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Alex Komoroske: Why gardeners beat builders in the AI era

Through slime-mold metaphors, the adjacent possible, and squishy LLM duct tape; Komoroske's strategy salons grow taste, kayfabe-aware bets, and bits and bobs.

Alex KomoroskeguestLenny Rachitskyhost
Oct 3, 20241h 24mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:53

    Introduction to Alex

    1. AK

      (instrumental music plays) 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 garden, things that can grow on their own and that you can sort of 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 (laughs) that people get building products nowadays. But I think it's a very powerful approach that works in a lot of different contexts.

    2. LR

      (instrumental music plays) Today my guest is Alex Khamarosky. 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. 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 am sure this is going to get your mind thinking in completely new ways. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcast app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Alex

  2. 1:536:20

    Alex’s Bits and Bobs document

    1. LR

      Khamarosky.

    2. AK

      (instrumental music plays)

    3. LR

      Alex, thank you so much for being here, and welcome to the podcast.

    4. AK

      Thanks for having me.

    5. LR

      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.

    6. AK

      (laughs)

    7. LR

      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?

    8. AK

      Yeah, so it's, it's ... I think it's like 600 pages now. It's just one Google Doc.

    9. LR

      (laughs)

    10. AK

      Every so often, almost every day, someone will accidentally add a suggestion to 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 like taps on adding a comment or something. And it's ... I, I take a lot of notes. Uh, 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." Um, it's not that I'm just, uh, disengaged. I just, I, I try to, like, collect all these ideas. And then once a week I go through and I take a few hours, and I just reflect to myself and try to find patterns and unpack and find meaning in things. And I write those down, and I started, um, you know, sometime in the past sharing those publicly, and, uh, it's now become a thing I, I literally can't stop doing. I just find someone was like, "Oh, if you get more exposure for this, if you broke these up into Tweets that you sent out once," you know, you know, throughout the day. And it's like, "Dude, I do this for me." I'm, like, happy to let other people see and, like, peek into my weird mental process if they want, but this is 100% about, uh, my own self-reflection. Um, and it's not designed ... I don't want anyone to, like, feel compelled to read it or, like ... 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 to ... 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 like, "What are you talking about?" (laughs) And I do that specifically. I don't want anyone to read it and be like, "Oh, that sucks. It wasn't worth my time." It's like, who, like ... It's a two, 600-page Google Doc of, like, my just unspooled insights, (laughs) like, you know? It's, it's okay for you to not want to dive into that. (instrumental music plays) This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. (instrumental music plays) 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 V-A-N-T-A .com/lenny.

    11. I

  3. 6:2010:10

    The Compendium and note-taking process

    1. AK

      started it many years ago, the same conceptual thing, taking a bunch of notes. I have a thing called the Compendium, which is an open source tool. Um, if you look at it currently, it looks like I haven't touched it in years. But that's actually incorrect. Um, 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 will make sense to me if I were to read it in a year. And also I built a feature into it that uses embeddings to find similar cards so 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 put them, I have a little export thing, I put it into Google Doc and oof, while the kids are napping on the weekends, I just kind of go through them and try to distill them a little bit more, um, uh, in a more long-term format. Um, and then on Monday mornings, I publish them. And, uh, again, it's a, a deep, for me, it's like a, I can't imagine not doing this. It is the, the place where I find most of my most interesting insights, is by reflecting on interesting conversations with people.

    2. LR

      As we get into the conversation, people get, 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 like-

    3. AK

      100%. I mean, I find that like when you're, when you're busy, you're constantly just go, go, go, go. There's no time to, like, do any deep thinking. Deep thinking takes time and space. And you got to create that space. Like, you know, the mundane, pointless bullshit will cut, 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 a, that's one I'll keep." And, uh, I've told people, like 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." Like, first of all, I will line up my, like, output any day of the week, you know? I'm, 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 slinging, you know, 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 at the, before the week started would have saved me tons of time and effort that week?" 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, it, 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. And you also find these interesting ideas sometimes where you look at this problem that you're banging your head against and you go, "Oh, wait, if I went like that, that would have a wildly different dynamic." And you can only find those when you take a step back. And I find that people, I, I told someone, um, I mentored someone, or I've mentored hundreds of PMs over the years, and I told someone that at one point and they go, "Ugh, I wish I had the time." And it's like, you got to make the time. All of us are busy and we'll 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 on, you know, intrinsically. It's something I do because I think it makes me more productive and effective.

    4. LR

      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 gonna do that. That could be another episode we do.

    5. AK

      I can go on for that for hours, yeah.

  4. 10:1014:24

    The impact of AI and LLMs on product development

    1. AK

    2. LR

      What I want to do instead is pick on some of the bits and bobs that you've been focusing on and 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 to this podcast are PMs, engineers, founders, people building software. I know 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 gonna be." So let me just ask you this. How do you anticipate LLMs and gen AI are gonna change how products are built in the next three to five years?

    3. AK

      I think it, 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 are formed principally by the distilled intuition of all of society into a thing that operates between a c- in a cost structure between a human and plain old computing. Uh, 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 like, you know, good enough in certain contexts. And also, it means that there's certain software now that isn't plain old computing that it can re-run cheaply. It's relatively expensive marginal cost. 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 cost even with it, uh, with inference costs declining. So I think the way th- 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. Like imagine if you were locked in a room for, for your entire career, no windows, and you have all these experiences, you're getting all this know-how, you're getting this kind of sense of how things work, what will happen, and then imagine that room tilts on its, and its axis by five degrees.... everything looks roughly the same. And yet now, the dynamics, 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 and never changed, that it's just a, a blink in your head. And now, everything has changed effectively for, for your perspective. And all kinds of intuition is now wrong. I put this thing on the table, it's gonna stay there. And then it slides off and falls into the wall. You know, all kinds of weird stuff will happen. And I think LLMs to me feel like that. Like I, I can't tell you the number of people who are, um ... And at some point like a year or two someone, uh, came to me like, "I just built a prototype product that would have taken three months." And, and I can't ... Because we founded a startup. It's like, how differentiated do you think that is? Like everybody can do that now. You know? Like it changes the basis of competition. I think today, I see a lot of folks using LLMs. And LMs 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. Um, and only some people have learned the skill of programming for like the arcane, magical incantations to make computers do exactly what you meant. Now LLMs can do all kinds of stuff. And they don't do exactly what you told them. And so, but they do typically do kind of roughly what you meant. And so there's places where people will build products and they'll say, "80% of the time, 90% of the time, it's great. 5% of the time, it punches the user in the face." And they're like, "Oh, we're gonna reduce the number of times it punches them in the face." It's like even if you get it down to like 99% of the time, it's fine. If it punches you 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? People use these things a lot as like oracles. "I'm gonna have it, I'm gonna formulate the answer, and it's gonna be a fully fledged answer." And of course Strawberry has been really stable and I've gotten the chance to play with it. Um, 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, uh, LLMs for granted? How can you assume that you now have this magical duct tape? Don't assume it's gonna solve all your problems. Don't assume it's gonna do a, you know, autonomously, uh, be able to give high quality results in every case. But what can you now build, now that you have magical duct tape?"

  5. 14:2419:02

    Skills to lean into as a product manager

    1. AK

    2. LR

      You were a product manager for most of your career.

    3. AK

      Mm-hmm.

    4. LR

      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 gonna be matter most. You know, there's like hard skills, there's soft skills, there's getting more technical, there's getting more product/business oriented. A 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?

    5. AK

      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, using, uh, uh, AI is web sim. Web sim is so weird. (laughs) Like what a weird idea. Like who ... Why? And yet 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, uh, interesting patterns are found. Because right now, we're so used to ... Like, you know, if the playbook, if the cost structures have changed, the kinds of things that are now possible, the playbook is wrong and we should throw it out or at least ignore it to some degree. So like it will feel like we are, um, navigating through a whole new industry than it has in the past. You know, any time that an industry gets really, really, really, really, really good at like, um, you know, vertical SaaS, we know how to execute the crap out of that, right? Like we know exactly what to do. It doesn't require that much, it requires gumption and execution velocity and, you know, and, and all this. But like vertical SaaS I think is not the right model of how you would to- attack a problem that is sort of an AI native sale problem. Um, 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 like they, they, you know, 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 like a scrappy, uh, thing will be, uh, more important. One of the ways I put this is e- we've, uh, 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.

    6. LR

      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 get to work on my taste?"

    7. AK

      Taste with what I'm looking at this as, uh, differentiate from what the LM would have written if given the same prompt. How different, how distinctive is what you have to say? And, uh, 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 do, if you lean into something and you're doing something that sort of out there and nobody resonates with it, then like doesn't count. Like good taste is something that is individual and also compelling, uh, to others. And so find what things you say that resonate with other people and lean into that.

    8. LR

      I love that. Back to the web sim example. Uh, we're gonna link to this, but definitely play with web sim. I was interviewing Dylan Field at Figmaconfig and this was his ... Asked him like, "What's the number one thing you think people are gonna get more excited about in the future that you're playing with now?" 'Cause he's really good at identifying things that are-

    9. AK

      Mm-hmm.

    10. LR

      ... uh, gonna be bigger in the future. And we ... And that was his choice. And it's like 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.

    11. AK

      ... that's insane. I mean as in, and, 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-

    12. LR

      Hmm.

    13. AK

      ... sort of steer it based on the way it uses the context of the last few pages, it creates a coherent world-

    14. LR

      Hmm.

    15. AK

      ... that's coherent with the things that you have recently seen. And so you can steer it directly and, um, you can watch, you know, fascinating people that cover all kinds of wacky little techniques to get, generate, like generate a game for your kid that's on a specific type, like, you can do all kinds of stuff. And I'm not saying this really WebSim, WebSim to me is, uh, an in, 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, you know, take an existing playbook and like slap some AI

  6. 19:0223:04

    How AI makes us better as individuals

    1. AK

      on it, you know?

    2. LR

      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, it helps you collaborate better, and AI is the opposite. It makes you individually better. Can you talk about that insight?

    3. AK

      100%. Like the, I think this is one of the reasons there's a, there's a question right now, um, of like, okay, everyone's talking about AI and yet nobody is doing, like there's no interesting breakout successes obviously other than OpenAI topic obviously. So is it just all, is there any value being created? I think it's entirely possible. And Ethan Mollick, um, uh, who's a good friend who has an amazing blog, it's absolutely worth reading, um, a- has pointed out too that there's, uh, this is things that make individuals better in a, in a way they might not want to tell their ba- manager about, you know? Of like, "I can now do my job like twice as fast." Um, and if the organization sees that, they might go, "Wait a second. We have to pay him as much." They're like, "What if we got, if we could get rid of some extra people or something?" And so th- 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 generate 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 us seeing like the organ-, you know, seeing like the state, seeing like the organization. The organization almost won't see it or seek, sense it, and yet it could be adding significant value or doing, you know, just being used quite heavily. And I think this is one of the things that makes it, um, if everything is happening in the, the long tail of usage, then you could c- conclude, oh, it's not being used for anything in industry. But it's being used all over the place. I mean, I, I talk to Claude 20 times a day, uh, you know, I just have long conversations with it. I have tons of projects load- loaded up with all kinds of context and different topics. And, uh, I literally could not do the job I do now without having a conversation partner like Claude.

    4. LR

      Let me follow that thread real quick 'cause a lot of people are like, "Okay, people keep telling me I need to play with AI, got to ti- 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?

    5. AK

      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, I have a number of projects that just stuff as much of the bits and bobs into the context of the can, which is very helpful. And, uh, and then I just say, you know, just play with the re- give me 10 examples of that thing, or then critique these ones, or it kind of feels like this one's the best one to me. What, what works about this? Why is this one the best? Or I want to work at an angle now that has something about, you know, Helen Nissenbaum's concept of in- contextual integrity. How would I like layer that in? It's just think of it as having a extremely well-read but slightly naive friend who is willing to, will never make you feel dumb, and is willing to engage you in any particular topic you want to go down. So like, you know, when you talk to an expert, like a lawyer or a, 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 don't want, I'm not gonna spend $1000 to answer that question. Whereas if you can have that conversation, now this is not saying, you know, use it for legal advice, but it can allow you to explore through a problem domain and then later check it with, with experts and say, "I believe this is a coherent outcome or thing that should happen." And they can go, "Oh, yeah, that works." So I use LMs to help me, um, uh, it's like getting a, um, it's like an electric bike for idea spaces kind of. You can just cover so much more ground so much more quickly in them.

    6. LR

      I love that metaphor 'cause it builds on Steve Jobs' that computers-

    7. AK

      Mm-hmm.

    8. LR

      ... are a bicycle for the mind and-

    9. AK

      Yeah.

    10. LR

      ... that's really, uh, pr- beautiful way of thinking about it that LMs are like the bi- electric bicycle for the mind.

    11. AK

      I don't think that's-

    12. LR

      Oh, wow.

    13. AK

      ... my, it's someone else's that, um-

    14. LR

      Oh, okay.

    15. AK

      ... I, I don't know where it came from but, but part of my job is a collector of ideas, right?

    16. LR

      Mm-hmm.

    17. AK

      And so I try to put myself in the most in- interesting information streams with interesting people that I've found to have taste of, have a perspective on something. Maybe I'll be disagree with it, but they definitely have a coherent idea and then I just kind of allow myself to like, "Oh, that's a really good idea and let me build on that or let me," like these. So I don't even know where this, that particular one came, uh, by, I'm 95% sure that somebody else

  7. 23:0431:48

    Organizational kayfabe

    1. AK

      said that.

    2. LR

      (laughs) Okay.

    3. AK

      Said that. Yeah.

    4. LR

      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.

    5. AK

      Yeah.

    6. LR

      Talk about what this idea of kayfabe is on its own and then how this applies to organizations in your experience.

    7. AK

      So one thing I should, I should flag before we dive into any of this stuff, sometimes when people hear me talk about how organizations work in systems, they think I'm being cynical. And I, I want to be very clear, I'm hyper optimistic and I also believe that, um, the import- like one of the moral precepts is how 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." It's like, 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 the system can tweak and nudge it. So I just want to flag that b- before I dive into this. You know, the, this, I have this slime mold deck which has gotten a ton of, you know, traction over the years. And part of the reason for that is because it feels like, people tell me it feels like getting a big, like they think they're crazy and it feels like giving a big hug and 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, 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. Of these two options, this one is way cheaper and way more likely to succeed. So once you see these forces, you see them more clearly. 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 the, one of the defining forces within an organization, uh, any organization. So uh, kayfabe in the small is optimism, enthusiasm. When someone says, "We're gonna do this thing," and you say, "Yeah! We're gonna do that," even if we're like, "I think that thing isn't gonna work." If you say, "I don't think this thing is gonna work," everyone loses c- 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. The problem that you get is, as organizations get larger, um, imagine you are, you know, five lay- levels down or something and, and you have this, um, this project you're working on and you're trying to give a status update 'til you rolled up to leadership. And it's currently in yellow. And your manager asks and you know it's not gonna be presented to leadership and, and rolled up until next week. And it's yellow, but I've got my arms around the problem. I know how to fix it, I'm gonna go talk to Sarah, I think we have a solution. By the time this is reported up the chain, it's gonna be green. So if I make it yellow, there's a non-trivial chance that someone's gonna swoop down and say, "Well, what's going on? We have to have a review," and it will be way harder to fix. So I'm just gonna, eh, little white lie. It's green. This is a totally reasonable thing to do, it's a self-defensive thing to do. 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, uh, it can lead you to make very bad decisions. And if you as a, someone who sees this can see that, wait a second, the official strategy is definitely not gonna work, you're like, "I gotta, I gotta tell somebody. Like y- we're doing work that's going in a bad direction that's not gonna work." And you go and say, "Tell someone I think that this ... it's actually not gonna work for these reasons." And what someone will say to you, and this happens by the way. This is, I'm not sub-tweeting 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, then everybody, the whole thing will shatter. And we can't do anything. And so, help me fix it. Like don't, don't say the ground truth, just help nudge it and fix it." It's like, "That's a good point." Okay, so you help working on it, and then they realize, uh, you know, 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 up. It's just not good for anybody and it's getting worse." And so if you think you're gonna go and hit the ground truth button, before you do, you will be flying tackled to the ground by somebody and stabbed in the dark because you will destroy everything. And so it becomes, um, correct to, uh, 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, uh, this increasingly in the limit, it can be good to a point where the easiest way is if I, if I let go of this idea, uh, if I do, if I hold on to 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. And this is when organizations become zombies. And anyone individually you talk to behind the scenes will agree, this thing cannot possibly work that turns out that these things work this way, and yet the entire organization lumbers on. And this is a kind of death state for large organizations, and it happens all over the place in any number of, of different conditions. And this is one of the reasons it shows up, and uh, I think acknowledging that is an important way to help navigate and still make good, grounded things happen. Like 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 gonna 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 it.

    8. LR

      The, uh, 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, uh, 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.

    9. AK

      Uh, h- like disconfirming evidence hurts.

    10. LR

      Mm-hmm.

    11. AK

      And so, um, you won't, uh, you won't realize it 'cause it hurts and at any given moment it's like, "Oh, it's a distraction. I'm try- we're just trying to get this thing done." And so it's, it comes from a good place to not get it, but if you're busy, that's one of the reasons you need to take a step back. When you take a step back and you're a little bit calmer, you can absorb the disconfirming 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. And so this is one of the s- the, the reasons that large companies are radically different than smaller companies. And one of the traps that you can get into of, of not realizing this dynamic is happening, uh, and you can, you can make very bad decisions if you don't understand that is inherently what's happening. People say, "Oh, well, that's 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. 'Cause if you do, they're the person who, who decides, "Oh, this person's not really performing," or whatever. And that one little assymetry, that one little fact, in most cases does not matter, but that one little assymetry is what leads to 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, to change per se.

    12. LR

      I love your caveat at the beginning that continues to resonate in my head as you say this, like, you're not c- cynical about this sucks, it's more here's what I'm observing. We need to think about ways to get around this.

    13. AK

      Yeah. 'Cause I mean, I, I think so much pain and misery is caused by us being not acknowledging these fundamental, inescapable things. I can almost, it's almost impossible, like entropy is one of those things. Entropy emerges because there's more ways to go away from a point than towards a point is fundamentally like must be true in, in really any universe you can possibly imagine. And so if you're gonna fight entropy, like you're gonna lose at a certain point. It's like, if, 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 and I'm just 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, uh, and the person who's planting it enjoys planting it, so that opportunity cost really isn't that much 'cause they get energy from doing it. So who cares? Plant a bunch of these suckers, you know? If one of these grows into an oak tree, that's great. Don't try to analyze beforehand which seed is gonna 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. And people sometimes will see this as like, I've been called a nihilist before because they say, "Well, you're saying that, that you don't know the answer to the thing." And it's like, no, I'm saying I don't have to know the answer to the thing. If on a systemic basis I plant 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 gonna work.

  8. 31:4834:46

    Gardening vs. building

    1. AK

    2. LR

      That's a great segue to talking about this core idea that a- again informs a lot of the way you think, which is this idea of building versus gardening, uh, the magic of acorns. Talk about this general idea and then I wanna follow some threads.

    3. AK

      So much of the, 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 sort of direct or maybe give a little bit of extra energy to or, or curate over, and is, is a totally different mindset for it. So it's like a lead by gardening kind of vibe. I don't try to pick the things, uh, 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. And if you do this properly, it looks like magic. It looks like a thing, um, it looks like getting lucky, um, 'cause what you're doing is you're, 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 in- you know, interesting and transformative. And so if you're looking and finding these seeds that have the compounding potential, like if they work they would start working at an accelerating rate, then like, you don't have to know ahead of time. It's like, this is just, it's, to me this is, uh, I've been told that this is completely against all the advice (laughs) that people get, um, you know, building products nowadays, and, uh, but I think it's a very powerful approach that works in a lot of different contexts.

    4. LR

      Is there an example that you can give from either from something you worked on or something someone worked on that came emerged from this? 'Cause I think people hearing this might be like, "But I got to ship, 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, like, actually build."

    5. AK

      If, if there's an ecosystem approach, if there's something that if it works there will be... it'll sort of be self-accelerating. So okay, we're gonna do this thing. We aren't entirely sure it's gonna work, but if a developer writes a thing and somebody uses it, it'll attract more developers, attract more, more users, and this would grow on its own. Um, that, and it's cheap to do the little example of the thing. It's cheap to, like, build a little open source like tinkery 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 an incremental bit of unit each time that you find a signal that somebody's finding it useful and then you stop if you ever cease getting that, that, that information. It's like, 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, uh, they're, 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 with a, um, you know, where the power goes up with the number of users or, um, but it shows up in all kinds of problems that we don't normally apply it to.

  9. 34:4641:55

    Emergence-oriented thinking

    1. AK

    2. LR

      Along the same lines, you also advise people to think more, uh, emergence oriented versus top down. Kind of what you were just saying, but I think that's another really in- interesting way of thinking about the same idea. Create opportunities through emergence bottom up versus top down control.

    3. AK

      Yeah.

    4. LR

      Could you just ch- chat about that?

    5. AK

      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, that is hard about it, in my opinion, is you're gonna look like you aren't very serious. You're gonna look like a weirdo. You're gonna look like a kook, you know? And, uh, one of the downsides if, you know, 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 this thing and nothing interesting happens, no one can say you didn't work hard. But if you try doing this kind of designing for emergence and something amazing happens, even once it happens people go, "Ah, it was luck." I didn't- I- where was the miraculous moment where you, the heroic moment where you made that happen? So therefore you had nothing to do with it. And this was the biggest unlock in my career actually was when I stopped, when I got to, was promoted to director at Google and 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, like, 10X my impact for the organization 'cause I didn't have to worry about making it measurable specifically in a way that would show individual heroic effort. And I think that's the hardest part. And you have to have, like, typically what I would advise for, for PMs in 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?" This, if someone says this about your team, your team is on the verge of death. 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, like, of course that team should exist. I'm, I'm not even going to think about it. Of course they should.... but now, eh, once you do this you have, like, 30% of your extra time that you can plant all these seeds. You can find interesting little things or maybe a junior PM on the team has an idea you think is kind of silly, but they're really into it. And the reason... Thing, it could work out great actually if you tweak it like this, there is a potential. Like, I can, I can see how that could work. If that PM is gonna work on it 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 proactive over a year," say, "Go for it. Uh, here's my concerns. I w- well, uh, i- imagine this part might not work, but this part is really cool right here." And then if it works, if it doesn't work then they've stretched their agency, they've executed, they've, um, exercised their agency. They've learned, they've gotten stronger, they've gotten, um, they've grown. It has the upside if it turns out to actually work, uh, and worst case scenario, you know, they, the opportunity comes to do their thing that helped them grow and that they learned and they liked. So like, I don't know, don't try to force it. Don't try to stop it.

    6. LR

      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-

    7. AK

      Yeah.

    8. LR

      ... where your team's just hitting goals, moving metrics, and then while, with that cover fire you're kind of building the doomsday bomb inside, protected-

    9. AK

      (laughs) Yeah. Yeah.

    10. LR

      ... where no one's gonna come and stop you.

    11. AK

      Yeah. Yeah. Yeah. 'Cause see one of the hardest parts about an acorn when you plant it, is making sure a squirrel doesn't dig that fucker up, you know?

    12. LR

      (laughs)

    13. AK

      Like, it, there's so many things that can destroy it and just keeping it, allowing it some space and allowing it some time, uh, is, is the most important thing. And it's challenging to do, but that's why it's important as a, 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 protect, you know, to give your team the space to do this truly great work. Like, 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 the sum of its parts. That takes time, it takes effort, it's very difficult to make legible up, eh, uh, to the rest of the organization, but, like, that is where great things come from.

    14. LR

      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," 'cause every new idea is bad initially. And then-

    15. AK

      Yeah, it sucks. There's dad, they, like-

    16. LR

      Yeah.

    17. AK

      ... they're just, like, this ugly thing that, like, barely works or kind of like... But if, this is why I, my, 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 ... s- I try to find and steel 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 and I mentor them, I try with it within the first session or two, whenever I can sort of 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. And you know, 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 gonna stretch farther, and they're gonna respond to nudging feedback even better 'cause they know that you're not trying to tell them, "Be different." You're trying to tell them, "Be more," and you can, and now the nudges will feel less like a stop energy and more like a 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, I, I take from, eh, I assume that everyone I talk to, everyone I talk to is, uh, you know, is interesting, has seeds of greatness in them, even if they don't recognize necessarily where they are. Someone described to me actually this morning in one of my little, uh, nerd clubs I run about, um, that I help facilitate about treat everybody like the Buddha, I think is... I'm g- I'm messing this up, but, like, this notion of, like, imagine everyone you talk to is the Buddha, you know, Buddhist, uh, mindset, and how do you see and find that, those seeds of greatness, um, and treat everyone with re- respect intrinsically as an end in and of themselves. This is one of those things that you do to, like, be, like, 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 like one of those win-win-win-win-wins where, uh, 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.

    18. LR

      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. You can also access hundreds of pressure tested 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 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.

  10. 41:5545:15

    Slime molds and organizational structure

    1. LR

      Coming back to a phrase that you used earlier, uh, slime molds, I want to spend a little time here. So interestingly enough, uh, the first time I heard about you and what got me interested in your stuff is I did a, a newsletter post with the company Perplexity about how they build product. And as they were describing how they organized their team, the, the co-founders described they organize like slime mold, and he linked to your deck about slime molds. And I was like, "What the heck is this?" (laughs) Can you just briefly describe what you mean when you talk about slime molds and how that, and (laughs) how slime molds are related to the way companies are organized and how they should think of the organization?

    2. AK

      Yeah. So th- the main piece of the, uh, the slime mold deck is that, uh, the core dynamic that makes organizations hard to navigate as they get larger, even if you assume everybody's actively good at what they do, actively collaborative and actively hardworking, is this emergent force of coordination of finding the, like, subset of projects to work on and when everyone's super busy, that everyone agrees and commits to and actually works on together. And finding this coordination cost is in, uh, you know, grows kind of 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. If you're gonna fight it, uh, when we look at this is...... think of a company like a vehicle. When a company is very small, you can drive it, you can steer it like a, like a sports car. As a founder, you, you're allowed to steer. Everyone acknowledges you are allowed to steer. They've never got to see why he's steering it that way. So you, a founder can help navigate a, 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. So what I see a lot of things happen in large organizations is people just trying to ignore this fact. And uh, you know, when you drive, by the way, a car, uh, your vehicle like a big rig, when it is a big rig, people go, "Oh, it means go slow." No, no, no. It means pivot less. It means have a little bit more like, uh, you know, 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 un- ... so surprising things that you can still all reach the, like, product launch at the same time. 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 get the autonomy and, uh, you know, and, and strength at the bottom

    3. ... the downside is other people externally will look at it and go, "Well, that team and that team clearly didn't talk." And you'll say, "Yep." You know? (laughs) like you have to decide how bad it is for you. Apple has chosen the former. It is very important to them to have the illusion of perfect coherence in their products. It worked very well for them. They executed it marvelously. Any of those, it's like the exact opposite thing. Any of those, yeah, sure, there's like 15 different ways of doing everything. They clearly don't, those two 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. And so, uh, slime molds I think is like, uh, ignore, 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 gonna have a bad time. And if you embrace it, then you can start realizing slime molds are actually kind of amazing. They can find problem, solutions to problems you didn't even know you were searching for. So...

  11. 45:1547:05

    Identifying resonant ideas

    1. AK

      Uh, Alex, you have the best metaphors.

    2. (laughs)

    3. I don't know how you do this, but they're so evocative and, and correct.

    4. I, I can tell you the, the process I, I do if you're interested.

    5. Please. That would be incredible.

    6. Um, so I think by talking, I'm an external processor, I literally can't think if I'm not talking. And so I, I, uh, 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, uh, something that the person goes, "Ooh," or like, "Ooh," right, like they go, "Ah-ha!" That's a, a win. That's a mark that's a good one. Just randomly casting about until I find one. And then if a different person also has a similar response, if you have, 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, you know, uh, perspectives are the people who resonate with the thing you're saying? 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 a, a, a certain people who 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 you had people that are very different sub-graphs 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, uh, 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 you... I haven't done it this, during this chat, but in most conversations you will 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 and you keep on tightening it and seeing how, watching how it's responding and reframing with different people. It's really like, "Where'd you get these from?" It's like, "I don't know. I got like thousands and thousands and thousands of little examples or metaphors or whatever that stick." One of the be- benefits of metaphorical

  12. 47:0548:02

    The power of metaphors

    1. AK

      thinking is you connect nine of the ten dots and you allow the, you invite the, 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, if you connect all the ten dots and it's like, "Oh, that's against the official strategy," then you are instantly, you know, uh, a dangerous thing. Whereas if you leave one dot connected, people can go, connect the dot and go, "Oh my God, I think that applies to us." You're like, "Oh my God. What?" Like, "Yes, of course. That's why I picked that." So but to counteract this, because now it's less obvious to people that it's correct, you have to make the metaphor evocative and interesting. One of the reasons a 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 kind of inner, instantly subversive thing. I only know this after the fact of trying to figure out why did that deck get so much attention for, uh, you know, of all the things I've written.

    2. It also is all emojis, basically, which is not, uh, how you often read a deck. Uh, it's very beautifully made.

  13. 48:0252:30

    Strategy salons and nerd clubs

    1. AK

      I, I love that you've t- 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?

    2. So these I also have called now like nerd clubs, and these are my secret weapon. And I have a blog post I was, started writing right before my second kid was born, and I, and then he was born three weeks early and I just lost the plot. And now it's like a, you know, 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, as I strengthened some of the techniques I'd used in open source community organizing. And, you know, the, the, the situation was I was just joined a new team at Google, had been there for many years, and there was like, at the time, 12 different groups working on 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 like, "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, uh, pairwise executive reviews on this very complex, ambiguous, open-ended problem, you would get really expensive pageantry that would obscure more than it clarified. So what I did was I created a secret group that I called Navel Gazers, was the original one, and it, I wanted people when they hear about it, I want people when they, they go like, "That sounds like a club for nerds." 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 then you get only a, kind of, positive, you know, um, yes end kind of energy. So then within these groups you, uh, you say, you set the norms very explicitly and say, "This is a collaborative debate environment. This is only yes end. If somebody says a thing in this group that is optional and secret and completely off to 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, right? Because nothing's gonna happen. Not that we're deciding anything interesting or important here. 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. Huh. I would never would have 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. You're like, "Ah, how can you possibly get rigorous thinking with yes end?" 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 things, 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. And the third thing you do is you dribble in new perspectives. So every, you know, one to three a week. If you put in lots of new perspectives all at once, the norms can all scramble. If you have one, you know, 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?" Like, eh, like you want to minimize the chance that happens. But second door, barely more importantly, you want to have as, uh, people with as different a perspective as possible added into the group. And so what you're doing, this is what, uh, Ken Stanley might call, for example, novelty search. You're novelty searching through the different perspectives in the overall, um, thing. 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 game-changing insights for the surrounding context because you're searching through these ideas in a low-stakes environment where the ideas that lots of people build on, they go, "Oh, you should write that down." And so this is like an idea lab, what Tim Urban would call an idea lab, and, uh, 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. And so, uh, 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 have, uh, to experiment and try out different half-formed ideas and build on them and be inspired by other people. And, uh, and that is one of my secrets, uh, my sort of strategy secrets that I've been doing now for, probably 10 years ago is when the first one started. And there's now, I, I can count like eight or nine I've, I've started over the years. Some of them emerged, 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.

    3. LR

      And I love it's an, uh, 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

  14. 52:3055:59

    Building and sustaining communities

    1. LR

      here." If someone wanted to set this up within their company or within friends, any advice? What are some kind of constraints and ways of setting it up for success?

    2. AK

      Communities are all about momentum. You want to have a, a space too small, a time too short. Like, if you have a big cavernous space with 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 gonna be actively engaged. So maybe there's four of you that already talk over lunch, you talk about whatever topic and it's always really interesting and generative. Cool, get that group together into a thing. And then a- incrementally add people who you think are gonna like that already as it currently exists. And then you need to feed it. So you want to make sure that it never dies and the community that has only one person talking is, uh, a community with no people talking is definitely dead. A community with one person talking is already dead and you don't realize it yet. And, uh, so you're trying to maximize the chance that there's an interesting conversation even when you as the kind of facilitator are not there. This takes some active policing by the active, 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 like maybe next time add 'I wonder' to the front of that statement," or whatever. The other thing that you do is when people, um, reach out to you on Ping and they go, "Hey, let's think about this, 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." You get a 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, um, norm in the community. And it's not a secret, it's not like a, you're not like, 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. Uh, the other thing you do is once a, once a week or so, you need to, 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 you're talking to other people, you say, "You know, I wonder, we should have like a live conversation every so often, right? Like, the chats were so fun, but like..." And the person goes, "I, I, yes." "Would you come if I did one?" "Oh, yeah, I would." "Okay, great." So now you say, "Hey, a few of us are talking, we're just gonna do an experiment. We're gonna have an hour long conversation over lunch on Wednesday. Um, anyone in the group is free to come." And then what you do is you make sure it is always has quorum because if it doesn't have quorum, then the thing, you know, it looks like the community is dead. And then what you do is you d- send FOMO stuff afterwards. So then you say, "Here's my notes from the thing," or, "Thanks, you know, Sarah, Jeff, blah, blah, blah, for an amazing conversation. I, I thought the insight about blah, blah, blah was so ridiculously amazing." So you want people who were in the group but didn't come to feel like they missed out and to come to the next one. And so you're constantly creating these kinds of, like, vibes to, to, uh, uh, do it. You, you can't do it if you don't have somebody with a lot of energy. I'm typically the kind of like seed, seed crystal for a lot of the groups I'm in, um, to start them off because I have, like, a lot of energy (laughs) and I like, you know, I like anything that people have to say that I think is open-minded or interesting, I like building on and yes ending, and that kind of gives it the sort of foundation that can grow. But like, look for the people who already roughly want it. Don't try to convince if- don't try to convince somebody who doesn't want it to want it. They will not. They will ruin the whole thing.

    3. LR

      I 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.

    4. AK

      I, I have. It's a, it's a long essay and-

    5. LR

      Okay.

    6. AK

      ... um, and I, yes, it's just not... You can see it in Bits and Bobs. Like if you asked, if you gave the Bits and Bobs to Claude and said, "Please write a thing about nerd clubs" and-

    7. LR

      Yeah.

    8. AK

      ... an essay in this style, it would do it.

    9. LR

      Okay.

    10. AK

      Because a lot of the pieces are in there.

    11. LR

      Good.

    12. AK

      It's just not factored out.

    13. LR

      I see you writing something down right now, which tells me you just articulated something in a new way that you want to say.

    14. AK

      Yeah. That's right, that's right.

  15. 55:591:01:04

    Productivity hacks and self-control

    1. LR

      So 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 on how to be more, a little more productive?

    2. AK

      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 like, I find every time you, you start a task, there's an activation energy, especially if that's what 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 and get small things that are extremely easy to knock out-

    3. LR

      (laughs)

    4. AK

      ... in like 10 seconds of effort, and then you do one that takes 30 seconds of effort, and then you do one that takes, you know, a longer bit of effort. But if you give it too much space, it's too, it's harder to do. So like, you almost want to find, okay, listen, I got 10 minutes. I gotta do this thing where I figure out how to add, uh, you know, do this thing in Gusto that I've been p- putting off. Like 10 minutes should be enough time to do it and structure it so like, okay, right now is the only time I have to do this right, uh, to do it. And, you know, another tr- trick is, um, I- I use as like a, I have... One of my original me- Medium essays actually, one of the original public ones is about sometimes rules, uh, always rules are better than sometimes rules for self-control. And so if you're going on a diet and you're like, "I'm going to eat, uh, only go- I'm never going to eat, uh, you know, I'm going to skip lunch every day." Like holy, you're gonna, you'll have a fault flat on that at some point. Like maybe there'll be a day with a big executive review, like 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 you can do, I will not, uh, have a dessert, uh, unless it is, uh, 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 gonna like... It's a very clear black and white rule that you can hold on forever. So like for example, since the pandemic started, I've done a Peloton workout every single day, um, since the pandemic started.

    5. LR

      Wow.

    6. AK

      And, uh, once I did start going back into the office, um, if I had to commute into the office, I would sometimes do a, you know, a meditation to check the box for that. But if I'm not commuting, I've done a full program. I'm not like deathly sick. I've done a full workout since then. And the idea of each day of like, 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 sort of streak, uh, that makes it harder and harder to get out of it. And in some ways it kind of, of course, you can tort yourself in an unproductive way, like at a certain point, uh, maybe you should stop that streak. But, um, but I think those kinds of structuring help you get the things done you need to, you want to get done, you know?

    7. LR

      It's like the Seinfeld, uh, trick of productivity where you just cross, you just keep track of how many days in a row you've done something essentially.

    8. AK

      Yeah. Yeah. Exactly.

    9. LR

      Love it.

    10. AK

      And I, I think people, people don't give those kinds of tactics enough credit because-

    11. LR

      Mm-hmm.

    12. AK

      ... there's lots of little social tricks to yourself and others. This is, uh, when you have other people who are depending on you for something and will know that you didn't do the thing, that works so much better. So like just little tricks like this-

    13. LR

      Yeah.

    14. AK

      ... that help you get, um, be wildly more productive.

    15. LR

      I actually want to go back a little bit. Uh, I'm curious to what you wrote down when we were chatting earlier that you thought was a good, uh, articulation if you're able to share, if it's interesting.

    16. AK

      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 like maybe onto something. So I wrote down a community with zero people speaking is dead and a community with-

    17. LR

      Mm-hmm.

    18. AK

      ... one person speaking is, uh, doesn't yet realize it's dead. That's what I wrote down.

    19. LR

      So fun. I love this practice that you have.

    20. AK

      (laughs)

    21. LR

      (laughs)

    22. AK

      I, I, by the way, the reason I can do it, I can type insanely quickly. And, uh, in undergrad I wrote my thesis on the emergent power dynamics in Wikipedia's user community. And I did, um, 150 hours of interviews with gran- with, um, different editors in Wikipedia and I transcribed them myself. And so I got really, really, really good at like I can just pipe an idea straight into my fingertips and still listen to other stuff. So like that's another superpower, is I'm 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, you know, within the next day or two into something that's more stable.

    23. LR

      Uh, is there a way you built this other than... Was it just you did it and you had to do it and you just like figured out how to move fast?

    24. AK

      I just realized later that like I could take really good-

    25. LR

      (laughs) Okay.

    26. AK

      ... really fast... I could just pipe it straight through to my fingers and it, it worked and I don't know. I don't know if... And like could... If I hadn't written my thesis, would I have discovered that? I don't know.

    27. LR

      (laughs) I feel like everything, uh, you do is like on s- super speed, like the way you think, the way you write, get stuff done. I, there's a lot-

    28. AK

      I wa- I just realized when, when, when-

    29. LR

      ... a lot of compute.

    30. AK

      ... you're feeling productive, you're unstoppable. And so just f- how can you be in your flow state as much as possible?

  16. 1:01:041:07:52

    Life philosophy and personal insights

    1. AK

      kinds of, when I have the moment. I also find that like often if I have an idea and like I just, I'm itching to write it down, if I can write it down in 30 minutes and get a very rough

    2. NA

      (fart noise)

    3. AK

      ... of it in one place, now it's easier to clean it up later. But like that first act of creation, I do it whenever the muse hits, uh, because it's 10 million times... If it's like, "Oh, I'll write that idea down later," you keep on delaying it, delaying it. Now it's a month later and like, "What was the idea? Like how does that work again?" And it's gone. And so I just try to capture the interesting insights. It's like a butterfly collector. Like the butterflies are going by, I try to collect them and put them in my collection.... uh, as quickly as possible.

    4. LR

      Or garden, as one might describe it.

    5. AK

      Yeah. Yeah. Yeah.

    6. LR

      (laughs) Uh, this touches on a quote I wanted to talk to you about. It's, uh, I think you describe it as your life philosophy. "Do things that give you energy that you are proud of."

    7. AK

      Yep.

    8. LR

      Talk- talk about that.

    9. AK

      So to me it's- 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- on that topic and can go for much longer. So finding the subset of things that align with, that you, that give you energy then just, it's kind of like infinite energy. It's just, it's like negative opportunity cost because it energizes you more than the sort of opportunity cost or the time to like go spend on other things. And two, there are ways to, um, uh, there are ways to give yourself energy like for example playing an addictive video game or is there any kind of mind-altering substance that might give you that kind of like, "Aah, this gives me energy." Those are not things that, like that's, 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. 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, you know, uh, it's gonna suck, but then once I do it, it'll be fine." And like then you find yourself doing it again and again and again and again. And before you know it, you've like lost who you want to be and you're now kind of a husk of yourself. And so I think those two comp- 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're (laughs) actively proud of. Um, you know, and that help make sure you don't take a bunch of shortcuts.

Episode duration: 1:24:37

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