Keith Rabois: On Identifying Talent [Classic Interview]

Welcome back to Turpentine vc, the podcast where we discuss the art and science of building successful venture firms VC to vc. Today we're sharing a throwback live conversation with Keith Raboy discussing his frameworks for identifying talent and building category defining companies. Up ahead, you'll hear candid anecdotes about specific operators who have gone on to build a significant companies, as well as stories about PayPal, LinkedIn and Square. Keith focuses heavily on talent assessment in this discussion, what makes people strategic and how to spot the spark when evaluating potential. And don't miss the next episode of Keith's podcast with Logan Bartlett, Kevin Ryan and Zach Weinberg on the Turpentine Network returning this month. You can find a link to subscribe to this won't last in the description. Please enjoy.

So we are super lucky to have Keith today on both Rise retreats. I almost convinced Keith and to come up to Tahoe, but it didn't, didn't quite work out. So we thought we'd bring the Rise to Keith. So we have a few things that we're going to talk about and we're trying to talk about things that Keith hasn't talked about in many numerous interviews. One is career strategy. Two is identifying talent, some of which he's talking about, and then also identifying markets, identifying how to pursue find great ideas to pursue as an entrepreneur. So I thought we could first begin by setting the framework of you give a lot of personal friends, career advice, a lot of executives in the Valley, a lot of just young, really talented people sort of with wide variety of experience. What advice or what sort of career frameworks do you typically find yourself giving them? Let's start broad there and then we'll go more down.

Yeah, I mean, I think the first thing is I read this book when I was growing up, written by Pat Riley, who used to coach several basketball teams successfully and then became the sort of general manager of the Miami Heat. And he wrote a book in the 1990s called the Winner within, which is kind of cheesy, but there's a couple of lessons in there. And one was he had this quote in there from actually Jerry Garcia, of all things, where he said, you don't want to be the best at what you do. You want to be the only one who does what you do. And sort of that made sense to me at the time. And then I basically give people that advice, which is figure out how to be the only one who does what you do. And you obviously have to narrow your definition of what you do to accomplish that. But it's also a little bit like many people I work with went to some elite school at some point in their career. And when you apply to these schools, you typically write a personal statement. And generally the people who get accepted, having worked on some admission stuff, are people who write a really good personal statement that defines them in a kind of a unique way. So I think the same thing is true professionally. And then it's the exercise of figuring what that could be, what that should be for you. And it often takes time, trial and error actually to figure that out. It's not obvious for most people.

So let's give a couple specific examples. David Hahn, product executive, one of your mentees at LinkedIn for many years. Jared Fleasler. Yeah, Fleasler, operational executive at Square, one of your mentees as well.

Grassidonia.

Yeah, totally. So what do you tell them to do that no one else is doing? Because right now they're COO or CPO at respective companies.

Well, yeah, I mean, now these are all three people we just mentioned are actually interesting because I hired them all when they were 22, and all three of them particularly are good examples because none of them went to elite schools and none of them had technical background. So Brian Grassoni runs Square Cash and has done phenomenally well at Square, worked for me at Slide and then came over to Square. Jared, same thing, is now the COO of scribd, was a general partner at Matrix, worked at Square and Google and Slide and Han I hired at LinkedIn, and then he stayed for forever and then just became the Chief Product officer last year at Instacart. All of them literally went to schools that are not well regarded, had no connections in Silicon Valley, and definitely were not technical, but all have done extremely well in their careers. So questions like how and why? And I think one of the reasons is they all had some skills that were unique to them and they figured out how to leverage that. And then secondly, they all developed this broad skill of what the term of art. You know, sort of the jargonistic term is strategy, strategic. But they actually developed an ability to be perceived as strategic. And that allows you to be promoted from like, you know, a functional executive to a senior executive. And we can talk about what that means, but all three of those are really good examples.

Did you have a conversation with them of, hey, maybe you should start something? Like, how do you think people, people who already have achieved a certain level of success think about starting versus joining?

Well, two of the three pretty aggressively don't want to start Something or didn't want to start something. Their risk return profile and maybe where their skill kicks in is post product market fit. Brian Grassadoni did want to start something after our slide experience and he had a co founder and an idea and I had to sort of intercept that and talk him out of it to come join. Join me, you know, as like the 22nd employee, I guess at square.

Right. How about let's go someone younger, let's say someone like Deli and your chief of staff right now who disappeared. Yeah. To go to Barry's boot camp. Good.

Now we can talk about.

Yeah, priorities. So in true chief of staff fashion. So if he. Wait, he's 23.

He's 24.

24. Oh. So let's say he had, you know, done his tour duty at chief of staff at Khosla and your chief staff. He could do any number of things. He could start something, he could join something, he could perhaps work his way up in venture capital if he thinks about sort of long term optimizing career success. What would you advise his next decision or what framework should he use?

Well, I think it's actually a good topic because he sort of accidentally became my chief of staff. Like actually we're trying to, we, we were having dinner and we were talking about maybe I should hire a friend of his as my chief of staff.

That's the strategy.

And he was supposed to literally call up his friend who's like a CS graduate of Harvard who now works at Google and ask him if he'd be interested. And so about a half hour goes by and he starts texting me furiously and he's like, hey, what do you think about me if I did this instead? So as he was practicing his conversation with his friend, he's like, oh, maybe I should do this. So it's sort of serendipitous and accidental. It wasn't designed by either me or him originally. And then he was only going to do it for a year because he had founded a company, so short bio, but basically was a teal fellow, dropped out of mit, then went to yc, did his own startup and then joined sort of a high growth company in our portfolio for a while. And he basically was planning on I'll do this for a year, see what I can learn. And then I want to go back, found something, join something. And the goal was to learn a couple things by joining venture. One was how to assess people, which we'll talk about. And then secondly, maybe a little bit more breadth in terms of business opportunities, ranking them, etc. And I think immediately, within a month, he picked up how do you assess people? Because basically, as he just said, actually when he was having a drink here, everybody, when you drop out, he was an MIT engineer. So he knew people like him. They're all technical, very nerdy, and very young. But that may not be the right formula for the company you're trying to build. So for example, the startup that he did do was an enterprise sales company. He knew nothing about enterprise sales. And I would try to do teach it a little bit on the fly, but he didn't even know the beginning of how to recruit an enterprise salesperson. If he interviewed an enterprise salesperson, is this person great, stellar, or B minus? How do you do marketing? How do you get product market fit? How do you get evidence of product market fit in hardcore enterprise sales? And so I think that the goal was to learn how to evaluate people. And then so he shows me around most of the day and he comes to board meetings with me and immediately, a month or two in, he could tell like, what the differences are. Like, he comes to interviews with me when I interview candidates and usually like, I'll actually ask him for his feedback before I. And when I think of a particular candidate and he's already very quickly picked up on, this person's clearly very good and this person's not. This executive at Company Y is really impressive. The CEO, we actually rank our CEOs and he can rank all the CEOs I work with very accurately without any feedback from me. And he developed that just by basically through osmosis. So you can find ways to develop taste in areas you don't have. And then if you're going to build a company from scratch, if you believe, as I do, that the team you build is the company you build, you want to be able to have an unfair advantage in assessing people. And so there's only so many ways to get that and develop a network too. One of the things VCs do when they do their job well is they can connect you to people that are very important for your company's success, but that you don't have in your natural network. So a classic example is you want to hire a cfo. Most people who are young and technical or designers and Young don't know CFOs, right? They have no idea what a CFO even does, let alone like, where do I get a great one and how do I evaluate them? So that's one thing a good VC can do is I happen to know lots of CFOs, and I've interviewed, I don't know, hundreds probably. And so I can help assess a CFO candidate if that's what your business needs. Not every business needs a CFO very early, but some do, like capital intensive businesses, could use a CFO pretty early. Those that use debt and turn debt into oxygen, which is a very common thing in Silicon Valley these days, need a CFO or someone like a CFO pretty early. So it depends what the, what the product and what the market is. What are the key skills and then how do you get that if that's not part of your natural network?

That's really interesting. Let's say that you no longer needed Delian's Jeep staff anymore and he was set free and he had to think about and because I think Delian is representative of a lot of people here at Rise who are somewhere between, you know, 20 and 40, really, really talented. And they have, they have a network, they have skills, and they're asking, hey, should I start a company? Should I join a company or should I become a venture capitalist? Either junior or senior, depending on where they are. What framework do you recommend for someone like that?

I think you should only start a company if you have a specific idea that you're pretty excited about. I don't believe in the I'm a founder because I want to be a founder, like philosophy of life.

Rishi or Boswell, these people had ideas.

Boswell definitely had an idea. Rishi was a little bit more exploratory, although he wound up coming back to what he was kind of going to do in the first place. So I think there's. You can acid test your ideas. Like, you may have an idea. Like, I'm pretty excited about acts, but is it really a good idea?

Right.

And that's a reasonable process to go through before you recruit people to your team, before you raise capital, before you commit, you know, extras or life. But I don't think the, hey, I have no idea what I want to do with my life. I know I want to found a company because that's kind of cool or trendy. So I'm going to go explore a bunch of ideas. I just don't buy that.

So if Dylan came to you and was like, I want to be a.

Founder, he would then hopefully have like, there's this specific idea that I just can't stop. I can't get sleep at night. About like, literally in the proverbial, you know, I can't sleep. Like, I heard this idea doesn't have to be your own original idea. You can hear it from somewhere else, but it just sparks something and you just can't stop thinking about it.

Right.

And then you're like, okay, now what are the, what are the barriers to success for this idea? What kinds of people and market and, you know, distribution and other complexities are there and how do I get smart about those? That's a very reasonable process. And it's perfectly fine to also say, oh, shoot, I discovered an insurmountable barrier that I don't know how to solve. And maybe I shouldn't do this idea because I can't solve this particular problem. And so it can be like a showstopper.

Right.

But I don't think it's like a search for months and years and then you go find something that's something cool. It's usually something that you encounter and then realize other people have the problem. And it can be a small group of people that have the problem, but you just think it's really important to the rest of the world and to that group of people that you can fundamentally transform their lives. And it turns out there's a lot of people that are like them that you didn't know. I mean, Delian actually, in a specific example, has figured out that he wants to do Venture, which is not something I typically recommend for young people to like, do for like the next 50 years of their life. Because you want them to have writing experience. Yeah. And build something, try something. I think there's a lot of reasons for it. But he happens to be intellectually curious. Ventures a great job if you're intellectually curious. It may be the best job on the planet for someone who's intellectually curious because you get paid to learn new things. I knew nothing about health care. I joined KB five and a half years ago. I literally knew nothing about healthcare. And I just felt like, well, healthcare was clearly broken. At least my own experience told me that it wasn't particularly like, well run. And you could read stuff in the media about issues with health care, but I had no idea about solutions and why there was no solutions. So I just started meeting people in health care and started investing in health care. And now probably 20, 25% of all my investments are in health care. And that's what I get paid to do, is find cool new areas I know nothing about and then become an expert over time at them. And there's nothing like that. So if you like that. Second thing is if you like working with really talented, ambitious people, Venture is perfect. It's like playing with NBA. It's like learning to play basketball with NBA All Stars. Everybody we fund is pretty damn talented. Doesn't mean they all work out. It doesn't mean occasionally we don't misassess them. But the goal is to fund people who are like NBA All Stars. And that's very different than building a company where you have people with mixed goals, ambitions, talents, and you have to construct this overall team that eventually at scale regresses to the mean of normal distributions. So I get to work with like amazing people that challenge me. Like, the questions they ask me every day are the hardest fucking questions ever. Because if it was easy, they wouldn't ask the damn question. So the three, when they, when a founder who we've funded walks in my office or meets up with me and they pull out this list, my eyes are like, oh, shoot. Because you just know what's coming. These are really hard questions. It's going to be a series of them and there's no right answer. There's hardcore trade offs. But once in a while, when you can help them solve the problem and their eyes light up and you know that you've just made like someone who's like Steph Curry, like eyes light up, like in a better way, in a serious way, it's totally rewarding. So there's not that many jobs where you get to do those two things. Yep.

Do you feel like they're almost, you know, Mark sister has this. Marcus is great, but I think this thing's a little simplistic. He says like in the beginning of your career you want to work to learn and then you work to earn. And I'm curious, do you think of it? There's literally like stages of your career. Like you go to college, then you do like this two year thing, build a network, but like get together.

That might have been true like 50 years ago. I don't think. I mean, I think that they'll learn sort of earned philosophy probably is right in some sense, but the pace that you go through it may be very variable. Maybe like a month for some people. Yeah, a year, a decade, whatever. 20 years for some people. Whereas I think in society 50 years ago is very regimented. Like if you're in your 20s, people just wouldn't let you do X, Y and Z. And if you're in 30s, you still couldn't do it. Like law still works this way. Like I grew up as a lawyer. Like people I went to law school with, people I clerked with are now like at the prime becoming at the prime of their legal career. Like they're getting appointed circuit court judges and I wouldn't be surprised if some of my friends, you know, wind up on the Supreme Court someday. But like they're now getting in the zone.

Yeah.

Whereas like, for me, it's getting towards the end of my career. So, like different, you know, law just as a hierarchical, like experience driven profession and still hasn't transformed, but many other fields are completely different.

So I have this sort of broad theory that I'm working, working through that there are sort of four different, I don't know the right word. If they're like career assets or almost loops and they are financial capital. One's network, one's like brand or reputation, and one's like unique skill set slash knowledge base. And my theory is that young people often optimize too much for brand or network at the expense of a unique skill set or knowledge base. And that the unique skill set or knowledge base is far more compounding. Like if you have that, it's far easier. The network can be there in a day. Like it could come right away, the brand can come right away and financial capital can come too. But you're not going to get unique skill sets, knowledge base or it's much harder. And so people will spend like 10 years building the others without having something.

Yeah, I agree with that. The fundamental like skill and ability that's unique and differentiated and mastered like the top 1% of something will eventually solve the other problem. So, example, recently, look at my Twitter feed. You'll see. About maybe a month ago, I tweeted this thread that I found about China. I was like, this is the most insightful thing I've read about China in like five or 10 years. I had no idea who this person was. I just read his thread. Turns out the guy's like some random 18 year old in New York. Like literally random 18 year old. And I didn't even know he was 18. He just sent me an email after I retweeted it because obviously he had like 900 followers. And I just sent it to 150,000 people. And so he's like, thank you very much, by the way. I'm this like New York high school student. Like I'm 18 years old. But the point was that there was a spark there that lots of people write him and talk about China. He was the only one who wrote something interesting that I've actually seen in a long time. And so that will propel him far if he can do that consistently. I mean, it'll propel him reasonably well if he can do it once every five years. But if he can regularly write something interesting, insightful on a topic that lots of people care about, the network will exist. People will definitely. Then he sent me an email. He's like, hey, I'm going to be in the Bay Area. Would you meet me? And I'm oh, like, of course. If he had sent me the same email a month earlier, there's no way I would have met him.

Well, it's interesting. Let's, let's go on that for a second. Hey. We'll continue our interview in a moment.

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There'S this guy named Mayer on Twitter. I don't know if you, you might follow him. He's. He has sort of a cartoon avatar as a, as a, as avatar. But he naval always retweets him anyways. He's really big on Twitter, he's like 20 or something and he's starting this sort of company I'm going to botch. It has nothing to do with him being super interesting on Twitter, but he crushes it on Twitter every day. Just really insightful things. You'd think he's a VC or something. And basically the question is, or one of the variations of the question is how do you convert social capital? Like how do you convert that? Because that capital means something. But how do you convert it to other forms of capital? Like how does he leverage that?

People will take meetings. So for example, or jobs so you guys may know Sean Rose. So originally I met Sean on Twitter and he was just tweeting these interesting things. So I kind of looked up his bio and I saw I worked at Box, and I wrote back to him like, you should be a vc. And this became a kind of witty exchange because then Aaron, his boss, CEO of Box, noticed this and put a little sign next to his desk saying general Partner, Coastal Ventures. But I was actually serious. I was like, I could tell from reading his, his Twitter feed that he actually might be a really good investor. And so I basically offered him a job. Like on Twitter.

Yeah.

So if you write interesting novel things in a field that are, you know, oversupplied with content, like lots of people tweet, lots of people talk about technology, but you could see that he had, you know, a gem of an eye for things that other people were missing.

Right.

And so, or same thing, my co founder at Opendoor, Ian, some of you may know Ian Wong, worked for me at Square. But basically he's the first data scientist at Square. I met him at a party, core party, and he came up to me as a PhD student at the time at Stanford, and he said, hey, I'm thinking about dropping out or maybe join a company. Maybe I shouldn't finish my PhD. What do you think? I'm like, sounds like a great idea. And by the way, I have a job offer for you right here. And he's like, what do you mean? I'm like, I definitely have a job offer for you at Square. Show up on Monday and I'll give you all the details. And he's like, well, how'd you do that? Well, I was like, well, you just told me your bio. So he's a CS undergrad at Stanford, got a master's in statistics and was getting a PhD in EE and had been an intern at Facebook. I was like, if I can't find something for you to do at Square, like, it's my problem. Like someone with that bio we absolutely have a need for because we do hardware, software, cs, math. So it was like a no brainer. But it was also then I also could read all his core answers and he'd written a decent amount. Right. So I could see how his brain worked. So it was much better than like a 20 minute interview in terms of figuring out like what he actually understands and what he doesn't. Yeah.

And let's move to identifying talent. So you, there's a certain number of people who, you sort of take an interest in their careers over an Extended period of time and maybe that's 15 people, maybe it's 50, maybe it's 150. It's a limited number of people. How do you choose that bucket of people?

That's a great question. Because it doesn't scale. I mean, the truthful, like it scales better in an organization truthfully than it does in Venture.

Yep.

So an organization, you can inject yourself into various people's career in a large organization like let's say square or LinkedIn or somebody, you can kind of choose this week or this month to spend a decent amount of time with someone and see how fast they learn things. And then they can go randomly rotate. In Venture, it's harder to do that. So I found it's more difficult.

The question I ask is, how do you identify potential? What makes.

It's usually a spark. So the famous story, I did one of these things where I spoke at first round capital in 2013. It was supposed to be off the record. And asked and just the presentation just came out pretty well. And they asked if they could broadcast it. And I said yes. But I told the story about one of our interns at Square, this guy named Taylor Francis, who had been my intern at Square. And the first time I'd ever had an intern, I never hired business interns. I always believed either designers or engineers or interns, but you don't want to hire business interns. But he talked me into hiring them. And one of the ways he talked me into it, he'd been Sheryl Sandberg's intern the year before. I was like, he must have learned something working for Cheryl. Like, I'm sure I can figure something out here. But anyway, so he shows up. And the first two days in, I had been struggling with this problem, which may sound totally mundane, but how do I get smoothies for my engineers at 9pm because the engineers working really hard to ship stuff. And typically in a company like Square, they all order pizza, which is not very good for you, actually. And it makes you tired, not more energized. So I was like, we're going to get smoothies. The problem is that most smoothie shops in San Francisco are not open very late. And the ones that are are not very good. So all kinds of office managers and assistants had failed to either get high quality smoothies, them being cold delivered on time at 9, not 9, 30, you know, et cetera. Everything had failed for like all summer. And so Taylor saw I was frustrated about this and he's like, I'll take care of it. I'M thinking in the back of my mind, yeah, right. Like at least three or four other people that are full time employees have totally failed this project. I'm like, try. Good luck. So all of a sudden, nine o' clock rolls around and these perfect smoothies with the right flavors, variety show up. They're all cold delivered to the right spot in the office. And I'm like, holy shit, this actually worked. And so when I thought from that, I was like, oh, this kid's talented, even though it's like this ridiculous task. And so I just kept giving him more complex and more important projects to the point that actually offered him the job of running our support team if he wanted to. Turns out he went decided to go back to school. But in any event, like, that's what you do is you're looking for the spark of competency insight that's unusual. And then constantly challenging the person with more and more complexity until everybody will struggle at some point. But you want to find something. David Sachs taught me back in our PayPal days of just constantly push people's abilities by expanding the scope of the responsibilities until they show signs of struggling.

How do you think about diversity of skill set? I'll sort of admit that I would suck at this. You already know because you know me.

So. Yeah, maybe like.

Yeah. So how do you think about, like when a person is bad at certain, like when a person has sort of hidden talents or things that aren't as obvious.

Yeah. You want to look for what it could be. I mean, that's true because it's not clear. I would have guessed that this would be, you know, his skill set or you might have a feel from experience or resume or LinkedIn profile, where to look. Yeah, but you're basically look. That's why you talk about Twitter. It's like, it's not like I don't actually read everybody's Twitter profile that applies for jobs. But if I see something, then I, then I go try to figure out what this person's excellent at. And is that what that job could be like? So, for example, let's dial back to Jared. When I met Jared, we were friends. I met him when he was still in school and he was doing this ridiculous job out of school. He was basically selling tax shelters or advising people on tax shelters. And he was very frustrated because it's a very lockstep career arc and they just wouldn't let him do stuff. And they're like, you can't do that, you're too young, blah, blah, blah. And so Every time we go to dinner, he'd just be frustrated. I got sick of listening and be frustrated at dinner. So I'm like, you don't have to do this like in tech, you know, it's more bureaucratic, you know, blah, blah, blah. So I eventually convinced him to consider tech. But what stood out to me was first thing he had to do in his job, first month, imagine graduating college. The first month he literally sat home and read the US Tax code. And trust me, as someone who went to law school, the tax regs are not particularly fun to read around real estate. In fact, particularly not fun. Cause they're quite complicated. And he mastered them like he knew his real estate tax law at least as well as I did with a very fancy Harvard Law education. And so that was pretty impressive. I'm like a think about what that means. Rapid learning curve, like ability to learn a topic that people study for years. Secondly, very boring topic. So discipline, you know, self ability to motivate yourself for things that are not fun. And then I went to watch, actually, he did a seminar, sort of like with a hundred people. And again, imagine he's like 22 years old, and most people investing in real estate are a lot older. Like you're talking 40s, 50s, 60s, maybe 70s is the audience. And he did this presentation for like 100 people and just had total command of the audience. So I was like, a minimum. You can do sales. So I'm like learning from watching. Even these are very obscure. Like, real estate shelters have nothing to do with what I do for a living. So then the final conversation about. So the first job I set him up for was to interview at LinkedIn for sales, because that was the easiest. But for a variety of reasons, he didn't want to commute down to LinkedIn. Blah, blah, blah. Anyway, he didn't wind up joining LinkedIn. But then slide. When I joined Slide, I had another possible job. So I was thinking about. But this was a little bit more producty biz Devi, which is a little bit more stretch from the things I'd already seen. So I remember talking to him about, at the time he used MySpace instead of Facebook. And I asked him why. And he was able to reverse engineer for me the logic of why he chose to use MySpace versus Facebook. I remember thinking to myself at the time, that's a pretty good answer, actually. And if you can do that as an amateur. I remember this conversation going on in my brain as he's answering. And I'm like, for an amateur, that's actually quite Good answer. And if you can do that as an amateur off the cuff, you might actually be able to do this for a living professionally when you get to study this stuff. And then secondly, he was the number two. This literally the second, maybe third, either second or third Yelp elite user in the world. He literally was the second or third Yelp elite user. And I was like, oh, that's pretty interesting. Like you're adopting new products and technologies. You know, I'd been on the board of Yelp, you know, at the time, so I knew all 10 Yelp Elite users actually. And but I was like, that's showing another signal that this person has nothing to do with technology. You know, has a pretty good radar for new and up emerging things. And so you put these little puzzle pieces together and say, okay, I'll take a bet that with some coaching, mentoring and experience, you could learn to do this for a living.

Yeah. I feel like Jared and someone like myself. And now you're bringing myself into it. I have sort of opposite skill sense in the sense that Jared is like so incredibly thorough. But maybe as a venture capitalist didn't enjoy you know, all like super wide surface area and not being able to like all the context switching. Whereas if you'd seen me in a context where you have to Remember as a U.S. tax code or something, but it would have been like, you know, and so it's interesting when you're able to see someone who struggles in one context be like, no, that person will thrive in another context.

Yeah. So Venture is different. I mean, Venture has a different skill set. I mean, I think the other thing is he didn't love Venture probably because I think also trying to figure out what your comparative advantage is. Like what's. What are you going to be the one person or how are you different than everybody else that does their job in Venture? I don't think he had a very good answer to and wasn't able to get there fast enough in like three years. So he decided to go back to like operating stuff where he actually does have some competitive advantages. But Venture is a different. Like I actually knew Dave was going to struggle with Venture because not when, not when he joined, but a year in or so there was an opportunity for him to lead an open door financing.

Yeah.

Mostly because he's my best friend.

Yeah.

And as I told him, like, we're going to raise money and you should lead this round. And he started asking me questions. I'm like, no, no, it doesn't work that way. I'm like, I Just set you your career. Like, your answer is how much money and at what price? Like, it's not like you don't ask diligence questions. So in contrast, to show you how this actually works is Glenn Solomon, who actually led the round from ggv, which a great. Glenn's a great investor and GGV is a great fund. Actually has known me since college, and when he heard we were doing this company, he called me up and said, can we get together? And got together. We hadn't launched Opendoor yet. And he's like, I want to preempt the next round. He's like, you know, I've known you for 29 years. This is going to work. We like real estate. You a co invested a little bit in Square, like through originally, through my connection. So they made some money. He's like, what do I have to pay to the next round? I'm like, that's why you're a good investor. And like, Jared, you're totally failing this test until you figure it out that it's not a substantive question that you want to compete. You don't want to compete on your substantive ability to look at a real estate investment. You want to compete on your ability to know Keith. Yeah, like, that's. So I do that all the time. Like, there's a lot of investments I make where founders that came from companies that I've been previously involved in, and they're starting. They want to go start their own company. They're aspirational founders, product founders, and they roll out. And I know them well enough from their experience at, let's say, square DoorDash are good examples. And my. My interest in investing is mostly based upon experience in working with them previously, not necessarily about the specific idea.

You know, I'm curious. You have this line that, you know, early days of PayPal, Peter Thiel taught you that you need to discover talent that's undiscovered because you're not gonna compete with Facebook and I compete with Google. You need to find sort of the hidden gems. So I'm curious to extend it out a little bit. How do you find people that other people have underrated and vice versa? How do you. When you see a spark in someone, how do you. Or, like, how do you find people more likable than they are good or less likable than they are really good.

Yeah. So Peter, short version is my first week working for Peter at PayPal. Like, we went for a jog around the Stanford campus, and he kind of asked me feedback how's the company doing kind of an orientation kind of reaction. And then we started talking about company building and he gave me this lesson. It was literally, you know, November 2000, we had this conversation. He's like, you have to find undiscovered, like talent. Like, you need to hire people that other people don't know how to assess. And it's like by the time you get to about 30 years old, like you have a LinkedIn at the time was a LinkedIn profile, you have a resume that almost everybody will evaluate equally. You have enough data points that anybody can run the same machine sort of on it and come to roughly the same output. So what you want to find are people that don't have enough data points for the machines that work, the recruiting machines to process. But then you still have to figure out a way to do this, which if you like sports, it's a little bit like drafting athletes out of, of let's say high school and baseball, maybe in basketball or college and football, but like being able to project from other things into a future professional role. And obviously some people do it better than others in sports. And it's similar. The hardest part is actually not. Well, the hardest part is deciding who to take like sort of a first meeting with because there's infinite number of people that one could arguably meet with and there's no really great political way to have a meeting of less than like probably a half hour. Like once you commit to meeting someone, there's, there's no way around that. And so those chunks are very expensive chunks. So you can't meet literally everybody.

Right.

So that's actually extremely difficult because by definition, if you look at the paper, the LinkedIn profile, you've just ruined the whole process. So that's, that's a one or big, huge order magnitude tasks once you meet them in person. I think it's a lot easier once you developed a little bit of this taste of is there a spark and what kind of spark are you looking for for what kind of role? Like, if the person wants a job as, you know, a job within a company, it's sort of a different spark that you might be looking for than are they a founder or do they want to be a venture investor? The criteria is a little different of what kind of spark.

Yeah, let's go one abstraction higher for anyone here in Rise, for example, or for people who come to you and say they ask you, like, hey, I just want to meet with you, like, talk about my next thing. Like, let's go to the first level of how do you pick whether someone's. What are examples of sparks that you're.

Looking for to decide to take the meeting then tip well, if they're above a certain like level of connection and been sick of Valley for a while, I'll kind of look around, see who else might know them and ask for feedback or what have they done with their time. I might look at things they've written. Like if they've certainly if they have published stuff on, you know, whether it's core medium, Twitter might look for like insights there and the indicators you're looking for.

Hey, could they be talented founder, could they be a talented, you know, person at one of your companies? Would they be a fascinating conversation or.

Yeah, like something that. But typically after someone's been in the Valley for a little bit of time, they can usually navigate themselves to me through somebody that I trust and then I'll probably take the take a meeting one way or the other. The harder one is either people you don't know or people who have just moved here.

Yeah.

And which of those people to me.

And have you met any of those that have become.

Oh yeah, yeah, yeah. I mean I found I funded a guy, it didn't work out, but I did find a guy I met on Twitter who just tweeted at me.

What was the tweet?

It was about he's got this cool startup idea. And I was like, well yeah, here's my email, send it to me and gave me a description. And the first description was okay. But then I asked a bunch of questions and the answers were better than I expected. It was in a very, I don't want to give it away the company way, but it was in a very crowded space, very complicated space. It's non trivial. But his approach and the way he was framing the problem was better than the average person in Silicon Valley would have done. So I was like, I'll take a meeting. So he came by my office. I really didn't know whether it was going to be a 20 minute meeting or an hour meeting, but came in with a prototype and passed smell tests and it wasn't an area I knew that much about. So I had to meet two of my other partners who actually do something about it. He passed their smell test. So we wound up in leading a seed investment. They wound up raising more money, but still didn't work. But so yeah, you're always looking for new ways of finding people. Occasionally I find other people on Twitter, I don't know of any or is like you know, dramatic a story is that sometimes I get. It's often an introduction from someone who knows somebody. It could be someone they've met in college though, right? There's a founder I met originally that I have funded and doing pretty well that one of my best friends went to college with. And he's like, this guy's great, you know, you should definitely meet him. I'm like, well, I'll definitely meet him. And I didn't like his idea at first, but he asked me one question. I actually tried to talk him out of his idea and then he closed the conversation with, what would I have to prove to you that would change your mind?

Yeah.

And I thought about it and I gave him two or three answers of like this, this and this. And so a month goes by and he comes back about a month, six weeks maybe, comes back and he's like, okay, I've got answers, I want to meet with you. I'm like, sure. So he sits down with a full deck, actually. It's like, here's what you said the critiques were, here's what we've been able to validate. And I was like, this is great. I want to invest. I want you to meet my partners tomorrow. Perfect. So he went from a complete no, I think you're smart and talented, but this idea is terrible to wow, I love this idea. Yeah, in six weeks.

Wow. How do you think about, by the way? I just want to give a shout out. My friend Dean in the back taught me this question. What needs to be true for you in order for you to join my company?

Yeah, it's like a version of that. But surprisingly very few people actually ask that question.

Yeah, I do. Every day.

The best question now I'm going to get this question every day. Every day. Shoot me.

Yeah, totally. Because it is kind of annoying.

Well, it's not annoying, it's just actually hard to answer sometimes. Like, it actually puts me on the spot of like reverse engineering. Okay. What are my fundamental objections to this and what are. What would actually change my mind? So it's, it's not, it's. It's non trivial often to respond.

Right.

That's why it makes my job harder. Totally.

How do you think about updating your, your priors in terms of how you think about in terms of you see someone with spark, but then you think actually they're not as impressive as I usually thought, or vice versa. You had a wrong first impression with somebody and actually they're way more impressive or interesting than you thought. How do you think about that.

Well, the first one definitely happens. I mean look, this is non zero defect. So if you're going to do zero defect hiring for your company or zero defect investing, which you really can't do, but some people do say they want to have zero defect hiring. You can't do this stuff. Like you can't hire unproven talent. You're going to make mistakes and you just have to admit that you're going to have false positives and false negatives. And it's like what's the ratio of major upside to mistakes? So definitely I've made. There's one massive mistake I made at Square, which is really funny. I literally had the whole company, like the whole company lobbying me to fire this person. This has never happened in my career before. Six weeks in like from the top down from Jack to the most junior person, every single person was like, when are you getting rid of this person? So you're clearly going to make some mistake that's actually hard to do. And this guy's paper resume is actually pretty impressive. You would never get, never ever guess it.

Did you defend this guy?

Well, for a while. But like, I mean literally I've never seen this before, like where Jack's like every day when he's getting rid of them and like you have customer support, support people asking you to get rid of the person and everybody in between. So you're going to make mistakes and you have to be willing to admit that if you're looking for high potential people that aren't yet proven founders, obviously all investors make mistakes. I mean by definition you can pick your favorite metric. But fundamentally looking for high outcome, high potential, high growth companies, if you do the canonical baseball batting average of 300 or so, you'd be close to the hall of Famer. Totally.

One more career question. We talked about what you look for or how should people should think about when they want to start a company, which is fun, they have an idea. A lot of people here are also thinking about, hey, should I either start a company, be an executive at a.

Company or join venture?

How do you recommend?

Well, I think there's a learning thing. So there's an old speech I used to give that actually Corey Levy had me give the first time a long, long time ago, which is there's different ways people learn. Some people learn better by watching and some people learn by sort of like you know, throw them in the water and they learn to swim. Each person has a different preference on that. And so for people who learn by swimming by being told they're going to drown if they don't. Founding a company is not a bad way necessarily to learn. You don't know what you're capable of and you'll pick up some skills by trying. Other people would be terrified and literally drowned or fear go freak out about drowning. And it's a very bad idea to start a company as opposed to join someone else's company that's doing well, pick up lessons, sort of write them down and apply them. So I do highly recommend the two year sort of default to join a high growth company for two years because I think you hit diminishing marginal returns and what you can learn in about two years. And then if you love the company and you love your role and et cetera, you can stay. But like it's a two year commitment to learn as much as possible, then jump out and try founding.

What about a company that was high growth but is now stagnant?

It's harder to learn because one of the reasons why you learn so much in a high growth company is the problems are changing all the time. It's like, and it's not a zero sum game of like who gets allocated different problems because there's so many and you can't hire fast enough to fix the problems. So you kind of have to give people like my, my intern opportunities because I couldn't hire someone I had support fast enough. So you wind up with like this velocity of problems and need for people to, to, to conquer them. And that's a great way to learn and get opportunity to do things you would never get to do, like traditionally. So that's why I highly recommend it. But for some people, it's a little bit like the old speech I gave back in the day to Corey's group was it's a little bit like in football. There's just two philosophies of what do you do when you draft a rookie quarterback? Some people like to play the quarterback and they clearly have the worst year of their career. Like I actually have like a chart that's every famous hall of Fame quarterback. And the stats their rookie year are terrible. They actually almost without fail all throw more interceptions and touchdowns.

Wow.

Then there's a school thought you put them on the bench for two years, they carry the clipboard around, they learn those quarterbacks actually do do better their first year actually playing. They have actually pretty good stats, but they waste two years on average on the bench that they might have been learning. So it depends. But you can find hall of Famers in both camp. Both camps very easily, actually.

Yeah. Does someone ever ask you a question of like, hey, should I join this company or should I do this? And you're like, could be interesting. But that's not the highest leverage use of your time.

Oh, definitely. All the time. Absolutely.

And what are. What commonalities are in there?

Probably that. The learning curve. I mean, it's a classic, like, learning curve. This is jargon, buzzwordy stuff. But it's maybe useful still is. Like, you want to find the steepest possible slope, and if the slope isn't that high, you're just not challenging yourself enough. And you should feel nervous about it. Like, there's an old. Another book I read when I was younger that makes this case biologically that your body reacts in a way that signals how challenged you are. So if you don't feel nervous or sweating, it means it's too easy. Like, you want to be nervous and have like, occasional sleepless nights about your work because it means you're challenging yourself to the extreme end, your body to your abilities, and your body's reacting that way. That book starts with an anecdote about Will Chamberlain, who, you know, was incredibly successful basketball player, won about 10 NBA titles. He used to throw up in the locker room, literally before every playoff game.

Wow. Is that not Bill Russell?

It was Bill Russell. Yeah, it was Bill Russell, actually. It is. So Bill. Bill won like 8 or 10 championship.

I think 11.

Maybe stop throwing up at some point. In any event, it's like, that's your. That is a healthy signal that your body's reacting to. Like, it knows it has to perform at a very high level. Right.

So a lot of responsibility, really talented people.

Yeah. People around you that push you to be better. I mean, one of the reasons why I actually like working with high energy, brilliant people is they can tell. Like Delian, for example, can tell the difference when I'm having a good day or not.

Yeah.

Like, he knows exactly, like, when I'm like, super sharp.

Yeah.

And like, when I'm adding value. And there's. Everybody has days when they're better and worse. And he can tell the difference of like. That was a pretty mediocre day.

Yeah, totally. If you're not throwing up, you're not.

Doing shit with your. Yeah. You can go to Barry's if you want to throw up.

Yeah, totally.

They give you a T shirt apparently. Yeah.

We will have Barry's question later. Okay. So for people who want to. Or exploring sort of the idea maze, want to pursue an idea you sort of have a philosophy of what lends itself to a good market or good startup idea. Can you unpack that a little bit?

Yeah, sure. So I wouldn't say it's like an exclusionary criteria. I tweeted once that there's a common formulation of a lot of very, very good companies that if you can make this magical formula align, you have a shot at building a very important company. So the basic formulation was you want an industry that has very low NPS scores, that's highly fragmented, where you vertically integrate with a simplified solution. And this is what I thought was in common mostly originally, what thought came to me is common denominator between Open Door Square, to some extent, Uber Forward Health, which is a company, like, also funded. That's the formulation. Like, incredibly fragmented industry. Nobody likes the current industry. And you're going to clean it up by vertically integrating, doing it yourself and making it therefore simple and take on the burden of having a high NPS score. So, obviously there's other companies in the world, but I think this formula works really well.

And what are other markets where you say, hey, this hasn't been done super well yet.

Somebody's. That's a great question. Because it's fragmented. I mean, not every industry is fragmented. So, for example, like, you look at airlines and. Yes, and airlines, obviously not great, but it's not fragmented at all. So it wouldn't apply to that. So I think home building, which is a little bit different than open door, there's two $20 billion publicly traded home builders, new construction companies, one called Lennar, one called something like Holden, but they still only have about 3 or 4% of the entire market.

Yeah.

So new home construction is very fragmented.

Yeah.

I don't know. The NPS doesn't seem high. I haven't, like, rigorously surveyed it, but knowing people who built homes, they don't seem very satisfied. So that might be an area. I don't know. I don't know the right answer of how to do it per se, but like, seems to fit.

If you have more questions on markets, we can leave it to the Q and A. I want to go to the last portion so we can have enough time for. For a good Q and A. So how do you think about, you know, Tyler Cowen asked this in his every podcast. He does the Keith Roy production function? Like, what makes you uniquely productive?

I think it's different, certainly different in different roles, like legal stuff versus, you know, an entrepreneurial executive roles and investing. But I've always been fairly focused on sleep it's sort of like getting eight hours sleep. Sleep. I think one day everybody's going to understand that most human problems come from lack of sleep. There's starting to be more and more evidence of this. But you need to really longitudinally study people for a long time. You need to study healthy people. Which is one of the issues is like the data hasn't been collected on healthy people and you can't run a simple linear regression of all healthy people who got eight hours sleep versus people who didn't get eight hours sleep. But eventually we're going to realize that most health conditions and most underperformance in life comes from lack of sleep. Sleep. There's a good book you can call highly recommended by a University of Berkeley professor called why We Sleep, which starts the dialogue in a pretty rigorous way. But in any event, so I've always been optimizing around sleep, which definitely helps.

Do dreams matter?

I think so because they are tied to different. There's different stages of sleep like REM sleep and sleep sleep. And I think dreams are a function of being in certain stages.

Yeah. Do you write down your dreams?

I don't.

I keep a dream journal. What do you think about earlier? The first thing you said was do things that other people can't do. So what's sort of your moat or.

What do you do that other people can't do? So it's changed over time. When I first sort of started jobs in Silicon Valley, the differentiation was more I started as a biz dev person but people thought a I was strategic, which isn't that unique. And again, people don't always define what strategic means, which is an interesting topic in and of itself, but people thought it was very strategic. But then the two elements to that was for a biz dev person, I was perceived to have decent product sense. Decent product sense. Not a product person, but decent product sense and extraordinary work ethic. Like if you read. Actually it's pretty funny exercise if you read my old LinkedIn profile still has those old endorsements from like 2003. The common denominator on these old endorsements is all extraordinary work ethic which I had learned practicing a lawyer where I lost a month as a Lawyer I billed 3500. No, that's the annualized amount last month as a Lawyer I billed 350 hours or so. And build is not worked by the way, like it's a fraction of what you work. So yeah, when I was younger I would just outwork people, but then I somehow developed some decent product Intuition, which most biz dev partnership people don't have. And so they wind up constructing partnerships that don't create the value because ultimately the users vote. User is going to still vote with their his or her feet whether to use a product integration. And so I had a decent affinity for, like, how to construct things that seem to work reasonably well and then not alienate my product team because they thought I actually understood what they did.

Let's go to the strategy thing for a second because I think it's always interesting. So by show of hands, who here thinks they don't have a good strategic scent? They're not like, like they're not really good at strategy. One person, two people.

Yeah, this is very common.

We can't all be right, we can't all be great at strategy. So what does that actually mean? Why do people think they're good at strategy? And what separates people who are actually good at strategy? People who think they are.

So I think most. I'll give you a couple tests because it comes up a lot. One is generally every business can be reduced to an equation which is like, if you tune this knob, it doesn't literally have to be math, but like, fundamentally it's a good way to think about it. Like, as you tune this knob over here, there's a knob over here and knob over here, that ultimately yields success. People who are strategic understand the connection between the knobs. So they get frustrated and you can't make this knob go past seven. They don't just keep trying to turn it to eight. They're like, well, if we turn this one over here a little bit, it might be easier and more likely to work and then that will have the same consequences as it flows through the system. It's like system engineering, systems thinker. You sometimes see Elon described that way, or Steve Jobs described that way, or Jack Dorsey described that way. It's a little bit like that. They're somewhat synonymous in my brain, in my view, but it's basically people who understand all the connections. So you can talk to someone who's a functional executive in marketing and he or she doesn't just talk about optimizing their cac, they actually can talk to you in a very educated way about all the other moving pieces of the business. And they know that, well, if I bring CAC down by this, what it unlocks for other people and other teams, whereas most functional executives can't. And so that's one version of a test. The other thing is, I highly recommend this book called Seven Powers I've tweeted about it a few times, which very rigorously defines what strategy is and isn't. And so after you've read the book, at least gives you a dialogue to have a conversation with people on your team before you're recruiting about what's strategic and what's not. So it's a good framework for having a specific conversation versus a generic, abstract conversation.

Well, another thing is judgment. I bet if that's the same thing, everyone say they have great judgment. What's like, how do you think about rating, like, what is good judgment? How do you think about rating other people? For example, if I told you that Jules is really talented, that's different than if Sam Altman tells you Jules really talented, it's different from Deli and tells you, you know.

Yeah.

How do you sort of think about who has good judgment? How do you rate people's judgment?

So, yeah, Paul Graham tweeted about it over the weekend. It was actually interesting tweet, which is on some characteristics, it's recursive in the sense that people have it can actually predict pretty accurately other people have it and some characteristics, it doesn't work. So the example he was tweeting about was if smart people tell you that someone else is smart, they're probably smart. If people who are trustworthy tell you to trust other people, that's not necessarily a prediction. So it's a little bit like that. Now, judgment's an interesting question to me. What judgment means is a little bit different. It means that the person understands how far out on a limb they actually are. So, like, as someone who's had lots of teams and stuff, and you're giving people more and more responsibility and rope. You can give people responsibility insofar as they know when to come back to you and tell you they're about to drown or they want help. The people you can't are the people who want to solve everything themselves. And they don't tell you that they're getting themselves into some deep water until it's like, too late. And then you can't help them. You can't fix it because your resources or your options are too limited. So judgment to me means understanding where you are in depth, wise and water, sort of, and being able to calibrate that pretty well so that you can rope in colleagues, mentors, advisors, board members, whoever, to help you so you don't accidentally drown.

What is your ideal day in terms of meetings? Is it two meetings a day? Is it five meetings a day? Is it 10 meetings a day.

I don't know there's a right answer because there's this trade off between energy and some attention like brain power and meetings. There's no doubt that at the end of 10 meetings I'm typically not as sharp as the first meeting of the day or second. That said, this is a business where you want to meet as many people as possible and you want to meet as many companies as possible. So there's this very fine line to me probably I try to push the envelope a bit, which is maybe about eight, possibly 10 a day of various quality and various types. So some might be board meetings, some might be interviews, some might be new pitches, some might be some random person asking for advice. But I wish I could do more. But I literally lose energy and the ability to concentrate and be able to recreate, particularly be able to, to be creative, connect connect dots like definitely to K's when I get tired.

And there's also this sort of paradox where what we do is every good meeting is too short by definition and every bad meeting is like way too long. Every 30 minute badminton is 29 minutes too long. And yet we book back to back to back.

Yeah, there's a classic overbooking problem, which is a real problem, particularly in venture. It's also true of many people just.

Convince themselves they're busy.

But yeah, it's almost like junk food, right? It's not necessarily good for you, but you feel like it's good for you. It's also a function of having executive assistance, which is a more complicated topic. So when you turn over your calendar to someone else, they are never going to have this perfect fidelity to what you're trying to optimize for. And so you wind up inheriting someone else's time allocation. And you can train to be like reasonable as an assistant for somebody, but you can't train to be the same proxy that you would do yourself. So for the longest time in my career I never had an assistant until 2012. Maybe like Jack just insisted that I get one, but I never had one in my career. And the reason why he finally forced me to get one is what he basically said to me was when people want to move meetings around with you, there's too much cognitive overload because they have to find you and they have to track you down and they don't want to interfere with you because you're busy and it creates too much disruption on other people. So you need an assistant to be the interface with people who want to shift stuff. Fair point. But then you Wind up turning over your calendar to somebody. And then you get addicted to turning over your calendar to somebody. And almost everybody in venture, there's very few exceptions, turns over their calendar to somebody. Some of my most successful venture investor friends don't. And I still try to do some scheduling myself because I can reflect priorities and I'll move things around, but there's only so much I can do.

Do you do any retroactive, like, hey, this quarter, here's where I met. Like I met with these types of people. And you calibrate this way.

I've tried to do that over the years. It's never really worked super insightfully or well. There's no good software that does this, unfortunately. And one day someone will create a calendar that has enough data that allows interesting queries, sort of, and analytics on. But I've never found a product that just works.

Right. You read a lot. How do you filter what. There's endless books you can read and, you know, history and economics and business, like sports. How do you pick what to read?

So sometimes I just go to Amazon and surf around for a while. Other times I still go to. There's a couple bookstores, real bookstores I like in the city. There's one on Second Street. There's one in Marina by Barry's. And I'll just wander, kind of wander around and like, you know, scan through the books.

Are you reading? Trying to get some. Some things out of. I'm trying to learn this. Or is it sort of more serendipity?

It's pretty serendipitous. I mean, obviously, like, there's topics that may resonate with me that are professionally, clearly useful. But like. So, for example, I found a book last week at this bookstore on Second street about the history of autonomous vehicles.

Yeah.

As a space I've invested in and I'm interested in. But I don't know the history. I mean, I know a little bit of the history, but it looked like a pretty good book. I was like, this might be useful to actually understand more about the history, what's been tried, who did what, understand more context. So I just bought it because it felt like it'd be useful. The other hand. Another book I'm reading now is called Rocket Men. Rocket Men, which is a new book about an old topic about Apollo 8, which probably doesn't have that much useful function to me, but it's still invigorating. It reminds you of how risky and how absurd, like how heroic in some ways, like putting people on to the moon was. And how now we just take it for granted. But this was one of the most heroic and adventuresome decisions that anybody's ever made in government. To actually shoot to put people on the moon and pull it off before the Russians. And it's all coming back to me now. It's kind of stuff you learned in high school, but totally forget. But I don't know how much practical impact it was have.

Last three rapid fire. Then we're going to open it up to the audience for questions. What would you do if you became the owner of Barry's Boot Camp, the brand?

Oh, we fixed the app. So, like, I don't know if you ever. Anybody who ever goes there, like, there is no app. The mobile site is unusable. Literally just running joke that I have a computer at home and the only thing I use it for is booking Barry Sessions. Because I do all my work through iPads or phones, but I need to get a computer to book. It's absurd. Let alone, like, more advanced things like social features like, oh, Eric, I'm going to Barry's today. Where are you going? What class? Are you going to share my schedule, Sharing my spot, or, you know, rewards. You know, there's so many things, but I would definitely innovate there. I think they do a great job on the programming, on the instructors and music, you know, all the experience parts. But the technology part is like, well below things like Soul Cycle, let alone, like, where it could be.

Yeah. I pinged Keith every two weeks saying we should own a part of a Barry's Boot Camp franchise. Which is. Which is why I asked the subliminal. Subliminally, how about if you own the New York Knicks?

Oh, that's a mouse. So, you know, the Knicks basically haven't been any good with one exception, you know, for about a year since, like 2000. So, like, think about it and you forget as you grow up, like, this is like, means basically one or two generations of basketball fans have never had a good Knicks team. So I grew up in, you know, more the 80s and 90s, when Knicks are actually pretty good. So I think you just have to change the ownership structure. Change owner, owner is the biggest problem. And, like, rebuild from scratch. Like, is just tear everything to shreds and, you know, hope to build a new foundation. Yep.

Last question. If you look at your life 5 years out, 10 years out, 15 years out, do you see sort of like new big chapter that's on a quote unquote, like, bucket list of. Of achievements, or is it more like, hey, 12 IPOs or whatever it is. Let's get to 20 or how do you think about looking at it?

I think the default is to stay on some version of the current trajectory. But that doesn't necessarily have to mean investing per se, because you could debundle advising and investing at some point, maybe the world. There's no inherent reason why mentoring and advising is bundled with capital. At some point they could debundle, but. But I think that's the default path. Could something sort of out of left field in sports or politics intrigue me?

Maybe like owning a team?

Yeah, it's a very expensive hobby.

Part of a team.

How about the Barry's Boot Camp?

Yeah, sounds good. Or politics?

Yeah, I mean, I used to have a lot of interest in politics. Like most lawyers and certainly D.C. lawyer types. I don't know if I'd actually do that. I did enough to remember the things I don't like about it. So I think there's this grass is greener element to most people's decision making. And my grasp on politics isn't so green. I remember enough of like what reality is. So I'm not like artificially tempted to go back. But, you know, would if one of my friends or something became like very successful in politics and needed a chief of staff, would I do something like that? Maybe so it'd be something like, you know, out of left field that I wasn't planning.

Perhaps Peter too.

I don't know. If you can get him to run for something. Good luck with that.

Yeah, totally. Guys, can we please give a round of applause for Tanker boy? Turpentine VC is a podcast from Turpentine.

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