E72: Keith Rabois: On Identifying Talent [Classic Interview]

22:07But 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 the diversity of skill set? I'll sort of admit that I would suck at the smoothie test. You already know because you know me. 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? 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 his skill set.

22:42Or you might have a feel from an experience or resume or LinkedIn profile where to look. Yeah. But you're basically – that's why I was talking about Twitter. It's not like – I don't actually read everybody's Twitter profile that applies for jobs. But if I see something, then I go try to figure out what this person is excellent at and what that job could be. 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 at a 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.

23:18and 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'd 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 metocratic, 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 U.S. tax code. And trust me, as someone who went to law school, the tax regs are not particularly fun to read.

23:47around real estate, in fact, particularly not fun because they're quite complicated. And he mastered them. 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, 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 100 people. And again, imagine he's like 22 years old and most people investing in real estate are a lot older.

24:21Like 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, at 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. Yeah. So then the final conversation about – so the first job I sent 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.

24:48But then Slide, when I joined Slide, I had another possible job. So I was thinking about it, but this was a little bit more producty BizDevi, which is a little bit more stretched 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 for 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 like this conversation going on in my brain as he's answering.

25:20I'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, literally the second, maybe the 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. You're adopting new products and technologies. I'd been on the board of Yelp at the time. So I knew all 10 Yelp Elite users actually. But I was like, that's showing another signal that this person who has nothing to do with technology has a pretty good radar for new and up-emerging things.

25:59And 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 – not to bring myself into it, but 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 had seen me in a context where you have to remember as a U.S. tax code or something, it would have been like, you know, no way.

26:29And 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 are you going to be the one person or how are you different than everybody else who 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.

27:00But venture is a different – like I actually knew that he was going to struggle with venture because 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 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, no. It doesn't work that way. I'm like, I just set your career up. Yeah, you would have made it good. Like your answer is how much money and at what price. 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 is great.

27:33Glenn is 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 we got together. We hadn't launched Open Door yet. And he's like, I want to preempt the next round. He's like, I've known you for 29 years. This is going to work. We like real estate. They co-invested a little bit in Square, like, 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.

28:03And so 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. 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 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 or DoorDash are good examples.

28:31And my interest in investing is mostly based upon experience and working with them previously. Yep. 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 going to compete with Facebook and I can compete with Google, I 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 over like more likable than they are good or less likable than they are really good?

29:07Yeah. So Peter short version is my first week at working for Peter at PayPal. Like we went for a jog around the Stanford campus and he kind of asked me, you know, 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 November 2000. We had this conversation. He's like, you have to find undiscovered talent. Like you need to hire people and other people don't know how to assess. And he's like, by the time you get to about 30 years old, like you have a LinkedIn – At the time it was a LinkedIn profile.

29:35You 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, 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.

30:06And 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 an 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 half hour. Like once you commit to meeting someone, 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.

30:44So that's a one-order, big, huge order of magnitude task. Once you meet them in person, I think it's a lot easier. Once you develop 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 a job within a company, it's sort of a different spark 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 like, hey, I just want to meet with you.

31:20Like 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? Well, if they're above a certain level of connection and been in Silicon Valley for a while, I'll kind of look around and 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. Certainly, if they have published stuff on, whether it's Quora, Medium, Twitter, might look for insights there. And the indicators you're looking for, hey, could they be a talented founder?

31:51Could they be a talented person at one of your companies? Would they be a fascinating conversation? Yeah. Yeah, something that – but typically, after someone has been in the Valley for a little bit of time, they can usually navigate themselves to me through somebody that I trust. Then I'll probably 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 and wish of those people to meet. Have you met any of those that have become – Oh, yeah, yeah, yeah. I mean, I funded a guy. It didn't work out, but I did fund a guy I met on Twitter who just tweeted on me.

32:26What was the tweet? It was about he's got this cool startup idea. And I was like, well, here's my email. Send it to me and he 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 out of my office.

32:57I really didn't know whether it was going to be a 20-minute meeting or an hour meeting. But he 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. Yeah. They actually do something about it. He passed their smell test. So we wound up 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 as dramatic a story as that. sometimes I get, it's often an introduction from someone who knows somebody.

33:28It could be someone they met in college though. Right. Like 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. Right. 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 or about a month six weeks maybe comes back is 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 Yeah.

34:19And I was like, this is great. Like, I want to invest. I want you to meet my partners tomorrow. You know, like, perfect. So he went from a complete no, like, 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 X, join my company, take my money? Yeah, it's like a version of that. Totally. But surprisingly, very few people actually ask that question. Yeah. I do every day.

34:48That's the best question. Now I'm going to get this question every day. No, don't the cap. Shoot me. Yeah, totally. Because it is kind of annoying. Well, it's not annoying. It's just actually hard to answer sometimes. It actually puts me on the spot of reverse engineering. Okay, what are my fundamental objections to this? And what would actually change my mind? So it's not trivial often to respond. Right. It's why it makes my job harder. Totally. How do you think about updating your priors in terms of how you think about – in terms of you see someone with a spark, but then you think, actually, they're not as impressive as I actually thought.

35:16Or vice versa. that 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. You can't hire unproven talent. You're going to make mistakes. 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?

35:44So doubtfully, I've made, There's one massive mistake I made at Square, which is really funny. I literally had the whole company lobbying me to fire this person. This has never happened in my career before. Six weeks in, from the top down, from Jack to the most junior person, every single person was like, when are you getting rid of this person? You're clearly going to make some mistakes. That's actually hard to do. This guy's paper resume is actually pretty impressive. You would never, ever guess it from paper. Did you defend this guy? Well, for a while. Literally, I've never seen this before.

36:14where Jack is like every day when he's getting rid of him. And like you have customer 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. Yeah. Founders, obviously, all investors make mistakes. I mean like by definition, you can pick your favorite metric. But fundamentally, looking for high outcome, high potential, high growth companies, Because if you do the canonical baseball batting average of 300 or so, you'd be close to the Hall of Famer.

36:47One more – I'm going to make your career question. We talked about what you look for or how people should think about when they want to start a company, which is when they have an idea. A lot of people here are also thinking about, hey, should I start a company, be an executive at a company, or join venture? How do you recommend that? 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.

37:17Like 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 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 on what you can learn in about two years.

37:56And 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. And 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 are so many. And you can't hire fast enough to fix the problems. So you kind of have to give people like my intern opportunities because I couldn't hire someone who had support fast enough.

38:26So you wind up with like this velocity of problems and need for people to conquer them. and that's a great way to learn and get an 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 has every famous Hall of Fame quarterback and the stats, their rookie year are terrible.

39:01They actually almost without fail, all throw more interceptions than touchdowns. Then there's the 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. But you can find Hall of Famers in both camps very easily actually. Yeah. Does someone ever ask you a question of like, hey, should I join this company or should should I do this? And you're like, could be interesting, but that's not the highest leverage use of your time.

39:32Oh, definitely. All the time. Absolutely. What commonalities are in there? Probably the learning curve. I mean, it's a classic learning curve. This is jargon, buzzword-y stuff, but it's maybe useful still. It's 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 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.

40:06Like 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 of your body, to your abilities and your body's reacting that way. That book starts with an anecdote about Will Chamberlain, who was an 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 on Bill Russell? It was Bill Russell. Yes, it was Bill Russell. Actually, it is. So Bill won like eight or 10 in the championship. I think 11. Maybe 10. Maybe stop throwing up at some point.

40:38Maybe 10 or 11. In any event, it's like that is a healthy signal that your body is 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 Dullian, for example, can tell the difference when I'm having a good day or not. He knows exactly when I'm super sharp and when I'm adding value. Everybody has days when they're better and worse. He can tell the difference of like that was a pretty mediocre day.

41:11Totally. If you're not throwing up, you're not doing shit with yourself. Yeah. I'm just kidding. You can go to Barry's if you want to throw up. Yeah, totally. They give you a t-shirt apparently. We will have Barry's question later. Okay. So for people who are 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.

41:48So 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 I thought came to be is common denominator between Open Door Square, some extent Uber, Forward Health, which is a company like I 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.

42:24So 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? That's a great question because it's – I mean, not every industry is fragmented. So for example, like you look at airlines, NPS 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 Opendoor. There's two$20 billion publicly traded home builders, new construction companies, one called Lenar, one called something like Holden.

42:53But they still only have about 3 % or 4 % of the entire market. So new home construction is very fragmented. The NPS doesn't seem high. I haven't 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 the right answer of how to do it per se, but seems to fit. If you have more questions on markets, we can leave it to the Q &A. I want to go to the last portion so we can have enough time for a good Q &A. So how do you think about – Tyler Cowen asks this in every podcast he does – the Keith Roy production function. What makes you uniquely productive?

43:31I think it's certainly different in different roles like legal stuff versus an entrepreneurial executive roles in investing. But I've always been fairly focused on sleep. It's sort of like getting an eight-hour 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. The data hasn't been collected on healthy people, and so you can't run a simple linear regression of all healthy people who got an 8-hour sleep versus people who didn't get an 8-hour sleep.

44:07But eventually, we're going to realize that most health conditions and most underperformance of life comes from lack of sleep. There's a good book you can call – I highly recommend by a University of Berkeley professor called Why We Sleep, which is 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?

44:36I don't. Yeah. 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 business 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 I was very strategic. But then the two elements to that was for a biz dev person, I was perceived to have decent product sense.

45:15Decent product sense. Not a product person, but decent product sense. And extraordinary work ethic. Like if you read – actually, it's a pretty funny exercise. If you read my old LinkedIn profile, it still has those old endorsements from like 2003. The common denominator on these old like endorsements is all like extraordinary work ethic, which I had learned practicing a lawyer where I last month as a lawyer, I billed 3 ,500 – no, that's the annualized amount. Last month as a lawyer, I billed 350 hours or so. And build does not work, by the way. It's a fraction of what you work. So yeah, when I was younger, I would just outwork people.

45:56But then I somehow developed some decent product intuition, which most business partnership people don't have. And so they wind up constructing partnerships that don't create the value because ultimately the user is going to still vote with 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 a show of hands, who here thinks they don't have a good strategic scent?

46:27They're not 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? What separates people who are actually good at strategy from people who think they are? So I think most – I'll give you a couple of 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 fundamentally, it's a good way to think about it.

46:56as you tune this knob over here, there's a knob over here and a 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.

47:27It'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.

48:01I tweeted about it a few times which very rigorously defines what strategy is and isn't. And so after you've read the book, it 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. Another thing is judgment. I bet if I asked the same thing, I would say, make great judgment. How do you think about rating? 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 is really talented, that's different from Delian tells you.

48:38How do you think about who has good judgment? How do you rate people's judgment? Paul Graham tweeted about it over the weekend. It was actually an 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 in 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. Interesting. So it's a little bit like that.

49:09Now, judgment is 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.

49:44And 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 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 that 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 yeah and meetings like there's no doubt that at the end of 10 meetings i'm typically not as sharp as like 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.

50:49So 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 be creative, particularly be able to be creative, to connect dots, like definitely to Kate. when I get tired. 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 bad meeting 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.

51:27It's also true of many sex. People just convince themselves they're busy but… Yeah. It's almost like junk food, right? I mean, it's not necessarily good for you, but you feel like it's good for you. It's also a function of having executive assistants, which is a more complicated topic. Yeah. 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.

52:03So for the longest time of my career, I've 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 like 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.

52:35But 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. Yeah. Like because I can reflect priorities and I'll move things around. that there's only so much I can do. Do you do any retroactive like, hey, this quarter, here's where I met. I met with these types of people and I should calibrate this way. I've tried to do that over the years.

53:05It'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 in analytics. But I've never found a product that just works. Right. You read a lot. How do you filter what – there's endless books that you can read in history and economics and business, like sports. How do you pick what to read? Sometimes I just go to Amazon and surf around for a while. Other times I still go to – there's a couple of bookstores, real bookstores I like in the city. There's one on Second Street.

53:39There's one in Marina by Barry's. I'll just wander, kind of wander around and scan through the books. Are you reading trying to get 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. Yep. 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.

54:14I 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. On the other hand, another book I'm reading now is called 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 and how heroic in some ways putting people onto 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 has ever made in government to actually shoot to put people on the moon and pull it off before the Russians.

54:58It's all coming back to me now. It's kind of stuff you learn in high school but totally forget. But I don't know how much practical impact it will have. Last three rapid fire and then we're going to open it up to the audience for the questions. What would you do if you became the owner of Barry's Bootcamp? Oh, we fixed the app. So like I don't know if anybody who ever goes there, like there is no app. The mobile site is unusable. It's like literally just a 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.

55:29But 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? Sharing my schedule, sharing my spot. Or, you know, reward. There are so many things, but I would definitely innovate there. I think they do a great job on the programming, on the instructors, the music, all the experience parts. But the technology part is well below things like SoulCycle, let alone where it could be. I ping Keith every two weeks saying we should own part of a various boot camp franchise, which is why I ask this subliminally.

56:08How about if you own the New York Knicks? Oh, that's a mess. 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 in the 80s and 90s when Knicks were actually pretty good. So, I think you just have to change the ownership structure, change the owner. The 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 uh if you look at your life five 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 do you is it more like hey 12 ipos or whatever it is uh you know let's get to 20 or how do you think about looking 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.

57:11There's no inherent reason why mentoring and advising is bundled with capital. At some point, they could debundle. 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. Or part of a team. Have a various 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 DC 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 elements in most people's decision making.

57:49And my grass 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 if one of my friends or something became very successful in politics and needed a chief of staff, would I do something like that? Maybe. So it would be something 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 your people?

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