How To Navigate Your Career | Elad Gil | Ep. 6

[00:00] And I actually don't believe in lifelong learning. I believe in lifelong doing, right? Everybody talks about lifelong learning, and I'm going to go learn this thing before I go do it. Of course, just go fucking do it. That's how you learn things. But again, that's how I view the world. And it's back to your point on assuming there aren't obstacles in the way or there aren't that many limits. Part of that is just that assumption that I can just go do stuff. All right. Well, I'm very excited to do this with you, Alad. Thanks for making the time. And before we get started, I'm going to try a joke because I just shared it with you, and you looked at me deadpan, but I thought it was funny, which is that we're at Sarah [00:30] and I said this episode was brought to you by Sarah Guoga. I think it's fantastic. I thought it was funnier than you thought it was. Thank you, Sarah. Hopefully the viewers will like it a little bit. [00:37] Today we're going to talk about a bunch of stuff. The main thing is kind of around the idea of careers and how you think people can navigate their own. Obviously, to some extent, you're going to be the case study as we talk about some of this stuff, but that's kind of where I want to go. And where I want to start is... [00:53] kind of around the mindset that at least I perceive in you, which is that you seem to navigate the world in somewhat of like an anything is possible, there aren't boundaries type of way where any person can be met, where any company can be built, where any deal can get done. I don't know if we've ever talked about this explicitly, but I've just observed over the years that that seems to be kind of how you operate. And I'm curious if that mindset was... [01:16] always there? Did you cultivate it over time? Because it seems very valuable. I think it all started when I saw the movie Limitless. Sorry, it's off to a bad start. No, it's good. Yeah, you know, it's kind of interesting. I feel like, I don't know if it was instilled by one of my parents or something, but in general, I had a family that, you know, on both sides, there were multiple generations of immigrants, etc. And you got to just show up in a country and figure things out. And so a lot of that perspective, I think, kind of transferred over in terms of,

[01:46] case that could happen or what's the worst thing that could happen. And I think a lot of barriers that people kind of set up for themselves mentally or that they perceive to be existing societally actually don't really exist. And so there's a very strong attitude in my family of life is kind of [02:01] pick up the phone and try calling someone. And what's the worst thing that could happen? They just don't answer the phone. And so it's a little bit of that mindset, I think. What are the other ingredients to the mindset? So the one that you just mentioned is clearly one where you're not afraid of rejection and where you're like, it's okay if somebody says no or I don't get that thing. What are other ingredients, do you think, to the mindset? [02:21] Yeah, I think it's a little bit of almost shamelessness around certain things. Like, you just don't sweat it. It's the old thing where you learn a foreign language more easily, if you're willing to sound like an idiot in the foreign language. [02:33] Or it's the willingness to ask a really dumb question that turns out to be a good question. [02:37] There's a couple people I've met over time who I think are really exceptional where they start asking these really basic questions and your first reaction is like, "Ugh, why are they asking this dumb thing?" and then they keep drilling and they suddenly get to the essence of the thing in a way that you didn't expect. [02:49] And that's almost that shamelessness of being willing to ask something that most people would worry about. And do I look dumb? And am I really asking the right thing? And how will I be perceived? And so I think part of it is concern about perception. I think part of it is just the willingness to take on a little bit of risk. And I think part of it, honestly, is just facing the reality of the situation. Truly, what is the worst thing that could happen in certain situations? It's like nothing. Nothing will happen. How have you thought about that risk question?

[03:15] about, you know, is there actually risk when you take risk or is the risk what it looks like? Maybe it's a better way to say it. Because like, you know, if you think about it as like a repeated game, it's actually not that risky. But I'm curious, like, what do you think is the blocker some people have when they're like afraid of taking risks professionally? It depends how you define risk. It could be starting a company, it could be changing roles, it could be asking for a promotion, it could be all sorts of things. You know, and I do think there's different ways that people approach this. And some of those things break down on people's backgrounds, [03:45] Sometimes it's more oriented around gender. I remember talking to somebody who was running a big podcast and she said that [03:50] She would constantly get panked by male guests. [03:52] suggesting themselves and then she'd reach out to women to be on it and they say well i'm not sure that i have anything interesting to say so i think there's also different angles on [04:01] just how people perceive themselves, how people think about the world. And I think they break down along all sorts of backgrounds and all sorts of lines. And obviously, there's different types of people in different orientations that do everything, right? It's not meant to be an over-interpretation, but I do think there are characteristics that just drive behavior as well. As you've sort of navigated through your career, [04:19] You've obviously built companies. You became an angel investor. You've become an extremely successful independent investor institutionally. Have you built towards certain outcomes? Have you been like, I want to become X, and so to get there, I'm going to do A, B, and C? Or in a given year, it's January 1st, and you're like, okay, this year, this is what seems smartest. I'm just going to do that and see where it goes.

[04:49] In evolution, there's this idea of punctuated equilibrium. You have a bunch of stuff happen, and then it kind of solidifies for a while and gets boring, and then a bunch of stuff happens. And so... [04:57] at least in certain evolutionary terms, it seems like there's explosion of diversity and then it consolidates. And I feel like that sometimes happens in careers. And that's definitely happened in my career path where there'll be moments in time where I'm planning ahead. I'm running a company. The company needs to have a financial plan and a hiring plan and a product plan and everything else. You need roadmaps. And then other times it's super reactive. I started investing effectively by accident when friends of mine started asking me to invest in their companies because I'm just helping them. And years ago, 14 years ago, whenever I made my first investment, I never would have thought, oh, now I'd be running a multi-stage investment practice in [05:27] Thank you. [05:27] And so it happened a little bit more by happenstance. Now, arguably, I should have thought ahead on that and I should have planned it and started earlier and all sorts of things. So I think maybe the ad hoc or semi ad hoc approach I took sometimes doesn't work. But I think the flip side of it is the thing it does do is optimize for market need. Right. If you're sort of reactive to the market in the moment, then that's when you can actually do really interesting things relative to it. And there's founder market need in terms of startups and what they need help with. Or it could be, you know, certain startups that you're going to build or whatever, maybe. [05:57] available to you. More than most people who have gotten to where you are, I could imagine next year you doing multiple things in a way that I think is hard [06:09] to see other... [06:10] people or groups that are more solidified. Do you actively cultivate optionality in certain ways? Do you want to be in a place where you're like, if I want to spend my time incubating or doing growth investments? I've definitely tried to set up things in a flexible way up front. And so that was very thoughtful. That took a lot of pre-planning in terms of how do I set things up that I have a lot of flexibility in terms of what I actually focused on, how I spend time day to day.

[06:40] if I allow that sort of organic path to happen, I end up with better outcomes. And I also enjoy them more, right? I want to work on things that I find interesting. I really love technology. I love the impact of technology. I'm very techno-optimistic. And so I want to work on things that I think will be important to the world. And then I want to work on things that I just find really viscerally interesting. And sometimes those are the same thing. And sometimes they turn out to be different things. You know, one thing I've been thinking about recently is how do you gain longevity in Silicon Valley? Because if you look at it, most people spin out every five to seven years. There'll [07:10] suddenly a subset of them just move away. Or somebody who's really relevant for a couple of years suddenly becomes irrelevant. [07:16] And so I started wondering, like, what are what are approaches to having relevance over time in a very dynamic, fast changing environment like tech? And I feel like there's two or three paths. I mean, one path is obviously you start a platform and you stick with it. [07:26] You're running a major company, you've started a major investment firm, whatever it is, and then you tend to have a longer arc because of that platform. And so that's sort of one form of it. There's also people who every couple of years start or do something really interesting or new. [07:40] You could argue to some extent that's Elon Musk who has both of them. He has the platforms as well as the new stuff ongoing. It could be Peter Thiel. He doesn't move away from it, I guess. Yeah, he keeps adding. Patrick from Stripe started ARC, which is a biotech institute, which is super interesting. So you start to see these people who over a decade or two start accumulating a portfolio of super interesting things they've done, often in different fields. And so that's one way people have relevancy. Another one is by staying at the cutting edge of technology or the cutting edge of startups or the cutting edge of what. And so there's a few different ways that people do it.

[08:10] new [08:11] when you either replace or add something new, it lets you go back to a beginner's mindset more often. And it like lets you sort of just like scratch more itches. And I do think it gets hard to become great at things when you lose engagement on them. And so staying engaged seems like a big part of longevity. I think that's a big thing. But I think also... [08:28] I think the set of characteristics that I've noticed in people who tend to have these long arcs, and I don't know if it's correct, right? This is all kind of early hypothetical stuff that I've been thinking about, but I haven't really vetted. And it's very early on. But one is most of the people seem to be reasonably polymathic. They actually tend to go deep on multiple things quite early on in their life. So it isn't something they pick up later where every end years they decide to go deep. It's like they're always going deep on things. And they happen to have one core thrust to their career, but then they continue to have these [08:58] to standalone things for them. The second is they tend to be driven more by impact or interestingness than by status or money. Because I feel like people who are driven by money eventually get really unhappy. [09:10] they hit a certain level of wealth and they're like, "Now what do I do?" You know? And obviously, some of them keep going, but you see it often in the sort of how that translates into [09:18] satisfaction of that person. So it's like, what is the driver is sort of the second characteristic. Third characteristic is many, but not all had success at a young age. [09:28] I think Marc had recently done amazing things over a very long arc. He was on the cover of Time magazine when he was 21, 22, 23 with Netscape. So amazing set of things that he's done over time as an example. They have this characteristic of staying interested in being

[09:45] relevant and part of the future. And, you know, these are the people that I think compound over 20, 30 years, and they just keep doing interesting things over and over again. There's a bunch I want to go into from that. But can we talk maybe first about how people should choose, let's say, you know, you're early in your career, or even not extremely early in your career, and you're thinking about where to go? You know, you just talked about like money and status or like not the prize to fight for. And... [10:09] What we'd probably both say is those will come as byproducts of doing other things, but that's not the way to get there, actually. How do you think somebody should be optimizing when they're thinking about, I'm not exactly sure what I should be doing. I either just graduated or I want to make a change or whatever. What goes into the calculus? No, that's fair. Well, I think there's almost like four or five different types of careers you could pursue. Yeah. [10:28] But before we get into that, I actually think Naval has a really good framework on this where [10:33] In the 90s, John Doerr was sort of a legendary investor. He invested in Amazon and Google and all these great companies, Netscape, I think. [10:43] And he used to have this mercenary versus missionary framework. He'd ask you, "Are you a mercenary or missionary?" And of course you had to say, "I'm a missionary." How could you possibly say you're a mercenary? [10:51] And Naval has this better framework, I feel, which is like he says, look, early in your career, you have to be at least partially mercenary. Right. And a lot of people early on in their career, they're like, if I only make it to X. [11:01] If I made a couple hundred K, I'd be so happy in life. Or if I made whatever. You need a little bit of that mercenary hunger. Otherwise, you're just not going to be driven in certain ways. You won't be scrappy enough. And you might be with interestingness or other things driving you. But you need some characteristic of I need to win. [11:15] in an aggressive way. Actually, that's one of the other characteristics that people compound over time. They're aggressive or competitive in some form or another. Are you saying that, just to click on it, when you're young, it's more important to have the mercenary thing than later on?

[11:29] Most of the young people were successful or at least partially mercenary early, however you want to interpret mercenary as a word. Once you're successful, if you're not missionary, you're a zero sum person. Nobody wants to work with you. You're terrible. And so you make a transition in your life. And then Naval adds a third component, which is later in life, you become an artist, right? You do it for the love of the craft. [11:49] And those are the people I think who sustain, right? Who can go through those transitions of I'm a little bit more mercenary. I just want to make it somehow. I'm missionary now. I want to do things for important reasons. And obviously these things blend, right? Nobody's 100% in any direction. And then later in life, you're like, I'm doing it for the art. I'm doing it for the craft, right? And I think that's a great framework, right? It is an interesting framework. I've never thought, you know, it's funny because if you hadn't just explained that and you asked me to intuitively react, I would have said you should be missionary at first. You know, like the sort of like learn then earn kind of thing you hear. [12:19] about all these really impressive people in their 20s, they were working like crazy. And a lot of that was driven by like, you know, you just want to make it. Yeah, there's some ego, which is not a bad thing. There's some like drive to like prove yourself. There's some of these other things. And maybe it's not just money, but it is there's something personal about it. Yeah. And I actually don't believe in lifelong learning. I believe in lifelong doing right. Everybody talks about lifelong learning. And I'm going to go learn this thing before I go do it. Of course, just go fucking do it. That's how you learn things. Yeah. But again, that's how I view the world. And it's back

[12:49] any limits, part of that is just that assumption that I can just go do stuff. I don't have to learn it first. I'll learn it on the way or I'll pick it up if I can. There are some things obviously that are really hard to pick up. I couldn't go and do advanced mathematics right now. But there are other things where I think I can just go pick them up. Then I think separate from that, you asked, "Well, how do you think about your career?" I think there's four or five different types of careers. [13:08] founder career. Am I going to start a company or not? There's joining a company, [13:13] either with the goal of starting something later, being an executive, being IC. There's the IC path, there's executive path, there's the investor path, there's a service provider path, right? There's all these different things you could do in tech, for example. Within the investor path, would you delineate somewhat between like working at like a big platform versus like something more like what you're doing or angels or things like that? Or do you think it all ends up looking kind of like the same bucket? It depends on if the goal is to be an investor, then I think those things mesh or they merge more, which I think is different from, hey, I'll do it for a little bit to learn about XYZ. [13:42] I think for most people, the path is you join something, right? If everybody was a founder, we'd have no productivity in society. That's true. And so you need more joiners than initiators. And for the people who join something, who join a startup young, I think there's four or five characteristics you should care about. One is where is it? And I think you should go to a cluster, right? And so for AI, the cluster is the Bay Area. I think 80 or 90% of all AI market cap is in the

[14:12] Obviously, if you're going into – [14:14] Acting or directing you go to Hollywood, right? It's kind of funny tech is the only industry where people say oh you could do it from anywhere and therefore you don't have to go Silicon Valley and [14:21] But if somebody came to you and said, I really want to be an actor, I'm going to move to Austin. They'd be like, what are you talking about? Yeah, I think the same. [14:28] I'm going to be a politician in Omaha. Yeah, exactly. What do you think? Yeah, exactly. It's great. It's a great idea if you want to do local politics. And so it's the same thing, right? So whatever you want to do, go to the cluster. That's where you're going to have density of other young, hungry people who want to do the same thing in the same industry. That's where you make your initial connections. You build your cohort. You get exposed to the best in the world at the thing. You learn the craft, et cetera. You do the craft. So one is, where are you? Two is, what market are you in? [14:54] And going into a bad market can be devastating for your career unless you leave it quickly. An example of that is I moved out to Silicon Valley as the dot-com wave was collapsing and I joined a telecom equipment company. And that used to be a very hot sector. [15:07] And I eventually left the company. I got laid off in the third round of layoffs as it was sort of collapsing. [15:12] Everybody who stayed in telecom equipment had a terrible career that I knew from that era. Everybody who went into other industries did well. And so really that choice of market was a huge pivot point. And so the second question after geographic location is what market are you in? It's almost like market location. [15:29] Third is which company do you join in the market? Is it a marquee company or not? Is it a brand? What sort of network is there, et cetera? And if I was optimizing for company choice, [15:37] I would look for something that's growing rapidly based on some clear metric. The metric could be revenue. It could be users. It needs to be something solid with high retention, whatever it is, because growth allows you to have a great career.

[15:48] If a company goes from 50 to 500 people, that's way better than joining a company that goes from 50 to 60. Because when it goes from 50 to 500, as employee 50, you know everybody. You're trusted by everybody. As the company grows, you get more and more opportunities. Just to stick there, because I think that's one of the most important things. I feel like that's the kind of thing that most people intuitively know or have heard, but then they get tricked out of it somehow anyway. How do people get tricked on that, and how do you avoid it? It seems like if you just had to pick one thing, it would just be pick that. Yeah, pick the thing that's growing in a good market. [16:18] People don't pick that all the time. So like, why do you think that is? [16:21] Well, I think sometimes they are getting attracted to a title or a scope or something like that that seems... [16:27] more appealing. Like I think people have a hard time going from, I used to be a director and now you're making me a manager when this other place can make me a VP. I think that's, [16:34] I think comp is hard for people, sometimes for good reason. I think sometimes people are just like, "I really like my manager that I'd have at this company even though it's not growing fast." And I think maybe what's being missed there is you're like, at the company where you didn't like your manager as much, probably your manager is going to change four times anyway and you might like one of those people. Yeah, I think that's all true. I think after the choice of a high growth company, I make sure that it's in a very strong network. Because Silicon Valley, or honestly every industry moves and clicks. [17:02] And people work together over and over again if they like each other. And if you're at a successful network, it branches out and then you have all these opportunities. It's kind of like the PayPal mafia. Early Google ended up being the COOs at all these different companies, as well as founders of companies like Instagram and Pinterest and other companies. How do you pick that? Like, how do you find where there's going to be a good network? You can just look at the characteristics of the people and kind of I think you get a vibe. Yeah. I think people often ask me, what's the biggest determinant of company culture? And I say winning.

[17:32] the high performance teams how quick are they following up on things like how aggressive are they how well do they ship like there's those external cues and there's internal cues of just like um what is the degree of stuff these people have done at [17:45] you know, in their prior careers or at young ages or however you want to. I think this is so important because... [17:50] You can't. [17:51] You can't remake these networks later. The people that you grow up with are the genuine relationship that exists later on. And I feel like there's no replacement for that. Yeah, but I think there's like 10, 15 years to do that. You know what I mean? I totally agree with it. I think you have a few shots, but you don't have infinite shots. You have a couple of those. And once you fall into one of those good networks, those people tend to go to all the best companies next. And so you get pulled into all the best stuff or you angel invest in them or whatever it may be. [18:21] company, I'd go to one with a great network. And then after that, there's comp and role and all the stuff you mentioned that people get distracted by. And I don't think that matters. [18:28] I think that stuff tends to self-fulfill by joining something that works really well. And so often people get misled by, "Oh, you're getting 10 times more equity." [18:37] But it's in something crappy, so who cares? Like, that thing won't work at all. [18:40] And so it's worthless on a relative basis. So I think people misunderstand compensation as well, particularly in startups, or you get way more cash, but who cares that things are going to not work. And then you've killed that amazing network you would have had as the alternative, right? The opportunity cost, it's almost like opportunity costs on market and network, is what you should be focused on. Right. It's like you accepted $20,000 to have a much worse lifelong network or something. Correct. Yeah, exactly. It's a really poor trade. Connecting this back to you a little bit and your own network, which, you know, we've joked about

[19:10] incredibly strong and I think it's very authentic and you have these relationships with people who are unbelievably impressive and you've gotten to that in ways that look to me like a [19:22] natural and authentic. I want to ask you a little bit about how you've gotten to that. Like, was it a function of just doing interesting stuff over and over? Was it about, you know, you meeting people and then you meet their friends and they're impressive? Like, how is it if you have to sort of inspect it, which I know you don't love to do, but if you had to inspect your own network progression, like, [19:43] How has that happened? Yeah, I mean, I think we have very different perceptions of this. We were talking about this earlier. Like, I think I know a lot of people that I feel have a much broader, deeper set of relationships or whatever. I have a couple. [19:54] You know, fundamentally, I've noticed that... [19:58] certain groups of people almost seem to self-assemble in different industries over time. It's often odd how early some of these folks meet each other. There's one really well-known founder, who I think is one of the most successful people of his generation. He was telling me a couple of weeks ago that [20:13] All the people that ended up being the most successful people he knew in Silicon Valley, he all met in his first six months out here. [20:20] before anybody knew who he was. He was just some random guy who showed up [20:24] He just graduated college and suddenly had this huge network of other young, really great people who eventually did huge things. [20:31] And so I think it's almost like like recognizes like or people self-aggregate. I'm not putting myself in this bucket. I'm just saying I've observed that. [20:38] you almost see the self-assembly of people over time. And a reasonably small number of people end up all knowing each other. And then a reasonably small number of people end up driving a lot of the big changes. Yes. And I think that's true in every field. I think if you look in biology, maybe there's a dozen biologists in each field that really matter, with the exception of some really big fields like cancer, where then you do it by subspecialty or whatever it may be. But you look at certain aspects of...

[21:03] I don't know what stem cell biology, it's going to be like 20 people that everybody knows that matters. It's really interesting to me when, you know, I hear from you that, you know, you're like, oh, I, you know, I haven't done so much or I don't have that network. And I think to most people, including me, it's like where you are is very aspirational. And I'm wondering, is part of the story of you that you've always, you know, you're thinking about there is always a bigger fish and how do I keep going? And that's part of what drives it all. Like, is that a thing about you? [21:33] I feel like... [21:35] I am continuously missing the bar. And I don't mean that in a bad way. Like I'm proud of some of the things I've done. And, you know, I'm happy that I started color because that helped save a bunch of lives. And, you know, there's a bunch of things that I'm very happy I did over time. [21:48] But I do think that there's so much more to be done, right? And so it's a little bit of the... [21:52] How do you maximize the impact you're having in your minimal time on the planet? You know, how do you judge yourself relative to what you think may be possible? Yeah. [22:02] What are some of the flavors of things that you haven't accomplished yet that you would like really hope you accomplish? Yeah, I mean, there's two or three things. To put that aside for one second, one of the things that I found really interesting is a friend of mine said, [22:13] is on one or two prominent boards. [22:16] And he feels like the existence of Elon Musk has been hugely empowering for him. [22:21] Because he can go to these really important CEOs and say, look at what Elon Musk is doing. And they suddenly get re-motivated. You know, they've been running a company for 10, 15 years. And so there are some people who have had, I think, really outsized impact who maybe won 100 or multi-hundred year sort of talents. And obviously, that's really rare because it's definitely once in a very rare period. But, you know, there's a lot of things left to do. And I think there's almost like three or four levels that people often talk about, right? I used to spend a lot of time in India doing yoga and stuff like that, which sounds very cheesy.

[22:51] out loud, but I really enjoyed it while I did it. And some of the discourse or discussion was, you know, throughout your life, you're moving through different rings of importance, influence, focus, whatever. So early in your life, [23:02] It's about yourself and your studies and your early career. And then a little bit later in your life, it's about your family because you have kids and you focus on that. And then it becomes about your society. And then very late in life, you go off to a cave and meditate and you become a sadhu and you shut off the world. Throughout your life, you mix these different poor things. [23:19] between... [23:22] yourself, your work, your family, your society, and your... [23:25] you know, religion or whatever other thing you have. So maybe that's five things. What I've been thinking about a little bit more lately is, and I honestly, I've always thought about like, what's the society level impact I'm having. So I started off as a biologist, because I thought I could maybe help. [23:37] with certain diseases or help find cures or solve things for people. And then that transition to technology, how can you use technology as a lever to sort of impact the world in a positive way? Lately, I've been thinking about other things in terms of either applications of technology or, you know, one project that I've been working on a little bit with some folks on my team, we're going to change the name, we've been calling it monumental. And it's basically, if you look at every society at its apex, [23:59] people have built large-scale public artworks or architectural works to basically inspire the next generation, right? And so the Eiffel Tower was built in the 1860s. [24:10] Hundreds is an ode different steel making for a World Fair, right? They're literally trying to show off how good they were at making steel. Yeah, we're kind of missing that right now. It feels like now we haven't built anything big in like 100 years, right? It's all very utilitarian now or something. It's very sort of I think in general, postmodernism has been a very bad trend in every level academically, societally, architecturally, etc. And so we don't really do large scale works of public beauty. And so that's one project that we're working on, which is we're looking at a few different test sites. We have a bronze foundry in France that's actually doing our first work. It's a small it's only like two feet.

[24:39] round, but we're just seeing sort of the quality that they produce. We're working with some marble worksplaces. We're looking at carbon fiber. And then we're looking at test sites and we're working with some, both architects as well as developers and saying, are there places where we can put large scale statues? And it could be something like the 15 or 20 foot statue, like the Atlas in front of Rockefeller Center, or it could be a multi-hundred foot work like, you know, the Eiffel Tower or the Statue of Liberty or something like that. And so the aspiration is to do one or more of those giant public artworks somewhere. It's cool that you're doing it now while you can also [25:09] 30 years or something and doing it. Yeah, I think also from a longevity perspective, that may be a really interesting artifact to leave behind. Yeah, I think 100 years from now, that may be besides my family, the thing that could sustain. [25:20] Do you think that having this sort of mindset that makes it so that you're always aspiring to more? And one of the one of the cool things about business, but one of the also things that I think makes some people feel like they can get on a treadmill is no matter what you accomplish, unless you're Elon Musk, there's somebody who's accomplished 10 times more than you accomplish 10 times more. And there's still somebody who's accomplished 10 times more and everything like that. Do you think that that is a fundamentally. [25:42] healthy thing? Or do you think that is something that is like a fundamentally like anxiety, sort of dissatisfaction inducing thing? And... [25:50] if the answer is in the middle or blended somehow? How have you managed your own psyche as you've kind of continued aspiring to a new rank all the time? I don't know that I've aspired to a new rank. I think what I aspire to is to do things that are useful. It almost feels like there's a set of people who truly self-sacrifice and have... [26:08] pretty rough lives otherwise, but they're doing large-scale works for humanity's sake. Like Elon seems to be self-sacrificing quite a bit.

[26:17] If you read a lot of biographies of people who have done very large things, many of them have had these unhappy lives. And I think part of that is that self-sacrifice. So to your point on is it good or bad, it may be terrible for the individual in some cases, but maybe fantastic for society. And maybe society doesn't move forward that much without these sorts of folks. One of the things that we've talked about before is that there are pivot points in careers. And you go through these moments where you make a new change and decide to do a new thing. I did one year of investment banking before. Sorry to hear that. [26:47] was terrible. I mean, it was bad on a lot of those. But I did a year of investment banking. Then I worked in tech, joined a company, started a company, became an investor, angel invested throughout. But like, you know, I could probably point to like three or four pivot points that have happened. Like, and those seem important. Like those seem like more important than other moments in time. How do you when you're talking to either people, you know, earlier in their careers, when you think about for yourself, like, how do you navigate those? Like, is it spend longer thinking [27:17] Would you say, "Go talk to a zillion people"? Is it just all your gut? Is there some frameworks? Yeah. I think there's almost two types of pivot points. There's the things in your life that matter, and then there's the things in your career that matter, and those overlap that are different or distinct. Career-wise, I think we talked about it in terms of, are you in the right location? [27:36] in the right company, the right network. I think those are the things that actually do matter from a career perspective. And then every once in a while, you're making the right trade-off. And I think many great careers have two or three of those choices done right. Sometimes when I meet people, I used to do this. I don't really think of it this way anymore, but I used to almost view people

[27:51] I'd meet somebody and be like, what's a Monte Carlo simulation of them, right? Monte Carlo simulations, you rerun things with a little bit of randomness like a million times, and then you end up with some average outcome. And so if you were to rerun somebody's life a million times, on average, how do they do? That's a good question. And there's going to be probabilistically scenarios where you're a total wipe and scenarios where you do incredibly well despite yourself. And I know people like that. Probably on average, you end up doing extremely well, depending on who you are. And so those are the types of people that I think, on average, have amazing careers, [28:21] characteristics and then those pivot points or decisions, they should make better decisions than average, but everyone's fault they'll get something wrong. And so sometimes you see these careers where somebody just kind of had to hit it every time. [28:29] And the question is, are they exceptional? And in some cases they are, or did they also get lucky once or twice, which is often the case as well. But there's other kind of big life drivers, I feel, that are decisions that you made. And those include things like, what school did you go to early on? I didn't realize an Ivy League school mattered, and I didn't apply to any of them. Are you in the camp of thinking still that that matters much? Yeah, 100% it matters. Because of this network thing and this talent? Yeah, the network and the brand opens doors, it opens opportunities, it creates a lifelong network. The schools have unfortunately purposefully degraded that. They removed merit, they did all sorts of things that make it their... [28:59] student bodies worse. They selected for activism over goodness, all sorts of stuff. And I think we're kind of seeing a slow motion pay the price of that right now. But I do think on average, it's still better to go to a branded, well-known school than not. If you had to guess, are we on a trend where in 20 years going to Stanford still matters? Or do you think that we're heading down to sort of the Peter Thiel forecasted thing of college is a silly exercise? I think it depends on two things. I think one, it depends on what the schools do to

[29:29] reinforce quality in terms of the types of people who go there. And I think they still have very high quality people, but they've mixed in a lot of low quality people. [29:37] under all sorts of assumptions about what makes sense. And then secondly, I think it comes down to the degree to which [29:41] there are advanced forms of technology that could disrupt how society works, right? And those are the two things that could matter. [29:47] You were speaking about like... My prediction, though, would be on average, it's still going to be important. [29:51] When we were talking just a second ago about sort of, you know, there's some people who navigate these pivot points in their career and they kind of seem to get lucky a couple of times and it just keeps going up. And that's great. There's also some examples of people who are really smart, really hardworking, and it just seems to like not go their way. Have you ever thought about that or like diagnosed what might happen? [30:12] be happening there. [30:13] I find it really difficult to diagnose because I know a few very talented people who just [30:19] tried a few things after another and it just never worked. [30:22] And you don't know, is that just luck? [30:25] Is it a characteristic of finding product market fit? Is it something else? Right, like somebody gets a bad role in the Monte Carlo simulation. Yeah, exactly. And so is it just a bad role or is there something inherent to that person where maybe they filter information slightly differently and they make... [30:39] more bad decisions like there's a few people that I've worked with where I [30:43] It's been very hard for me to understand their thinking or their framework for the world. There's one or two people who repeatedly just make bad decisions. Another version of that would be an amazing technical person who has no commercial sensibility and can't pick it up. And we've all worked with people like that, where for some reason, they just can never think, [30:59] from a business perspective or from the human psychology perspective, right? Is it brain wiring? Is it...

[31:05] something else? Like what's the, why are they unable to learn these things? And it probably goes the other way, right? There's probably people who could never pick up a technical subject matter. [31:12] And so it could just be an inherent characteristic. It could be something else. I'm not sure. [31:16] For people trying to specifically become great investors, because we talked a bit about companies here, for people trying to become great investors, what do you think are like the different potential configurations of how somebody gets great? [31:28] over time. [31:29] Say somebody who has maybe been an investor for a few years or hasn't even done it yet. But what are the ways that somebody becomes great? I don't know. [31:37] It seems hard to tell. I can't tell either. Well, the problem is I don't think there's a single right way to be a great investor. Also, it depends on what stage you're investing at. Let's say it's early stage. Early stage, you just need one thing to truly work and you're considered a great investor, even if you do 100 things that are bad. The question is, what is consistently good? How do you have a high hit rate? It's a little bit different. I feel like there's all sorts of styles. I think Naval is a great investor. Naval Ralkant. [32:03] And his heuristic is often, is it an interesting technical problem? Is it somebody I want to work with? He has a set of criteria that are really good but very different from mine. Mine are much more product market. I think there's a product market fit here or potential for it. And he's done great. And so I don't think there's a correct style. I think each person has to kind of adopt... [32:23] the style that works for them. I think there's a really good [32:28] set of discussions with Jensen Huang from NVIDIA, where he points out that his org structure is radically different from most CEOs. And he's like, you should really...

[32:36] build the org structure around the CEO. [32:39] And you shouldn't be able to just plop in a new CEO in the same org, right? It should actually be tailored to that person and function around that person and their style and all the rest. And I think that's true of investors too, right? Like different investors have very different styles that they bring to bear. [32:51] I don't think there's a right one. I think it's just differential trade-offs relative to what that person's good at, what they're interested in. [32:58] how they work with people and founders. That seems like one of the easiest places that people go wrong is investors, I think, can often look at other people who are succeeding and try to do their play. And it's like, if you're not Jensen Huang, don't try to do what he's doing kind of thing. Yeah, and it's very hard to replicate these things too, because again, it may just not be a good fit. [33:15] it's almost like there's different types of athletes, right? And you're like, well, the power lifter may be really different from the sprinter, but they're both great athletes. That may be true for investing. Maybe somebody is a power lifter, maybe somebody is a sprinter, and you just need different training and different styles and different things that you do. I have a couple of questions. [33:29] about [33:30] how you personally have worked as an investor. How do you spend your time? Because you are involved in a surprisingly large number of companies that a lot of people have heard of. I assume those founders are calling you. When I was running Lattice, I called you sometimes. So there's a lot of people who called you. What does your time look like? And now you've also got a lot of stuff going on. So how do you seem to be there [33:50] for everybody because I think somehow there's a combo where it's notable how founders say you pick up the phone, but you're involved in a lot of [33:58] big projects. Yeah. So what's your time like? [34:02] It's very busy. I think, you know, one thing I've been trying to sort on my side is how to get more leverage on time. And so, you know, I'm definitely going to be...

[34:11] adding in my team and adding people [34:14] Over the coming year. So my goal for this year is to be able to be able to offload 30 to 50 percent of stuff that I'm doing that I don't think is relevant to the things I really enjoy doing. One of the things I really enjoy doing is working directly with founders and like. [34:24] helping them with whatever sort of things they need help with. And it could be trivial things, it could be important things, whatever. [34:32] But also, I used to, and I'm going back to spending more and more time more directly hands-on with technology or more hands-on with projects or other things. And part of that also has just been finding people on my team. [34:43] who can do things like that. So for example, Shrena, my team is working on this project called the Alexandria, where we're taking eventually 1000 of the great works of humanity that are off copyright in terms of philosophy and history and other texts, and then using AI to translate them into languages that represent 85 to 90% of all the spoken languages in the world in terms of population coverage, building audio books for all of them so that you can stream it off of every device. [35:10] So the idea is basically, can you create a modern Library of Alexandria where humanity's knowledge base is sort of unlocked? Wow. You know, and so there's stuff like that that I like doing and I think [35:20] There's a societal version of it, and it's just fun to play around with the technology and actually ask which APIs are actually good for certain things, or how do you think about QA across a very large text? [35:28] Or how do you capture nuances of work? So for example, you're dealing with the Bhagavad Gita or the Bible or something else. And there's all these translations, right? There's the King James version of the Bible, because it's the specific translation and the nuances of words are said a certain way. And so how do you think about word nuance against dozens of languages relative to such an important set of texts? So I think there's things like that that's interesting questions. Totally. And building your own projects will lead to...

[35:56] anything you know it could or it leads to nothing but it's just interesting you know it's back to like what are you driven by i'm driven by like uh technology it's impact interestingness like things that [36:05] can move the needle for the world, but also I like the technical details of things. I also feel like because you've done a few things [36:11] that prevented you from getting caught up in tons of minutiae, like... [36:15] You mostly don't join boards as far as I know. You don't have to navigate firm politics, obviously. So you've got a lot of things that I think are huge draws on other people's time that I suppose you've avoided. Yeah, I've tried to purposefully avoid them. I used to be on boards and I found them... [36:31] Reasonably painful. I mean, I'm still more recently I've kind of added to a couple boards, but they're largely silent seats. So it's a little bit of, you know, I officially have a board seat, but I don't show up to the board meetings. Yeah. And you're not, you know, you're not in the middle of internal meetings. [36:46] firm meetings and stuff like that. There's so many other things people get caught into. Yeah, yeah. And again, there's a lot of that that's accumulated more recently. And so that's why I want to hire people to offload it. And so I think I probably have to hire, you know, half a dozen people or something. What outside, obviously, you're interested in AI and have [37:00] done a lot there. What outside of AI are you most interested in right now? There's interesting in terms of things that I think are useful and interesting in terms of things I'd invest in. And those aren't necessarily the same thing. Maybe what do you find just interesting to you? Yeah. You know, one area of sort of application of technology that I think is very under focused on, I think there's two or three. I was about to write a blog post on this or a post on this where there's like four or five areas of biology.

[37:24] that I think can be applied that nobody's doing anything. I'll give you like four or five examples, or very few people are doing something. There may be the one-off company or whatever. One is, and there's a company called Ovum doing this, there's research out of Japan where you can take any cell type, you can differentiate it down a set of lineages, and then eventually you can make sperm or egg, right? And so basically anybody could reproduce with anybody. They've done this in mice, they're not translating it into people. And that looks like it's possible? [37:47] Yeah, yeah, again, it's done in the lab for mice. It should be done, you should be able to do it in people. Wow. And it has those sorts of weird implications, like you meet... [37:54] LeBron James at a party and you take a skin scrape and suddenly you claim that there's a paternity suit or something, you know, because you'd be able to differentiate the cells down the line of sperm. And then, you know, and so there's crazy things you can start imagining, but it also means that anybody over a certain age or a certain capability, whatever it is, you can have kids, right? That's huge. It unlocks society, right? Why are there so few companies working on that? That'd [38:18] And also male, male, female, female. Could do everything, right? Wow. Yeah, it's amazing. That'd be a really big deal. Yeah, it's a huge deal. That's why I'm like, why aren't there more people doing this? I'm also like, why are more people not talking about that? That's crazy. Yeah, yeah. And there's a whole swath of reproductive biology that nobody's doing much in. That's one area. Another area, again, these things may sound stupid, but I think they're a huge quality of life. There's a whole set of genetic pathways that lead to tooth regrowth. So if you have a cavity, you should just be able to regrow the tooth. Lots of animals actually have replacement of teeth. [38:48] has, and again, pathways have been mapped out. You should do some translation. I'm not meaning to trivialize it. It'll take time and work. Third is sort of cosmetic applications against longevity.

[38:58] So graying hair, balding, wrinkles, you know, again, there's a lot that's been uncovered there from a basic biology perspective, it just hasn't been applied. Like big Brian Johnson energy going on. Oh yeah. That'd be good. Well, I mean, if you think about it, Botox is a $40 billion market cap company or the company that makes Botox. And in that case, you're literally injecting a bacterial toxin into your face to paralyze nerves. Is that bad? [39:20] It sounds good to me. It sounds okay. It sounds fantastic. When you say it that way. Yeah, when you say it that way, I want more. Yeah. Why aren't there more toxins I'm injecting? Yeah. And so why don't I use more paralytics? I don't know. And so... Doesn't it also make your armpits not sweat or something? Yeah, that's why I use it. Yeah, that's mainly what I use it for. Otherwise, I'd be sweating like crazy right now. For sure. So there's just all these really interesting areas of biotech where nobody's doing anything. And if you look at biotech, it has all sorts of structural issues in terms of why it's set up certain ways. And there aren't really that many founders. [39:50] and they're all spun out to be bought by pharma. You know, it's a very specific infrastructure. Yeah, it's been hard for like Silicon Valley venture to fund biotech. Obviously, it's very profitable and goes well a lot of times. It's just been a hard thing for... It's a very different structure and the outcomes are... Like everything's different about it. But the key thing is like there's like half a dozen things I can think of that are societally really impactful or useful that aren't... [40:10] going into cancer, which is really important, right? I used to work on cancer as a biologist. Mm-hmm. [40:14] for years, right? Will AI matter to some extent in accelerating this, or is it not clear that it will apply? It's unclear to me. Anything outside of biology that speaks to you right now or gets you similarly excited? I mean, there's a ton in AI, obviously. [40:27] I've long been involved with Andrew from a defense perspective, and there's interesting things happening in defense. I mean, there's a lot of areas that I think are interesting. I guess there's sort of this two by two matrix of interesting versus focused on.

[40:41] You can't focus on everything. Well, I mean, it's not just you can't focus on everything. It's kind of like, what are the things that nobody's thinking about that they should be thinking about? Certain aspects of the energy are like that. Um... [40:51] Certain aspects of biotech are definitely like that. So it's more like, where are the gaps in the world versus, hey, everybody's funding AI. Do you think about that question at all from a market perspective? Meaning when you think about what stages of the startup ecosystem are over and under appreciated, it's not just about what companies, but also just what stages and where's the capital going? I've gotten some of those things very right and some of those things very wrong. So I did a bunch of stuff in crypto in 2017, 2016, because it was so clear that [41:20] It was important. I was really... You basically just believed crypto, then things were good. [41:25] Yeah, I mean, you got the theme right, you're right. Yeah, yeah. And there's some areas like that where that isn't true. A friend of mine actually is a very prominent crypto angel, and he invested in, I don't remember how many, 200 crypto companies. And he said his biggest takeaway when you look back at his portfolio of crypto investments, he did amazing on them, right? I don't know what he made, 20x or whatever his money. He said if he'd actually indexed further, he would have done better because he missed Solana and he missed one or two things that he said, as long as I took the meeting, if I'd funded it, I would have like done a 40x instead of a 20x or whatever. [41:55] more than people even talk about. You were investing in AI slightly ahead of everybody else, I feel like. And you were just doing a ton of AI investments in, let's say, 2022 and 2023. Probably got something, it feels like. Yeah, no, it ended up quite good. I mean, I led the first round for perplexity. I was in the first round of Harvey. I was early to a bunch of character I was amongst the first money in. Which is not to say it couldn't still be good now, obviously. It's just that now that everybody

[42:25] I mean, even then, you know, my big lesson from technology trends, especially these things that'll last for 10, 20 years, is people always say these things are over, overhyped, and it's still early. It's early for a longer time than you would think. It's always that way. Yeah. Social networking was that way. Basically, all of Silicon Valley can think something, and we're all still early together. And they all still be right. Yeah. Yeah. And then the question is, are you choosing the right things? Because in any technology wave, 95% of things go under, or they're crappy. And most of the market cap is usually like two or three things or five things or whatever. And that's going to be true here. [42:55] Thank you. [42:56] and early and then just even if you're indexing, just index the wrong things. A friend of mine did that in social gaming. He had a fund in 2008 or 2009 or 2010, and he invested in 30 social gaming companies. And he missed Zynga and he misplayed him. And his fund basically went to zero, but he invested in two other companies outside of gaming that actually really worked. And so he did really well. But he indexed the right theme and just missed the right companies. And so that can happen too. Because you have so much range in terms of like what stage you'll do. I mean, like the other [43:26] you know, both incubate things and also do a pre IPO round, which you also are, you know, capable of doing both. And does that make it so that you are thinking often also about, you know, about Josh, about Josh, just like all of that. Yeah. Josh is great. Josh is great. Doing it early, going early versus going late and what types of moment we're in. Like, you know, there was a moment where a couple, maybe it was 18 months ago or something, but there was a moment when like the growth stage was kind of clogged up and just like nobody wanted to move on series B

[43:56] Yeah, I kind of view it as just like what's good. So three years ago, the good stuff was super early stage gen AI. And that's where almost all my time went. And it wasn't some calculated thing, it's just I kept seeing great things. [44:11] A year and change ago, it was all these amazing compounding companies that suddenly went out to a fundraiser again. It was Rippling and Figma and Anduril and a few other things all went out. And there's things that looked like they could go forever. They could go forever. And then... [44:25] Six months ago, it felt to me like it was a lot of this kind of mid-stage AI company. So that's when me and my team did the Bridge Round and Decagon and Harvey again and a few other companies where it's just kind of like, OK, these are the things that are really working. So is the way that you make these sort of like thematic observations just a function of good stuff that comes by? Or are you actively thinking about it or are you just observing what's around you and that's how it goes? [44:55] of course you do it. Or crypto, hey, it's this real C change and how you think about two or three really big use cases. And then there's other times where you think there's a theme and there isn't. You know, that happened to a lot of people with ed tech or digital health, which I did, right? And then sometimes it's just organic, like a bunch of stuff shows up. [45:12] And I think most of the time it's organic, right? [45:16] To some extent, if you're only thematic, there's enormous hubris in terms of assuming that you know better than all the founders out there. There's thousands and thousands of founders excavating away, looking for that. There's like a genius hive mind happening. Yeah, the genius hive mind, and they're covering a huge surface area. Are you going to be better than thousands of people in terms of deciding what's good? Most of the time, probably not. Every once in a while, you might get lucky. I mean, I guess the steel man of the counter is you've got to just get good at something. And so it's easier to get good at something narrow than to do everything.

[45:46] It depends on how you define something. Yeah, exactly. Yeah. And I guess the counterback would be like, do you want to be pretty good and on the right theme or do you want to be incredibly good at the thing that's, you know, not as a matter? Yeah, exactly. So, yeah, I think you kind of be flexible in terms of how you think about the world as an investor, right? As a founder. Yeah. [46:03] you definitionally have to choose one thing to go deep on. And so that's harder in all sorts of ways. And I think maybe what happened is 10 years ago, [46:10] The best advice that you could have gotten was keep going no matter what. There's a small number of themes and just dig away and it's hard to raise money and et cetera, et cetera. It wasn't that hard to raise money, but still on a relative basis. Probably the best thing to say these days is maybe you should give up. [46:24] This thing isn't working. There's so much low hanging fruit in AI, for example. And I think early in a market, you want to focus on the low hanging fruit. And if you have these really complex, hard things you're doing, you're doing the wrong thing. This should come way later in the life of a market. Right now, all the easy shit's available. Just go do an easy thing. Totally. Well, and some of the easy things are important and clear, like customer support. Like a lot of these things are just, they're good and they just haven't been done yet because there hasn't been time. Yeah. And people really overthink that. They're like, oh, it's easy [46:54] to do it and then nobody does it. Right. And it's actually just like a huge blessing to be at a platform shift where the easy-looking fruit hasn't been. Yeah, it's amazing. Go do that. Okay, last question because then I think we've got to give the room up. You've got a new book coming. Yeah. What's up? Yeah, so I'm working on another book for Stripe, Stripe Press. And it's basically more of the zero to one part of the startup journey. And so it's just like my High Growth Handbook, it's very tactical advice.

[47:17] Except instead of being tactical advice to really scale up a company's tactical advice around how do you hire a first employee? How do you raise money for the first time? How do you build your first product? How do you choose a market? You know, all the very early stage stuff. So I'm very excited about it. That's good. How do you find the time to do that? It's been tough. You just don't sleep. [47:32] I try not to. Try not to. That's great. All right. Well, this is very fun. Thanks for making me do it. Yeah, thanks for doing it. Yep.