Keith Rabois: On Identifying Talent [Classic Interview]

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.

Well, yeah, I mean, now, I mean, 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 backgrounds. So Brian Grassadonia ran Square Cash and done phenomenally well at Square, worked for me at Slide and then came over at 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? 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, the jargonistic term is 'strategic,' but actually developed an ability to be perceived as strategic. And that allows you to be promoted from a functional executive to a senior executive. And we can talk about what that means, but all three of those are really good examples.

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 Grassadonia 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 me as like the 22nd employee, I guess, at Square.

Good, now we can talk about it. Yeah, priorities, totally. So in true Keith Chief of Staff fashion, so if he... wait, he's 23? He's 24. 24. So let's say he had done his tour of duty as Chief of Staff and 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 were having dinner and we were talking about maybe I should hire a friend of his as my Chief of Staff. That's the... 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 like furiously, it'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 found an apartment. So short bio, but basically was a Thiel Fellow, dropped out of MIT, then went to YC, did his own startup, and then joined 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 of 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, when he was having a drink here, everybody when you drop out, like he was an MIT engineer, so we 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 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 the goal was to learn how to evaluate people. And so he shadows me around most of the day and he comes to board meetings with me. And immediately a month or two in, he could tell what the differences are. He comes to interviews with me when I interview candidates, and usually I'll actually ask him for his feedback before I tell him what 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. This 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 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. Classic example is you want to hire a CFO. Most people who are young and technical or designers and young don't know CFOs. They have no idea what a CFO even does, let alone 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 hundreds probably, and so I could help assess a CFO candidate if that's what your business needs. Not every business needs a CFO very early, but some do. 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 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.

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' philosophy of life. Even 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 you can ask to test your ideas. You may have an idea, like I'm pretty excited about X, but is it really a good idea? And that's a reasonable process to go through before you recruit people to your team, before you raise capital, before you commit extra of your 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 Delan came to you and was like, 'I want to be a founder,' he would then hopefully have a specific idea that he just can't stop, can't get sleep at night about. Like literally in the proverbial, 'I can't sleep.' 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. And then you're like, 'Okay, now what are the barriers to success for this idea? What kinds of people and market and 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 instrumental 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 a showstopper. 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 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, Delan 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 do for the next 50 years of their life. Want operating experience, build something, try something. I think there's a lot of reasons for it, but obviously be intellectually curious. Venture is 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 healthcare. I joined Khosla 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 well-run. And you could read stuff in the media about issues with healthcare, but I had no idea about solutions and why there were no solutions. So I just started meeting people in healthcare and started investing in healthcare. And now probably 20-25% of all my investments are in healthcare. And that's what I get paid to do: 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. 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 amazing people that challenge me. The questions they ask me every day are the hardest questions ever, because if it was easy, they wouldn't ask the damn question. So when a founder who we funded walks into 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, you know that you've just made someone's eyes light up in a serious way. It's totally rewarding. So there's not that many jobs where you get to do those two things.

I mean, I think the learn-to-earn 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, a year, a decade, whatever, 20 years for some people. Whereas I think in society 50 years ago it was 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 your 30s, you still couldn't do—like law still works this way. Like I grew up as a lawyer. People I went to law school with, people I clerked with, are now at the prime of their legal career. They're getting appointed Circuit Court judges, and I wouldn't be surprised if some of my friends wind up on the Supreme Court someday. But they're now getting in the zone, whereas for me it's getting towards the end of my career. So law just is a hierarchical, 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 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, 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. It could come right away. The brand could 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.

So example recently, you look at my Twitter feed, you'll see about maybe a month ago I tweeted this thread that I found about China. And I was like, 'This is the most insightful thing I've read about China in like 5 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. 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 sent it to 150,000 people. And so he's like, 'Thank you very much. By the way, I'm this New York high school student, 18 years old.' So but the point was that there was a spark there that lots of people write 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 help him reasonably well if he can do it once every five years. But if he can regularly write something interesting and clear on a topic that lots of people care about, people will—the network will exist. People will definitely—so then he sent me an email, he's like, 'Hey, I'm going to be in the Bay Area, would you meet me?' I'm like, 'Of course.' If he had sent me the same email a month earlier, there's no way I would have met him.

Well, people will take meetings. So for example, or jobs. So you guys may know Sean Rose. Yeah. So originally I met Sean on Twitter and he was just tweeting these interesting things. So I kind of looked up his bio and so he 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 Adventures.' But I was actually serious. I was like, I could tell from reading 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 oversupplied with content—like lots of people tweet, lots of people talk about technology—but you could see that he had a gem of an eye for things that other people were missing. Or same thing, my co-founder at Opendoor, Ian—some of you may know Ian Wong—worked for me at Square. But basically he was the first data scientist at Square. I met him at a party, a cocktail 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 joining 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?' I was like, 'Well, you just told me your bio.' So he's CS undergrad at Stanford, got a master's in statistics, and was getting a PhD in EE, and been an intern at Facebook. I was like, 'If I can't find something for you to do at Square, it's my problem. Someone with that bio, we absolutely have a need for because we do hardware, software, CS.' So it was like a no-brainer. But it was also then I also could read all his Quora answers and he'd written a decent amount. So I could see how his brain worked. So it was much better than like a 20-minute interview in terms of figuring out what he actually understands and what he doesn't.

That's a great question because it doesn't scale. I mean, the truthful—it scales better in an organization, truthfully, than it does in venture. In 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 go randomly rotate. In venture, it's harder to do that. So I found it's more difficult. I ask, 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 they asked, and the presentation just came out pretty well. And they asked if they could broadcast it, and I said yes. But I had 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 like never hired business interns. I always believed either designers or engineers are interns, but you don't want to hire business interns. But he talked me into hiring him. 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 Sheryl. 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 9:00 p.m.? Because the engineers are 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 energy. 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, etc. 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. Like, try, good luck. So all of a sudden 9:00 rolls around and these perfect smoothies, like with the right flavors, variety, show up, all cold, delivered to the right spot in the office. And I'm like, 'Holy, this actually worked.' And so what I thought from that, I was like, 'Oh, this kid's talented,' even though he did this ridiculous task. And so I just kept giving him more complex and more important projects to the point that I actually offered him the job of running our support team if he wanted to. Turns out he decided to go back to school. But in any event, that's what you do: you're looking for this 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—this is something David Sacks 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.

Well, 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. Or you might have a feel from experience or resume or LinkedIn profile where to look. But you're basically looking—that's why I was talking about Twitter. It's 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's excellent at and is that what that job could be. Yeah. 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, was basically selling tax shelters or advising people on tax shelters. And he was very frustrated because he had 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'd go to dinner, he'd just be frustrated. I got sick of listening to him be frustrated at dinner. So I'm like, 'You don't have to do this. In tech, it's more meritocratic,' blah blah blah. So I eventually convinced him to consider tech. But what stood out to me was the 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 because they're quite complicated. And he mastered them. He knew his real estate tax at least as well as I did with a very fancy Harvard Law education. And so that was pretty impressive. I'm like, think about what that means: rapid learning curve, ability to learn a topic that people study for years. Secondly, very boring topic, so discipline, self-ability to motivate yourself for things that are not fun. And then I went to watch—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. You're talking 40s, 50s, 60s, maybe 70s, the audience. And he did this presentation for like 100 people and just had total command of the audience. So I was like, at a minimum, you can do sales. So I'm 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—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 product-y, biz dev-y, which was a little bit more stretched from the things I'd already seen. So I remember talking to him about it 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 over 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—remember, this conversation going on in my brain as he's answering it—I'm like, 'For an amateur, that's actually quite a 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 third, second, or third Yelp Elite user. And I was like, 'Well, that's pretty interesting. Like 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 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, he could learn to do this for a living.'

Yeah. So venture's 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 operating stuff where he actually does have some competitive advantages. But venture is a different—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 Opendoor 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. Your answer is how much money and at what price. It's not—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 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 we got together. We haven'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.' They co-invested a little bit in Square originally through my connection, so they made some money. He's like, 'What do I have to pay to lead the next round?' I'm like, 'That's why you're a good investor.' Going to Jared, you're totally failing the test until you figure 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, prototypical founders, and they roll out and I know them well enough from their...

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, 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, this literally, you know, November 20th, we had this conversation. He's like, you have to find undiscovered talent. Like you need to hire people that other people don't know how to access. And he's like, by the time you get to about 30 years old, like you have 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 comes 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 athletes out of, let's say, high school in baseball, maybe in basketball or college in 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 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 a half hour. Like once you commit to meeting someone, there's no way around that. And so there's 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 a one or big huge order magnitude task. Once you meet them in person, I think it's a lot easier once you've 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 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.

Well, if they're above a certain like level of connection and been in Silicon 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 certainly if they have published stuff on, you know, whether it's Quora, Medium, Twitter, might look for like insights there. And the indicator you're looking for, hey, could they be a talented founder, could they be a talented, you know, person at one of your companies, would they be a fascinating conversation or something like 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 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 which of those people to meet. 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 fund a guy I met on Twitter who just tweeted at me.

Um, 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, um, I don't want to give it away the company, but it was in a very crowded space, very complicated space. It's non-trivial, but his approach and, um, the way he was framing the problem was better than the average person and stuff would have done. So I was like, I'll take a meeting. So he came out to my office. I 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 who actually do know 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 if any are as like dramatic a story as that. Sometimes I get, it's often an introduction from someone who knows somebody. It 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, 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?

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 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, like I want to invest, I want you to meet my partners tomorrow, you know, like perfect.

Yeah, I do every day. The best question. Now I'm going to get this question every day. Every no doesn't count, shoot me. Um, yeah, totally. It's 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 would actually change my mind. So it's non-trivial often to respond, right? It's why it makes my job harder.

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, um, 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 like 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? Um, so you're clearly going to make some mistakes. That's actually hard to do. And this guy's paper resume is actually pretty impressive. You would never guess it.

Well, for a while, but like, I mean, like literally I've never seen this before, like where Jack's like every day, when are you 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 clearly going to make mistakes, um, 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 know, you pick your favorite metric, but fundamentally looking for high outcome, you know, high potential, high growth companies. If you do, you know, if you do the canonical baseball batting average of 300 or so, you'd be close to the Hall of Famer.

Well, I think there's a learning thing. So there's an old speech, um, I used to give that actually Cory 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. Like 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 drown or, you know, 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, you know, sort of write them down and apply them. So I do highly recommend the two years sort of rule to join a high growth company for two years because I think you hit diminishing marginal returns in what you can learn in about two years. And then if you love the company and you love your role and etc., you can stay, but like it's a two-year commitment to learn as much as possible, then jump out and try founding.