day. I think, if you build a company with the right type of culture, in a sense, then it's not a shame to say, "I don't understand, or please explain again." **Raaz Herzberg** (00:16:14): It's having that culture in place that enables it. And I also have to say, when I think of the founding team, and the founding team in Wiz, Wiz is a very flat organization, in some ways. It's not about seniority, it's really about driving impact, and everybody can have a seat on the table, and voices are heard. **Raaz Herzberg** (00:16:32): And I think it also reflects really highly about them, just giving me the seat at the table, in a sense, to be even able to say, "I don't understand." **Raaz Herzberg** (00:16:41): Then, when I'm saying I don't understand, not actually being open to, "Oh, maybe we have to also think again." I think that tells a lot about the culture, even, to this day. **Raaz Herzberg** (00:16:52): But it's definitely, for me, it's a very learned quality over my progression of my career, actually allowing myself to be more vulnerable, more easier in saying, "I don't understand, or I don't know." **Lenny Rachitsky** (00:17:05): I love this lesson so much. One, partly because you said it's really scary to be the person that's like, "I don't understand," right? **Lenny Rachitsky** (00:17:12): That puts you, that's a very vulnerable thing to say, because you're like, "What? She doesn't get it. Maybe she is not as smart as we thought." That can't be easy, to be the person doing that. **Lenny Rachitsky** (00:17:22): The other thing is this reminds me of Tomer Cohen, LinkedIn CPO, has this really great phrase, "We may be wrong, but we're not confused." I feel like that's exactly what you're saying here. **Raaz Herzberg** (00:17:31): Exactly, which is why I love this question to this day. I love it. I do think that if something is not easy to understand, then maybe it needs a bit more chewing on it. **Lenny Rachitsky** (00:17:46): I love that. Okay, so things started to click a little bit more. You started seeing enthusiasm. Can you talk about just what that phase was like, and any lessons from just that turn to, things are actually working? **Raaz Herzberg** (00:17:59): I have to say, I think the feeling, after we made that switch, what ended up happening is that after that big conversation that we know, I don't understand, we ended up having, and this never happens, I don't think it's ever happened since. It was almost a long, five-hour discussion, with all of the founders, where we decided to move away from that pivot to cloud security, which is what we really, in some ways, know best. **Raaz Herzberg** (00:18:25): That's our background, that's what we did before, and we felt the problems there was so big and so strong, and once we started having the conversations with the new pivot to cloud security, the room felt so different. I mean, it was all over Zoom, but our room, it felt very different. **Raaz Herzberg** (00:18:49): Once we found the right path, it was so easy to distinguish it from the wrong path, in some ways, because we did start getting those strong signals. And in some ways, they pushed us forward. **Raaz Herzberg** (00:19:02): A customer was like, "Okay, I want to start a POV," and we're like, "Oh, okay. Of course. Let's schedule for Thursday next week, or something. We tried to even postpone it a bit, because we had to run fast." **Raaz Herzberg** (00:19:15): Another learning I have from that phase was, I explicitly remember that first conversation, where it was like, "Okay, let's do a POV." It was a Fortune 10 company, a really big company, and we had a beginning of a product. We wanted to buy some time, until we actually started the POV. Just because of that, we said, "Okay, also we want to really understand exactly what they will connect to us as part of the POV," because everything was so initial. So we put this long list of technical questions, "What are you using for this? What are you doing here? What are you [inaudible 00:19:47]?" On the one hand, because we needed to know, to actually build a thing, on the other end, just because we wanted to buy time, and I was super scared. **Raaz Herzberg** (00:19:55): I remember studying that e-mail, and being like, "Ugh, they want a POV. And now, I'm going to scare them away, with this list of things they have to do, and list of questions, like it's counterintuitive." **Raaz Herzberg** (00:20:06): But actually, it came back filled a day later, and I remember my lesson being, "You know what? This is actually good. I want to make sure they're committed, right? I don't want to push somebody into a POV, if he is not committed to me at this stage." I mean, it's not a well-built product. It's going to be a journey we take together, so they need to really want it. I need that commitment from the other side. **Raaz Herzberg** (00:20:32): I'm not trying to push something on someone, especially not at this point, and my opinion, not ever, not even today, not even when you sell at large scales. I'm not trying to push anybody to anything, I really want to make sure they want it. I have to feel that want back. So that was another learning for me. **Raaz Herzberg** (00:20:49): It's like, first of all, when it works, it works, and you do know when it works. And the second is, "Don't be too afraid to get the pull from the customer." It's okay. You need that pull from the other end, as well. Don't push too hard. **Lenny Rachitsky** (00:21:03): I know people always talk about, "Look for pull," and I love that you're describing what pull looks like. Somebody's next day, filling out a really complicated annoying questionnaire, because they just want this product they've never heard of before you chatted with them. **Lenny Rachitsky** (00:21:14): Now, they're like, "Just give it to me now. I'm going to do anything you need." Is there anything else along these lines, before we move into your current role and learnings there? **Raaz Herzberg** (00:21:23): I also think that one of the things we did very, almost uniquely, it was, was that, because things started rolling so fast for us, once we found the right path, we ended up selling before we had a seller's team. **Raaz Herzberg** (00:21:37): We ended up, almost in some ways, always being behind, right? Okay, I'm closing contracts with people, I haven't hired my first salespersons, I don't know what we're doing here, I don't know how to have the conversations. **Raaz Herzberg** (00:21:49): But we ended up learning so much from that, from us, ourselves, us being the founders, myself, closing the deals, actually going all the way to contracts and everything, by ourselves. We learned a lot, we learned a lot. **Raaz Herzberg** (00:22:04): And then, when we hired our first sales hire, it was also like, "Look, we sold a couple million of this, so you, for sure, as a salesperson, you kind of give that confidence." **Raaz Herzberg** (00:22:14): So I felt like there was multiple places where that ended up happening, just by accident, because of how fast things ended up happening for us. Actually, it was a really good learning experience to do it for the first time yourselves. I think, sometimes, when you start building a company, you have this wish that if you can't do something, you're going to hire the right person, and he will be able to do it. **Raaz Herzberg** (00:22:36): Okay, I feel like my message is not clear enough, and we just started this company, it's okay, I'm going to hire my first product marketer, and that's going to be it. Or I feel, we can't close a deal, because I need to hire my first salesperson, and that will be it. **Raaz Herzberg** (00:22:49): I hardly find that, I don't think we've ever had that work for us, honestly. It's like, if you can't do it one time end to end, and you're the core, core group, the chances of just bringing somebody from the outside to solve that problem, it's wishful, in some ways, but it never ends up that way. **Lenny Rachitsky** (00:23:08): I love this advice so much. There's kind of two parallels here. If the founder can't do it, who has the most context and passion and motivation? It's unlikely an employee's going to be able to do it. And it's similar to the selling point, that if your early customers aren't pulling from you, later customers are not going to have a good time, right? **Lenny Rachitsky** (00:23:27): It's like, the most passion comes early. How long did you all stay, doing sales as a founding team? How many millions ARR, roughly, do you remember? **Raaz Herzberg** (00:23:39): Oh, a couple million. I don't remember the exact- **Lenny Rachitsky** (00:23:41): A couple million? **Raaz Herzberg** (00:23:41): Yeah. **Lenny Rachitsky** (00:23:43): Awesome. That's incredible. Often, the heuristic I hear is, one or two million ARR, and then you start to hire salespeople. Okay, that was an awesome lesson. I love that. **Lenny Rachitsky** (00:23:53): I want to talk about your current role. So currently, you're CMO, and also, VP of product strategy at Wiz. You started as an engineer, you moved into product, and now you're in marketing, which is not a traditional path, especially for product people. First of all, why did you decide to move into marketing, from product? **Raaz Herzberg** (00:24:11): Yeah, it's not a traditional path for anyone, I think, also not one I would have necessarily expected myself to be on. First of all, it's not like I had this plan, right? **Raaz Herzberg** (00:24:22): In general, I myself, people sometimes ask me about career progression, and I never had a plan for anything. That is just, the only thing I did was follow good people around. That's it. I never had a plan for anything I do. **Raaz Herzberg** (00:24:36): So myself, coming to Wiz was following Assaf and Ynon in the founding team. And two and a half years into Wiz, at that time, Wiz was already, it was a very clear product market fit. **Raaz Herzberg** (00:24:50): Our revenues were already there. We had a sales team that was fully functioning, but at that point at Wiz, we felt marketing was still something we didn't fully figure out. It wasn't working super well for us. We were at this stage where, yes, if there was a POV, a proof of value happening, we would win it, versus competition. **Raaz Herzberg** (00:25:13): But many times, we would come to a customer, and they would be like, "Oh, I wish we heard of Wiz, we just signed with a competitor," which it breaks your heart, because I know they would have chosen me, had they heard about me in time. So you started feeling that challenge around awareness and marketing. So two and a half years into the company, basically Assaf, our CEO, asked me if I was willing to take on marketing. **Raaz Herzberg** (00:25:42): Originally, I thought it was, I remember, he knocked on my, bothered me while I was working on my computer, and we went into this super cold room. It was like, when you were a fast-growing startup, all of the rooms are always full, you know what I mean? **Raaz Herzberg** (00:25:58): We went into this server room, which is freezing cold, and I was in the middle of something, and he told me, "I think you should lead the marketing org now." I told him, "Okay." I was like, "Assaf, I'm cold, I'm going back to work. I have a lot to do." It sounded that bizarre to me. **Raaz Herzberg** (00:26:12): It's not only, do they not know marketing, I spent my life in engineering, and in any product, it's not the go to market side, even. I was never part of the go to market, or I have never heard of a lead in my life. I did not know the word "pipeline." **Raaz Herzberg** (00:26:26): All of those things were very remote to me, very. It sounded like such a bizarre motion. But that was on a Thursday, and then, I spent the weekend, because he asked me to, and again, I just follow good people, and do what they tell me to do. **Raaz Herzberg** (00:26:42): So I spent the weekend listening to a ton of podcasts, talking to CMOs, just to even understand what do CMOs do, what do marketing orgs do in B2B companies? **Raaz Herzberg** (00:26:51): Then I ended up deciding to just give it a try, and we did not know if it was going to work. I also don't know if it's going to work forever, but we ended up deciding to give it a try. **Raaz Herzberg** (00:27:04): I think the thing that's convinced me to do it was that, in some ways, I really felt like if, in the early days of the company, finding product market fit is a major block for the company. And then, building a sales organization becomes a major block for the company. **Raaz Herzberg** (00:27:19): I felt like we were at the point, where you have to figure it out to scale. At some point, of every product, people start looking really heavily at brand, whether we think that way, or we don't. When I buy my iPhone, I have no idea how it really is compared to an Android phone. I did not look at the specs. I truly have no idea. **Raaz Herzberg** (00:27:39): So why do I buy an iPhone? I just know it's the thing to buy. B2B products, even the most complex products, people are still people. They still buy it, because brand matters a lot. **Raaz Herzberg** (00:27:53): That was part of what convinced me that this is super important. So if I'm asked to attempt, at least try, because I do think it's really important. **Lenny Rachitsky** (00:28:05): I love this. I love the detail of the cold room, by the way. Speaking of cold, when we were chatting earlier, you had this really beautiful metaphor of heat. And where heat is within an organization and how it shifts, as the company grows. Can you share that? **Raaz Herzberg** (00:28:19): Yeah, it's exactly that. It's like that in the early, early days when we just started with, I remember, I felt like the heat was in the product kitchen. Because it's like, everybody's waiting to have something, people want to start doing something, right? **Raaz Herzberg** (00:28:34): Then they felt like, "Okay, you start understanding it," and now, the heat moves a bit to the engineering side like, "Okay, build it. Somebody wants it, build it, make it work." **Raaz Herzberg** (00:28:44): Then I felt, "Okay, so we close a couple of deals now," right? We had our first couple of clients. Now you bring in sales, and the heat moves to sales, because they're like, "Okay, we have this thing, now go sell it." And then, the heat starts moving to marketing, in my opinion, where it's like, "Okay, we have a product market fit. Salespeople can sell it, but they're saying, 'Give me more pipeline like, 'Hey, nobody heard of Wiz. Give me more.'" **Raaz Herzberg** (00:29:09): So the heat moves to marketing, at that point. That's kind of, I've always felt like, yeah, in some ways, I also naturally, I guess, follow the heat. **Lenny Rachitsky** (00:29:18): And I think it's actually more so, that they put the best people in the places that need the most help. Clearly, that was you, when they did that. **Raaz Herzberg** (00:30:51): I think Shardul is very kind. I deeply remember that meeting, because funny enough, it was my first board meeting ever. That is a funny thing by itself, because Wiz's board, we have Shardul on our board, we have Doug Leon, and we have Jeff from Insights. **Raaz Herzberg** (00:31:09): It's almost like, it's very humbling to sit down in front of those people, period. And since I decided to take marketing, and I took to the CMO role, this was also my first board meeting ever. **Raaz Herzberg** (00:31:23): And also, it was the meeting where it's, in some ways, I was not that. I was like, "Okay, we took our product manager person, she was never a CMO at any company, and now she has a CMO here." So it was just very, the whole setting was very stressful for me. **Raaz Herzberg** (00:31:43): I just ended up, it was like, I think we just had the meeting two months after I took over marketing. So it was more of an update of, "Hey, those are the changes I've made, and this is how I'm thinking of approaching this, and this is all the things I've done in the past two months." **Raaz Herzberg** (00:31:59): It's funny, because I'm a very non-traditional marketer, just because I really don't know marketing. At this point, I kind of know already, because I've been doing it for two years, and I read a lot, but at that point, I generally did not know. I could not even explain to you how untraditional my approach was, in some ways. **Raaz Herzberg** (00:32:16): I just really did what I thought. I mean, I had a ton to learn about marketing, but what I knew really well was the problem we solved, and I really knew our audience. **Raaz Herzberg** (00:32:28): I myself, I come from security, I come from cloud security, I read all of the right Twitters, and I follow all of the right people on Twitter, and I read all of the right blogs. **Raaz Herzberg** (00:32:36): I know it's funny, I know what matters, I know it's interesting right now, generally because, this is my space. I mean, I live in that space, truly, as a customer. So I was just thinking, "Okay, what are things I could do, to start fixing the problem that mattered most?" And that was, nobody heard of Wiz at that time. **Raaz Herzberg** (00:32:59): Those were just, I was saying, "Okay, I think, in order to do that, I'm willing to take chances, I'll just focus on making a lot of noise." And I think, even in that short time of two months, we saw changes happening already, in some ways. **Raaz Herzberg** (00:33:16): So I think, that what's Shardul meant by that, of course, although I do think he's being very, very kind, and I have learned a lot from many, many marketing people, including my own team, by the way, which is another interesting thing., right? **Raaz Herzberg** (00:33:28): I took over a large team, of people who are marketers, and I'm this person knows nothing about marketing, but will now manage this. So I learned a lot from many marketers, including my own exceptional team. **Raaz Herzberg** (00:33:41): But I think he meant, really looking at it differently, just thinking, "Okay, what is the end to the goal of having the right people hear the right thing about my company, ASAP," versus a ton of traditional aspects, of building pipelines and different things they really did not know how to do, at that time. **Lenny Rachitsky** (00:34:01): So following that thread, I'm curious, what is it that you think CMOs mistake, or often do wrong? Why do you think CMOs often don't work out, and they brought in someone like you, with this very fresh perspective? Where do you think folks often go wrong? **Raaz Herzberg** (00:34:16): First of all, I think CMO is a very, very hard role. And also, I think it's a role that is very hard to do without a lot of trust, and without a deep connection to the founding team. Everything you do in marketing is very visible, and you're kind of touching something that matters so deeply to the founding team, and you are the one representing it to the world. **Raaz Herzberg** (00:34:43): So it's very hard to build that trust, and it's very easy to break it, because one bad ad, or something that one of the founding team will say, "Oh, this is not us, this is not what I mean, this is not the right thing," it breaks the trust really easily. **Raaz Herzberg** (00:35:00): And I think it's especially challenging. I mean, I really don't know how somebody that does not come from from a security background could be successful deeply, in this type of a role, for a company like Wiz, because it is really about understanding your customers, and it is really about understanding your product. I think that's very, very hard to gain. **Raaz Herzberg** (00:35:21): So I guess I would say, I think it's the deep trust you need with the founding team, and the really deep connection you need to the product, and to the market. I think both of that, when you come from the outside, in a way, because you are not part of the founding team, and also, you maybe come from outside the market, sometimes, because it's a very technical market or it's a very different domain, then I think it's two really big challenges. **Raaz Herzberg** (00:35:47): I'm not saying you can't come over them, but I think, it's just a very, very hard job. On top of that, it's a very diverse job. When I was a product manager, I managed product managers. I know exactly what they like, what they don't like. That's my audience, I know who to hire. I have the best network, I know every single PM and security around me. It's so different. **Raaz Herzberg** (00:36:05): When you are a marketing leader, you manage performance marketing, which is a numbers game. You manage designers and brand, and then you manage events and field. There's nothing in between those things that is deeply correlated. Sp it's just a very, very challenging and very interesting role. **Lenny Rachitsky** (00:36:23): This trust point is so interesting, especially based on what you said earlier, where what you want it to do is create noise, take some risks. That's extra hard, if you're not someone that the founding team trusts. **Lenny Rachitsky** (00:36:35): Can you share some of the things you did that helped create noise, and get the Wiz name out there, that might inspire folks of like, "Oh, that was really cool, we should do something like that?" **Raaz Herzberg** (00:36:43): Yeah. Another insight I had about marketing in the early days was how different it is from product. As a product manager, I was always, and still believe, it's so important to think really hard about everything you add. Less is more. **Raaz Herzberg** (00:36:59): If you decide to build a feature in a product, then A, you're taking engineering time, which is the most valuable resource in every company, in my opinion, and B, in some ways, you can never take it back. It's complicated your product. Even if one customer likes it and uses it, at least at B2B, you're never going to be able to suddenly take it away. **Raaz Herzberg** (00:37:19): Every new feature you add to your product, you'll have to think about, "Okay, how does it work with that feature?" So it's like making a mistake, adding something to the product that is not the right thing, or that is not truly, truly what your customer needed, even if it's what they asked for. But if it's not what they truly needed, it has a huge cost associated with it. **Raaz Herzberg** (00:37:40): Marketing is quite the opposite, in my opinion. There's no cost to anything, no maintenance to anything, no technical depth, no anything. If tomorrow I post a video on Wiz's LinkedIn page, and I think that video is super funny, and nobody likes that video, nothing happened. **Raaz Herzberg** (00:37:54): Tomorrow, I'll post a different video, no maintenance, bye-bye, forgot it ever happened. In some ways, it dawned on me how opposite those things were, and I was like, "Okay, we have to just use it to our advantage. Let's try everything, let's try everything. I'm trying to make noise." **Raaz Herzberg** (00:38:11): It was right before, when I took over, it was before RSA. RSA is the Super Bowl of security companies. So it's where every vendor's come to showcase, and all of our buyers are there, and you know how those conferences go. You pay for having a space assigned to you, and it's a very expensive space to assign to yourself. **Raaz Herzberg** (00:38:33): And we had the exact same spot we had the year before. I said, "Okay, it's a booth at a conference. I'll just make it the weirdest booth ever, because my goal is just having people look and be like, 'Oh, what is Wiz, right? Because they've never heard of me." **Raaz Herzberg** (00:38:48): Instead of doing a classical cyber booth, I decided to say, "Okay, let's scrap our booth, and do a Wiz of Oz booth," which literally looked like a Wiz of Oz booth, and we had actors, like Dorothy, and all those things hanging around there. **Raaz Herzberg** (00:39:03): It looked nothing like any booths in the show, which is a cybersecurity show, things are red and black, and people with hoodies. And we decided to take a completely opposite approach. **Raaz Herzberg** (00:39:14): In general, I also decided that we're going to take a completely opposite approach was brand. I wanted Wiz's brand to, again, my first motive, stand out. **Raaz Herzberg** (00:39:23): I wanted Wiz to have a very positive, optimistic type of brand. So I went all in on, "Scrap whatever we were doing before, which was dark, and go pink, go bright blue, always go optimistic, and focused on magic, not scaring people from the facts, but magic." And that ended up, and it was scary, don't get me wrong. **Raaz Herzberg** (00:39:45): Half of me was like, I remember feeling so scared walking to the show, to the floor trade. Because I was like, "Is this going to be the most terrible, bizarre? Are people going to be like, 'What is she thinking?'" So I knew it could either be a failure, or a hit. **Raaz Herzberg** (00:40:04): And it ended up, the amount of people that stopped by our booth was five times the amount of people that stopped by the year before. It's the exact same space, the exact same investment, because you invest in the space. **Raaz Herzberg** (00:40:16): But also, ever since we do themed booths, every time, we change themes to keep it fun. At this point, you won't see other cyber companies even doing themes. We were just, "Okay, we'll do whatever it takes to make noise," and this is just one example. **Lenny Rachitsky** (00:40:29): That is an amazing story. You said that other companies now try to do something similar, right? Oh, man. So along these lines, when we were chatting earlier, you shared that you kind of have this mindset of being very okay with failing, that's a core part of you. **Lenny Rachitsky** (00:40:46): And it feels like, that comes up again and again in the stories you share, where you just try stuff, and you're okay if it doesn't work out. Can you just talk about that part, and why that's so important? **Raaz Herzberg** (00:40:54): Almost every single thing I've done in my career, in some ways, even before, I never thought I was going to be successful in it. I guess there's a lot of times, it's a lot of talk about being more confident than yourself. I don't know, at least for me, I don't really know if that's a real option, okay? **Raaz Herzberg** (00:41:17): I just know that I'm kind of okay with being pretty sure I'm going to fail at something, and still attempting it. That is the thing that has grown in me where, when I took the job, it was, I was sure, I was sure they got confused, that they offered to take me with him. **Raaz Herzberg** (00:41:36): I was certain that it's going to be like, "Okay, they're going to figure out that I'm not the right fit for that super smart and talented group of people," who have all worked together before, by the way, I was sure they're going to find me out. **Raaz Herzberg** (00:41:48): And I was pretty sure I was going to fail, but I will still take it. I thought I was going to fill the product manager role, too, although I did have the experience. **Raaz Herzberg** (00:41:58): So that also makes it easier to move, in some ways. If I think I'm going to fail with anything, I'm like, "Okay, whatever, I'll try," and I think over time, yeah, it releases you a bit. Sure, I might fail. **Raaz Herzberg** (00:42:09): By the way, I might still fail. It's also fine. Even in my current role, probably not for every scale, it'll make sense for me to do it, but that's also fine. It's still just giving yourself the opportunity to fail. **Lenny Rachitsky** (00:42:23): That is really empowering. Is there anything that helps you build that skill, that's not natural to a lot of people, being okay with failure, and leaning into things that they think they'll probably fail at? Where did that come from, for you? **Raaz Herzberg** (00:42:34): Yeah, depending on what you believe in, everything comes from childhood. In some ways, I do think it has to do with, I think the way my mom raised me, my mom really believed that if you're good at something, so that's not where you should invest your energy. She really believed in pushing us to the places where we were less confident in, I guess. **Raaz Herzberg** (00:43:00): I mean, I was a very shy kid. My natural inclination, as a young kid, was to close the door in my room, read a book. I had no interest in meeting other kids or doing sports or nothing, nothing, really super, super shy. And I think, also slightly unsocial by nature, really. **Raaz Herzberg** (00:43:18): But for my mom, she could have been like, "Oh, so she's really good was books and math, so let's focus. Perfect. Let her build up the skill, and be really good with that." But no, she would make me go swimming, and make me go meet other kids. **Raaz Herzberg** (00:43:32): In some ways, I feel, she always used to say that friction is good. If you brush your teeth, and there's a bit of blood somewhere, then you need to brush harder there. It's that idea, that friction is kind of good. **Raaz Herzberg** (00:43:46): If you're good at something already, then you're good at something already. So it's a bit more about learning how to learn, how to push yourself in other areas. **Raaz Herzberg** (00:43:54): I think she put hard work and courage, in some ways, or friction, mostly, above talent. Talent only gets you so far, but that hard work in the friction gets you more. **Lenny Rachitsky** (00:44:09): That is an awesome story. It's interesting that friction is good circles back to the story you shared about creating hurdles for potential prospects early on, and creating, looking for enthusiasm, where they're filling out these long surveys. How about that? **Raaz Herzberg** (00:44:24): No, it's true. You're right. It shows something. It shows if you do, it's always easier to be in inertia, right? **Raaz Herzberg** (00:44:32): That's why I also say, sometimes, it's like breakup advice I give my girlfriends over the years, where it's like, "Well, if you decide to break up with somebody, it's for sure the right decision, right?" **Raaz Herzberg** (00:44:43): Because not breaking up with somebody is much easier. It's so hard to break up. So that makes it, by default, the right decision. So it's like, yes, where there's friction, it means that you put something extra in. **Lenny Rachitsky** (00:44:53): I want to circle back to marketing/product advice, going back full circle a little bit. So folks that are in product, now that you're in the marketing world, thinking about marketing, what do you think you wish you knew as a product leader, that you think a product leader should be thinking more of, or maybe you miss, that you now see as a marketing leader? **Raaz Herzberg** (00:45:12): Having done products for many years, I really did not understand the criticality of marketing, and even of product marketing. I really did not understand deeply enough that sometimes even gap, between when you're in the product, and you really live inside the product. **Raaz Herzberg** (00:45:30): In the technical domain, you can sometimes not understand how far you are from a common person in your market, or a seller in your market. And marketing, in a lot of ways, bridges that gap. **Raaz Herzberg** (00:45:44): It's like a multiplier, but the further you get away from the core engineer, than product, then in order for the messages to move correctly, they have to be crystal clear. That is something I understood only when looking at it from the other side. If you're on the product side, you can often work with things that are fluffy or blurry or gray, okay? **Raaz Herzberg** (00:46:10): Somebody will ask you, "Can the product do this?" You'll be like, "Yeah, not exactly, but it can do, blah, blah, blah," kind of work around something, right? It doesn't have to be crystal clear, because you can kind of go around things, in a way, that when you try to scale your message, you can't. It gets lost in translation. You have to be crystal clear, black and white. **Raaz Herzberg** (00:46:29): You have to communicate very clearly, especially as an organization scales, you have to communicate very clearly. Suddenly, you're looking at the product org from the outside, in the company that scales fast. And you said, "Whoa, product marketing, in marketing, plays a really important role, in being able to take that message and amplify it." **Raaz Herzberg** (00:46:51): And if you are giving signals that are even a bit gray, fuzzy, then it's not going to work, and you can't expect them to do a good job with it, in some ways. I really, by understanding the go to market perspective, and the user perspective, and the seller perspective, I suddenly understood how things that can look simple on the inside of that side, are very complex, when you cross over to the go to market side. And I think learning the difference is so, so important for product people to understand, that they have to deliver those crystal clear messages about the product. **Lenny Rachitsky** (00:47:25): Is there an example of that, where you're like, "Oh, wow, I thought this was good, but no, nobody understands what we're talking about?" **Raaz Herzberg** (00:47:30): There's so much. I think, for example, in our domain, it's very, almost custom, to talk in a lot of initials, and a lot of things in security are, "Use initials for them." You say CSPM, for Cloud Security Poster Management, and you use a lot of those types of initials, and you keep assuming that the world knows what you mean. **Raaz Herzberg** (00:47:51): But then, when actually looked at things over, from the marketing side, if you ask our product people, engineers, "Where does our product fall in terms of category," it would be CNAP, Cloud Native Application Protection. But if you go over and you look at Google, people are not Googling that word. They're Googling, "Cloud security solution," right? **Raaz Herzberg** (00:48:13): So that's just a simple and silly example, but it's that example, that when you live inside something very technically inside your market, inside domain, you're very remote, sometimes, by accident from the buyer. So a lot of those learnings clicked for me, only once they saw everything from the marketing side. **Lenny Rachitsky** (00:48:32): You have this concept that you described as a dummy explanation, when someone, you just need it to feel really, really simple. Can you add some color to that? **Raaz Herzberg** (00:48:40): Yes. It's when I, now in marketing, and in everything we write, and everything our team produces in terms of anything, anything written by Wiz, I keep going back to, I don't want us to forget that we are inside our own bubble. **Raaz Herzberg** (00:48:56): We go to work at Wiz every day. Wiz is a cloud security company. We live inside our own bubble, but reminding ourselves that customers don't live in that bubble, they're people in the world. Their life is not Wiz. **Raaz Herzberg** (00:49:11): So every time you write something, I wanted to not assume knowledge about Wiz, or knowledge about the product, or deep knowledge about the market. I'll give just a simple example. **Raaz Herzberg** (00:49:23): Wiz itself is based on, part of the deep innovation that Wiz brought to the market that enabled the scale, was a very high correlated signal that's based on a graph database. So inside Wiz, we have the Wiz graph database, for security. **Raaz Herzberg** (00:49:37): If you write something that says, the Wiz Graph Database, I don't like it. Because why would a common person know it is the Wiz Graph Database, right? So it's making sure that every single thing you say is understandable by anybody. There's no reason to use complex terminology, when you can keep things straight and simple. **Lenny Rachitsky** (00:49:59): Easier said than done, but such a good reminder to always be, is there a framework here? Are you just trying to remember, people outside don't understand anything we are talking about, and simplify it further? **Lenny Rachitsky** (00:50:10): How do you actually practice that? Because I imagine everyone's, "Yeah, yeah, yeah, I know. I know all this stuff," but they don't actually do it. Is there any tips there, for how to actually practice this? **Raaz Herzberg** (00:50:18): I constantly remind myself about the bubble. Every time somebody says, "Oh, we haven't changed our color for so long, or a website's headline," a lot of those things, for me, it's like, you are the only one that is sick of it. **Raaz Herzberg** (00:50:33): Your customers are just learning what you put there 10 months ago. You are the only one looking at this thing, day after day after day after day after day. You're actually going to change it, only they're just starting to grasp it, and you're changing it under their feet. **Raaz Herzberg** (00:50:46): It's living in that bubble, and constantly reminding myself, it is a bubble. I'm in that Wiz bubble, right, but my audience is not. So yeah, it's a daily reminder. It's a hard daily reminder. **Lenny Rachitsky** (00:51:00): That is so funny. Okay, just a few more questions. One is, so there's four co-founders of Wiz. That right? **Raaz Herzberg** (00:51:08): Yeah. **Lenny Rachitsky** (00:51:09): What your relationship with them, how has that changed over the years, and over time? I imagine it's very difficult being, not a founder, trying to have a lot of influence on strategy and vision, and all these things. **Lenny Rachitsky** (00:51:23): Just, I guess, how has that relationship changed over the years? Anything there that might be helpful to folks, and any advice for people in a similar boat, to work well with founders who are also very product-oriented, and very opinionated about everything? **Raaz Herzberg** (00:51:38): Yeah, I think the Wiz founding team is a truly incredible team. They also have a very unique story. Wiz is actually their second company together. So before Whiz, they founded Adallom, which sold to Microsoft. **Raaz Herzberg** (00:51:51): That's how they all ended up in Microsoft in the first place. Even before that, they all worked together in the Israeli army, so they've known each other for, they've been working together for 30 years, right? **Lenny Rachitsky** (00:52:02): Wow. **Raaz Herzberg** (00:52:02): It's a long, long time. Well, not 30, I made them older, like 20, 22, 22 years. It's a very, very, very unique team, where there is complete trust between the team members. Each has his own clear domain, and that's why decisions are made super fast, super fast, because, the complete trust, and everybody has their clearly own domain. **Raaz Herzberg** (00:52:31): I think the unique thing about Wiz, and I truly think it defines their company's culture to this day, is exactly that they did not have to work hard, to be able to impact strategy, and get a seat at the table. **Raaz Herzberg** (00:52:45): I think that it's open, it's a very open culture, and an open company, that goes back to the beginning of being able to say, "I don't understand." **Raaz Herzberg** (00:52:53): They really believe in employees, and they really believe in giving everybody a chance to have impact. Regardless of title or experience or anything, if you want to drive more impact, you will get the chance. I think it's something I really learned to adore in that team. **Raaz Herzberg** (00:53:10): It's like, they will give their trust to someone, and they will allow you to try. And I think it also causes employees to have a lot of loyalty, because you are given those opportunities, and you are given that chance. **Raaz Herzberg** (00:53:24): It builds a very, very healthy culture, and I think, also, a culture that's very loyal. Everybody feels part of what's being built here. **Lenny Rachitsky** (00:53:32): Incredible. And how many employees are there? How large is Wiz at this point? Just for folks to get a sense, if they want to potentially join Wiz, some day? **Raaz Herzberg** (00:53:39): Around 1,000 through 500, probably. **Lenny Rachitsky** (00:53:46): Okay, awesome. Amazing. **Lenny Rachitsky** (00:53:47): Okay, well, potentially final question. I want to take us to Contrarian Corner. I'm curious if there's something you have a very contrarian opinion about, something that you believe, that a lot of other people don't believe? **Lenny Rachitsky** (00:53:59): We've already covered a number of things, I think, like that, but is there anything else that comes to mind? **Raaz Herzberg** (00:54:03): It's so funny, because I don't think we've covered anything contrarian. **Lenny Rachitsky** (00:54:05): Okay. **Raaz Herzberg** (00:54:09): I think one thing is, maybe goes back to what I was talking about before, but it was failing in confidence. I think at least, being a woman in tech, you get talked to a lot about imposter syndrome, and building up her confidence. I actually do think that my approach to it, at least for me, has been just more effective. I won't be able to build that confidence. **Raaz Herzberg** (00:54:30): I do feel like an imposter, and I know there's always those statistics about many people feeling that way. So I think, maybe just, "Let's embrace it. I feel like an imposter, you feel like an imposter, everybody feels like an imposter," It's kind of, maybe embrace it, but don't let that stop you from making a decision. **Raaz Herzberg** (00:54:49): Maybe they will find out you're an imposter, maybe let them find out. It's fine. If you think about trying to go to an interview for a company, and you start thinking, "Oh no, I won't get accepted, they won't take me," perfect. **Raaz Herzberg** (00:55:03): Let them not accept you. You think you're not good enough? Perfect. That's on them, to not accept you, right? Give yourself that opportunity. **Raaz Herzberg** (00:55:10): And I think, for me, maybe less talking about the imposter syndrome, more talking about just, "Okay, but ignore it. You will never know your limit if you don't try." **Lenny Rachitsky** (00:55:20): The best advice I've heard along these lines, which is basically what you're saying, is that when you take on a new role, you actually are an imposter. You've never done this before, and that's okay, and that's very normal. **Lenny Rachitsky** (00:55:32): Most people in a new role, when they're promoted, given a big opportunity, yeah, you are an imposter in many ways, but that's okay. And that's exactly what you're saying. **Raaz Herzberg** (00:55:39): I never heard it, but I love it. **Lenny Rachitsky** (00:55:42): Raaz, is there anything else you wanted to share, anything else that we haven't touched on, that you think might be helpful to folks, before we get to our very exciting lightning round? **Raaz Herzberg** (00:55:49): I deeply, deeply believe that we're doing something super special in Wiz, and I think the company is in such an interesting place of hyperscaling, but still keeping that authentic, and I think, flat and enabling culture. **Raaz Herzberg** (00:56:02): I think there's literally interesting opportunities across every domain. So yeah, just to say that we are always hiring for great people, trying to make an impact. **Lenny Rachitsky** (00:56:13): Are there any roles or areas you're specifically most focused on hiring now, in case folks are listening, you're like, "Oh, shit, I'm going to apply?" **Raaz Herzberg** (00:56:19): Truly, the beauty of hypersaling is, we are hiring across everything, but also, if you feel super strongly about joining, and you don't find the right role, we'd still love to talk to you. There's many, many things for passionate people to do here. **Lenny Rachitsky** (00:56:34): Awesome. We'll link to the Career page in the show notes. And with that, Raaz, we've reached our very exciting lightning round. Are you ready? **Raaz Herzberg** (00:56:41): I'm ready, I hope. **Lenny Rachitsky** (00:56:43): First question, what are two or three books that you find yourself recommending most to other people? **Raaz Herzberg** (00:56:48): So I focus like it was on the product side of things. We mentioned the heat in the kitchen. Actually, one of my most favorite business books, and I've read a lot of them, is probably Setting the Table, by Danny Meyer, which is, he owns Shake Shack, and a chain of really great restaurants in New York. **Raaz Herzberg** (00:57:07): And it's such an interesting business perspective, from a different domain, than obviously tech or SaaS. But there's so many applicable lessons there, from the deep connection to hosting, focusing and obsessing over your customer. Shake Shack, unlike other chains, where they optimize for you not to sit down, they optimize for you to sit down there. It's a very, very unique culture and unique vision, and I've learned a lot. Some of the most memorable lessons come from his management thoughts. **Raaz Herzberg** (00:57:39): Imagine huge chains, but also very high-end restaurants. I think it's a very, very inspiring, inspiring book, and different, just different from my domain, but very applicable in my domain, as well. **Raaz Herzberg** (00:57:50): And then, a second book I really like, I read it early on in Wiz, and so did the entire founding team, I think, the book by Netflix co-founder Reed Hastings, No Rules Rules, which also, I think, talks very clearly. Netflix has a super unique culture and story, right? **Raaz Herzberg** (00:58:11): Talk about pivots, they sold cassettes over mail, and somehow pivoted to what it is today. That's an insane story. Think about pivoting from a tech company, to a company that has production to do, and produces reality TV. Talk about the type of culture you would need to truly pivot, I think it's a super interesting read for anybody thinking about putting strong culture in place. **Lenny Rachitsky** (00:58:34): I'm going to call an audible, and ask about marketing, specifically. You said that early on, you read some marketing books, and listened to marketing podcasts. Is there anything else that you recall was very helpful, in helping you ramp up in this world, and do marketing? **Raaz Herzberg** (00:58:48): Honestly, I think, at the end, for me, I just ended up saying, "What are the companies I feel do things really well? What are the brands I love, and what do I love about them?" **Raaz Herzberg** (00:59:04): And then, really obsessing about, what did they do, what are their team doings? And then, also, obsessing about the people behind them. For example, I think Gong does an amazing job in marketing, for a B2B product. **Raaz Herzberg** (00:59:22): So it was like, "Okay, so what are all the things Gong did?" Then I would look up every single talk their CMO gave. So it's like, I always backed up into it. I did not care if it's a security company or not a security company. **Raaz Herzberg** (00:59:35): I actually don't like the way most security companies market things. It's mostly by frightening and fear, and I don't like it. For me, it was just looking at brands I love, and then backtracking from there. **Lenny Rachitsky** (00:59:49): I love that. We have the CPO of Gong and co-founder coming on the podcast very soon, so I'll ask him about this. **Raaz Herzberg** (00:59:53): Oh, cool. **Lenny Rachitsky** (00:59:55): All right, next question. Do you have a favorite recent movie or TV show you really enjoyed? **Raaz Herzberg** (00:59:59): Honestly, I hardly, hardly watch anything. I think The Wire is the best show ever created. **Raaz Herzberg** (01:00:05): I will take that fight with anybody. But yeah, I haven't really watched anything super recent. **Lenny Rachitsky** (01:00:11): The only problem with the Wire is it's so long to watch. I've watched, I've seen it, I love it, but it's a large commitment. It's an hour times 22 episodes times, I think, five seasons, but worth it. **Raaz Herzberg** (01:00:22): Worth it. **Lenny Rachitsky** (01:00:24): Next question, do you have a favorite product you've recently discovered, that you really love? **Raaz Herzberg** (01:00:28): It's a funny question, in the world we live in, where there's just so many similar things. **Lenny Rachitsky** (01:00:32): That's why. Which one should we pay attention to? That's the question. **Raaz Herzberg** (01:00:36): I'll answer a pretty random answer. **Lenny Rachitsky** (01:00:38): Yeah, okay. **Raaz Herzberg** (01:00:38): Recently, I always go around with a notebook and a pen, still that type of person. I mean, I constantly walk around with them, across office rooms, blah, blah blah, and I always care deeply about the notebook and the pen. **Raaz Herzberg** (01:00:50): I'm a very picky person. I pick pens, I pick notebooks, and I often lose my pens, which is sad. I recently bought this cute something, it's very geeky, like, a pen holder for a notebook. I did not know they existed. **Raaz Herzberg** (01:01:04): It's a very nice feature. It's small, magnetic, and it claps into your notebook, and then you can put the pen in it. Really nice feature. **Lenny Rachitsky** (01:01:10): How does one find this? Is there a brand, or a name, or something? **Raaz Herzberg** (01:01:14): I'll send you a link, but if you look, "notebook pen holder," you'll find a ton. **Lenny Rachitsky** (01:01:18): Okay, cool. We'll link to in the show notes, whatever one you recommend. **Lenny Rachitsky** (01:01:22): Just a couple more questions. Do you have a favorite life motto that you often come back to and find helpful, in work or in life? **Raaz Herzberg** (01:01:29): I think, keeping it simple. If you start feeling like something is too complex, or an answer is too complex, or something you're building in the product is too complex probably, or something in your life feels too complex, probably, it does mean something. But sometimes, you just have to maybe take two steps back, leave it there, until you come back to it again, and you find a simple way out. **Raaz Herzberg** (01:01:50): Whether it's a private feature or anything, I feel like, if something starts getting too complex, and you don't know how to design it, or how to find end from start, it does mean it's not the right solution. It's too complex, it's not the right solution, but sometimes, I take two steps back, and you find it applicable to anything in life, almost. **Lenny Rachitsky** (01:02:08): Reminds me of the story when you were trying to sell the initial version of Wiz/beyond whatever it was called, early on, and it was just too complicated. No one understood what the hell's going on, and so I love how that circles back. **Lenny Rachitsky** (01:02:20): Final question. I know you can't talk too much about this, but I'm also just curious what you're able to share. As I said, allegedly, a company whose name rhymes with Loogle, wanted to buy you guys for many billions, and you all decided to decline that, and stay private. Anything you could share there, about maybe why you decided to do that, if that was true at all? **Raaz Herzberg** (01:02:40): Yeah, I mean, I can't address any specific offers. Obviously, Wiz over the years has gotten many acquisition offers. I can share, that I think for us, us being the founding team, the employees, the customers, the board, staying on an independent path, we all really believe that Wiz can become one of the biggest security companies in the world. **Raaz Herzberg** (01:03:06): When you look at Wiz today, and I mean, we spoke about the unconventional growth, when you think about it, in some ways, Wiz addresses the biggest growing market of security. Cloud security, cloud is the fastest growing, cloud is such a fast-growing market. Cloud grows 20, 30%, year over year. **Raaz Herzberg** (01:03:25): We feel like everything is in the cloud, but in reality, by estimation, only 20%, 15 to 20% of the infra today, is in cloud. It's a really, really fast-growing state, in a fast-growing market. And security by nature is a bit of a market of leaders. **Raaz Herzberg** (01:03:42): I mean, it's a bit like buying insurance for something. You want to buy it from the best, from the leader in this domain. And today, Wiz really is that leader, because it's a new space. Wiz is considered, I think, in many ways, and that is also what makes marketing and brand, not just marketing, but truly, brand so important. **Raaz Herzberg** (01:04:01): Wiz is considered, I think, the cloud security company, in a lot of ways. Still, of course, it's our to lose. There's a ton of work ahead of us, but that is a huge opportunity in front of us, becoming the cloud security company. And I think nobody thinks we are anywhere near ready to give it up, in a way. **Lenny Rachitsky** (01:04:21): I totally understand that, and again, Wiz is hiring, in case you are inspired by what you're hearing. **Lenny Rachitsky** (01:04:27): Raaz, this was incredible. I'm so happy that you did this. Thank you so much for being here. **Lenny Rachitsky** (01:04:32): Two final questions. Where can folks find you online, if they want to reach out, and maybe follow up on stuff? And how can listeners be useful to you? **Raaz Herzberg** (01:04:37): Find me on LinkedIn, and yeah, no apply. We'd love great people who are learners, which I think is what this podcast is all about. So definitely, the right place to find the right people. **Lenny Rachitsky** (01:04:48): Awesome. Raaz, thank you so much. **Raaz Herzberg** (01:04:49): Thank you so much for having me. **Lenny Rachitsky** (01:04:52): Bye, everyone. Thank you so much for listening. **Lenny Rachitsky** (01:04:56): If you found this valuable, you can subscribe to the show on Apple Podcasts Spotify, or your favorite podcast app. Also, please consider giving us a rating, or leaving a review, as that really helps other listeners find the podcast. **Lenny Rachitsky** (01:05:09): You can find all past episodes, or learn more about the show at lennysodcasts.com. See you in the next episode. --- ## [11/17] Behind the product: Replit | Amjad Masad (co-founder and CEO) **Amjad Masad** (00:00:00): The idea behind Replit is that making software today is very difficult. We want to make it easier. People view this as a developer in their pocket essentially. We have 34 million users globally. There's people everywhere learning to code on Replit, building startups, building personal software, personal tools. **Lenny Rachitsky** (00:00:20): For people building products, say, product managers, founders, what skills do you see will matter more, matter less? **Amjad Masad** (00:00:27): Typically, you're bottlenecked where your ideas are not fitting in because they need to be made and they need to be made quickly. Now, you open up that bottleneck. So now actually making things is a lot easier. Actually, you become limited by how fast you can generate ideas. **Lenny Rachitsky** (00:00:44): I think people are unaware of just how far things have gone. **Amjad Masad** (00:00:47): I could imagine whatever five years from now, someone running a billion-dollar company with zero employees where it's like the support is handled by AI, the development is handled by AI, and you're just building and creating this thing. **Lenny Rachitsky** (00:01:01): Man, the future is wild. Today, my guest is Amjad Masad. Amjad is the co-founder of Replit, an AI-powered software development and deployment platform for building and shipping software. It's one of the fastest-growing developer communities and AI products in the world. There's a lot of talk these days about how AI is changing, how products will be built, how product teams are going to operate, which functions will be more and less valuable over time. But I feel like very few people have actually seen what modern AI tools can do and have fully grasped how much you can get done with very little technical skill now and in the future. And so I'm going to do an experiment with this podcast where I'm going to do a series of behind the product episodes where we go deep on important products that product builders should be aware of and should probably start playing with. **Amjad Masad** (00:02:46): It's my pleasure. **Lenny Rachitsky** (00:02:47): I thought it'd be great to start with just having you explain what is Replit? What's the vision? Where is this going? What job does it do for people? **Amjad Masad** (00:02:56): The idea behind Replit is that making software today is very difficult and we want to make it easier. One of the reasons for the difficulty is that it is very fragmented, so you would need to download what's called an IDE. It's basically a code editor. You need to download the runtime, basically Python or JavaScript, need to figure out a package manager to configure your kind of open source packages, and once you've done all of that, you need to figure out how to deploy it, how to share it. So it's a very hard process, and that's one of the ways where people get stuck and never learn how to code because it just feels like this cumbersome IT process. **Amjad Masad** (00:03:42): And so the vision for Replit has always been is like, okay, making software is fun, is great, more people should do it, but so for more people to do it, it needs to be easier to do, it needs to be in one place, and it needs to be learnable. It's easier to learn. So that's the product today. It is I think one of the more easier IDEs/ environment/deployment environment on the internet, and I think we make it really easy for people to just jump in even without prior experience of coding, especially now with the new AI products that we built. **Lenny Rachitsky** (00:04:22): **Amjad Masad** (00:06:55): We have 34 million users globally. We have a large global presence. There's people everywhere learning to code on Replit, building startups, building personal software, personal tools or internal tools of the companies. More recently, we've been expanding to companies. We released our kind of B2B package in July, and that's been growing really fast. It's been really fun to see people bring Replit to work as well. **Lenny Rachitsky** (00:07:25): Damn, I knew it was popular. I didn't realize it was that large actually. As I was preparing for this podcast episode, there's this tweet that went viral where this guy, Jevin, who I actually know. I know this guy from Canada, he's awesome, tweeted about how his 11-year-old girl built an app in Replit. She just had an idea and she built it. And the best part of it is someone in the... replied to him and they're like, "You have to launch an app. You have to host it somewhere. You have to build a database. You have to deploy it. There's no way to do that." And he's like, "No, that's exactly what Replit did." **Amjad Masad** (00:07:59): Yeah, that's what we do. Everything that commenter was talking about, and he's right. The surprising thing about an 11-year-old building an app is not so much even the coding, it is like all the nonsense around it, and so we just abstract all that away. **Lenny Rachitsky** (00:08:19): I love that and I struggled with that myself when I was an engineer way back in the day. **Amjad Masad** (00:08:24): Oh, you were an engineer. I didn't know that. **Lenny Rachitsky** (00:08:26): I was. I was an engineer for 10 years. I was an engineering manager, and then I jumped ship into product. **Amjad Masad** (00:08:31): Wow. **Lenny Rachitsky** (00:08:32): I'm happy I did but I do miss that. I was not an amazing engineer. I was a good enough startup engineer, so this is the kind of stuff that I would've left to use. So we're going to jump into a demo of what this actually looks like. I thought maybe actually before we get into it, there's other tools that people are aware of that help you build stuff. And so to put a finer point on what this does and how it's different from other things, you may have heard of, say, Cursor, it comes up a lot these days, just talk about a little bit about the competitive landscape of who else is out there that helps you build product. **Amjad Masad** (00:09:04): Again, we go back to this idea of end-to-end platform for making software. So that's from writing code all the way to deploying it, and monetizing it and all of that. Now, every step in the process of the software development lifecycle, there are a lot of different tools. So Cursor is a fork of VS Code that's made that has really awesome AI tools, but that's an editor. You still need runtime, you still need a deployment environment. Actually, quite a few users use Cursor in tandem with Replit, because Replit just simplifies the runtime and deployment environment. **Amjad Masad** (00:09:42): And so you have products, AI products, different places in the software development lifecycle, but really what differentiates Replit is that we do everything, but also that makes it harder to adopt for certain people. If you're at a big company, it's very easy to bring a new editor and start coding with it. It's quite hard to bring something that's quite opinionated about everything from how the code runs to how the code deploys, but that's the trade-off we're willing to make is like yeah, we're not going to get into the enterprise main software development pipeline, but we want to empower everyone to be able to build software, and that means product managers, designers. We have operations people, sales ops, HR ops. We have lawyers using Replit, and so it is democratizing the act of software engineering. **Lenny Rachitsky** (00:10:49): Amazing, and that's why you're here. Let's do a demo. While you're pulling it up, you're going to share your screen and show us what this product can do. And the reason I am excited about doing a demo, and this is an experiment, kind of a new type of podcast episode I'm doing where we're diving into specific products and what they can do, I feel like there's so much talk about AI and what it's doing and people keep reading about, oh, AI can do this and AI can do that, and I feel like not many people actually see this stuff in action, especially the most cutting edge stuff. I think people are unaware of just how far things have gone and how much is actually possible, especially when someone that knows what they're doing is using the product. So I'm excited to show people what is actually possible and especially because this is going to impact the future of product management and product teams. So I'll turn that over to you. Give us a demo. **Amjad Masad** (00:11:37): Awesome. So this is Replit's homepage. You can create what's called a Repl, which is a project. We have all sorts of languages. You can pick from really in the hundreds, but most recently, and this is how Replit became a thousand times easier, is you can just describe what you want to make. So you go on this home page, we have this text box, and you can write something like make me a cool app or what have you, but a more descriptive prompt is better. **Amjad Masad** (00:12:11): And so I asked RPM at Replit, Aman Mathur who's a fan of the show to tell me what PMs like to build. And so he came up with a prompt. He kind of really crafted a great prompt. So I'm going to put it here. And basically, what we're asking for is we want to build a web application. You can say what stack you want to use or you can leave it up to the AI to decide. Here we're saying build it in Node.js for product managers to track feature requests on a public dashboard. So say I have a product, I'm growing, I have a community, I want that community to engage with building the product. I want them to submit feature requests, vote on them. I want to be able to manage that. So we're talking here about the features of voting system, feature requests. **Lenny Rachitsky** (00:13:02): Read a few of them just for folks that aren't watching on YouTube to give them, send some of the stuff in this prompt. **Amjad Masad** (00:13:07): So a feature requests submission, so allowing the users to add features. A voting system, so allowing users for these features, feature requests and status tracking, being able to, it's like a kind of advance style board with columns like planned and progress, so that way the admin can kind of share with the community what they're building. And we want it to be user-friendly design, so make it modern and all of that nice kind of prompty things. And then admin controls for product manager. So as a product manager, I want to be able to really manage this community. **Lenny Rachitsky** (00:13:44): I love that it builds internal tools too, not just the front end. **Amjad Masad** (00:13:47): Yes. Exactly. Exactly. All right, so we're going to start building. Since this is a pretty big, big prompt, the initial coding might take a while. There's different styles of using Replit agents. I often go with minimalist prompts. That's also how I code as well. I have a vague idea for what I want to build and iterate from there. Other people, product managers like to write PRDs and more descriptive things, and you can do either of those things. The AI now responded and then said, I'll build all of that for you. I'm going to build up the initial prototype and you can tell me how it feels, and then we can make it better from there. The AI is also suggesting, adding comment threads, implementing email notifications, and so I can select those and it's being creative, it's telling me what else I could build, but for now, I'm just going to go with a prototype and then we can assess from there. **Amjad Masad** (00:14:50): So as you see, as the prototype is starting, you can see this progress pane where we can watch the AI doing its thing here. It's created a Postgres database. Obviously, when we're building a full-stack application, you need to be able to save things. This is one of the cool things about Replit. We have all these services, storage, database. So now it's coding, it's building the database schema. Now, it's building the home page, and it's actually quite fun and edifying to watch it build this, because you can really start to learn how to structure web apps. And if it runs into a problem and as things get complicated, it might run into a problem and you want to be able to help debug and things like that, it's good to be able to have an idea of what's going on, but it's not necessary. I think a lot of people just don't care about the code and are still able to build things, but we want to make the process transparent. We want to show people exactly what the agent is doing. **Lenny Rachitsky** (00:15:57): You're basically sitting there behind an engineer on a computer and just watching them code is what the experience feels like. **Amjad Masad** (00:16:04): Yeah, and actually, the way we built it is it's a multiplayer system. So Replit has real time, what we call multiplier coding, and we reused the multiplayer system to build the agent. So the agent in the code is structured as another user of the platform. So basically, we're both coding together. So I can go into the files here and that's the thing that makes Replit really cool. I think people are familiar with some of the more chat interfaces like v0 and others where it's purely chat, but this is a full IDE where you can go and look at the files and edit them yourself or ask the AI for an explanation. **Lenny Rachitsky** (00:16:51): What's the limitation of what this can do today? What can't you do? Say you're like, you have zero coding experience, what sorts of products can you not yet build with something like this that might be possible in the future? How far does this take you now? **Amjad Masad** (00:17:08): You can build MVPs. I think you can also start to get some initial users. I think when you start iterating on the product like large iterations, you might run into problems. For example, it's not very good at database migrations, and so we're trying to fix that. So when you're iterating on the product, a lot of the times, you're actually changing the structure of the app and that requires database migrations. And so now it might change the database in a way that creates an error that's unrecoverable. And at that point, you might get stuck, especially if you don't know how to code. **Amjad Masad** (00:17:56): Some people will figure it out by going to ChatGPT and Claude and asking questions and I actually am really inspired about how persistent some of our users are, which is really amazing. But I think you'll get an MVP pass, the MVP where it's a product that's working and you need to change and iterate on it. It's still a struggle now, but I expect over the next few months, we'll continue. It's if you think about it's like we're building as you were building, so we're building out the agent so that it can continue getting better as our users are also building their applications. **Lenny Rachitsky** (00:18:40): Got it. So what I'm hearing is it's really good at building the first version and helping you get to something that you can even have people use. It's not amazing yet evolving from there, using AI to help you make the product better and better and better and iterate. **Amjad Masad** (00:18:55): Yes. **Lenny Rachitsky** (00:18:55): But you can get in there if you know how to code and take it from there, right? **Amjad Masad** (00:19:00): Yes or you can hire someone. We have a feature on the site called Bounties where you can hire human coders to kind of help you finish. **Lenny Rachitsky** (00:19:14): That's going to be our job for humans. That'll remain for a while. **Amjad Masad** (00:19:18): You know what we want to do? We want to get to a point where the agent can go grab a human when it runs into a problem. I think that would be sick. **Lenny Rachitsky** (00:19:32): Oh, my God. It's like everything's reversed. I love it. Oh, I think it might be done. Check that out. **Amjad Masad** (00:19:38): Yeah. So now the agent is asking us, is the application running and showing the homepage? **Lenny Rachitsky** (00:19:46): Like it's confirming. **Amjad Masad** (00:19:48): Yeah, almost asking us to do a QA. I'll just say yes. So it found an error. So there's an error here and it's like there's a dumb warning, "I'm going to fix it." So in the meantime, as it's fixing it, so it can be proactive, right? Because it looks at all the errors and things like that, but in the meantime, we can use it. I just created an account. It's coding. **Lenny Rachitsky** (00:20:12): [inaudible 00:20:12] It's cool. **Amjad Masad** (00:20:11): Let's see how it restart. Okay, we'll wait for it. **Lenny Rachitsky** (00:20:16): How long would you say it would take an engineer to build this? A typical engineer? **Amjad Masad** (00:20:22): A few days, I would say to a week. I mean, if you're really good, it might be hours but it probably would take me a few days. I would say I'm like decent engineer, it'll take you a few days. **Lenny Rachitsky** (00:20:40): And it took how much? 5 to 10 minutes. **Amjad Masad** (00:20:43): Yeah, and it probably cost us something in the sense. **Lenny Rachitsky** (00:20:50): Wow, in terms of compute. **Amjad Masad** (00:20:52): In terms of compute, yeah. Probably, I would estimate it like 15 cents or something like that. **Lenny Rachitsky** (00:20:58): Wow. Okay, so here it is. **Amjad Masad** (00:21:01): Here it is. And the agent was like, "Okay, this is looking good, completed it if you want to deploy it." But I'm like, "Okay, I'm going to test it first." **Lenny Rachitsky** (00:21:09): And so currently, it's living just locally on your local host. **Amjad Masad** (00:21:13): Yeah. It's not local host, it's on a Replit but yes, it's the equivalent of local host. Because it's really easy, I can even invite you to this session. You can be here with me and so it's all online. **Lenny Rachitsky** (00:21:26): Got it. **Amjad Masad** (00:21:26): So let's submit a feature. So make the product prettier. That's what a typical user might say. So we have this here, you can upvote it. I guess I can't upvote it because I'm the user that created it, but created another user. You can upvote it. But now we need to be able to move things around as the admin, so I don't know how to log into the admin panel. So I'm going to ask the agent, how do I log into the admin panel? So it might've already built the feature, and it's not exposed in the right way. It'll be able to [inaudible 00:22:08] **Lenny Rachitsky** (00:22:08): What I love about just watching you interact with this thing, and just real quick throughout, it feels like an engineer that is behind the scenes building this thing like on Slack and you're just talking to them. They built this thing, they're like, "Check this out, I'm done." And you're like, "Oh, okay, about how do I log into this admin panel?" And they're like, "Okay, here we go." **Amjad Masad** (00:22:26): Yeah. So it says, "Would you like me to help you register account?" So it's creating an account, an admin account for me. So it's not only builds things, it also maintains things. In this case, it's actually doing SQL queries. It's not writing code to create an admin account for us. **Lenny Rachitsky** (00:22:51): It's insane. I want to talk about the implications of this on product development and product management and founders, but what we just witnessed is somebody, I know you do have technical abilities, but someone that didn't have to have any technical skill, build a real product that people can use in five minutes that looks good and works, and you could keep making it better by talking to this agent. **Amjad Masad** (00:23:17): I'll tell you from our experience what we're seeing, there's so many products that are empowering developers. It's a very easy calculation to say We're going to make engineers 20% better and we're going to sell it to companies and we're going to take 10% of that value, right? That's why there's so many startups now that are just trying to make engineers a little better. Our calculation is like, well, what if you made everyone developer? What does that look like? And so when we released agent and really made programming a lot easier, what we're seeing is that people, exactly like you said, people view this as a developer in their pocket essentially. What we're hearing from customers is that I'm doing things I would otherwise have to go hire a developer, but also because the activation energy is lower than going to hire developer, whether Upwork or other places, I'm building a lot more ideas that otherwise I wouldn't have built. **Amjad Masad** (00:24:26): I think it was it called the javelin's paradox or something like that, which is when the cost of things go down, the total consumption of it goes up, which I'm not sure why they call it a paradox, but the cost of electricity goes down, maybe you would expect that the total spend goes down, but actually total spend goes up because people consume more of it. And so I think that's going to be the case of software. As the costs go down, people will just make a lot more software to improve their lives and to improve their work and start more startups and all of that. **Lenny Rachitsky** (00:25:05): So to follow that thread, what are you seeing inside of startups or even big companies in terms of how folks are already using this knowing this is the worst it will be and it will only become smarter and better these days? How are people actually using this that are say product managers or just non-technical people within startups or bigger companies? **Amjad Masad** (00:25:26): On the SMB side of things, a lot of people are building kind of back office tools. So we have real estate agents that have a lot of data, have a lot of things they want to manage in their business that building a lot of these tools, that they otherwise would have to buy, but typically when you buy, it's actually not exactly what you need. And that's kind of the problem with SaaS, like one size fits all. And so a lot of people are seeing it as sort of a SaaS replacement for in-house tools and things like that. And then when you go to the bigger companies, it's anywhere from prototyping to actually production apps to tools as well. So we've seen product managers build, like I said, like a v1 of an app and actually go out and test it with users. I can't name the company, but there's a public company that have used Replit to test a v1 of an app. **Amjad Masad** (00:26:35): And obviously after that sort of works, they take it to the engineers and they're like, "Okay, we built this thing. We think it's a great thing. We test it with some users. Let's go actually put it on the roadmap and build it into the actual product." So you are instead of unblocking product managers from having to need engineers for everything that they want to build so they can really build the v0 or v1 of the product. **Amjad Masad** (00:27:04): And that's super empowering for them. We saw it also with marketing departments like SpotHero has a head of marketing that actually can code decently well but use Replit to build these apps, and they built a competitive analysis application that looks at a competitor's pricing and makes sure that they're benchmarked correctly. And so it's a full stack app use database and everything and it runs on a continuous fashion. And we see sales engineers use Replit to spin up prototypes really quickly. So actually someone at X, formerly Twitter is on the partner engineering side of things, and he uses Replit agent to spin up applications and prototypes for customers to see how they can use the X API. **Lenny Rachitsky** (00:28:06): I love this. I love these examples. By the way, the demo, is there anything else you want to share about the demo before we close that out? **Amjad Masad** (00:28:14): So it created an admin account. We can ask it with the username, password and kind of go into it and manage it but basically that's it. The app's complete in terms of what we ask for. We can send it out. I can give you a URL. Let's actually just deploy it really quickly to show people how you can deploy. **Lenny Rachitsky** (00:28:35): Maybe the show notes, we'll link to the app, you could check it out. **Amjad Masad** (00:28:38): Sounds good. **Lenny Rachitsky** (00:28:38): Okay, cool. That's amazing. So this is deploying it onto some cloud provider. I don't know what you use, but... **Amjad Masad** (00:28:44): We use Google Cloud. So we abstract all of that away from you, but we use Google Cloud behind the scenes. **Lenny Rachitsky** (00:28:52): Imagine a place where you can find all your potential customers and get your message in front of them in a cost-efficient way. If you're a B2B business, that place exists, and it's called LinkedIn. LinkedIn Ads allows you to build the right relationships, drive results, and reach your customers in a respectful environment. Two of my portfolio companies, Webflow and Census, are LinkedIn success stories. Census had a 10x increase in pipeline with a LinkedIn startup team. For Webflow, after ramping up on LinkedIn in Q4, they had the highest marketing source revenue quarter to date. **Lenny Rachitsky** (00:29:26): With LinkedIn Ads, you'll have direct access to and can build relationships with decision makers including 950 million members, 180 million senior execs and over 10 million C-level executives. You'll be able to drive results with targeting and measurement tools built specifically for B2B. In tech, LinkedIn generated 2 to 5x higher return on ad spend than any other social media platforms. Audiences on LinkedIn have two times the buying power of the average web audience, and you'll work with a partner who respects the B2B world you operate in. Make B2B marketing everything it can be and get $100 credit on your next campaign. Just go to linkedin.com/podlenny to claim your credit. That linkedin.com/podlenny. Terms and conditions apply. Let's go down this thread actually while this is happening, just like what allows for this to be possible technology wise? What is the stack? Whatever you can share that enables this to exist. **Amjad Masad** (00:30:26): Yeah, for sure. First of all, it's all the abstractions that we built. So the way a Replit works is the very bottom layer. It's our runtime. So this is the operating system, this is the package manager, this is the language runtimes. We built a system that is able to install packages in any language, including native packages. So the AI, anytime, it needs a package. I can go here and show one of those. By the way, the AI can take screenshots as well so that it checks it works. So here you can see it is taking screenshots to make sure that the homepage is rendering. Here, you can see it wanted a drag and drop library, and so it installed that. And so it has access to all the packages across all languages, including Linux and all of that. And then the layer on top of that is the editor and the infrastructure that runs the editor, including what I described as the multiplayer editor. **Amjad Masad** (00:31:33): And then we expose all of that infrastructure to the AI. And there's almost like a new discipline called AI Computer interfaces. So sort of like HCI is now a ACI and turns out LLMs need interfaces that are actually quite different than humans. They're trying to make them use human interfaces like Anthropic's computer use, but those are really expensive and you need to process all this images and video. So instead, for the shell for example, we give it sort of a text representation of what the shell is doing at a certain increments for package installation. We give it a certain tool for editing. We give it an editor tool that when it's writing the code, it's getting feedback on whether there are errors or not, similar to what a human sees, but it's actually old text just to make it easier. So that's AI computer interface, and obviously, all of that is sitting on foundation models. So the improvement in foundation models has allowed us to build this. **Amjad Masad** (00:32:51): The most important model that we use is the Sonnet model from Claude, from Anthropic, and it is the best model at coding. So that's the model we use for coding, but we use models from OpenAI as well because a multi-agent system. And so we have models that are critiquing. We have manager editor model, and we have a critique model and different models will have different powers. We also train some of our models, like the embedding model for search is something we trained internally. So I actually wrote about it back in '22. I said it's going to be society of models, like products will be made of a lot of different models, and it's quite a heavy engineering project. **Lenny Rachitsky** (00:33:47): To say the least. We were talking offline and you said you've been working on this since 2009 when you first built the first idea of Replit. Is that right? **Amjad Masad** (00:33:56): Yes. **Lenny Rachitsky** (00:33:58): Oh, my God. **Amjad Masad** (00:33:58): Here's the deployed app. I can send it to you and you can use it and you can see my request even on the logged out page so I can register, upload it, and log in as admin and move things around. We can see what's in progress, what's completed. **Lenny Rachitsky** (00:34:14): This looks like a product. I could see designers spending days designing, passing it to engineering, PMs, having feedback, engineers taking a few days to build it. **Amjad Masad** (00:34:26): Yes. **Lenny Rachitsky** (00:34:27): And here's just a prompt, here's what I want. **Amjad Masad** (00:34:30): That's right. And we can iterate on it very easily. We can also iterate on the UI. We can say, I don't like this or that, and it'll do a good job. So we can go here, we can start a new session or a new session to create an entirely new feature here, and it'll just do the right thing. **Lenny Rachitsky** (00:34:47): And it builds from that code base. It understands here's what you've built. I want to add this thing. **Amjad Masad** (00:34:52): Yes. **Lenny Rachitsky** (00:34:52): Okay. **Amjad Masad** (00:34:53): And that becomes your history, right? This was the v1 and now I'm working on this new feature, and it's almost like what engineers do in Git commit messages. By the way, it generates Git commit messages for everything that it does so you can roll back as well. And so we're trying to make it so that yes, it's for everyone, but we're trying not to abstract too much away. We want to build tools for you to learn to use. And so we want power users to be able to understand the full power of Replit and it is really deep product. I think you can spend a couple of years to kind of master it. **Lenny Rachitsky** (00:35:40): I want to talk about implications, but I want to come back to something you mentioned that is incredible that people may have missed. You basically built a computer specifically designed for the AI agent to use that is a different version of a computer specifically optimized for how AI wants to use a computer. **Amjad Masad** (00:36:00): Yeah. So there's an entire discipline called like HCI, right? It's like how do you do that- **Lenny Rachitsky** (00:36:07): Human-computer interaction. **Amjad Masad** (00:36:08): Yeah. So now there are papers about AI computer interfaces and interactions. And so large language models are trained on large stacks of corpus from the internet, but they're still kind of alien creatures. So they're not like humans, so they have different behaviors. It's unclear what's the best way to give it an editor. So there's so many experimentation about what's the best way to give it a view on what's editing, how many files can you show it before it starts to hallucinate. And right now, it's more of an art than science, but it's becoming more and more like a science. **Lenny Rachitsky** (00:36:55): This is insane. So it's a simple way to think about it. There's this foundational model, here's what I want you to build, and here's a computer to use to build it. **Amjad Masad** (00:37:05): Yes. **Lenny Rachitsky** (00:37:05): How am I [inaudible 00:37:07] **Amjad Masad** (00:37:06): Here's a computer with a set of tools. Here's a tool to install a package. Here's a tool to edit the code. Here's the tool to run a SQL query and also services. Here's a bunch of services you can graph from. Here's a database service, here's an object source service, here's an auth service. So you can think about it as a bunch of external services, the computer with a bunch of tools, and they're all interfacing with the foundation model. **Lenny Rachitsky** (00:37:38): It's funny listening to this how, it starts to feel like the fact that we might be living in a simulation is not as far-fetched as it may feel. Like this feels like the beginnings of what a simulation computer would be. **Amjad Masad** (00:37:50): Yes. You can go really Sci-Fi on this and it's like where is it headed, right? **Lenny Rachitsky** (00:38:03): Yeah. **Amjad Masad** (00:38:03): If we give it enough tools, let's say, I can drop it in Slack and instead of interfacing with it in this fashion, I want to interface with it in a totally autonomous way. So we actually have this feature coming up where instead of me testing it, we give it another agent. So here, instead of me interfacing with it and saying this is running or not running, we can give it another agent that is actually testing the application and then let's say interface with it entirely through Slack. And I'll say something like, give me Taylor Swift tickets the moment they land. **Amjad Masad** (00:38:49): And so it'll build an app that continuously monitors the web for when Taylor Swift tickets land and there's an agent that's using the app to be able to get that. And you can imagine it has some kind of wallet or credit card. And then the moment it lands, it gets it. What I'm trying to say is that software, like agents being able to do software, is how AI gets more general because software runs our lives, runs the internet, runs our businesses. And so the more competent AI becomes that software, the more general they are in terms of what they can do. **Lenny Rachitsky** (00:39:36): Okay, this can go in so many directions. I'm going to bring us back to the implications for people building products, say, product managers, founders, how does this change, that function, that skill set? What skills do you see will matter more matter less? Which functions are maybe in some danger and they should start thinking about a different career path? **Amjad Masad** (00:39:59): One interesting persona that we're seeing is the CEO, the CEO of startup. Andrew Wilkinson from Tiny is a big user. And so these people are typically creatives. They built a company, they hired people. A lot of them can't code. A lot of them are designers or product managers or something else. And you can imagine a bottleneck, you can imagine a bunch of ideas in their head, and the ideas have to translate through them talking. And then someone else listening to them and assuming that someone else actually understands what they say, and then that's someone else going and trying to build what they want to build. And also assuming that person has time, because a lot of times, your engineers are kind of stuck building the current thing. They're not thinking about the future thing. And so what gets me excited is a lot of these CEOs are building the future concept, the next product they're going to build, the next, say, company they're going to build. **Amjad Masad** (00:41:08): And so it unlocks the creativity and again, sort of unblocks them from that. And look, it's a v1 of the product but it can push things forward. You can touch it, you can feel it, you can say, okay, this really has lags and we should work on it. You give it to your engineers and they can improve on it from there. So that's one persona but I'm really excited about it, the CEO/founder. In companies, one of the things that I think is sort of hard about tech companies is these silos between designers, product managers, and engineers. And everyone feels that pain of, we have low bandwidth communication, which is language and then text on Slack and Zoom calls. And it leads to a lot of frustration, because it's really easy to misinterpret people and again, leads to siloing where people working on something, and then you pass it on to the next team and it's not really what they expect. **Amjad Masad** (00:42:30): That happens a lot between designers and engineers, but the common language that everyone shares is code. Ultimately in software tech companies, everything that we're talking about need to eventually flush out in terms of code. And so what if the language becomes actually working prototypes and working applications? For example, we have a Figma extension that translate Figma mocks into React that runs on Replit. So instead of giving the engineers just mocks or screenshots, whatever, you just say, oh, here's a bunch of React code, just make sure it runs on our infrastructure but don't mess with it, don't move the pixels around. And so I think it just opens up silos of the companies, make communication around product a lot more concrete, because I can give you a working prototype and that'll change how people work, if you can imagine that everyone can make software. It's really kind of a radical reimagining of not just what tech companies are but really what most companies are because everyone can be more general. **Lenny Rachitsky** (00:44:04): So say you're a PM listening to this, an engineer or designer, what skills do you think if you were one of these folks? If you were in building Replit right now, what kind of skills would you suggest folks focus on more and would you think are just like, okay, this can be less valuable in the future, don't worry about these sorts of things? And you can either pick one of those three functions or all three. **Amjad Masad** (00:44:25): I think a very important scale that's perhaps harder to develop but it's worth working on is being generative, being more generative, being able to generate new ideas quickly, because you can think about it as a factory line. So you have ideas, you have the production of these ideas or the initial production of these ideas, and then you have other people that want to consume these ideas or work with you on these ideas. And so typically you're bottlenecked by the middle part where your ideas are kind of like they're a lot of them and they're not fitting in, because they need to be made and they need to be made quickly. And so now you open up that bottleneck. So now actually making things is a lot easier. Actually, you become limited by how fast you can generate ideas, and I find that true of myself as well. I consider myself quite generative, but now I have this tool and I can build a lot more and explore a lot more and I'm finding that, well, actually, I'm running out of ideas sometimes. **Amjad Masad** (00:45:53): So training that muscle I think is a good thing. I think learning a little bit of coding and not the traditional way of learning coding. If you go to a coding bootcamp, they're going to start with what is Git? Actually my co-founder, Haya, was a designer. When we're first building the Replit together, she went to WebAssembly to do a coding course. And the first day, they spent this whole time on Git and she's like, "What is that? What does it do?" I still don't know what it exactly does, but it's like you're inverting the process, you're giving the tool before the actual problem. And so I think all of that stuff, you don't have to worry about, so things that you don't have to worry about. I think a lot of the, as a PM, as a designer, as someone who's not in your code editor every day, don't worry about all the tooling. **Amjad Masad** (00:47:09): And if you learn a little bit of coding just by talking to an AI, doing a little bit of debugging, building something with Replit, running into a problem and trying to fix it just using AI, you'll learn a bit of coding. And I have this that's been called not by me, dubbed as Amjad's Law, which is the return on investment for learn to code is doubling every six months. And really just learning a little bit of that skill, learning a bit of skill about how to prompt AI, how to read code, and be able to debug it. Every six months, that's netting you more and more power because you're going to be able to create a lot more. It's going to be easier to create. You're going to be able to create a lot more complete things. So that's another skill that I think could be necessary. **Lenny Rachitsky** (00:48:15): This is super interesting. Okay, so this last point, you made Amjad's Law. It's interesting because when people, as someone's listening to this, I could see them being like, engineers are in trouble. Why do you need engineers at this point? These agents are building the code. Your point is specific engineering skills are going to be incredibly valuable and more and more. How often are they doubling would you say? Every year you said? **Amjad Masad** (00:48:40): No, every six months. **Lenny Rachitsky** (00:48:41): Every six months, these specific engineering skills are becoming more valuable. And the idea is you don't need to know everything. You don't need to know the foundation, to build the app as much. It's more to unblock the agent and understand the mental model of how this stuff is built so that you can move forward fast. **Amjad Masad** (00:48:59): That's right. That's right. Understanding the basic components of it, I would say, yes. **Lenny Rachitsky** (00:49:03): Yeah, so it's like we need new engineering schools to teach you these very specific skills versus spending years on algorithms. **Amjad Masad** (00:49:11): And I think no one has done that yet, and I think this is a big business probably ready to get built. It's like AI native coding. It's totally different than traditional coding. That's why on Hacker News, there's so much skepticism about AI native coding tools, because they're like yeah, it's a glorified autocomplete. And I understand if you're writing operating system, kernels, it's not really doing that much for you, but if you're building products, it's building it for you at this point. And so if you're starting a school to teach AI native coding, you would skip so much of computer science and the basic tools, and you would teach the basic idea of how to structure an app, and then you would teach prompting and then you would teach, I think a little bit of debugging. I think debugging is quite a good skill right now to learn. **Lenny Rachitsky** (00:50:22): Interestingly, if you want to be good at debugging, there's a lot you need to understand, which is basically what you're saying is that's the subset of things to understand is things that break. And to do that, you have to understand how it all works. What are servers? What are APIs? All these things. Okay, so we've been talking about how this is very good right now, building a prototype, building a v1, MVP, people can use it, you can deploy it. You deploy this app, people can start using it, and there's a scale it can reach. Do you see a future where you can build a Salesforce sized business fully Replit or other tools that can scale to hundreds of billions of dollars of value? Or is there just going to always be some limit of like, you need actual engineers and designers sitting on this thing, building it, thinking it? Awesome. **Amjad Masad** (00:51:06): If my law is directionally correct, even if the months are not, I'm not exactly right that the duration is correct, you're going to see a compounding effect of the power. It's actually quite hard to convince yourself. But if you really convince yourself that we are on a massive scale of improvement in AI, then the answer is yes. And it's absurd to my engineering mind that I'm saying it is, but know Ray Kurzweil, this futurist talks about how exponentials are really hard for humans to grasp. And so actually when we started building the agent, I told the team, it's easy and we fall in this trap before. It's easy to build and optimize for today. In '22, we built Copilot-like thing and autocomplete. We train our own models, we optimize the hell out of them. But at some point, that modality was kind of not the right modality, which is the autocomplete modality. **Amjad Masad** (00:52:11): And the right modality is actually this, I think for now, as being able to chat inside the programming environment and for the agent to create things for you. But in order for us to make that bat, a year ago the models were actually not there. The models could not do this, but we were like, okay, we're going to build for the models that are landing in six months. And truly six months later, the model started to land that are capable of this, of the reasoning that we needed and whatever. And so that was like saw it if you want, which is, oh, wow, we switched to it and the reasoning improved so much. And six months later, you have a son of you too. And so it's really almost like a six months cadence. And so if we're really on this trajectory, then I would say next year, you're able to just scale and maybe you get thousands of users paying you. **Amjad Masad** (00:53:08): The AI can do maintenance. We already showed the AI doing SQL queries and doing migrations, so I will be able to do maintenance, debugging, things like that. I think where it gets really tough is that when you're hitting scale and you want to architect a system that is resilient, and so that means you would start sharding databases and you would start using different queue systems and components and things like that. And I think the AI needs to have access to the entire suite of tools to be able to do this. **Amjad Masad** (00:53:49): And I think that's going to be the next bottleneck. And I think the AI needs to be a lot more reliable at doing that. But I could imagine whatever, five years from now, someone running a billion dollar company with zero employees where it's like the support is handled by AI, the development is handled by AI, and you're just building and creating this thing that people are finding valuable and are paying you for it. That being said, it's worth thinking about the economics of it. If the cost of software goes down a lot, then what is the price that you can charge on software? So can you actually build the next Salesforce if anyone can generate Salesforce? And then the question is, and this is why I emphasize being generative, because I think then the thing that will make you better is by being able to iterate and improve the thing really quickly and generate new ideas. **Lenny Rachitsky** (00:55:01): And stay ahead of all the other people building these tools so quickly. Oh, my God. An interesting other kind of mental model I'm seeing as you talk about this sort of thing is not to offend religious folks, but there's this concept of God of the gaps. I imagine you've heard that where it's like God explains all the things that we don't yet understand. And over time that kind of space shrinks and God's like all the things we don't get yet, those gaps. That was God that proves there needs to be a God. And it feels like right now, humans are the gaps in these tools or these agents you talk about that you can hire within Replit are fixing these little gaps. And over time, AI will fix these things themselves. **Amjad Masad** (00:55:44): That's right. **Lenny Rachitsky** (00:55:44): And these gaps will shrink. **Amjad Masad** (00:55:47): Unless we hit some fundamental limit and the current regime of AI, which I'm not an expert about how far transformers could scale, but I feel like we found the thing that could scale pretty far, but maybe there are limitations in data or other things like that that we could be surprised by. But if there isn't, then we are on a massive trajectory of removing these gaps quickly. **Lenny Rachitsky** (00:56:23): Yeah, very true. We have no idea. We keep thinking it's just going to keep going, but maybe it'll stop at some point. I could keep going and going, but I think we should also let people go play with these things and process all the things we've been talking about. Is there anything else that you think might be helpful for folks to think about or learn or study? **Amjad Masad** (00:56:43): I'll give advice to founders or leaders at companies. The way we work is going to change rapidly, and it's important to be resilient to that change. One thing that I think is really difficult now is having roadmaps, especially if you're doing anything in AI, but really anything that AI could affect, you want to be able to react to it really quickly. And so when the Anthropic drop the computer use set of capability, we slaughtered our roadmap because we don't really have an explicit roadmap. We immediately jumped on it and started building things and we launched some things around it. We're going to be doing more with it, but there's going to be capabilities that are going to drop. And you want to really, in some cases, if it really affects your business, you want to be able to jump on it really, really quickly. So being agile, not being stuck with roadmaps, being able to just say, oh, we're just going to switch priorities right away, is going to be super important. **Amjad Masad** (00:57:59): Not being, like I said, with silos at Replit, there's so many people that are on the scale of designer to engineer, designer, product manager. Actually, I mentioned Amman earlier. He started as a designer at Replit, and now as a product manager. We have people who start as designers, become engineers, and we have people in the middle and we're comfortable with that design engineers that fit at different parts of the scale. And the design engineers go to the design correct meetings and some designers go to the engineering meetings. You got to be fluid because again, when designers can code and engineers can design, I mean it really becomes, you can't have a lot of structure around that. So you want to build a culture and you want to build an environment or milieu that is really, really flexible, which is uncomfortable for a lot of people. **Lenny Rachitsky** (00:59:03): Man, the future is wild. Everyone's a hybrid person now. Let me just actually double down on what you just said, which I think is really interesting. It's almost like if you're an engineer, where your skill set will become most valuable is unblocking these AI tools and knowing debugging and figuring out how to allow it to go further and further and further. Within PM and design land, based on what you're describing, where the skills will become more valuable is generating ideas, almost like finding opportunities, discovery, finding what problems need to be solved, and then articulating that as clearly as possible to the AI tooling. **Amjad Masad** (00:59:44): That's right. **Lenny Rachitsky** (00:59:45): Super interesting. **Amjad Masad** (00:59:45): Yeah, this is a very crisp sort of advice that people can follow today, I think. **Lenny Rachitsky** (00:59:50): Oh man, what a world. Okay, I'm jot. This is incredible. My mind is racing. I've got to go build some apps immediately. **Amjad Masad** (00:59:58): Yes, you've back. Love that. **Lenny Rachitsky** (01:00:00): I will do that. So just to leave listeners with a couple things. One is just, what should they know? Where do they find you? How do they try Replit? Anything else other than just go to replit.com? **Amjad Masad** (01:00:10): Yeah, just go to replit.com. It's an open beta right now. We're kind of quickly improving and going to exit beta I think in a few weeks. But if you're comfortable testing something that's not perfect, go to replit.com. If you subscribe to our core plan, you should be able to access the agent and start using it. And we are, I think the place where we're most active is Twitter. So Twitter are like X, the handle Replit, R-E-P-L-I-T or my handle @amasad. **Lenny Rachitsky** (01:00:45): Oh, yeah. One other thing I wanted to make sure we had a chance to touch on is you're working on something new, something that's coming in the very new future, maybe the day this episode drops. Talk about that. **Amjad Masad** (01:00:56): All right. So depending on when the episode is coming out, this could be the first time people hear about it. But we have this product called agent. It is sort of high agency, does everything from setting up the project and all of that. And so now, we are working on assistant. Assistant is let's say the cousin of agent. It is a little less powerful but a lot more controllable. You can focus on features or areas of the code that you want to change and you still don't have to know how to code, but it is a lot more manageable and it is a lot faster. **Amjad Masad** (01:01:38): So you saw how it took some time to kind of create the project and code some of the things. Assistant is in the order of milliseconds and seconds to be able to respond to you. And so again, as I talk about the idea of tools, we want people to have as much power and autonomy as possible. And so there are certain instances where agent is the best. It's going to do the debugging for you, it's going to create the database for you. But if you want more control, assistant is going to give you that. **Lenny Rachitsky** (01:02:09): Just so folks totally understand what this is going to do for them. What's the mental model for what this is? If it's like a person, we're helping you out. **Amjad Masad** (01:02:17): Agent is like having a developer work. You give them the PRD, right? And they're going to go and build the thing. Assistant is like you're sitting next to them. So they built the thing and now you walk over to their desk and you say, let me move this button. Three pixels to the left. Let me change this thing. So small increments of changes that you want happen really quickly and you want it reliably, that will give you that. So it's just much faster iteration on UI and things like that. **Lenny Rachitsky** (01:02:58): Incredible. The future is wild. Final question I always ask everybody, how can listeners be useful to you? **Amjad Masad** (01:03:04): Come work at Replit. We have a PM role. I think up if you're product manager. We're hiring engineers and product managers. So come work at Replit or refer someone to Replit, especially if you're like our tools and you want them to get better. The best way to do that is to get us great people we can hire. **Lenny Rachitsky** (01:03:25): Well, you're about to get a flood of product managers applying. Goodluck. **Amjad Masad** (01:03:28): Amazing. I love that. **Lenny Rachitsky** (01:03:30): Amjad, thank you so much for being here. This was incredible. **Amjad Masad** (01:03:33): Thank you. Thank you for your podcast and the community that you've built and newsletter and everything. It's been awesome to watch. **Lenny Rachitsky** (01:03:40): Thanks, man. Appreciate that. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [12/17] How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) **Lenny Rachitsky** (00:00:00): You basically spend all your time working with founders, and through that studying, you create frameworks and training and you use that in your work. I think that's what many, many founders are looking for is how do I avoid pain? **Jonathan Lowenhar** (00:00:11): To be a founder is a state of being, it's an attitude. To be a CEO is a craft. The more founders who can accept that those are two separate things and they're both equally important to build an ascendant startup, the better all of us will be. **Lenny Rachitsky** (00:00:26): I'm kind of tired of talking about founder mode, but it feels like what you're describing is founder mode and manager mode. **Jonathan Lowenhar** (00:00:30): Founder mode gets me angry. That article just got me hot. It really felt like an excuse. We were giving founders a permission to not learn the job. It's not manager mode is bad, it's the greatest CEOs know when to calibrate which one is needed. **Lenny Rachitsky** (00:00:46): Something you talk about, there's these two phases to a startup journey and most people focus on the first phase. **Jonathan Lowenhar** (00:00:51): Phase one is build something people want to buy. Phase two, the one we don't talk about is now you have to build a company around that thing people want to buy. Building a company is always the same. I don't care if it's MedTech or fintech or hardware or consumer. **Lenny Rachitsky** (00:01:04): You've come up with this methodology that you call the Magic Box paradigm that helps founders think about how to lead to a successful exit long-term. **Jonathan Lowenhar** (00:01:11): This is a traditional sales process. You build a list of the companies that might want to acquire you, you ping them and you hope you get a deal. Magic Box argues that the best outcomes for early-stage startups don't happen that way. You're never for sale. In fact, you have seduced a buyer. They see the fantasy, they fall in love. **Lenny Rachitsky** (00:01:35): Today, my guest is Jonathan Lowenhar. Jonathan runs a firm called Enjoy The Work, which I've heard amazing things about from so many people over the years. Their firm has a singular mission, to help founders become great CEOs. They do this through a blend of mentoring and advising services, which are rooted in their study of how the best startups operate. They take these lessons and fold them into frameworks and advice and training that they offer their CEOs, their insight, which you'll hear in our conversation, is that most founders don't come into the job knowing how to be a CEO, which includes learning how to do hiring, how to manage financials, figure out growth strategy, road mapping, planning, people management, and so many other skills that nobody teaches a founder. **Jonathan Lowenhar** (00:03:03): Lenny, I am damn excited. **Lenny Rachitsky** (00:03:05): So am I. The reason I'm excited to have you in this podcast is that you basically spend all your time working with founders, and through that studying, what causes them pain, what causes them to fail, what causes them to struggle, and then you take that and you create frameworks and training and you use that in your work with founders, and I think that's what many, many founders are looking for is how do I avoid pain? How do I avoid these things that I'm going to probably run into? To build on that, briefly, can you just help people understand what it is you do, what it is your organization does with founders, how you work with founders? **Jonathan Lowenhar** (00:03:38): Yeah, thank you. I'll tell a bit of origin story that I think ends up answering that question. **Lenny Rachitsky** (00:03:43): Let's do it. **Jonathan Lowenhar** (00:03:45): I had run a bunch of different types of companies and they were really different ones. I ran a big division for a public company, then I was a private equity CEO, then I did back-to-back startups. The first one didn't get very far, but we sold it, and the second one got really far. When I left the second one, I was like many founders, grossly unhealthy, 25 pounds overweight, wasn't sleeping enough, all the things. I took a few months to get healthy and then reflect on those parts of my career. One of the things that I noticed at the time was all of those companies, when they got to a good place, when they started to run well, they were all run well in the same way. How could this be? How could public company, private equity, startups, early stage, growth stage, when they were run well, they were all run well the same way? **Jonathan Lowenhar** (00:04:35): I started to obsess about this question, and what it led me to realize is that every well-run company has a rhythm. It's unmistakable, you can't miss it. You can't not see it. You just spend a couple of days through a spy cam watching a business, you'll see the pattern. How come some startups get there and some don't? How does a founder learn the rhythm? How do they learn how to run a company well? I started to ask investors obsessively, and I asked them, Lenny, I asked them all three questions, same three over and over and over again. **Jonathan Lowenhar** (00:05:14): First question was, well, describe to me your ideal founder. What's a great founder? The answers universally were the same. Investors would use words that meant grit and tenacity and courage and insight, and I'd say, "Great. Question number two, describe to me a great startup CEO," and they use none of those words. How can that possibly be true? Instead, they describe skills. This is a person who knows how to build stuff and sell stuff and recruit people and raise capital and organize humans and financially plan. Question number three, my final one, well, how does a founder learn those skills while doing the job? I got blank fucking stares, over and over again. It led me down this path that I'm now 10 years into with my colleagues of, well, how do we help founders learn those skills so that their venture investors don't fire them, so that they can actually go build whatever company they want to build and stay in the job for as long as they want to stay in the job? That's origin, that's what got me going. **Lenny Rachitsky** (00:06:27): **Christina Gilbert** (00:07:57): Yes, thank you for having me on, Lenny. **Lenny Rachitsky** (00:07:59): What is the latest with OneSchema? I know you now work with some of my favorite companies, like Ramp, Vanta, Scale and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs. **Christina Gilbert** (00:08:15): Yes, so we just launched OneSchema FileFeeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP folder. We see our customers all the time getting stuck with hacks and workarounds and the product teams that we work with don't have to turn down prospects because their systems are too hard to integrate with. We allow our customers to offer thousands of integrations without involving their engineering team at all. **Lenny Rachitsky** (00:08:37): I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema and not just to build it but also to maintain it forever? **Christina Gilbert** (00:08:48): Absolutely, Lenny. We've heard so many horror stories of multi-day outages from even just a handful of bad records. We are laser-focused on integration reliability to help teams end all of those distractions that come up with integrations. We have a built-in validation layer that stops any bad data from entering your system, and OneSchema will notify your team immediately of any data that looks incorrect. **Lenny Rachitsky** (00:09:08): I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us and if you want to learn more, head on over to OneSchema.co. That's OneSchema.co. There's obviously this new meme of founder mode. I'm kind of tired of talking about founder mode, but it feels like what you're describing is founder mode and manager mode. You basically have to be good at both. This latter part is almost manager mode. Is that a way to think about it? **Jonathan Lowenhar** (00:09:34): Yes. Founder mode gets me angry. That article just got me hot. **Lenny Rachitsky** (00:09:39): Do share. **Jonathan Lowenhar** (00:09:42): It really felt like an excuse. We were giving founders a permission to not learn the job. If we think about an ascending startup, there's this phase of I have to invent something. I now have to figure out how to get my customer in front of this invention and see if it works, and then I have to build a business model around that to see if there's some repeatable way to attract, win, deploy my customer and thrill them with whatever the solution is. Okay, now I have to go build an enormous amount of demand and then I have to build up an operation that can handle all that demand. Oh, and by the way, at some point, figure out how to turn positive revenues into positive cash flows. The idea that the founder who's writing code by themselves doesn't have to advance their skills to learn how to do all those things, and that in fact what the article even implies is learning how to do those other things is a negative is bananas to me. **Jonathan Lowenhar** (00:10:52): The things required to launch a company are not the same as grow a company as scale a company as exit a company, and the best startup CEOs learn them all along the way. There are lots of ways to learn them. I'm not suggesting there's only one path, but founder mode was almost an excuse not to. I do think what's unique about a founder that felt perhaps where that article was trying to go is that unlike the professional mercenary CEO that gets dropped in, the founder knows everything about what built this company and they can drop in at the most granular level and play anywhere. They can drop into a product feature, they can drop into a customer conversation or a partner conversation or with a long-time employee that's still in IC and be impactful and then rise back up if they've gone the training and get back into a cockpit to run the company again. That's to me the distinction. It's not manager mode is bad, it's the greatest CEOs know when to calibrate which one is needed. **Lenny Rachitsky** (00:11:57): I love that. I'm glad we got there. I wasn't planning to talk about founder mode, but I think this is really helpful for folks to hear that are founders and people working for founders too. Along these same lines, you have a really helpful and really funny also mental model for how to think about common failure modes of founders. You have these labels that I love, and this is actually the first thing I heard about Enjoy The Work is these labels that you guys use, and you also, a similar mental model for failure modes for a startup. Can you just share these modes that you've come up with? **Jonathan Lowenhar** (00:12:31): We do take a bit of a comical approach to some of this. As I've shared with you previously, the name of our company is not an accident. If we can't be playful, we can take the work seriously and not ourselves, so we do fuck around quite a bit. I think if I would separate failure modes for companies versus CEOs for a minute, the company ones are not quite as comedic, but they are ones we see all the time. One is you chose the wrong market. I don't think we need to belabor that one. Lots of your prior guests have talked about the importance of getting that part right or nothing else really matters. **Jonathan Lowenhar** (00:13:05): Second, back to what we were discussing a minute ago, build something people want to buy, got to go build the right thing. Cool. Third one, founder's function. We like to joke that more companies die from suicide than homicide, and it's grim, but also if the two or three people in charge of the business can't get along, nothing else matters. It's all going to break apart. Then fourth, execution, and execution now leads back to CEO. Okay, so now we have a bunch of playful ones here. We have the robot CEO, who believes emotion should not ever exist at a startup, at which point we train them on a very simple formula. Emotions are messy, humans have emotions, startups need humans, therefore startups are messy. **Lenny Rachitsky** (00:13:57): I love how engineering-oriented that advice is, which makes sense for robots. Yeah. **Jonathan Lowenhar** (00:14:03): Also, a little bit more graceful of an answer there is also our CEOs want urgency and passion and excitement from their teams. They want them working enormously hard for below market comp more often than not with this promise of equity that might return value five or 10 or 12 years later. They want them to bring all of that emotion, but they're supposed to figure out how to surgically cut off the emotions that are inconvenient. That's the robot CEO who believes that we can just have several robots working for us and you just press a button and they do a thing. Second one is a pleaser CEO. This is the person who is far more concerned with being liked than running a business, so they can't tell anyone hard news. They can't break ties, they want a consensus on everything, and that's not possible. **Jonathan Lowenhar** (00:14:56): If you have a group of thoughtful people working for you, they're going to fight, they're going to debate and you want them to. Then at some point you have to call it and say, "No, we're going left not right." Or, "The two of you need to go get in a room and deal with something." Or, "Hey, the way you just showed up is not the way I want you to show up." The pleaser CEO won't do any of that. They will simply hide and pray It goes away and it won't go away. Next one is a perfectionist CEO. I'd like to say that these are the CEOs with the most beautiful product to be delivered minutes before they file for bankruptcy. This is the person who is far more concerned with being right and believing that there's always a right answer than just moving forward. **Jonathan Lowenhar** (00:15:36): It creates two problems in a business. One is you're just slow and the other one is you'll never take any bets because you will build a team that realizes the CEO is not allowed to be wrong, so you can't disagree, you can't use intuition, you can't use gut. Everything has to be utterly factual and that is simply not possible. In early-stage startups, you have more questions than you do answers. Everything is circumstantial. It's not like watching CSI entrepreneurship and you get to see a video to say, "Oh, look, the guy did it." No, we have a bunch of little data points you have to come to a conclusion. The next one is the angry CEO. **Jonathan Lowenhar** (00:16:15): I had a founder of mine a bunch of years ago and we were seeing a pattern across the leadership team and he and I get on the phone one morning and I said, "I have a theory for you. It might be a story, I might be wrong, but I want to share." He said, " Okay." I said, "I think you wake up in the morning angry and you don't know it, and then you get to the office and you beat the crap out of the first employee that crosses paths with you over something utterly unrelated because you're angry. You realize that a few hours later and you apologize and your team hasn't quit yet because they believe you're a good human who doesn't have good self-control." Then I shared with him, "And you just had your first child. My guess is because I'm not a psychologist, I'm not a therapist, that you are modeling something that's happened in your life. Is this something you want to change?" **Jonathan Lowenhar** (00:17:09): His answer is yes, and I said, "Great. I have good news and bad news. The good news is because you said yes, we can do something about it, and the bad news is I don't know what to fucking do. That's not my job." The point being, no one wants to work for the angry person. I don't care what the equity potential is worth, no one wants to work for that person, and the moment they see greener pastures elsewhere, they're leaving. The next one is the one that drives me particularly crazy, it's the laissez-faire CEO, who insanely believes that I can just hire great people and utterly ignore them and let markets take care of themselves and they will do all the right things. I have never met anyone, Lenny, that didn't benefit from good management and the laissez-faire CEO believes that management is not required, and so what they ultimately find is they have really, really good people doing utterly disconnected things and goals are not achieved. **Jonathan Lowenhar** (00:17:59): Every CEO we can reductively reduce to one of two characters. They're either comfortable with the brake or comfortable with the accelerator. The challenge with those who are comfortable with the brake, what I mean by that is they don't want to spend any money, so they're driving this beautiful sports car and they're just leaning on the brake the whole time. Yes, they won't run any money, and yes, they will also get lapped by everyone else and miss the opportunity. Where their opportunity is, is where can you take bets? Where can you actually downshift that car in such a way where you give yourself a chance in the market? Separate, those who ride the accelerator, we've all met this one. They're going to run out of money really fast, and this connects to one of our other challenging CEO types, the ready, fire, aim. **Jonathan Lowenhar** (00:18:49): Most CEOs are really bad at planning and that's because there's this little-known secret in the Bay area, most CEOs have never run a business before. Planning doesn't have to be some heavy bureaucratic multi-month exercise that begins in August and ends in February, but a little bit of bottoms up planning to say, what are we trying to achieve? How do we quantify it? What resources are required? What humans are going to do what? How do we shorten feedback loops so we know in a week, in a month and two months, whether we're on the right trajectory? The ready, fire, aim CEO says, "I don't want to do any of that because they're improvisational and they just want to take bets and they want to take shots," and that's what got the company started, and that's also what will have the company go bankrupt. The micromanager one is the opposite of laissez-faire. They believe that no matter how many employees they have, they can do the job better. **Jonathan Lowenhar** (00:19:42): The challenge with this one is it is massively disrespectful to those who work for you. We think that, and this is a bit insulting, that everyone that works for a founder can be fit into one or two chunks. They're either an adult or a child. I have a three-year-old, my little girl is amazing. I'm utterly in love. If she doesn't have a lot of structure and a lot of supervision, she's going to run into things, man. Into things, off things, through things, but adults don't need to be given utter instruction and watched all the time. In fact, it needs to be the opposite. We agree on what success is, what resources are, and you let them go and they'll come back to you when they have questions. The micromanager CEO doesn't see the difference between those two humans. They don't trust anybody and that's actually the thing under the thing under the thing, so they want to do everyone's work and that will succeed right up into the point everyone quits. **Lenny Rachitsky** (00:20:39): This is amazing. Okay, so let me recap these labels that you have just for folks. I have them written down here. There's the robot CEO, perfectionist CEO, pleaser CEO, micromanager, laissez-faire, ready, fire, aim, riding the brake and then riding the gas, and as you said, the ever-popular angry CEO. **Jonathan Lowenhar** (00:21:03): You got them all. **Lenny Rachitsky** (00:21:04): As people hear this, I imagine people self-identify a few of these, like I have some of this, I have some of that, and it's not like black or white. No one is like, "I'm a 100% robot CEO, and I need to fix that." It's like a pie chart kind of, I don't know, what's a visual of this? Everyone's got a little bit of this, basically. **Jonathan Lowenhar** (00:21:24): That's right. I enjoy giving this talk on stage and watching different founders in the audience cringe at different moments, but it doesn't mean that they're all one or the other. If they were all one of these and then didn't want to even accept the possibility that there's a little bit of a lot of these that they could work on, they're probably not coachable and they're not going to be in the talk anyway. **Lenny Rachitsky** (00:21:45): It's like I imagine each of these is very particular and it's this journey you go on to work on yourself. Let me just ask, what's the most common issue that you've found across these labels of type CEOs? What's the most common one and what do you often recommend someone to work on specifically to help them through that? **Jonathan Lowenhar** (00:22:02): I think ready, fire, aim is the most common that we've seen, and that has been an affliction that's been growing in the last number of years. It wasn't long ago that CEOs could paper over poor execution with easy access to capital. Suddenly, over the last number of years, we're expecting founders to be better operators. Better operators means eventually being on a path when more cash comes into the business and out of the business. That doesn't happen by accident. The ready, fire, aim CEO has probably suffered this pain where they took lots and lots of bets. Maybe they measured the outcome after the fact and they were wrong and they were wrong and they were wrong in ways that were expensive, and they've raised their hand to say, "I see it. I want to get better at this." Basic, basic business design and business planning is not some corporate effort. It's some thoughtful exercise that starts with what are we working backwards from? **Jonathan Lowenhar** (00:23:02): Because in any given time, Lenny, companies are working backwards from one of four things, whether they like it or not. I am working backwards from an exit. I'm working backwards from a next fundraise. I'm working backwards from profitability or I'm working backwards from winding down. We don't talk about the fourth one that much, but I got to choose one. I got to choose the top of the mountain. More often than not, they're choosing a fundraise. Then we'll ask that founder, you know your market, you know your investors, you know the next set of investors, we've done some intel. What has to be true to unlock the next fundraise? That's a qualitative and quantitative answer, but we write it down. We need to get better at go to market. We need to land our first partner. We need to launch next iteration of the product and show this level of efficacy, engagement, what have you. Can we codify that? Yes. Can we talk through what actions would be required on what cadence to unlock that quantified set of results? Yes. **Jonathan Lowenhar** (00:24:00): ... that quantified set of results? Yes. Do we understand what resources would be required to do those things? Recognize we might have to squint through some of it, but again, the answer is yes. [inaudible 00:24:13] now aimed. If we have a culture that has some accountability, that has a communication architecture, so there's some rituals about how we meet and how we share information and how we talk through problems, and how we work through bottlenecks, well, now we have a plan and now we have accountability. I now no longer have to just guess all the time. And this only works for the CEO who says, "My improvisational efforts got me here, but I don't think they'll get me there." **Jonathan Lowenhar** (00:24:47): There's a guy I worked for a long time ago, and he had this phrase... He had like seven or eight phrases, he would use them over and over and over again. It was hard not to commit them all to memory, and one of them was, "If you keep doing what you're doing, you keep getting what you're getting." And for the ready, fire, aim folks who realize the weakness of that at scale, the way to counteract that, is to start with good planning. **Lenny Rachitsky** (00:25:12): It's interesting that's the most common type of CO, when with Founder Mode, it feels like it just accelerates that further. The whole meme of Founder Mode, which are what makes you upset. Makes sense. Great. **Lenny Rachitsky** (00:25:26): Okay, so I love that you talked about exiting as basically one of these four working backwards paths, because that's where I wanted to go next. I want to talk about some of these specific frameworks and skills and methodologies that you teach, and one of them... I want to almost go to the end of selling your company. And the reason I'm excited to talk about this, is if you think about, and tell me if I'm wrong, but it feels like most startups that succeed end up selling their company. That's the most likely success, right? **Jonathan Lowenhar** (00:25:58): Yes, by far. **Lenny Rachitsky** (00:26:01): Great. Yeah, because the other option is IPO or just run this privately forever. Or fail, basically, and fold. So of the successful options, the most common is selling. At the same time, founders have never done this before, they don't know what they're doing. The other side, often, has done it many times, and so it's a pretty treacherous and scary and high-stakes thing to do and to learn on the spot. And you've come up with this methodology that you call the Magic Box Paradigm that I love, that helps founders think about how to lead to a successful exit long term. Can you talk about what this is? **Jonathan Lowenhar** (00:26:36): I can, and I want to give credit where it's due. There's a book by this name, it's called Magic Box Paradigm, written by an independent banker named Ezra Roizen. And the book's fantastic, and Ezra is fantastic. **Jonathan Lowenhar** (00:26:46): What we've done, is we've operationalized it so that we could teach founders over, and over, and over again. If the founder wants to hire a banker for this particular process, because we're not bankers, we're not BD, we don't get paid that way, we're teachers. But if wanted to hire a banker, go hire Ezra. But the methodology itself is a inversion for how venture and venture boards have thought about startups being ready for sale for a long, long time. It's utterly counter to so much advice that founders have heard. There are two ways you can get acquired. This is purposely reductive. One is you put up a for-sale sign. This is a traditional sales process. You build a list of the companies that might want to acquire you. You figure out the categories of buyers, the companies there, the contact list within that. You ping them and say, "We're open to a transaction," or some euphemism the like. You contact them and say, "I'll give you some information now. Sign an NDA. Give me an indication of interest by this date." And you work through a process, and you pray you have more than one person at the end of the game, try and ratchet them up, sign a term sheet. They will then re-trade along the way, right up until the point you die and you hope you get a deal done. **Lenny Rachitsky** (00:28:05): Sounds very familiar. **Jonathan Lowenhar** (00:28:08): And it's one that often will just hit the nervous system of any founder that's been through it a couple of times. Because man, is it a fraught exercise? What Magic Box argues, is that the best outcomes for early-stage startups don't happen that way. You're never for sale. In fact, you have seduced a buyer. You have brought someone in. And there are three stages to Magic Box work. There is learn the fantasy, there's prove the fantasy, and there's quantify the fantasy. **Jonathan Lowenhar** (00:28:43): All right, so what the hell do I mean by a fantasy? You're an early-stage startup, and you meet a company that is in your space, in your vertical, what have you, and they're much more advanced than you. It's a large business. Generally speaking, another oversimplification here, large companies are interested in small companies because they're technology. And small companies are interested in large companies because they're distribution. And there's someone at the large company who becomes fascinated with you. **Jonathan Lowenhar** (00:29:12): What's the fascination? What they see in their head is, "Oh, interesting. If I buy your company, this thing happens." The classic example of this is Instagram. This is the number one example of this. Lenny, do you remember how much revenue they had when they got acquired by now Meta? **Lenny Rachitsky** (00:29:33): I think it was zero. **Jonathan Lowenhar** (00:29:34): I think it was zero. **Lenny Rachitsky** (00:29:35): Okay. **Jonathan Lowenhar** (00:29:36): Do you remember the acquisition price? **Lenny Rachitsky** (00:29:37): A billion dollars, which was absurd at that point. **Jonathan Lowenhar** (00:29:41): There was no math Facebook could use, historically speaking, that would justify a billion dollars. It had to be a model on the future. This is Magic Box to a T. They had a fantasy that adding Instagram would expand ad revenue. They figured out some way to prove it. I'll explain more on what I mean by proof. And then their quantification was based on the future. And that's the difference between a Magic Box approach and traditional approaches. Traditional approaches are based on the past, Magic Box is on the future. **Jonathan Lowenhar** (00:30:14): Let me tell a story. In one of our companies in construction tech, their technology was able to suck in video camera data from construction sites for project planning. No one was doing this yet. And the business was doing pretty well. We helped the founders launch the company. We got first product in market. We raised a couple of rounds of capital. The product mostly worked. But we weren't sure it was venture scale as we were going along. And we had some large construction tech companies and real estate companies and development companies leaning into us. And one particular company then said, "Huh, we're really good at construction planning, and we've collected all of this video data that we don't use at all." And the champion on the other side in the product org, he has a fantasy. "Oh, shit. We take your video analytics platform and plug it into what we do, and this is what happens to my business." **Jonathan Lowenhar** (00:31:18): Now, the person on the other side is a person. And the reason I'm being specific about that, is because you don't sell to a company. Magic Box is about finding the person. You're finding the champion on the other side, the person who has motivated for their own reasons, career, money, reputation, what have you. They see the fantasy. They fall in love. And this person says, "I am in love with this idea. If I can grab security data into my product organization. Now I have to prove the fantasy." **Jonathan Lowenhar** (00:31:53): What's different about a champion in this kind of process, is they want to find a way to say yes. They're not looking for a way to say no. And this brings us to the four characters you're going to meet along the path of Magic Box. There might be a fifth. You're going to meet your champion, you're going to meet your advocates, you're going to meet your blockers, and you're going to meet your buyer. You might meet Corp Dev along the way. **Jonathan Lowenhar** (00:32:20): Let me talk about each of those folks. The champion is the one who's fallen in love. They're the ones with the fantasy. They're the ones who are arguing on your behalf. They're the ones fighting for you when you're not in the room. They are texting you, they're telling you things about the business that they're probably not supposed to tell you. **Jonathan Lowenhar** (00:32:33): The buyer. All they care about is math. It might be a committee, it might be a group, the IC, the EC, the investment group, what have you. They're the ones who actually can sign off on a deal. They care about business case. **Jonathan Lowenhar** (00:32:45): Advocates... Lenny, do you play chess? **Lenny Rachitsky** (00:32:49): I have played chess, yes. **Jonathan Lowenhar** (00:32:50): You have played chess. So advocates are pawns. They don't matter at all until they matter enormously. These are folks that, like, you are the CEO doing a meeting with your potential buyer, and there are somehow 12 people on the Zoom call, but only two do the talking. The other 10 might be advocates. They're rooting for you, but they will take no political risk. Their value is in giving you intel. **Jonathan Lowenhar** (00:33:16): Blocker. This is the person who can't say yes, but they can say no. This is OPSEC, this is Procurement, this is Legal. You're going to meet all these characters during the Magic Box dance. Your champion just wants you to get the deal done so in love. So what happens, is they've come up with a fantasy and you as a CEO need to lean into it. This isn't enterprise selling. I'm not trying to sell you this thing that I have. I'm just trying to find ways to say yes. **Jonathan Lowenhar** (00:33:47): So when, in my story, the person says, "Could we provide you all of our video data that we've collected forever and you now could enhance our ability to predict whether large- scale construction projects are on time"? I don't want the CEO saying anything other than, "We can do that." **Jonathan Lowenhar** (00:34:07): Now, phase two, I need to prove it. Okay, because I have a champion who wants to say yes, proof can be really easy. And the reason the proof is so important, is not to convince the champion they're in love with the fantasy. They're already convinced. It's because in almost all cases, big company is buying little company and your champion doesn't have unilateral authority. They're going to socialize the deal. They have to get buy-in from who? The aforementioned buyer. They have to be able to survive the aforementioned blockers. **Jonathan Lowenhar** (00:34:43): So eventually, when they pitch this to whatever committee is in charge, that committee is going to say, "What proof do we have that it works?" And we just want to be able to provide the champion with enough evidence that it works. So in this case, we said to the champion, " Well, give us video data, and we will provide you the evidence that you need." Because we're dealing with a champion who's not a cynic, because champions aren't, we could tell them, "And provide us the data in this way, in this fashion, and here's what we'll send you after. Are we in agreement?" We know we're already going to win the proof, and it's critically important in these dances. Number three, quantify. At this point, we're not up for sale, but we're spending a lot of calories on somebody, and they know it. So we have our CEOs say the following phrase to them: "My board is asking questions. They're wondering why we're spending so many calories on this when it's not really core and we're not selling you our product. I'm convinced of how exciting this could be, together, but I think we need to do some math. So I can explain to my board why this might matter. So let's imagine all this works, because it's going to work, and it's a year from now or five years from now. What changes about your business?" And the champion will tell you, "Retention does this, or deal size goes like this, or market share goes like this." And you'll say to them, "Fantastic. Look, I'm going to build some shitty verse version of the model. You tell me what I got right and what I got wrong, but I have a board meeting in 16 days, and I need to be able to walk them through the justify why I am spending so many calories on this exercise." **Jonathan Lowenhar** (00:36:34): You build the model, you hand it to them. If they in any way respond to your model, you've won. Because you have now divorced history from future, and you are now playing in future, you are playing the Instagram game in this case. The ending of the story for the company that I was describing, it was a business sub 2 million in revenue. Our prospects of raising series B felt low. We were not yet profitable, and that was an exit that was generational wealth for the co-founders and their families. The CEO went on and spent two-plus years with the now public company that did this acquisition. The technology did get integrated, but it took a long time and they had to do a lot of changes to it, certainly beyond what was envisioned during the diligence process. But all parties are happy. And if we hadn't done it this way and we had just been up for sale, we'd get a dollar for that company. **Jonathan Lowenhar** (00:37:40): A couple of other side points that are really important here. For any of you founders out there that are thinking about working backwards from an exit, there are two things that I really want to stress. One is the fantasy is beyond just, "What is the business change you can have?" The fantasy is, "Your books are in order." Your fantasy is all of your investors will sign off on the deal and you will have unanimous consent, that the key members of your team are going to stick around, that you're a joy to work with. Please God, founder, do not puncture the fantasy at any time. **Jonathan Lowenhar** (00:38:21): So whatever is starting to shape in your buyer's mind, get to know it. Live that everybody wins from that game. Second, Corp Dev, they will probably show up in the stands. Corp Dev make deals. They're not deal sponsors, they're not a champion, they're not a buyer. They are an expert negotiator. Their job is to facilitate deals and get deals done. The most important things to understand is that they can be a leverage point to have a deal move with some process and some pace and some urgency. Because either deals have momentum or they die, and Corp Dev can help there. **Jonathan Lowenhar** (00:39:04): Second, they are way better at negotiating than you. So anytime dealing with a superior negotiator, the only thing you can do to try and even the scales, is move the negotiation async. So founders, repeat after me, I'm talking to you directly now. You'll say to Corp Dev, "You know I'm not alone in this decision. I love what you just said and I'm excited about this opportunity. Once I see it in writing, I can socialize it with advisors, lawyers, co-founders, whoever." But don't negotiate live. You will lose. **Lenny Rachitsky** (00:39:39): Let me just say that was extremely delightful to listen to. I've never heard like a M&A strategy be this fun. And it makes me want to sell a company. It's like, "Okay, let's do this. I'm hyped." I think you got it all. I have a few questions. **Lenny Rachitsky** (00:39:56): Interestingly, the middle part is... It feels a lot like enterprise sales, which a lot of founders are used to. Understand the stakeholders move things forward. Here's your champion, here's your blockers, here's the buyer. Is there anything there you want to say, what's maybe most different from enterprise sales, which I think a lot of founders are maybe used to? Or is it pretty similar? **Jonathan Lowenhar** (00:40:14): Yeah, I think three things. One is there are a lot of moments in enterprise sales where we're trying to push for a compelling event. That doesn't work in seduction. The playful metaphor that we'll often use, is you've been dating for a while, this person could be the person, but they're not quite convinced yet that it should be a life together, and you're sitting at dinner. And in enterprise sales, you're eager to get it done. You're eager to move the relationship forward and move in and get engaged, what have you. And so you might be inclined to say, "Hey, either we move this relationship the next step, or there are a whole bunch of people eyeing me, and I'm going to go date someone else." **Jonathan Lowenhar** (00:41:06): That conversation never goes well, and in Magic Box founders are eager to do the same thing, thinking that competition will improve their deal size, when in fact I think more often than not, that is a negative signal until the very end of the dance. So instead in enterprise selling where I'm pushing, in Magic Box, I'm always trying to entice, I'm never, ever trying to push. So instead I might say things like, "Hey, I'm going to raise my next round in Q1, because I've been intending to do this business independently. Now all I really want to do, is win. I just want my product in as many customers' hands as possible. Whether I do that on my own as I was planning, in partnership with someone, or under someone else's roof, honestly I don't care. But I have a company to run and I'm going to go raise my next round in Q1. And if I do that, probably too expensive for this deal to make sense anymore, and my board will want me to move on anyway." I'm enticing. I'm never trying to push. **Lenny Rachitsky** (00:42:15): **Jonathan Lowenhar** (00:43:28): Ezra does this really well in the book. Again, it has to be not solicitous. So one of our companies, we had maybe 20 months of capital left, and the two co-founders and our team were convinced, "This isn't a venture business. We thought it might be a venture business. It's not a venture business. It takes too long to do a deal that's not that interesting with each of our enterprise customers." It was disappointing, but at least we were honest about it. "Okay, so who are we going to sell to? Let's go play this game." **Jonathan Lowenhar** (00:44:04): So we started with categories, categories of buyers. It could be, for this particular example that was in my head, ERP companies could be a buyer, large banks could be a buyer, the big software companies like Microsoft could be a buyer. There were a few different categories. And we said, "Great. Who are the companies within those categories that make sense?" They're acquisitive, they have the balance sheet for it. There's a Corp Dev department, so we know that they actually know what they're talking about here. Ideally, there's an existing relationship with core team or advisors or board members. Make a list. **Jonathan Lowenhar** (00:44:45): Now, how do we meet them in a way without selling them? So one of the examples in the book, which I love, is small startup wants to meet the luminaries in a space, and they have their PR agency set up a panel where they contact the CEOs of the potential buyers and say, "We're putting together a panel of the world's foremost experts in X. We're going to put four people on the panel, and it's going to be you and famous person number two and famous person number three, and this fourth person," that is a luminary to us. And it's our startup CEO. And suddenly you're at the table as a peer. It's a completely different conversation. **Jonathan Lowenhar** (00:45:32): The second one, and this is going to sound a little silly, but I am not exaggerating, it works. If you are a CEO founder and you have that title on LinkedIn, it's amazing the responses you'll get. So we made this list and we just started to send connection requests to the CEOs or CPOs or CFOs on our target list, and said something as simple as this, "You're doing something really cool. So are we. You game just for a 30-minute chat? Because I don't know where it'll go, but I think it'll be fun." Keep it that informal. It's peer to peer. I'm not selling you anything. **Jonathan Lowenhar** (00:46:10): If you can draw a line to some post that they had or some speech that they gave, even better. But we found without fail, there would be math that would show up, one out of four, one out of five, or one out of six, "Yeah, that sounds fun." There's a lot of those CEOs never talk to startups, and that's fascinating to them, especially when presented with the energy of, "I just want to have a fun, intellectual discussion." **Jonathan Lowenhar** (00:46:37): What you're looking for in that first conversation, and this is what we ask our CEOs to do, is to ask questions like, "What do you care most about in the next year? What's the mandate? What about for your department? What are the things that keep you up at night? What's the break? What's the thing that could actually kill everything, if you had a pre-mortem for the next year?" Those kind of open-ended questions, because what we want our CEO listening for, is the fantasy to see if there's some intersection between what they care about and what we might be able to squint and say we do. **Lenny Rachitsky** (00:47:07): It's interesting, because it sounds a lot like there's a jobs-to-be-done framework here, or just like, "What is the job they need done?" What is the pain you're going to solve, and then create a fantasy around how amazing it'll be for them if you can solve that problem. **Jonathan Lowenhar** (00:47:19): And ideally they'll say it and you just reflect it back in active listening. **Lenny Rachitsky** (00:47:25): Chris Voss negotiation style. Okay, so you're the kind of guest, Jonathan, where the whole podcast could be about each one of these topics, and so I know there's so much more to talk about here. I want to move to a different topic, but to leave folks with, one is if they want to explore this methodology more, there's a book you mentioned, called Magic Box Paradigm by Ezra Roizen, right? **Lenny Rachitsky** (00:47:51): If companies are in this process, starting to think about it, does it make sense for them to come to you and like, "Hey, help me through this process"? I know you said, "Go to an investment banker." Or does it make sense to like, "Hey, let's bring on Jonathan," or someone from your team to help them? **Lenny Rachitsky** (00:48:00): It makes sense to like, Hey, let's bring on Jonathan or someone from your team to help them. **Jonathan Lowenhar** (00:48:03): We meet two types of founders. Founder one says, fix this part of my business, totally transactional. I want to raise the next round, or I'm hiring people badly or my founders aren't getting along, or I want to sell my company. Well, I need to be honest, that's not interesting to us. That's not our work. Go find someone who is, and I don't mean this disparagingly, but like a screwdriver, like fixes one thing, go fix one thing. Then we meet second type of founder and that founder says, most likely to themselves, 'cause it's the only safe audience. There's some gap between the CEO I am and the one my company needs me to be. There are a set of skills that I'm great at and there are these things where I know if I'm really honest with myself, if I listen to the quiet voice, I'm soft at these things or I'm not good enough at these things or I have some imposter syndrome about these things and if I don't get better at them, danger. That's the one we work with. And it's when they care that much about both the hard skill development and maybe the soft skill development in their path to become a great CEO. **Jonathan Lowenhar** (00:49:10): How to sell the company. It's one of the skills. We teach this to all of our founders as well as hiring and management and planning. I don't care what the thing is. For every one of our founders, we audit them and say, here's what you're great at, here's what you're shitty at, and here's what you've never done before, and which of these do you want to work on next given where the company is in its cycle. **Lenny Rachitsky** (00:49:29): Great segue to where I wanted to go with this, which is hiring. So I hear all the time that a founder's core job is fundraising and hiring an amazing team. Basically that's their main goal. Just like hire amazing people. The people you hire make your company, create the culture. You got to get that right. But similar to trying to sell your company, most founders have never really hired lots of people, they've never hired for all these different skill sets they're trying to hire for and I know that you guys spend a lot of time helping founders hire and find amazing people. Can you just share some of the advice you share with founders for how to find and hire amazing people? **Jonathan Lowenhar** (00:50:06): Yeah, so we actually think the CEO has three jobs. We agree with the two that you said, but we think there's a third. One is, make sure everyone knows where we're going. The second one, pick the right people for the team. Third one, give those people the tools they need to win. And you can abstract from those what they all mean, but- **Lenny Rachitsky** (00:50:27): I love that. **Jonathan Lowenhar** (00:50:28): ... most founders are really bad at hiring. They fall prey to all sorts of pretty common human biases. The lazy ones, back to laissez-faire, think it's just gambling like, oh cool, they worked at Meta and Salesforce already, so hire them, just gambling. There was work done by and then codified in a beautiful book. I'm going to make sure I get the names right, Geoffrey Smart and Randy Street. They had a consulting firm that dates back to the mid-nineties. Then they wrote a book in 2007 or 2008 called Who: The A Method for Hiring. We have operationalized that book and then expanded on it 'cause there are some parts of it that we found a little dated, but it's really still as applicable today as it ever was. **Jonathan Lowenhar** (00:51:18): And I think there are three core mistakes that founders make all the time, that can be really easily rectified. The first one is, you should hire people who have already done the thing you need to have done next. And I know that sounds simple, but founders don't think of hiring that way. They start with a job description. We've been taught that for a long time. Start with the job description. It's a fucking mistake. Start with, it's 12 months later, you hired the person, they started today, 12 months have gone by, you're clinking champagne because of how great it's been. What's changed about the business? What does success look like 12 months later? Document it. And then when you interview people, look for people that have already done that stuff. **Jonathan Lowenhar** (00:52:13): Second, the notion of does the person in front of you have a history of creating raving fans? They talk in the book about this idea of you being pulled or pushed in your career. If you were an outstanding performer in Job A, it is a high likelihood that in job B, someone associated with you in job A is going to pull you into the next thing and then pull you into the next thing and pull you into the next thing and you'll never do a job search 'cause you were great. And if you see a history of that, ding, ding, ding, ding, ding, really attractive candidate. Third, core values matter a lot. Culture is not an accident. Culture at scale is the codification of what matters to a business and the ritualization of living those values. It starts with whoever the founders are and then it will emanate across as long as the founders are super consistent. But that also means you need a methodology for evaluating the next human in front of you on whether they actually represent your values. We think of these interview stages in a way similar to the book, we use slightly different language, but we think that there is a culture interview, there is a functional interview, and there is a technical interview, but they're designed to get at these notions of have they actually done this kind of work before? Have they been pulled or pushed in their career and are they your kind of human? **Lenny Rachitsky** (00:54:00): Funny on that last detail actually, [inaudible 00:54:03] at Airbnb, there was actually a core values interview team that was formed around studying what the founders Brian, and Joe, and Nate valued specifically and then they codified them to core values at the business and then there's this team that was a very select handpicked team that at every interview loop interviewed the person for their values. **Jonathan Lowenhar** (00:54:22): That is a beautiful example of how interviewing for values is independent of title. 'Cause you'll find people in the company at every stage of a company that are the best ambassadors, the best embodiments of those values. Please use them for interviewing and in addition, they love it 'cause they're protecting their castle. They love where they work, they want to keep it that way. **Lenny Rachitsky** (00:54:45): So true that team is a real special team and it was really honored to be on that team. So let me summarize what you just shared, which I love. There's so much value here, it just keeps going and going. So when you're hiring, your advice is: look for people, one, that have done it before; two, that have been pulled from job to job by someone else that loves their work and wants them to be with them at this new company. And then three, their values match the values of the founder and the business essentially, right? **Jonathan Lowenhar** (00:55:11): Yes. And for the recruiters out there, a really simple way to get rid of a lot of the crap that ends up showing up at the top of the funnel is just to ask the simple question even in the cover letter, of your last ex-bosses, how many would get on the phone and say, you're amazing? If there's any equivocation in the answer, great, move on. **Lenny Rachitsky** (00:55:35): So a couple of follow-up questions here. One is, this point of hiring people that have done it, obviously this implies don't hire junior up-and-comers as much. Thoughts on just when it makes sense to hire someone more junior that's really ambitious, real smart, you think they can learn the job, thoughts there? **Jonathan Lowenhar** (00:55:53): So one of our companies is hiring a team of reasonably junior account execs. We're looking for folks that have been out of school for two years. Now, that means they are highly unlikely to have had three years of quota achievements and a similar... you get the point. Okay, so how do you hire someone who's already done it? We know what success looks like 12 months later. For that role, they've learned how to hunt, they've been able to create pipeline of X and close Y in business, et cetera. What we are looking for then in their history, if they have any sales chops of any kind. They could be selling Girl Scout cookies, or tickets to some event, or they work for a non-profit for while. I don't care, but I want some evidence that they've sold. I want some evidence that they're comfortable getting on the phone or showing up at meetings or showing up at events. So, that they've done it before should be reviewed or thought of creatively. **Lenny Rachitsky** (00:57:07): Got it. **Jonathan Lowenhar** (00:57:07): Now for more senior roles, I want an explicit. We think of, for example, for executives, Lenny, we think there are three types of executives that startups end up hiring over time. We call them the architect, the optimizer, and the scaler. The architect, let's use sales as an example. This is someone who has to build a playbook. So they're going to uncomfortably stay close to the founder, watch and listen, and listen to recordings and pick their brain to pull the magic from the founder of like, oh, here's the dance that she or he goes through to actually close a deal and they write first playbook. And the goal of the codification of that is so you can bring on a first account exec and the next account exec because account execs back to our language earlier in this adult children dynamic are children. You need to give them structure for them to win. That's the architect. The optimizer, this is someone who's now going from a few account execs to maybe 10, 15 and we now have targets we have to hit. The business is now reaching a different level of professionalism and expectation and you have to optimize that earlier playbook to try and find more efficiency and performance out of it. **Jonathan Lowenhar** (00:58:21): The scaler is saying, okay, now how do I find leverage? How do I have 10X more account execs or how to get other people to sell for me? They're all going to be called VP of sales or chief revenue officer. They're completely different archetypes, and that same person exists in engineering and in product, et cetera. In those cases, I only would want to bring on an architect if they'd been an architect before. If they'd only been an optimizer, they're going to fail because they've never written playbook from scratch. **Lenny Rachitsky** (00:58:50): It touches on a conversation I had recently. It was a live podcast recording with Shreyas Doshi at my summit where he talks about a lot of people are really frustrated at work because they're in the wrong one of those buckets, essentially. Like you enjoy certain type of work and your job is not doing that type of work, whether it's in your case scaling or optimizing. And so, it just reminds that if you're frustrated at work, you're in the wrong job in terms of the type of output they're trying to expect from you. **Jonathan Lowenhar** (00:59:18): The story in my head is that talking to me and my colleagues sometimes can feel a little like death by frameworks. We have one for everything and in this example, I think if you're going to be sustainably successful in any kind of job, I don't care what it is, three things have to be true. You have to be good at it, you have to like it, and the market has to give a shit about it. And if one of those is off, you're not staying in that job long. **Lenny Rachitsky** (00:59:40): Yeah. And this touches on the name of your firm, Enjoy The Work, got to enjoy the work to make it sustainable. Okay, one other thing. So one other follow up question real quick on the hiring and then I want to talk about one other bucket of work. And again, I think each of these could be like an hour, two hour long podcast conversation. I love that there's this recurring theme of working backwards to inform what you do today. So earlier you talked about working backwards from what the outcome you want next for your business, whether it's fundraising or exit or winding down. And for hiring, you have the similar advice, work backwards from what you want this person to achieve in the first year, whether it's drive this sort of growth in the product or drive sales. I guess anything else there of just the power of working backwards versus the typical approach for hiring, you talked about job descriptions. **Jonathan Lowenhar** (01:00:26): Hiring is never the goal and it's often the first thing that we'll hear from a founder, "I have to hire this person." One, that is so dangerous for confirmation bias. The hiring manager is always the one most burdened by that particular bias, but it's also hiring is never the goal. We will pull them back to over and over and over again, which of the three milestones matter, right? Fundraise, exit, profitability. What has to change about the business, for example, to get to that fundraise? How do we quantify that change? Some sort of goal setting framework. OKRs, EOs, I don't care. All goal setting frameworks have the same bones. There's some description of it, there's some quantification of it, there's some work that has to be done. There's some accountability rituals with clear owners and clear agreements. **Jonathan Lowenhar** (01:01:18): So once I actually have the quantification of here's what work needs to be done, I now know what resources I need to be able to pull that work forward and therefore now I know what kind of humans I need, whether I'm hiring or renting. And that should drive the conversation, not the, "Oh God, I need another PM." It's no, here's the set of features that we've said matter most this year. Here's the gap in the resources we have and the resources we need, that's why we're hiring this role. And here's what success would look like 12 months from now or six months from now. So they're tying back to what would change about the business. **Jonathan Lowenhar** (01:01:57): And this is this recurring theme of our work with our founders. They're so in it Lenny that they rarely have time to sit above what they're working on. This notion of working in the business versus on the business. And so much of our work is to separate them from the day-to-day, which is enormously important, not in any way denigrating it, and I need to know where I'm headed and why, and how I'm going to measure progress along the way. And so, so much of what we're doing with them is to say, I want to hear from you what you think success looks like. I'm going to push back and pressure test a bunch of things. Can we define that in a way? Can we agree on who needs to do the work along the way, and how we're going to keep checking on it to keep feedback loop short? Now we can go back into business and then we'll check again in a week or in a month. **Lenny Rachitsky** (01:02:54): I love that. That's actually a great segue to the final bucket I want to spend some time on which is growth and go to market. Another area that many founders have never worked on before. A lot of founders are like, Hey, I have this awesome idea. I'm going to build this awesome product. I know how to do that. I know what market needs. But building a go-to-market motion to get it into people's hands is a whole different skill. We spent a lot of time on this on the podcast, you have a really cool simple framework of just how to think about go-to-market. There's all this like, oh, you need a go-to-market strategy. Talk about how you talk to founders about thinking about what it takes to put together a go-to-market plan and how to make it a repeatable motion versus just I'm just going to go to people and try to sell them. **Jonathan Lowenhar** (01:03:37): Our founders, even the most capable of them find this topic pretty overwhelming because it branches into so many areas. So we do try and distill it to something that is in bite-sized chunks. We think of it in four pieces. The first piece is ideal customer profile. Who do we really want to sell to? What are their qualifications? What are the discovery questions we would use to get to those qualifications? What are the kill criteria to know that this is [inaudible 01:04:10] fool's goal, this really isn't the human? **Jonathan Lowenhar** (01:04:13): Second bucket, loosely called marketing. But within that marketing is also positioning. So what is our uncommon denominator from the enemies? So who are we competing against? Is it actual companies or is it status quo in some sort? What are they great at? What are we great at? What are we great at that they're not? Then how do we represent that in the world? That's branding and artifacts and identity work, et cetera. **Jonathan Lowenhar** (01:04:44): Next is demand gen, which we'll simplify to say, how do we go find the humans we want? I've long loved the book Traction that Gabriel Weinberg... I'm going to forget unfortunately the co-author's name right now, Jason Mares? Sorry. Where they talk about the 19 channels that all companies have availability to, they're the same ones. Now the book has got a couple of years on it, so there are a couple of new channels that have popped out since, but what we then try and expand the aperture for our founders is rather than just think about meeting your next customer through however you did at your last company, availability bias, instead, which of these might make most sense next? A simple two by two matrix can work here like some experimentation, some brain writing. Love brain writing, not brainstorming. I know you've talked about that on prior pods. And then high impact, low effort. Can we think of the three or four experiments we want to run by channel? Let's go play. **Jonathan Lowenhar** (01:05:48): And then fourth, sales. And this is the codification of a playbook. How are we having the conversation? How are we doing discovery? How are we handling objections? How are we doing demo? How are we moving to close? If we can get through those four, then we can start to talk about deployment and customer success and upselling and account management, et cetera, et cetera. Those are good problems to have. Oh my god, my install base is so large, I need to manage it. Great, great fricking problem. But we try and break this complexity of going from individually selling to building a machine into just these four buckets. Who am I selling to? What do we want to say about ourselves? How do we reach them? How do we close them? **Lenny Rachitsky** (01:06:28): Amazing. I was going to summarize that. You did an excellent job there. Before we follow up on this, you mentioned this term brain writing. What does that mean? **Jonathan Lowenhar** (01:06:35): Oh, first time I heard of this was Adam Grant. I don't know if he's the originator of the idea. Brainstorming, you talked about this a bit in your Annie Duke podcast as well of how horribly coercive meetings can be. **Lenny Rachitsky** (01:06:55): For brainstorming, especially. **Jonathan Lowenhar** (01:06:56): For brainstorming especially. And so, what many of our founders don't recognize because they just see like, Hey, I'm just sitting around a table with a group of folks I respect, so we can just debate things as peers. No, you can't. You're a founder. Your voice has a megaphone attached to it even if you can't hear it. So you have to turn down the megaphone if you actually want to learn what your people have to say. So brain writing is I'm going to expose an idea and I want everyone to now write and weigh in on there... it could be in a survey, it could be in a shared doc, what have you, my preferences in through some sort of methodology, you are now sharing your opinions, comments, edits, dreams, in an async way that no one else can see until it's all combined, maybe even ideally without authorship identified. **Jonathan Lowenhar** (01:07:50): Then when the founders weigh in, you don't know, they're just a part of the mass. Let everyone read the thing. I even like the Amazon, take the first 10 minutes of a meeting, let's just go read so we're all fully present and then have a debate. What it allows for is the dampening of the founder effect in meetings. **Lenny Rachitsky** (01:08:18): You're just so full of golden nuggets. That's just like a random tangent that I think could be really transformative for a lot of teams. So the advice here is just when you're trying to ideate and brainstorm, don't go in a big room and put post- its on a wall and talk throughout ideas and have a discussion. Instead, just everyone individually sits and thinks and shares their thoughts and the founder presents, here's a problem, here's a question we're trying to tackle. **Jonathan Lowenhar** (01:08:39): What it also allows for is an evening of the playing field between fast processors and slow processors, introverts and extroverts, because they're all equally potentially talented in your room, but if you do live brainstorming, you have diminished all the folks that prefer to sit and chew on something first. **Lenny Rachitsky** (01:09:02): That's very much me. That's exactly how I operate. I need to think and process. I'm not on the spot quick thinker person. So 100% fan of this approach. Let me come back to your go-to-market framework. I have the notes pulled up here. So basically if you're a founder or even a product builder and you're trying to think about how do I... people keep telling me I need a go to market plan, I need to grow this thing. How do I think about this? You're basically saying there's these four buckets to think about; who are you selling to? How are you going to motivate them and get them excited to buy your thing? How do you reach them? And then how do you close them? **Jonathan Lowenhar** (01:09:37): Yes. **Lenny Rachitsky** (01:09:39): Luckily I have podcasts and newsletter posts on every single one of these buckets, if folks want to pursue each one of these. I have templates for ICPs, marketing advice, all these things. So that's good news. There's a lot of content for people to read if they want to explore this stuff. Let me ask you, where do you often find the biggest bang for your buck when you come to a founder or if founder comes to you and they're like, I need to figure out, go-to-market motions? Just start from the top and work your way down. Or is there, here's where maybe you want to spend a lot of time. **Jonathan Lowenhar** (01:10:10): Early stage founders, and this is certainly more true for the first timers Lenny than the veterans 'cause they learn this problem. The first timers are like twenty-something year olds in a bar and they're being social for the first time in their lives, and anyone that makes eye contact with them is enough for them to say, I want to go on a date with you. That's it. There's no discrimination of any kind, like, oh my god, they like me, I'm in. That's the mistake that hounds first timers. The veterans and those we get our hands on. Instead, we say, let's imagine you could build your perfect customer in a lab, like a Petri dish and you grew them, what do they look like? And if you have any kind of install base, I'll ask the question. I just did this with the founder the other day. They are enterprise whale hunting business. They have four large customers. **Lenny Rachitsky** (01:11:13): Wait, actually whale... okay, whale hunting in terms of large wealth person or actual whales? **Jonathan Lowenhar** (01:11:21): The extreme of enterprise selling. **Lenny Rachitsky** (01:11:23): Okay, okay, got it. I want to see a whale hunting startup. Okay, go on. **Jonathan Lowenhar** (01:11:29): I said, so which of your four customers is your favorite? Which one, if I got them on the phone, they would rave about you. They would be salivating openly with a chance to evangelize what you're doing for them. And they was like, oh, that's clear. It's this one of the four. Great. Tell me about them. And what you start to see and pull apart from that is the founder does have an ideal profile. They do have a dream. Now, there are all sorts of risks about is the world too small? Is it not a big enough market if they get too tight, and founders get so caught up in that and it's a mistake because all we're- **Jonathan Lowenhar** (01:12:00): ... so caught up in that, and it's a mistake. Because all we're looking for in the beginning is a white-hot center of opportunity, a small population that is an enormous fan that's getting enormous impact. We can worry about adjacencies and expansion later. I like to remind them that Amazon just sold books. We can start with one thing and be great at it. So where the founders often get hung up on for us is that they've moved towards selling without contemplating ideal customer profile, without contemplating qualifications, without contemplating discovery questions that get to that. And most importantly, kill criteria, if this is true do not sign them, even if they want to go out on a date with you. **Lenny Rachitsky** (01:12:48): I'm glad you said that because that's exactly what I believe and I hear often on this podcast is how underappreciated picking your customers in early leads are. And if you think about this funnel you described, figure out who you're selling to, how do you motivate them, find them and then sell them, all this trickles down from who are you going after. You will know how to motivate them if you know who you're talking to versus the opposite. If you're talking to everyone- **Jonathan Lowenhar** (01:13:11): It's the most expensive mistake of those four. **Lenny Rachitsky** (01:13:15): Okay. Is there anything else on go-to-market or growth you think might be helpful just to touch on before we close up our conversation? **Jonathan Lowenhar** (01:13:25): The one thing I'll share, this goes back to the ready, fire, aim that we talked about earlier, is that there's implicitly a funnel, mathematical funnel, to what we just described. And founders often make the mistake when planning for the year ahead of I need to be at this revenue to justify this multiple. And then all of the funnel math is a plug, and that's death, as opposed to here's what's been true for the last three months, six months, nine months, 12 months. And then what assumptions can I reasonably make with ways I'm going to influence that funnel going forward, to go build up to where I think I'll be a year from now? And it just lowers the bias that your planning process operates with. **Jonathan Lowenhar** (01:14:15): But when a founder starts from a place of, "I have to get to 3 million or we're dead," you're already dead. As opposed to what do I really believe I can do to get there, changing top of the funnel, changing conversion rates along the way, changing a deal size or deal length, et cetera based on my recent history, and then have a conversation about the gap between where I think the business reasonably can get with some ambition, and where I think I need to be financially, because that's the more mature conversation and that's the one the ready, fire, aim CEO doesn't have. That's the one most founders have only started to learn to have over the last few years when capital dried up. **Lenny Rachitsky** (01:14:57): I love that. I love just how practical and real talk your advice always ends up being. Speaking of that, I emailed a founder that you work with and asked him, "What should I ask? What should I ask Jonathan when he comes on the podcast?" **Jonathan Lowenhar** (01:14:57): Uh-oh. **Lenny Rachitsky** (01:15:09): And he said something that was really... That's great. It was really unexpected what he said. He said that the biggest lesson he learned from you is to, as a founder, to trust his intuition more throughout the journey of his startup. Can you just talk about that as something you've learned, something you've seen, that maybe founders under appreciate? **Jonathan Lowenhar** (01:15:31): It's impossible not to be a startup CEO and not face many existential moments. Is my company going to survive? Did I make a mistake? Will I ever be hired again? Should I sell the company now? Should I break up with a co-founder? Should I fire this critical employee? They happen to all of us. And fear is not a good decision maker. Our lizard brain is a really bad decision maker in those moments. **Jonathan Lowenhar** (01:16:07): And so what we'll often share with the founder who's facing one of these scenarios, and I know the CEO you're describing and he's facing one of these scenarios, we'll say to them, "Do you know that little voice when you get really still, the quiet one that says you should marry this person, you should take this job, you should start this company? Watch out for that human, they're a bad one." And most of the time, Lenny, when I frame it that way the person across me says, "Yeah, I know that voice." And I'll ask, "How do you hear it?" And they're usually some version of, "I have to get really alone, really still, really quiet, walk on the beach, listen to music, work out, play with my pet." **Jonathan Lowenhar** (01:17:06): I said that voice is who you are. It's not your brain. Your brain is a tool. It's our hands, it's our feet, just a tool. It's a pattern recognition machine. But who you are, if you can watch your brain, you know what you're thinking, like, oh, look what my brain's doing. That means you're not your brain. It's something else. And that's the little voice, and that little voice is going to be right. And where we get screwed up in life is when we stop listening to that voice, when the mania of our chaos of our lives get in the way of that voice. **Jonathan Lowenhar** (01:17:42): And so whenever our founders face one of those moments, it's not a framework, it's not a playbook, or even a directed piece of advice from us to say, "You should just go left. I've seen this before. Go left." Nope. I trust founder intuition. If the founder says this business is still going to work, or this co-founder is the wrong person, or yes, it's time to sell, I'm in. We're just here to support them. And we try and be the only person in their life that is fully on their team because we're not on the preferred side of the CAFS table. We're not fiduciary, we're not board members, not a co-founder, none of those things. And so in those moments we'll just say, "Can you get really quiet?" **Jonathan Lowenhar** (01:18:21): And the founder you're talking about, I have the story in my head, he was facing a breakup moment with his co-founder, and I asked him, because he's good at getting quiet, "What did the voice say to you way back when?" And the voice said to him, "This is the wrong fit. This isn't going to work. He believes in different things than I do, and that's going to go badly." But the lizard brain didn't want to believe that, and so it took another year. **Lenny Rachitsky** (01:18:58): Wow. I had tingles throughout that entire piece of advice. I love how it's also very applicable to just life, not even just being a founder. It's a good reminder to trust that voice more. It's interesting that this also connects to founder-mode a little bit, and I'm curious how you think about that where a lot of the founder-mode advice is like trust your judgment, don't hire people to delegate things away. Do you see a difference in the core idea of founder-mode and just like, but you should actually trust your intuition more? **Jonathan Lowenhar** (01:19:35): Intuition comes from, in my point of view, a deep understanding of self, and the capacity to get quiet and be well resourced, meaning you've slept well and you've eaten well and you have enough love in your world. And I think what founder-mode can confuse is my intuition says I should just do this job for them and fire these three people. That's not intuition, that's reaction, that's a fear response. And when the founder says, "I sat with this, I felt it out, I can see it. I need to terminate my whole go-to-market team and start over. This isn't working, and I have data that supports it, but I know this isn't working." I'm like, "Let's go with that. I'm in. Let's do it." **Lenny Rachitsky** (01:20:36): And I think you described a lot of times people feel this, and it takes a year, two years, three years, many years to actually realize that. And your advice here is try to listen to that more and trust it more. Yeah. Wow. Okay. Well, Jonathan to pivot our energy, is there anything else want to leave listeners with, last piece of advice, anything that you think might be helpful before we get to a very exciting lightning round? **Jonathan Lowenhar** (01:21:04): To be a founder is a state of being. It's an attitude, it's courage, it's instinct, it's a capacity to push through, despite all sorts of evidence suggesting you're wasting your time. To be a CEO is a craft. The more founders who can accept that those are two separate things and they're both equally important to build an ascendant startup, the better all of us will be. And so what I would encourage every founder out there that wants to go build something substantial, go work on your craft in addition to working on the business. Be honest with yourself about here's the shit I'm bad at. I don't know how to read a financial statement. My board meetings suck. Half my meetings that I have with my leadership team we all walk out of there saying what did we just accomplish right now? Or I get to the end of my workday and I'm like, I didn't get anything done. Those are all examples of just not taking the craft seriously enough. I'll leave with that. **Lenny Rachitsky** (01:22:18): I love that. And I think I've made the mistake during our conversation of confusing founder and CEO and assuming they're the same thing, and I really appreciate you just again pointing out to folks that that's the big distinction you got to start making is there's the founder and there's the CEO. Often they're same person, but different parts of your brain and different skill sets. **Jonathan Lowenhar** (01:22:36): And I'm now fully off the very awkward soapbox I've been sitting on for a long time, so we can go to lightning round whenever you're ready. **Lenny Rachitsky** (01:22:44): With that, we've reached our very exciting lighting round. Jonathan, are you ready? **Jonathan Lowenhar** (01:22:48): I'm ready. I'm ready. **Lenny Rachitsky** (01:22:49): First question, what are two or three books that you have recommended most to other people? **Jonathan Lowenhar** (01:22:54): My number one business book that I've recommended would be Five Dysfunctions of a Team, by Patrick Lencioni. I do think it always comes back to team. The right team can solve all the things. And that book is a beautiful distillation of the most common problematic archetypes that show up in a leadership group. So that's the number one. **Lenny Rachitsky** (01:23:16): Amazing. Anything else you'd recommend? **Jonathan Lowenhar** (01:23:19): The second one, it goes more personal. It's a book called Untethered Soul, by Michael Singer. It was, at least for me, the first introduction to this idea that I am not my brain and that my brain can be a tool that serves me well, and at times doesn't. So that would be number two. **Lenny Rachitsky** (01:23:38): I've started to read that book and then I never finished it, so this is a good reminder to give it another shot. Second question, do you have a favorite recent movie or TV show you've really enjoyed? **Jonathan Lowenhar** (01:23:50): I just watched and really enjoyed, because by the way, I have a three-year-old at home, so the amount of content I now consume is reduced tremendously. Well, my wife and I just watched Will & Harper. This is the documentary between Will Ferrell and his very dear friend who just recently transitioned. They road trip across the country together, and it was freaking delightful. It was sweet and endearing and one of the better things I've watched in a while. **Jonathan Lowenhar** (01:24:19): TV show, Slow Horses, I'm utterly addicted. I'm only midway through season two, but I've been voraciously sleeping less and watching more. **Lenny Rachitsky** (01:24:31): I love both those. I just watched Will & Harper, and completely agree with your sentiment about it. I wasn't planning to watch it. My mother-in-Law started watching. I'm like, wow, this is really fun. It's also funny, meaningful funny. **Jonathan Lowenhar** (01:24:43): There's so many moments in it that are really sweet. As an aside, this was '20, I don't know, April 2020, and a group of our very close friends said, "Hey, how are we going to keep in touch?" And so we started what we called Movie Club, and we routinely either pick a TV show or a movie. We all watch separately and every two weeks we get together on Zoom at night, we talk about what we just watched. **Lenny Rachitsky** (01:25:06): I love that. **Jonathan Lowenhar** (01:25:07): And some have been great, some have been terrible. But Will & Harper was our most recent. **Lenny Rachitsky** (01:25:10): Oh, such a cool tradition. Okay, we'll keep going. Do you have a favorite product you've recently discovered that you really love? Could be an app, could be something physical? **Jonathan Lowenhar** (01:25:21): Two, and one is I'm going to talk my own book, but I still love it. The first one is Aura Frames. These are digital picture frames. They're amazing. The UX for them is incredible, the quality of it, they're pieces of artwork. So grandparents, in-laws, parents, we have multiple in our house, just love it. **Lenny Rachitsky** (01:25:46): Just to clarify, it's a frame that has picked digital photos and you can give it to your mom and show photos of your kid wherever they live. Is that right? **Jonathan Lowenhar** (01:25:55): And the combination of the ease of the software and the quality of the imagery is better than anything I've tried, and I've tried a bunch of them. A-U-R-A Frames, and this is not an Enjoy The Work company. This is just one I'm a giant fan of. **Jonathan Lowenhar** (01:26:08): The second one is an Enjoy The Work company called Augie Studio. A-U-G-I-E Studio. This is Canva for video. It can turn anyone with no engineering skills whatsoever, no code video creation, with full editing tools. So suddenly you can create branded high fidelity, high quality commercial video in minutes, with no effort. It's amazing. It was built by two media tech co-founders that were building this thing pre-ChatGPT, and it's just growing like this, and it's super fun, and the guys are great. So A-U-G-I-E Studio. **Lenny Rachitsky** (01:26:51): Sounds amazing. Augie Studio, I could use that. That sounds awesome. Two more questions. I feel like this one's going to be a good one. Do you have a favorite life motto that you often come back to find useful and work on in life? **Jonathan Lowenhar** (01:27:04): The first one, and the one that I probably most commonly refer to, is that there is only one life. The quick backstory, and I know it's a lightning round, but I'm guilty of these stories. I went for a walk with a girlfriend of mine a bunch of years ago. And we did this once a month and we would always have a pretty typical ritual of giving each other life updates to begin the walk. And so I started the conversation with, "So there's the family update and then there's my work life and then there's my social life." She's like, "No, no, no, no, no, stop. That's all bullshit. It's one life. Stop assuming that there are these pretend walls between them or among them." I've lived that ever since. **Jonathan Lowenhar** (01:27:42): So I try and show up. That phrase lets me show up the same way, no matter my setting. If you and I were having a beer or a meal, or if I'm sitting with one of my co-founders or clients, it doesn't matter, I show up the same way everywhere. Part of the way I enjoy the work is by having a real friendship, a real intimacy with everyone at Enjoy The Work, and including our clients as well, I want that level of conversation. I don't want the sterile stuff over here with my work environment versus my personal versus my family. It's just one version of me. **Lenny Rachitsky** (01:28:15): And the phrase is, it's just one life. **Jonathan Lowenhar** (01:28:17): Just one life. **Lenny Rachitsky** (01:28:18): It's just one life. Final question. So you ran a casino at one point, I believe, and it was like a Harrah's Casino, is that right? **Jonathan Lowenhar** (01:28:28): My first career was in the casino business. **Lenny Rachitsky** (01:28:30): Okay. **Jonathan Lowenhar** (01:28:31): But before I go on, what's the question? **Lenny Rachitsky** (01:28:32): The question is just is there a fun story, or experience, or lesson from that time in your life that might be fun to share? Maybe a mob involvement, or cheating, or something? I imagine that's a unique life experience. **Jonathan Lowenhar** (01:28:48): I'll tell one of my favorite family stories then briefly. But yes, my family goes back in casino gambling in one form or another, several generations. My great-grandmother ran a illicit poker game. My grandfather ran numbers out of a gas station. My father's been in the casino industry since Atlantic City in the 70s. My sister is a prominent gaming attorney, and I worked in the industry for a dozen years, so this is my family. And Lenny, I didn't know any of this was weird until I was in my mid 20s. **Jonathan Lowenhar** (01:29:18): I turned 21, and I'm old, yes, I'm going to just hide the year. I'm kidding. Anyway, I turned 21 and we take a family trip to Las Vegas because that was normal for us. My father was doing a lot of work out there, so he got us hotel rooms, etc. I'd never been there before, and I was newly 21 and so my parents said, "You have $300 to gamble with. We're going to be here for five days." This is a vacation. My grandparents are coming in. My uncle and aunt were coming in, and they're encouraging me, "This is all up to you, but try not to lose it all on night number one," which was good advice to give me. I was 21 and I was pretty much a schmuck at the time. But also, part of my experience being there was to interview for a summer internship. I was a college going to be junior. So we go and I immediately go sit at some table and start playing some games. And I turn $300 into a few thousand dollars in the very first evening. And that was exciting and it was crazy and it was wild, et cetera. On the third night, which happens to everyone who goes to Vegas for too long, we're all delirious because all of us are staying up all night and being silly and being stupid. And my parents ask me, by the way, this is pre-cell phones, they ask me, "Hey, can you stay awake? Your uncle and aunt are going to arrive late tonight. They'll call the room. You can come down and just greet them and say hello?" Sure. So I get the phone call like 11: 30 at night. Go on downstairs, they're here. I go downstairs in the casino floor. We're staying at the Las Vegas Hilton. It's since been renamed, but I go downstairs and I can't find them anywhere. I think, okay, well I have cash in my pocket and I'm now awake so I might as well gamble. **Jonathan Lowenhar** (01:30:53): Shortly thereafter, Lenny, I have an experience that happens one in 369,000 occurrences, and I win $35,421.92. For the trip I ended up winning $40,000 that I turned $300 to, and I was just 21 years old, which has left me with one of my mantras that I've had for the rest of my life, which some people roll their eyes at, but that is gambling does pay. **Lenny Rachitsky** (01:31:20): I love that you remember the exact amount. What games did you end up playing that helped you win so much money? **Jonathan Lowenhar** (01:31:27): The primary game that I played was Caribbean Stud Poker, where there's no skill of any kind. You get five cards, the dealer gets five cards, whoever wins wins, and if you have particularly unusual hands you get odds on the hand. And I got dealt 3, 4, 5, 6, 7 of spades in five cards. **Lenny Rachitsky** (01:31:44): I thought you'd say slots or something. I love that you're just sitting there playing poker and went from $300 to $40,000. **Jonathan Lowenhar** (01:31:51): It's not even real poker. **Lenny Rachitsky** (01:31:53): That was a great story. I'm glad I went there. Jonathan, this was incredible. I think we've helped a lot of founders through this conversation. Two final questions. Where can folks find you guys? Who would be a good fit? What should people know about Enjoy the Work? And finally, how can listeners be useful to you? **Jonathan Lowenhar** (01:32:10): Love that. So let me unpack those three. The first one is enjoythework.com, or just find me on LinkedIn. I'm not hard to find. Send us a note. **Jonathan Lowenhar** (01:32:22): Who should ping us is very simple. If you're a founder out there, or a CEO out there, and you know in your heart that there's some gap between how you're running the business and how the company's going, and how it could be going, and how you could be running the business, if there's some gap there, we're here to help. Now our expertise, as we talked about in this call, is company building. So if you just have an idea on a napkin or you have a science experiment that you're not sure, we're useless, that's not us. But if you have some breadcrumbs worth following, like the business is starting to work, you're a series A into B and beyond, and you know that there's better, you can see it, that's where we help. Send us a note. Love to chat. **Jonathan Lowenhar** (01:33:06): How can listeners be useful to us? So we are ferocious readers. All we try and do is study how do the best startups do X? From tiny things, like how do they run all hands meetings or off sites to the big meta topics of what is going to repeatable go-to-market even mean? Or what is financial planning in a way that's useful? Or how do you set goals that won't make you roll your eyes? We consistently learn from the ecosystem of podcasters and authors and journalists, like, go look at this material. So if your listeners have a favorite X on whatever topic in running a startup, send them my way. All we love to do is read and chew on that stuff. **Lenny Rachitsky** (01:33:54): Awesome. And the best way to send that is either through Enjoy the Work or LinkedIn. **Jonathan Lowenhar** (01:33:58): That's right. **Lenny Rachitsky** (01:33:59): Awesome. Jonathan, thank you so much for being here. **Jonathan Lowenhar** (01:34:02): Lenny, this was so damn fun. Thanks for listening to my crazy casino stories. **Lenny Rachitsky** (01:34:07): I want to hear more, but we got to go. Bye everyone. **Lenny Rachitsky** (01:34:11): Thank you so much for listening. If you found this valuable you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast. com. See you in the next episode. --- ## [13/17] Seth Godin's best tactics for building remarkable products, strategies, brands and more **Lenny Rachitsky** (00:00:00): Before you came on, I asked on Twitter, what should I ask Seth Godin? The most recurring theme actually had to do with AI. How do you think all these new AI companies build brands to distinguish and differentiate themselves? **Seth Godin** (00:00:10): AI very soon is going to stop being a feature the same way electricity is not a feature. What AI companies and all companies need to do is say, what's in this for the user? What promise do I want to make a difficult promise, a remarkable promise, and then how do I keep it? **Lenny Rachitsky** (00:00:26): You wrote a new book. You basically talk about how a great strategy has tension at the center of it. **Seth Godin** (00:00:31): Tension is at the heart of every art form and every innovation. What we do when we launch a new product, we say, we have this thing that can do X, and now the person is imagining what their life might be like if that were true. If they fall in love with that possibility, now there's tension. Did you tell the truth? Is it going to work for them? **Lenny Rachitsky** (00:00:51): There's the section that stuck out to me, these four insights that basically determine what your life is going to be like outside of actually building the product. **Seth Godin** (00:00:59): For a product person, these are the critical choices and you probably have glossed over them. **Lenny Rachitsky** (00:01:11): Today my guest is Seth Godin. Seth is an absolute legend. He's published 21 books, including 18 international bestsellers. He's been blogging every single day for almost 10,000 days in a row now. His writing and his advice have inspired me and so many people all over the world for the past few decades. He shares wisdom and advice around stuff that everyone can benefit from, including how ideas spread, when to quit, how to lead, how to stand out, and most of all how to change everything. In addition to his writing and speaking, Seth has founded several companies, including Yoyodyne and Squidoo. He also started the altMBA program, and as you'll hear in our conversation, he actually started his career as a product manager. In our conversation, Seth shares advice on how to know if you have good taste and how to build your taste, how to build a brand in an increasingly crowded world of AI startups and AI content, his thoughts on the Jaguar rebrand and also the Tesla Cybertruck. **Lenny Rachitsky** (00:02:10): We also delve into his new book, This is Strategy, including why every great strategy has tension at its center, why you need to understand the systems within which you operate in order to build a great strategy and how choosing your customers, your distribution strategy, and how you validate your idea will inform the product you build and the life that you live. We also talk about how he used Claude as a writing assistant in developing this new book. **Lenny Rachitsky** (00:02:33): This episode is short and packed with insights, which I know is what you all love. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and helps the podcast tremendously. With that, I bring you Seth Godin. **Lenny Rachitsky** (00:02:52): Seth, thank you so much for being here and welcome to the podcast. **Seth Godin** (00:02:55): What a treat, Lenny. Thank you for having me. Lenny was my late mom's nickname, so it's good to say that out loud. **Lenny Rachitsky** (00:03:02): That's so cool. I've never heard it used for a woman, and every Lenny out there I've met is wonderful, so I imagine she's wonderful. First, I just want to say how honored I am to have you on this podcast. When I actually started this podcast, I was like, and I was listening to you on Tim Ferriss at that point, and I was like, man, what if one day I get Seth Godin on my podcast? How cool would that be? I've read so many of your books. I have a bunch of them in the bookshelf back there. I reference your stuff all the time, so thank you again for doing this. **Seth Godin** (00:03:29): Well, thank you. It's a treat to talk to you. **Lenny Rachitsky** (00:03:33): Today's episode is brought to you by DX. If you're an engineering leader or on a platform team, at some point your CEO will inevitably ask you for productivity metrics, but measuring engineering organizations is hard and we can all agree that simple metrics like the number of PRs or commits doesn't tell the full story. That's where DX comes in. DX is an engineering intelligence solution designed by leading researchers, including those behind the DORA and space frameworks. It combines quantitative data from developer tools with qualitative feedback from developers to give you a complete view of engineering productivity and the factors affecting you. Learn why some of the world's most iconic companies like Etsy, Dropbox, Twilio, Vercel, and Webflow rely on DX. Visit DX's website at getdx.com/Lenny. **Lenny Rachitsky** (00:04:25): This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers and automate compliance for SOC 2, ISO-27001, HIPAA and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to Vanta.com/Lenny. That's Vanta.com/Lenny. **Lenny Rachitsky** (00:05:18): I want to start by asking a question that one of your former colleagues suggested I ask you. Wes Kao. I imagine you remember Wes? **Seth Godin** (00:05:25): Of course. Wes and I sat in a room just the two of us for years. **Lenny Rachitsky** (00:05:29): So what she suggested I ask you, and this question I love, is she... I asked her, what did you learn most from Seth Godin working with him? And she immediately said, it's helping her build better taste and increase her standards, having really high standards. So I want to ask you first of all, just how do you know if you have good taste and high standards and then how do you build good taste and higher standards? **Seth Godin** (00:05:54): Great question. Thank you, Wes. I define good taste as knowing what other people want just before they do. So if you're the only person who wants peanut butter covered licorice, you're entitled to eat peanut butter covered licorice, but you don't have good taste because everyone else thinks that's weird. And people, whether they're jazz musicians or fabric designers are seen as having good taste when they bring something to the world that the world didn't necessarily expect but is glad to see. **Lenny Rachitsky** (00:06:25): What do you find helps? So Wes learned from watching you that she realized, okay, my standards are not nearly as high as they could be. Other than working with you, maybe that's the answer is work with people like you that have really high standards. Just what do you find is most helpful in helping people build taste and also just increase their standards? **Seth Godin** (00:06:46): Standards, it's worth understanding what quality is and the people who listen to this podcast know better than most. Quality is not luxury. Quality is not perfection. Quality means meeting spec, and if you meet spec, you're done. If you don't think the spec is good enough, make a better spec. But if you meet spec, you're done. And so what it means to have high standards is that you relentlessly improve the spec in service of the people you're working with and for. **Seth Godin** (00:07:16): And what it doesn't mean is that you take something that meets spec and refuse to ship it because you're a perfectionist. That's hiding. And so what I learned at Spinnaker where I had my first job, real job as a product manager, was this idea that we weren't there to make perfect for us. We were there to delight the person who was buying the software. And our standards were untouchable. We said, "If that person, the one we're describing is delighted with what we shipped, it's good. And if they're not, it doesn't matter what kind of excuses we have." This is the opposite of what most people in this job do, which is they say, how do I please my boss? And if you're just doing your job, then don't expect to get rewarded for more than just doing your job because we can find lots of people who can just do your job. **Lenny Rachitsky** (00:08:10): That reminds me of one of your other really powerful pieces of advice about how no matter your job, this is a tangent, but it really stuck with me once I read your advice here is no matter what job you have, you couldn't love it, enjoy it, be amazing at it, even if you're just like a waitress or whatever. Can you just talk through that? Because that's so powerful. **Seth Godin** (00:08:29): Well, I think I got it from the late Reverend Martin Luther King Jr., and the idea is there's no perfect job. A friend of mine, Tim, is a famous jazz saxophonist and he's got to schlep from city to city, and he's got to play to half empty rooms and he is got to deal with this and deal with this. So you're never going to have unlimited artistic freedom. But what we all have is the ability to understand where the boundaries of our work lie and go there. **Seth Godin** (00:09:01): And if you're a barista and you've chosen to be a barista, maybe because it's the best thing you could get, well you're not going to get the next hour over again. So what would it be like to be the best barista in the world for an hour? Would that be worth it for you? Because I've had menial jobs in food service and I got to tell you, when the boss forces you to be mediocre and bored, there's no amount of money they can pay you to do that job. But if you're there and you have a chance to add delight to someone's day, you're doing that for you, not because you're getting paid. **Lenny Rachitsky** (00:09:34): And you could totally tell these people in the world when you go to a barista that just you can tell, just loves their job. I know imagine she knows this is not her career long-term, but she just embraces it and just has fun with it. There's so much power to that. On a different note, you mentioned that you were product manager, which I did not know. That's amazing. So most of the people listening to this podcast are product managers. They're either product managers, founders, people that want to be founders, and then people that work with product managers. So first of all, I guess could you just share that part of your life? Because I don't think people know that. **Seth Godin** (00:10:05): All right. So the origin story could take all day, but I'm not going to tell the whole thing. I'm going to tell the part that I thought was normal that turned out to be the luckiest thing in the world. The summers between the two years of business school are very important to establish your career arc. I got a job at Spinnaker Software. Spinnaker invented educational computer games. I was the 30th employee. And the summer was spent doing assistant brand manager kind of stuff, going to meetings with the ad agency, writing copy. But at the end of the summer, they had a lovely going away party for me, because I was flying back to California. And then at the end, the president of the company, the chairman of the company and the head of marketing bring me into this side when they say, "We have a secret project, we want you to work for us while you're at business school and we're all going to pay you almost nothing." **Seth Godin** (00:10:52): "Okay, what's the secret project?" "We're going to do computer adventure games with illustrations and music based on science fiction novels, and we've already acquired the work of Ray Bradbury and Arthur C. Clarke." Now, I had read every science fiction book in the Clearfield Public Library from Asimov to Zelazny. This was a dream come true, but they thought my job was going to be make the packaging and run the ads. And what I discovered, first of all is that I couldn't really go back to business school. So I showed up hardly at all at Stanford and just took a lot of red eyes. But I discovered that the engineers, the development team, they had a lot of people vying for their time. And if I didn't figure out how to get them to give me way more than my fair share of development, I wasn't going to have any products to make next Christmas and then I was going to be out of a job. **Seth Godin** (00:11:46): And so I started a newsletter internally, I was one of the first people in the world to have desktop publishing because I was a beta tester for the Mac, and in it I would mention anybody in the engineering team who had worked on my project and I would say something good about them. And then I would print it out and put it in every single person's inner office mailbox. And within three months, four months, partly because the project was really good, 40 engineers were working for me and no one was reporting to me. And so I became the de facto product manager and that is when I learned marketing is the product. You don't make a product and then hand it to some marketing yahoo and say, go put a logo on this. That the product we made, and five in a row went gold, saved the company. Though product is why it worked. **Seth Godin** (00:12:38): And so I was supposed to know how to code but I didn't, but I could be in the room. The last month, RadioShack had bought how many units? 3000 stores times five times five, a lot of units. And if we had missed a date, they were going to cancel the order and the company would go bankrupt, and the software wasn't even close to done. And we didn't have any source control like we do now. There was no cloud, so it was all in my head. So I did not leave the office. I'm not exaggerating this, I did not leave the office for the last 22 days, slept for four hours a night upstairs, and if anyone had a question, I could tell them who to talk to. **Seth Godin** (00:13:19): That was so thrilling. It was so thrilling to make those decisions, to cajole this team, none of whom were in it for the money, to make something we were proud of. And then the stuff ships, everyone else goes home to sleep for a month, but I am the project manager and the marketing guy, so I got to stay at work. And the next day the phone rings and it's Herbie Hancock on the phone, the great jazz musician, and Herbie says, "The receptionist said you're the person in charge of Fahrenheit 451." And I said, "Herbie? I'm 24 years old, man. Herbie?" And he went on and on about how he had stayed up all night to play it and that he loved it. **Lenny Rachitsky** (00:14:00): I love how natural of a product manager you were in these things you shared of just thinking everyone deflecting credit and all these things. It's sign of a great PM. Along these lines, I wanted to ask actually, so you're a PM early on. Now, you obviously spend a lot of time marketing. I know you're saying there's obviously a strong connection between the two, but is there anything you find that people building the product most often miss or misunderstand that just annoys you or do you think they need to hear? **Seth Godin** (00:14:26): Maybe I got seven, but I'll try to do them off the top of my head. The first one is this, empathy is not about kindness and empathy is not an option. This is something that you are making for other people. So the whole idea of RTFM, read the manual, I'm angry at you. If you're saying that to your customers, you made a mistake, they did not make a mistake. **Seth Godin** (00:14:49): The second one is that the thing about projects is when you run out of time and you run out of money, the project is over. Don't run out of time, don't run out of money. Good intentions are no reason for an extension. The professional doesn't ask for an extension because the professional understands that things you didn't expect are going to happen. That's part of the deal. **Seth Godin** (00:15:14): And I guess the third one would be for software, particularly software as a service, if you don't build the network effect into what you are making, you are almost certainly going to fail. You cannot hope that Apple's going to pick you, promote you, and magically have you be successful. The question is, will this work better for my users if they tell other people about it? And if the answer is no, then why would they tell other people about it? And if they don't tell other people about it, no one's going to hear about it. But if the answer is yes, then your marketing problems pretty much solved. **Lenny Rachitsky** (00:15:51): I feel like each of these is its own book that we could talk through. And I want to come back to this last point and how it relates to the purple cow. I want to spend a little time there, but first I'm going to ask a marketing question. So before you came on, I asked on Twitter, what should I ask Seth Godin? He's coming on my podcast. I got a flood of suggestions. The most recurring theme actually had to do with AI. Actually the co-founder of Intercom asked this question and it echoes what many people are wondering. So his question is how do you think all these new AI companies build brands to distinguish and differentiate themselves in a world that's increasingly filled with AI companies, AI products, AI content? **Seth Godin** (00:16:26): Well, the first question is what's a brand? Because it's not a logo. A brand is a promise. It's what do I expect from you. It's would I miss you if you were gone. And Hyatt Hotels has a logo, Nike has a brand. The way we know this is if Nike opened a hotel, we'd know what it would be like. But if Hyatt decided to make sneakers, we have no clue. They might be comfortable, but that's all we would know. And so if you want to build a brand, you got to stand for something and you got to say what you don't do. And the second thing is AI very soon is going to stop being a feature the same way electricity is not a feature. That lots and lots of things run on electricity, but they're not electricity companies. They just happen to use electricity. **Seth Godin** (00:17:13): So what AI companies and all companies need to do is say, what's in this for the user? What promise do I want to make? A difficult promise, a remarkable promise. And then how do I keep it? So making absurd promises might work at the VC level, but it doesn't work when you're talking to consumers because you can only break that promise one time. And so to wrap up the brand part, airlines don't have brands and airlines don't have loyalty. And the way we know this is that the only reason people stick with an airline is for the points, which is bribery. Loyalty is would you pay extra to stick with this? And if you wouldn't pay extra, then the brand has no value. **Lenny Rachitsky** (00:17:58): I love this phrase, make a promise and keep it. And the AI element, that raises the bar because many more promises are being made, fewer promises are probably being kept. So is the advice there, continue making an ambitious promise and then the key is actually deliver on that and that's what builds you brand? **Seth Godin** (00:18:15): Yeah. I have a very emotional connection to Claude.ai. I think they have a brand. ChatGPT's reputation with me is not good because it regularly over promises and under delivers and it does it without kindness or humility. Whereas Claude, I don't know how they did it, at least in my experience, brings kindness and humility. So when it doesn't know, it's very clear and it's not lazy and it's not angry at me. And so I happily pay extra for Claude because it has a brand. Whereas ChatGPT for me is just a tool that I use if I have no other options. **Lenny Rachitsky** (00:18:55): I love the Anthropic/Claude's billboards. "We're the ones without the drama." The AI company without the drama. I was going to save this to the end, but let's actually talk about it. So you mentioned somewhere that you actually use Claude to help you write this book and refine the book, which I think is going to increasingly happen. Could you just share that process of how you did that? What did you do that might be helpful to people to help you write this book? **Seth Godin** (00:19:20): Well, to be clear about my brand promise, because it's true, every word that has my name on it, I wrote. Every blog post, every book. I don't have a team. This is my whole staff is me. What I did with Claude and which I encourage people to do in the book is I would upload a list of four things and say, what did I miss? And it would suggest three things to complete the list. And often they would be things I hadn't thought of. And then I could go write about that or I would upload a couple chapters and I would say, what are the claims I'm making here that you don't think that I'm sustaining? And it became this patient editor that is so hard to find in the real world because editors aren't paid enough and given enough time to do their job right. And what I find is if I have a sentence that doesn't sound enough like me, I can ask Claude to help me figure out why that's true. **Lenny Rachitsky** (00:20:24): I love that tactic of using it to figure out what you missed. I feel like you agree with this. I find that when I write, part of it is I'm putting an idea out there. I want to see what I got wrong and what I missed. And I like that you basically skip that step and don't put it out and just make the thing you put out actually better. **Seth Godin** (00:20:42): Well, the thing about blogging every day is at first it felt like how am I going to keep up? But once I could build a queue because I didn't want my streak to end- **Lenny Rachitsky** (00:20:55): How long is the streak at this point, by the way? **Seth Godin** (00:20:58): Post number 10,000 comes out at the beginning of 2025. **Lenny Rachitsky** (00:21:02): Oh my God. In a row. **Seth Godin** (00:21:04): In a row. Some days there were two. But what I found as I got a little bit of a queue is that I would feel bad because I had something to say, but I couldn't because there was already one in the queue. So I shifted from I have to write something to I get to write something. And now because I've taken the pressure off, I have time to rewrite it because I don't have a shortage of ideas for tomorrow. I have extra ones. **Lenny Rachitsky** (00:21:34): This episode is brought to you by Paragon, the developer platform for building native customer-facing integrations with third-party apps. Our native integrations on your product roadmap, whether it's to ingest context from your user's external data and documents, or to sync data and automate tasks across your users' other apps, integrations are mission-critical for B2B software products today. But building these integrations in-house cost and average of three months of engineering according to the 2024 State of Integration survey, which results in difficult roadmap trade-offs. This is why engineering teams at Copy.ai, AI21 and over 100 other B2B SaaS companies use Paragon so they can focus their efforts on core product features, not integrations. The result, they've shipped integrations seven times faster, all while avoiding the never-ending maintenance that comes with rolling your own integrations. Visit useparagon.com/Lenny to see how Paragon can help you accelerate your product's integration roadmap today and get $1,000 in credit on their pro and enterprise plans. That's useparagon.com. **Lenny Rachitsky** (00:22:41): So let's talk about your book. You wrote a new book. It's called This is Strategy. I've been reading it over the past week and I've been so into it that I actually left it at my mother-in-law's house. I don't have it with me. So it's called, This is Strategy. It's about how to build strategy and develop a strategy. There's a lot to love about the book, but the section in the middle that is what most stuck out to me that I want to spend a little time on. You have this four sequence of advice that I love, so I'm just going to read it real quick. Choose your customers, choose your future. Choose your competition and choose your future. Choose the source of validation and you choose your future. Choose your distribution, and you're also choosing your future. Can you just talk through these four insights, these four steps that basically determine what your product and life is going to be like outside of actually building the products directly? **Seth Godin** (00:23:31): Yeah. And for a product person, these are the critical choices and you probably have glossed over them. You have probably assumed it's a given and you've sacrificed your agency over the four most important things you should be choosing. So the first one is picking your customers. If your motto is you can pick anyone and we're anyone, if your hope is that you have to win SEO to get anything, you're not going to succeed. When you choose your smallest viable audience, what language they speak, how much money they have, what problem they're trying to solve, what their technical facility is, whether they're short-tempered, whether they're kind, whether they're going to stick with you, you have chosen everything that's going to go into the product and what your future is going to be like. And so the Humane Pin people, whatever it was called, made a mistake when they picked their customers because they showed up like they had a finished Apple-quality product and they were trying to appeal to the kind of people that would buy on pre-order a finished Apple quality product. **Seth Godin** (00:24:40): When they shipped something that wasn't that, and they knew it wasn't that, they're doomed. Whereas if you say, here we are in Product Hunt, we're only looking for 400 people. We're looking for people who like the Raspberry Pi. Who wants to wonk with this thing? Now you can dance and you can have all these other things happen because you picked a different customer. If you decide to be a wedding photographer in the Hamptons, well you better expect to have some very spoiled, cranky brides and grooms, and grooms and grooms, and brides and brides, that you have to deal with because you picked your customers. Okay, so then the second one which comes with that is who's your competition? Because if you're competing against Walmart, why are you surprised that they keep lowering their prices? That's what Walmart does, right? That way you decide which space that you're going to operate in. You've built an enormous set of boundaries around what you do. **Seth Godin** (00:25:36): The third one is validation. If you are trying to please your boss, that's what you're going to do. If on the other hand, you can have one difficult conversation with your boss and say, can we agree that I'm not trying to match your taste, I'm trying to match the taste of these 400 people that we've agreed are our customers? Every other meeting is going to go way better from now on because you've made it clear who you're trying to please. **Seth Godin** (00:26:01): And the last one, choose your distribution matters a lot in the software business. For example, a video game, which is where I started, we were in Target and Lechmere and mass merchants. Our competitors were in Ziploc bags in computer stores. Well, when something like Steam shows up, when something like downloadable shareware shows up, everything about your product changes. So again, these four things are choices, and if you're glossing over them it's because you're afraid. **Lenny Rachitsky** (00:26:33): And I think it's important to note, it's not like you can just change these at will and just like, okay, cool, we'll change your distribution. These are intertwined. But the important point here that I hear is just make sure the product you're building understands this is how you'll be distributed. This is who you're selling to. **Seth Godin** (00:26:49): Yeah, I mean, so a friend just sent me a business plan. They're making a food product and they're saying, we're going to distribute on Shopify and we're also going to sell to businesses, airports, hotels, and people who need to sell the food. I'm like, there's only two of you. No, that's not what your business... You got to pick, today, before you even turn the page, who are you for and who are you not for? **Lenny Rachitsky** (00:27:15): Along the lines of picking your customer reminds me, a friend of mine started a company selling a product to real estate agents and she just warned me, be careful who you're selling to because you're going to be spending a lot of time with these people. Make sure you're ready to be doing that. **Seth Godin** (00:27:28): One of my very first books was a advertising supported directory paid for by law firms. This is not something I want to recommend to anybody. **Lenny Rachitsky** (00:27:38): Another great nugget from the book that really stood out to me is this idea of tension. The importance of tension. You basically talk about how a great strategy has tension at the center of it. Why is tension so important to a good strategy? **Seth Godin** (00:27:53): Okay, so let's agree that tension and stress aren't the same thing. Stress is generally not good. Stress is two things at the same time, I want to leave, I need to stay. Right? I hate my boss, but I need this job. That's stress. Don't look for stress. Tension is at the heart of every art form and every innovation. Tension is it might not work. Tension is da-da-da-na-na, and the other person says, da-da. Because they need to finish the sentence. **Seth Godin** (00:28:23): So what we do when we launch a new product is we say, we have this thing that can do X, and now the person is imagining what their life might be like if that were true. If they fall in love with that possibility, now there's tension. Did you tell the truth? Is it going to work for them? And when I was a kid, PF Flyers were the sneaker to get, this was before Nike. And the promise of PF Flyers was that they would finally make you fast enough to run away from the bully. And I remember 10 years old walking into that shoe store and there was real tension in my head because I needed to get away from that bully, and I was keeping the PF Flyers people to their promise, and they didn't tell the truth. **Lenny Rachitsky** (00:29:08): It comes back to your point about not delivering on the promise that you make to build- **Seth Godin** (00:29:08): Yes. **Lenny Rachitsky** (00:29:13): ... A great brand, right? Okay, I want to take a little tangent into Purple Cow territory. I have your book right here, by the way. I have many of your books in the back, but I don't want to make my library... Oh, what is that? A milk carton? **Seth Godin** (00:29:26): This is the first 10,000 copies came in milk carton. **Lenny Rachitsky** (00:29:28): Oh man, I missed out on that. Was there any purple milk inside? What color is a purple cow's milk? We'll never know. We'll never know. I know you've talked about this concept a gazillion times. I feel like still people don't actually... Many people haven't heard it. Many people don't truly understand it, and it's the thing that I reference most of your piece of advice. Could you spend a little time just chatting about this topic of the Purple Cow, the importance of being remarkable? **Seth Godin** (00:29:57): Okay, so let's start with Steve Blank. I'm sure you've talked about his idea of customer traction. The single best way to tell if a startup's got any hope whatsoever is do the people who engage with you stick around? Do they come back for more? The second piece is, do they tell their friends? And if they tell their friends, what do they say? The word remarkable means worth making a remark about. So I'm not talking about coming up with some viral video that's ridiculous in its gimmickry. I'm saying if you make something where the person's life gets better if they talk about you and you know in advance what you want them to say, then they are more likely to say it. So Marissa Mayer probably created more stock market value than any other product manager I can think of. And the way she did it was there weren't very many people at Google, but she was the one who said, "No, you can't put another button on the homepage. There are only going to be two buttons on the homepage." And over and over and again. **Seth Godin** (00:31:04): At the time I was at Yahoo. Yahoo had the chance to buy Google for $10 million while I was there. That's a whole interesting story. But Yahoo had 183 links on the homepage and Google had two. And the statement built into that is we are making you a promise, and the promise is we are smart enough to take you where you want to go without you spending a lot of time browsing through 183 links. Tell us what you want and we'll take you there. And so I was a tech-forward person, and if a friend came to me lost on the internet, confused about something, I'd just send them to Google because I knew they wouldn't come back to me for more help, because okay, fine, they're gone. It's going to work. That's what to say about Google at its launch is, hey, just type in what you want and you'll find it. They built that into the product. That makes it remarkable because I wanted to tell other people about that because it would raise my status as a tech innovator. **Lenny Rachitsky** (00:32:05): And the implication here, and you talked about this, is that most likely the way you will win is word of mouth. It's hard to win with paid ads. It's hard to win with sales teams unless you're building B2B software. What you need to focus on is how to build something people tell their friends about. And the core of that is being remarkable. And I love just the way you break it down. Being remarkable is being something people remark about. **Seth Godin** (00:32:30): Yeah, and if you think it's just for small companies, that's how Microsoft beat WordPerfect, because Microsoft Word was the format you needed your coworkers to work in if you were using a modern computer, because if they insisted on using WordPerfect, then you were stuck with WordPerfect. Whereas they had a migration path and once you migrated, you didn't go back. So again, it's in my interest to insist you use Word. So I did. **Lenny Rachitsky** (00:32:58): This point about Mercer Mayer of doing this thing that was controversial, it comes back to your point of creating tension. It feels like it created tension both with visitors and internally. There's also these quotes that I have here that are along these lines that you've said in the past, I don't think they're in this book. If it scares you, it might be a good thing to try. And safety is risky. Is there anything you want to say there? **Seth Godin** (00:33:22): Well, so one of the things I talk about in the book is that systems are everywhere we look and they're largely invisible, taken for granted. I spend time with high school seniors talking about college. They don't see the college industrial complex. They just think it's normal, because that's what it is to grow up in the suburbs. And what systems do to protect themselves is they invent culture. Culture is the way things are around here. And so if you think something is scary, that's probably because the system wants you to think that. **Seth Godin** (00:33:57): And so you shouldn't do something foolhardy. You shouldn't be fearless. But what you should do is think about why does it scare me to do this? What system will be offended if I do that? Am I trying to work with the system or am I leveraged enough to help change the system? And so the first people who put up downloadable software, all the feedback was, you can't do that. It'll be pirated. You'll never make a penny. Okay. That might happen, and I can see why that feels scary, but I could also see why the dominant system of software distribution doesn't want me to even experiment with this. But I only worked on the software for five months, let's try it, because if it doesn't work and it gets pirated, I'll just have to make new software. It's okay. **Lenny Rachitsky** (00:34:44): It's interesting, the opposite of that was also true with Salesforce. Their whole pitch was no software. It's all in the cloud. Once that became the system, that became the tension and the risky move. **Seth Godin** (00:34:55): Yeah. **Lenny Rachitsky** (00:34:56): So you have this quote, actually. I want to spend more time on the system concept because it's so core to the book, and so core to your advice for how to be better, you have this actual quote. "What does it mean to be a strategic thinker? It means to see the system." What else can you share about it just for people that are trying to become better strategically, to understand what you mean when you talk about the system, how to see the system? **Seth Godin** (00:35:18): We have to invent systems anytime we engage with other human beings, because interoperability is essential. There's a system for how we greet other people in our culture. You shake hands, right hand to right hand. And just show up sometime and give the Vulcan salute instead and watch what happens. It's very awkward because we just needed to get this over with and now that's part of the system. And so systems serve a valuable function until they don't, because then the system starts doing things to support itself, to reinforce itself. So for example, there is a system that says we should interview people for jobs. And the most successful interviews are people where they show that they are like us, they look like us, they went to schools like us, they have privilege and background like us. That is toxic, because it diminishes not just diversity, but our ability to put real talent on the team. **Seth Godin** (00:36:19): And if you don't see that system and name that system, you're going to keep doing what you were doing. And I was talking to someone yesterday who said they had been working with a company and the last four people that they had hired had been captain of their Ivy League tennis team. Well, clearly there's a pattern here and it's being reinforced by people who don't want to get in trouble, but the system's not helping them. And so yes, we need the metric system and we need the zip code system. Those keep working really well. But if you are trying to show up in a place where dominant players don't want you to succeed, you're going to have to find something in the system that gives you a chance to change the rules. **Lenny Rachitsky** (00:37:07): This metaphor that I love that's along these lines of better waves make better surfers, that a lot of your success is driven by choosing the wave versus the skills that you have. Can you just talk about that? **Seth Godin** (00:37:18): Yeah. So it's surprisingly profound. I don't know where I came up with it, but when I see people who are great at surfing, they're almost always on good waves. And my son who surfs a lot, I have noticed, passes up waves that other people might take waiting for the right wave because he knows he will be able to surf it better. So when you think about which company you're signing up to bring software from, which people you're willing to put on the key roles, are you willing to wait for the superstar who's going to change things or are you in so much of a hurry to make an imaginary deadline that you're going to ship mediocre work? Because all mediocre means is average. And so if you don't want to be mediocre, you better do something different than the other people are doing. Otherwise, you're going to get what the other people are getting. **Lenny Rachitsky** (00:38:10): As you talk about this, I'm thinking about, I don't know if you saw Jaguar's rebrand and their whole launch. And it feels like it's been rejected by the system. Any thoughts on that? Maybe what they got wrong or maybe it was genius? **Seth Godin** (00:38:24): Okay, so you've picked a topic that I really like to talk about. Jaguar did not rebrand, Jaguar re-logo-ed. And the logo might be a sign that they're trying to rebrand and make a different promise, and they're switching to all electric, which I'm in favor of. But they made, I think, a very significant error, which is if you're going to start a car company, a hundred million or a billion dollars are going to get spent earning trust from people who never heard of you. If you're starting with one of the most iconic and beautiful and beloved car brands that has the luxury of having almost no cars in the world that could undermine what you want it to stand for going forward, it's perfect. Own that, that's brilliant. And to walk away from that so that you could please some art director, I don't understand why you think you're rebranding when you just put a logo on that undermines many of the awareness assets you already had going for you. **Lenny Rachitsky** (00:39:28): It feels like they got very, very controversial. They went against the status quo more maybe than they should. I don't know. What would you have done if you were them? **Seth Godin** (00:39:36): You may recall when the International House of Pancakes decided to falsely announce they were changing their name to the International House of Burgers and made a new logo, because they wanted buzz. This is a Wendy's Twitter tactic. Buzz does not sell hamburgers. Oreo's got a lot of buzz when they did that tweet about the Super Bowl blackout. There's no evidence they sold even one more cookie. They're not in the business of entertaining us. So Jaguar isn't going to sell more cars because people like you and I are talking about their re-logoing. What's going to make them sell cars is customer traction. What they need to do is find 50 people who have authority and get them in a car that changes them somehow, that transforms them. **Seth Godin** (00:40:26): And it's interesting if you think about two things that Tesla did right at the beginning with the model S. The first one is, according to someone I know who worked there at the time, the number one thing people would talk about when they saw you in the parking lot of the supermarket was the door handles, because the door handles popped out. They popped out in a way that's annoying and dangerous, but it was noticeable. So there was a conversation. **Seth Godin** (00:40:52): And then what would happen is they'd say, what do you think of it? And you'd say, get in the car and you'd switch to ludicrous mode and you'd drive at zero to 60 in 2.4 seconds and they'd start screaming. This was fun for you and told a story to the passenger. This is how customer traction begins because I can't do that in a different car, right? Compare this to the clown car, the Cybertruck, which was intentionally divisive and most people don't want to not only drive one but have one on their block because divisiveness is not selling. That what's selling is being of utility, to help someone get what they want. So here you have a category, the pickup truck, the number one category for all cars in the United States, just sitting there waiting to be taken. You can cross the chasm if you're someone like Tesla. And instead, they decide to pull a stunt, and that's not okay. It's not good product management. It's not good marketing. **Lenny Rachitsky** (00:41:56): Interesting. So you think Cybertruck are not going to be a success? **Seth Godin** (00:42:00): Well, I think, compared to what, right? So the Ford F-150 some years has made more than a hundred percent of Ford's profit, meaning without the Ford 150 pickup truck, there is no Ford. That's how big a category that is. You have a car with momentum and a public company where you've earned the trust of a lot of people. Now you have a category, pickup trucks, that are purchased for a very specific reason to show your neighbors you care about utility. Even if you never use the bed, that's the story of driving a pickup truck. So now, if you bring people in that category who are inherently skeptical of change and inherently skeptical of design trickery, something that is nothing but change and design trickery, no, they're not going to adopt it. You could have sold an enormous number of people who might've bought a Ford 150 instead. That crossing of the chasm is how you become really significant. **Lenny Rachitsky** (00:43:01): I feel like this alone could be its own separate podcast conversation. I wish we had more time. I'm going to ask one last question, and this is a quote that I found of yours that I also love that is reminiscent of Elon Musk, actually, as we were just talking about this. "The secret to leadership is simple. Do what you believe. Paint a picture of the future. Go there. People will follow." Can you just talk about that? **Seth Godin** (00:43:25): I might be a little too glib because what I need to highlight is the painting the picture of the future needs to be based in empathy. You can't paint a picture of where you want to go. You have to paint a picture of where they want to go, and it's this non-narcissism that is where professionals do their work. That you are not entitled to raise money, you're not entitled to have market share, you're not entitled to get a good price because you worked hard. What we can do is be of service. We can open the door to help people get to where they always wanted to go. It's very difficult to change what people want, but it's pretty helpful to offer people a chance to get to where they always wanted to go in the first place. **Lenny Rachitsky** (00:44:14): Seth, this was a dream come true. I appreciate you coming on the podcast. I appreciate you saying that. Where can people check out your book? Where should people go to learn more about what you're up to? Anything you want to share. **Seth Godin** (00:44:25): So I'm not active on social media, but I do have a blog at Seths.blog. If you go to Seths.blog/TIS, you'll find everything you need to know about the book and the strategy deck and the collectible chocolate bar and whatever other thing I've dreamed up in the meantime. **Lenny Rachitsky** (00:44:42): Chocolate. Seth, thank you so much for being here. **Seth Godin** (00:44:45): These were great questions, Lenny, I could talk to you all day. Thank you, **Lenny Rachitsky** (00:44:48): I appreciate that. Same. Bye everyone. **Lenny Rachitsky** (00:44:52): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at LennysPodcast.com. See you in the next episode. --- ## [14/17] Behind the product: Duolingo streaks | Jackson Shuttleworth (Group PM, Retention Team) **Jackson Shuttleworth** (00:00:00): ... Duolingo is a $14 billion company, it's hitting all-time highs too, it just keeps going up, but I think it doubled in value in the past six months. Streaks is the most impactful feature. We have, right now, over 9 million users with a year plus streak. If you look at the numbers, I think it's been our biggest growth lever. What Duolingo really focuses on is, how do we help users build habits around language learning? Getting user come back the next day is the biggest problem to solve. **Lenny Rachitsky** (00:00:25): Let's get into the motherload of learnings from the journey of streaks, talk about the key lessons, insights, and also wrong turns along the way. **Jackson Shuttleworth** (00:00:30): I'd say test everything, we've run in the last four years over 600 experiments on the streaks, so every other day. We've actually set up really good infrastructure for copy testing. We used to say continue, our standard CTA is continue, and we changed that to commit to my goal, and it was a massive win. **Lenny Rachitsky** (00:00:48): There's so much human psychology that you all learn through all these experiments of just how to motivate people, what motivates, what demotivates. **Jackson Shuttleworth** (00:00:55): Say that you played a mobile game, or that you've done it for 3,000 days in a row, I don't know, maybe that hits a little bit different than you've learned Spanish for 3,000 days in a row. **Lenny Rachitsky** (00:01:07): Today, my guest is Jackson Shuttleworth. Jackson is a group product manager at Duolingo, leading the retention team. This is a different kind of episode that I'm experimenting with, where we spent the entire conversation focused on the journey and lessons of a single feature, in this case, Duolingo streaks. Duolingo is a $14 billion business, just over the past six months, they doubled in value, they're hitting all time highs in usage and market cap, they're also one of the very few successful and also the single biggest consumer app business in the world. And as you'll hear from Jackson, the streaks feature is the single most impactful feature that most contributed to this growth and success. In other words, you could argue this one feature created billions of dollars of value, which to me means it is worth studying in depth. **Jackson Shuttleworth** (00:02:48): Yeah, thank you. Long time listener, first time caller. **Lenny Rachitsky** (00:02:52): I appreciate it. So, this is going to be a really interesting conversation, I've never done an episode like this before, where we basically spent an hour, an hour and a half going into one feature of one product, but this is a very special feature, it's a very special product. Have you ever spent an hour, an hour and a half just talking about this one feature with anyone? **Jackson Shuttleworth** (00:03:13): Well, internally, so when we onboard new folks to the team, we'll do, I actually just did this with somebody that joined the team recently, where we spent, yeah, I was like, hey, let's spend an hour just talking about the streak. We got through an hour and I got through about 30% of what I wanted to share, there's just so much, we'll talk about this, but there's so much that we've learned over the years, but never anything externally like this. I think we've shared bits and pieces of learnings, but this will be the motherload of learnings hopefully- **Lenny Rachitsky** (00:03:14): Here we go. **Jackson Shuttleworth** (00:03:41): ... of how Duolingo built the streak. **Lenny Rachitsky** (00:03:42): **Speaker 3** (00:05:05): Pendo. **Lenny Rachitsky** (00:05:10): **Jackson Shuttleworth** (00:06:10): Well, presumably people know, Duolingo is a language learning app, the Duolingo streak tracks, currently anyway, how many days in a row you've done a lesson. So, you come to Duolingo, you do a lesson, your first lesson you'll start a streak, and then every consecutive day that you come use the app, you'll extend your streak. And I should actually put an asterisk around how many days in a row because we also have built flexibility into the feature. So, we have these things called streak freezes, it's like insurance for your streaks. So, it's a pretty simple feature, in theory, but over time we've layered on challenges, and goal setting, and rewards, and social features... A lot of our notifications are tied to the streak. So, pretty simple feature to understand, but it's been a really rich feature for us to build on top of. **Lenny Rachitsky** (00:06:58): Some people might be hearing this and be like, Duolingo streaks, what's the big deal? There's other people that are like, holy, I want to learn everything I can possibly learn about Duolingo streaks, so many companies are trying to copy what you've learned from this. Give people a sense of the impact that this one feature has had on Duolingo's success and growth. **Jackson Shuttleworth** (00:07:15): And this is not just the subjective retention PM talking, I think this is our biggest feature, with the exception of the lessons. And I think it's actually [inaudible 00:07:24] start that. Streaks are a great engagement hack. I'm of the opinion that any team, any app out there can introduce a streak, and if you figure it out, it probably works to retain users, but at the core, you have to have an app that people want to use, and people really like using Duolingo. It's fun, it's delightful, you learn something. And so, it allows us to layer an engagement mechanic on top of that the streak is really powerful. So, it ships a disgusting amount of DAUs, again, it is one of our golden geese. And again, what's cool is that, you look at notifications, notifications for Duolingo is massive. Us sending better, whether it's copy or timing, so many of our notifications work because they reference the streak, because users care about the streak. **Jackson Shuttleworth** (00:08:10): And so, not only is it itself, us iterating on the streak a huge driver of DAUs, but it's also something that enables other really high valuable features. I was looking up some stats before I came on, and it's pretty crazy. So, we have right now over 9 million users with a year plus streak. **Lenny Rachitsky** (00:08:30): Wow. **Jackson Shuttleworth** (00:08:30): So, 9 million of our users have used Duolingo every year, almost every day, for well over a year. Which is pretty... I don't know, I like to imagine things in terms of like, okay, well, if you put all these people in a city, or in a place, where would it be? I'm like, ah, it's like a very large city, 9 million people. **Lenny Rachitsky** (00:08:53): For a year, have a year long streak. **Jackson Shuttleworth** (00:08:53): For a year. **Lenny Rachitsky** (00:08:56): That's incredible. I was just looking at the stock of Duolingo, so Duolingo is a $14 billion company at the time we're recording this. It's hitting all-time highs too, it just keeps going up. I think it doubled in value in the past six months, something like that. And what I'm hearing from you is streaks is, other than just the core learning feature, which is just the product of Duolingo, this is the most feature in terms of growth, and in that retention specifically. **Jackson Shuttleworth** (00:09:24): If you look at the numbers, I think pretty objectively has been our biggest growth lever for driving DAUs, and also say a lot of it's just related to how we think about growth at Duolingo. And a lot of what we try to do is organic growth. We think about growth just as much as bringing new users onto the platform is not losing them. If you're just bringing people onto the platform, then they churn, that's not going to be sustainable. And so, as much as we can do to keep our users coming back and actually retaining as users, it's going to give us a much easier base to continue growing DAUs off of. **Lenny Rachitsky** (00:09:57): Perfect. Okay. Talk about how this feature originally came to be. What was the original version of it? What was the original insight that led to [inaudible 00:10:05]- **Jackson Shuttleworth** (00:10:04): Yeah, so the oldest streaks or as old as Duolingo itself. When we launched Duolingo, we launched with a streak... And I say we, I was just graduating undergrad when Duolingo launched. So, this is well before my time. But we launched with a streak feature. Initially how the feature worked was you'd come to Duolingo and you'd set a goal for yourself, and it was an XP based goal. So, Duolingo, a little bit of nomenclature, we have an experience point based system that drives a lot of our features in the app. And the way you'd set it is you'd say, based on what your language learning goal was, maybe you have a 10 experience point goal versus a 50 experience point goal. And so, extending your streak would be, hey, can you hit 50 experience points? If that's what you set your goal to be. **Jackson Shuttleworth** (00:10:50): And this worked well, I think this also speaks to how Duolingo initially grew. Luis launched it with a TEDTalk, we probably had a more tech-forward user base initially, and so this whole idea of an experience points based streak system made sense. But what that also meant is that you could have a user come and use the app, do multiple lessons a day, and maybe they just set too hard of a goal for themselves, and then lose their streak. Which, you don't need to be an expert in streaks to understand that's probably not good. The nice thing with how we initially set it up though is it really did connect with what your goal was. So, if you were serious, let's track how good you are at being a serious language learner. **Jackson Shuttleworth** (00:11:28): But I'd say one of the most impactful experiments we ran was about, this was actually as I was joining, or just after I joined we had run this experiment, was to move it from a XP based streak to just do one lesson a day, and you'd extend your streak. And the risk that you can sort of imagine is, well, then users kind of care less about it because it's not connected with their goal. And we saw none of that. This was a huge driver of DAUs, just making it easier to extend your streak, but I think really importantly it's still meaningful. The unit of use, and as you're thinking about building a streak, I think it's really important to think about what the unit of use of your app is. The unit of use for Duolingo is doing a lesson. And so, if what we care about is users coming back every day and doing a lesson, because it shows that they're actually engaging with the app, then it doesn't hurt us to make our streak focus on just do one unit versus multiple. And so, that was probably the big [inaudible 00:12:25] change experiment that we ran at the time was moving from an XP-based streak to a one lesson streak. It's also simple, and I think that's one of the things to think about with streaks. It's always easy as a PM to have a million goals or objectives for what you want your feature to be and potentially build a more complex feature, and a one lesson streak, it's just easy for more users to understand. **Lenny Rachitsky** (00:12:46): Yeah, that's exactly what I was going to say. And just for folks that aren't super familiar with XP, it's basically experience points and you get them from doing things, it's like a [inaudible 00:12:53]- **Jackson Shuttleworth** (00:12:53): Yeah, you do stuff on Duolingo, and then based on what you did and how well you did it, we give you experience points, this actually drives a number of our features in our apps. So, leaderboards is the big one, we have a leaderboard system, where you try over the course of the week, you battle with 29 other people, and you want to win, that's all driven by XP. So, we do have other features in the app that really benefit from this XP system- **Lenny Rachitsky** (00:13:16): Cool. **Jackson Shuttleworth** (00:13:16): ... the streak is just no longer one of them. **Lenny Rachitsky** (00:13:18): Awesome. Okay, so I want to talk about the journey from that point to what it is today, but a quick tangent, I saw Luis tweet just this week, someone asked him, "How do you decide whether to optimize for learning or engagement?" And he's like, "No question, everything we do is focused on engagement because you won't learn anything if you're not coming back to the app." **Jackson Shuttleworth** (00:13:39): As an engagement PM, that was the coolest thing he could have ever said. It's, well, again, very much as subjectively I guess as an engagement PM, that's how I've... I am sure the learning folks at Duolingo will cringe when they hear it, I see myself as a learning PM as much as an engagement PM, because the easiest way not to learn on Duolingo is not to come back the next day. And so, if we don't make the app retentive, you will have no opportunity to engage with our learning features. Now, I do think that there is a long tail of learning, where, if you start to dumb down, and honestly this is something we wrestle with the streak as well, you start to dumb down the experience, and your users aren't actually learning, they're not going to care. **Jackson Shuttleworth** (00:14:20): Streaks work best when they're sitting on top of an app that users care about. But yeah, if you don't come learn on Duolingo.... If you don't come back to Duolingo, then you're not learning. We track a lot of this with, the work that we do, we make sure that as we're making changes to the streak, we're not hurting the learning experience and we don't have a ton of interaction with it. So, we're constantly thinking about this, but thank you Luis for saying that. **Lenny Rachitsky** (00:14:48): It makes sense to me. Okay, so lets get into the motherload of learnings from the journey of streaks. So, the first version went from XP to one lesson, talk about the key lessons, insights, and also wrong turns along the way to what we see today. **Jackson Shuttleworth** (00:15:03): Duolingo has very much, has a strong test it philosophy, we're willing to test a lot of different... Honestly, we'd much rather test it than debate it for days and days. So, we actually followed up this experiment with, and this is a little bit later, with hey, what if we make it even easier to extend your streak? And so, we actually tested, hey, if you do one exercise, just one exercise in a lesson will extend your streak. A lot of the insight was good, you look at the funnel, hey, there's a lot of users who are starting but not finishing lessons, they're not extending your streak, the loss aversion doesn't kick in, they don't come back... So, this followed that train of thought. What we realized when we ran this experiment is DAUs moved not one bit. And what we were doing by... And if we go back to unit of measure, we had dumbed down the unit of... Nobody thinks about, oh, I just want to come do one question on Duolingo, nobody thinks about that. **Jackson Shuttleworth** (00:16:05): So, we had a less clear unit of measure that we were basing our streak around, and the users that we were capturing with our streak, you come, you do one or two questions on Duolingo, then you leave, were the least engaged users imaginable. And so, I think that's something also to think about as you're building your streak, is like what is the user that you're solving for? So, not only what is the habit that you're building for, but what is the level of commitment, and that was an example where we over indexed on a type of user who we honestly just weren't going to keep, that was a very easy shutdown decision. **Lenny Rachitsky** (00:16:39): That's an awesome story, just to comment in that real quick. Just you went, let's just go to the extreme and make it just like streaks, yeah, get everyone going streaks forever, and then... I love that it turned out and it's not bringing users that you want, and it's dumbing down experience. It makes me think of Farmville, where you have to go and harvest your crops every, whatever, hour, that lasts for a bit and then eventually people are like, what the hell am I doing with my life? **Jackson Shuttleworth** (00:17:04): Yeah, exactly. We test every, I was looking at the numbers as well, we've run in the last four years, over 600 experiments on the streaks. So, every other day effectively- **Lenny Rachitsky** (00:17:14): 600, wow. **Jackson Shuttleworth** (00:17:15): ... we're running an experiment. And they range from big, like this, changing how the mechanic works, to let's swap a string with another string and see if that copy is better for users. So, we're constantly testing on everything. I do think that, I'd be more careful running that experiment now, at some point your streak gets big enough that, again, I got 9 million users on the streak, I got to be really careful... Those are our best retaining users, you got to be careful. But in the early days of the streak, I'd say test everything. See what... Don't get super caught up in it has to be like this, just test a bunch of stuff and see what speaks most to users. Because I think, again, you will constantly be surprised by the insights that you get from whether you... We shut down about half of our experiments, so half of our experiments lose, we still learned a ton by virtue of running them. So, super, super valuable. **Lenny Rachitsky** (00:18:08): That's actually a good success rate, a lot of companies have only 20% of experiments be positive. What's your policy on if it's neutral, do you ship it, or do you kill it? **Jackson Shuttleworth** (00:18:18): It really depends. If we're adding something and it's neutral, we tend to shut it down because it's just more cognitive load, it's something that we're going to have to start building around, a new UI element that we have to figure out how it fits into our system. I'd say when we do ship a neutral experiment is, something that we have real conviction around, okay, yeah, maybe this was neutral but it's going to give us a new platform to then build on top of, so that experience might be neutral, but now we can build these DAU positive experiments. My general take there is though, in that case, build that in as part of your V1 so that you make sure that at least your hypothesis around this roadmap has play should probably be the case, but in general, shutting down a neutral experiment so you don't introduce more complexity to the app is the way we tend to go. **Lenny Rachitsky** (00:19:10): Makes sense. All right, what else? What else have you learned along the journey? **Jackson Shuttleworth** (00:19:13): Well, maybe I can talk about a few different ways that we structure, a few different themes that I think we lean on. So, the first is focusing on the zero to seven day user experience. And I would say this is, if you look at whatever our breakdown of experiments are, we run definitely more than average number of experiments on getting users to go from a zero to seven day streak. And a lot of this is because we've looked at the data for our retention curves, and what we found is that once you get to seven days, loss aversion kicks in, and you retain. So, going from a one to a two-day streak, huge jump in retention, two to three day streak, slightly less but still huge and it's up until day seven. Once you hit day seven, it flans out. And it's not to say that if you have a 30-day streak, you're way more attentive than day seven, but not in the order of magnitude that it is from day one through seven. **Jackson Shuttleworth** (00:20:05): So, we do a ton of work to get users to that point where loss aversion kicks in, and then they don't want to lead the app. One of the fun ones that we did, and it's honestly as much about process as it is about the feature itself, was we have a feature called streak goal, and it is... Again, so much of this stuff seems so obvious in retrospect, but it was really novel at the time. We had this idea of like, hey, maybe we'll just goal users to hitting a certain streak length. As you can imagine, this is pretty powerful user psychology, and we started with the simplest version of this. And this is how Duolingo does a lot of our testing. Rather than design the big complex feature for V1, just do the simplest encapsulation of what that feature can be, see if it has legs, and then just add to it iteratively over time, this is partially how we get to 600+ experiments on streaks, they're not all big ones. **Jackson Shuttleworth** (00:21:01): But we started... And it was funny, we actually took a learning from our monetization win teams. One of the strings that they had, the pieces of copy that they had, worked really, really well was, I think it was your 5.6 x more likely to finish the course if you subscribe to Plus. Now, it's Super, our subscription. It was a really good hook that if you really cared, you'd sign up. And so, we had a similar thought, where it's like, oh, let's just tell you how much more likely you are to finish the course if you get a 30-day streak. **Jackson Shuttleworth** (00:21:34): And so, we started with that, and I think it was like you're seven times more likely to finish the course if you have a 30-day streak, and just that message when you started your streak, I telling you that, was awesome. Huge win. Indicating an outcome... And Duolingo doesn't have, we have a gem economy but we don't actually have, it's all you learning. But being able to actually talk about it in terms of the outcomes that a user would think about, in this case, trying to finish the course, was a huge win. So, this is where we started and we're like, ah, goal setting, all right, we should go much harder on this. **Lenny Rachitsky** (00:22:06): Found a- **Jackson Shuttleworth** (00:22:06): Yeah, we found our thing, and now let's just beat the heck out of it. So, we followed that up with another experiment, where we tested different lengths. So, we test 14 days and 50 days, and we found that they were all good, but they appealed to different users. And so, we started to realize, all right, well, we probably need to be more thoughtful about who we give these different options to. And so, then we followed that experiment up with, all right, let's start with 30 days, and then we're going to let you opt out, we'll say, no, I don't think I can hit it. And our thinking was, and then if you say no, we'll hit you with an easier goal. Because we just wanted to get you to commit to a goal. And this was a fascinating one because it was a good win to give users that easier goal, to try to capture them before they said no, but it was almost just as big a win to add that opt out button. **Jackson Shuttleworth** (00:22:58): So, we tested separately, and I'm a huge fan of testing way too many arms for an experiment, just to be able to isolate your hypotheses, but we captured just what happens if we add an opt-out button, and adding an opt-out button... And you would think, as a PM, oh, now users might not engage with my feature, that's a bad thing, but it was a huge win to let them do that. And the learning here was that this intentionality of saying, no, I want it... Previously it was just a continue button, but now it's like, no, I want to hit 30 days, and having that be an intentional decision for them, yes or no, even though again, this had no impact, or no impact past this screen. Everything that I'm talking about now was just that screen that day, and then was all thrown out. So, that optionality was a huge insight, and so because of that, we built a goal setting feature where you could choose between different goals, giving users that optionality was likewise a huge win. **Jackson Shuttleworth** (00:23:57): I'll say one final learning on this, again, you talk about friction, and good and bad friction, we thought once we built a goal picker screen, where you could pick between different streak lengths, we were like, oh, well, let's recommend that users do a harder goal, thinking that okay, well, a harder goal is going to be better retention, and we'll the preselect harder goal for them. And based on all the learnings that I just shared with you, you probably imagine lost pretty significantly, we realized that yes, we could speed users through the screen more by virtue of picking a goal for them, but that act of selecting, I think it's 30 days, I think it's 14 days, was where we were getting so much of the engagement from this feature. **Lenny Rachitsky** (00:24:39): There's so much human psychology that you all learn through all these experiments of just how to motivate people, what motivates, what demotivates, it feels like you guys should write a book on human psychology and motivation. **Jackson Shuttleworth** (00:24:51): I feel very much like a amateur armchair psychologist with everything that, at least as far as people who want to learn languages on their phone go, I really understand those folks. **Lenny Rachitsky** (00:25:03): Right. So, one theme I'm hearing here so far is you guys are basically just mining for gold, just looking for a vein in some mine, and once you hit it you're like, ooh, this worked, you just go crazy on just testing all kinds of things to see how far you can take that one little thread. **Jackson Shuttleworth** (00:25:22): Yeah, and I think, I shared how this idea came partially from a monetization win that they had, I think there's a lot of, because Duolingo runs... I don't know what percentile we're in, but it's got to be a very high percentile of per capita experiments run for a company, based on company size. We're just constantly learning so many things and there's a really great cross-sharing of monetization say, hey, this thing worked for us, is that something you can use? So, I'd say it's rare that we go into something where it's just like, let's just try something. Typically, we have some insight because of all of these experiments that we've run, that hey, if we do this, I don't know, it's one here, or it's worked here, it's driven this user engagement, if we massage that and try in this scenario, or a different screen, we come in at least with a strong hypothesis of this will work. **Jackson Shuttleworth** (00:26:17): A lot of times we do look, and we're like, a lot of the apps that we look at actually are games themselves, so it's like, all right, you're playing Royal Match, or there's the new Pokemon trading card game that I'm spending way too much time on, you look at these games and see what they're doing, and it's really good fodder for what we can do. But a lot of times you're at least going in with a strong hypothesis based on what you've seen work elsewhere. **Lenny Rachitsky** (00:26:39): Got it. So, just to double down on that point, it's not just random experiments, it's here's a hypothesis we're fairly confident, or has a chance to be true, let's try it. It's not just let's just try everything? **Jackson Shuttleworth** (00:26:49): Yeah. And I think that how strongly you feel about the hypothesis directly ties to how hard that experiment is. With copy, for instance, we've actually set up really good infrastructure for copy testing. I'm of the opinion that companies should run, as long as you have the user base to do it, copy test constantly. The amount of copy tests that we've had that have won, and I don't know, you just try things and you figure out what wins is definitely legion, and [inaudible 00:27:15] massive wins from little copy changes. **Lenny Rachitsky** (00:27:18): Is there an example of that, of just the impact? **Jackson Shuttleworth** (00:27:20): Going back to that goal screen, we used to say Continue, our standard CTA is Continue, and we changed that to Commit To My Goal, and it was a massive win. And again, it was like, okay, users tapping on that, what are we asking them to do? Commit to the goal, what is that going to lead them to do? Commit, not churn. Just that little copy change, that one time, right there, led to huge wins. And copy changes are so cheap, it's just you translate, for us, we have a lot of users all over the world, and a lot of UI languages, but just come up with a bunch of ideas, translate some strings... This is one where the feedback that you'll typically get from Luis. So, all of our changes at Duolingo go through product review that are reviewed by Luis, so Luis reviews every single change that we propose, every experiment that we run. **Jackson Shuttleworth** (00:28:12): Typically with copy, he's just like, I don't know, test it, there's nothing better than be told by Luis, I don't think this is going to win, but sure, if you want to. And a lot of times, to his credit, he's right, and a lot of times our intuition was right, but it's just so cheap to do it. I think when the lift is smaller, it's great to have a hypothesis, but you don't need to beat it up too much. **Lenny Rachitsky** (00:28:36): So, on this thread, I didn't realize Louis reviews everything you're planning to change, and this may be the answer to the question I was going to ask, which is, one of the criticisms of running a product and company this way, of just experimenting constantly with all these micro improvements and changes, is it can lead to something, like a monstrosity of a product and experience that isn't consistent and cohesive, and just that often happens. Is the solution to that having the founder basically review all the changes? Is there anything else y'all do to avoid it becoming Farmville or whatever, is a good example of that? **Jackson Shuttleworth** (00:29:06): Yeah, our product review structure where we've got our head of product design, one of the lead, the product management leaders, and then Luis, NPR. And because they see everything, and they have a really high product bar, and so that helps. I think over time we just, as PMs, have to look at, okay, where is our feature headed? And so, we do this with the streak at least on a quarterly basis, to look at, okay, well, what have we learned, how has our streak developed, and how do we imagine this going in near future? It's easy to do, and in some sort of awful local maxima, if you're not constantly looking at your roadmap and you don't have a clear strategy. For me it's like, if you have a clear strategy where your feature is going, hopefully all of those A/B tests are not just done to get some cheap gain, they're done with a long-term goal in mind. **Jackson Shuttleworth** (00:30:03): I do think though, and we do this every now and then with the streak, eventually you just hit a local maxima, and you say, you talked about launching neutral experiments, this is a great example, where it's like all right, cool, now we need to throw a bunch of this stuff out, based on all the learnings, can we reset this real estate, can we reset this UI, reset this feature, in such a way that is just as good as what we have now but is way more plain or simple, that we can, again, start to layer on? Those are really hard experiments to get to win obviously, because they are so optimized, but they're really important to do, otherwise, yeah, you just end up with a kitchen sink of a feature. **Lenny Rachitsky** (00:30:39): One other tidbit I just want to mention, an advantage you all have that other companies don't have is people want to learn a language, and so getting pushed to come back to an app for something that they want to do, it's not an advantage a lot of products have. So, anything you want to add there, of just like this is why Duolingo might be a little different from what you're working on. **Jackson Shuttleworth** (00:31:03): That is definitely a benefit, if I had an app... And that this is actually why I think a lot of mobile games do streaks differently, because to say that you played a mobile game, and as somebody who plays a lot of mobile games, that you've done it for 3000 days in a row, I don't know, maybe that hits a little bit different than you've learned Spanish for 3000 days in a row. I think the comparison set is much larger though, than a lot of companies give themselves credit for, and I think that there's... There's a lot of ways that companies think about their... There are very few companies I imagine out there in the world saying, oh, we don't do some degree of good for our users... Even if it's like a game, it's like, I don't know, you're giving somebody a moment away from the craziness of their lives. **Jackson Shuttleworth** (00:31:47): And so, I do think though that is contingent on companies who are going to figure out if a streak works for them, to figure out how can you frame the streak in such a way that a user does feel good about it. And it's easier for a Duolingo, but I think there's creative ways to phrase this for users. The other thing maybe just on that that I'll say is, the streak works really well for Duolingo because with language learning it's really hard to see day-to-day progress in becoming more fluent. And fluency is not even the right word, it's like becoming better at Spanish or whatever, it is a years long process for someone to get better at a language. **Jackson Shuttleworth** (00:32:25): Duolingo makes it easier, but you still got to put in thousands of hours if you're going to reach C1 or C2 fluency, and that is really hard to track on a day-to-day, and so the streak works really well for us because we might not be able to tell you, hey, you now know 0.01% more Spanish, but we can show you, hey, you've gotten your streak a little bit higher. And so, I think this works particularly well when you're an app that is doing something that's going to be sensed or felt over a longer term to help contextualize that progress in a way that makes more sense, or at least feels more tangible to a user. **Lenny Rachitsky** (00:33:02): Great, that was a great context. Empowering to a lot of companies that aren't necessarily doing language learning. Okay. So, it took us on a long tangent away from lessons and experiments you ran along the journey of iterating on the streak. So, a few things you've shared so far is just, it started with this XP idea, and then went to a lesson, then you iterated on ways to make it simpler, maybe harder, you added streak goals, where you commit to I'm going to hit a certain goal of streak. What else? What else have you found that has worked, didn't work, lessons learned? **Jackson Shuttleworth** (00:33:32): Again, sticking with this one to seven day streak, the idea of a streak, particularly probably to this audience, is obvious. Like, oh, it's a streak, it just counts how many days. We've realized over time that a lot of users do not understand how a streak works, and it can be as small as, well, I don't understand how streak freezes work, or I don't... Like my mom the other day was talking to you about it, she's like, "Oh, I didn't use Duolingo and I come back and my streak's still there." So, there's certain elements of the feature that we can do better at explaining, but even what a streak is, it's tracking how many days that I've used the app, yeah, the more that we can make the feature easily comprehensible to users, the more retentive it is. And we've run a number of experiments to do this. **Jackson Shuttleworth** (00:34:23): You asked about early easy copy changes that we made. Actually, this is my first win experiment when I joined Duolingo was, when you start a streak, we have little copy at the bottom of the screen that just, I don't know, it's like flavor copy, we use it to celebrate you, or give you context, and I ran some tests that just tried to in eight words explained what a streak was, that was it. And it was a massive win because it really dumbed down here is exactly how the streak worked, and it really helped users just understand what they needed to do. And I think this is something that's like, you constantly got to remind yourself, particularly if you work in tech and you're building cool tech features, but your user base is not a bunch of tech workers, to think about, all right, who is my audience? And for us it's not just tech workers, it's not people in America, it's people all over the world of all ages of all cultures, and so making sure that your feature is even something as simple as the streak is understandable is critical. **Lenny Rachitsky** (00:35:27): What was the actual copy, do you remember? **Jackson Shuttleworth** (00:35:29): It was... I think it's still on the app, it's like, "Start a day to extend your streak, but miss a day and it resets," something like that. **Lenny Rachitsky** (00:35:38): That makes sense to me. Very clear. **Jackson Shuttleworth** (00:35:40): Yeah. **Lenny Rachitsky** (00:35:41): In eight words, I love that. Okay. And then, when you say massive win by the way, just to give people a reference point, what does that look like? What is a massive win in this scale? **Jackson Shuttleworth** (00:35:50): Well, and it's funny, and this was four years ago, but I think it was in the order of magnitude of over 10,000 DAUs for us, and actually, maybe a small bit of context. So, Duolingo really cares about the metric CURR current user retention rate, and actually our first ever Duolingo post with Lenny was the newsletter that our former head of product wrote, Jorge. **Lenny Rachitsky** (00:36:11): Still the single most popular newsletter post of all time in my newsletter, across 300 plus- **Jackson Shuttleworth** (00:36:15): I would highly recommend that if you were interested in this, give it a read. To summarize, basically, what we found is that, if we wanted to drive DAUs, and Duolingo cares, our growth North Star is DAUs, the metric that is most effective, where a percentage change in that metric is most effective at driving DAUs is current user retention rate. And this is just users who are not new or resurrected, getting them to come back tomorrow. And so, most of the work that our teams do, our retention-based teams do is focused on CURR. And so, the retention team that I lead focused on CURR, it just so happens the streak is the best feature at driving CURR. And so, this experiment was the biggest CURR win that we had had, and it was like a top three CURR win, anyway for us. Just this little copy. And that's why I say, test copy 1000 different ways, sometimes it's not the big beautiful feature that's going to drive the huge gains, sometimes it's just something simple as a few words. **Lenny Rachitsky** (00:37:15): I love this. Okay, so you said 10,000 DAUs, I think that references you guys measure incremental impact and absolute numbers of new daily users you're going to drive attributed to that experiment, is what it sounds like. **Jackson Shuttleworth** (00:37:28): Yeah, and we do both. We'll also look at, a lot of times I'll look at, for retention, day one versus day seven versus day 14, a lot of what I'm looking for is for us to have a better day 14 impact than better day one impact because it means that users are retaining better over time. This is particularly for users that would see a feature multiple times. I just like absolute DAU numbers because as long as you're controlling for different biases, like a recency bias or a novelty bias, it's a really easy way to just have an absolute comparison. You start to look at percentage changes and then it's influenced by who your treatment, how many users saw the experiment, but at least an absolute number is easier, in my mind, to start comparing.. Again, there are pitfalls with it, but we find that that's a pretty useful way. **Lenny Rachitsky** (00:38:20): That lesson comes up a lot on this podcast, and that approach to experiment. **Jackson Shuttleworth** (00:38:25): [inaudible 00:38:25]. **Lenny Rachitsky** (00:38:25): So, yeah, you're in good company. Quick tangent, if there's not an answer to this, no problem, coming back to the idea of just experimenting like crazy and not creating a product that nobody wants to use anymore, is there an example of an experiment that was positive that you all decided, no, we don't actually think this is what we want in the product, they ended up not shipping? **Jackson Shuttleworth** (00:38:47): Retention doesn't only work on the streak, although you would think... Most of our work is the streak. We've touched a lot of different surfaces over the years and there was one experiment that we launched that, we talked about XP earlier, in the lesson, the only UI elements are a progress bar at the top, and then how many hearts you have. So, we keep it really simple, and this very much speaks to the design philosophy of Duolingo, which is simpler UI is better, and we decided, hey, let's add XP in there. And so let's show your XP ticking up as you're going through a lesson, that's going to make the user feel good, it's going to show you what you've earned, you're going to be less likely to quit, all of these good reasons to do it. And then you finish the lesson and then we'll show you've collected all this XP. **Jackson Shuttleworth** (00:39:29): And it won, the hypothesis was a good one. But we realized, and I remember having this conversation with Luis, is like, cool, this is our most important screen in the app, it is our lesson, it is where users learn, and the focus here is on learning. And now you've added this other thing up there that could be distracting for users. And I think the question, we talked about roadmaps and strategy here, the question that he had for me, and I didn't have a good answer for at the time, was like, so what else are you going to do with this? What's your iteration ideas? Where's this going to go? Is this going to make the lesson experience more gamified? And what we realized is that, honestly, it was just an easy engagement win idea, but we had touched our most sacred space in the app to do that. **Jackson Shuttleworth** (00:40:16): And so, that was a case where it's like, yeah, it was a nice win, but we'd added that UI element, and at least at the time it was less clear what we would do with it and we realized that long term it was just going to get in the way, and we'd rather, for simplicity's sake, pause that, shut it down, and keep the lesson to be a little bit of learning sanctuary it was. Now, it's funny, nowadays I think we actually have enough XP based mechanics and fun things that we can do, that I think actually a lot of the beliefs about the in-lesson experience have changed, such as something like that could work, but at the time didn't feel good to keep that around. **Lenny Rachitsky** (00:40:56): That is an awesome example. Hopefully we have time to talk about how the team operates, where my mind goes is like, oh, but you have all these PMs and teams that want to show impact, and the performance reviews, and all that stuff, and you're not shipping something, they're like, oh look, we did a win. So, I want to chat about that later, but let's keep going on things you've learned and things that didn't work along the journey. **Jackson Shuttleworth** (00:41:15): The other thing that I'll call out with the streak, it's like we have the... The image of the streak is this flame. And we have the streak flame, and it's very much core to our iconography. It's important to acknowledge that that's a metaphor for a retention mechanic. The idea of keeping a flame lit. And again, I think we've established the flame is for a lot of users as sort of their understanding of a streak, which is great, but there's a lot of people in different cultural context and different stages of life, where the idea of keeping a flame lit to show your commitment to something makes less sense. We did some UXR in India many years ago, and this was something that just did not resonate at all there, which was a really interesting learning. And that's something it's like, again, depending upon what your user base is, the more global UXR you can do to understand how users are actually understanding and experience your feature, the better, because you just, again, encounter insights like this. **Jackson Shuttleworth** (00:42:12): And so, even our screen design, we used to have a flame, it was mostly this flame that would light up every day. But again, it was like an indication of a metaphor for a mechanic, and when we redesigned it, we did this, Kurt, one of our animators, did this awesome odometer animation where it's like your number would tick every day... It looked good, but from a product perspective, what was cool is we actually focused the design on the screen to show your number going up, and then it would say seven day streak, eight day streak. And I think that as you're thinking about designing around a streak, don't get too caught up into what is this the beautiful story that you're trying to tell, at the expense of it being a really comprehensible feature. And so, as you're thinking about product design, making that product design a clear distillation of this is what we're actually tracking, form should follow a function here, was a learning for us. And you'll see that now in a lot of places where we're showing streak, we're really leading with the number, not necessarily the flame. **Lenny Rachitsky** (00:43:18): That's a theme that I'm hearing again and again is clarity, don't obsess with making it too clever, and don't ever think it, just clarity has a big impact. **Jackson Shuttleworth** (00:43:29): Clarity also doesn't have to come at the expense of delight. And this is something where you hit a milestone and Duo gets, it becomes, we call him a Phoenix Duo, and he becomes awesome, and lights on fire, and I think there are things that you can do to still make the experience really exciting and delightful and celebratory, and I would not lose that, but just don't do it at the expense... And I think it's also about figuring out, you can get away with doing more of this for users who are deeper into their streak experience than users who are starting, where it's like your goal for the one-day streak user is just to make sure, do they understand how this feature works? **Jackson Shuttleworth** (00:44:06): Even something... Again, just another random experiment. At the bottom of the streak screen we have a calendar, and over the years it just looks more and more calendar-like, and that is simply because we find that the more we make it look like a calendar, days on top, little circles, the check... The more we make it look like calendar, the more that people realize, hey, this is a daily mechanic. And so, think about the screen holistically, but every single thing that you're doing on the screen, how can you use it to communicate what is the point of this feature? How does it work? **Lenny Rachitsky** (00:44:37): **Jackson Shuttleworth** (00:45:52): It is. Actually, I'm going to show you one of the most thoughtful gifts that anybody has ever given to me, this is our Duolingo Serenity, or Streak Serenity Prayer, my co-lead, Antonia- **Lenny Rachitsky** (00:45:52): It's like knitted, right? **Jackson Shuttleworth** (00:46:05): ... [inaudible 00:46:05] this for me. It's amazing. **Lenny Rachitsky** (00:46:06): Wow. **Jackson Shuttleworth** (00:46:06): And so it says, "Luis, grant me the serenity to accept the flexibility I need, the courage to reach perfection when I can, and the wisdom to celebrate regardless." **Lenny Rachitsky** (00:46:14): Aw. **Jackson Shuttleworth** (00:46:15): And that actually is kind of our strategy with the streaks. **Lenny Rachitsky** (00:46:19): I love the show and tell by the way, that was great. **Jackson Shuttleworth** (00:46:20): Yeah. Well, I guess for podcast listeners, we'll have to get an image somewhere. This idea of flexibility versus perfection, and then regardless, celebration, is core to how we think about the streak. Because I think for the streak for us, it's very much a bend not break. If you're going to miss a day, I'd rather you come back, having missed that day, to an intact streak, but if you don't have to miss a day, I'd much rather you don't, I'd much rather you come back and use the app every day. So, that thing on flexibility though, that's almost certainly been the biggest, from a mechanic perspective, the biggest DAU driver. One of the earliest experiments we ran was going from you used to only be able to have one streak freeze and then we let you have either two or three. So, we tested two different arms. It was, again, another huge DAU win. This actually is funny, it was something that... And this is, again, a callback to that growth model post from Jorge. It actually was really bad for CURR because we were basically saying, hey, you can take a day off, and that's okay, but it was really good for, this is going to be like Alphabet Soup, [inaudible 00:47:31], a weekly active user return rate. So, basically, users who had taken a day off, we were getting them to come back more at higher rates, and so it made up for our losses in CURR. But effectively, what this meant is that, why two streak freezes work better than one was, I don't know, sometimes people just need a little bit more flexibility than one day. But again, the really interesting insight of this experiment was that three streak freezes was actually no better than two streak freezes. And there were two competing things here, and I think this is important if you're going to build a streak to figure out what your flexibility mechanic is. **Jackson Shuttleworth** (00:48:03): We were getting more users to return after longer times away to an intact streak. But if you start taking three days off from any habit, it's just going to be less likely that you return even four days later. And so, we had these competing things where more users might be returning to a streak, but a lot of users were also just not coming back, we were training them to take more time off. So, that flexibility, what's the right amount of... We've again, this is another area we've run hundreds of experiments on, what is the right amount of flexibility? And we are constantly surprised here. I still don't have the answer for at every point in your streak journey how much flexibility you need. One thing that I can say with certainty though is, give more flexibility when a user is starting their streak. Again, one of our biggest streak freeze experiment wins... I feel like I'm constantly saying this, one of our biggest wins, but they all were really, really big. **Jackson Shuttleworth** (00:48:59): One of our biggest streak freeze wins was when you start a new streak, we give you two streak freezes. And again, it's so funny to think back, it's like how are we not doing this to begin with? But at the time, the streak freeze was an overly gamified mechanic, you had to buy them with gems, that's our in-app currency, because we wanted the whole idea of this to feel like it was really something you earned, that there was a little bit of pain to getting that streak freeze. And so, we tested though, what if we just give users when they start off their streak two streak freezes, and holy smokes to that win. **Jackson Shuttleworth** (00:49:33): And it's sort of obvious now, in retrospect, but if you have a one or a two or a three-day streak, it's really easy just to let it die and restart, again, you need to get to seven days, what we've seen in the data, for it to really lock in. And so, giving users more flexibility so that it's harder to lose their streak initially, and then conversely, and this is what we keep learning, eventually, once people get on long streaks, you don't want to give them as much flexibility. Because there's a lot of times where, yeah, users don't... And I'm like this, I've got a 400-day streak. Note that that is a lot less time than I've been at Duolingo, I have lost and restarted streaks a lot of times at my time at Duolingo. **Jackson Shuttleworth** (00:50:14): But you start getting on long streaks, and you really care about this feature, you really care about your streak. And most people, as long as you're not backpacking through, I don't know, the back country of Utah, you'll be in a place where you can get service. And so, figuring out who is the user that actually could use Duolingo, and not conditioning them to start taking days off that they didn't otherwise need to do is important to figure out where that line is for your feature. **Lenny Rachitsky** (00:50:46): This is fascinating. You can also buy a streak, right? With money. That's a feature, right? **Jackson Shuttleworth** (00:50:51): Yeah. And it's funny, this is also something that we [inaudible 00:50:54]- **Lenny Rachitsky** (00:50:53): You can buy a freeze, sorry, not a streak. **Jackson Shuttleworth** (00:50:56): Yeah. So, you can buy a streak freeze, and the way it works is you can buy gems, and then you can use those gems to buy a streak... And this is something we wrestle with. We're actively working on an experiment, right now that's having a small hit to revenue, but it's a really nice win for retention, and I think it's actually worth thinking about from day one, as you're building a streak, do you see this more as a monetization feature, or do you see this more as a retention feature? What's the role of monetization in this? What's the role of retention? And I think for us it started out much more organically, and so we have a lot of monetization hooks, that again, is the retention PM, I would love to get rid of. But again, it's sort of part of how the streak works right now. And so, we always have this tension of, hey, if we start to make it harder to buy streak freezes, then fewer people buy them, buy gems to buy them, and so there's this more convoluted series of impacts that happen. **Lenny Rachitsky** (00:51:49): Yeah, no, I love that people wanting to buy streak freeze is like the ultimate sign of how much streaks matter. **Jackson Shuttleworth** (00:51:57): Yeah, streak freeze is the other big one that we've recently demonetized, or introduced a free option for, is getting back a lost streak. So, used to lose a streak, we had a feature, in the day, back in the day, called Streak Repair, we'd give you your streak back, you had to pay gems. But what we found that worked way better was a feature called Earn Back, and this is basically where you would have to do a certain number of lessons, as long as you came back within a window soon after losing your streak, do a few lessons and we just give you your streak back. And that was such a retention winner. And again, what we thought about was it feels like you've earned it so much more when you've done... You deserve to have your streak back, we haven't cheapen the streak because you've done something. **Jackson Shuttleworth** (00:52:44): And in this sense, this idea of cheapening the streak is something, like from a philosophical... Philosophy of the streak. From a philosophical level, we wrestle with all the time, of, cool, we're giving out more streak freezes, at what point do we cross the line and users start to realize their streak means nothing? Now, everything that we've seen, users are totally cool with using streak freezes and still thinking about their streak is this meaningful thing, but my co-lead, Antonia, who made that awesome cross-stitch for me, she is the keeper for us of the sanctity of the streak. And a lot of times as we... And I think this is really important to have, as you're thinking about building your streak. You can almost always get engagement wins, up to a certain point, by just cheapening the streak, making it easier to extend, letting users have more flexibility, but you kind of got to hold the line at some point. **Jackson Shuttleworth** (00:53:30): And it's not clear where that line is. And once you... You talk about one-way doors or two-way doors, there's a point where you go too far and it's a one-way door, and all of a sudden those users, those 9 million users on one-year streaks don't care about their streak anymore. And that is, I don't know, again, retention PM perspective, that'd be an extinction level event for us. I don't want all of these users to stop caring about their streak. And so, to have somebody who is invested in the sanctity of this streak, and for us it's Antonia and Luis, he's very good about this, is really important, just so you make sure you don't go too far. **Lenny Rachitsky** (00:54:06): That's an awesome insight. So, to protect... And push notifications I think are another example of this in general for companies, how much is too much? Because everyone is just like, let's just send another push, it's fine, just one more. And so, your solution to that is a person is like the keeper, and almost the gatekeeper, plus the founder, of how far is too far. **Jackson Shuttleworth** (00:54:26): It's good if you can have that. I think push notifications are also easier because there's a lot of things you can do around, all right, we'll send a budget cap for how many notifications we'll send, you can- **Lenny Rachitsky** (00:54:36): It's like [inaudible 00:54:38] policy. **Jackson Shuttleworth** (00:54:38): Yeah, policies. But I think with a lot of things, at least for the streak, it's harder to create policies for in the same way, a lot of it has to be done based on feel, and so you just got to use your best judgment at times. **Lenny Rachitsky** (00:54:49): Sweet. Okay. Any other, maybe one or two more lessons from this journey of what streaks has become today. **Jackson Shuttleworth** (00:54:56): You mentioned notifications, and I've mentioned this a few times. One... It's funny, you tend to think of, exactly as you say, you can just always send another notification, it's going to be some win, and at some point it'll be a bad experience, but it's tough to see that. There's actually a notification that we... So, we send two notifications related to your core streak each day, the first is a practice reminder, we send it, this is actually an interesting insight, 23 and a half hours after you practice the day before. Whoa, that is a lot. **Lenny Rachitsky** (00:55:21): 23 and a half. Okay, **Jackson Shuttleworth** (00:55:23): So, basically, if you practice at noon today, we'll send it to you at 11:30 AM tomorrow, and we have done- **Lenny Rachitsky** (00:55:31): And it's, because it's like assuming they are free in that time the day before, maybe they'll be free at the same time? **Jackson Shuttleworth** (00:55:36): And we actually moved, we used to let users set this practice reminder time, and our thinking was, cool, you're going to say 7:00 PM, that's when I really want to extend my streak each day, and then you know what? I say this to somebody with two kids, life gets in the way, life always gets in the way, and when you think you're going to practice will change, your life will change, whatever. And what we realize is the best indicator of when you should practice was when did you practice the day before. We could almost certainly get more detailed, we have tried a bunch of ways to have much more complex logic, and what always wins is 23 and a half hours. **Lenny Rachitsky** (00:56:07): That's so interesting. Revealed behavior versus stated. **Jackson Shuttleworth** (00:56:10): Yeah, exactly. So, again, we send this practice reminder 23 and a half hours later, the other thing that we'll do though is we'll send a, what we call a streak saver, and this is at 10:00 at night, if you have not extended your streak, we'll send you a message saying, hey, it's your last chance, this is it, if you don't extend your streak. And you would think that, that's kind of spammy, that's kind of annoying, to get a notification from an app at 10:00 PM, but what we found is because people care about their streak, their streak is this good thing that they attach positive emotions, that they don't really want to lose, that notification reminding them, hey, come back and... People see this by and large as a positive notification and not a negative notification. Obviously, it serves our purpose as well of getting users to come back and not lose their streaks, but again, I think if you can think about your notification strategy related to what is the feature that it's tied to, how do users perceive that? You can almost certainly, not get away with more, but you can be thoughtful about notification load, and when to send notifications, and again, for us, this late night message, that's also highly impactful, super good, is actually something that could be perceived as spammy, but a lot of our users really do... Somebody who, it's often late at night, and I work here, and I'm like, oh, forgot to do my... I was think about Duolingo all day, here it is, 11:15, and I still haven't done it, that message is really powerful. **Lenny Rachitsky** (00:57:36): Yeah. It has saved me many times, I totally know that message, and I love that it's a late night message from an app, very rarely do you actually, are happy about that, and I love that this actually is a good example where- **Jackson Shuttleworth** (00:57:51): It's really funny, all of the stories that you hear about people extending their streak, if you look around a Duolingo party, where it's like 11:30, 11:45, all the Duolingo employees, they're are doing their lesson at the last minute. You always see these pictures of people in the club doing, or at a concert doing Duolingo, and yeah, because it's like otherwise you're going to use a streak freezer, or God forbid you will lose your streak. **Lenny Rachitsky** (00:58:14): That's so funny. Okay, anything else? And if there's more than one more, definitely share, but any other really interesting lessons or wrong turns or insights? **Jackson Shuttleworth** (00:58:23): I talked about streak freezes, and we've done a lot with streak freeze, but I think if you're going to make flexibility a thing, it's probably also useful thinking about how do you celebrate perfection. And so, we have a feature that we have, it is the simplest thing in the world, it's called Perfect Streak. And it's just, if you don't use the streak freeze for a few days, we make your streak look gold, and we make your little progress bar on the calendar just look a little bit nicer. There's no reward for doing it, you don't get anything other than this nice little indication, and it is awesome. It is a simple feature, it is ultra not complex, and it is really powerful, not only for getting users to, as a bit of a reward, they'd be hey, get to seven days without using a streak freeze and your streak becomes perfect, but it's also a really nice indication of users who aren't using streak freezes. **Jackson Shuttleworth** (00:59:14): Here is the thing that if you don't use a streak freeze, which, again candidly, I would love for you never to use a streak freeze, if you don't use a streak freeze, your streak will stay perfect. It's funny, we actually just, we're constantly responding to bug reports about the streak. It is... I swear to God, we have the best infrastructure around this feature because it is so important. We had an employee who lost her, I think a four-month perfect streak, and it was a big deal for her because she did her lesson, and she was crossing international dateline, there was a bunch of stuff going on that was like, it was just kind of weird in our backend. But people start to care about perfection as much as they do their streak, and for that person it was a big deal when they lost their perfect streak. And so, this is just an example of, look, if you're going to go after flexibility, which is good, finding a way to pull users back into perfection is a really important counterweight to have. **Lenny Rachitsky** (01:00:13): What I'm imagining is you guys need a Amazon style chatbot that just gives you the streak back, it's just like, okay, here you go. **Jackson Shuttleworth** (01:00:20): We have very much... So, we have, if people lose their streak, there's ways to get in contact with us, but we've actually thought about that, where it's like, okay, we should just build a self-service feature, and if we think that your excuse is good enough, whatever, we'll just [inaudible 01:00:34]. **Lenny Rachitsky** (01:00:34): Yeah, yeah. [inaudible 01:00:35]. **Jackson Shuttleworth** (01:00:36): Because again, I'd much rather you be on a streak than have lost it, particularly [inaudible 01:00:41]. **Lenny Rachitsky** (01:00:41): Right. But it also can feel that easy. I love this, I also love this point about just the power of the animation and user experience having impact, that's really interesting. Is that something you find often, just celebrating and making it feel really amazing without copy or any feature is just like, holy, you're awesome? **Jackson Shuttleworth** (01:01:02): This is another thing where it's like when users care about the feature, using not only animation, haptics, sound effects, using... And it's funny, we don't have sound effects on the streak, this is probably something we'll look at in the not too distant in future, but haptics are something we have done a lot of testing on- **Lenny Rachitsky** (01:01:18): Like the phone vibrating in various ways. **Jackson Shuttleworth** (01:01:20): Yeah, exactly, your phone, there being a really cool haptic pattern as you extend your streak, all of this stuff wins. And it's cool because I think it wins... There's a few reasons. One is it just makes you feel good, you get some cool moment in your streak, and we celebrate you, and we celebrate you in this visual way, and your phone's buzzing, it just feels awesome. The other thing it does is it causes you to pause on that screen, and I think there's this desire, as you think through a lot of, as PMs think through, oh, how can I get users through this funnel as painlessly as possible? I talked about [inaudible 01:01:52]. There's a lot of times where I don't, I want you to stop. I want you to stop and land on the screen. **Jackson Shuttleworth** (01:01:56): You got to be careful not to do this for too many screens, but the one big ones, sometimes I just want you to pause there and enjoy the moment. If I can get you to enjoy the moment more, you're going to care more about your streak, and you're going to be coming back tomorrow. And so, animations that are cool, and that cause you to really soak it in, haptics that feel good, all of that comes together to make you really focus on that moment, all of that just gets users more connected to their streak. So, animation in the right times works well and it's something we've had win quite a lot. **Lenny Rachitsky** (01:02:29): Who designs the haptic stuff? Is there a haptic designer? **Jackson Shuttleworth** (01:02:33): For the longest time it would be a product designer, or actually, it initially started as the engineer would be like, all right, would cobble together haptics, based on what they felt good, then it became a product design role, where they would use their best judgment. We actually just recently required an animation studio, Hobbs in Detroit, and now they are the sort of keepers of, they do a lot of motion design work, haptics very close to that, and so they do a lot of that. I do remember trying to hire for a while a haptics contractor, like haptics design, and it was the saddest hiring I've ever done, because it was just, I don't know, it was such a specific... I don't know. I just went through a lot of people who, it's just a really tricky space of kind of sound effects, kind of motion design, sort of technical... **Lenny Rachitsky** (01:03:22): Yeah, such a unique role. **Jackson Shuttleworth** (01:03:25): Very unique specific skill set. **Lenny Rachitsky** (01:03:27): Right. And there's very few apps that really need this this deeply, so you're almost creating this person. **Jackson Shuttleworth** (01:03:32): Yeah. **Lenny Rachitsky** (01:03:33): That is fascinating. That's like a whole podcast on its own. By the way, I was going to say as you're talking about this, I love that it's a win to celebrate people that don't lose their streak, you introduce this way to make it flexible, and that's a big win, and then you go the opposite direction of, if you don't use this feature, you also feel even better. **Jackson Shuttleworth** (01:03:51): Well, and it's funny, you talked about the danger of feature bloat, or we sort of talked about the danger of feature bloat, this is actually something I'm constantly thinking about with this. We have the streak, but then we also have the perfect streak, and we count how many weeks you've had a perfect streak. Well, all of a sudden we have two streak numbers that are competing with each other. It's funny, we actually don't introduce the concept of a perfect streak until after you've hit seven days, and some of this is just because the cognitive load of additional streak features. A lot of our cooler streak features, you got to get on a long enough streak. And not to say we haven't tested it because we have, because we test everything, introducing these features earlier, but what we've found is that pretty universally they lose when we introduce too many things, too many concepts to users too early in the experience, it's just hard for them to manage. **Lenny Rachitsky** (01:04:39): Okay, sweet. I know that we can go down this track for hours and hours, there's endless learnings about all the things you all have done along the journey. I want to shift to talking about how your team operates. So, there's a lot of threads you touched on of just how a team can do this so well, shift 600 experiments, as you said, continue to find opportunity. What are some maybe lessons or advice you'd have for folks that are like, oh wow, I want to work more like this, from your team's experience, how does your team to operate that folks can learn from? **Jackson Shuttleworth** (01:05:13): Yeah, maybe just a little bit of context. Duolingo cares a lot about... So, most of our teams are metric-based teams. So, we do the most work with streak, but the metric, what we really care about at the end of the day is CURR, and DAUs, because we see that DAUs hit CURR. And so, when you can be really laser focused on, my goal each quarter is to make this metric go up, I think it's much easier to make sure that you're working on the highest ROI thing. I think when you think more about like, oh, I want to make this feature better, I think it's easier to get lost in what better means, and how you think about better. And so, I do think that having a really strong degree of focus as a team on what is the metric that I'm caring about, and how is that directing my efforts is- **Lenny Rachitsky** (01:05:59): Versus feature-oriented. So, basically your teams are structured around a metric/a goal/outcome versus we own this feature, or this product. **Jackson Shuttleworth** (01:06:07): So, retention owns streak, I guess, but that's only because we've seen streak drive CURR better than any feature. But we are not, we have this IAP hook with our streak freeze purchases, there are other teams that work on, that can and have worked on the streak, because it's not ours to say, no, no, no, we do all the iterations here, we just know that it drives our metric better. In the same way that leaderboards, we have a team that focuses on how much time you spent, we want users to spend more time on Duolingo so they're learning more. Leaderboards is the best vector for doing it, so that team does a lot of leaderboards work, but every now and then I have an idea that I think will be highly retentive, and I will go in, and I'll pitch to them, and then we'll do some change to the leaderboard to make it more retentive. **Jackson Shuttleworth** (01:06:53): But I do think having that clear metric of we're trying to drive CURR not we're trying to just make this feature better, helps at least make sure, give the team clear marching orders, and that focus I think is really good for prioritizing backlog. **Lenny Rachitsky** (01:07:07): Cool. This is a really important point, this is the same way Airbnb worked, when I worked there for a long time, is it's, here's a goal that we want your team to be responsible for, you can work on any product you need to hit this goal, as you said, often various products are most connected to what you're doing, but what you're describing is, even though a team's kind of... I imagine you own it from a [inaudible 01:07:29] perspective, and you're like are the shepherd of this part of the feature because it hits your goal, helps your goal most. But any other team can come in and be like, hey Jackson, we need to work on some streak stuff to help with learning, you're like, go for it. Just a tangent there. Do they work really closely with your team if they want to do some work in the code? How does that work logistically? **Jackson Shuttleworth** (01:07:49): Yeah. If you are, again, this is where I say there's soft ownership, we're not against teams doing things to the streak, but if we're going to do something given we probably have multiple quarters worth of a roadmap around the streak... I say probably, we do. Multiple quarters of roadmap for what we can do to the streak, if other teams want to come and mess with it, okay, we got to just figure out how is that going to work with what our plans for the streak were, how do we make sure a lot of times when teams are coming in thinking, hey, let's do this to the streak, they're in context that we might have, and so there's as much of a much simpler version of what we're doing now, a bit of a knowledge sharing, of saying, all right, well, this is what we think about the streak, this is what we've seen work, hasn't worked, how does that influence some of the hypothesis that you have. And so, I think getting that really... Making sure the juice is worth the squeeze. **Lenny Rachitsky** (01:08:32): Good old-fashioned product management work right there. **Jackson Shuttleworth** (01:08:34): Yeah. **Lenny Rachitsky** (01:08:35): Cool. What else is interesting about how you all operate and how you all work to achieve this sort of success? **Jackson Shuttleworth** (01:08:41): Again, my team lead runs, Antonia runs the most... A really process, if you're going to run this experiments, you have to be really process-oriented and really thoughtful about which experiments am I going to run when, how is that going to set up the next one, there's heavy Jira automation, I think sometimes the Atlassian suite makes my eyes bleed, but there's a lot of times where that degree of process helps the team unblock engineers and make them move really fast. And so, making sure that you have really good process around how are you going to run so many experiments, it's worth investing in. **Lenny Rachitsky** (01:09:17): Can you follow that thread actually? Just when you say that, what does that look like? What are some elements of that process to make this work efficiently? **Jackson Shuttleworth** (01:09:25): All the way down to, really detailed roadmaps around, all right, we're running this experiment is based on the results of this experiment, or might hook into an element of this feature, how do we make sure that we're lining up implementation on this so that as soon as this thing runs and we're ready to go, we can start rolling out the next one. I hate features just sitting around and us not, again, continuing that thread. So, it's not just thinking about what's our engineering bandwidth, but also what's the design bandwidth to make sure that we have the next iteration of this feature ready to go. We're planning months out, as we think about these feature iterations, even small ones, feature iterations, because when you lose cycles, not pushing on a feature, it's just sort of lost opportunity. And so, everything from being thoughtful about engineering roadmaps to design roadmaps to product roadmaps, all of that needs to come together in a system. **Lenny Rachitsky** (01:10:19): So, essentially, mapping dependencies across function, and you're saying in Jira you can do this. **Jackson Shuttleworth** (01:10:25): You can do a lot of it in Jira, there is a non-zero amount of Google Docs that we have, that sometimes does things a little bit... I don't know, sometimes it just looks a little bit nicer, it's a little more flexible. **Lenny Rachitsky** (01:10:36): Yeah. [inaudible 01:10:38]. **Jackson Shuttleworth** (01:10:37): But Jira is our, it is where the motherload of process is. **Lenny Rachitsky** (01:10:42): Great. Okay. What else? **Jackson Shuttleworth** (01:10:44): Another thing that I'll just say is, we really resist the urge to do the big V1. And I think this is, I shared the streak goal example, where, a lot of times when we're exploring something we will say, okay, well, that's cool, how do we strip away a bunch of stuff and figure out what our core hypothesis is? And then, just ship that thing first as a V1. Because it's easy, and I've found this time and time again, it's easy to add things, features that make them win, I've worked in retention engagement long enough, I can add, I know enough things to pull, and bells to add, and whistles to make something win, but there's a lot of times where it's like cool, t [inaudible 01:11:27] because all the whistles you added, not because of what your core hypothesis was, and a lot of times if you can just really simplify what the feature is, it's also much easier to ship, it's easier to design. **Jackson Shuttleworth** (01:11:37): You're not designing for a whole system, you're designing for something much simpler. And so, getting everybody to think that way, allows us to end up shipping faster, shipping simpler, designing faster, getting faster approval, getting insight, and then doing what I talked about with streak goal, being able to run iteration after iteration after iteration, add these things iteratively. And then not only by doing this are you able to move faster, but you get confidence at each step of the way, that, hey, my series of hypotheses is actually born out. Or if it's not, cool, then we're going to drop that part of the feature, and then just ship what actually matters. **Lenny Rachitsky** (01:12:18): If I can try to summarize the broad lesson so far that I'm hearing, and maybe you would've shared this, but I'm just thinking, if I were to try to design a company to operate, that we all operate, you essentially map all the levers that drive the business. So, you have this mapping of all the metrics that drive up to growth and daily active users. CURR ended up being the biggest specific metric to drive growth long term, so there's imagining a tree of all the opportunities you could work on, you found this is what is most connected to our growth. You basically just start mining, I don't know if mining is the right metaphor, but just looking for things that move that specific metric. **Lenny Rachitsky** (01:13:04): You just look and poke and explore, and then once you find one, you just go real deep on trying a lot of different... You come up with a hypothesis, and a strategy of here's how we think we can do this, and how we can move this, and then you just try a bunch of stuff. There's also this element of the Arrested Development quote, "There's always money in the banana stand," comes to mind, where it's just keep working on, see there's more, there's going to be more opportunity at this. **Jackson Shuttleworth** (01:13:29): When I joined Duolingo, the PM that I took over for, Anton, who used to lead the retention team, I remember saying, "Dude, the streak, it just counts up, you guys have been testing on it for years, how much more work can we do on the streak?" And he was like, Jackson, you child... He didn't say exactly this, but this is how I felt it. Like, Jackson, you child, we're not even 30% of the way optimized. And four years later, I say that with such conviction, we are so far away from... We've made a ton of strides, but we are still so far away, and every quarter where we ship a ton of wins and improvements to the streak, it just continues to prove to me that there is so much more to be done. **Jackson Shuttleworth** (01:14:11): So, I think your framing of it is... And I would say there's a lot of thought that goes into, again, I talk about the strength of the hypothesis that you have to have as you start to build out larger feature strategy, I do think it's really important to not just do a bunch of random stuff but do it with intent, with a goal in mind, otherwise, you do end up in these local maximas. But yeah, there's still a bunch of stuff that we haven't tried that I think we have high confidence in working out and so we'll keep doing that. **Lenny Rachitsky** (01:14:45): Are there any other, say, lasting lessons from this journey that if someone were to try to operate this way, build streaks into their product, anything you'd recommend? **Jackson Shuttleworth** (01:14:55): Yeah, I really do think it starts with... Streaks are an engagement hack. You can make your app more retentive, I'm almost positive, almost every app out there can make it more retentive. It is loss aversion, that is, again, armchair psychologist Jackson, it's just a thing that works on humans. But if your app is not something that users want to use every day, or whatever cadence you want your app to be, to work on, it's going to be, you're only going to get so much from that streak, and honestly, it's probably going to distract you from what really should matter, which is making your app something that people want to use every day. **Jackson Shuttleworth** (01:15:35): And so, if you start focusing on the streak but you haven't made that an enjoyable experience, you're just going to waste a lot of time, honestly. And so, I think making sure that you have your core loop of your app figured out, that it is giving value to users, it is something that they want to come back to every day, that really sets the stage for something to layer a streak on. So, resist the temptation, if you don't think you've reached that point, to go too hard down the path of streak. **Lenny Rachitsky** (01:16:03): That's a really good point. Just like a streak is not going to solve your problems if people don't actually care about the core value you're providing. **Jackson Shuttleworth** (01:16:09): No, and honestly, it'll probably cause more problems if what you end up focusing on is how do I make the streak highly engaging, but your app is... You're wasting time that could otherwise be better spent on solving more critical problems. So, that's one learning, the other thing that I'll say is, we met with one of our board members, Bing, Bing Gordon, a few weeks, or a few months ago rather, and he had this comment where he was just like, "The reason why users care about your streak so much is because you care about your streaks much." You being Duolingo. The reason why users care about our streak so much is because Duolingo cares about the streaks so much. And we're like, what do you mean? Well, he's like, well, after every session you see a big streak screen, and it's animated cooler than almost any other screen in the app, and then sometimes you see some other screens, and there's all these other... You don't let a user forget it, you talk about them in messages. And so, I think it's worth thinking about, look, if you're going to build a streak, and then you're going to [inaudible 01:17:06] it off into the corner of your app, where users aren't going to see it, they're probably not going to care about it as much, which might be fine, because there might be other levers that you think are more important to pull on, but there's a reason why we focus as much on the streak as we do, and that's because we want it to be top of mind for users. And that's not by accident then that users start to care about it. And so, I think just as you're thinking about building the streak, making sure that you're giving it the visibility it deserves, if you want it to have the kind of impact that Duolingo has, it's sort of an important hierarchy principle to think about as you design things. **Lenny Rachitsky** (01:17:42): That's such a good point. You look for cues to the app of tell me what I should pay attention to, what's important? If you're just like fire, explosions, you made a streak, oh, maybe I should pay attention to this feature. And then the push notifications obviously encourage you there too. Anything else along those lines? **Jackson Shuttleworth** (01:17:58): Maybe final thing is, look, we ran so many tests on our Duolingo streak to figure out what worked. We have a philosophy at Duolingo, of test it first. We are a lot of times willing to test things. I really think that if you're going to try to introduce a streak, or you want to improve on the streak you have, don't get too caught up in the philosophy of everything, make sure your hypotheses feel like they're good, but my recommendation is just try things. And this is, again, you said it earlier, it's like this is as much human psychology as anything, and as soon as that becomes the case, you kind of just got to understand what users respond to. And the easiest way to do that is to stop spending time batting around ideas in a conference room and just try some stuff. So, huge recommendation to if you're going to invest in a streak, try and figure out what works through testing with users rather than trying to get it perfect on the first try. **Lenny Rachitsky** (01:18:57): Say someone's listening and they're like, should we do streak, is this worth doing? What's your take on just the chances that a streak feature would be helpful to another consumer? **Jackson Shuttleworth** (01:19:07): I am well known for saying in the company that I think every team, every app could benefit from a streak. Now, how you implement it is very different, and I think you got to, what is your user's use case? If they're going to come use, I don't know, tax software... Okay, you know what? Now that I say this, tax software would be a hard one, but maybe it's all about you need users to come back every day, during the tax season, or how many times... I don't know. Now, that I say this out loud- **Lenny Rachitsky** (01:19:35): Times you upload your [inaudible 01:19:37] forms. **Jackson Shuttleworth** (01:19:37): Yeah, that is a hard use case. But the vast majority of companies I think have a good idea of like, all right, here is my ideal use case, I want users to come here three times a month, that would be ideal. Or four times a month. You can build a streak to work. Peloton has weekly streaks because the idea of doing a Peloton workout every single day was hard for this user during COVID. It was just like every now and then you get on the Peloton, that was great, but the idea of a weekly streak was something that I could keep up. And so, I think figure out what your usage pattern is, as a user, and then build your streak around it. But as long as you're not a really, again, the tax example is probably a good counterfactual, but as long as you have some degree of frequency in your use, I think almost anything can have a streak. **Lenny Rachitsky** (01:20:29): So, Duolingo, it's, again, a $14 billion company, this feature, possibly the most contributing factor, other than the core product, to that level of success in market cap, and it's hard to imagine another just feature of a product that has had this much impact on growth and revenue and building this sort of business. So, I love that we spent this much time on it, the motherload, the motherload of advice and insights. So, thank you again for putting- **Jackson Shuttleworth** (01:20:59): Of course. Very fun. **Lenny Rachitsky** (01:21:00): With that, we've reached our very exciting lightning round. Are you ready? **Jackson Shuttleworth** (01:21:05): I'm ready. **Lenny Rachitsky** (01:21:06): First question, what are two or three books you've recommended most to other people? **Jackson Shuttleworth** (01:21:10): All right, I'll start with A Guide to Midwest Conversation. So, I'm based in Kansas City, I'm a proud Midwesterner, and us Midwesterners talk in a certain way. I think you hear about Minnesota nice, but we tend not to say what we mean, and it is a very funny primer into what Midwesterners actually mean when they say what they say. So, highly recommend reading that. **Lenny Rachitsky** (01:21:33): I like that you give that to people, just like, here's what I might be telling you, which you may not read. **Jackson Shuttleworth** (01:21:38): My wife is German, and I gave it to her so she could better understand. **Lenny Rachitsky** (01:21:40): I see German being the opposite of that, okay. **Jackson Shuttleworth** (01:21:44): Very different. Another book, this is a good one, Fate is the Hunter. This is a really cool book, it's a memoir of one of the early commercial airline pilots, and it is wild to hear the stories about what flying was back in the day. I'm a former management consultant, I flew every week for almost six years, and I never once had to worry about, am I going to make it to the other end of this flight alive? That was not the case back then, and so some of the stories about what it used to be like to be a pilot on some of these planes, before modern aviation technology, is fascinating, and makes you really appreciate what we have. **Lenny Rachitsky** (01:22:20): It feels good to read a book like that, being a software PM or engineer or whatever, how different that life is. **Jackson Shuttleworth** (01:22:28): Hardware is hard. **Lenny Rachitsky** (01:22:28): Hardware. Oh man, it's not haptic design. Okay. Next, unless there's any other books you're going to share? No, okay, great. What's a favorite recent movie or TV show you've really enjoyed? **Jackson Shuttleworth** (01:22:40): So, I have two kids, I watch a lot of Bluey, it's really good, I swear, it brings me no shortage of joy. But adult show or show not meant for four-year-olds that I have watched, I just finished the latest season of Emily in Paris, man, wonderful. I realize it's not the highest brow of television, but just beautiful people in beautiful cities, solving problems that are not earth-shattering, sometimes it is nice to just tune out. Also, I'm learning French on Duolingo, slight plug for the app, I can understand a lot of the French that is being spoken, and there is no better joy than having invested as much time as I have in French, and actually being able to use it. So, huge fan of Emily. **Lenny Rachitsky** (01:23:21): That is so funny, what a fun Venn diagram of interests. My mother-in loves Emily in Paris, I saw someone tweeting about what Visa is she on? How is she still in Paris? **Jackson Shuttleworth** (01:23:33): Yeah. You best just not ask questions, there's a lot of questions for this show that are better left unasked. **Lenny Rachitsky** (01:23:40): [inaudible 01:23:40] Okay. Do you have a favorite product you recently discovered that you really like? Other than Duolingo. **Jackson Shuttleworth** (01:23:44): Last week I went to Home Depot, and I bought a new ladder, and ladder innovations, you don't think of often, but you can make one of the legs go a little bit further than the other leg. And as somebody like myself who has a house that is built on a slight slope, every time I go up on my ladder, I take my life in my hands, but with this ladder, I'm always even. I cleaned my gutters twice last week just because of how awesome this ladder has... How much this ladder has changed my life. So, ladder innovation, I don't think it gets talked enough about and so I'm happy to give it the spotlight it deserves. **Lenny Rachitsky** (01:24:18): I appreciate you doing that, and it's the first ladder recommendation we've had on the podcast. Two more questions. Do you have a favorite life motto that you really find useful in work or in life they share with folks? **Jackson Shuttleworth** (01:24:26): This probably will not be much of a surprise based on how I've talked about our willingness to test things, but you miss 100% of the shots that you don't take. I'm a big fan of just trying things, even if your possibility of success is not 100, because you learn a lot along the way. **Lenny Rachitsky** (01:24:44): Final question, do you have any fun traditions at Duolingo, amongst either the PM team or the company in general that might be delightful to share? **Jackson Shuttleworth** (01:24:53): We have way too many traditions to count. I will share the weird tradition that we do at every retention standup, and this started during the pandemic, we obviously used to stand up in person, and then when we went remote, we did this thing where whoever's the last person to go would count down 3, 2, 1, and then we'd all try to clap at the same time, which was kind of fun and dorky, but we fell in love with it, and four years later we're still doing it. Recently we've added, we all say yee-haw in unison afterwards, I can't tell you why. But trying to synchronize a clap via Zoom, and then all shouting yee-haw... I did this in a phone booth the other day and after I came out someone told me, "You know that those aren't as soundproof as you think," but when you get a good opportunity to give a yee-haw, you can't pass up on it, so. **Lenny Rachitsky** (01:25:47): I love these little things, they sound so minor, but they're such important elements of team culture and tradition, and so important for PMs to find ways to just have fun and do something ridiculous. **Jackson Shuttleworth** (01:25:58): I will say, it took a while to get people behind shouting yee-haw, but now that we have people doing it, you can't take it away [inaudible 01:26:08], we all love it. **Lenny Rachitsky** (01:26:09): Oh man, I called our all hands for a while, y'all hands, feel free to steal that. **Jackson Shuttleworth** (01:26:14): You get it, you get it Lenny. Yeah. **Lenny Rachitsky** (01:26:17): I get it. Jackson, this is incredible, I feel like people are going to listen to this with notebooks, and just like, okay, here's a bunch of ideas we should try with whatever we're working on, whether it's streaks or not. Thank you so much for being here. Two final questions, where can folks find you online if they want to reach out, learn more, learn more about Duolingo? I know you're hiring product managers, so share more there, and finally, how can listeners be useful to you? **Jackson Shuttleworth** (01:26:37): Yes, you can find me on LinkedIn, that is where most of my online social media is, so Jackson Shuttleworth, and then how people can be useful to me, yes, as you said, we are hiring. We're actually hiring for my team. Are you interested in thinking about streaks as much as we do? We might be the right home for you, so please, you can apply on our website. We're also hiring from a number of other product management roles, and they're all as thrilling as this work is. **Jackson Shuttleworth** (01:27:05): And then, I'm always interested about how other companies have implemented streaks and what they've learned, and so what I'd say is if you're a company who's implemented a streak maybe in a different way than Duolingo has, or you found a whole ton of success and another vector, another element of the feature that we didn't talk about today, I would love to know more. I used to catalog basically every streak I found out there, and as it's become more of a popular feature, it's just been hard to keep up on. So, if you have interesting streak insights to send my way, I would love to hear them. **Lenny Rachitsky** (01:27:41): I love that, a collection of all the best ways of doing streaks. Jackson, just I want to say congrats to your team and you for having so much impact. This is like the dream of a lot of PMs and teams, is to see this much impact and continue to ship wins, and so congrats, nice work. **Jackson Shuttleworth** (01:27:57): Thank you very much. **Lenny Rachitsky** (01:27:58): Thanks for [inaudible 01:27:59]. And with that, Jackson, thanks so much for being here. **Jackson Shuttleworth** (01:28:02): Yeah, thank you Lenny, this was a lot of fun. **Lenny Rachitsky** (01:28:04): Same. Bye everyone. **Lenny Rachitsky** (01:28:07): Thank you so much for listening, if you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny'sPodcasts.com. See you in the next episode. --- ## [15/17] How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng) **Farhan Thawar** (00:00:00): If you do the hard path and it doesn't work, actually you still win because you've now done something hard. You've probably worked with smart people. You've learned something along the way that is valuable. I meet lots of job seekers. I go, what are you doing to try to find a job? Are you really learning anything from sending out 10 resumes a day? Why don't you look at the API Docs and build something? Even if you don't get a job at Shopify, you've learned something. **Lenny Rachitsky** (00:00:20): First, I want to talk about another theme, creating intensity in your organization. **Farhan Thawar** (00:00:24): Everyone says, "Oh yeah, work hard and do more hours when you're young, whatever." I'm like, "What if you just did more per minute?" **Lenny Rachitsky** (00:00:29): The more I dig into the Shopify way working, the more fun stuff I never expected emerges. There's been a drive to delete code and simplify. **Farhan Thawar** (00:00:37): We have a Delete Code Club. We can always almost find a million-plus lines of code to delete, which is insane. **Lenny Rachitsky** (00:00:42): I found this great quote from you, "Not everyone can look stupid in public over and over, but I believe it's my superpower." **Farhan Thawar** (00:00:48): I have been in many situations with many sharp people who have said to me, that's the stupidest fucking question I've ever heard. My goal there is not to annoy the person, but it's to understand the content. **Lenny Rachitsky** (00:00:59): I was looking at your LinkedIn and your career history, and I noticed that you've worked for a different billionaire every decade of your life. **Farhan Thawar** (00:01:05): They're mostly different people, but they're similar in one thing is that they haven't... **Lenny Rachitsky** (00:01:12): Today my guest is Farhan Thawar. Farhan is Vice President and Head of Engineering at Shopify. Shopify is an incredibly interesting company because they have over 10,000 employees who are fully remote, and even though they were founded almost 20 years ago, they continue to operate with urgency, velocity and have very first principles, ways of thinking, which translates into them seeing record usage, blowing away their earnings calls just recently, and building a beloved product. A lot of this is thanks to Farhan, who in our conversation shares very specifically what he's done to maintain intensity and urgency within the engineering team. Including their meeting cadences, the counter-intuitive power of pair programming, how they run meetings, how they cancel meetings constantly and so much more. He also shares his experience with indexing towards choosing the harder option when you have multiple options to choose from and why that ends up making your life easier. **Farhan Thawar** (00:02:51): Thanks for having me. **Lenny Rachitsky** (00:02:52): As I was preparing for our conversation, I talked to a bunch of people that you've worked with over the years, and there's basically three themes that kept coming up over and over and over. One is hiring, two is creating intensity in your organization, and three is choosing the hard path. First of all, does that resonate? Second of all, does it sound good to talk about these three themes in our time together? **Farhan Thawar** (00:03:16): Yeah, I mean, I have ideas on where all three of those things came from, and I think that it is something that if you looked back on my career, I've hit points on each of those things, but I don't think at the onset I knew that that's what I was doing, but it turns out in retrospect, that's what I ended up doing. **Lenny Rachitsky** (00:03:32): Perfect, so this is the Steve Jobs. Everything looking backwards it all connects. **Farhan Thawar** (00:03:36): Yes. **Lenny Rachitsky** (00:03:37): **Farhan Thawar** (00:05:42): Okay. **Lenny Rachitsky** (00:05:43): Advice that I've heard you share with people often is when they're trying to decide amongst a bunch of options is to choose the harder path because that makes life easier down the road. Share this advice why it's so important, where you learned, where you developed that this is the right approach. **Farhan Thawar** (00:05:59): But the short version is that if you have a choice and you choose the easy thing and it works great. If you choose the hard thing and it works great, you did more work, but if it doesn't work and you chose the easy thing, you've actually not learned anything because you chose the... You haven't done a lot of work, you haven't probably worked with the smartest people because they're not usually around on the easy path, and what happens is you've gone through this exercise and now you're like, I've kind of lost. I lost the choice, or I was trying to do something, it didn't work out for me. But if you do the hard path and it doesn't work, actually you still win because you've now done something hard. You've probably worked with smart people, you've learned something along the way that is valuable, and I can give you a quick example. **Farhan Thawar** (00:06:41): So I meet lots of job seekers and they're like, I go, "What are you doing to try to find a job?" I'm like, "I'm sending out 10 resumes a day." I'm like, "Okay." That sounds kind of easy, and are you really learning anything from sending out 10 resumes a day? Versus I would say to them, "Hey, you know all these companies you're interested in, Shopify might be one of them. Why don't you look at the API Docs and build something, build a Shopify app, build an admin extension, build something on top of Shopify." Even if you don't get a job at Shopify, which is maybe your goal, you've learned something, you've built something, you have things in your GitHub repo now and you can show people. You're learning about the product that might translate to a job you might get somewhere else. So I think that even though it's harder, right? Of course, you can't every day build an app on a different platform. **Farhan Thawar** (00:07:23): Maybe you can once a day. You will learn something in the hard path. And the same thing happened to me in taking hard courses. I would get worse marks, but I ended up meeting smarter people in those courses because they were there for the same reason I was because the content was hard. And so that's something that I've just realized in my life that if I do the hard thing and I just naturally tend towards doing that, I ended up doing... I went to Waterloo and I did a minor in electrical engineering on top of computer science, and when I did my MBA, I did a minor in financial engineering because the smarter people were in that path and they're still my friends today. **Lenny Rachitsky** (00:07:54): So building on the last point you just made, people could hear this and think, okay, if it's harder, that's going to be the right path. Sometimes harder is still a bad idea. For example, joining a terrible company that's extremely frustrating to work at or building, I don't know, a house in a really dumb way, but it's just really hard. What else do you find is important to think about when you're thinking it's not just harder, but also XYZ should probably be true? **Farhan Thawar** (00:08:20): Yeah, one real one is of course the people, because I find that my path has always focused on trying to pick the best learning journey. Where can I learn the most? And for me, everyone's different. Some people might learn better from books or the domain they're in, but for me, I learn a lot from people, and so I try to put myself in those harder rooms on purpose. There was a time when I was doing my MBA in financial engineering, by the way, and I'm a tech guy and still a tech guy, and all these people were going into finance jobs. **Farhan Thawar** (00:08:46): There was a point where somebody said to me, "Why are you in this class?" Because they knew that I was doing it for fun, and so it was because it was the learning journey. And so I would say a big part of it for me is yes, there's the how do you win even if you lose, because if it goes poorly, you can still come out of it with skills, but if you actually take the hard path, you'll have these intense working relationships with smart people that again will continue on in your life. **Farhan Thawar** (00:09:12): And that also just forces you to be in this constant state of uncomfort by going into these rooms and saying, "I don't know anything," and it's harder. And I agree with you. You don't want to do dumb things like, oh, let's just do this thing in a dumb way. That's not what I mean. I mean, let's try to do the hard thing that we can learn from. And by the way, it happens to be on the path. It's just is it might take more manual work or it might not be the way most people do it, but we think we can learn more from that path. **Lenny Rachitsky** (00:09:37): Speaking of that, I found this great quote from you, "Not everyone can look stupid in public over and over, but I believe it's my superpower and I try to make it my whole team's superpower too." **Farhan Thawar** (00:09:49): Yeah, I mean, it sounds funny, but again, I'm the one who's always trying super dumb things and sometimes they work, and even my wife hates that I try these things even at home, right? I'll just like, what's an example? It might be a new washing machine and I might try some weird mode with some clothes, and I'm like, "Oh, you ruin the clothes." I'm like, okay. But now I know that this mode should not be used, but maybe I would've uncovered that there's some super fast, quick wash that I can do in 20 minutes that now saves us 40 minutes of wash time every single time we use the washing machine. **Farhan Thawar** (00:10:22): So there's things like that, but I will ruin lots of clothes trying to do that, but the same at work. We'll try things and sometimes it can lead to disaster, hopefully not, but you can imagine people trying to like, oh, let me try this new configuration of GCP and maybe we'll get some benefit, but maybe we'll take Shopify down. We don't want to do that. So you want to have some sort of guardrails. But there is something around trying dumb things and saying dumb things. Half the time, by the way, when I say something dumb, people go, "I had the same question." They just were scared to say it. **Lenny Rachitsky** (00:10:55): So for folks that may want to, because I feel like this skill is so hard, but so important, being okay with failing, being okay with looking dumb, is there something you tell people to help them build this other than just like, I'm genetically good at this stuff? What helped you become comfortable with being wrong and failing before you were a big shot exec where it's like, oh, he's fine. He knows what he's doing. **Farhan Thawar** (00:11:17): I don't know. I mean, I kind of grew up working in retail and people come into the store, and then I would say, "Hey," and you're working on commission, and they're not always buying stuff, and if they don't buy it, you don't make any money. And so maybe just the fact of going up and forcing myself to talk to people and then trying to get them to, and maybe you spend an hour with a client and then they don't buy anything, but you're getting that reaction of a bunch of negatives, and all you have to do is say, okay, and just go to the next customer. You can't really well on it and be like, oh my God, my whole day is ruined. But instead, you have to learn from that and say, "Okay, let me try this. Let me try that." And it's not easy, but it was a way to build up some confidence and people say, this telemarketing, or there's a bunch of things you can do to get a lot of rejection. Cold calling is another one, and that can lead you to actually building up resistance. I don't know if I'm genetically better at it or not. I just think that I literally don't care if I look dumb. I've always said the dumb thing, I'm not doing things on purpose to get nos, which by the way, is part of some sales training, which is go and get 10 nos. But I haven't done that. But I have been in many situations with many sharp people, business people, successful people who have said to me... Turn around and said, "That's the stupidest fucking question I've ever heard." I've definitely had that happen to me. And I'm like, "All right, let's move on to the next question." **Lenny Rachitsky** (00:12:36): I love that attitude and I think that's key to it. It's just bounce off of it and not be crumble and I think it's empowering for folks to hear from someone like you that has done so well that people tell you that is the dumbest question I've ever heard- **Farhan Thawar** (00:12:48): Oh yeah, still. **Lenny Rachitsky** (00:12:48): Still. Okay. **Farhan Thawar** (00:12:50): Yeah. So how about this? That I heard that's the dumbest fucking question. And then recently I heard, I've already explained this to you three times because I kept asking and I didn't understand, and literally I got this message back saying, "I've already explained this to you three times." I'm like, "Okay, I still don't get it." So my goal there is not to annoy the person, but it's to understand the content. And actually, by the way, I say these were messages, I saved them. I literally screenshot it because I'm like, remember this? It doesn't matter. I'm trying to learn. **Lenny Rachitsky** (00:13:20): One more question along these lines. I was looking at your LinkedIn and your career history, and I noticed that you worked for a different billionaire every decade of your life. So there's a guy named Joe Lemond in your twenties and Chamath in your thirties and Toby this decade, maybe yourself next decade, if things go well. Other than what you've shared or maybe it is what you've shared, is there a thread across these three folks that have been really successful that you've learned from that maybe is consistent across them all or even just specific to each one? **Farhan Thawar** (00:13:49): It's interesting because again, this is looking back, you're like, wait a sec, I didn't plan it this way. There's no way you could plan it, right? I'm going to work for a different billionaire every decade. That's not how it works but they're similar. They're mostly different people, but they're similar in one thing is that they have an irrational view of what the world should look like over the next decade or so. They're very long-term thinkers, very rational in that they'll look and say, "Hey, in 10, 15, 20, 25 years, this is what the world's going to look like." And I'm not good at seeing that vision, but I'm good at trying to move towards that vision 1% a week. And so the melding of the two, I know where I'm good and I'm good at pushing the ball forward. And if they're good at the long-term vision, we can both align to say, "You're good at this thing. I'm good at this thing. Why don't we merge forces?" **Farhan Thawar** (00:14:35): And so that is something that has resonated with me is like, how do I find these irrational all progress depends on the unreasonable man. How do I pair with these people because I'm altogether too reasonable and there's no way for me to become unreasonable, and so I have to merge with these people. And so that is again, something that I specifically have sought out. And even when I was starting my own company in 2015, I actually sat down and wrote a list of all the unreasonable people that I knew in Toronto, and I went down the list and met every single one of these entrepreneurs to figure out are we API compatible and could I work with them? And I ended up picking one of them and starting a company. **Lenny Rachitsky** (00:15:15): That is an amazing story. So first of all, I just love this insight that being aware of this is not a superpower of mine and I'm not going to try to build it. I'm going to find someone to merge with, and connect your APIs together and be the person that builds it, not the person that envisions what to build. I think that's awesome because a lot of people... I need to get good at all these things. I need to become the best at vision and strategy and execution and collaboration and then all these things. And so I think alone, this isn't really interesting instead it's just recognize your strengths and weaknesses and double down on your strengths. **Farhan Thawar** (00:15:47): Yeah, it sounds funny, but me and you talked about it that a framework I wrote down, which I tweet out, me writing that down changed how I picked jobs forever, right? Because I had this lull after my first job in between where I was trying to figure out why nothing felt as exciting as my first job. And it turns out that it took me to sit down and be like, what do I actually care about? And people can get confused. I get confused all the time, by the way, by things that are not on my framework. So for example, a good one, title, company, money, all these things can confuse you because you could have somebody say recruiter messages you and says, "Hey, by the way, here's a new job and here's the compensation." You're like, "Oh my God, this is exciting." And if you don't have a written down framework of the things you actually care about, it's very hard to be distracted. So very hard not to be distracted. You get distracted by that. So instead, I look at the framework and go, does this align with my framework? Right? **Farhan Thawar** (00:16:43): Actually to the point of, I actually sent my framework to a recruiter one time and I said, "Hey, this thing," because they kept going back and forth to me and I go, "Hey, this doesn't align with my framework." So it really saves me time from not being distracted, but it also forced me to think about every year I can reevaluate what I'm doing and look at the framework and say, "Is this true to my values?" Now, my wife will say this, that I'm like a robot. When I realize that my framework is being violated, I will resign instantly and I've done that before. So without even having another job or anything, I just go like, oh, my framework is being violated and then resign. There's this thing where I know what I enjoy working on, and that framework helps me find it. And so I encourage everyone, anybody looking for a job I always say, "Write down a framework. You can use mine as inspiration, but figure out what you care about and make sure that what you're working on lines up with that." **Lenny Rachitsky** (00:17:37): And this framework is the questions to ask about where to go work. That's your framework. Okay, cool. We'll link to that so folks can check it out. The example of you resigning when it didn't meet your framework, is that a story you're up for sharing? Is there something to learn from that? **Farhan Thawar** (00:17:50): Yeah, sure. So this happened when I was at my previous, a few companies ago, we were running a mobile company called Xtreme Labs. That was the one that Chamath was the major investor in and so we worked with him directly. And what I realized was... And so that company was amazing. We worked on it for many years. It was a mobile app development company. We got to work on mobile apps for the biggest brands in the world, Facebook, Twitter, Instagram, Vine, the NFL, NBA, Bloomberg, Slack, you name it we worked on those mobile apps, and this is right when the iPhone and Android were really gaining steam in '09 to 2013 era. And then we eventually got acquired by Pivotal. And over time, my role at Pivotal, Pivotal, and Pivotal Labs changed from, hey, I was running the biggest office in the world. I was running the biggest pair programming office. **Farhan Thawar** (00:18:34): I'm a big fan of pair programming to one in which we were really trying to attach consulting to the product. And I ended up being a field CTO, which really, I mean it was fun to learn about that world, but it was different than what I was doing. And so if I looked across my framework, it was violating all the things that I was trying to work. I wasn't working with the smartest people anymore. I was on IC. I wasn't learning as much as I could be learning. And so I wasn't on this and I wasn't having a lot of impact. I was like, oh, wait a sec, this is completely not aligned. And then I just told the team, "Hey, I plan on resigning." And that, by the way, led to great other things because I'm an investor in new companies that have spun out from there and it was a great experience. I'm just saying it at the time, lended me to say, "Hey, you're not actually focused on the right things." **Lenny Rachitsky** (00:19:20): I want to come back to Xtreme Labs. I know there's other stories there that are interesting, but first I want to talk about another theme of things that people often raised when I asked them about you. And this one is intensity, and it's specifically creating intensity in your organization and the value of that, the power of that. I've seen that the way you describe this and I love is how do you expend more kilojoules per hour versus spend more hours on work. So talk about just why intensity, first of all, is so important to an organization. **Farhan Thawar** (00:19:53): Yeah. So I think there's a few things. One, I have this fundamental belief that one hour is one hour. It's the same hour. If you spend an hour or I spend an hour, it's the same time that goes by. And if I just expend more calories in that hour. Let's say we both work nine to five. If I can just get more done in the nine-to-five, we have both... The time has elapsed the same for us, but I just got more done. And that allows me, of course, then I'd be like, "Hey, I'm going to take my kid to soccer and do other stuff." We can still do the same things out of work, but during work, I just want to try to get as much done as possible during the time versus expanding the time and I can give you an example. I used to work at a company where it was like I worked 12 hours a day, but I was playing foosball in the middle of the day. **Farhan Thawar** (00:20:37): And then we'd go for a coffee break and you do these things. And of course, the time expanded to 12 hours versus trying to compress into that eight-hour day. And pair programming is a great example because, so it's such an intense activity. Two people on one machine, you can get so much done when two people are working together, not being distracted by the internet and distractions, and just focus on writing the solution to the problem at hand. And it's so tiring that usually when people switch on to pair programming, they sleep 10 to 12 hours a night the first few nights because it's so intense. You're working so hard. But for me, that intensity actually leads to extraordinary outcomes even if you don't have to put in more hours. I think most people, you probably hear this all the time, everyone says, "Oh yeah, work hard and do more hours when you're young, whatever." **Farhan Thawar** (00:21:26): I'm like, what if you just did more per minute? Like quickly get through things. I think there's another unintuitive fact is that people who are really good can actually output high-quality collateral quickly. So take a person who is good and extremely good, the extremely good person can actually get a lot of output in a short amount of time, and the person who's good might take longer. I think there's a time variance there that people don't think about. So you can not drop the quality too much, but get the time down by 2X, 3X, right? Parkinson's Law of scale instead of, if I give you an hour to do something, a really good person can get a high-quality output in one hour. **Lenny Rachitsky** (00:22:07): I want to talk about how you create an org that operates this way, but specifically, you just mentioned pair programming. I know that's one of your favorite tools. Talk about why this is so powerful when you recommended... I think as an outside observer, it's like two engineers on the same code. Why wouldn't we do things half as fast? Talk about just why you're a big fan of pair programming specifically. **Farhan Thawar** (00:22:30): It is the most underutilized management tool in engineering, bar none. It is just not used as much as it could be. So pair programming, for those who don't know, it's two people on one computer. So two keyboards, two mics, two monitors, but one computer, they work together and if it's remote, they use it. You can use a tool like tuple, which we use, and you can just remotely be on one computer, and you're totally right. The famous tweet about pair programming is, wait a sec, we have two engineers on one computer, won't they write half as much code? And the answer is, oh, no, no, they'll write even less than that because it's not about lines of code. The throughput limiter is not hands-on keyboard. It's not like we're both sitting there and the limiter is like us trying to get through the keystrokes onto the screen. **Farhan Thawar** (00:23:12): The limiter is where is the good elegant solution? How do we think through the problem and build the right solution for the problem at hand? Tobi famously built a lot of Shopify paired programming, and what he would do is he would actually set a timer and him and the CTO Cody would pair program for one hour. And if they did not finish the problem in one hour, they would delete all the code and they would keep the tests and they would start over. And then what their thinking was, if we were not able to articulate and write the code for this feature in one hour, we must be on the wrong design. We must be building the wrong thing and so they delete all the code, kept the tests, and then wrote it again. And sometimes he'd be over by one minute and he would still delete the code and start over because his thinking was the right elegant solution should be able to be written in one hour. **Farhan Thawar** (00:24:03): And so pair programming, I mean, that's an extreme version of it, but even at Pivotal Labs, if your pair was sick that day and you wrote a bunch of code, the strong version is your pair would come in the next day, delete all the code that you wrote, and then you'd write it again the next day. And again, what better time to rewrite code than right after you've written it because you now know the problem domain? And by the way, it sounds like a waste of time. It sounds like I'm just deleting code but the reason is that code lives a long time. Code is a liability and the right solution, the usually shorter lines, more elegant solution tends to appear after you've done a bunch of pathfinding. And the only way to do that pathfinding is start and then delete and then start and be like, oh, no. **Farhan Thawar** (00:24:47): Now I know. Delete. And it's super hard to delete, by the way, because we're humans and we have this sunk cost fallacy, so it's hard to delete. But if you can do that, you will actually land upon a much, much better solution. And of course, pair programming has high, high rates of learning because you're just sitting beside... You're not only whether it's tuple or remote or directly, you learn keystrokes and you learn how somebody thinks about a problem. You go back and forth on the talking, and yes, you will write probably less code, but you will move faster along the path of delivering value for your customers than you would if you did it on your own. And there's all these studies that show happiness is higher, knowledge transfer is higher, less silos, intensity is higher, all the things. And at a price of 20% or something of what you would normally do. **Farhan Thawar** (00:25:33): The analogy I have is the underhanded free throw in basketball, statistically known to sink more baskets, but looks dumb and nobody does it. Literally, Shaquille O'Neal, I'm not that big a basketball fan, but I read this about Shaquille O'Neal, who's a Hall of Famer, and they said, "Why don't you throw underhand?" Because he was notoriously bad at free throws and he goes, "It looks dumb." Even though he's paid millions of dollars a year to do this thing. It looks dumb, doesn't want to do it. **Lenny Rachitsky** (00:25:58): I remember those Shaquille O'Neal years when he had a special free throw coach, and I remember them talking about this- **Lenny Rachitsky** (00:26:00): ... When he hit a special free throw coach. And, I remember them talking about this and he's like, "No, I'm never going to do that." **Farhan Thawar** (00:26:05): "I'm never going to do it." Because it looks dumb. And by the way, go back to the beginning of the interview. I don't care what looks dumb or looking stupid, we're going to do this. And so, actually, I ran the biggest pair programming shop in the world. **Lenny Rachitsky** (00:26:15): On that note, so what percentage of shop Shopify do this? Is this how y'all operate? **Farhan Thawar** (00:26:21): Yeah. So, Shopify, I mentioned that Toby and Cody did this at the beginning of Shopify. And the cool thing about pair programming is, and in my old world at XtremeLabs is that we knew exactly what to build, because we were building mobile apps that were almost like contract manufacturing. We're like, "We have an iOS version. Can we build an Android version?" So, we quickly were able to say, "Here's the spec. Go quick." Shopify is such a different company, right? We are a pathfinding company. We are trying to find the right thing to build. And so, pair programming may or may not make sense all the time. Like Pivotal and Xtreme, we were doing 40 hours a week. **Farhan Thawar** (00:26:54): Shopify is much more of a four to eight hour a week pair programming culture, where you're gathering together on a problem and saying, "Hey, let's pair for half a day, or let's pair every Wednesday." And we use that tool in our arsenal to move quickly down a path. But a lot of other time is spent pathfinding and trying to figure out what to build, and trying to convince field be like, "Hey, we're going to go down this path. Oh, now I know exactly." **Farhan Thawar** (00:27:16): And sometimes, by the way, 18 months later, we've now figured out all the things and that's the time we should delete everything and start over. And, that's something that we will do at that point. And so, you don't want to be pair programming for 18 months. You want to be wayfinding and pathfinding. And then go, "I see the matrix. Let me just delete everything and now build it." Because the learning is what you're going for. We have all the learning, now let's write the code. **Lenny Rachitsky** (00:27:39): Got it. So it's basically, when the code, you're pretty sure this is correct and it's really important segments of the code base pair program. **Farhan Thawar** (00:27:49): Yeah. And then also we do a lot of pairing during an incident or a way to figure out together, work with somebody and say, "Hey, I'm not really sure and let's jump on a call together or jump on a tuple and go down the path." And say, "Let's figure out together what's going on." **Lenny Rachitsky** (00:28:01): I can't help but ask AI, how does that impact this way of working? **Farhan Thawar** (00:28:06): So, AI is super interesting. What's happening right now with an AI copilot like GitHub Copilot is it is your pair programmer. So, you now can feel like you're pairing actually without another human. You can pair with the AI. And so, what's happening too is that you're seeing people use Whisper, like they're talking to Cursor, and they're talking through Whisper to say, "Okay, let's build a new React component that does this." And they're talking and then it's building. "Oh no, that's not what I meant. I meant doing this." So you can actually not even have to type, just using voice, go back and forth with your pair programmer. **Farhan Thawar** (00:28:35): I would say, that's amazing. I would still contend take that experience and add two humans together. So you've got an AI copilot and humans, because what's happening is generating code. And the two humans can look and say, "Oh, I know what it's trying to do." And, either delete the code, because you have inspiration and write it yourself, or just take the suggestion and move it forward. But, I love today's world of AI copilots, because you never have to code loan on your own right? You never have to code alone. You can try a different language now, because the API and the syntax is much easier to pull forward. And so, all of those things are a win for engineering and a win for everybody who wants to build any software. **Lenny Rachitsky** (00:29:14): That makes a lot of sense. Basically, everyone's going to be a pair programmer- **Farhan Thawar** (00:29:17): Yes, exactly. **Lenny Rachitsky** (00:29:18): ... In the future. Okay, I want to come back to what else you have done at Shopify to create intensity. And I think, again, it's important to highlight the intensity is meant to, "How do we get more done in the time we have and then go home?" Not just work all day every day, weekends kind of intensity. **Farhan Thawar** (00:29:35): Yeah. So we have a few things that we have going for us, right? So one, we have this tool called GSD, which stands for get shit done, which you've probably heard from maybe talking to other Shopify folk, which is this notion of weekly updates to the whole company on what's happening. Again, Parkinson's law at scale. If you ask people every week, they want to show progress every single week. So that's one way I talked about pair programming as well. The other thing we do as a company is, we used to have twice a year was our cadence, Black Friday, Cyber Monday, or we had an event in the summer. And now, we do six-week reviews. So, teams have this notion of every six weeks actually coming together and walking through the roadmap, the resourcing, and what they're working on with their immediate leadership, but then also, with Toby. **Farhan Thawar** (00:30:18): And so, what's cool about that, and by the way, it's a huge time investment, right? We all get into a room, it's happening tomorrow. So Tuesday, Wednesday, Thursday, a bunch of us will be in the office together and we're going to go through every project in the company, and we're going to talk about the project, the resourcing, how it's going, and we're going to make changes. And again, that creates intensity, because you want to show what has been done, what have you learned since the last six-week review. And, we find six weeks is a very good cadence, because it's short enough that you can remember the context and it's long enough... Six weeks is long enough, especially if you have, let's say, a team of a dozen engineers, you can do a lot. And not only that, you can do a lot in a day, but this is a check-in point. **Farhan Thawar** (00:30:59): And what I've noticed too with intensity is, let's say, we get a review and there's some feedback we get in that review. We don't wait until the next six-week review, right? The next day we are building things, we are iterating, we are tagging people. And then, by the next week's we're like, "Here's the trajectory." Right? Actually, I want to get that Elon shirt made, "What have you done this week?" Because, Parkinson's law is real. It sounds funny, but I keep bringing this up, but whatever time you allot to something will be the time it takes, right? **Farhan Thawar** (00:31:26): So, if you're doing something monumental, I don't know, you're doing a reorg or something, right? You can do it the slow way. "Let's sit down, and plan, and roll it out." And it's probably six months in most companies. Shopify, this is a week or two. You sit down, you're like, "Hey, this is the bones of it. Let's bring some more people and think." But then, it's going to start leaking. So we just launch it. Right? And, we do the same thing with lots of things. We just try to move more quickly and get out of the... We don't do change management, we just land it, and then go, "Hey everyone, it's a volatile company. This is what's happening. But this is how we get things done quickly." And then, move on with our lives. **Lenny Rachitsky** (00:32:00): Wow, there's so much there. I have been through the six-month reorgs. And, I think that context you just shared of, "We're at a volatile company, we're changing things. It's not going to be smooth, but we think this is for the best." It's just the culture of Shopify. It sounds like, "We want to keep moving fast. We know this isn't going to be the smoothest thing, but we just know this better to make the change at this point versus wait." **Farhan Thawar** (00:32:25): It's how Toby increased the resiliency in the company. He would walk around in the old days when we had a data center and just unplugged machines, right? **Lenny Rachitsky** (00:32:32): Chaos monkey. **Farhan Thawar** (00:32:33): Yeah, chaos monkey. You're right. But that actually works, because it just says, "Hey, by the way, shit's going to break. And so, let's be resilient to that." And so, same thing here. "Hey, by the way, someone's going to move your cheese. It's fine. We are here to create more entrepreneurs in the world. We're not here to have a six-month change management roadmap. And, that will just actually hurt the speed at which we can deliver value to merchants." **Lenny Rachitsky** (00:32:52): So, on all the things you shared, so there's weekly updates. So the weekly updates are each person shares what they're working on for the week. Is that the idea? **Farhan Thawar** (00:32:59): Each project. **Lenny Rachitsky** (00:33:01): Each project. **Farhan Thawar** (00:33:02): So, each project, it has an update, it might have a video of, "Here's the experience." It'll have a obviously a bunch of writing on what's changed since last time. We have a process called OK1 and OK2, which is like, OK1 is typically at the director level where they're like, "Okay, I'm aligned with the direction that this is going at." Or, "I'm not aligned." And they can make changes. Then, when it goes to OK2, it's typically the VP level of the area, who's now looking to say, "Okay. What you're working on actually aligns with the overall architecture. But by the way, have you looked at this context? Maybe you haven't seen this, this is happening, or the industry." And so, you're trying to align at that level. And then, again, like I mentioned, every six weeks we go through with Toby, and he's an intense guy himself. **Farhan Thawar** (00:33:40): And so, a lot of it is like, "Hey, why is this taking so long? Are we overthinking it? Are we not trying to move forward on this thing, because we're blocked on something? Is there some piece of infra?" Actually, I'll give you a good example. In one of the reviews from last time, there was an interesting AI problem we were trying to solve with LLMs that required us to have a very large output context window. And, most of the LLMs today have a very small output context window. But in the review, right, we have shared Slack channels with all the LLM folks, right? I messaged in the open AI channel, I messaged in the Gemini channel, whatever. And, within an hour we had increased the context on a bunch of major models and we were able to move forward through the thing, just because I asked. **Farhan Thawar** (00:34:29): And so, that's an example. It didn't take another six week review, but it increased the intensity, because the team was like, "Oh, we were blocked because we thought we had to now chunk up this data and do this thing because we had smaller output context and we thought we could do a big input context, but we'd have to do this caching." And, it was like this whole thing. I'm like, "Well, did we just ask them if we get bigger?" And then, they were like, "Oh, we don't have this as undocumented, but we'll just enable it right now for Shopify." And so, that created the intensity of the team to be like, "Oh, we can now quickly get unblocked." So that's the example of just moving quick and trying to just, again, ask a dumb question. I'm like, "This is probably not possible, but..." And then, they came back and said, "Oh yeah, we can do that." **Lenny Rachitsky** (00:35:03): That's a great example. And, as you're describing the ways that you create intensity and velocity within Shopify, it's interesting that what you're listing is a bunch of meetings and check ins, which to most people would feel like, "Why do we need so many..." There's all this like, "Less meetings." And I know you guys famously cancel all your meetings and that's a whole thing we can talk about. But, it's interesting that more check ins and regular check ins allow you to move faster. I imagine it's partly because it just makes sure you're not working on things that are unnecessary, and dumb, and not going to be used. And it's just continue to refine, these are actually the most important. **Farhan Thawar** (00:35:38): I mean, it's a combination of trust but verify, right? Because don't forget, the goal of the check-in is not for you to be like, "Ha, ha, I caught you not doing your work." It's not like the Dilbert boss, "Hey, did you do your thing?" Right? Even when I look at the Elon text, which is like, "Hey, what did you get done this week?" It wasn't to try to catch Parag in a, "You didn't do anything or you did a bunch of useless stuff." It was hopefully to pair on the problem, meaning, when I ask somebody, "Hey, did we move forward on this LLM project, because we now have this larger context window?" And then, they came back and said, "Oh, here's what we learned." So then, I can then look at the answer and say, "Oh, so now, have you thought of this? Have you tried..." It's a way to pair on the problem. **Farhan Thawar** (00:36:18): So, we have this word, everybody talks about micromanagement as a word, and we don't actually think it's a dirty word at Shopify, but the reason we don't think it's a dirty word is because it's not just, again, Dilbert boss saying, "Where did you do the thing?" It's like, "Hey, can I work on this problem with you? And if I work on this problem with you, I got to see where you are pretty often, and then give you advice, or you're going to share context with me, because I'm not in the work every day." To then come back and say, "Oh, based on what I know and what you know, can we move this in this direction? Maybe that's better for merchants." **Farhan Thawar** (00:36:50): I don't want to overuse the pairing paradigm, but it is really much like, "Can I pair with you?" And I learned this actually very early in my Shopify tenure, because Toby would have these one-on-ones with me and I'd be like, "Toby, you don't have to waste your time, man. You hired me. I got this." Well, he goes, "Oh, you misunderstand why you're here. We are here to work on problems together." And I was like, "Oh, I didn't even think..." I thought he hired me to take problems away. He hired me to work on problems with me. That's completely different than what I thought. **Lenny Rachitsky** (00:37:18): I love that. Okay. One thing you mentioned is meeting thing. For people that don't know what you all did with meetings, I think it might be worth just sharing that briefly, because it's awesome and something a lot of companies can learn from. **Farhan Thawar** (00:37:28): Yeah, sure. Actually, the funny story about the meeting Armageddon, is that, I was messaging Toby prior to me starting at Shopify about meeting Armageddon. And so, I actually think I had a little hand in him doing this before I got to Shopify. I was like, "Hey, have you seen..." I think it was Dropbox, "Have you seen a Dropbox is doing and Meetingageddon? And so, he was like, "This is super interesting." This is years before I started. So, I think it's funny that it ended up being a real thing. But here's what we do. Once a year at a random time, we will delete all recurring meetings that have more than two people, so not one-on- ones, and are internal people only, so not interviews or external partner meetings. And then, we have a two-week moratorium where you're not allowed to add a reoccurring meeting. You can have a regular meeting, but not a reoccurring meeting. **Farhan Thawar** (00:38:11): And the idea is that there's a lot of inertia behind a recurring meeting. It just always is there, and you know it's coming up, and it's hard to delete, because you're like, "Oh yeah, we talk about this thing every week." And so, what we do is we just do a meeting reset. And, I think, yeah, it's just called chaos monkey and the admins go in and just delete everything. Now what's cool about it is, it forces you to rethink, "Do we need a recurring meeting? Or do we just need one meeting? Or do we need a different cadence?" That's one thing. The other thing is it frees up so much crafter time, right? **Farhan Thawar** (00:38:42): One of the stats I track across engineering is how many hours are individual contributors in meetings per week? And we noticed that after we did... We did two things by the way. And I have a spicy second one for this, but the first one was we deleted meetings. And the second thing we did was we moved a lot of our Slack into Facebook workplace, which I'll talk about. Those are the only two things we did. And we saw a huge decrease in the amount of time crafters were in meetings. And then, we saw all kinds of other productivity enhancements, because they were able to have that flow time and work on things. **Farhan Thawar** (00:39:12): So, we're at something like three hours of meetings per week for an individual contributor at Shopify, which is phenomenal. Three hours a week is amazing. I think managers is not that bad. I think I tweeted this. I think it's six or seven hours per week. That's not bad at all, in order to get aligned. And then, all the rest of the time is work time. **Lenny Rachitsky** (00:39:29): And how many hours was it before Meetingageddon and Workplace? **Farhan Thawar** (00:39:33): Yeah, you're asking me a good question. I have to go look and see. But, it came down by something like 50 or 60%. It was something like five or six hours for individual contributors and came down to three. And then, the managers, I think it was 10 that came down to 6, something like that. But it was a huge difference. And the only two things, like I mentioned, were one was the Meetingageddon, the other one was like this, and I can talk about this. This is a- **Lenny Rachitsky** (00:39:53): Yes, let's talk about this. **Farhan Thawar** (00:39:54): ... Yeah. So, I mean, I love Slack. It's the IM tool. Everybody uses it. But it can for sure cause distraction. And so, what we did was we moved all announcement information. So, anytime you're sending a status update or large group announcement, we moved all of that to Facebook Meta Workplace, like Facebook for work basically, which is now being deprecated. So, we'll have to figure that out. But, it just moved all this stuff to a ML feed that you can consume differently than you would Slack, because Slack is like I message you and you see an alert and all this stuff, versus Workplace is like, "Oh, I want to go and consume content from the company, and get updates, and share updates." And so, that reduced a lot of distraction as well. And so, I'd love to figure out what the next tool for us is, but it is probably something more like a river of information that I can dip my toe into, versus IM and chat everywhere. **Lenny Rachitsky** (00:40:45): That is super interesting. So, specifically, things that are just updates where you don't need a discussion, you almost want to discourage a discussion. **Farhan Thawar** (00:40:50): Yeah, I mean, it has the commenting, but it's not the same tool. And, by the way, Slack is amazing, we use it. It's just that for this thing, it wasn't working for us. And so, we wanted to move that somewhere else. **Lenny Rachitsky** (00:41:03): I feel like, the more I dig into the Shopify way of working, the more fun stuff I never expected emerges. I'm curious what else is going to emerge. So we've been talking about ways that y'all, and you specifically, have created intensity, especially in the engineering organization. And then, you've also shared just broadly Shopify. What else is on that list? What else have you found helps create more kilojoules per hour? **Farhan Thawar** (00:41:24): Yeah, so again, I think there's nothing, I would say again, start from the beginning, there's nothing more than pair programming, because literally you can't do anything else but be on your computer. So pair programming is the number one. I will say, the weekly cadence helps a lot, right, which you mentioned. Again, which is part of GSD, which is sharing the updates, and then the six-week reviews, that does a lot. On the other side, we also have a lot of metrics and alerts that help us see when potentially things might be happening in the system that can allow us to be like, "Hey, wait a sec, there's too many things going on of this type. We probably have to sit back and reset and figure out what's going on." **Farhan Thawar** (00:41:56): So one thing that happened, for example, was we started seeing that it was taking a lot of time to develop in our admin, like engineers at Shopify developing in the admin. So we called, what's called, a code yellow, which is before code red. But code yellow is this idea of like, "Hey, we're going to call a code yellow on the admin." We want to make sure that the developer experience inside Shopify is really good. It should be easy to start up the repo. It should be easy to make changes, it should be easy to see the changes. And so, those are the things that, again, we can create intensity, because this code yellow allows the champion to tap anyone on the shoulder and say, "Stop what you're doing and come help this thing." Which is an infrastructure layer thing. And by building out this infrastructure, it allows you to go fast. It takes longer to build infrastructure, but it makes you go fast forever afterwards, right? **Farhan Thawar** (00:42:41): I'll actually give you an example of one of these. So, we in 2020, 2021, the heyday of pandemic, obviously, there was a crypto summer again and crypto was going nuts. And we were sitting back and saying, "Wow, a lot of our merchants are now asking for NFT gating." NFT gating, which is, "If you have the token, you can now go into the storefront and see my products. You can see my prices and you can check it out, but only if you have the token." And, we were getting a lot of demand from merchants to be like, "We want to do this. We want to sell an NFT. And we want our buyers to have the NFT to have this great experience." And we're like, "We agree. We want you to be able to do whatever you want. And so, we want to build this for you too." **Farhan Thawar** (00:43:18): And, sitting with Toby, he's like, "You guys are thinking about it wrong." He goes, "How long would it take to build NFT gating?" I'm like, "I don't know. Two, three weeks." He goes, "Now, how long would it take to build a platform layer, which exposes APIs so anyone could build NFT gating in one hour?" I'm like, "I don't know. Two, three months." He goes, "Do that." He goes, "Because you don't know what they're going to build on top of the platform." NFT gating is one thing, one use case, but if you spend the time to build out the infrastructure layer, he calls it putting gas in the tank, if you put the gas in the tank, people could drive on that gas for a long time going forward. And so, he goes, "I always want you to think about..." And the key part was, "What can you build so anyone could build this in one hour?" Right? **Farhan Thawar** (00:44:00): So, he does this thing to us all the time where he goes, "Oh, this should only be..." He'll say it and people get the wrong thing. He'll say, "Oh, you could write this in a day." And what he means is, "What has to be true so that you could write this in a day? What infrastructure do you need?" And, he actually develops this way. He will write code against an API that doesn't exist, because he's like, "You know what should exist here? This API." He'll write the code, he'll go back and forth and refine the client on the server, and then he'll go, "This is correct, the correct client code. Now, let me go implement the server code." **Farhan Thawar** (00:44:31): And this is notion of building things as infrastructure that sound slower today, because it's going to take... It's two, three months, instead of two or three weeks. But after that, the things that people built on top, right, were so easy to build, there were so many more scenarios that were emerged. It's just a different way of thinking about software. And, it's intensity in a different way, it's intensity around building this infrastructure layer, which we want to build quickly, but takes two or three months, in this case, but then can get everyone building on top of our infra in a much, much quicker way. And of course, who knows what can flourish from there? **Lenny Rachitsky** (00:45:06): It's interesting and it makes sense that so much of the way you all think is about building the best possible platform, versus the, necessarily, best possible point solution for someone. And it also explains why you spend so much time in crafting really great code and pair programming, because again, it's a platform for other people to build stuff on. So, I think, a lot of this is very useful, especially for platform businesses. **Farhan Thawar** (00:45:29): No, exactly. And actually, you're making me think of a stat. So, last year, maybe a tangent, but I tweeted out that GitHub Copilot has written over 1 million lines of code for Shopify. And people are like, "Oh my god." And it got picked up. And everyone's talking about it. And I go, "I don't know why is everybody getting so crazy, because what I want to see is GitHub Copilot deleting 1 million lines of code." That's when you know we're actually at this point where this is close to an engineer. Right? And so, we famously have deleted millions of lines of code this year, because we were trying to focus on, again, the sunk cost and rebuilding things elegantly, or you don't need this anymore and rebuilding. And I even tweeted out, I think someone said, "Oh, Shopify is in the top 10 Ruby code bases in the world." And I said, "I never want to see us on this list again." We shouldn't be gunning for number one, we should be gunning for number 100, right? We want to be not on this list. Right? Someone else can take the crown. **Lenny Rachitsky** (00:46:22): **Farhan Thawar** (00:47:22): Yeah, so there's a few things, right? One is, the more context you can fit in your head around a code base. And you can never really fit all of Shopify in your head, because it's a big complicated set of tools we give to merchants. But, the more you can simplify, the much easier everything becomes, resiliency, performance, reliability, maintainability, all the illities become much, much, much easier when the code base is simple. Now, all you need really is the mandate of like, "Oh, well, let's look at this code. And, if I could start this today, would I really build this thing? Or do I now have enough domain expertise to say, 'Oh no, this is the right solution?' So can I delete start over and build this more easily?" And now, everything else becomes easy to build on top of. **Farhan Thawar** (00:48:04): And so, routinely, we have a delete code club, we have hack days, which happens two or three times a year, where there's always one team that is focused on deleting code. They even have a manual, "Here's how to find things to delete." And, it's amazing. We almost always delete. I don't know if this is good or bad. We can always almost find a million plus lines of code delete, which is insane. But, at the same time, I applaud the teams for going after the cruft and the code base. And everything gets easier, right? Codelets loads faster. It's easier to understand. **Farhan Thawar** (00:48:34): This is why when I look at GitHub stats, you shouldn't really look at... I think Google put out and said, "Oh, 25% of all code is now written by AI." I'm like, "Where's the delete? Where is the 25% of all code is deleted by AI?" Right? This is where we have to start thinking about it. Because, the right code is never the volumous lines of code metric. It's always something else. It's always elegance. And that's where we have to think about. So, it is something that, as part of us being long-term infrastructure thinking, we really do care about that. **Lenny Rachitsky** (00:49:06): I love this, in part, because it connects to the topic we're talking about, which is speed, velocity, intensity, smaller code base, cleaner, better code base allows you to move faster. I used to be an engineer actually. But, both my engineering brain and my PM brain, I love the idea of killing stuff that's useless, fixing, making code cleaner, and better, and more durable. In reality, very hard for companies to prioritize this thing. Is there anything you found that helps you do that? You mentioned hack days and weeks are one part of that. Probably helps that Toby's an engineer and he understands the value of this stuff. But I guess, for folks that want to do this more, any advice? **Farhan Thawar** (00:49:42): Yeah. So actually, when we're building something, we think of it in one of three buckets. We're like, "Are you building an experiment, a feature, or infrastructure?" And, once you bucket things, you can say, "Oh, it's an experiment." You're like, "Cool. This is not infra. This is like, we're trying something to learn." And, by the way, that might turn into an experiment or infra, but it starts off as an experiment. Now, if you're building a feature, a feature is basically you're taking advantage of an existing piece of infra, right? So, token gating is the example I gave. If you could now build that in one hour, you would probably say, "Oh, we have the right infra below it." **Farhan Thawar** (00:50:14): But if you did what Toby does, which is, he's like, "Here's the infra I wish existed. Here's the feature. The feature might be quick to build, but now I have to go and build the infra." You're now slotting yourself into infra land, which is like, that could take longer, but you're now enabling it for a bunch of use cases. You don't have to think about it at once, because you may have people using your API in a different way. **Farhan Thawar** (00:50:32): So, I think you have to slot yourself. Now, how do people get into this mode? It is super, super hard. And, I would say, Toby is the secret sauce here, because he pushes us to think about things as infra almost all the time. I mean, one of the things that annoys me the most probably is that I'll always come to him and say, "Hey, we can do A or B." And he looks at me and he goes, "You know what I'm going to say, right?" I'm like, "You're going to say go back and generate more options." Because he doesn't like those. "I don't like A or B. Come back when you have something else." Right? Actually, maybe I'll tell you a little anecdote. He has a story where he says, "There are unlimited amount of wrong options for any problem. There's probably 10,000 right options, but everybody stops at the first right one, instead of what you should be spending all your time on, because the options that don't work, you're not going to spend time on. But you have to figure out which of the 10,000 options is the right one and spend time in what are all these right options? Don't just stop at the first one." **Farhan Thawar** (00:51:24): And so, when I come to and say, "A or B." I'm picking two of the 10,000. And he's like, "That's not what I... Go back and generate more options, because those are not the optimal ones." So, he is quite the philosopher on these things. And it does really change the way the company works, because he'll push you on these things. And then, we over time learn to spot the same patterns. And I learned to push my team on infra, and deleting code, and making things simple, because by the way, who doesn't want to get free stuff? Right? Free performance, free, easy to navigate code base, free maintainability, free resiliency,, because now, we went and did the hard work of deleting. It is hard. But that goes back to the beginning, right? Choose the hard thing. Don't just build the feature- **Farhan Thawar** (00:52:01): The beginning, right? Choose the hard thing. Don't just build the feature, go make the feature easy to build. **Lenny Rachitsky** (00:52:06): I feel like there's just more and more good stuff. What else is there that might be helpful to folks while you're thinking about it? And interesting, I was reading your tweet where you shared a lot of this advice, and you mentioned this briefly, but I think it's important with pair programming, one of the benefits is there's no multitasking. You're not checking Twitter, Slack while you're working because you're there being watched. And I could see why that is more productive just innately. **Farhan Thawar** (00:52:31): Oh no, for sure. Again, like underhand or free throws not only looks dumb, it feels dumb. People don't... They feel like they're wasting time sitting beside somebody and being like, "Well, I could be on my computer doing this thing." But together they are building a machine. Do you ever read the Undoing Project, which is about Amos Tversky and Daniel Kahneman, the famous philosopher. **Lenny Rachitsky** (00:52:54): By Michael Lewis, I think. **Farhan Thawar** (00:52:56): Behavioral economist. Michael Lewis. Exactly. And he said the famous line was "Alone, we're okay, but together, we're a genius." Right? That's a pair programmer. That's like two people. You're like, "Ah, we're okay. But together, we're a genius." And that's exactly what pair programming is. And hopefully me plus an LLM is a genius as well, but that's the genesis of that thinking. So I would say another thing that helps us create intensity is demo culture. So as part of the GSD updates, hopefully we encourage people to share high fidelity updates, which is not just imagery, but actually a demo. One of the things that can go wrong with just their screenshots is you don't really get the full experience. You can't tell how slow things are or whatever, but with a demo, so you can put a link. We have this tool called Spin, which is an internal development environment like a cloud dev environment where you can say, "Hey, click here to try this on Spin, and then you can try it and you can see how it works." **Farhan Thawar** (00:53:52): Or they say, "Turn on a beta flag in your own store and then try it." And so this short circuits a lot of misunderstandings, because you're like "I'm going to try it." And you're not waiting until the end, especially with a beta flag. You're like, "Hey, it's in my store. I just realized that I went in and now this page takes 20 seconds to load. Is that what you expect?" You're like, "Oh, we didn't find this use case." You're going to learn that much more quickly. **Farhan Thawar** (00:54:13): And that creates, again, intensity on the fidelity of the feedback you're getting because famously, some of our PM team will create a friction log. They'll be like, "I am walking.." They'll just create a screen share, create a video and go, "I'm walking through. I turn on the beta flag, I'm walking through this experience. Here's my feedback on the experience." And you're getting this high fidelity throughput coming back to you that you're like, "Okay, let's fix these things for next week's iteration and then share another beta flag and say, 'Okay, try it now. Try it now. Try it now.'" And so you're not debating about status reports, you're kind of debating about the experience. **Lenny Rachitsky** (00:54:46): So I'm trying to think broadly all the things you've shared, kind of how they fit together that allow you to move this fast. And I just looked up a few stats to give people a sense of just the size of the company today and how successful it has been as they hear the stuff we're talking about. So you guys are about 11,000 employees, something like that according to the Googles. And you're hitting not necessarily all-time highs on market cap because COVID gave you guys a big boost for a while, but you're kind of coming back to this insane valuation that you all had during COVID. So it's essentially all-time highs at a 10,000 plus person company moving really fast, shipping constantly. People love the product. And it feels like one key of what you're describing is essentially this operating rhythm that creates these check-ins that keep people moving and focused on the right sorts of tools and getting them quick feedback if they're moving in the wrong direction. **Farhan Thawar** (00:55:42): And having the leaders pair with those people on those problems, not just checking in, but actually pairing with them on the problems that they're facing. So you get both the crafters who are working on the stuff and the leaders who may have broader context working together to kind of unblock. **Lenny Rachitsky** (00:55:57): And it's so interesting that it's like, again, people often are often like, "We don't need meetings. Get rid of all the meetings." You guys do that, but also, there's a lot of power in strategic meetings and check-ins. Another kind of bucket is just the engineering environment, engineers working with engineers, pair programming, things like that. There's a tool you mentioned for pair programming, Tuple, I think. **Farhan Thawar** (00:56:17): Tuple. Yeah. It's funny because we use it exclusively, but we actually have this line internally, we call it, Shopify should be a crafters' paradise. It should be the place where crafters come to practice their craft and get better at their craft. Obviously, resonates from a lot of the engineering crafters, but it's not only engineering, it's UX and PM and ML, all the places where you'd want those people to actually have a great experience. We want them to come to Shopify because we believe this is the best place for that. **Lenny Rachitsky** (00:56:46): I love it. I just wrote a note down of just how you set up your teams for success. Oh, just avoid distractions. So I think the pair programming helps the workspace, workplace shift from Slack helps. I think you're also very firm on their working hours. You basically don't let... **Farhan Thawar** (00:56:46): No. **Lenny Rachitsky** (00:57:03): No. Okay. [inaudible 00:57:04] **Farhan Thawar** (00:57:04): No, not really. Yeah. We're not super firm on working hours from that perspective, but we do have a lot of people on East Coast time zones. A lot of stuff happens then, but we do have people all over the world. But I did mention we do have the check-ins and the six-week reviews on the cadence. So that six week cycle does give you a little bit of the, what did you get done and are you blocked mentality. And you can expect coming in a couple of times and being like, "Hey, we didn't get a lot done being unblocked." For you to change your approach to go, "Okay, I don't want to go to another review where we didn't get a lot done." So what am I doing this time to make sure we unlock a lot of progress? And that check-in can give you that ammo to be like, "Let's do this this time." **Lenny Rachitsky** (00:57:44): And you're also remote first as a company. **Farhan Thawar** (00:57:46): Yes. **Lenny Rachitsky** (00:57:46): Which I think is especially cool. Now a lot of companies are going back to not remote. You guys are staying remote. Why do you guys decide to do that? What have you seen as a big benefit of that? **Farhan Thawar** (00:57:55): Yeah, so we have this remote, so I like to call it 90% remote or 95% remote because we have these intentional IRL experiences. So every summer, we just started last year. Sorry, this year. We're doing this thing called Shopify Summit where we bring the whole company together, get together and it's a combination of talks plus hack days and it's a come together experience like food and parties and bands. And it's a super fun way to re-energize and rebuild your trust battery over time. And then we have this thing called bursts, which is, "Hey, you want to work on a problem? You need to prototype, you need to hack." People can just say, "Hey, I'm starting a burst. We're going to have five people. We're all going to go to Ottawa or Toronto or Montreal or somewhere else and we're going to talk about this problem and get together." **Farhan Thawar** (00:58:38): And so a combination of those two things mean throughout the year, you can recharge. We have the trust battery notion, which is how much trust can you have between people and it can deplete over time if you're remote. So then we have offices which are like, come in if you want. Like I mentioned, I come in once a week and now Toby moved to Toronto, so now I'm in three days a week. But it's like if you want to come in, you don't have to, right? Today, I work from home, but tomorrow, I'm going in. And that allows you, again, to have those random interactions and allow you to feel like, yeah, we're 90 plus percent remote. But I would say the main reason is we want to hire the best people in the world and those people can be anywhere and just happens to be that not all of them are near an office. **Farhan Thawar** (00:59:20): But again, with the bursting, here's a good example. For Black Friday, Cyber Monday, I encouraged all engineering leadership to come to Toronto. We're all going to be in the office watching the graphs. And then for hack days, I try to get people to go to the ports, which we have four of them, Toronto, Montreal, Ottawa, and New York, which again are come in if you want, but then get that IRL. And so it's kind of a little bit of a combo. I wouldn't call it hybrid though because you don't really have every Friday you come in or don't come in. It's more like, come in if you want. **Lenny Rachitsky** (00:59:48): There's so many things to talk about. This trust battery metaphor by the way is awesome. I've learned to use it also. And again, it's just basically everyone, your trust with someone is like, think of it as a battery that can deplete and grow and you should try to charge it up when you can and then use that charge over time. **Farhan Thawar** (01:00:06): And it can be strategic by the way. I've seen people use it as a... I'm pretty sure Toby says he starts everyone at 50% and then he gets to know you. And then I've seen people use it as the opposite, saying, "Hey, look, this team is hard charging. I'm going to start you at a hundred. Assume that you already have high trust, do the things, and only if you are doing things that are off alignment, does your trust battery deplete." So I've seen people use it, the terminology as a shortcut way to figure out how to work with somebody. **Lenny Rachitsky** (01:00:30): I love just how first principles you all are, and there are so many things are so unique to how you operate and clearly it's working. And so I feel like we just keep going on and on. I want to talk about hiring. I know you have some pretty unique perspectives on how to hire people that are awesome, but also, hire them quickly. But before we get there, is there anything else that you think might be really valuable to share in terms of intensity, velocity, moving fast? **Farhan Thawar** (01:00:53): I think the personality of the leadership team is quite intense. We have a lot of founders on the exec team, which are impatient, intense people by design. But even some of the non-founders are just accomplished people who tend to be pretty, we all have this attitude of impatience, and so maybe, I don't even know if that's a learned skill you can learn or if it just comes along with your personality, like genetics. But we typically, even at the leadership team, for example, we try to do, here's my weekly thread of all the things that are going on so that we can not only share, but also show progress on things. And then someone can jump in and say, "Oh, this thing you're doing, it relates to my thing that I'm doing over here." It creates this notion of, there's a lot going on all the time and we want to keep the vibes, keep the energy high. So a lot of high energy intense people. **Lenny Rachitsky** (01:01:45): It reminds me while I was at Airbnb, it felt like no matter how well things are going, it always felt like Brian especially is just pedal to the metal. No matter how well things are going, it's not going well enough. How do we go faster? How do we do more? **Farhan Thawar** (01:02:00): Well, I would actually go further. I think if you don't have two or three big projects that are on fire, you're probably not pushing hard enough because you're not really trying things that are outside of your... If everything's going well, are you really taking the risks you need to be taking? So I think you have to over-rotate a bit and there should be a few things on fire at all times, not because you should create that, but it should just happen because you're stretching into new things that potentially or you're going faster than you should have, or there's a new leader you've counted on early because all these things that should create this thing of it might work. And so you want to have a little bit of chaos at the edge. **Lenny Rachitsky** (01:02:39): I love that. And it may sound stressful and why would I want that? Why would I want to work with chaos and fires everywhere? But in reality, if you don't, your business is unlikely to become incredibly successful and that is even more stressful and painful. **Farhan Thawar** (01:02:55): Correct. Yeah, it's like the opposite, right? It's like this idea of people feel like the comfort gives you stability, and really the uncomfort gives you stability because now you're constantly learning and that makes you more robust against things that could come across. **Lenny Rachitsky** (01:03:11): Choosing the harder path, some might say. Okay, let's talk about hiring. You have some really interesting takes on hiring. One that I've heard about is that you don't like the interview process. You kind of like to prefer not to interview and do something instead. Talk about that. **Farhan Thawar** (01:03:28): Yeah. So throughout my career, what I've noticed is that, and I'm sure everybody, this is a dirty little secret, right? Interviews are not a good predictor of performance. We know this. We know this from studies. We know this. Everybody at their company knows this, where somebody interviewed well, wasn't as good in the job or the opposite, didn't interview well and then came in and was phenomenal. One example I have from my startup right before we came to Shopify was I hired two people for machine learning. One was a PhD, taught at the university, was like, oh my god, no brainer, was also recommended by an employee. We're like, "Oh my god, this person's going to be great." The other person was a dude I met at the coffee shop who had never had a software job but was just so interested in machine learning and person A, we let go within a few weeks because not a fit for our culture. **Farhan Thawar** (01:04:12): And person B was at our startup and is still at Shopify today and is a phenomenal machine learning engineer who literally at our Christmas party was like, "This is my first software job." We're like, "How?" It was just so cute. And we gave them both the shot. The key was I didn't use the resume in either way to bias. We brought them both in. We said, "Here's the environment." It was all pair programming at my startup. And so they pair program, and actually as an aside, I really believe in pair programming when I made people work in pair programming with my own money. I paid for two people to be on one computer. So that's how you know... **Lenny Rachitsky** (01:04:50): Less than half the code. **Farhan Thawar** (01:04:51): Yeah, exactly. Right. Less than half the code. But anyway, so pairing. And it was pretty clear after just a few weeks, I would say let's say up to three months is the amount of time I give people, that person A wasn't going to work out than person B was. So what I really like to do is use this race car analogy. If I told you, "Hey, I want to go hire the best race car driver," there's not really that many questions you could ask them except for put them in the car. And so the same thing happens with us is that of course, we have to do interviews, but we do really spend time in the 30, 60, 90 days to make sure that the thing that they are bringing actually lines up with what we need at Shopify. And you should also be transparent with people because if it's not a fit, it's actually good for them and you to figure that out as quickly as possible because they could be amazing somewhere else. **Farhan Thawar** (01:05:39): We mentioned the chaotic environment and fast moving environment Shopify is, that's not for everyone, but that's okay, right? We're not looking for... We've talked about that we want to be as the best 10,000 person company in the world. We're not looking for millions of people. We just need the best 10,000. And so if it's not a fit, it's in your interest and our interest to figure that out quickly so that you can go somewhere where you will be amazing and for us to have the people who will be amazing at Shopify. And so job trials, I'm a huge fan of, which leads me to intern programs, what a great interview process because you now have real work product from somebody for four months. They get to see what it's like to be at Shopify for four months. We get to see what it's like for them to be at Shopify for four months, and that can turn into a full-time gig. **Farhan Thawar** (01:06:21): And that's a great interview process because you literally know exactly. You don't have to... I'll give you a funny example. I think I've heard a company where, "Oh, we have an intern process and then afterwards, we interview them for full-time." I'm like, "What are you going to learn from let's say even eight hours of interviews that you're not going to have learned from four months of real work experience?" And so there's just things like that. You just got to look at the work product. And so I'm a big fan of job trials, and in my previous companies, like you mentioned, I almost didn't interview anybody. I almost just said, "Come in and work." And it allowed us... We had a much higher in the first 90 days, like 20% attrition before 90 days because it just didn't work out. But those after 90 days, we had less than 1% attrition because they knew exactly what they're getting into and we knew exactly how they were going to fit. **Lenny Rachitsky** (01:07:04): So in terms of the hiring process, you're still at Shopify. You're interviewing people, they're doing technical evaluations, things like that. But it sounds like there's a very strong setting of expectations. "We will hire you, but we'll actually clarify if this is a good fit in the first 30, 60, 90 days and we're going to do... We may let you go and there's a good chance we may let you go." Is that just the way you set things up? **Farhan Thawar** (01:07:27): Yeah, I think the way to think about, it's more like we want to make the interview process as close to the real job as possible because by doing that, we can likely assess the skills that you have in your interview closer to what's happening in the job. So that's one. Two, we have this interview step called the life story where we try to figure out if, are all the experiences you've had up until now actually going to be... Does it show that you are a curious person with range? Because if it does, that's likely more of someone who's going to be a fit. I had this famous line from somebody who said, "You know what I don't like about resumes?" I'm like, "What?" They go, "It tells you what you did, but it doesn't tell you why you did those things." **Farhan Thawar** (01:08:10): And it's such an interesting insight. Your resume should be a why, like why did you go from this company to this? That's the interesting part. Not that you are a PM at Microsoft and a PM at Stripe. It's like, why did you switch from Stripe to Microsoft? There's something interesting there. And so the life story is trying to pull that out. It's like, why did you make the decisions? What did you do in your past that was interesting? Are you curious? I always thought... I read this great book, Range by David Epstein. That book was maybe one of the hardest books for me to read in my life because every page I was like, "I don't believe it." I kept thinking I was a specialist. I kept turning the page going, "I don't like this data that keeps showing that generalists are better." And then by the end, I realized that I'm a generalist. It took me so long to realize, and funny for me because I ended up redesigning the compensation system for Shopify, even though I'm an engineer. **Farhan Thawar** (01:08:56): So I still thought of myself as an engineer through and through, even though I work on recruiting and HR and all these other things. But I think that that's what we're trying to tease. And then yes, in that first period, we actually have a survey that goes over Slack that says, "Hey, how happy are you with the person that you hired?" And that should, in conversation with the person, you should give them the feedback to figure out, "Hey, are there things you need to adjust to better fit in and make sure the expectations are set up?" But then also, together with the person, figure out, "Hey, if you're not feeling this, let's find you either a different role in the company or somewhere else because we want the people here to have high impact." But that person should have high impact somewhere, could be at Shopify, could be in the same role, could be in a different role, could be at a different company. But that's a good thing for everybody. **Lenny Rachitsky** (01:09:41): And then do you actually do work trials with new engineering hires, or is that something you aspire to do? **Farhan Thawar** (01:09:46): Yeah, I would love to do it. It's hard to do with the volume resumes we get, but we do do it at scale with the internship program. So like 2025, we're going to hire a thousand interns, and that is going to give me a thousand job trials to pick the top X percent of those to come to Shopify full time. **Lenny Rachitsky** (01:10:03): So just to double-click on that, so you're hiring a thousand interns over the course of the year. That's a lot. And the idea there is these folks are actually useful building useful things, and it's an interview process for the internship. **Farhan Thawar** (01:10:17): Yeah, I think it's two things. One is some people look at an internship program as community service. Let's give back to the community. Let's hire early talent. And I'm like, "Hold on a sec. Are you telling me I could hire a thousand people over the year?" And they will come to work with an LLM and a brain because they're growing up in the age of AI. They will be useful to us because they come from a different generation and they have, in our case in commerce, they have a different experience about shopping and AI and bots and chat and voice and all these things. They'll be useful to us. We'll teach them some stuff as well. And then together we can decide if they might end up going somewhere else, in which case, we have the Shopify imprint on them going to whatever other company, which is I think a positive, or they might stay at Shopify and be useful over a longer period. **Farhan Thawar** (01:11:02): It seems like win, win, win. The other thing that was cool is after I did that tweet, a bunch of other CTOs messaged me and said, "Hey, we're going to hire 1,001 interns to beat you guys." And I'm like, "Great." Just from that one tweet, if I can get the early talent ecosystem restarted here after a really tough last few years and layoffs, it's great for everybody because now they're realizing that they also realize that these people are super valuable and they bring together a completely different set of skills. And by the way, here's a secret in pair programming, interns will always be more intense than the full-time. And so that also helps the flywheel of intensity go for it. **Lenny Rachitsky** (01:11:40): It all just keeps coming back. Did the internship program emerge out of this co-op system that Canadian schools have and a Waterloo has a big co-op program? **Farhan Thawar** (01:11:49): Yeah, I went to Waterloo. And so yeah, hint, hint. So I went to Waterloo and I did co-op and I did intern programs there. It was amazing. What a great experience, because what ends up happening is you leave Waterloo with your degree, but also with two years of experience because I did six four-month work terms, 24 months, and you end up walking. I think one of the big parts of it is just interview skills because I interviewed for 10 plus jobs every four months, and I did that six times. And so you come out having done lots... You have a lot of interview experience, but you also have work experience. And so just taking that to the next level, Shopify has always had interns. And what I felt like we needed to do was, again, restart this notion of early talent in the ecosystem. I would say one or two big differences with our intern program. **Farhan Thawar** (01:12:36): One is we're making them come in three days a week versus full remote. And the reason for that is, and we're doing it just in three offices right now in Montreal, Toronto and Ottawa. And the reason for that is because we want them to have a cohort because early talent is different than you and I who've been in the industry. We worked in office, we worked out of office. We're more comfortable with navigating partnership discussions and talking to people in different companies. But these people have not. They may have never worked anywhere. **Farhan Thawar** (01:13:02): And so to not have the IRL component would do them a disservice. And so we specifically made it in those ports and the people are traveling by the way, they're moving to Montreal to do the internship. It's great. And then if you're a mentor or manager for one of the interns, you have to at least see them like IRL once a month. So we're kind of making these experiences. And of course, they'll have a cohort of dozens of people that will be with them along the way. And so we think that'll just make their experience better. And of course, nothing like tapping someone on the shoulder and be like, "Have you seen this era before?" And so it's easier in an early talent situation. And then of course over time, if they become full-time, they can still come to the office. It's come if you want, but they can also go full remote. **Lenny Rachitsky** (01:13:39): That is amazing. For folks that don't know anything about these co-op programs briefly, it's just basically while you're in school, before you graduated, during the summer, you go work at a company. **Farhan Thawar** (01:13:39): No. **Lenny Rachitsky** (01:13:48): Oh, during the year. Okay. **Farhan Thawar** (01:13:50): Yeah, it's during the year. So what happens at Waterloo is, what I did was I did eight months of school at the beginning. So two terms. My first co-op term was summer, but then it was work, school, work, school, alternating for the whole rest of my time at Waterloo. **Lenny Rachitsky** (01:14:02): It's like semesters alternating. **Farhan Thawar** (01:14:03): Exactly. So every four months I did either school term or work time. So I was doing work in January sometimes and September sometimes. And it was super good because again, it also allowed me to be super intense at school for four months and then go to super intense work experience for four months. But yeah, it's a model that... I was just at Waterloo this week doing a talk, so I love that symbiotic relationship between Waterloo and the employers, by the way, not just Waterloo. Lots of schools do a summer program, UFT and others, lots of schools in the states. **Lenny Rachitsky** (01:14:32): Fun fact. So total tangent, I had a startup called Local Mine, started it in Montreal of all places. I'm not Canadian, but moved there for various reasons. It was awesome. And our first hire was actually from the co-op program. I don't know if it was Waterloo, his name is Nick Adams. And he applied. Just he saw our job posting, I think, and were like, "What is a co-op?" And he came to work and then he went back to school, and then we hired him, and then he ended up at Airbnb when we got a card. **Farhan Thawar** (01:14:59): There you go. So for us, actually, when I did my startup Helpful, I had one or two engineers, and then I actually literally just hired four interns because you hired them in February for May. And because I was doing pair programming, I had to make sure I had four full times by then. So I hired the interns in anticipation of having the full times. And I literally had, I think I was off by one week, so one intern had no pair for a week, but then after that in May, I had four full times, four interns, and then they paired the whole time. **Lenny Rachitsky** (01:15:31): What a journey. I want to talk about just one other topic real quick and then we'll wrap this up. And it's around XtremeLabs. So there's a bunch of stuff here. It feels like it's just like this tech mafia of Canada that a lot of incredible people emerged out of, and there's a whole bunch of stuff we can talk about. One fact I heard while you were there is you had a hundred reports, direct reports that reported to you. **Farhan Thawar** (01:15:56): A 120. **Lenny Rachitsky** (01:15:57): 120 direct reports feels like a complete nightmare to me. Tell me why you decided to do that, if you'd recommend that for other people. **Farhan Thawar** (01:16:05): Yeah, so what ended up happening there was we started off small. It was 10 people. When I got to XtremeLabs, I wasn't the founder, but I was very early on and I just had everyone report to me. And then as we grew, I just kept having those people report to me and I was trying to figure out, we talked about crafters and crafters paradise, this idea of people don't really... Their managers are useful, but I was trying to figure out could I solve the problems that they needed their manager for in other ways? So for example, what should I be working on? I was like, "Okay, well, we have product backlogs" or "I'm blocked on something," or "I need feedback on the product I'm building," or "I'm stuck on this technical problem." I tried to figure out ways to not have managers be the answers to those questions. **Farhan Thawar** (01:16:48): I'm like, "There should be another answer." And so pair programming really helps you get unblocked quickly because you have another person that you can bounce technical ideas off of. Having a product backlog can tell you what to work on. We had demos every week, demos internally, and then we had demos with the clients every week because we were a contract manufacturing for mobile. That gave them feedback on whether they were going in the right direction. We had set working hours, which made things super intense in the office. This is again like 2009 to 2013. So all these things didn't really need a manager. And what I realized was what the unblocking thing needed a manager. I'm blocked on this. Well, I said, okay, if... I had all these directors. I did two things famously. One, I had a lot of direct reports, and two, I did not do any scheduled one-on-ones because you can't have 120 direct reports and do a scheduled one-on-ones because you're never doing anything but one-on-ones. **Farhan Thawar** (01:17:31): So I said, "I'm going to be around a lot because I don't have a lot of one-on-ones. So we can do unscheduled one-on-ones." And what that means is if you are blocked, actually there's a famous picture where I had this weird cube desk where it was like a circle almost in the middle of the whole floor of engineers. And I was always there because I wasn't in a lot of meetings and people that were blocked, they could just come up to me. Actually, one cool thing about pair programming IRL is you can look across and just see if it's working or not. Because if two people are intensely on the computer, you know it's working. If one person is laying back or you're like, "It's not working," so you can just walk up to- **Farhan Thawar** (01:18:00): It's working if one person is laying back or you're like, it's not working. So you could just walk up to them and be like, "What's happening?" But they would come and ask me questions and I can unlock them. Like, hey, we're blocked on this. We don't have this API. We need money for this machine, whatever. And so the unscheduled one-on-ones ended up being a real clarifying thing for me. Because I did scheduled one-on-ones my whole career and I realized after leaving Microsoft for three years, I'm like, where are all those one-on-ones useful once a week for three years, right? A hundred and fifty one-on-ones. **Farhan Thawar** (01:18:26): So the unscheduled ones were, though. I was like, when I knocked on my manager's door and said, "I have this problem, those were important." So that's what I created at Xtreme. And the 120 directors, it just grew over time. I just didn't think I needed managers. So I was like, let me unblock these people on another way. And we came up with other things to systems to unblock them that didn't require a manager. And I just also had a good memory. I knew exactly everyone's skills and compensation. I knew all that off the top of my head, so that helps. **Farhan Thawar** (01:18:54): The thing that I broke was actually, this is Chamath. He came in and became our biggest investors. He's obviously is a smart guy, but he said the right thing, which is not, this can never work, because then I would go into defense mode and explain to him why it would work. He just said to me, I'm not going to debate with you whether this works or not, but will it work at 400 people? And I said, probably not. He said, okay, so let's change it. **Farhan Thawar** (01:19:16): And so we did then ended up putting a little bit more of a structure, but I made a few people directors and I forced them to have 40 direct reports each. I said, we're just going to make it still pretty flat. And then that did end up working, because it still allowed them to use the system to unblock people versus having to do a one-on-one every week, or having to talk about things that potentially a system could unblock. And so I tried to figure out ways to systematize things. **Lenny Rachitsky** (01:19:45): I love it. Just another example of doing things differently, not necessarily just, here's how it's done and I'm going to do it that way and experimenting with it. Even if you knew, okay, maybe long term this isn't the way it's going to operate. I imagine at Shopify you don't have 120 reports. **Farhan Thawar** (01:19:58): No, we have fourteen or something. We do have these guardrails where I think we say, Hey, in engineering you should have between eight and 20. There are definitely people who have more and people who have less. But we do try to keep things as flat as possible, because we do believe that it doesn't make sense to have three people reporting to and then to somebody, and then they only have three people. You just make a very deep hierarchy. We actually do see, by the way, the farther you are from Toby, we can see things in the survey results. The alignment gets out of whack, and so you do actually see that you want to be closer, you want to have a flatter org in general, and that can be achieved by just having more direct reports per level. **Lenny Rachitsky** (01:20:39): Makes sense. Okay, final question before we get to our very exciting lightning round. We have this recurring segments that I call Fail Corner where generally people come on these podcasts, they share all their successes. Here's all the things that I've done, right. Here's all the big wins. And everyone feels like, oh man, I wish I was always successful people. When in reality, everyone that comes on has failed many times. Is there a story of a failure in your career that you could share that helps people see that even folks like you fail, and maybe what you learned from that experience? **Farhan Thawar** (01:21:10): I have a few. I'll say one thing by the way, because I think I read this in Tim Ferriss's book or in the podcast where he said, create a failure resume and write everything down. And I would not recommend doing this because I did this and I got super... I'm like a high energy happy guy. I wrote down, I have a note on my phone called Failure Resume, and I wrote down all the times I failed and it is depressing. So I would not encourage people to do that, but I'm happy to tell you about a few instances. **Farhan Thawar** (01:21:33): So well, one is actually I've been laid off twice and people would not expect like, oh, I'm doing this thing and I've been laid off twice. And I think in both times it was the right thing, it was the right thing for the company, the right thing for me. **Farhan Thawar** (01:21:45): And I kind of used that experience as a way to reevaluate and eventually came out with my framework of how I want to spend time. But that's maybe a different story. **Farhan Thawar** (01:21:54): I'll tell you about one at Shopify, the first week that I started, 2019, we were rebuilding our point of sale system, which now does billions of dollars of GMB. But back then we were like, well, let's rebuild it with a new UX and a new technology platform. And it was my first week and I'm the mobile guy, coming from Extreme Labs. They're like, should we build this in React Native, or should we build this natively on the mobile platforms? And so I went through this evaluation, spent a lot of time, blah, blah, blah, and I came back with a hedged solution, which is kind of dumb. I said, let's do iOS and Swift and let's do Android in React Native. And the reason I said that was I said, I want to learn about React Native and I think Android's the harder platform, so let's build that in React Native, but iOS on Swift because that guarantees us a product in market. And we didn't have any React Native apps in market at the time. A year later we launched the iOS version and it was a huge success. And we then spent another six months building the React Native version for Android and everything else. And we realized pretty quickly that React Native was the platform for the future. We were like, oh my God, this will allow us to have one platform. You could run it on the web as well, and we could use the React engineers from the web to work on it. It was a clear winner. By then, we had also launched a shop app, which is React Native. **Farhan Thawar** (01:23:11): And so we learned a lot about this. And I went back and I said, hey everybody, I made a huge mistake. We just spent a year building this thing. It's in market, but we're going to have to rewrite. We're going to have to rebase back onto this iOS version. And I think I burned 18 months of time with a hundred engineers, literally from the decision I made in the first week of joining Shopify, and Toby, when I went to Toby and I told him, I go, hey man, I think I made this mistake and we have to do this and it's going to cost us a hundred engineers, another six, whatever. And he looked at me and he goes, you should tell everyone this story. That's all he said. Not like, hey, bad, good. He goes, did you learn something? It was an epiphany for me, but he was like, this is a learning org, and I totally failed and I told everyone I failed and my mistake and everything else, but he goes, just tell everyone because he goes, do you know what mistake you made? **Farhan Thawar** (01:23:57): And first I was like, I don't think, like, what mistake. He's like, you didn't take. He goes, I will always come down harshly on people who do not take risks, and you did not take a risk in this case. But if you take a risk and it doesn't work out, you'll never get in trouble, because you took the risk and it was the right risk to take, but he goes, but you didn't take the risk. **Farhan Thawar** (01:24:16): And so what I should have done, and by the way, even now thinking back it would be super hard to do, first week at Shopify, right, is take a risk on a platform that we have not launched in production app on, but he was correct in that we should have, because we would've saved ourselves so much more time. So yeah, total failure, sorry. The product is super successful now and we're all on React Native and even the Shop Green app is on React Native. Everything's React Native, and we're core contributors. It's all good. But I literally burned I think 18 months of time for a hundred engineers as my first decision in the company. **Lenny Rachitsky** (01:24:48): This might be the best example of failure coordinator we've had yet. This is a great example. Both of them actually are, although I'm wondering, okay, that felt like a really good decision to me and it's- **Farhan Thawar** (01:24:58): It sounds like it, right? But It wouldn't have been his. **Lenny Rachitsky** (01:25:02): But it's, obviously you don't want to just take risks. There's a limit of a risk but informed, I guess. Is there anything you missed there that would told you this was the right path? Because in hindsight, of course we should have done this, but looking back, what do you think you should have done other than we should have done the risky path? **Farhan Thawar** (01:25:19): Yeah, I mean one thing about my career as well is I don't really do anything halfway. And when I started looking into React Native, it was never just that I'm going, oh, let me look at the docs and read and build a thing. It's like I flew to Meta and met with the React team. I became a core contributor. I ran the React Native working group, like we became release captains for React Native. I knew that I was going to do all the things, so I'm like, and of course in React Native you can also drop down to native and do things there that are not possible. So I think I hedged incorrectly. I knew I was going to do all these things and I should have looked at my own thought process, say, if I do all the things, can I fail? And I didn't take that into account because again, I did five or six. **Farhan Thawar** (01:25:58): I literally, I put everyone together. I was running the group, I was like release captain. I would hang out with the React team and Meta, we're doing all the things. We became core contributors at React Native before we became core contributors and react because of all the things I was doing. And so I think just knowing that I was going to go all out, I should have said, you know what? This is not going to fail. And I didn't have the confidence in that path, so I hedged, right? Hedging is the worst. And I remember the CTO at the time said, I'm wondering if I should force you to go React Native. He literally said that. And I said, I will do if you say that, I will do it, but it would've been his decision. And so he didn't do it. He didn't tell me to do it. **Lenny Rachitsky** (01:26:36): Okay, that makes a lot more sense. It's so funny that Facebook had a similar mistake early on in their career- **Farhan Thawar** (01:26:44): HTML5. **Lenny Rachitsky** (01:26:45): Yeah, exactly. I know. I don't know if you were at Zuck's interview at the Chase center that the Acquired podcast did, and he talked about this where their market cap dropped 80%. They were about to go public. They went with this app. No one thought they could do mobile ads. And he's like, that set us back a year and a half. He's like, but based on all the pain he's gone through back since then, he's like, that was not too bad. **Farhan Thawar** (01:27:08): Yeah, it's true actually, maybe what people don't know is, I was at Facebook, XtremeLabs, worked on the Facebook app and we worked on that app. I was in the office when we submitted the iOS app every single day that week, because it kept crashing. And we had obviously direct access to people at Apple, but we'd ship a new app on Monday and it crashed ship an app on... Not just us, but us, Facebook together. And so I remember that whole HTML five fiasco from the inside. **Lenny Rachitsky** (01:27:36): I thought you would say you also told Facebook to decide on the HTML5 app to set them back a year. **Farhan Thawar** (01:27:41): I did not. We happened to be there when they were doing it. Yeah. **Lenny Rachitsky** (01:27:45): That's so funny. Amazing. Thank you for sharing that. Before we get to a very exciting lightning round, is there anything else that you think would be valuable to leave listeners with, either touch on something you've mentioned, a last piece of nugget of wisdom, or we just go straight to the round? **Farhan Thawar** (01:28:01): Yeah, I'll say something maybe embarrassing for you. I've been using your performance management framework from your first round review article, not knowing by the way that it was you. I actually found it, you being the famous Lenny podcaster, but the old days, maybe the Lenny, the PM. And I remember reading this a long time ago and just copying, there's a Google link in there to a Google Doc link with a template for a performance review framework that I've been using for years. **Farhan Thawar** (01:28:32): Literally every review I've done at Shopify uses that framework. And I was writing a post to my admin about how we can use LLMs to make it easier for me to write these reviews, even though obviously you have to read it all and go through it, but I was like, how can I generate some of this with an LLM? And so I wanted to send her the original article. So I went back to the first round review, I found the article and said, oh my God, it's Lenny, the same guy. **Farhan Thawar** (01:28:54): So I will say one thing that's interesting about that framework is, I've used it now for, like I said, six years here, is that, and I don't think it's me. I think it's actually the framework pulls out good information. I've had multiple people in a review process tell me that, when I deliver the feedback in, of course the format, they would say, wow, I've been in industry a long time. This is the best performance review I've ever had. And it's because the framework pulls out good information. So congrats to you. **Farhan Thawar** (01:29:21): But I think it was funny that randomly I was coming on this podcast and I just wrote that doc to my admin two, three weeks ago and realized it's the same person. **Lenny Rachitsky** (01:29:29): Well, how about that? I love that. I'll also give credit to a four board guest on this podcast, Vlad Loktev, who was my manager at Airbnb, and that's where I was inspired to write about that framework. **Farhan Thawar** (01:29:29): Amazing. **Lenny Rachitsky** (01:29:41): So it trickles down to him and I don't know where he boarded this, he probably invented it. So credit to Vlad also for that. Another fun fact along these lines, I have another first round of repost about the W framework, which is a framework for planning. They do annual planning. And that's one that I've slowly discovered many, many companies use and they don't know where it came from. They just call it, oh, we have this W framework. Someone flipped it and call the M framework. But that's another one that has trickled into the ether of tech companies, which is awesome. **Farhan Thawar** (01:30:10): Amazing. **Lenny Rachitsky** (01:30:12): With that, Farhan, we have reached our very exciting lightning round. Are you ready? **Farhan Thawar** (01:30:17): I'm ready. **Lenny Rachitsky** (01:30:18): Let's do this. What are two or three books that you have recommended most to other people? **Farhan Thawar** (01:30:23): There's one. So Toby has an annoyingly long set of books that he recommends, and they're all, not all, they're usually good, depends because we're not totally in sync on fiction, for example. But he recommended one to me that I think everyone should read right now called Manna, M-A-N-N-A, from Marshall Brain. It is a book, it's a book about AI. And I think the most interesting thing about it though is about a future in which the AI tells the humans what to do. So it's this idea of, imagine in the future you came into work and the AI would tell you what emails to pay attention to or what dashboard to look at because something weird is going on. It takes that to an interesting level. So I would recommend reading that book. It's not long. That's fun. **Farhan Thawar** (01:31:05): I think another book that I recommend to people, and it's a weird one to recommend, but it's Business Adventures from John Brooks, the famous, if you ask, I think it's Bill Gates, what his famous book of all time is, it's this book. **Farhan Thawar** (01:31:16): And the cool thing about the book is that it is not easy to digest for anyone with focus problems. Paul Graham wrote the post How to Do Great Work, and it's super long. The best part about that post is that you have to be able to read the whole thing. And so the same thing with Business Adventures. I think each chapter is, it's 12 chapters, 12 stories, no breaks in between. It's just each one is super long. But it just goes into a problem at such depth that if you can maintain your focus to get through the depths of each problem, you will just learn something, just like that post by Paul Graham. **Farhan Thawar** (01:31:51): I loved that it was so long because I sent it to people and I said, the test here is can you read it? Can you just get to the end? And not in a pejorative way, like in a... If you can get to the end, you will extract the alpha from this post if you can read it all. So those are... Manna is like the opposite. It's very easy and easy read. **Lenny Rachitsky** (01:32:11): I'm excited to read these. Next question. Do you have a favorite recent movie or TV show you really enjoyed? **Farhan Thawar** (01:32:18): A recent one was Challengers, the tennis movie, with Zendaya just randomly I was at home and I put it on and the cool thing about it was more the cinematography and music. They had this weird style, art house style, where they would be talking and music would get super loud. It was very strange, but a very, very good movie. And then you saw, you said movies and- **Lenny Rachitsky** (01:32:40): Or TV show. Oh, TV show, anything like that. **Farhan Thawar** (01:32:42): Yeah, one of my all time favorites is probably Halt and Catch Fire. I don't know if you've watched that. **Lenny Rachitsky** (01:32:47): About the early tech industry. **Farhan Thawar** (01:32:48): Early tech. And I think there was an Andreessen podcast where he said this is the closest thing to what a real startup looks like. So Halt and Catch Fire like an all time recommend, everybody has to watch it. **Lenny Rachitsky** (01:32:59): Do you have a favorite product that you recently discovered that you really love? **Farhan Thawar** (01:33:03): I don't know if I want to be in the zeitgeist right now, but the Meta Ray-Bans are amazing. And the biggest thing about the Meta Ray-Bans was just that I think I never got into it and I saw people around me wearing it, but I only got into it when somebody said I'd never take my AirPods with me anymore. And I was like, oh, I can swap two devices for one device. I always have sunglasses and AirPods because I'll go for a walk or listen to a podcast and now I can just have one device. **Farhan Thawar** (01:33:26): And this happened to me. I was in the summer, I was at a pool party and someone called me and I just took it from my sunglasses and people were confused as where I was taking this call from. But they are the right amount of tech. They're in unintrusive, you can't tell, they don't look like any tech. And then also I was playing soccer with my kids. I have three kids. I just turned the video on and I was the goalie and they were taking shots and I was watching them. They had no idea that I was just recording. And it was such a cool moment because I was in playing soccer with them. I wasn't with my phone and I got to get this amazing set of video that I would never would've gotten. So I really liked the Meta Ray-Bans. **Lenny Rachitsky** (01:33:58): We had Boz on the podcast who leads a lot of that work and he's got a to teach us. And I put on Ray-Bans while we were doing the interview just for fun. You could see my setup. Okay, cool. Two more questions. Do you have a favorite life motto that you find useful in work or in life? **Farhan Thawar** (01:34:15): Okay, I do. And it's on a lot of my profile bios, and it is, everything you know is wrong. And the reason I like that one, and people always like, what would you put on a billboard? And people always come back to me and say, that's like they know that as my motto. **Farhan Thawar** (01:34:32): And the reason for that is it's this notion of if all the knowledge you knew was incorrect, could you from first principles build up a view of the world? And that's kind of how I like to think of things is that, anything could be incorrect. Even things that you think are correct, which is why, again, back to the, I like to experiment. I like to look stupid, because I'm always trying shit because I'm like, I don't know if even though you say this is correct, that this is going to work, right. **Farhan Thawar** (01:34:58): Actually, one example, my wife hates this is I have a Tesla and I routinely will switch gears without fully stopping the car, which you cannot do in a regular car, but I'll be in drive and then I'll slow down to drive back up into my driveway and while it's moving I switch it into reverse. **Farhan Thawar** (01:35:14): And you never would know that that's possible except for trying. And sometimes it goes beep beep because you're going too fast. And she hates it. But I'm always trying weird things and so that's why I say everything you know is wrong. Who knows what's possible, just try different things. **Lenny Rachitsky** (01:35:29): I do the same thing with my Tesla. I used to do it with a non-electric car and my wife is always like, don't do that. Screwing it up. **Farhan Thawar** (01:35:34): Yes, exactly. **Lenny Rachitsky** (01:35:35): I love that on an electric car, there's no gear you're breaking, it's just software. **Farhan Thawar** (01:35:39): Exactly. **Lenny Rachitsky** (01:35:41): This quote reminds me of that you shared of everything you know is wrong. The founders of Airbnb always talked about just this point that everything around you was designed somebody, another human. There's not necessarily that much smarter or insightful. It doesn't mean what they did was correct. Somebody else find some better potentially... **Farhan Thawar** (01:35:57): I think Steve Jobs had a similar thing like, hey, you can design anything. Everything's designed by people. I love that one too. **Lenny Rachitsky** (01:36:03): Yeah. Final question. So you told me the story of this PhD you hired versus just a guy you met in a college, sorry, in a coffee shop. I read another similar story where you hired a waitress. **Farhan Thawar** (01:36:14): Yes. **Lenny Rachitsky** (01:36:14): Is that real? Okay, tell that story. **Farhan Thawar** (01:36:17): Yeah, so again, this is another long list of reasons my wife is in annoyed with me, but this is another one of them. Whenever we are out, I'm always scanning and I'm always scanning people and one, do I know anybody around, whatever. I like to scan for people and I have a good memory for faces. But in this case we were at a restaurant and I saw a waitress doing a very, very good job, an extremely, like she was running between different tables, she was smiling her face, taking everyone's order, making sure that there was a thing happening in the kitchen. She was kind of doing a phenomenal job of organizing the entire crazy busy restaurant. And so in talking to her, I said, what do you do outside of this because you look like you're super. She's like, what do you mean? I'm just the waitress. **Farhan Thawar** (01:36:59): And I said, well, would you like to, this is XtremeLabs. I Said, would you like to work at XtremeLabs? She's like, what's that? So I explained it to her and I got her contact info. She came into the office and she first started off as our receptionist, so she moved from the retail world into the office world, and then I brought her on as my admin and she became one of my recruiters. And I taught her how to recruit and talked to people and she came in with me to info sessions. And over time we actually hired many more people from the restaurant that were really, really good at their job. And what was amazing was, one, she was organized but not reorganized. I had to teach her at Google Docs and G Suite and everything else, but she was super smart but just never had the opportunity. **Farhan Thawar** (01:37:35): The coolest thing about this is that she ended up being, she ended up taking over one of the HR functions for us. And she had a college degree and because of the work she had done with us, she was able to parlay that into finishing, doing one more year and getting a university degree. And now she's a director of HR at a company, which is amazing from, like, she went from that environment to this environment and a lot of her people, she pulled the smart and intense people she pulled from that environment also ended up on these amazing career paths. If I see someone doing a good job, I'm like, what do they do? How can I work with them? This is one example of pulling somebody out of that environment. I have lots of other ones where I overhear someone in their designer or an engineer and I try to hire them into my company as well. **Lenny Rachitsky** (01:38:22): Wow. That is such a good story. I love that. Maybe restaurants are the new feeder system for tech companies. Did not think about that. **Farhan Thawar** (01:38:31): Yeah, I mean, everyone's smart at something, so I was trying to figure out, she was really good at this thing. She'd be so good at something else. **Lenny Rachitsky** (01:38:36): Amazing. I feel like there's so many stories, more stories to tell, but we're going to wrap it up and let you go, farhan. Two final questions. Where can folks find you a line if they want to reach out, learn more, maybe apply to work at Shopify and how can listeners be useful to you? **Farhan Thawar** (01:38:50): Sure, so Twitter's probably the place I try to hang out the most, X at FNThawar, and maybe I'll put that in the show notes. And then listeners for me. I mean, I love to be challenged. I'm sure that there are people who are like, they heard something that I said and they're like, oh, that's super dumb. We do this instead. Or here's research that says that that won't work. I would love to hear more about these because I'm just again, on a learning journey and if I did something stupid, very likely I would like to learn a better way to do things. So I would love for people to comment and say, hey, this is dumb. You should try this, or, that doesn't make any sense. I would love to learn more. So that's what I'm looking for. **Lenny Rachitsky** (01:39:25): All right, well leave a comment in YouTube or on the Substack post with what Farhan got wrong. **Farhan Thawar** (01:39:31): Amazing. **Lenny Rachitsky** (01:39:33): Thank you so much for being here. Thanks for having me. Bye everyone. **Lenny Rachitsky** (01:39:38): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [16/17] Behind the founder: Marc Benioff **Lenny Rachitsky** (00:00:00): I want to zoom back to the beginning of Salesforce. One of the most legendary launch events in startup history. Just looking back at that, any lessons from what you did right to get people to pay attention? **Marc Benioff** (00:00:09): I'm throwing everything against the wall. I'm looking at what's going to stick. I am looking to try to find the winning tactic and turn it into a winning strategy. **Lenny Rachitsky** (00:00:17): Your stock is at an all-time high. I'm curious just what you believe is most contributed to you being able to stay on top and continue to grow. **Marc Benioff** (00:00:24): I actually never look at the stock. I find the stock to be very distracting. The stock isn't the goal. That's not why we're doing this. **Lenny Rachitsky** (00:00:30): AI is the defining technology of our lifetime and probably any lifetime. When was the moment for you where you started to realize this? **Marc Benioff** (00:00:38): I keep having these existential freakout moments about AI. This is really moving fast. **Lenny Rachitsky** (00:00:44): As a founder, you're just like, "Goddamn, I just got used to AI, and everyone is wanting to work on AI in my company. Now, we got to freaking figure out agents?" **Marc Benioff** (00:00:50): No, no, no, no, no. That's a mistake. You want the mindset of, "Oh, the next thing is coming. I can't wait for the next thing." **Lenny Rachitsky** (00:01:01): Today, my guest is Marc Benioff. He's co-founder and CEO of Salesforce, which is the second largest B2B SaaS company in the world worth around $350 billion at the time of this recording, making $35 billion a year in revenue, and 25 years later, is still growing like crazy and dominating the market. In our conversation, we talk about leadership, AI, domain names, beginner's mind, marketing, product, sales, the hardest moment in Marc's journey of building Salesforce. Also, what exactly is an agent and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Marc Benioff. **Lenny Rachitsky** (00:01:49): This episode is brought to you by Cloudinary, the foundational technology for all images and video on the internet. Trusted by over 2 million developers and many of the world's leading brands, Cloudinary is the API-first image and video management platform built for product leaders who rely on visual storytelling to express their unique product value, who are building engaging web and app experiences, and who understand that harnessing the power of AI to automate is the only way forward. **Lenny Rachitsky** (00:02:19): Gil Grossman, Engineering Team Lead at Fiverr, says that our users share billions of images, video, and audio files. Cloudinary's ability to automate our post-production work at scale amounts to a savings of up to 92,000 work days per month. Think bold, build big, ship fast. Let Cloudinary handle your media needs. Start your free plan today at cloudinary.com/lenny. **Lenny Rachitsky** (00:02:44): This episode is brought to you by Enterpret, interpret, unifies all your customer interactions from Gong calls to Zendesk tickets to Twitter threads to App Store reviews and makes it available for analysis. It's trusted by leading product orgs like Canva, Notion, Loom, Linear, Monday.com, and Strava to bring the voice of the customer into the product development process, helping you build best-in-class products faster. **Lenny Rachitsky** (00:03:07): What makes Enterpret special is its ability to build and update customer-specific AI models that provide the most granular and accurate insights into your business, connect customer insights to revenue and operational data in your CRM or data warehouse to map the business impact of each customer need and prioritize confidently, and empower your entire team to easily take action on use cases like win-loss analysis, critical bug detection, and identifying drivers of churn with Enterpret's AI system wisdom. Looking to automate your feedback loops and prioritize your roadmap with confidence like Notion, Canva, and Linear? Visit E-N-T-E-R-P-R-E-T.com/lenny to connect with the team and to get two free months when you sign up for an annual plan. This is a limited-time offer. That's enterpret.com/lenny. **Lenny Rachitsky** (00:03:57): Marc, thank you so much for being here. Welcome to the podcast. **Marc Benioff** (00:04:00): Excited to finally get connected with you and excited to do this podcast with you too. **Lenny Rachitsky** (00:04:04): I'm even more excited, and I actually want to start with something that I think most people don't know about you, but to me, it's almost like a microcosm of how far ahead you look and almost how... basically, how visionary you are, and that's that you've owned a number of epic domain names. For example, bill.com, you.com- **Marc Benioff** (00:04:26): You. **Lenny Rachitsky** (00:04:26): ... code.com, appstore.com. First of all, are there others I don't know about? **Marc Benioff** (00:04:28): There's a lot. **Lenny Rachitsky** (00:04:29): Okay. **Marc Benioff** (00:04:30): Salesforce.com. **Lenny Rachitsky** (00:04:30): Salesforce.com. **Marc Benioff** (00:04:32): That all came from... I'll tell you. It's a good story actually because what happened was I was working at Oracle for 10 years from 1986, and 1996 rolled around like it was a snap of the fingers. All of a sudden, I realized, "Whoa, what has just happened to the last decade?" The decade just flew by. It was crazy. It was a big moment for me in my career, and I had a... It was a huge acceleration. I went from being a kid right out of college to working for Larry Ellison. But after 10 years, I was pretty trashed, and so I said to Larry, "Hey, I need to go and take some time off." **Marc Benioff** (00:05:13): So I went to Hawaii and rented a little house on the beach. I had done some angel investing, and it was a cool moment where some of my companies started to go public, including Siebel Systems and others, and Saba Software, and people I had met at Oracle like Tom Siebel and Bobby Yazdani. Then, I was just fascinated at that point with the internet. I had been working on it at Oracle for a couple years, so I started buying a bunch of domain names of companies that I thought companies. They weren't companies yet. Now, they are companies. But ideas that I thought the names would be great companies one day and reflected where I thought things were going. Yeah. It's a long time ago now. It's a really long, long time ago. I think almost 30 years. **Lenny Rachitsky** (00:06:00): So one of the domain names you owned was appstore.com, which I know you gifted to Steve Jobs, I read in your book. Is there a story there that you could share because that's an epic domain just to gift? **Marc Benioff** (00:06:09): It's a great story, but it's really a story about my relationship with Steve Jobs. When I was in college in 1984, I had the opportunity to be an intern at Apple. I wrote the first native assembly language on the Macintosh. It's a crazy thing to be able to say, but it's true that I was writing these example programs for this Macintosh 68000 Development System on these Apple headquarter buildings in Bandley, Bandley Road in Cupertino and started to have a relationship with Steve Jobs in that... Not that I was actually talking to him. I was like this snot-nosed 19-year-old kid, but he's running around the building. We have this refrigerator over here with all these fruit juices. There's a masseuse over here doing shots and massages. There's a motorcycle in the lobby. There's a pirate flag on the roof, and there's Steve Jobs running around, yelling at everybody, and it was freaking cool. **Marc Benioff** (00:07:10): Okay. So you can just imagine like you're like, "Whoa, this is like I'm in a movie." There's a lot of other cool parts of a movie too that were going on, and it started my relationship with him, and then I actually got to know him then as I eventually got to Oracle. Then, eventually, I started Salesforce, and I had this moment at Salesforce. It was, I think, 2000, 2001. I cannot remember exactly what it was, and we were at the opening of one of his movies for Pixar, and we're having dinner. There's a lot of details around the dinner. It'll be a hugely long story if I go forever. **Marc Benioff** (00:07:56): He says to me, "Well, Marc, now, listen to me. You're doing so great. You've got your company, Salesforce. If you need any help, you make sure you call me, okay?" I'm like, "Yes, sir. I will do that." He took out his... He had just introduced the iPod, and he's like, "I got a thousand songs in my pocket here. Look at this, and that, and all that." It's this cool device. I'm like, "That's such a cool screen. Steve." He goes, "Oh, thanks so much." I go, "Steve, you could do movies on there too, not just... or photos. You didn't have to do songs." "No, Marc. I will never do a device like that. Absolutely not." **Marc Benioff** (00:08:34): That's a little insight into his personality that he would never ever exactly say, "Oh, yeah, I'm going to do the movie device that have the photo, the phone, the this." So, anyway. Things were moving along at Salesforce, and so I was like, "I'm stuck, and I need to get through my block, writer's block, entrepreneur's block. I'm going to reach out to him." He's like, "Come down here right away." **Marc Benioff** (00:09:03): So, literally, I got in my car, brought a few of my team with me, and we go down, and he's like, "Oh, yeah. Oh, yeah, you're blocked. There's three things you need to do right now." I'm like, "Okay. What are they?" He go, "Your company, it better get 10 times larger than it is now in 24 months or it's over." "Oh, okay. Yes, sir. Yes, sir." "Number two, you better sign a huge customer for this Salesforce automation product like Avon. They're a great salesforce." The CEO of Avon was on his board at the time, so that was on his mind. "And one last thing I'm going to tell you you must do." I'm like, "Yes, sir. What is it?" "You better go build an application economy." "An application economy?" "Yes." "What does that mean?" "I don't know, but you're going to go figure it out." **Marc Benioff** (00:09:55): It was like meeting with your guru and getting a Zencon or something where you're... Now, you have a puzzle I have to solve. I literally went away, and I had all the notes from the meeting. I went through it over and over again. Then, finally, I'm like, "I think he wants me to build an app store." At that moment, I went to the domain registry, and I bought appstore.com. Then, I started working on it at Salesforce so that we would have the ability with our platform to build apps, and then sell them, and that you could do all these things. **Marc Benioff** (00:10:34): So I did all that and launched AppExchange in 2005 or 2006. We didn't call it App Store because when we tested the App Store name in focus groups, customers are like, "This is not an app store. This is an app exchange. We're all going to exchange apps and capabilities with each other." Anyway, it rolled out, iPhone rolled out, and then he basically said to me one day, "Hey, come down and see me." This is maybe a year after iPhone. I'm like, "I'll be right down." **Marc Benioff** (00:11:08): I get down there, and I have some team members with me. They'd heard this story before, et cetera, and then we're sitting there like this in the Apple Auditorium. It's not like in a hotel or anything. I remember it very clearly like it was yesterday. He said, "I brought you all down here today." It's very good theatrical performance. I could never do what he does. It's incredible. He's got the thing, and then he says, "And I'm here to reveal to you the App Store." All of our people go, "Huh." They're doing break breath, and they're all like... go white because they're like, "Oh, Marc has been talking about App Store for years. How could Steve even..." **Marc Benioff** (00:11:51): Then, at the end of it... It's all over. Everyone leaves the auditorium. They're all going out to play with the App Store and all these things. I walked down. He's sitting down there by himself working on something. He's in the corner of the stage. I go, "Hey, Steve. Can I talk to you for a second?" He goes, "Of course." Very generous with me. Very kind with me. I go, "Steve, I'm going to give you a gift." "Wow, but Marc, what are you are going to give me?" "Steve, I'm going to give you something you don't have, but maybe you'll need, which is the appstore.com URL, appstore.com, and the trademark for App Store because after that meeting we had six years ago, I ended up trademarking these things and buying this URL." He's like, "Oh, it's very nice, but you know this App Store thing isn't going to be very big. Whatever, but thank you very much." That was the story of App Store. It's amazing. It was a very amazing relationship that I had with him. Very grateful to have that relationship and dramatically influenced me in my career and my whole life. **Lenny Rachitsky** (00:12:59): There's one thread that I love about everything you shared. Here is how generosity was at the center of so much of this, him helping you, you helping him, just wanting to help each other. **Marc Benioff** (00:13:08): He is a very generous person, and I'll tell you that he never turned down anything that I asked him to do. I have so many stories, but one story was I was thinking about buying this house, and I wasn't sure should I buy this house, Should I not buy this house, whatever, and so he went... He said, "I'll go look at it for you." So he went, he is looking at this house, and then he calls me, and he goes, "Well, I don't know if you should do this or that, but this might be good. Maybe it is good. Maybe it is a good idea." **Marc Benioff** (00:13:41): Then, I'm emailing with him after that, and he's very sick, and it's all very sad. Then, he sends me an email, and the last email he sent to me was he said... I said, "Wow. Well, this has worked out better than I thought." He goes, "Marc, everything has worked out so much better than we could have ever imagined." It was just a beautiful thought and incredibly sad all at the same moment, and that was my last correspondence with him. **Lenny Rachitsky** (00:14:14): I feel like we could do Steve Jobs stories all day. **Marc Benioff** (00:14:16): Yeah. Oh, no, I have hours. **Lenny Rachitsky** (00:14:19): Yes, you can. **Marc Benioff** (00:14:20): I have a lot of Steve Jobs stories, but- **Lenny Rachitsky** (00:14:21): Oh, man. **Marc Benioff** (00:14:22): Yeah. Anyway, those are a couple of them. **Lenny Rachitsky** (00:14:24): By the way, I also love that he had B2B SaaS advice here like, "You need a big customer. You need to hire ACVs, build the marketplace." **Marc Benioff** (00:14:30): Oh, he hated those. He hated SaaS, and he hated that I was doing enterprise software. **Lenny Rachitsky** (00:14:31): Yeah, he did. **Marc Benioff** (00:14:35): He's trying to talk me out of being an enterprise software executive. He's like, "Now, Marc, what are you going to do? You're going to go home and tell your kids that you're working on enterprise software? Who do you sell to, CIOs? Have you had met them? How can you be doing this? I can't imagine a more horrible career." I'm like, "I love it, Steve." "No, Marc, you cannot love this. This is not great." It was really a funny thing. He really disliked that, but yet, he was incredibly supportive of me. He would call me all the time. It was really amazing, actually. **Lenny Rachitsky** (00:15:06): Yeah. It feels like a place he was wrong in the end here, which is cool, cool to know. I want to go in a different direction. **Marc Benioff** (00:15:12): He was rarely wrong, by the way, so. **Lenny Rachitsky** (00:15:14): He was rarely wrong with B2B SaaS. $350 billion of value. Who would've known it existed? Speaking of that, so I want to zoom back to the beginning of Salesforce and when you launched Salesforce. It's crazy to think back to that when basically, you were trying to convince people the future of software was not desktop software, it was going to be in the cloud, it was SaaS. You had all these end of software logos. You had mascots walking around with this no software thing. You hired fake protesters at... I think it was Siebel's conference. It was very hard. **Marc Benioff** (00:15:44): I think you read one of my books, Lenny. **Lenny Rachitsky** (00:15:46): I know the history of a lot of these things. **Marc Benioff** (00:15:48): Oh, okay. **Lenny Rachitsky** (00:15:49): It's one of the most legendary launch events in startup history, so I've heard of it many times at this point. **Marc Benioff** (00:15:54): It was a crazy moment. I mean, Siebel, who was really the enterprise software company doing CRM, was doing a user conference. I was looking for an opportunity to launch our product, so we hired a bunch of actors. They were doing this event in San Francisco, and San Francisco is very woke, so people expect a good protest. So we got some picket signs at Home Depot and made some signs that said, "The end of software is near," and all kinds of other... "No software," and all these things. We had a lot of funny things on signs. We were running a protest outside of Siebel that they were in the software business, but we were like, "Oh, no, we've got to get out of software. We've got to create the end of software." So we have picketers outside of the streets. **Marc Benioff** (00:16:50): Anyway, he comes out himself out of the building and really gets super upset. Right then, we hit a button, and we have other actors in a van who come out, and they are staging themselves as news crew. So they are like KNMS, K No More Software, and we're like... They're interviewing the protesters. So now he thinks that it's a media thing. He calls the police. He got very upset. He's a great guy. By the way, I love Tom Siebel. I think he's also one of the great entrepreneurs of our generation. He's just fuming, and he doesn't know what's going on. He doesn't exactly know it's us, and we're just having the best time. That night, we had our huge launch event at one of the top theaters in San Francisco. We hired a great band, and it was really... We just had so much fun. It was just a really great time. That was all happened. I remember very well. It was February 22nd of 2001 or 2000, 2000, February 22nd, 2000. **Lenny Rachitsky** (00:18:06): I love this. I haven't heard that interview, the reporter part of that story before. **Marc Benioff** (00:18:10): It was crazy. **Lenny Rachitsky** (00:18:12): I love it, and it sounds frivolous potentially, but I think the genius of this that I want to touch on is- **Marc Benioff** (00:18:18): "Frivolous" is a good word. It probably was frivolous. **Lenny Rachitsky** (00:18:21): So what I imagine is you're trying to get people to even know Salesforce exists, to differentiate, to get the name out, and I feel like that's something a lot of founders struggle with. They don't really know how to get their name out, how to get people to pay attention. Just looking back at that success, I guess, just any lessons from what you did right to get the word "Salesforce" out to get people to pay attention at all to what you were doing? **Marc Benioff** (00:18:42): Well, it's a noisy world, Lenny, and you can see that. You can get on Twitter. It's like... I mean, there's a lot of noise, and how do you break through? We have that challenge today. We're introducing a huge new product called Agentforce. I've only been working on it for a couple months now. I introduced it at our Dreamforce Conference, and that was one way to break through, which was I took our conference and said, "It's just going to be about Agentforce." I'm trying to think about, "What are all the things I need to do to get my company 100% on Agentforce, my customers, everyone?" because I know I have a window of opportunity here. **Marc Benioff** (00:19:25): We're first, we're ahead. We have hundreds of customers on this now. We're on it, which is amazing. We've moved our whole help infrastructure to Agentforce. We're seeing incredible results. We've cut our human escalation from our support infrastructure down by 50%. We're resolving 83% of all of our inquiries robotically. It's incredible. So, now, how do I get that message out? How do I do it globally? How do I find my KNMS moment where I can come up with something that's viral and exciting? **Marc Benioff** (00:20:04): I'm trying lots of different things. I have Matthew McConaughey and Woody Harrelson who are two friends of mine helping me. So they said, "We'll cut ads for you." They have not been together in an ad ever, and they haven't done anything together since True Detective. They're friends of mine. Again, very generous people to agree to do this. We've shot three ads so far. I put them out on Twitter to get feedback from folks. Is this a good idea? **Marc Benioff** (00:20:35): I am running this help.salesforce.com to show what we can do with it. Is that a good idea? I'm training all my salespeople in how to sell it. Is that a good idea? I'm running aggressive marketing against Microsoft because they have really a terrible product, Copilot, that I have to position against and market against. Is that a good idea? Should I be marketing and positioning against them? **Marc Benioff** (00:20:58): I'm trying lots of things, and what I'm trying to do, Lenny, is what I recommend to all entrepreneurs. The message is really in the medium here, which is that I am looking to try to find the winning tactic and turn it into a winning strategy. I don't know actually which one of those things is going to be the most important thing in launching this product, so I'm trying a lot of things with that old expression. I'm throwing everything against the wall. I'm looking at what's going to stick. Then, once I find that thing, I will then grow that as my strategy, and that is what I'm trying to do. **Marc Benioff** (00:21:33): I'm even expanding my distribution organization. I'm trying to hire an additional one to 2,000 account executives just to focus on Agentforce. So I'm trying to do everything I can to get that light switch to go on where I can show customers this is an incredible opportunity to lower your cost, to make things better, and to show that for the first time, we can have digital labor, that Salesforce isn't just managing your data, but we're a digital labor provider. So this is that moment. **Lenny Rachitsky** (00:22:03): There's so much there that I love, this idea of trying a bunch of things, looking for the tactic that becomes your strategy. It feels like also there's this focus of just go all in and focus on this one thing, and then try a bunch of different ways for this one thing that you're focused on to win. There's also an element of... I just had Seth Godin on the podcast, and one of his big lessons is be remarkable. Create something people remark about. So this celeb-oriented ad that you're working on, I think, is a really good example of that. **Marc Benioff** (00:22:31): Well, that is a key thought though that he's saying, which is you got to find it, but finding that is the hard part, so you got to be like... One of my friends is Chris Rock, the comedian. So what he'll do is he just doesn't go out and do a Netflix special with all of his jokes. He's out there testing his jokes in clubs and doing all kinds of crazy things. I won't go through all the crazy stuff he does to test his jokes, but by the time it gets to the big Netflix special, he knows what works and what doesn't work. So that is something that we all have to do as entrepreneurs. We need to be testing lots of things. We need a lot of experimentation, and we can't be too arrogant. **Marc Benioff** (00:23:15): I think another thing that's extremely important is... I have a pretty deep meditation practice for three, four decades which is we have to be cultivating our beginner's mind. We have to use our mindfulness in a way to clear everything out and then get back to, "What is my beginner's mind?" In the beginner's mind, I have every possibility, but in the expert's mind, I have few, and in some cases, maybe none. So I've been doing this a long time. I've been writing software since I'm 15. I'm now 60. That's 45 years. I don't want to have an expert's mind. I want to have a beginner's mind, and how do I have that beginner's mind? Because those ideas will come at me if I can go, "What could work?" rather than saying, "Oh, I know what is going to work," or, "This is the one thing that is going to definitely work," or, "We have to do this." **Marc Benioff** (00:24:10): As soon as you start using words like that, you know that you're going to completely implode and fail. You have to say, "Here, we have to do all these things." Like in my company right now, we just did this all-hands call. I was like, "There's six things I really want to get done," but one thing is I didn't get everybody focused on Agentforce and really watch the energy. Number two is I need to find more fuel in the company to fuel this idea because this is clearly a breakthrough product, so how do I get everyone focused on it? Number three, where I think it's really important, we need more distribution capability. We don't sell through franchises. We're not selling through dealers, resellers. We sell direct, so I know I need more account executives. **Marc Benioff** (00:24:56): Number four is I need to be telling lots of customer stories. So, number one, customer zero, me, and number two is I need to tell you all the stories. Like, you can see the story of Disney. I'm doing a huge amount of AI work for them and Agentforce work. Let me tell you the story about Disney. I need to tell you that story, and then we have this whole ecosystem of people around the company called Trailblazers, millions of them, who know our platform. They all have to become agentblazers. **Marc Benioff** (00:25:23): The last thing is I just shipped the product into all 135,000 Salesforce customers. So it's their nascent, and they need to flick it on. I need to motivate them to turn it on. These are the six things I'm thinking about all the time. So it's not just one thing. I'm trying to figure out what it is, and I need a beginner's mind to assess how do I move forward, how do I evolve, how do I inspire, how do I motivate, how do I energize. **Lenny Rachitsky** (00:25:51): This episode is brought to you by Coda. I use Coda every day to coordinate my podcasting and newsletter workflows from collecting questions for guests to storing all my research to managing my newsletter content calendar. Coda is my go-to app and has been for years. Coda combines the best of documents, spreadsheets, and apps to help me get more done, and Coda can help your team to stay aligned and ship faster by managing your planning cycle in just one location, set and measure OKRs with full visibility across teams and stakeholders, map dependencies, create progress visualizations, and identify risk areas. **Lenny Rachitsky** (00:26:26): You can also access hundreds of pressure test templates for everything from roadmap strategy to final decision-making frameworks. See for yourself why companies like DoorDash, Figma, and Qualtrics run on Coda. Take advantage of this special limited time offer just for startups. Head over to coda.io/lenny and sign up to get six free months of the team plan. That's coda.io/lenny to sign up and get six months of the team plan. Coda.io/lenny. **Lenny Rachitsky** (00:26:57): I love this idea of beginner's mind. I imagine it's very difficult to operationalize, especially for a company at 25 years old at this point. Obviously, you meditate. You put a lot of effort and focus into building this. It's hard to do that within a company. Is there anything you do with meetings, with leadership, with the way you operate that spreads this way of thinking within the org? **Marc Benioff** (00:27:18): Well, Salesforce is now the second largest software company in the world, but also the second largest software company in Japan, and that's a country where I put a lot of time and energy into. I love going there. I love going to Kyoto. When I go to Kyoto, I like to go to some of these amazing Zen temples. By the way, that's one of the things that Steve Jobs love to do, and he used to go to these great sushi restaurants. There's a great one in Kyoto named Sushiiwa. If you go in there, you'll see he's signed something for them. It says, "All good things. Steve Jobs." I said, "What did he do over here?" He would go to this great sushi restaurant, and then he would go to Ryōan-ji, the Rock Garden Temple. Incredible metaphysical temple. **Marc Benioff** (00:28:04): I've gone there. I've gone there for decades. I've brought a lot of friends of mine there. Yeah. You got to clear your mind and let it come in. You got to receive it. You need to listen. I remember I even brought Neil Young there, the musician. He's one of my favorite people in the world, and obviously, I love his music. His soundtrack is the soundtrack of my entire life. We were sitting there, and he was so deep in meditation, and then he started walking around. The temple was closing, and then he was in the zone, and I didn't want to bother him, but I'm like, "You know, I think we got to go." **Marc Benioff** (00:28:38): Anyway, it turned out he had written a whole album while we were there in his head, and he was basically transcribing it all. This incredible creative process. Look, we're all writing an album in our head. What album are you writing? What music are you writing? How are you getting into that zone yourself? You want to be a great entrepreneur. You want to be a great CEO. You got to clear your mind, and you got to be ready to write that music. **Marc Benioff** (00:29:06): That music could be your business plan, your product plan, your product launch plan like we're talking about for my Agentforce product. That's what we're all trying to do, and I use a place like Kyoto as a place to do that also because geography is important. Where you are matters. I know you're in Marin, so Marin County. Maybe you can go out to the top of Mount Tam. Maybe you go to Spirit Rock with Jack Kornfield and go clear your mind there, but you got to find the place to do that and create the location. It may not be in the office. It may be somewhere else. **Lenny Rachitsky** (00:29:41): By the way, you have the most amazing friends list. All these folks you mentioned, I've met. **Marc Benioff** (00:29:41): Okay. **Lenny Rachitsky** (00:29:49): I don't know how long this goes. [inaudible 00:29:49]. **Marc Benioff** (00:29:48): They are cool. I am lucky that I've met a lot of cool people. Yeah. I don't know how I got so lucky to meet some of these people. **Lenny Rachitsky** (00:29:53): I want to zoom out a little bit and talk about... Every month or so, I hear about a startup, I do a bunch of angel investing, that's trying to basically disrupt Salesforce, come after Salesforce. They bash your... don't kill me for saying this, your user experience. They're like, "Oh, so complicated. It's been around three to five years." **Marc Benioff** (00:30:11): We are too complicated. I agree. **Lenny Rachitsky** (00:30:12): Okay. I'm curious just what you believe is most contributed to you being able to stay on top and continue to grow. We're recording this today, and your stock is at an all-time high basically even now. **Marc Benioff** (00:30:25): Wow, I didn't even know that. **Lenny Rachitsky** (00:30:27): Roughly. **Marc Benioff** (00:30:29): I actually never look at the stock. **Lenny Rachitsky** (00:30:29): Okay. **Marc Benioff** (00:30:31): I find the stock to be very distracting, and I encourage my employees also don't look at the stock because the stock is just a reflection. Money isn't the goal, right? The stock isn't the goal. It's coming at the end of the journey. It's like that's not why we're doing this. The journey is the reward. That's also something Steve Jobs would say all the time. Another bow to Steve Jobs here. I think that this is really important, and I look at myself as a startup. **Marc Benioff** (00:31:05): I am a startup CEO. I'm a startup entrepreneur. I'm still at the beginning of Salesforce. No matter what I'm doing at Salesforce, whether I'm the CEO, I'm sometimes the chair of the board. Like, last week, we had a board meeting. Sometimes I'm a product manager. This is a startup, and we're a 25-year-old, 75,000-person, $38 billion, $300 something billion market cap startup, but we're a startup nonetheless. We have some great products, but we are just starting. As an example, Lenny, we are just starting the digital labor industry, and we have a product called Agentforce, and we are just starting. We are just at the beginning. **Lenny Rachitsky** (00:31:47): I want to bounce around a little bit, but let's talk about Agentforce. I know this is, as you've said, the thing you're most focused on right now. It's a big bet you all are taking. When people hear this word "agent," I think a lot of people are embarrassed to even ask like, "What does that even look like? What is an agent beyond what LLMs are today?" Is there an example you could give of something you've seen that maybe blew your mind of what an agent can do? **Marc Benioff** (00:32:09): Yeah. I saw it in the movies. I saw it in Minority Report, which was a movie that was co-written by our futurist, Peter Schwartz. Tom Cruise runs into the Gap store, and all of a sudden, it says, "Hey. Hey, Tom. Have you thought about this new shirt? Look at these jeans. You bought this last time. Now, you could try this. You could try that. What about this? What about that?" It knew his history. It understood him. It knew what was going on. This is 20 years ago. This whole store changes digitally to reflect his interest, his ideas, and it's starting to talk to him and work with him. **Marc Benioff** (00:32:51): That is an agent. It isn't just the agent that we saw in the Matrix, Mr. Smith, or whatever it is. It's someone that's working with you, someone. That's an interesting, for you, slip. It's something that is working with you. It could be your piece of software in your phone. It could be a robot that's going to be in your home. It could be your car that knows you, understands your preferences, has an institutional memory of you, and now is helping to advise you. **Marc Benioff** (00:33:22): I'll give you an example that I'm going to... I go into UCSF all the time. I'm actually just getting through an Achilles rupture right now, so I've had a lot of interactions, and the hospital... or you're getting your healthcare, getting your labs done, getting your physical done, getting your scans done, whatever it is. There's always these pre-operative and post-operative or pre-procedure and post-procedure things, and you're getting these phone calls. Every time I get a phone call, I'm like, "Ugh, that probably just cost them a hundred bucks, and we probably could do that a lot cheaper and a lot easier with an agent." **Marc Benioff** (00:33:58): Then, when I talk to my doctors and nurses at UCSF, they're all burnt out post-pandemic because they're scheduling pajama time to go through all their digital messages at night. It's like a lot of this could be done a lot easier with agents and AI, and we're going to make their lives a lot better, a lot easier, simpler. Some of those things that they're doing, they don't need to talk to me about what my cholesterol number is because I got my labs, and the cholesterol number is this number or that number. A lot of this can be done with technology, and then save the parts that are important for them like when I come to see them or I want to have a real, deeper, more empathetic conversation face-to-face with a deeply experienced doctor. That's a whole another opportunity for me. **Marc Benioff** (00:34:45): That is an agent or the agent is like... Here's an example. I had a CT scan, and you have to drink this contrast, and then all of a sudden, the... drink it, but they give it to you through an IV, and then they're taking better pictures. But then, you have to drink water to flush the contrast out of your body. Do you think anyone called me and said, "Hey, did you drink the water?" No, nobody calls me to drink the water. You have to remember. You're on your own in healthcare in the US. So the agent is going to call you and say, "Hey, did you drink the water? Did you take your meds? Do you need to have a repeat lab? Do you need to go see your doctor again?" So the agent is going to be there by your side. So that's an healthcare example. There's a lot of examples that we can probably have. **Lenny Rachitsky** (00:35:25): There's just a story in The New York Times which isn't about agents specifically. It was about comparing ChatGPT to a doctor where they tested a doctor's ability to diagnose versus a ChatGPT directly or a doctor plus ChatGPT. By far, the best was just ChatGPT, removing the doctor from the equation. **Marc Benioff** (00:35:43): Yeah. They wrote up a clinical study where they actually did look at, in a semi-peer-reviewed way, that ChatGPT, in many cases, was giving more accurate diagnoses than a doctor because the doctor had a more bias coming in working with the patient. So that's super interesting and I think something that we should probably all look at that study and think about that. **Lenny Rachitsky** (00:36:09): Speaking of The New York Times, there's actually this quote I found. You did this op-ed talking about AI. So the quote is, "Throughout my career in Silicon Valley, I've witnessed numerous waves of innovation, but none compared to the profound impact of AI. AI is the defining technology of our lifetime and probably any lifetime." When was the moment for you where you started to realize this where it's like, "Oh shit, this is not just another cool toy?" **Marc Benioff** (00:36:33): Well, I keep having these existential freakout moments about AI, and it's happened over a series of decades. But for those of us who grew up with these movies like WarGames and Minority Report or Her or... across the board or read some of these books. One of my favorite books on AI is Ghost Fleet. You think about, "Where are we going with AI? Where are we going with AI?" With Salesforce, I think about our journey, and I've been waiting for this to happen and trying to bring us along, especially in the last decade with the development of our Einstein platform, and now the development of our Agentforce platform. **Marc Benioff** (00:37:18): This week, at Salesforce, we'll probably do about 2 trillion AI transactions. With our total now, Einstein and Agentforce platforms, we're definitely the largest provider of enterprise AI transactions in the world as far as I could tell, and I keep thinking, "Wow, this is going to get more and more intense." One step was we had to automate all these customer touch points. So like wearing my Disney fanboy shirt here, we run the Disney Store and the Disney Guides, and there's Disney Real Estate, and there's the DisneyQuest call center, and there's... Every aspect of Disney. When you're a customer, you're interfacing with Salesforce. So that's what we've loved doing, automating all these customer touch points: sales, service, marketing, analytics, Slack, integrating it all with MuleSoft. That's what we do, and then aggregating it all into a big database where we call it data cloud, and then federating that data cloud to other data sources. So that's the two steps we've been doing, automate the customer touch points, aggregate the data, and then step three is the agentic platform on top of that. **Marc Benioff** (00:38:29): When you think about what's happening now that you can go to help.salesforce.com and have your issues resolved with that on the agentic layer, that's amazing. Then, the fourth layer that will come will be the robotic drone layer where those robots and drones will then feed off of the platform and all of these capabilities. That vision of the future is something that we've all had in the industry for years. It's not my magic vision. This is a vision that's been around. It's been the fundamentals of computer science that we would move from having... We'd go from data to automation, and that is what we're all driving, and we're driving that industry. We're going lower cost, easier to use, and more automated constantly. That's powerful. This is really moving fast. **Lenny Rachitsky** (00:39:21): You mentioned Einstein briefly. I'll also mention my dog is named Einstein, and I got Einstein swag once with the socks, and I love them, so. Also, that's also an example of you bought einstein.com very early. **Marc Benioff** (00:39:33): Yeah. **Lenny Rachitsky** (00:39:34): That was another domain name that you owned. **Marc Benioff** (00:39:36): Well, I just thought Einstein would be a great name to talk about artificial intelligence, and it really has been. There. You can see him behind me right on my shelf, on my bookshelf. I keep him back there. You see Einstein? I think they were [inaudible 00:39:50]. **Lenny Rachitsky** (00:39:36): My view is blocked. **Marc Benioff** (00:39:36): Oh, I'll go grab him. **Lenny Rachitsky** (00:39:52): Totally. Okay. Let's check it out. **Marc Benioff** (00:39:54): There he is. Ugh. **Lenny Rachitsky** (00:39:55): Show and tell Segment in the podcast. **Marc Benioff** (00:39:55): Oh, yeah. **Lenny Rachitsky** (00:39:59): Oh, cute. **Marc Benioff** (00:40:00): Yeah. **Lenny Rachitsky** (00:40:00): That's a big old Einstein. **Marc Benioff** (00:40:02): That's a key part of our vision for Salesforce, our Einstein platform was everything we're doing. We wouldn't get to Agentforce without getting to good old Einstein here. **Lenny Rachitsky** (00:40:12): Very cute. As you talk about all this, I imagine many people are thinking, "Oh shit, we're not going to have as many people working. What are we going to do with our jobs? AI as agents." I know anything you say could be taken way out of context and just like, "Marc Benioff says everyone is not working," but I guess just... I know you've said you're not going to be hiring as many engineers next year. I guess anything there to help people understand how the workforce will change in the future? **Marc Benioff** (00:40:35): Well, I can tell you about my own company and what I'm telling my own employees, which is that, yeah, we're going to have to rebalance some of our workforce because you can see it in the numbers I just gave you which is we need less support engineers because we have a robotic support layer with Agentforce. So that is very real, and we all need to adapt. At the same time, I'm hiring a lot more account executives and folks to grow the company. So I just encouraged everybody on the all-hands call to think about that. **Marc Benioff** (00:41:06): Then, I just gave you the idea of healthcare. The interesting thing about healthcare though is that a lot of the jobs that I think that are going to get created just... we don't have people for, and I think there's a lot of things that we need help with in the world that we don't have people for. So I think a lot of these jobs will not necessarily get replaced, and I think that... I have a home in a small town, and in this small town... It's very much a blue-collar town. Folks are still working in the restaurants, driving trucks, working in the supermarket, and working on their homes, building, construction, gardening. **Marc Benioff** (00:41:56): Look, it's going to be a long time before, I think, jobs in the small town where I have a home will ever get impacted. But in the large town where I have a home, San Francisco, well, then I just gave you an example where I think that jobs will get impacted. So it'll be a tale of two cities, literally, and I think you will see different impacts in different places. **Lenny Rachitsky** (00:42:21): So what I'm hearing there is support people trending down, account executive sales trending up? **Marc Benioff** (00:42:27): Right now, that is Salesforce in a nutshell. **Lenny Rachitsky** (00:42:31): That touches on something I wanted to touch on also which is that you're... A lot of founders today are very product-minded, very product-oriented founders, and they want to build product-first companies, grow product-led, all these things. Salesforce, I think, very publicly, is very sales-led, very marketing-led, not product-led. Obviously, product is a core part of it, and it all works together, and all these things. But I guess just any advice for founders that are very product-oriented and maybe are hesitant to lean into sales, into cust- **Marc Benioff** (00:42:57): Yeah. I would say we're not sales-led. Well, I think let's just use Agentforce as an example, right? **Lenny Rachitsky** (00:43:01): Mm. **Marc Benioff** (00:43:01): So we're running the year, we're running this year. This is our fiscal year 25. Okay? It ends in the end of January next year. Lenny, this is the year of data cloud. This was not supposed to be the year of Agentforce. So it's the year of data cloud. I just gave you the pitch. We've automated all the customer touch points. Now, we're adding the data cloud to all of our customer implementations. We have 135,000 customers. We've implemented data cloud into all of them. They all need to turn it on. Our teams need to show our customers how to build data cloud and how it's going to help our customers have a better data structure. I almost combined "beta" and "data" together. So they need a better data structure, data architectures, data cultures. **Marc Benioff** (00:43:51): Then, we had our breakthrough, and I can tell you the story where all of a sudden, I'm like, "Wow, this agent technology is happening much faster than I thought it was going to, and we are going to market now." By the time we get to Dreamforce, we are going to take this incredible technology. We accelerated it radically because we bought this company called Airkit, which is one of our Ohana... It's a great story. **Marc Benioff** (00:44:18): Great entrepreneur have this company, fantastic company called RelateIQ that we bought many years ago, about 10 years ago, stayed with us for many years, like six or seven years, wanted to leave, and we said, "Great." We gave them the investment to leave, invested in the company through Salesforce Ventures, built this amazing platform, and then we said, "Now, we want to buy it back." Then, he came back about a year ago, and then it just accelerated the agent vision, and then we delivered Agentforce production code at the end of October. So, all of a sudden, now, we are releasing this product. **Marc Benioff** (00:44:56): I think it's very important, if you're an entrepreneur, to realize it's not just about the product. It's not just about sales. It's not just about marketing. It's not just about accounting. It's not just about your investors. It's not just about your employees. It's not just about your stakeholders. It's about everything, so you better be ready to be an orchestra leader. You can't just be playing the clarinet. **Marc Benioff** (00:45:20): I think that's what you're getting to, which is that there's entrepreneurs who are like, "I'm just going to play the clarinet." For those, I don't think they're going to go as far as they could go. You want to be playing the whole symphony, and you want to get everyone running. That symphony is sales, service, marketing, product. Every part of your shareholders, your stakeholders, your customers. You have to be constantly playing the whole symphony, and you have to have a big mind to think about, "Whoa, I have a lot of stakeholders in my company, not just one stakeholder." It's not just about product and technology. If you're going to narrowcast yourself, you're doing a disservice not just to yourself, but to everybody else as well. **Lenny Rachitsky** (00:46:02): Speaking of big mind and beginner's mind, we have a recurring segment on this podcast that I call Fail Corner. Where it comes from is people come on this podcast, they share all these stories of, "Everything is going great. We're killing it. I've had all these successes," and people get discouraged because they hear just people only succeeding when they often fail. So I try to ask guests to share a story, and let me ask you this. Is there a story you could share when it was a big struggle for you when you're struggling when something went super wrong that you worked through and learned something from? **Marc Benioff** (00:46:35): Sure. Well, I'll just give this example. About two years ago, we went through this huge transformation in our company, and there were a lot of crazy things that were happening, but it was a little bit like we're all on this Airplane, and everything is going really well. Then, something seems to be going really wrong, and we look up front, and the two pilots seemed to be missing. Then, the one guy with the parachute jumped out of the plane, and then we're all like, "Whoa, what are we going to do?" We had to do some really crazy and somewhat destructive things at the moment to basically get the regeneration of the company. **Marc Benioff** (00:47:12): One of those things that we did two years ago was we had to architect a layoff, and we had never done a scaled layoff before. We had to lay off 10% of the company to save the company, and I didn't want to do it. I mean, it's the last thing I want to do as an entrepreneur, which is to adjust our headcount, but we were coming out of the pandemic, and we had just hired too many people. **Marc Benioff** (00:47:33): Now, it turned out that a lot of companies in Silicon Valley all did that same maneuver during the pandemic. Things were so robust in the pandemic that we were overhiring. By the time the pandemic was over, we had too many people. I mean, what did I know? It was my first pandemic. All of a sudden, my next pandemic, I'll know that there's an economic cycle associated with it and an inflation cycle too. **Marc Benioff** (00:47:58): So I learned a lot in the pandemic, and now, we're here. Now, all of a sudden, we're architecting two years ago this layoff. Then, when we did the layoff, then I'm trying to overcommunicate. I'm having all employee meetings. It's a complete dumpster fire. It's a nightmare. I'm getting bashed in the press, on Twitter. Everyone is shooting at me. It's like, "Oh, boy." If I had a thick skin, it got a lot thicker during that moment because it's never going to go well no matter what, and it didn't go well but we got through it to the point where you're giving me these accolades, wonderful, on this podcast about where we are today financially and from a structural standpoint or now from product innovation standpoint, but that's not where we were two years ago. **Marc Benioff** (00:48:51): It was clear we had to go through a financial transformation, which included an adjustment of our head count, and we had to go through a technology, and a product, and an innovation transformation. Those two things were going to require us to do a number of things, and they were going to be painful. So we all had to go through some of that pain to get the gain that we have now, and that was not easy. **Marc Benioff** (00:49:17): I was in shock that I was going through this two years ago because I had already been running the company for 23 years. Things were going pretty well. Yes, there were a lot of failures during that period. I just didn't expect another massive issue to hit me. But guess what? There're constantly massive issues coming at you, and there's more coming, and that's the nature. **Marc Benioff** (00:49:39): My friend, Michael Bell, is probably the best entrepreneur I know. He says, "There is no linear success." So what that means is that stock chart that you just referred to, there's no up-and-to-the-right perfect chart where it's just one line. I don't care who you are. Apple doesn't have one. No one has one. Okay? There's going to be changes. It could be economic changes. It could be societal changes. It could be the pandemic. There's no up-and-to-the-right. If you think it's only going to be about up and to the right, you're in the wrong business or you have the wrong life. Right? Hey, the monastic life is maybe more for you where you're just out living in that more of that steady state. Right? But if you want more variation where it's not steady state, the entrepreneurial life is a rock-and-roll roller coaster, and you get ready because it's going to be pounding you all the time. **Lenny Rachitsky** (00:50:33): One of these people that you described that jumped out of the airplane speaking on the roller coaster ride is your co-CEO, Bret Taylor. What's interesting to me is he's also all-in on agents, and what it makes me think about is there's this meme of what did Ilya see when he left and tried to kick out Sam Altman. I'm curious just like what did you guys see about agents being the future that you're both so committed to this? So interesting. **Marc Benioff** (00:50:54): Well, I just think that this idea that agents are one of the most important things that we're all going to work on, and I think everyone is going to go to agents. Look, I just heard about Google today has Agentspace. At first, I was like, "Well, I guess they like the Agentforce name." I love Sundar. He's one of my favorite people in the world. We heard Microsoft now has agents. I read Oracle has agents now. SAP has agents. Everybody's got agents, and good. That's what we want. We don't want to be the only one. **Marc Benioff** (00:51:30): If you're the only one and no one else is working on it, you've got a problem, actually. So you don't want to be the only one. You want to be in a market. You don't want to be one company offering a solution and the only one. You want to be in a competitive market where people are competing with you, and you're selling against somebody else, and you're getting better, and you're moving forward. It's like the automobile industry. One of my favorite people is Akio Toyoda. Toyoda-san was now the Chairman of Toyota, was the CEO of Toyota. His grandfather started Toyota. He says, "Better, better, better. Never best." It's the Japanese motto of Kaizen. **Marc Benioff** (00:52:10): So we talked about Japanese Shoshin, which means beginner's mind. Now, we're learning another Japanese word here, Kaizen. Kaizen is continuous improvement, and you need to be doing continuous improvement. With where we are right now with agents, every software industry is going to move to agents. We have to just like every software industry... Well, at least in CRM or automating customer touchpoints, data and managing data, and building that data infrastructure, agents. It's all related. We're all moving in the same direction. **Lenny Rachitsky** (00:52:47): I'm just thinking as a founder, you're just like, "Goddamn, I just got used to AI, and everyone is wanting to work on AI in my company. Now, we got to freaking figure out agents?" **Marc Benioff** (00:52:54): No, no, no, no, no. That's a mistake. That is the mindset you want. You want that mindset. You want the mindset of, "Oh, the next thing is coming. I can't wait for the next thing." In some ways, you have to be saying, "I can't wait for the next failure. I can't wait for the next success. I can't wait for the next innovation." Oh, well, that's innovation overall, right? **Marc Benioff** (00:53:18): See, we're in an industry where technology is constantly getting lower cost, easier to use, and more automated. So if you're doing for two and a half decades, or four decades, or four and a half decades now that I've been doing it... When I started in this industry, I started on a computer called the TRS-80 Model I with 4K of RAM. I was doing a podcast recently, and they're like, "Well, who did you sell your first piece of software to?" I said, "Well, I sold it to CLOAD Magazine in Goleta, California and- **Lenny Rachitsky** (00:53:54): For $75. **Marc Benioff** (00:53:54): For $75, and they said, "Thank you for..." and then they said, "Oh, that's great, and did you send them the disk?" I'm like, "No, no. There was no disk. CLOAD standard for Cassette Load in BASIC. That was the command in BASIC, C-L-O-A-D, Cassette Load, CLOAD. That was the command. So that was the name of their magazine, and then you would get the cassette every month with five or six things that they had bought from people like me." I mean, they didn't know they were buying it from a 15-year-old kid in high school in Burlingame High School California. But I had written the How to Juggle thing, and they bought it for $75. They sent me the one-page agreement, and I signed it. Then, I told my parents, and they're like, "What? Huh? You're doing what? Oh, okay. That's nice, honey. Great job." **Marc Benioff** (00:54:45): So they didn't understand. Nobody knew. It was crazy. It was like 1979 or 1978, so nobody knew I was selling software. I was in high school. It was just a moment in time, but I need to have that mindset all the way along which is, "What is the next great thing? What is the next great success? What is the next great failure?" You're growing. You're evolving. You're learning from that. That's what you want. You want to have that growth mindset. Right? You want to embrace that. Does it make sense what I said? **Lenny Rachitsky** (00:55:21): Absolutely. **Marc Benioff** (00:55:22): I jumped on that one little thought. "Oh, gee, yeah. I've got this now under control, but now I've got agents, so now, what am I going to..." It's like, "No, that's what you want." By the way, I want what's after that too, and what's after that, and what's after that. That's what's really exciting about the future. It's coming. **Lenny Rachitsky** (00:55:43): Why? **Marc Benioff** (00:55:43): I want to be... One of our customers said this, and people think I said it. It wasn't me. I want to get to the future first and welcome our customers there. That's what I think is... By the way, that's what I think Elon Musk does so well. He is like... I don't know all the crazy things he's doing to see the future. He's clearly doing some unusual things, but then he's like, "Yeah, we're going to have robots in the future, and brain machine interfaces, and driving electric cars. All of these things are going to be happening in the future, and I'm going to have 10 companies that are going to do all of them." Wow. **Lenny Rachitsky** (00:56:23): He's not only thinking about it, he's doing them each. **Marc Benioff** (00:56:26): Amazing, **Lenny Rachitsky** (00:56:27): Amazing. **Marc Benioff** (00:56:27): No one like this. **Lenny Rachitsky** (00:56:29): Yeah. **Marc Benioff** (00:56:29): Never seen anything like it. I don't understand how it is even possible. **Lenny Rachitsky** (00:56:34): Same. Marc, I know you have to run. This was incredible. I think this is a beautiful place to end it. **Marc Benioff** (00:56:40): Oh, Lenny, you're so much fun. I've been looking forward to being on your podcast and talk about entrepreneurship, and thanks for everything you're doing for the industry and for entrepreneurs everywhere. **Lenny Rachitsky** (00:56:49): Same, Marc Benioff. **Marc Benioff** (00:56:50): We're all so grateful to you. Goodbye now, and welcome. **Lenny Rachitsky** (00:56:53): I feel the same. Thank you. Bye. Bye, everyone. **Lenny Rachitsky** (00:56:56): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode. --- ## [17/17] Why great AI products are all about the data | Shaun Clowes (CPO Confluent, ex-Salesforce, Atlassian) **Lenny Rachitsky** (00:00:00): I love that you have very strong opinion about this, which is just the state of the product management career and how most PMs are not that great. **Shaun Clowes** (00:00:08): Why is it that product management is still such a relatively undeveloped discipline? We're like 15 to 20 years into this, and so there's something about the current state of product management that isn't getting at the truly important things, the truly value-added things. If we were doctors, you'd be like, "That's totally unacceptable." **Lenny Rachitsky** (00:00:24): What's the answer, Shaun? How do we solve this problem? **Shaun Clowes** (00:00:26): In everything always talk from the customer's perspective, from the market's perspective, from the competitor's perspective, the very small number of PMs do that. They get dragged into internal politics, they get dragged into scrum management or scrum execution or product delivery, and you just can't win that way. **Lenny Rachitsky** (00:00:40): You kind of have this hot take that the way AI will most impact product management is data management. **Shaun Clowes** (00:00:45): Well, you've got this synthesis machine, which is this LLM thing that's going to help you do synthesis, but if it hasn't got all that data to do synthesis on top of, it's got nothing. And so that means that LLMs can only be as good as the data they are given and how recent that data is. **Lenny Rachitsky** (00:00:58): In the future, if you can easily clone a B2B SaaS app like Salesforce or Atlassian, what happens to these businesses long-term? Do they just become, are they all in trouble? **Shaun Clowes** (00:01:06): People really underestimate where the value is created in these applications and they just kind of get it completely wrong. **Lenny Rachitsky** (00:01:17): Today my guest is Shaun Clowes. Shaun is chief product officer at Confluent. Previously he was chief product officer at MuleSoft, which is a billion-dollar business within Salesforce. Before that, he was chief product officer of Metromile, a public auto insurance technology company. And prior to that he spent six years at Atlassian where he ran the Jira agile and also built the first ever B2B growth team. He also created two of the most popular Reforge courses, one on retention and engagement and one on data for product managers. Shaun is awesome because he's both very tactical in execution oriented, while also being very philosophical and insightful about the craft of product and growth. In our conversation, Shaun shares why most PMs are not good, what it takes to become a good or great product manager, how he thinks about his career, like a Bingo card and why he indexes towards finding very different roles for every new job that he takes. **Shaun Clowes** (00:05:12): Thank you, Lenny. It's really awesome to be here. **Lenny Rachitsky** (00:05:14): I've had you on my radar for a long time and I am really excited to finally have you here and big bonus points for having a very beautiful, sultry Australian accent that always helps with the ratings, I think. I don't know if it's causal, but it's correlative. **Shaun Clowes** (00:05:28): I'm glad to be a bit of a curiosity. **Lenny Rachitsky** (00:05:31): So I want to start with something I totally believe and I love that you have very strong opinion about this, which is just the state of the product management career and how most PMs are not that great and how there's a big opportunity to level up. You just talk about what you've seen there and you're just thinking here. **Shaun Clowes** (00:05:51): Yeah, it's honestly a big conundrum for me. I think it's actually part of... It's grandiose to say so, a bit of my life's work. Why is it that product management is still such a relatively undeveloped discipline? We're 15 to 20 years into this thing. You would've thought that it would be less random than it is. The outcomes are random, the behaviors are random, individual performance is random, seemingly. And so there's something about the current state of product management that isn't getting at the truly important things, the truly value-added things, the right way to think about problems, the right way to think through problems, the abstract reasoning that's needed, there's something that isn't working about it. I spent a long time trying to put my finger on it and then be like, "How do you reproducibly reproduce that?" Reproducibly produce people who can really be really great product managers. **Shaun Clowes** (00:06:39): The thing is that if you think all the way back to it, I spent a long time as an engineer and people always talk about 10 times engineers and I wanted to be a 10 times engineer. I'll leave it to others to decide to tell you whether or not I was or I wasn't, but certainly I wanted to be and I tried to be a really great engineer. And it must be true that if there's 10 times engineers, and I would argue they definitely are, they must be 10 times product managers too. But at the same time, those 10 times product managers, because product management is ultimately about leverage, so it's about helping other people have dramatically more impact than they would if they were unorganized that they didn't have somebody to organize the goals and what we're trying to achieve, then that means that a 10 times product manager has 100 times return or more because they're 10 timesing the return on 10 times resources. **Shaun Clowes** (00:07:23): So the outcomes are so wild, like wildly distributed and the benefits are so good that you would've thought that it would've behooved us. There would've been a way that this had evolved and improved and really gotten way crisper than it has, but here we are. I'm not saying that we haven't gotten better, we 100% have, but I think we could all say that we're not reliably producing 10 times product managers every day of the week. **Lenny Rachitsky** (00:07:49): I love this point and it's especially painful that when someone works with a PM that's not great. There's just this meme of why do I need PMs? PMs are useless, PMs suck, and it just creates that no one's ever like, "Engineers are useless or designers are useless." But there's so many people are like, "I don't need product managers on our team. Never hire a PM," and it just sets the whole profession back. **Shaun Clowes** (00:08:12): When I first started out in PM somebody, it's obviously a chestnut, but he pointed out that realistically when you're a product manager, your job is to say no to 90% of things that get brought your way. And so that kind of makes you the bad person pretty much from the start. And so you're saying no to 90%, so you can say yes to 10% and that kind of puts you behind the eight-ball right at the very beginning, and so you have to very quickly get runs on the board. You have to prove to have the right insights, to have the right data, to make the right decisions or you don't get another go, you don't get another swing at it. So it makes sense that product managers are the easiest to single out and criticize, but that is also what makes it the funnest thing. **Shaun Clowes** (00:08:52): If you think about why do we do this? Somebody once asked me, "Would you retire? Why do people do what they do?" Because certainly at some point it isn't just about the money and at the end of the day product management is so damn fun because it's about trying to figure out an edge. It's like trying to look at the world, find the portion of the chessboard that isn't occupied, but that is valuable and find a way to get into it, invade it and destroy it. It's decisions under uncertainty and that makes it unbelievably fun. Really, really painful and very frustrating and very hard to convince people, but very, very fun. So in equal measures basically. **Lenny Rachitsky** (00:09:33): What's the answer, Shaun? How do we solve this problem? I know you said it's your life's work. What do you find actually helps most in helping PMs level up and become say 10 X PMs? **Shaun Clowes** (00:09:43): I think the most important thing and the chestnut that I repeat to everybody is that at the end of the day, the time you spend looking inside the building doesn't really benefit you very much at all. And Steve Blanken, people used to talk about you should be spending 80% of your time thinking about things going on outside the building. You might not be outside the building, but you should spend 80% of your time thinking outside the building. And I would say that very small number of PMs do that. They get dragged into internal politics, they get dragged into scrum management or scrum execution or product delivery, like elements of the delivery thing and you just can't win that way. You just can't win that way. You can never get an A because you're fundamentally not solving the job. The job is not about execution or anything, it's about finding reliable, differentiated value that you can uniquely deliver into the market. **Shaun Clowes** (00:10:33): So I would say if there's one thing, two things I would say actually that I generally guide product managers to do, one is to always start from the point of view outside the building in every document in everything, always talk from the customer's perspective, from the market's perspective, from the competitor's perspective, and the people who listen to me on that I would say get better almost immediately because they're starting from a place that's easier to understand and then secondarily be data informed. **Shaun Clowes** (00:10:58): They use all of that view of the world, but don't just make up a bunch of statements, support that statements with anecdotes and bits of data. It doesn't have to be a treatise, but convince everybody of what the world really looks like and what the opportunities ahead of the company looks like and good things happen to you. And all of a sudden you go from a world where nobody wants to help you get anything done to where everybody wants you to win. They want you to win and they may not give you everything you want, but they certainly will try because they're like, "Well, of all the bets we could make, this is a good one." **Lenny Rachitsky** (00:11:30): I imagine many people listening to this are thinking, "Oh, I am that person. I talk to customers all the time. I'm always interacting, looking at research, putting data together." And what you're saying is you're probably not doing that enough. Is there anything that you could help someone recognize of, "No, you're actually not doing this enough and you think you are but you're not." **Shaun Clowes** (00:11:50): It's one thing to say you're spending a lot of time looking outside the building. It's a whole other thing to hear from the places you don't normally hear from. So avoid availability or confirmation bias. Most of the time people go talk to the people they always talk to and they learn nothing particularly new. They don't synthesize the results that they got from that conversation. They don't seek out the counterfactual, they don't seek out the proof that they're wrong. They don't analyze what their competitors are doing and figure out what that must tell you about the market. They don't bring back the data of how their product is actually being used versus how people say it's being used. It's like all data and no analysis is not very useful. Everyone can bring back an omnibus edition of random stuff I heard on a Tuesday, but the competitive advantage is extracted out of figuring out what other people don't see, figuring out where we are wrong, figuring out where a well-placed bet could have dramatically outlandish returns. **Shaun Clowes** (00:12:49): And so I think firstly, people often say that they do a lot of this stuff, but they actually don't because they don't have any structured way of doing it. So what they really mean is every now and then I get in a customer call or every now and then I get stuck into an escalation. And so they're kind of conveniently bucketing it. So firstly they don't do it in a very structured way, then they don't bring back analysis, they get true insights from that thing, so they don't really gain very much at all. It's just more activity, no outcomes. People do far too much activity with not enough outcomes and there just isn't enough time in the day to do that to be successful. **Lenny Rachitsky** (00:13:24): You as a product leader is at the Venn diagram center of the sweet spot of where this podcast has been going recently, which is product and growth and how AI helps you with all these things. And so to follow a thread there with synthesizing and understanding what people are saying, user research and surveys and all these things, have you found any tools that you and your team have found really useful to help you do this more efficiently versus traditionally just manually going through all the stuff and finding patterns? **Shaun Clowes** (00:13:55): Yeah, so firstly, stepping back a little bit just into the motherhood and apple pie portion of qualitative research or whatever, I find that most people don't even understand or don't start with a rigorous foundation in what they're going to need to do to get the answers that they want. So for example, your listeners have probably heard about the Nielsen number before, but basically the idea is that once you interview between 7 and 14 people, you stop learning new things. Less than 7, you don't learn enough, more than 14, you start learning anything new. And so if you interviewed two people, you probably don't have enough data. If you interviewed 22, you probably had too much, so they don't even right size their efforts. So that's a problem. So they don't start that way. Then they go into these conversations asking leading questions, which really are designed to get the customer to say what they already want to be true, which is so they haven't done enough research or they've done too much and then they've blown up all of the results before they've even heard anything. **Shaun Clowes** (00:14:48): If you don't right size your research and you don't set this up to learn, then you're going to lose. No amounts of applying LLMs or any type of kind of structured reasoning is going to help you. Because you just basically you're reading back what you want to hear or some weird summarized version of what you want to hear. But stepping back from all of that, what I like to do specifically getting to LLMs is I think that we live in just the most amazing time for product managers right now in terms of being able to analyze vast quantities of information and see the common threads. And so let me give you few examples of that. One might be you can do a bunch of customer interviews, you can put a bunch of customer interviews into ChatGPT and you can say, "Hey, ChatGPT, this is my strategy. Tell me where my strategy does not fit what these customers talked about." **Shaun Clowes** (00:15:40): It's all about the not, not where it does, where it does not. People spend far too much time looking for what they're hoping to see, not for what they're not looking to see. So you can literally ask ChatGPT to help you find where the customer is probing at the edges of what you're trying to do, where it's wrong, where what you're saying is not what they believe. And you can ask it questions like that. You can ask it what your customers are saying would better fit what your competitors are saying. So you can basically say, you can copy and paste one of your competitor's positioning documents into ChatGPT and say, "Is this a better fit for what they have said than my thing?" Which is you can summarize your own strategy, you can take your competitors but public documents and you can ask it to summarize what their strategy probably is. **Shaun Clowes** (00:16:22): And it's actually supposedly good at that because mostly your public documents are actually a summary or at least they're derivative of what your strategy is. So it will give you crazy insights into what other people's, literally their product strategy at times creepy like, "Oh, they will probably do this, they will probably do that. It's more likely they would do this than they would do that." And so normally that type of insight was hard one, it took a lot of sweat work. You basically get to read a lot of stuff. You kind of had to use your brain as this big summarization machine and eventually you knew what you felt about all the things you had read, but you couldn't summarize why. LLMs let you get to that really, really, really quickly in a very structured way, but only if you push at the edges, provoke the answers you don't want to hear, provoke the problems, try and prove to yourself that you are wrong, I think is the easiest way to start trying to use some of these tools. **Lenny Rachitsky** (00:17:15): I love that. And it sounds like in your experience you're just using straight-up OpenAI, ChatGPT, Claude, not any specific tool for user research for this specific use case. **Shaun Clowes** (00:17:26): No, mostly I find that the straight-up LLMs themselves are good enough and we do have some internal tooling that we built around, I don't know if you've ever had Sachin Rekhi on the show, you may have. He was a product leader pretty well known in the gross community, and he was a leader at LinkedIn for a long time and he used to call this concept a Feedback River, and he basically said that really smart product managers are constantly swimming at a Feedback River. They set out to surround themselves by Feedback River and I really deeply believe in that. It's like, "Okay, how can I surround myself with user interview data, with direct customer feedback, with NPS data, with competitor information?" Like I'm always trying to wash myself over with information. And where I'm going with this is that LLMs and tooling based on it can be exceptionally good for this. **Shaun Clowes** (00:18:20): So for example, at Confluent we get a ton of inbound customer requests, as you can imagine coming from the field or directly from customers. We use LLMs to take in those asks to summarize what they're about, to find other asks that are like that one, really in a compelling way, a real way, like a semantic way, not other words, exactly the same, are these the same concept? So that we can look across all of the inbound demand on us and say, "Well, the most popular idea is this one and is getting more popular. The least popular idea is this one. It is getting less popular." In a really deep rich way, even across hundreds or thousands of pieces of inbound feedback. I think it's a really great time to be a product manager if you can put these types of tools to work, but they don't do the job for you, they just help you do these things that are intricate in that job of finding the gaps, finding the opportunities, finding the common threads without necessarily having to do all of it just inside your wear-wear, just inside your brain. **Lenny Rachitsky** (00:19:21): I'm going to stay in this AI river that we're in right now and ask a couple more AI-related questions. And this may be what you just said, but I'm curious if there's more here. You kind of have this hot take that the way AI will most impact product management is data management and data versus models you're building or anything else. Can you talk about what you've seen there? **Shaun Clowes** (00:19:40): Yeah, I mean, I think there's two implications for people as they're building products based on AI and as they're thinking about AI in their workflow. So let's start with the first one, because that's how product managers do product management things. You just asked this question of should it be specific tools built to make AI easier for product managers to use? Or is it in fact more general models being put to work? At the end of the day, these models are very, very, very smart, but they're also insanely dumb and everyone knows that, insanely dumb. In other words, they really only know what they were trained on or what you bring to them right at that moment. In that millisecond, and then they will forget it immediately. And it's very easy to convince yourself that isn't true, but it is actually what really matters. And let me add one extra piece that makes that really important. **Shaun Clowes** (00:20:28): At the end of the day, information has a decay rate. So think about customer feedback, it has a decay rate or what your competitors are doing has a decay rate. So any new piece of data decays in its value to your decision-making very, very quickly, very, very quickly. You can plot your own decay chart if you want to, but the answer is very, very quickly. And so when you think about the job which is synthesizing all of this very complicated information to make good decisions, what does that mean? Well, you've got this synthesis machine, which is this LLM thing that's going to help you do synthesis, but if it hasn't got all that data to do synthesis on top of, it's got nothing. And so that means that LLMs can only be as good as the data they are given and how recent that data is. They're ultimately like information shredders. **Shaun Clowes** (00:21:11): They are limitless information eaters. You can never have enough information to give to an LLM to truly gain its value. The more things you give it, the better it gets. Broadly speaking, that's just not perfect, but that's close enough. And so what that means is as an internal product leader or putting LLMs to work, you need to figure out how to bring as much information about customers or their asks or your competitors, all of it. How much can you find all of it and bring it together and give it to the LLM either in your tooling or even in just copying and pasting or whatever your flow is going to be, that's one thing. But then if you take it beyond that and you go, "Okay, well now I'm a product leader and I'm building an app and I want to put AI in my app, what will make my AI experience really great?" **Shaun Clowes** (00:21:57): It's definitely not going to be the models because these models are mostly going to be somewhat replaceable. And you could say, "Okay, well, is it going to be the prompts?" Maybe, but certainly good prompts are better than others, and that's kind of an ongoing investment you'd probably want to make to ask better questions to get the LLM to deliver better answers. But it's obvious that the real answer is the context, all the context you're going to give it, all the data you're going to copy and paste. And so if you think about, let's say I'm building a, I have no relationship to this, but let's say I was trying to build a human capital like a HCM bot, like an AI bot. Let's say I was working at Workday and I was trying to bring an AI bot. It's pretty obvious that the smarts of the bot would really be related to all of the employee information, but not just that, it would be the benefit's information, it would be the legal situation in the country where that person is currently working. **Shaun Clowes** (00:22:47): It would be the company's policies and procedures that apply to it. So you get what I mean, by about these kind of the jumps of logic and the jumps of data and the way data is all linked together. If you want to have a smart AI experience, you'll convince yourself that all I really need to do is get a model and wire it in and I'll build a little pipeline that will suck some data in and it will whack it into the LLM. And if you think that way, you're going to be very sad, very, very sad for a very long time because you are constantly going to be wrestling with how do I get data to this thing? How do I get good data to this thing? How do we get timely data to this thing? How do I get well-structured data to this thing? **Shaun Clowes** (00:23:21): And so it's a data management problem. It's getting access to good data, getting access to high quality data, getting access to timely data and getting it to the LLM to get the LLM to make a smart decision. That's where 90% of the calories go. Maybe it's a bit like Einstein's thing, "It's 10% inspiration, 90% perspiration." Nobody wants to hear it. Everybody wants to just think about what these really cool models and how smart they are, and the next one will be even smarter. But really it's just the hard work of getting really good data to the LLMs to get them to do good things. **Lenny Rachitsky** (00:23:51): It sounds really obvious as you make this case. It makes me think about at the Lenny and Friends Summit, Mikey Krieger talked about how he had the two types of PM groups within Anthropic. One was focusing on user experience product and the other was working on the model research side, and they realized that all of the success came from the model research work, like making the model and the data they provided the model was where all the value came from, not just optimizing the user experience and they're just putting more and more of their product team on just that versus tweaking UX and buttons and things like that. **Shaun Clowes** (00:24:27): Yeah, exactly right. **Lenny Rachitsky** (00:24:29): Something sort of related, I'm just going to ask one more AI question. I don't want every talk to end up being just all AI, but something that's kind of been a meme recently, and I know you have a perspective on this, is that AI makes it really easy to build products. So in the future, if you can easily clone, say, a B2B SaaS app like Salesforce or Atlassian or whatever your favorite B2B SaaS app, what happens to these businesses long-term? Do they just become, are they all in trouble? Are there going to be 100 Salesforce competitors? What's your sense and prediction on what might happen there? **Shaun Clowes** (00:25:03): Yeah, I think it's really weird. I think people really underestimate where the value is created in these applications and they just kind of get it completely wrong, and I'm not sure why that is. So if you think you bet. So I spent a long time at Atlassian, so I worked a lot on Jira, which many people know, and I spent a long time at Salesforce, so I spent a lot of time in the CRM ecosystem, the marketing ecosystem and all the rest of it. If you want it to be not charitable, you'd step back and you'd look at all those applications and you'd say, "They're all just forms on databases." You'd say, "The Jira is a form on a database, Workday is form on a database, so Salesforce." They're all forms on databases, all vertical SaaS or business SaaS is ultimately forms on databases. And you're be like, "Well, how hard can that be to replicate?" **Shaun Clowes** (00:25:45): And the answer is unbelievably hard, unbelievably hard. And people just think, "You totally get it wrong." Because it's not actually just about the data model. So if you think about, if it formed some databases, it's these beautiful user experiences that sit on top of data models. So whatever the object is, it might be a customer object or a campaign object or an employee object, you could say that, "Well, there's some elements of lock-in in the object, the object itself, like the fields of the object." I'm like, "Pretty boring. That's not very interesting." But sure, maybe. Certainly there's some value in being the system of record like the default that everybody uses. There's definitely some value in the UX. Like, "Well, I want to be the best HR-facing applications for working employee data." Yeah, there's some value there, but the real thing just staring at everybody in the face is it's all about the business rules. **Shaun Clowes** (00:26:35): That is what drives the lock-in because why do you buy Workday? You don't buy Workday for its out-of-the-box configuration. You buy Workday because you want to configure it to be Lenny Inc's HR processes. It becomes Lenny Inc's Workday. It's not Shaun Inc's Workday, it's Lenny Inc's Workday. And actually the longer you have the software, the more it becomes that, the more it becomes less and less like Workday and more and more like your specific company. Which makes sense because it was built to be configured to meet the needs of any specific company, and every company is their own precious snowflake. And as that happens, those configuration pieces, the bit that makes the application native and a fit for your organization makes it a fit for nobody else's organization and also makes it a black box to the point that you don't even understand how it works anymore. **Shaun Clowes** (00:27:20): If you went to, for example, Salesforce and you said, "Hey, could you define all of the processes by which software was sold inside Salesforce?" They couldn't tell you that without reading the code of their Salesforce instance. That's not a proprietary secret. That's obviously true because over time, that's literally how sales happened. There is no other way to do a sale other than through their internal tooling. And so what that means is that it's not the UI that matters and it's not the data model that matters, although those are both very useful. It's the years and years and years of evolution of the underlying workflows of the product to support the customers, but also the customers evolving those workflows to make them work the way they do. And so how does that impact AI companies? You could say, "It's easier than ever to build forms on a database application." **Shaun Clowes** (00:28:09): And so I'm like, "Yeah, okay, that presumably drives the incremental value of every new one of those to zero, right?" So probably leads to more power to the existing winning systems of record because there'll just be a gazillion competitors who would just more form some databases. So like, "How would you ever choose between them? You may as well just go with the winner. Nobody ever gets fired for buying Salesforce or whatever. You may as well start from the kind of the premier vendor." That's one element. You could go the other way and you could say, "I've heard a few people mount this argument," which I think is really interesting that at the end of the day, agents are going to take away most of the use of that user interface. **Shaun Clowes** (00:28:44): So let's say for example, your Salesforce with Service Cloud, I've heard people say, "Well, a lot of those service agents might end up being replaced with agentic workflows. That will mean that there is no person operating the UI. If the UI doesn't even exist anymore, then why do you even need Salesforce? We may as well just have raw database tables on who even needs forms of databases, you can literally just have databases." But that also doesn't make any sense either because the agents have to operate against the rules of the system and the rules are defined by the business processes. So think about Salesforce without a head. Imagine Salesforce had no UI, it would still have those business rules that I was talking about. And those business rules are what define what the agent should do. They're almost telling the agent what it should do and how the world can operate, what is possible, what is allowed. And so from my perspective, this idea that this just completely destroys the differentiation of these kind of business process SaaS applications just seems like a fantasy, a crazy fantasy. **Shaun Clowes** (00:29:42): The only way I could really believe it is if you said, "Well, you could have a new startup that introspected all of the rules that are configured into a Salesforce to try and reverse engineer what your actual business processes are and then kind of operate on top of that." But the best place people to do that would be Salesforce themselves or Atlassian in Atlassian's case or Workday in Workday's case. I just can't see a world in which this... I think one of two things could happen. All this moving to AI makes those applications even better, even more unassailable, they basically get stronger. It makes us stronger or it could enable some new level of applications that come from a more platform based thing, so less a domain specific thing like you ACM or ERP or engineering or less of the domain specific stuff. **Shaun Clowes** (00:30:36): It could enable a more platform like play where you have more business objects and business objects have rules. And you could imagine a world in which there's kind of a whole evolution of new more platform like SaaS applications that do more than one business function worth of the business rules and the way things move around in the enterprise, but that doesn't exist today. So you could say that that could exist and it could say it could be way better than we've ever thought of because of AI. Or you could say that the rich are going to get richer. The most likely outcome is that the currently dominant companies are going to get more dominant, but I don't think this idea that it would just cause a spring up of a whole bunch of new apps that will more easily challenge the incumbents makes any particularly, it's not straightforward to me how that would happen basically. **Lenny Rachitsky** (00:31:18): Wow, that was extremely fascinating and there's so much there. I can go in so many directions. One is I thought you would actually go in this direction, which is distribution advantages become even more important if it's easy to... Like today, I could sit there and hire team clone. Salesforce might take a while, but I could copy it, but by the time I'm done, they've evolved, they're moving, they're adding features, they're ahead, right? You're skating to where the puck was. And so if that's the case, one of the advantages, one of the ways to get anywhere is to have some kind of distribution advantage. It's one thing to have Salesforce as a product clone, another to get anyone to know about it, to adopt it, to sell it, procurement, all that stuff. Do you have a sense of distribution advantages being even more valuable in that world? **Shaun Clowes** (00:32:05): Yeah, I mean, it certainly makes sense. Ultimately, at the end of the day, distribution is always an advantage because the hardest problem is to even be in the consideration set for any given problem. The world is full of problems. It's just when people have that problem, they firstly don't think they're going to solve it at all. And when they do think of solving it, they don't think of you. So distribution is always an incredible advantage. But again, in the world of AI, it seems like distribution is more likely to get hard than easy. So if you think about, for example, diminishing returns on cold email because cold email is getting easier and easier to send even worse spam, it sounds better, but it's effectively causing everybody to become desensitized to everything. I don't know if you've noticed, half the LinkedIn charts now are all basically clearly LLM generated spam. **Shaun Clowes** (00:32:50): I mean, to some degree it's actually worsening the signal-to-noise ratio. And so I think that a lot of the breakthrough distribution mechanisms that startups often use seem to be getting more crowded just in general and more expensive. That doesn't bode well for, "I'm the not as good Salesforce," "I'm the not as good Salesforce, but I'm cheaper." It has to be something different. There has to be some angle upon which you are materially better. And what I saw happening and what I've been seeing happening, and I think it's been really interesting is a lot of modern next-gen applications bringing data as a first-class citizen into the workflow. And I think that that's pretty compelling. So if you look at the next-generation of applicant management products that deal with inbound job applicants, a lot of them now like the latest core ones, they include your time to fill data, they include outcome data of who's got the best hiring outcomes, who over what period of time has the worst attrition, literally all the way back to the interviewers and where the interviews were in the interview cycle. **Shaun Clowes** (00:33:58): So basically embeds data into the whole life cycle. So I think that there are these ways in which startups can bring these experience benefits by just bringing a different approach to the world that does enable them to capitalize on traditional disruptive innovation. At the end of the day, this is just disruptive innovation. It means that most companies have overshot the utility like the average utility, so you can win by meeting the average utility and being different, meet the bar and be different. Meet the bar and be different is the way to cut through. So that makes sense if that's a half decent playbook. But even for those companies, now they're going to have all these AI competitors who are using AI to engineer faster, to build a competitor just like them as quickly as possible and start jamming it into the channel. And it's going to be interesting to see how this whole thing evolves. It kind of got race to the bottom characteristics around it. You're probably right, the distribution is still the hardest part in software, particularly when you're getting started. **Lenny Rachitsky** (00:35:00): So if you have some kind of clever and fair advantage, it feels like that becomes even more powerful. Say have a platform of an audience or something like that. You mentioned this ATS product they really like. Is there one you want to give some love to that you think is really cool that you like or you want to keep it anonymous? **Shaun Clowes** (00:35:16): Yeah, it's Ashby. It's the one all the cool kids are talking about now. And it's funny because people literally talk about it in comparison to all, even the last generation of modern SaaS ATSs or whatever, and they talk about it in glowing ways because of the way they put data inside the actual workflow. So the actions and its outcomes are directly tieable to each other in the application you're doing the work in. I think that's a pretty compelling user experience. **Lenny Rachitsky** (00:35:41): So just to maybe close this thread before I move in a different direction, this point you're making about how valuable data is and how that's at the core of being successful and differentiating in the future, especially with AI tooling and products, any advice you'd give to someone that wants to do that? Is it just make sure you have a, is it half proprietary data? Is it like make it a first-class citizen? What's the advice you'd give to founders who are trying to do this, which you're suggesting? **Shaun Clowes** (00:36:08): Yeah, I, think at the end of the day, it's kind of all of those things, isn't it? If you have first-party data but you can't bring it to bear, then it's not very much use. If you have third-party data and you bring it to bear in interesting ways, the problem with data is we're all surrounded by data all the time. So the data's everywhere. What really matters is the right data at the right time in the right place because we're all humans. And so to me, there are obviously data advantages and there are even data network effects if you can end up in a situation where you have very valuable first-party data. But in any case, it's still about being able to bring the right data at the right place, at the right time for those users, for them to be able to get advantage from it. **Shaun Clowes** (00:36:48): A little kind of segue I guess on that one is I know I spent a lot of my career, weirdly, actually I've been a product person for a long time, but weirdly I've ended up inheriting data teams. So I've actually run data teams at a lot of different companies, which is weird because product managers don't normally own data teams. I think I have just a really massive affinity for data. I used to call myself data-driven, it was kind of my jam. And in hindsight, I look back and I think data is the opposite. Data is more like a compass than a GPS. If you look at data as a way of giving you the answer, you're always wrong. You're always wrong or you're slow. Wrong or slow or sometimes both, because mostly data doesn't give you the answer. It just tells you if what you just said is ridiculous or there's potentially something there. **Shaun Clowes** (00:37:44): So it's more like about disproving whatever you think and you end up being slow because if you try and use data for everything, your brain is ultimately a data sifter or whatever. So the reason your intuition tells you something is because you've seen a ton of data that tells you that this is the most likely answer. And so being data-driven, being data obsessed is it's something you can easily overdo very, very easily overdo. So it's about right-sizing data, having the right data at your fingertips, having the right kind of view on data rather than trying to expect data to give you the answer or trying to use data as a weapon or trying to use data as a way to force people to believe you or to go in your direction. But data is kind of at the center of everything and about how to influence and be successful in products you're building and arguments you're mounting internally and everything else. **Lenny Rachitsky** (00:38:34): I love that you went there. I definitely wanted to spend time on here. It's interesting you say that, there used to be data-driven, [inaudible 00:38:44] data-driven. You created the Reforge course, data for product managers and also retention, engagement course and Reforge. And by the way, we'll link to these. You're still helping with these courses. By the way, they're still running. They're awesome. People love them. **Shaun Clowes** (00:38:56): Yeah. **Lenny Rachitsky** (00:38:56): Great. So we'll point people to those. I love that you're also saying you're like, I think the way you described it to me before, this is your reform data-driven PM. A lot of people say this, they're like, "Don't just do what data tells you to do. Use your intuition, use it as a guide." It's hard on the ground to operationalize that advice. Say to your PMs and your teams when they have data telling them, "Hey, this experiment is a huge success, or there's a huge onboarding conversion opportunity here." I guess just like what's your tactical advice to folks that have data telling them one thing and maybe something else telling them something else? **Shaun Clowes** (00:39:35): I think the first thing I always encourage people to do is to look at a piece of data. If you're looking at a piece of data and the result tells you something that your intuition tells you is insanely wrong, like they probably not right. First, believe your intuition and go and prove yourself right. Don't just take it at first glance because most of the time it's like Occam's razor. The most likely explanation for something that is insanely not intuitive is that it's just wrong, that there's a problem somewhere. Now, occasionally, sometimes you actually will be right. Now those will be paid dirt moments. Those are the moments that make it all worth it. There are times when you do find the negative goal, you're like, you're staring at it and like, "This is it. This was the problem. This was the thing we were looking for this whole time." **Shaun Clowes** (00:40:18): But you have to be very diligent about following it through, really understanding what you're looking at. Is this data representative? Is this data a good sample of the audience we care about? Is it already subject to some sort of selection bias? Oftentimes when I see analysis from different product leaders or even data teams, you can drive a truck through it, literally drive a truck through it. And if you present data with authority and that data is ridiculous or the analysis is just full of holes, you don't just not get benefit for that. You lose a whole bunch of brownie points. It would be better not to show up with an analysis that isn't clear than it would be to show up with an analysis that's dumb. And I see people self emulate on this actually relatively regularly because they just bring a knife to a gunfight or whatever, they did bring in an analysis that is just not, it doesn't hold water and they present it and then get shot down live, which is nobody's idea of a good time. **Shaun Clowes** (00:41:21): So if I give you a little bit of additional tactical things about that, it'd be okay if I'm looking at a piece of data, what was upstream of this piece of data and does that look normal? So this thing happened or whatever, which you're very, very excited about, what happened before that? And does that match what you think should have been right? So what happened before this momentous situation? And then, okay, for that thing that you're looking at, what happened after? If you have an idea of what happened before and after, that gives you some idea of whether or not this thing, is it all worth interesting to talk about? And then go one click above this data that you're looking at. So it's like, these things, let's say I'm looking at onboarding success. Let's say I'm looking at onboarding success to second week retention or something like that. **Shaun Clowes** (00:42:05): I'm like, "I have found this thing that totally crushes it. This intervention crushes it." If you go upstream and you find out that this intervention only applies to 2% of the inbound onboarding stream, it's meaningless. It's most likely just a random aberration. But even if it was not a random aberration, it's not a useful tool. And so you've got to go up and then you might go downstream and you might find, yep, they last for two in the second week, but in the third week they all churn. They're basically pointless. Why are we even talking about this? Or then you might step all the way back and go, "Okay, yes, those people do get retained for longer, but their average ASP is smaller." Because what we really care about, we do care about engagement and we care about more customers, but we want to keep the customers at a high ASP to reach a certain revenue goal. **Shaun Clowes** (00:42:46): The final goal is happy customers paying us money. So that's what I mean about going a click up. If you go a click to the left, a click to the right, so before and after and then a click up and you still see the thing that tells you the story that you want to tell, then now you've got something that's very compelling because people want to hear about that. They want to hear, "Well, what did happen before? What did happen after? And why is that outcome happening?" But you have to really do your homework and really be rigorous about it to avoid fighting fool's gold. **Lenny Rachitsky** (00:43:15): I love that advice. ASP, what does that stand for by the way? **Shaun Clowes** (00:43:19): Oh, average sale press, [inaudible 00:43:22] MRR or some other revenue metric. **Lenny Rachitsky** (00:43:25): Got it. This point you made about how a lot of times experiments show positive and then they end up not being anything, I had the head of growth from Shopify on the podcast, and they do this really cool thing where they keep holdouts for years of cohorts and then it auto emails them I think a year or two later, "Hey, check this and see if these cohorts, this is still higher or not." And 40% of the time, it turns out neutral after a positive experiment long term. **Shaun Clowes** (00:43:50): Interesting. It's really funny because the last time we did something similar, we had a global holdout group actually that was held out of all experiments. The experiment platform couldn't target that group at all. So 10% of all people never saw anything ever. So that's be really, really helpful because you can always compare them against whatever the experience was for any of the same vintage of cohort. I agree with you. But the other thing is I don't really love some of that thinking process just in general. **Shaun Clowes** (00:44:14): It's like, "Hey, let's say an experiment does show a temporary benefit. If an experiment shows a temporary benefit, but that benefit does not persist forever, does that mean the temporary benefit was never worth it? Or does that just mean the temporary benefit was an opportunity to reach another level you just didn't capitalize on?" I don't think there's a perfect answer, is what I'm trying to say. I don't think that the fact that a benefit doesn't last forever means that you failed. But I agree with you that not trying to understand, well, what has the net benefit been, what has the net lift been is also really important too. That's why growth is so hard. Growth is part of product is so especially hard. **Lenny Rachitsky** (00:44:49): Marketers, I know that you love TLDRs, so let me get right to the point. Wix Studio gives you everything you need to cater to any client at any scale, all in one place. Here's how your workflow could look. Scale content with dynamic pages and reusable assets effortlessly, fast-track projects with built-in marketing integrations like Meta, CPI, Zapier, Google Ads and more, A/B test landing pages in days, not weeks with intuitive design tools, connected tracking and analytics tools like Google Analytics and Semrush can capture key business events without the hassle of manual setup, manage all your client's social media and communications from a unified dashboard, then create, schedule and post content across all their channels. If you're working on content rich sites, Wix Studio with no code CMS lets you build and manage without touching the design. And when you're ready for more, Wix Studio grows with you, add your own code, create custom integrations with Wix made APIs or leverage robust native business solutions. Drive real client growth with Wix Studio. Go to wixstudio.com. So you built the first B2B growth team when you were Atlassian, correct? **Shaun Clowes** (00:45:56): Yes. Yeah, it makes me feel like an old person, but yes, it was a very long time ago. **Lenny Rachitsky** (00:46:00): Slash maybe it's a new thing. **Shaun Clowes** (00:46:01): Yeah. **Lenny Rachitsky** (00:46:03): It's either a long time ago or it's just recently figured out this is a thing that you could do in a B2B is focus on growth. **Shaun Clowes** (00:46:11): Yeah, it is. So that was around about 2012, and at that time growth hacking was a thing. People don't really use that term anymore, but in B2C it was a very big deal because people could see Facebook doing their 10 friends in seven days and they could see this kind of thing that was working for people. And they're like, "Man, that's amazing." And at Atlassian we set out to go, "Okay, well, do those techniques work in B2B?" And also, it's kind of obvious now that a lot of them do and that it's worth doing. But at the time it wasn't that obvious because for a lot of B2B companies, I mean, you summarized it earlier, Lenny, distribution covers all faults. Almost all ills can be filled in by really great distribution. **Shaun Clowes** (00:46:52): If you have a really good marketing, a really good ground game, and you're kind of jamming your product into the channel, you're jamming your product in front of people and you're papering over the ugly parts with customer success people and services and consulting and whatever, that people will buy almost any software or you can certainly be successful with a lot of different software. But back in 2012, it wasn't clear of like, okay, which instead you went at this differently and you've heard them in software that sell itself, is the juice worth the squeeze? And now I would say that it's pretty clear that the juice is worth the squeeze to the point that lots of think about this all the time, but it was a bit of an interesting time at that time. **Lenny Rachitsky** (00:47:34): And that was essentially the beginnings of product-led growth. Is that a simple way to think about it? **Shaun Clowes** (00:47:38): Basically it's now called PLG, but yeah, at that time we didn't even know what to call it exactly. **Lenny Rachitsky** (00:47:42): Just growth. So based on that experience, a lot of B2B companies now have growth teams through investing in growth, what makes a great growth team in B2B? Any pitfalls you often find folks fall into that you think they should try to avoid? **Shaun Clowes** (00:47:57): Ultimately, a lot of these types of endeavors are a matter of balance. So what I mean by that is growth teams tend to go through a set of phases. Their first phase is proving their value at all. So call that the gold rush phase. This thing's probably not worth even doing. Why are we doing this, merry band of people out there trying to prove that there's some growth effect somewhere? So that's the proof of phase. And so the advantage of that phase is life's good because there's usually a lot of growths to be found because nobody's gone looking before, so life's good. But it's pretty random because you're just literally searching across a random search phase going, "Have we tried X? Have we tried Y? Have we tried Z?" Then once you get that model going, then it starts to be, "Okay, how do we scale this thing? Is this just a flash in the pan? Do we just find a little bit of low hanging fruit and there's nothing else here, there? Is this just a project we should have done rather than an ongoing thing?" **Shaun Clowes** (00:48:52): So you have to make it a system. You have to prove that it can be repeated, and then you have to scale it. It has to become a thing. It has to become part of your DNA. You have to be taking a PLG lens to everything you do, all the way from paid acquisition to activation, retention, engagement, cross product expansion, upsells, I mean, you name it, all the different ways you can grow a product by revenue or engagement. There's many different ways to go about that. And so you end up having to scale out and be able to do all of those different things. And then you have to figure out how you fit in with the rest of the organization because there's other people who build products all day every day. **Shaun Clowes** (00:49:27): There's other people who sell that product all day, all day. There's other people who market that product all day, all day. And so growth organizations are in this interesting space, they're in between everybody else. They're in everybody else's sandpit in a little bit, in a little way, and they're kind of at the edge of everybody's full-time job and they are very valuable, but they can be complicated because of all those relationships, and because of the way they sit amongst all of the other parts of the organization. So many organizations fail because they don't really find much the wins or when they do find wins, it just seems totally random. Or they do find a lot of wins, but they all can't understand them because they seem like they're just a random walk through a bunch of potential opportunities. There's many different ways to fail to fit as you go through your growth phase from trying the ideas to success, to scaling, to operationalizing. **Lenny Rachitsky** (00:50:18): One of the biggest memes along these lines is a lot of companies claim there's like just PLG rarely ever works. You always, either you try it and it just doesn't work or it eventually just peters out, I guess. Any thoughts on just what are signs that your product has a chance to work, peel product-led growth versus just go straight to sales immediately and don't even worry about this? **Shaun Clowes** (00:50:44): First let's examine the counterfactual, right? So let's start with the opposite of your question and say, "Hey, how would the world be sadder if we all just gave up on PLG?" We just said, "Hey, there's no point in doing it in B2B SaaS." The problem is that there is not a natural force that pulls companies towards thinking about the end user's enjoyment and success early in their journey. There is no natural force, there's no natural kind of a link force. Why is that? I mean, 101, the buyer is the most important person. The economic bar is the most economic person. Their needs are the number one thing. They're usually the person driving the RFP. They're usually the person dealing with the sales organization. So the needs of the person who you hear are usually all feature-driven and they're not from the end users. **Shaun Clowes** (00:51:34): And so you're kind of sowing a seed of your own demise if you don't think about that end user. But it's one thing to say that you should think about the end user, it's a whole other thing to have a system by which you do that because people pay lip service to all sorts of things. But I'm sure you've heard this one before, but in economics, people only do what their incentives told them to do. Broadly speaking, that is what they do, that is what happens. You get what you set out to measure. You get what you give people incentives to do. If there is nobody in the organization whose true incentive is to measure their end user success, their enjoyment, their happiness, their retention, their engagement early on, it will not happen. Or at best it will be a hobby. And so then by extension, if I start from there, then I say, "Okay, let's say it doesn't exist, PLG doesn't exist and therefore it's a hobby and therefore there will be a bunch of hobby people who care about this." **Shaun Clowes** (00:52:23): Then you ask yourself, "Okay, will that mean that there will be many products for which those experiences really suck? And does that mean that that will be an opportunity for competitors of those products to be better at that? And is that a differentiated competitive advantage?" Yeah, I'd say it is. I'd say it is. And so I just work my way backwards and I go, "Okay, you can say that your PLG investment might be too high." You could be like, "Well, if I invest more, I won't get any more juice. I can't spend my life just experimenting in the onboarding. That's not the only thing that matters." And that's very, very true, but it's very hard to argue it should be turned to zero. **Shaun Clowes** (00:52:59): And so to me, therefore it's about the balance. It's about, "Okay, how does PLG fit with the other different ways that I grow in my business?" At Confluent, for example, we have a PLG function. We do grow with self-serve signups. People who sign up, literally their credit card, lots of them sign up and they're very successful, never speak to us. We also have an enterprise sales team that sells directly to very big companies, some of the biggest banks in the world, the people you would definitely know of. I don't think it has to be one or the other. I think that it's about a balance. It's about getting the motions to work and for really sophisticated companies, the people who really nail this, it's about making both motions work together. If you can get a PLG motion work to feed your sales team and a sales team motion work to feed your PLG funnel when the sales leads aren't ready yet and you can get those motions into playing with each other, you can make a lot of money. **Shaun Clowes** (00:53:52): It can be an extremely successful way to go to build a very resilient business. Why? Because you get a lot of customers and you get a lot of revenue. You can't be that successful as a company if you have a lot of revenue, but a small number of customers because you're captive, everyone knows that. You can't be that successful as a company if you have a lot of customers, but not enough revenue because you shouldn't have enough money to sustain operations. So the magic is in having both, a very large number of customers and a very large amount of revenue, it's very hard to knock over a company like that. If I look back on my time at Atlassian, and I think that they shared their most recent numbers, I can't remember what it was, but it was in the public data or whatever, something 80,000 or 100,000 customers, something like that. **Shaun Clowes** (00:54:30): That's a lot of customers. That's a lot of customers. Let's say you're going up against Jira and you're like, "Yeah, man, I'm going to pick off 1,000 customers from Atlassian." That's a lot, right? That's a lot. Obviously 1,000 customers is a lot. You only have 19, sorry, it's going to be 89,000 to go or 79,000 to go, or however many it is to go. I can't remember their exact number of customers, but it's very hard to assail a company which has a very large number of customers and a very large amount of revenue. And so that's why I think that PLG as a mechanism is incredibly important for almost any type of company, if you can make the motion work. Obviously there are companies for whom the motion just isn't relevant, but for those where it does matter, it seems like the juice is worth the squeeze. **Lenny Rachitsky** (00:55:18): That was an awesome answer. I looked up last year and they have 300,000 customers. **Shaun Clowes** (00:55:23): Oh man, I'm so far off. When I left it must have been 80,000 customers. **Lenny Rachitsky** (00:55:28): They've done good work since then. Also, you're talking about incentives and how the power of incentives. Charlie Munger has this great quote I looked up just to make sure I get it right. "Show me the incentive and I'll show you the outcome." **Shaun Clowes** (00:55:40): Yeah, exactly right. I've seen cases where a sales team was people trying to get a sales team to do a PLG motion, and you can beat them over the head as much as you like, you can get into a meeting and tell them that you really, really want them to do this, but at the end of the day, they're not going to do it. And the same is true for every other kind of function. It's just the nature of things. **Lenny Rachitsky** (00:56:02): I have some newsletter posts around the stuff of folks want to dig deeper. Also, Elena Verna had an awesome podcast episode talking about product-led sales and kind of the combination of these two things that we'll point to.. Just a whole other topic we can go deep, deep on, but we're not going to do that in this episode. Maybe just one more question. So you mentioned all the companies you worked at, so you've been at Salesforce, chief product officer, MuleSoft, specifically within Salesforce, Metromile, Atlassian, Confluent now, a lot of really interesting and different roles. How do you choose where to go work and how do you choose which opportunities to take? I imagine you have many options. **Shaun Clowes** (00:56:42): I have to think of my career. So in hindsight, looking at it this way, Lenny, so I don't know if forward-looking was obvious to me this way. But looking back, my career has been a little bit like a bingo card. I've always been looking to fill in boxes I didn't have filled because I felt like that would make me a better professional. It's like if I didn't know anything about that specific type of sales model or that type of marketing or that type of product management or that type of product or that layer in the stack or that kind of thing is like, well, if I learn about that thing, I will become more versatile. So actually two things, it's fun, it's fun to learn something new. It's fun to prove to yourself that you can do those new things and then it makes you more versatile because it means that any given problem you go up against, you've seen something that pattern matches to it. **Shaun Clowes** (00:57:29): It kind of feels like you end up bringing a gun to a knife fight in a way because every problem you look at, you're like, "Oh, I have seen this from the other side. I've seen this from some other angle, and so I know that this is likely to work and this is unlikely to work." And so when I joined early on in my career, I was working for a big enterprise software company, sorry, small enterprise software company that sold to the Fortune 100. When I joined Atlassian, and like I shared with you, we had no sales force at all actually at all. Literally nobody to sell the software. It sold itself or it didn't get sold at all. And we grew to have 80,000 customers. It was just pure product. They had growth and just an incredible company. Then it was at Metromile, which was a consumer company that got acquired, made an insurance product for end consumers. **Shaun Clowes** (00:58:13): So they got nothing to do with technology products, like literally a complicated Internet of things device you installed in your car, but ultimately it's an insurance product that you'd sell to grandmothers in Florida as much as you would ever millennials. And then at MuleSoft to totally back end software that's used by IT organizations and a consulate infrastructure that's used by developers everywhere to build really interesting data-driven applications, data powered applications to do all sorts of things in real-time. And you look at across all that and you go, "It's all a bit random." But I didn't see it that way because I learned, I actually was in sales for a bit, so I ran a pre-sales engineering group, went around the world selling software. So when I joined Atlassian, I wanted to kind of understand what it was to sell software at massive scale with no sales team, can it even be done? **Shaun Clowes** (00:59:01): And so I learned a lot in my time at Atlassian. When I went to Metromile, I'm like, "Well, I've never built a consumer product before." I can say that I've actually built a product that's touched many millions of people because Jira has, so I felt pretty good about that, but I'd never built one that I could say, "Yep, a consumer, your average consumer can use this thing. It's so simple. Even my grandma can use it." I'd never built a product like that. So I got that experience at Metromile, which is really fun. I'd never worked inside an organization as big as Salesforce or an organization with as good a sales motion. You talked about distribution earlier. Salesforce is an absolutely insane distribution machine, just an incredible company with just an amazing distribution network and a fantastic marketing approach that it's like a PhD in marketing. **Shaun Clowes** (00:59:44): When you spend your time at Salesforce, you're like, "This company is just one of a kind. It's a one of kind, and it's so outlandishly good at one specific thing." And so looking back, all of these jobs have been, when I say bingo card, I've just got an outlandish education in these areas that are not obvious at all. And once you've seen them, they're like superpowers. They're superpowers to be able to bring that same experience to bear on things. And so one thing that I really I'm trying to figure out is why often people don't do that. And oftentimes people stay in a very specific domain. They prefer to stay in a domain or they prefer to stay in a specific kind of type of company or a role that works in a certain way, like companies that have the same operating model or they plan the same way or they try to stay with things that are pretty similar. But it seems obvious that the most likely way to really grow is the opposite. **Shaun Clowes** (01:00:41): It's to constantly be choosing things that are either outside that, not totally outside the lines. Don't jump out of a plane if you've never parachuted before. Obviously you want them to be in some way and adjacency, that you want them to have something in common with what you know, but you want them to stretch you and change you. I had a really transformative experience many, many years ago when I was at Atlassian and a guy called Tom Kennedy, he was our general counsel, so chief legal officer basically, and a lifelong lawyer, very smart guy. I liked him very, very much. But just a lawyer. Just a lawyer, corporate lawyer, corporate counsel, I'm sure you know what they're like. And really great guy. And I remember, so mostly in our meetings he didn't talk that much except about legal things. But I remember in one meeting we were having this vigorous debate about a product strategy question about what we should do. Should we go left or should we go right? **Shaun Clowes** (01:01:39): And as usual, he's there and he's mostly just staying silent. And then eventually the conversation's been going on for 15 minutes and he is like, "Hey, everybody, a year ago we talked about X, Y and Z," and he proceeds to lay out our product strategy at that time, and he's like, "Just recently we said the following things, and that was a product strategy, whatever. Now you are saying this. Isn't it obvious that isn't this? What you guys are saying is not congruent with that, and if you really meant what you said back then we should be doing X." And again, the room went silent, everybody kind of turned to him, kind of nodded, and then everyone went, "Yeah, okay, I guess we probably should be doing it differently." And so the meeting stopped when the GCE randomly mentioned that he deeply understood our product strategy and he knew enough to be able to contribute in that way. **Shaun Clowes** (01:02:24): And so the life-changing part for me about that was just this realization that if I'm going to be a really great professional, the type of professional I want to be is that type of person. The type of person who can contribute to the whole company in all sorts of ways, doesn't spend all of their time in everybody else's business, but understands the business and has the mental horsepower and the experience to be dangerous in all sorts of, and I mean, that in a compliment way. I don't mean that in a negative way, but to be dangerous in all sorts of situations. I think that when you have leaders like that behind you and with you, then you're just unstoppable. You're an unstoppable force in business when you have that motion happening. **Lenny Rachitsky** (01:03:06): Wow, that was an awesome story and an awesome perspective. It's similar to the advice I always give PMs of people always wondering, "Should I go deep on a specific subject? Should I just try different things?" And I find just variety, especially earlier in your career is really powerful, not just to help you discover the thing you like, but also to your point, just using insights from all these different parts of the product and internal tools and trust and safety and platform and consumer product side and growth and just core stuff. The more of that you have, the stronger you get. And I feel like another benefit of your approach is if you work at just B2B SaaS companies, if you have too many of that on your resume, it's very hard to get hired a consumer company. And so just having it creates a huge optionality for you if you do, which you did. **Shaun Clowes** (01:03:57): Yeah, it's interesting because people used to talk about people who are T-shaped or whatever, and I've never really loved the analogy because it's more like people are scribble shaped. I mean, there's the really best people you've worked with, they're more like scribbles than they are T-shaped because of course you want to be horizontally capable, so you want to be broad and you do want to be deep, but you actually want to be deep in way more than one thing. Now obviously when I say deep, I don't mean I'm not able to do the job of our finance function all day every day, but I'm 100% good enough to go three clicks below the simple financial analysis. I can go reasonably deep in our financials because I want to and because it's partly it matters. It's important to be able to do that. And so maybe a different way to think about that bingo card is I've rarely regretted going deep in something that isn't quite my job. **Shaun Clowes** (01:04:51): I've rarely regretted it. The worst case scenario is I've learned something new that I will never use, which I guess at least that made my brain slightly more agile. I don't know, there must be some potential benefit of that. But the very best case scenario is that when I least suspect it at some point in the future it will turn out to be the thing that matters. It will be the tool that I need, but I'm facing some important problem and I will be like, "Oh my god, this was worth every cent." And so if you think about it on an ROI basis, doing things that aren't in your wheelhouse, that aren't the things directly in front of you, the ROI can really be outlandish. It can be off the charts great, but I guess it's speculative. Because you don't know you're going to need it tomorrow. You don't know if it's going to be something that's going to be a regular tool you use. **Lenny Rachitsky** (01:05:33): What's interesting is the bingo card is the analogy. Is there a bingo moment at the end of this? Is there retirement? **Shaun Clowes** (01:05:41): Oh, you mean you've got everything. You've got the collectible Pokemon? **Lenny Rachitsky** (01:05:45): Yeah, you collect them all. **Shaun Clowes** (01:05:46): Yeah, I was working with somebody at Salesforce and he'd been there a long time, very, very, very successful person. Honestly didn't need to work anymore. And he said something that I found really useful. He's like, "Well, now I'm at the point of my life where I want to work at the intersection of things that I am good at and things that will be valuable to the company to do." So basically it feels like the reward of completing your Bingo card is actually to just get to spend more time doing things that are leverage, that you enjoy and that are high leverage. And so that seems like a good outcome to me. I don't think most people are going to work and hopefully have some sort of great financial outcome and then go, "Well, that's it. I'm picking up stumps, I'm retiring." I think for most people, achieving some sort of financial outcome or some sort of independence or whatever is really just another stage. At that point it will be, "Okay, well now what do I do? What do I do with my life?" **Shaun Clowes** (01:06:49): And so that was why I said earlier that at the end of the day, product management is at times the worst job in the world and at times easily the best. And it's both and it can be both. And so it's hard for me to think about if I think about the things that are the intersection of what I'm good at and are valuable to the world, product management is a pretty fun one to do and it's different every day. So I think we're pretty privileged. For those of you who listen, I mean, obviously your podcast reaches a lot of product people. I think we're pretty privileged to be able to operate at that intersection, but it's not easy because you got to show value. It's a very complicated job to show value in and to demonstrate value to the world, and it's constantly being attacked, like you mentioned, but it's still amazing when it all goes right. When a product is very successful in the market, it's hard to describe the joy you get from that. **Lenny Rachitsky** (01:07:46): Kind of along those lines to close out our conversation before a very exciting lightning round, I want to take us to failure corner. People listen to these podcast episodes and everyone's always just sharing all these wins, everything's always going great. The CPO of this, CPO of that, just moving on up and people will want to hear times when things didn't go right. Because those are stories people don't share as often. Can you share a story when something didn't go right, when you maybe had a failure in the course of your career? And if you learned something from that experience, what you learned. **Shaun Clowes** (01:08:18): I mean, there's a lot of things that didn't go exactly to plan, Lenny. Very early on in my career, I was still a developer and I accidentally deleted one of the core systems of the company that I was working at. So that's going to go down in infamy, but luckily that one's far in the rear-view mirror. That- **Lenny Rachitsky** (01:08:38): That wasn't Atlassian? **Shaun Clowes** (01:08:41): No, that was far pre-Atlassian, but very bad. Yeah, the one I like to talk about, I wasn't directly responsible for it, but I feel responsible for it. I was at a company and we launched a product. That was one of those products that in hindsight should have been really obvious it was going to fail, but for some reason we were all blinded by the potential. It was a product that was about, it was basically to measure the environmental impact of your company and to help you reduce the environmental impact of your company by doing, think about it as a power management, building power management, managing the power drawer of computers, managing the power drawer of AC and all of that stuff. That was the vision basically. It's like a manage your environmental impact of your business. The idea was pretty cool at the time, and also it was the right time for that, and it's still a thing. **Shaun Clowes** (01:09:33): It's still an area of active research and investment or whatever, but it was one of those things, talk about the wrong company, wrong place, wrong time, wrong distribution. We had literally no right to win, no right to play, just absolutely no business in hindsight being in that business. And I feel really bad because I, again, good idea, wrong company. And at the end of the day, we launched the product. We actually kept the product in market for two years, and the final straw was weird. The final straw was actually when a customer finally wanted to pay for it. It had been in market for two years, and we found ourselves with a customer who wanted to pay millions of dollars for it. They were ready to sign on the dotted line, and that was actually the moment we decided to kill the product because we were like, "If this person signs this piece of paper, we are stuck with this forever. This one customer will be bound by contracts for however long or whatever." **Shaun Clowes** (01:10:29): So we actually ended up killing it. At the moment after two years of failure when somebody wanted to pay his money for it. And I look back on that and I'm just like, "Man, that was a really big..." I feel really bad because I'm like, "It should have been obvious. It was obvious and we should have been able to call a spade a spade and I guess speak truth to power." But instead it kind of got through to the keeper and turned out to be a real accidental drain on resources for years and just a big mistake. **Lenny Rachitsky** (01:10:58): So is the lesson there, just be real with yourself? I like that you have this forcing function of like, "Okay, this is getting for real now." Is it like, "I wish we had an earlier forcing function to force us to make a decision?" **Shaun Clowes** (01:11:11): Yeah. I think if I could do it differently, I might not have necessarily been able to 100% change the decision, but I should have tried. I mean, it was pretty obvious after six months, this thing was a bit of a zombie product walking, and the least I could have done is said, "This thing is dead." We could have called it dead way earlier, but instead we proceeded for another year and a half investing in it. And so that's the bit that makes me feel like real bummer about it. **Lenny Rachitsky** (01:11:39): It reminds me a recent episode with Raaz who is the CMO at Wiz, and she joined us the first PM and a few weeks into it with doing tons of calls with customers she's like, "I think I need a quick... Because I don't really understand what we were building. I don't get it." And everyone's like, "I don't either." And it just, yeah, the founders just had a vague idea what they're doing, but they didn't really have an idea. And that just sparked a, "Okay, wait, no one actually does. Let's actually get more concrete." And it helped them pivot. And now, I don't know if you know about Wiz, but they ended up being the fastest growing startup in history. **Shaun Clowes** (01:12:19): Yes. Isn't that amazing, right? It doesn't mean it's permanently fatal, but asking that question and going through that reckoning turns out that came out stronger. **Lenny Rachitsky** (01:12:29): Scary, but it turns out it's for the best often. Before we get to very exciting lightning round, is there anything else that you want to mention or leave listeners with maybe a last nugget, something that you think might be helpful before we wrap? **Shaun Clowes** (01:12:41): Maybe a couple of different things that I think are sometimes well understood, but just repeating them I guess because they're very valuable to me. One is that if you let your calendar rule you, then nothing good will happen. I know people talk about that a lot, but it's surprisingly common in product management in particular that people end up ruled by their calendar. And so it's related to that whole look at spend 80% of your time thinking about things going on outside the business. Easy said, very hard to do, and if you don't do it, no one's going to do it for you. And so it is really hard to be successful unless you find a way to force that to happen. So to repeat that, also, somebody said this to me, I never looked up the quote, but apparently Colin Powell said that if you're making a decision with less than 30% of the available data, you're making a big mistake. **Shaun Clowes** (01:13:32): If you're making a decision only after you have 70%, either the 70% or 77%, I can't remember the exact number, when you have 77% of all the available data, you have waited far too long. And I've always found that very insightful and it relates a little bit to what we're talking about about data earlier, but at the end of the day, we get paid in product management to make decisions, good decisions, paid to make good decisions that will deliver business benefit. And a decision with too little data is fatal. A decision that takes too long and collects too much data is also fatal. So everything, it's about trying to find the balance of all of these different things to try and deliver business advantage. **Lenny Rachitsky** (01:14:07): A great way to circle back to all the things we've been talking about. With that, we've reached our very exciting lightning round. Are you ready? **Shaun Clowes** (01:14:15): Yes. Let's do it. **Lenny Rachitsky** (01:14:17): Let's do it. What are two or three books that you have recommended most to other people? **Shaun Clowes** (01:14:23): Yeah, they oldies but goodies, is probably going to be The Lean Startup that I still find actually really good. And the key lessons in there I still think are very applicable to a lot of people, particularly the cohort analysis bit, which for some reason I still don't see people do anywhere near enough cohort analysis. So there you go, that's my little tip. And then INSPIRED: How to build products that people love by Marty Kagan and the Silicon Valley product group. That's an oldie but a goodie. I think it's got a lot of the key lessons of product management in it, even though it's been around for a long time. **Lenny Rachitsky** (01:14:53): Those are some classics. Very cool. Do you have a favorite recent movie or TV show you really enjoyed? **Shaun Clowes** (01:14:58): I'm watching a program. I don't get to watch very much TV, mostly at night. I like to watch things that are extremely light, that just don't at all inspire any element of stress and that are very short. So basically short and funny is basically my thing. And there's a new program on Netflix, I think it's called Detroiters. **Lenny Rachitsky** (01:15:18): Oh, I've been watching that. **Shaun Clowes** (01:15:20): Yeah, it's really funny. I really like that. It's so ridiculous, but very funny. So I like that. **Lenny Rachitsky** (01:15:24): The main guy, he's so funny. I forget his name. Tim Sweeney or something like that. Yeah, he's so good. Good one. I've been watching that, I'm loving it. It's very quirky. I think the New York Times quote on there is "Very weird," the quote. **Shaun Clowes** (01:15:38): It's so weird. In the first episode I'm like, "What is this show?" It's not even clear what time it set in, and it's very weird. It's really cool. **Lenny Rachitsky** (01:15:44): Yes. Well, good way to describe it. Next question, do you have a favorite product you've recently discovered that you really love? **Shaun Clowes** (01:15:50): Yeah, this one, some of your listeners might be using it, but Glean, it's a pretty well-known startup now. They recently raised a ton of money. We've been using Glean at Confluent for a long time and it's just amazing. It's just amazing. I can't describe how good it is. And I don't say this lightly because I think search, like business search is probably one of the hardest problems in computing. Actually getting it right is one of the hardest problems in computing. Amazing. It's not often I use a product and I'm like, "This thing is 10 times better than anything that's come before it." It's one of those for me. **Lenny Rachitsky** (01:16:25): What's the simplest way to understand what it does for you? **Shaun Clowes** (01:16:28): It searches all of our organization's knowledge. So the thing you were just saying before, you're like, "What does AST mean?" If I had that in a meeting, I just open my new tab, it'll automatically take over my new tab or just like, "What does AST mean?" And it will summarize back to me what AST means and it'll give me a link to all the documents inside our company that just grab what AST means and then it will tell me who the expert in AST at our company is. It's like having a second brain. It's an insanely cool organization searching. **Lenny Rachitsky** (01:16:59): Great tip. Okay, two more questions. Do you have a favorite life motto that you come back to share with folks, find useful and work during life? **Shaun Clowes** (01:17:07): I think about this one a lot. When I started off in my career, I was an engineer's engineer. I used to very much about technical correctness and what computers were capable of, and technical righteousness, the right answer rather than there is only one right answer and whatever. It's a long-winded way of saying that I often think about this phrase, which is people don't care what you know until they know that you care. And so I've realized that really being able to influence people, it doesn't matter about whether or not you're right or whether or not you're wrong. And at the end of the day, it's first about trust and about relationships and caring about what each other's outcomes are, what their incentives are, and all good things sit on top of that. Once you have those kind of foundations, then you can build really good partnerships and that's where good progress comes from. **Lenny Rachitsky** (01:17:55): Wow, that is so good. It connects with Radical Candor, similar in theory of just caring. People need to feel like you care deeply about them before they take your advice. And it also connects with this parenting book I'm reading called Listen, that a previous guest recommended, which is all about how your kids have problems when they feel like your connection to them is weak. And so the solution is to build a stronger connection for them to know that you cared deeply about them. So this is really, connected so much of what I've been reading. **Shaun Clowes** (01:18:26): Yeah, exactly. **Lenny Rachitsky** (01:18:26): Great one. Final question. You were born in Sydney, folks can maybe guess by your accent. If someone were to visit Sydney, any tips, anything you think they should check out, favorite thing in Sydney? **Shaun Clowes** (01:18:38): Yeah, Sydney is a really beautiful city and it's kind of famous for its beaches and it's basically a metropolitan city. People probably be very surprised when you visit it. It's a very big city, very metropolitan, a little bit like New York, but New York with really beautiful beaches, if you want to think about it that way, it's kind of crazy. But there's actually a ton of really cool nature and beautiful things all around Sydney. And so if you want to do something like off the beaten path, you can actually go to, there's an area called the Blue Mountains, which is like an hour and a half drive from Sydney, and you can abseil down a waterfall, which is, well actually firstly you go canyoning through a canyon full of water, and then you abseil off a waterfall at the end. And if you're looking for just a really beautiful, fun kind of adventure like thing, an hour and a bit away from a massive metropolitan city, that's my sort of happy place. Really beautiful outdoors stuff while also next to a beautiful city. **Lenny Rachitsky** (01:19:31): And you said you sail, what sort of sail off a waterfall? **Shaun Clowes** (01:19:34): Abseil. You might think of it as rappelling. Rappelling, I think. Yeah, lowering yourself down on a rope or... **Lenny Rachitsky** (01:19:41): Got it. Because when I hear sail, I'm thinking a boat just jumps through over the waterfall. **Shaun Clowes** (01:19:47): Oh, no, abseiling which is also, I think in the States you guys call it rappelling. **Lenny Rachitsky** (01:19:51): Rappelling, yeah. Wow. Very cool. Shaun, you're awesome. This was extremely cool. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out? Also point folks to your Reforge courses that you created. And final question, how can listeners be useful to you? **Shaun Clowes** (01:20:07): Sure. Yeah, so my Reforge courses, you can check them all out at reforge.com, as you mentioned, the retention, engagement course and the data for product managers course, so love to see folks get some value from that. Lots of people have been through those courses already and I really get a lot of value from it because like I said, one of my goals is to help all of us be better product people. I think our leverage could be massive. Where you can get in touch with me, obviously on LinkedIn, but also ShaunMClowes on X, if you want to get in touch. And in terms of being useful to me, I mean, broadly speaking, I'm always open to new ideas. If people have ideas about how to do better B2B, PLG, better B2B product-led sales, for example, better ways of going about distribution and product-led sales and product-led growth inside enterprise companies, hey, I'm open to learn myself. We're all in one big journey learning how to do this better. **Lenny Rachitsky** (01:21:01): So true. Shaun, thank you so much for being here. **Shaun Clowes** (01:21:05): Awesome, thank you very much, Lenny. It was great. **Lenny Rachitsky** (01:21:07): Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at LennysPodcast.com. See you in the next episode. ---