#274 Keith Rabois: One of Silicon Valley’s Most Influential Investors and Operators in His Most Personal Conversation Yet

Hi, I'm Vidit, the founder and host of this podcast, The High Flyers.

Hi, I'm Keith Rabois, MD at Khristal Ventures.

Keith, I'm thrilled to do this. I feel like the obvious question is, you do so many of these interviews, what would make this your favorite interview?

Well, I love interviews that cover unexplored topics. Obviously, I've done a lot of interviews over the years, and yes, my views do change over the years, and there's always emerging technologies and new trends to talk about. But I find the ones that are most interesting is when people ask questions that haven't been asked before, and then there's new content All right, that is my goal out of today.

You know what's been— what my interesting reflection was the other day? Like, you and I have got to know each other a bit and we've talked on emails a bit and we're planning a small event soon. You are really warm and friendly and easy to chat to one-on-one, but I think people on Twitter might see you and be like, oh, I don't know if I wanna approach this guy. Do you get that? Do you get that often?

I get the question a lot. I think it's a misleading question. You know, I think like I went down this Fool's rabbit hole of trying to correct every wrong view on the internet and most of it's on X. Which is probably a bad crusade to bite off. But there's a lot of fools on the internet. There's a lot of fools in the world, and it's an unhelpful, probably, passion. The good news is founders are a lot sharper, more ambitious. And so when I meet people in the tech sector, they're typically much more on target with a lot less ridiculous views than the 8 billion or whatever people on the planet. Yes. But one of the things I do do though, that is representative of, I try to respond to most tweets or posts at me on X and engage in a dialogue as long as someone's not I'm not a ridiculous troll. So I try to always be helpful whenever I can, and correcting people's views hopefully changes their life in a positive direction.

Yeah, I mean, hopefully you'll correct some of my views today. We'll see how we go.

We'll see.

Hey friends, welcome back or welcome to the High Flyers Podcast, where we do reimagine a high flyer, showcase the brightest and most relatable role models and companies, and their journey from sunrise to today. As one of the premier products in our Curiosity Center lineup, providing on-demand intelligence to help you be 1% better every single day. I'm your host, Vidit Agarwal, and let's have some fun. Our listeners have called this podcast a meticulously researched biography unveiling the extraordinary lives and decisions of the most remarkable individuals and companies from around the world. We hope you're enjoying our catalog of 200+ episodes since we launched in 2020. With many of our guests appearing in rare public interviews, it's now time to explore your curiosity. Please enjoy.

Let's set some context with some fun facts. Where were you born and where do you live now?

I was born in Edison, New Jersey. For those of you who've commuted up and down the Eastern Seaboard, Metro Park train station is right there. It's probably the easiest way to find it. It is the original home of Thomas Alva Edison, renamed after him. And then Menlo Park originally, which is funny that I now work also in Menlo Park. I spent all my life chasing Menlo Parks around. And then I mostly travel a lot now. I spend a lot of time in New York. I spend some time in DC, some in the Bay Area, San Francisco, and some in Miami. And so in any given month, I'm in all 4 cities. I also don't recommend that for most people either.

It's one that I think about because I travel a lot overseas, whereas yours is more in the US. I actually read something the other day that if we travel a lot, it's bad for our skin. I'm sure you've read about that.

Uh, I don't know how true it is, but it makes sense for lots of reasons. I do find that there are certain cities that my skin really likes and certain cities that the skin gets aggravated in, but I don't know if it's travel or humidity or, you know, some other variable.

And tell me, work— what was your first job and what do you do now?

My first job officially, like as a full-time employee, was as a law clerk for the United States Court of Appeals. for the Fifth Circuit of the United States, working for the Honorable Edith H. Jones. And now I'm a venture capitalist. Again, not a path I'd recommend to most people.

And Keith, as you know, the purpose of this show is to reimagine a high flyer. Is there a high flyer you know who you feel hasn't got the recognition they deserve?

Well, I think I would recast that a bit. I think there's people with high potential and that will likely be high flyers. I think of the people who are already flying, high altitude. Most of them are pretty well recognized. There's a lot of interest in tech from legacy media, from podcasts, from new media. So I think it's hard to stay sort of undiscovered, but I think the art is finding people and identifying their abilities before they've demonstrated with work product. So, you know, one of the predictions and prognostications and Quora posts I'm most proud of is in 2010, I was asked, who are the people you would fund under any circumstance, sort of regardless of what idea they were chasing? And I listed about 8 people. That one looks pretty good in retrospect. Remember, this written in April, I believe, of 2010. It was Sam Altman, Daniel Gross, and a bunch of other pretty good calls. So Brian Chesky. So that's the hard part and the hard part of venture capital as well. I'm not sure I have anybody that I think is already magnificent but doesn't get attention.

Well, I was going to say, even your angel investments, your first 5 angel investments were all like home runs, right?

I know I should have quit then. I thought it was easy. It was like YouTube, Palantir, this company called Zoom, which went public before was acquired by PayPal, and there was a 4th one that was pretty good too.

Yeah, we just released an episode today with Kevin Hotz.

Oh, cool. So yeah, so Kevin, you know, co-invested in several of those companies with me, and Kevin really started me down my career in tech. He was one of the more instrumental people in persuading me to leave the practice of law, which I alluded to as a law clerk and as a litigator. Kevin was pretty persuasive, and fortunately I returned the favor and helped him invest in PayPal, which sort of helped his career trajectory start. But He really deserves a lot of credit for rescuing me from law.

Yeah, you connected me to Jeff Donecker for research as well, and he gave me some interesting answers.

Jeff deserves even more of the credit. Jeff was my first manager in tech, which I'm sure he told you all about. Lots of fun.

He did.

I feel like he was specifically— He probably told you about these amazing spreadsheets I created.

You know what he did tell me, and you and I were joking about this the other day, is that apparently you would drink 6 Diet Cokes in a board meeting. Like you would bring—

that's probably true. Well, if you had to attend, the company was called voter.com back then. If you had to attend voter.com board meetings, you would drink 6 Diet Cokes as well.

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Let's go back to Edison, New Jersey. And this one's particularly interesting because people haven't really asked you about your upbringing. Like, you've talked about it a bit here and there, so I'll see how far we can get into this. I feel one thing that came up a bit in my research is your parents. People said like your parents are very different to you, but of course have shaped you. Can you reflect on that?

Yeah, I mean, my parents were kind of classic I guess sort of parenting Middle America. So my dad was a CPA by training, an accountant. My mom was mostly— most of her career was like a teacher, English, social studies. So, you know, not related at all to anything I wound up doing in law and technology. My dad is extremely introverted. My mom's more social and maybe some somewhere in the middle. I am much more introverted than people guess, but I'd say my dad's on the extreme scale. So at least maybe my mom pulled me a little bit this way. And they were very academically focused. They met originally at University of Michigan as students. And so, you know, there was a high premium on academic success in the household. I have a younger sister who also followed me to college. So really it was a traditional sort of middle-class Jewish household, you know, get good grades, study, no excuses kind of, but not particularly unique, at least in many ways that I remember.

What did you inherit from each of your parents?

I'm actually, surprisingly, I'm actually a pretty good subtle salesperson and I ran away from it because my mom, when she quit teaching because of problems in the public schools and she just didn't want to deal with a lot of them, became fairly effective as a sales manager. And I think I picked up a lot of skills that have come in handy, even though like many ambitious, highly educated or overeducated kids, I ran away like the plague from the title sales. And I remember in college I had this friend named Chris who went to Stanford with me. And I was kind of denying that I ever would do anything related to sales. And Chris looked at me and he said, he's like, Rabois, you're like the greatest little salesman ever. And I was like, oh, that's interesting. And then, you know, sort of helped me think about it as maybe a skill or a talent versus like something to run away from. But I think I probably picked up some from her. I definitely also picked up reading more from my mom than my dad. I was a voracious reader growing up, which we could talk about in detail. As she likes to describe, I read the encyclopedia cover to cover. You know, I'd come home from school every day. and read a different volume of the encyclopedia, but I'd read all kinds of fiction, spy fiction, Jean le Carré kind of stuff, Ken Follett. And I picked up that through my mom and my grandma more than like my dad's side of the family. And then I probably picked up more from my dad. I have a pretty good ability to not get too caught up in something and kind of let the dust settle a little bit and just ignore the volatility. And my dad's very reserved and very calm. And so that was probably, that's probably useful.

Tell me about— I read in one of the interviews you did, you described yourself as a high-credentialist kid. I think you were seeking— I was.

Yes.

Is that, is that right? I guess.

Oh yeah, I definitely wanted like the highest grades, go to the best schools, all the things that you're not supposed to do. Uh, you know, my, my friend and longtime colleague Peter Thiel used to always make fun of me for being too credentialist sort of along the way. He got off the addiction before I did. And so I went to Stanford, then went to Harvard Law School, and then I clerked for a federal appellate court judge, which is exactly what you do. I worked for Sullivan Cromwell, which is the elite of the elite Wall Street law firms. It's like the central casting. So I was on this perfect credentialist journey, and then I quit it all very cold turkey in February 2000 to join a startup, this one called Vodra.com, when Jeff hired me that no one Other than maybe 10 of us will ever remember. I didn't do anything related to the practice of law. I quit cold turkey. I just did pure business stuff, business strategy, partnerships, customer acquisition, all of that stuff, and had to learn content, content strategy, financial modeling, which I never really learned, as Jeff, I'm sure, told you all along the way. So for the first 29 years of my life, I was on the classic This is what you're supposed to do. Earn the next grade, earn the next medal, silver medal, gold medal, whatever.

I've also heard you say that your high school friends would never have guessed you'd end up in tech. Is that true?

That's very true. I think law and politics were very obvious fits for me since I was in 6th grade. Pretty committed to like the law and politics hybrid, you know, career, which is a pretty common combination. I did programs. Maybe if they had to be, if you were probing them, the only flash they might have seen is I did program in high school. I did take like AP Computer Science and things like that. I did actually write a high school, actually in junior elementary school, actually wrote a program to organize our class schedule. We used to use these punch cards or whatever, you know, something awful like that. And my dad had an early, and this is probably also really important stuff I picked up from him. He had a very early Apple II, which he used for work. Accounting because it was one of the early use cases, but also you could use it for games. And I kind of learned to program some basic double entendre stuff. And I actually was annoyed with the school scheduling and calendaring enough that I wrote a program for all the kids in our 4th, 5th, and 6th grade school. So maybe there were these little super early signals, but it's one of those Steve Jobsian lines of you can only really connect these dots with hindsight. I don't think anybody would've connected them at the time.

And tell me about soccer, which I was surprised, like even your Gmail picture, I think is a soccer, like someone kicking a soccer ball.

Oh, soccer ball. Yeah. Yeah. I was pretty addicted. Well, I played a lot of sports growing up. When I wasn't— school was easy for me, so I kind of snapped through the school stuff pretty quickly. Homework would be like, I'd watch the Knicks and Rangers while I was doing my homework. I was like addicted to MSG Network at the time. Yankees, Knicks, Rangers. I could do my homework while I was watching games. But then, I like to play a lot of baseball, a fair amount of soccer, some tennis. So, mostly outdoor activities constantly. But, soccer, kept up with soccer all throughout every year, faded a little bit in baseball as I grew up and got frustrated with tennis and basically quit it cold turkey for about 15 years.

I mean, I'd almost be curious, you're probably fitter today than you were as a kid, right?

It depends. No, I mean, I'm probably more muscular. I doubt I'm fitter than high school playing soccer. Like, you know, the first day of practice we'd run like 3 miles for time and, you know, I think probably it was like a 6-minute minimum cutoff. So I don't think I could run 3 miles. I doubt I'd hit 3 miles in 6 minutes right now. But I didn't really lift weights when I was growing up in high school. So I was like leaner, much leaner.

Tell me about— I again read that apparently at the age of 6, you wanted to be a lawyer, like that was your dream.

Yeah, it was pretty, it was, it was pretty clear pretty early. I don't know if it's exactly 6, but plus or minus. My dad actually probably suggested this with a slightly more pejorative phrasing, but I remember getting punished for something. And I used to also like to watch professional wrestling, WWF at the time. And so I got banned from watching TV, you know, as a punishment. So I had a TV in my room. I wasn't allowed to watch. So then midnight came, midnight passed, and WWF was on late night. Back then it wasn't like a major institution. It was like on at midnight on like Channel 9 in New York, WOR. And so I turned on my TV at midnight sharp and he's like furious. He comes in my room furious, like, what are you doing? I'm like, well, you told me I was banned for the day. The day's over. So he suggested, uh, I, I become a lawyer at that point.

Tell me.

Good suggestion.

Tell me, when you were finishing high school, so you're 18, you've got some sense of the world, some sense of yourself. If I met you at that age, what would I assume you'd do with your life?

Uh, politics, definitely.

And did you consider that? Did you try?

In and out. Like, there's this hybrid lawyer-politician type that has been famous for years, decades in Washington, DC, and I kind of went down that path when I started practicing law. I worked mostly in Washington, DC. Which allowed me to go in and out of politics. And I definitely thought I'd be on that kind of trajectory. So I wanted to be involved in politics in different ways and then figured I'd practice law when people I wasn't close to were elected. And that was kind of the goal. I was always intrigued by politics. I read every book that one could possibly read about politics. I worked on campaigns, internships, like all the stuff you're supposed to do. And I learned a lot. I mean, I read everything and a lot of it's still here. Occasionally I'll meet a politician and some topic will come up and in the vast recesses of my brain, I'll remember the entire history of their congressional district and they will be shocked.

What would need to— I mean, it's interesting because your husband Jacob's in politics and what would need to be true today for you to go into politics?

Probably nothing because he could do all the political work. Not that much. I mean, the only thing that would probably motivate me at some point is If somebody I was very close to was elected President of the United States and they needed like a chief of staff or something, but that's about the only thing that would be tempting.

So tell me, after high school, so you went to Stanford, right? Is that where you started?

Yep.

And then I actually— so this hasn't come up in other interviews. Did you transfer from Stanford to Harvard? Is that a true story?

Um, no, not undergrad. So I graduated from Stanford and then started at Stanford Law and transferred to Harvard Law. So I went to Stanford. I wanted to, actually did want to go to Stanford since I was in like 6th grade. Also, I found out, I remember reading this copy of US News and World Report, 1983, and Stanford was on the COVID And I was like, oh, that looks kind of cool. I was sitting in New Jersey at the time. Like, that looks nice. And then it had the rankings, you know, the canonical, this is very early years of the college rankings, US News and World Report. And it was like Stanford number 1. And I was like, oh my God, it's in California. That feels so much better than being in New Jersey.

And it's ranked number 1.

So my parents can't barf. And by the way, they have really good football. I was like, college football is great. Like John Elway was playing there at the time as an undergrad. I was like, this is great. I can watch football. I can go to California. And I was imagining all the sun and beaches and things, and, and I could escape New Jersey. So I was on this crusade to go to Stanford from then on, 1983 on, or, or actually earlier, whenever that first issue came out, I was addicted. And, you know, everything was focused on how do I get accepted to Stanford?

I mean, the other story I read—

That was probably 9th grade. That was probably 9th grade.

That, that you had aspirations for Stanford?

That was when I was like dialed in. We're going to Stanford.

Are you still in touch with the people from like 6th grade and 9th grade? Because it sounds like you were super ambitious back then.

No. Um, very— there's a couple outlier people that occasionally cross paths with, but typically not from high school. Some from college, although, you know, when I went to Stanford, being an entrepreneur was basically the thing that only the weird kids did, people couldn't get traditional jobs. So there's a few people from my generation at Stanford that became entrepreneurs and some became VCs, and I keep in touch with that crowd, but not too many of my actual classmates. It was about 3 or 4 years later in the mid-'90s that becoming an entrepreneur and joining tech companies became like a mainstream thing on campus. And so from that generation on, I have friends all over the map, Stanford grads all over the map, once it became kind of a normal thing for Stanford grads to do.

Is it true that you had to sell baseball cards to go to Harvard?

Oh, to pay for— yeah, my parents, for a variety of reasons, had to sort of fund my Harvard Law education. So I had collected baseball cards and had some pretty valuable ones, so I was able to sell You know, sell them for the collection for a reasonable amount of money, which definitely helped defray the Harvard tuition.

Let's fast forward a bit. So you did go into law, which you said was your aspiration from essentially day dot. I believe Jeff was the first person that was able to convince you to leave law despite Peter Thiel telling you for years to do it. What did Jeff say that cut through that the others couldn't get through?

That's a good question. So there's a couple things about Jeff's pitch. So first of all, he was working at this company called voter.com. He left excited home for another startup. This was going to be his second startup. And voter.com was at the intersection of politics and technology. So my appreciation and understanding of politics fit in well, even though I knew nothing about tech. So that helped. Secondly, it was such a bubble in technology. It was the height of the internet bubble that companies like voter.com and people like Jeff just could not attract, could not hire enough people because there were so many companies, so many companies being funded that finding ambitious, talented, interesting, smart, whatever people was virtually impossible. So they were desperate to find lawyers like me. And then third though, I remember thinking from my perspective, wow, I'm going to jump into a whole new field I know nothing about. I need to learn a lot really fast because there's no way I can get proficient at this unless I actually learn. And so I was filtering potential opportunities by, do I think I could learn from this person? And I really felt that Jeff at the time had really mastered a lot of large parts about building sort of quote unquote internet companies, and that I could absorb them from him quickly, which actually proved to be the case. So that was a pretty good prediction. And then the last piece is I jumped in February of 2000. In January of 2000, I billed 360 hours at Sullivan Cromwell. I suspect it was not totally accidental that I was more receptive to a new career after billing 360 hours.

Have you ever reflected on what if you stayed in law and you still were a lawyer today?

Very, very, very rarely. To give you some color on how rarely, I probably went 20 years without thinking about it once. What re-triggered it was I was in Miami and I went to law school with Ted Cruz. And so Ted was in Miami and he reached out to me to have breakfast and I was like, sure. So I sat down with Ted, we had breakfast in Sunset Harbor, and I was describing how my field works, which We're basically the same age. So at my age, I'm like very old. And at the time he looked at me and he is like, you know, I'm the 3rd youngest senator. And that was when I was like, oh wow, the world would be very, very different. I wonder what would happen if I stayed in politics. I'd probably be like primetime now as opposed to feeling like I've gotta keep up with everybody like half my age. So that was the, that was one of the first times. And then there was a second time that actually was a little bit before that. The Harvard Law School Association was nice enough in, Maybe a 2016 error or so to invite me to speak. And I was trying to figure out, so I was flattered and happy to speak to a bunch of Harvard Law grads, but I really struggled with what I was going to talk about and kept procrastinating. I couldn't think of anything interesting because most of the topics and audiences I talk about would be completely uninteresting to most lawyers. Although these days I could probably talk about legal AI or something, but at the time I couldn't think of anything. So I was really frustrated and I tend to lose sleep when I get frustrated with, like, I can't, like, come up with a topic. And then the day before, I get this email, and because I was on the mailing list, it says title, hey, you know, something like, come see Keith Rabois, class of whatever, speak. And as soon as I saw the headline in the subject line, I'm like, oh my God, that's what I could talk about. Because they had put my class year in the title, class of '94. And I was, like, mortified because I'm like, now everybody's gonna know my age, and, like, they're gonna feel really old. But then I was like, Harvard Law was thinking it was honorific to put 94 in the subject line, that the older you are, the more wisdom you have and the more insights you have. And I was completely mortified. And so that was the whole topic of my speech. I was like, that's going to be the topic of my speech, how to contrast the way law works and the way tech works. That was the original anecdote.

They should share that recording because I don't think that's online.

I don't know if it was recorded. It may have been recorded. I've never seen a recording of it, but who knows?

Yeah, yeah. I want to go back a bit to September 1988 because I believe this is when you've received the 2nd edition of the Stanford Review, and the guy delivering the newspaper to your dorm room was Peter Thiel.

This random guy, it was a random guy named Peter Thiel.

Tell me, if Peter delivered that edition to the next room and not yours, who might Keith Rabois have become?

Well, he delivered it to all the rooms. That was what he was using.

Okay, well, what if he didn't deliver it? Let's assume you weren't there.

Well, yeah, so the more interesting thing was I happened to be in my room in Larkin, which is the dorm, and I happened to have the door open. So when he delivered it— people used to deliver lots of things, flyers, advertisements for parties, for pizza, publications, everything came in like under your door sort of thing. So I looked at it, I was like, oh, that would— that looks cool. And then I happened to chat with him. He's like, oh, we're having this like organizational meeting or on Monday or whatever at such and such place, you should come by. So I did. So yeah, there's a random question of like, if I had never seen it, never been interested, if I hadn't been in my dorm room at the time, if I hadn't chatted with him, would've I been proactive enough to show up to this meeting? Maybe, maybe not. Yeah, I was kind of one of these join an organization kind of kids, both in high school and in college. I probably set records at both schools for Leading simultaneously the most unique organizations in parallel. Yeah, I would get bored with school too easily. So what I would do is run organizations for fun, which turned out to be useful in other parts of my career. But I probably in high school probably led between 5 and 10 organizations probably simultaneously, and likewise, probably about the same in college. And so I might have joined or signed up or somehow showed up at some point, but who knows? But yeah, it was somewhat serendipitous. And I wrote an article for the next issue on the brilliance of Ronald Reagan's foreign policy, the underappreciated brilliance of Ronald Reagan's foreign policy, which Peter edited. And he really hacked the editing and I was frustrated with him. So I quit and we got our first fight.

I mean, that is such a— it's almost like, what does that show? Is that just right place, right time? People talk about luck. Is that just luck? You and him went to college together.

Yeah. I mean, you don't know because where else would I have gone? What would I have done with my life? I mean, that's why I don't bother thinking about it because you can't really control anything like that anymore and change anything. But it was serendipitous, but it didn't pay dividends in the way you would think for a very long time because Peter, like me, also went to law school. He went to Stanford Law and then he clerked. He wound up clerking on the 11th Circuit and he wound up actually working for the same law firm I did, Sullivan But he was prescient enough to quit S&C in 3 months and 4 days or 3 months and 5 days, where it took me 3 years to figure out I should do something else in my life. So this is how when Peter wants to make fun of me or he's introducing me at some event, he'll make fun of me for taking 3 years to figure out what was obvious in 3 months. I remember I interviewed Peter on stage once at our CEO Summit, and I was giving this introduction, or Peter was giving some version of his dialogue, and Al Gore was watching on the side because he was going to speak next. So Peter and I finished our interview, We leave the stage and Al Gore comes on stage and he says, I see this ego thing between Keith and Peter about like who quit law the first and like that somehow predicts how smart you are or talented you are. Well, I gotta tell you, I'm obviously the most talented because I quit law during law school. And the audience just erupted into laughter.

I'm actually curious to ask you on this point before we get to your career in more detail is if you could picture like a Hall of Fame learning room and you've got 5 seats, This is really interesting for you because you've got access to essentially anyone on the planet given your network. And you've got one seat and you can invite 4 people. And these have to be 4 people you know. So not, not randoms that you've never met. Who would be the 4 people that you've got to know you'd love to spend, say, 2 hours with and just ask questions?

It's a good question because I try to do that as much as I can. And the benefit, you're right, of having a good network is that you can try to absorb different ideas from different people. And most of the people that would be on that list, I know well enough. But I think one of the reasons why they put up with me is actually I sometimes can remix their ideas and/or pressure test some of their own and they find it valuable. I think that's the key. But one of the ones that was more interesting and arresting that I've shared one or two insights from was we were having dinner in Washington about a year and a half ago and It was a small table with Jensen, and he was talking about some of his management techniques. And because he runs Nvidia in a very different way, and some of this is well reported about how many direct reports he has and doesn't do this or doesn't do that, it was fascinating to try to probe and understand what he actually does, why it works, why it doesn't work, et cetera. So that was useful because I hadn't really had the chance to dive into his specific way of running the company at a granular level and how that translates to what you're trying to build. And so that was actually pretty fascinating. So that was an unusually serious conversation over dinner. But most of the other people that I'd be intrigued in sort of having a debate or dialogue and learning, I would probably set up in some other capacity.

Do you want to name any names?

I think I still, you know, I'll say this publicly. I think I've learned more about how to build a technology company from Peter than anybody else. He also has a different set of perspectives, some which have been more widely diffused, you know, through the domain, through the ether, partially because some of his disciples have been successful, partially because he wrote a book about it, speaks about it. I think he'd be probably number 2. The 3rd one will surprise you, not because he's already not well known, but I'm not an investor, but I find chatting with Winston of Harvey to be the most useful at the moment. Partially, I think our brains, both being ex-lawyers, are kind of wired similarly. And partially, he also is a voracious reader and is pretty broad. But we can build on each other's ideas. Our natural instincts are somewhat contrarian to a lot of people's and about a lot of company-building stuff. And so I find it incredibly useful to just chat with him about almost any topic.

You've got one last seat. Who'd be the lucky fourth?

Well, Sam's always a good choice. I mean, I've been friends with Sam for so long. It's hard to even disambiguate ideas and insights from Sam versus strains I had on my own. But I'd say the most interesting part, although everybody wants to talk about the future of AI and stuff like that, he still has this ability to assess undiscovered talent that's extremely world-class. And chatting, discussing with him, specific people and why is incredibly valuable in sharpening and honing my own instincts, especially if I've seen or met or encountered these people. And business strategy, there are very few people that have the overall business acumen. And this is true from the time probably I first met him in 2005 when he was 19. It was true then. It was obvious then.

Let's go into your career. And I want to go So I've tried to do this a bit differently. And I said to you the other day, I will ask you different questions. I want to live up to that, that hope. You left PayPal, I think in November 2002, around about then, right? And you joined LinkedIn, you joined LinkedIn in January 2005. So that's a 2, 2.2 year, just a bit over a 2-year window. What did you do in those 2 years?

Great question. So I spent the first year working with Peter at what used to be called Clarion Capital, which is mostly a hedge fund. With a bit of tech investing, angel seed, beginning some of the insights of Founders Fund there, starting companies, investing companies, negotiating, investing in companies. And then I joined in 2004 this very complicated startup that would use video games, effectively video games, to retrain people's brain who were suffering from dyslexia. It's a very cool technology. It mostly worked. It was kind of a little bit of flaw of averages. It worked extraordinarily well on a segment of people afflicted with dyslexia. But at its time, it was the kind of technology that could only be delivered in a retail sort of store. Mobile devices weren't capable enough to delivering the programming. So it was kind of like you had to go to a Kaplan Center, Princeton Review kind of place, and very challenging business model. Eventually that company was having challenges. And so for a variety of reasons, the company was going to fail one way or the other. I left to join LinkedIn, which I'd been tracking, Since day one, actually before day one, Reid Hoffman had the idea for LinkedIn back while we're still at PayPal, while we were counting down the days for the acquisition to close. He had 3 ideas and one of them was LinkedIn, which is the one I was interested in. The other 2 were very bad. One was terrible, one was just mediocre. And so I was very interested in LinkedIn from before it was even started. I wound up angel investing in LinkedIn. So that's the answer to the other, to the 5th one. Forgot about, um, the LinkedIn forgetting about is pretty funny. But then there was nothing really for me to do in the beginning of LinkedIn because it was really like, could we create a product that would be viral and grow organically? And that was mostly a product and engineering challenge, and Reid's brain as a business person was more than sufficient. So it would've been duplicative for me to be there at the very, very beginning. So it was kind of waiting for when they needed things like revenue And like other complicated business topics to join. So when the company started growing at a viral— above a viral coefficient of 1.0, they started needing people to produce revenue and business lines. And that's what I was hired to do.

I actually heard in— I came across this in my research, and you can tell me if this is true or not. Apparently Reid said to you that your arguments are very quantitative, and you started putting metrics into everything for the next 6 months. Oh no.

Yeah. No, I think I've told this story or posted a version of this story on Quora somewhere. But no, Peter gave me the critique at PayPal. I wanted to get promoted to— we had this EVP, executive vice president level, and Peter gave me some feedback delivered through Reid that my arguments weren't quantitative enough. And Peter is an empirical genius. He wants everything in numbers and calculates numbers very fast. And that was basically the PayPal culture. So I got the feedback from Reid, and so then I started framing everything with all kinds of quantitative insights, and it worked. I got promoted relatively quickly thereafter, but it actually did lock in people's brain that I was actually capable of this. And maybe it was a stereotype of having been an ex-lawyer and people thinking that I would just— perceiving me from the framework of an ex-lawyer, but I put some effort into it and I actually have always been fairly financially savvy and incredibly proficient at statistics. Peter at the time was actually more into calculus. He's like, calculus really matters. First derivative, second derivative stuff. Statistics is pretty bland. But he conceded that I was sharper at statistics than he was. But he thought it's a meaningless— very Peterian was being like, yeah, you're better at statistics than I am, but statistics is intellectually bankrupt compared to calculus. Anyway, I got better at both, but I started weaving both into my work product, and apparently it had the desired effect.

And also, was LinkedIn the first time you were a people manager?

No, no, no, no. I had a fairly sizable team at PayPal, actually, because I ultimately was responsible for our government affairs operation, or most of it, our Our sort of strategic business partner relationships was pretty complicated. Our financial services team, which is really the partnerships that make the money move where it's supposed to move all around the globe, which is a fairly complicated set of puzzle pieces and negotiations and contracts and different partners in different regions, is responsible for our comms team and our kind of marketing comms team. And so that added up to be double digits easily, but it's a very elite, more Navy SEAL kind of team management. We didn't try to scale any of those teams. David Sacks had this mental model of, I'm going to divide, which I use in my How to Operate lecture, where I learned from David is to avoid people artificially scaling in their teams because it makes them feel important. You just divide their output by the number of people on their team and it forces you to really think about the value of that incremental hire. So that was fairly challenging because all these roles were very different. like juggling 4 or 5 things simultaneously. They're pretty different fields, actually.

Tell me if you— let's assume you invested. Let's assume I'm a founder and I've got a new company and you've invested, and I come to you and I say, Keith, I'm gonna become a first-time people manager and I would love your advice. What are the 3 things you would advise me?

I think there's one very straightforward one, which I used to be incredibly adept at, which is hire amazing people. I was like, if you hire the right people, the job is really easy. If you hire the wrong people, all the people management skills in the world are not going to save you. It's a little bit like sports. If your team is awesome in terms of ability, coaching can be very fun and very invigorating and very rewarding. And if your team is not very talented, there are opportunities to outcoach the rest of the world, but they're very rare. And I would rather have the talent. So I was basically learn to not be a better people manager, learn to hire better. And if you recruit better and hire better, you're ultimately going to be great. And if you do that better than other people, you'll have a team with incredible density of talent that has incredible ambition and pushes you to even be better at your own job, which is even more fun, which I did have at LinkedIn. I had a very elite team, especially the first 2 hires, Steve and David, were incredibly talented, incredibly ambitious, very productive, and really did push me to achieve more myself. So it worked magically. I refused to join LinkedIn unless the company gave simultaneous offers to Steve Segman and David Hahn, because I knew that then I'd have a core team that could really deliver, and I didn't want to have to rebuild a team from scratch.

Just to extend that advice question, What is important in that recruitment phase? Is it the interview process? Is it the reference checks? Something else?

Well, they're all, I mean, they're all like, look, at the end of the day, they're all ingredients and inputs. But if you wanna hire, it depends what your goals are, but if you wanna hire top 1% talent, sourcing is pretty critical. And knowing what you're looking for, knowing what traits are gonna predict success. Any given role requires a certain set of skills to be successful at solving the challenges that are most critical. And being able to identify what are the key ingredients to success in this role, and then testing whether through an interview, references, et cetera, whether this person has those traits. And ideally those are their superpowers. So when I'm counseling these days, what I do is mostly play consigliere to founders. And when I'm consigliere and people are hiring, I'm basically saying, okay, what problems are we trying to solve here? Like, what are the challenges? Why are you hiring? Okay, they're like this challenge. Okay, great. What's the single most important skill in being successful at solving that challenge? And then go find that. Don't try to have a list of 10 different traits. This is something actually I originally learned sort of through Reid Hoffman of don't create a list of multivariables and like there's pros and cons. It's just like, what's the number one criteria for success? And then make sure this person is outstanding at that. It's actually how So we prescribe kind of writing a seed deck. It's like there's 3 core risks to any business. Great, I've got this person lined up to solve this one, this person for this one, this one, and they each have an unfair advantage in solving and conquering these challenges that nobody else in the world has solved before because of X, Y, and Z. A great illustration of that is the Varda seed deck. Follows that advice right down the middle. It's a perfect illustration, very intentionally. drafted that way. I think there's copies of the Vardisy deck available online.

Tell me about—

I read the other day on Twitter, you said, I insisted on avoiding an EA for the first decade in tech, and it was mostly wrong.

Yes. So I hated the idea of having an EA. I like to schedule things myself because it can reflect my priorities. I also didn't like the optics of turning something over to some EA. And so all through my days at PayPal and LinkedIn and beginnings of Square, you know, all slide, I never had one, never wanted one. Was somewhat skeptical of people who over, you know, over-demanded one. And then Jack came up to me and said, you have to get an EA. I was like, okay, why? And I explained all the reasons I didn't want one. And he said, it doesn't matter. He's like, basically you're causing too much damage for other people because people want to add meetings or delete meetings or move meetings and they feel like need to go to you, which is true because I was doing my own calendar. But he's like, the pain, the perceived friction of interrupting you to move a meeting deters people from moving the damn meeting, and that's not constructive for anybody. So he's like, it's more important for other people to be able to function without having to interrupt you in the middle of the day all the time. It was good advice actually, but you do lose some things. So for example, now weaving back to the Jensen conversation, one of the things Jensen does, he talked about with me, is every Sunday night he looks at his calendar and he cancels half of his meetings because they don't reflect the most important priorities at the time, which is a great approach. But that's something you have to do. Your EA can't do that. I still schedule a fair number of things myself. I still like to have— because I have this, even if you have an incredible EA, and I've been— I've actually had very, very talented EAs at Square and And at KV and along, and some of the time at Founders Fund, I've had really good EAs, but they still don't have your business strategy locked in their brain. And so the good, the best EAs definitely remember everybody in my life and they kind of know who's who and why and how important they are and what the prioritization is. They definitely can do that stuff very well. They are actually really are excellent at that. All, basically all of them. But what they don't know is What's in the back of my mind about strategically, how are we competing like this week or next week? And what am I thinking about changing about our strategy, whether it's a company or KV or something? And therefore, when I shuffle things around, I have a sort of a different goal in mind than most EAs would be able to track. I do use a chief of staff now since I've been at KV. I never had one this in my It's become popular among tech companies though. My chief of staff usually has a much better strategic feel for what's top of mind because he shadows me basically 24/7. So I typically take my chief of staff to all meetings, all board meetings, all one-on-ones, all interviews, all pitches. And so they have a pretty strong perspective of like what's important and why. And so they can help bridge the gap between what an EA can do and what I actually would do by hand, but I'll still move things around. There's even things I'll just add to my calendar just on my own. I'll just be like, don't even put it on my calendar. I just know at 6:00 PM tonight I'm just going to do this. But for tracking purposes, now I even add those things more so we can do an analytical deep dive at the end of every quarter of how did Keith invest his time? How much was new pitches? How much was early stage versus growth stage pitches? How much was at board meetings? How much was one-on-ones? How much was like PR or whatever? How much was podcasts? So now I go back and add stuff onto the calendar, but mostly for analysis.

You know, one of the things I've reflected on, like I've been doing this pod for nearly 7 years, is most high-performing people take handwritten notes. It has been my observation. And I think some of the people I spoke to who've worked with you said, yeah, you've got the handwritten How does that work? Because you do, you meet so many people, you do so many meetings. Like, if I handwrite all the time, I will write gibberish. It will just be stuff I don't understand. How do you do it? What's the secret?

I carry a notebook all the time. And yeah, I insist upon handwritten notes. I do not allow really laptops in meetings on that. I mean, obviously you can present, but like, I don't allow people to type or take notes. First of all, you don't retain them. Secondly, it's incredibly distracting. So yeah, I have a notebook with me. Wherever I go, when I travel, I bring a notebook with me. When I go to a board meeting, I have this pen. I use exactly this pen, only this pen. I've actually got a lot of my friends addicted to this pen.

What pen is it? Tell us. Tell us the pen.

It is a beautiful— as Trump would say, it's beautiful. It's a precise, unique— the key is it's a precise V5, not V7 Pilot.

Right.

I use blue, but the black is pretty good.

This is not sponsored.

It's not sponsored. They should be paying me. I've been on this crusade for like 20 years. It's the only pen I can use.

I want to get to VC in a second and also talk about one crucible moment from your career. But how does that shape your view on AI recorders today? Are you anti-AI recorders or you're pro them?

I'm neutral. I don't use them. I still handwrite my stuff, but I don't mind if other people are using them. I think they still should be writing notes, but it doesn't affect me one way or the other. There's some training we're working on though where we're trying to create an AI proxy for me, and the recorded notes are probably a helpful ingredient in making that project a success.

Interesting. I'm curious to see that when you, when you have it out. That'll be fascinating. Tell me about Slide. I feel this is a chapter that people skip over between LinkedIn and Square, and, and some people said to me—

We tried to edit that. I would try to edit that out. No, just kidding. We definitely learned a lot. I learned a lot of things there.

Well, a lot of people said to me, because everyone I spoke to for research, I said, what are some things I should ask Keith that he's not talked about? And this was one that came up. People said, ask him what has he learned from those 3 years.

Oh yeah, a lot. I mean, incredible number of things. First of all, we had an incredible team. I went to work for Max Levchin again, and we had a rocket ride, roller coaster ride in 3 years. We were doing extremely well in some of those years and extremely poorly in other ways. We learned basically how to build on other people's platforms, which we succeeded at with PayPal on eBay. We had mastered on MySpace back when that was the primary social platform on the planet. And then we initially succeeded on Facebook's platform before Mark and his infinite wisdom made a lot of changes, and we were less adept at competing after the transformation of the Facebook platform, which did cause significant issues for the company. So I learned incredible amount About building on other people's platforms, the pros and cons. I learned a lot about actually ran a product team for the first time—a true product team, consumer-focused product team versus like at LinkedIn I built like revenue products. That was interesting and great learning and a lot of a lot actually a lot of fun. Learned a fair amount about organizational stuff partially because a lot of it was a work in progress where at PayPal it felt like the organizational shuffles were like. bolts from God. Like somehow Peter or Max in their infinite wisdom would just shuffle the entire organization and like this person would disappear.

Yeah.

Whereas at Slide, I was involved in like all the important decisions. And so that was interesting. It was a learning curve where I was responsible for a broader set of things. And so it was a good challenge even though it didn't work out that well. We pioneered a lot of things that people take for granted, including the pre-public institutional, large institutional investment rounds to T. Rowe. We were the second investment T. Rowe ever made into a private company in technology. So we started a lot of these trends, but ultimately, and I learned some lessons about what not to do. We sort of edited what we were, our vision, and to be more in line with the modern version of the Facebook platform. But that had a lot negative consequences that were less appreciated to help counseling founders today about pivoting. There's some cautionary tales in there. I learned a lot about office design because I think one of the things that went wrong in our Slack culture was we had a very dense office. We were very functional and way above fire code. And then we moved to a nice office, but it was multiple floors and it caused all kinds of catastrophic messes organizationally. And so much more attuned to things like that that are Some things you kind of have to learn the hard way.

Interesting. So you clearly reflect it on it. So thank you for that.

Oh yeah, all the time. But the most important thing is to learn to build something successful after, which Max has obviously done.

Yeah. I want to come to VC and I want to talk about it from a few angles. One kind of state of play today, but then let's start with Vinod. I've heard in a few interviews you've said Vinod is the investor you most want to emulate.

Correct me if that's I don't think that's right. No, no, no, no, no. I, I think Vinod is an incredibly successful investor, period. Okay, like no doubt about it. But his style overlaps some with mine and what I aspire to do and is somewhat different. So Vinod is a technology-driven investor who sees the implications of technology better than maybe anybody else. So for AI, he's on the AI— he's going to transform everything at least as early as 2013, published papers on AI medicine, blah blah blah. A decade probably before many people saw anything, 5 or 6 years before really anybody. And he's done that consistently in his career. He's extremely clever about creative strategies to solve the David and Goliath problem of how do you compete with a large incumbent? He kind of pioneered open-source software back in Sun days, actually, as a business strategy. There's a Harvard Business School case study you can read about it. And he taught me, most importantly, the number one lesson, when he's on the board of Square was he said, the team you build is the company you build. And coming from him, it resonated particularly well because he's a technology investor. That said, he understands it's all about the people at the end of the day. And you can get distracted with technology and innovation and who's doing this and what the architecture is and all that and what the market is and customer acquisition strategies and payback. But it comes down to, can you build the right team with the critical density of talent, which is something I've always believed, but he really clarified it. And coming from the polar opposite of being a technologist, it just double-edged in my brain. And so I've been on that crusade ever since. I use that formulation all the time, every week. So learned a lot from that experience. He's more of a hypothesis-driven investor and I'm more of a founder-driven investor.

Fair.

You tweeted in February, in quotes, the AI era will not be friendly to startups who chased revenue traction at the expense of accumulating advantages or 7 powers. Can you unpack that tweet?

Sure. There's such a massive wave of AI adoption and interest that right now launching a company and getting to $10 million of revenue or $100 million of revenue, things that would typically take significant effort and time, happens fairly quickly. And sometimes easily. That does not mean that those companies are destined to end well. Sometimes, like when anything's easy, it means it's easy for other people. And when things are really challenging and difficult, it means it's actually really challenging and difficult and therefore maybe sustainable and durable. So I do think that a lot of people have focused on the growth at the expense of what are our accumulating advantages. The way Vinod would describe this is actually pretty useful. in this case, of reverse engineering from 2030. Like, is this company going to be sustainable to 2030? What advantages will they have in 2030? How does that translate versus is it a point in time and is the momentum there because there is such a massive wave? Now, that said, there's a couple caveats here. One, if you're riding a massive wave, you have the opportunity to discover new ways to bridge into that may have more durability or more sustainability or QWING manages. Momentum is indispensable to any startup success. And if you have a lot of momentum, you may be able to hire a lot of people that are great. And if you have a dense pool of people that are great and awesome, you may discover opportunities and jump into those before the— your current thing is fleeting. That can work in the hands of a great founder. That is not a bad investment at all. Second thing is, if you time— AI is, you know, quite hot. Lots of incumbents feel the need to acquire things. If you time an exit, you get an offer from some large entity and you're sharp enough to accept it, timing that can work out well for everybody on the cap table, employees, investors, et cetera. But there's a very big dis— a very big difference between building a durable iconic company that's a public company for decades and a savvy acquisition, even though the returns to an investor can look similar. We're in the business of company building at KV. We, you know, obviously there are companies that we have had acquired, but we really want to be in business with founders who want to build a business that everybody has permanent history with that's on someone's iPhone. You know, when I look around, one of the invigorating things is I look at my friends' phones and I look at, you know, the apps that are on the home screen and I try to count how many I've been involved in. That's, that's cool.

Yes.

Building companies that people don't remember Definitely could be lucrative, but it's a different art in and of itself. So I think there's right now a lot of momentum, and there's a lot of momentum that translates into revenue, and there are companies that need pieces of the puzzle and they're willing to spend real money, and the current political administration's fairly friendly to acquisitions. So there is a window of opportunity for being quote unquote successful as an investor and employee founder that isn't building a permanent company. I'd rather build a permanent company partner at the margin, certainly, at least with people who want to do that, kind of come hell or high water.

This is a really topical area at the moment, right? Like, I've never seen this level of enterprise adoption of technology. Like, we talked about legal AI. Like, I know both Harvey and Legora really well. You look at Decagon, Bridge, pick your name, and they're all like $200, $300, $400, $500 million ARR in like 2 years, 3 years. I'm curious, how do you— how are you currently distinguishing product-market fit from corporate curiosity?

It's a very good question, and I don't think there's a superficial answer. I think you need to do reference calls with the enterprises that are buying. You can look at engagement, and there are proxies like what fraction of the company or what fraction of a department are using a product on a daily, weekly, monthly basis, like we'd always evaluate consumer companies. You can definitely do that too. You can look at the actual terms of the contract, Are they pilots? Are they complete contracts where they have a contractual commitment that doesn't have an easy cancellation period? There's a lot of stuff you can do, but at the end of the day, unless you're producing ROI, like business outcomes that the enterprises care about, it's still temporary. No one's going to pay tens of millions of dollars forever to a company that doesn't drive a meaningful lever in someone else's business equation. So as you connect what you do, as a startup to the P&L of a large company or the competitive landscape of a large company. You make their revenue accelerate, blah, blah, blah. You make their costs decrease. You give them a structural advantage vis-à-vis their competitors. That's durable. Anything that's not that may be more of an experiment or cover your ass. We need to get an AI strategy. So we'll see how that plays out. It's again, working backwards from 2030. Are you building layers of revenue, like true layer cakes? These are fundamentally sound customers that love what we do because we drive outcomes that make their business better in their competitive markets. That's foundationally great. And if you keep doing that over a 5 to 10 year window, you're gonna have a wonderful company that's incredibly valuable.

I wonder, and I think you've thought about this before coming back to Coastline, starting potentially your own fund. I'm curious hypothetically if you had, say, call it Rabois Ventures today, What is the optimal fund construction in this AI world where rounds are getting bigger, valuations are getting larger, and it's just hot?

That is a great question because you're right that median round size for a seed— I like to be the first institutional investor as often as I can. And I know you talked to several founders where that was the case. Even those rounds though, when I used to be able to invest $500K to $5 million, let's Sometimes now are $5 million to $50 million. And so you need a fund that can compete in the dimension you want to compete the most important. So most important for me is to be first. I do do other investing. I have led growth rounds very successfully, invested in Stripe in a growth round. I led a growth round for Ramp, led a growth round for Fair. I've led a growth round, somewhat of a growth round for Factory recently, co-led with Vinod a growth round in Aven. And so definitely do this, but at the end of the day, where I have the most alpha and most competitive advantage is being the first institutional investor in a high-potential company. Those rounds, the risk-reward of those rounds is changing if you have to commit $10 million instead of $3 million. And so I don't know what the right fund size is. And then you have these, what Ben Horowitz labeled back in the day, fat startups, where before they've done anything except marshaled a team, which is important for our point about the team you build being the company you they raise $50 to $500 million, and what's the risk-return look like at those? And if your fund size can't easily write a $25 million minimum check for a seed that doesn't have anything, you can't participate in that whole segment of the new startups. And I think missing a whole segment of startups might be a mistake too. So it's one of the challenges for a new emerging manager of any type, whether my background or less experience, is that The size of fund you would need to really participate has changed from something that maybe you could be influential at $100 to $150 million, $200 million. $500 probably is the minimum fund size right now.

I think a lot about the line, which I'm sure you've heard of many times, is startups die more of indigestion than starvation.

I think that's often repeated. You know, it's a Bill Gurley aphorism, as far as I can tell. I think that like many aphorisms, there's a lot of truth. There's a kernel of wisdom there, but I think the exceptions matter. Peter Thiel is a pretty specific proselytizer of focus, and I generally think he's more right than wrong. So I'm sort of on that side of the fence. I preach focus, and Peter had ways of implementing focus that were pretty extreme, which I've talked about in other podcasts and SubQuar posts. I generally subscribe to the focus point. But there are exceptions when you have to do multiple things in parallel. And there's an argument in the AI age that because of the ease of building certain things, you may need to do more in parallel than ever before. It's still debatable, but I understand that sort of Patrick Collison's of that view and he's usually right. One thing I've learned is more right than wrong. So I do want to debate that and how that with him and how that compares to the Peter focus point. But I generally start on the side of focus.

Let's move to rapid-fire sprint to wrap this up. Is there one non-work investment, ideally of time and energy? Is there a course, holiday, or hobby you consider the best?

The best investment? Well, you know, I'm very addicted to health and fitness. So I've become sort of on a crusade about sleep. And I'm on a crusade about VO2 max. If you just simplify it, like, you'd optimize both. The higher your VO2 max, the better your sleep, the more— the longer you're going to live, and the better your life's going to be.

One interview question you love asking prospective candidates. This could be in a diligence process for a founder or a hiring process for a candidate.

Yeah, the one for executives I usually use and I really like is, if you were the CEO company acts where you currently work? What would you have done differently? I find that to be incredibly provocative and insightful.

One thing you want to learn in the next 6 months outside of work?

Oh, outside of work. Probably to play the piano well.

Nice. That's, that's different.

There you go. I told you we'd have some interesting new content.

Is there one pet peeve?

Oh my God, Oh yeah, I have a lot of pet peeves.

All right, give me, give me some.

Yeah, so look, one of the things I learned from Peter, or Peter clarified, I was probably always this way, but he distilled it really simply for me, is people systematically undervalue their time. And so I am a time maximizer. I'm always trying to find high-leverage ways to maximize my time. So people who do not value their time drives me absolutely crazy. The second thing is I have incredible memory for conversations. I can usually recycle almost every conversation I've had with someone in my life. What that means, that's a feature. The bug part of that is anybody who repeats themselves and tells me the same story or anecdote drives me absolutely insane. If they ask me a question the second time, I get furious because I'm just like, you asked me that last week. And it drives me crazy professionally, socially.

Totally. Last 2, one thing you've learned from Jacob, That's a really good question.

Well, the key ingredient in his success is he's been able to blend 2 fields. So when he first started down this path, he was the only person who could really explain to technologists the world of politics and the only person who was very proficient at the elected official level of explaining complicated tech concepts. And so he became the one person bridging the gap. And I think the lesson from that is one way to create a superpower is to be able to fuse together 2 worlds that do not speak the same language.

Nice. That is, yeah, that is exceptionally hard. Last one, Keith. If you could recommend one question I should ask the next guest, of course, you don't know the next guest, but anything I should include?

Well, yeah, you need to tell me who the next guest is. And then I'll give you a good question. I think I know some of your upcoming guests. They all seem interesting.

Yeah. Yeah. We've got some cool ones. We got some of your founders actually. We'll have to—

Good. Well, those are the— yeah, we'll have to get you all the great founders.

Yeah. I mean, I actually say to VCs, you can use me as a diligence because I ask them about their childhood and they're like the human side.

Well, the funny thing is you should probably know, um, I never ask people this question. It shocks people all the time. A lot of very good investors who are founder-driven, like Daniel Gross, for example, or Doug Leone really dive into people's childhood, and that's an important part of their assessment. I'm a very founder-driven investor, and I almost never ask questions about their childhood.

Interesting. And people also don't ask you about your childhood, which I find interesting.

They do, but it's so less relevant. But maybe that's where I learned this from, is because I don't find it that relevant. To ask me, I don't, I almost never ask people about their childhood or the family life. There's times when, you know, they volunteer it and it could be interesting or not. But my go-to set of questions when I'm meeting a founder usually does not entail anything except like, let's dive into what you're doing and why. And the why may entail like some historical experiences.

Well, it's actually a good point that I tend to think about is people change over time.

Right. That's true too. And, you know, if you had picked me up as a, like, look, I was one of the best lawyers, you know, you could find. I won this award, which is embarrassing now, but one of the, there's this way to be selected as one of the top 4 lawyers in the United States under 30. You get selected by the Supreme Court, the ju— the, uh, Chief Justice of the Supreme Court and the Chief Judge of the UK or whatever he's called. I can't even remember. So it's a pretty prestigious thing. But if you had guessed that I would be this tech person from that, so anybody who's diving into this very precocious 30-year-old lawyer would've totally missed probably my potential as an entrepreneur. So maybe that's part of the reason why I don't go that direction is I don't know what sparks they would've been able to identify. And I think most of the things they would've tapped into would've not predicted entrepreneurial Well, I hope you enjoyed this, Keith.

Hopefully I asked you some decent questions. Cool. Great to be with you. Thank you so much, and I will see you in a couple of weeks. We've got something exciting coming up.

That's a wrap. So if something in this episode sparked a thought, send it to a friend or colleague. And if you're curious about partnering with us at the Curiosity Center, whether it's this podcast, to our reports, events, and more, and join the ranks of existing commercial partners including Google, KPMG, Vanta, the University of Melbourne, and others. My details are in the show notes. Until next time, I'm Vidy Tagorel, and this is the High Flyers Podcast.