Keith Rabois: Lessons from PayPal Mafia, $OPEN, & Investing

You have to find what your comparative advantage is in life and then double and triple down on it. Each of the people that worked at PayPal that was talented had different skills and traits. The reason why they went different directions is they figure out how to frame themselves so they're not just the best, they're the only Peter. Not many substitutes for Peter. Max. Not many substitutes for Max. David Sachs, I think has found his own roll off.

You are a part of PayPal mafia. I have to ask, do you guys have a group chat? No.

One of the two best parts of being a VC is you get to work with the most talented entrepreneurs in the world and you get to watch them. I have actually given a whole speech on lessons I've learned from Vinod, Peter Thiel, Reid Hoffman, Max Luvchin. But I try to absorb from everybody.

What traits do you look for in talented young individuals?

What you want to find is someone has a non zero chance of changing an industry of the world. That's it.

You are also very active on X. But I have noticed since joining coastla again your contrarian takes have. I mean I'm not going to say they dulled down but like you have gotten a little bit more mellow.

Oh my God, I'm getting old. Damn it. My thesis is I ran out of contrarian takes because they've all been proven to be true.

Have you thought about writing a book?

I've started to play around with ChatGPT to write a book for me. The outline it came up with is actually pretty damn good. The title was very non intuitive and kind of edgy, which I like. It's called.

One of the common themes that I've noticed around you and your circles. And in doge, the new admin is embracing young talent. So in DOGE hired really young. Teal Fellowship hired really young. There's different mafias around this too. But for you, I asked Delian, like what should I ask Keith and, and Delian? He said he's. He told me to ask you, what do you see in certain young folks that convinces you to spend so much time mentoring?

It's the same thing as investing. Truthfully, it's the same formula. What you want to find is someone has a non zero chance of changing an industry of the world. That's it. It's really that simple. And it's the same. You're scouting for professional sports, you're scouting for music labels. It's the same basic concept is most people are in the middle of the bell curve and either don't have the skill or ambition to be two standard deviations away. Investing is all about finding those people and giving them either capital or advice or both. The same thing, whether you individually mentor someone is the exact same formulation as someone who has super high potential and has a shot of transforming the world. So try to find them. It gets harder. The assessment part actually I think gets easier. The identification part is harder. It's not like you get to meet all 4 billion people on the planet. I've yet to find a way to do that. My friends Daniel Gross and actually back in the day tried Pioneer, which is a way of scaling the identification of these people. And it had had some success I think, but I found that you need to do it in person, which really reduces the scalability of it and the disadvantages. As you age, your natural social, professional, personal networks are more distant from up and coming people. So you have to find alternatives to that. For a while now I'm even too probably dated to use this for a while. I use my soccer team as a way, as a way to find up and coming talent. It worked pretty well. Hired two, at least two people off my soccer team that worked at Square. They started a company that's a very good company called Fair so but was a good magnet for people. You can, you can try to find new alternatives but it gets difficult. You can rely upon friends of friends and there's some truth to that. You know, the adage that you're the average of the five people you spend the most time with is basically true. So if you find one node, one person who's a node, the five people that that person spends the most time with, there's probably some pretty other talented people in that group. So you can try that. But the technique of identification, you can read social media people who are exceptional sometimes publish stuff. My other co founder at Opendoor, Ian Wong, I'd actually read his Quora posts and didn't no idea who he was. Just read some of his Quora posts back in the day and I bumped into him at a professional event in San Francisco and he introduced himself and asked for career advice. And I said your only career advice is I have a job for you starting on Monday at Square. And he was like absolutely blown away. Like I was like, nope, you don't have a choice. Like I've got a job for you. And he's like, don't I have to interview? I'm like nope. And the reason why is I'd already read all his content and I could see from his content and like his education that he had a confluence of interesting ideas and backgrounds. And I was like, if I can't figure out how to make you useful, like it's square in my problem, not the other way around. He had, he had electrical engineering and a CS background and a data science background. Like we do all of those things. There must be something for you to do here. We only have like 30 people. Like I've got. It's unusual that someone like with that background walks into my lab. Please start Monday. And he did. And you know, he wound up then later co founding Opendoor with me, stayed nine years as CTO and now he's running a really cool company in Seattle.

You're gonna bring him back?

Sorry?

You gonna bring him back?

No. His company is doing very well. Like it's not announced yet, so I won't talk too much about it, but it's got very high potential from what I can tell.

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So what traits do you look for in talented young individuals?

I think it's really easy to describe conceptually which is there's only. There's two formulations. One is you are in the top. Call it 1 to 10 basis points on some specific trait. And that can, they can be very different. You can be the smartest person I've ever met. You can be the most tenacious person, persistent, best salesperson, best at assessing people like you have some trait that's just like holy cow, I've never seen anybody like that before. Your ears just like perk. The only other formulation I've seen is you have this combination of traits that's rare the confluence of traits. So we talked about C, for example, I mentioned he's bold and ambitious and at the same time incredibly rigorous and analytical. Those traits do not usually go together very well, but they happen to be magic. It's not surprising. He was very effective in the financial services, building out shop pay, etc. Because those traits are like indispensable for building a payments innovative company. They're also truly indispensable for building Opendoor successfully. So you're looking for this rare combination I talked about. Max Levchin is a first rate technologist and a first rate business strategist. There's less than 5 of those people in the world. So if you see these rare traits as a Venn diagram, that can be your like sort of top 1% answer. So that's what you're looking for.

An early talent circle that you were a part of was a PayPal mafia.

Yep.

We now have multiple mafias. We have the Teal mafia, the Teal fellows mafia, there's now the Palantir mafia. Somehow they all come back to the same people. I have to ask, do you guys have a group chat? Do you have a group chat?

No.

Do you keep in touch?

Well, I keep in touch with the people I like and you know, the like I'm going to Max's birthday Saturday and I'll see, I'm sure a select group, but I would say there's a constellation of maybe from the PayPal days, 10 to 30 people where we're pretty interactive. You know, obviously I worked a lot professionally subsequently with Max and Peter and David Sachs. And so I think there's concentric circles of people who continue to work together, continue to start friends, but not like there was like 254 employees when we sold the company in Mountain View. And I don't keep in touch with Most of the 254.

What do you think you've learned from watching everyone go on their own path? Like what are the key lessons that you've taken away from? This person went that way, this person went that way. Like I think more macro of like human behavior.

Well, macro human behavior is I think you have to find and it's advice I give people constantly, probably every week what people want professional advice and even people don't want it, and I sort of force them to listen is you have to find what your comparative advantage is in life and then double and triple down on it. So each of the people that worked at PayPal that was talented had different skills and traits. And I think the reason why they went different directions is they figured out how they wanted to compete with the rest of the world. So I was mentioning. I grew up reading this autobiography by Pat Riley. And in the autobiography I read when I was probably a sophomore in high school, I saw this quote that he was quoting Jerry Garcia, the Grateful Dead, and said, you don't want to be the best in the world at what you do. You want to be the only one who does what you do. And so I think that's mostly people who are successful, they figure out how to frame themselves so they're not just the best, they're the only. So Peter. Not many substitutes for Peter. Max. Not many substitutes for Max. David Sachs, I think, has found his own roll off. You find your own course and you double and triple and quadruple down on it, and that's how you want to be successful.

Can I ask for you a little bit more personally? You have developed some really strong frameworks of understanding and breaking down different situations, very complex situations. How did you, how did you. How do you, like, have this, like, really, I guess, like clear and insightful way of viewing the world that you can distill complex subjects. Subjects down so easily?

I think my primary role as a venture capitalist is to be a consigliere to the founder. And even as an executive, I think this, this skill is critical, which is simplifying a complicated set of facts to an actionable framework. That's the best way to give advice and take a step back. Communication, I think, is misunderstood. Communication is only effective. You're only successful communicating if the recipient understands what you're saying. So it's like throwing a basketball pass. It's the person who throws the pass responsibility to make sure the recipient catches the pass. You don't blame the recipient for fumbling the ball. It means you didn't throw it, you didn't pass the ball correctly. So you want to take into account the qualities and characteristics and attributes of in basketball, seven foot center. You don't want to give them a pass. That's like six inches off the ground. That's your responsibility. So the same thing's true. If you're communicating with people and you're trying to be a useful mentor, conciglier, advisor, you need to be able to distill things in a way that the recipient can apply. And so if I want to be successful as a consigliery, I need to be able to translate things.

Is this why you're so popular on Allin?

Well, we'll see. I mean, hopefully it works. You know, Peter's very good also at conceptual frameworks. He published a whole book that has a bunch of them. But I try to be able to, either by metaphor or by framework, be able to articulate and translate a fairly complicated topic.

Yeah, it's very impressive. It's also kind of like, it's mesmerizing.

For example, the barrels and ammunition one did very well. So the, the question that I was encountering constantly from founders was basically simplified as I hired all these more people, I raised money, I raised, hired a bunch more people, yet I get less done. And it's very frustrating. Why. And so distilled it into this barrels and ammunition concept. That makes a lot of sense. Why? Oh my God. I've hired, you know, I doubled my engineering team, but I'm getting less done or I've tripled my entire, you know, team and I'm getting less done. It's because you don't have any more barrels. You're just stacking ammunition behind the same number of barrels. So you're not going to get any more done and you're just going to frustrate people.

Have you thought about writing a book?

I always get asked to write a book before ChatGPT. I thought the work. The work effort would be too high. I have started to play around with ChatGPT to write a book for me. So we'll see. The. Actually, the outline it came up with is actually pretty damn good.

Do you want to share?

Yeah. They had eight chapters. They were really pretty good choices. The title was very non intuitive and kind of edgy, which I liked. It was called Dangerous Minds. So we need to trademark that one quickly.

Yeah. Before this podcast airs. Yeah, that's really funny.

So I need to keep accomplishing things. Definitely want to make sure, you know that the book is interesting and that because the tension. The reason why I've always procrastinated, other than the effort, the serious reason is if you want to make it actionable, it needs to be specific. But if you make it too specific, it's not like a universal book. Right. There's only so many people in the company, in the world are trying to build a startup from scratch to like IPO or something like that. And so if I dumb it down to be broad, then it's not that useful to people who are aspiring entrepreneurs. If I make it actionable to aspiring talented entrepreneurs, how many people in the world are going to buy this book? So trying to finesse that balance, are.

We going to wait until after the open door turnaround that might be a.

Good idea or you know, maybe, maybe when ramp goes public or something or you know, some big moment that crystallizes everything. But I still need to solve this tension of making it useful to a wide set of Americans or worldwide wide set of readers and being specific and tangible, concrete enough that people who are very good, who already know what they're doing, find interesting advice in there.

I feel like you're already there. Like business is one of the top selling categories for books.

It is actually. And I think it could do fine. It would probably do well, but I don't want to do it unless I figure out how to make it like both a bestseller and concrete.

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You also have to carve time out because I've heard launching a book is like launching another company. You have to tour the world.

Yeah, I think that's true. It's getting some things are easier. Certainly crafting it through ChatGPT. Like the next step would be for me is to take one of the better chapter titles and ideas and ask it to write that chapter. But the more I do the podcast like this, more I, you know, do media interviews, the more content there is for, you know, chatgpt to train on. So that's why I'm doing this.

I'll give you the transcript. I'll give you the transcript. It's all training data. Well, talking about more specifically of like one of your superpowers. It's around culture and shaping cultures. There was one interview that I love, I think I, I tweeted about this. It was one that you did with Mike from Traba and Harry Se on 20VC.

Oh yeah, sure.

This one was fantastic. This was before like nine nine six became back in fashion.

Yep.

Which I think is like kind of bullshit. I think it's more than 996. But there was one part where you were all talking about building an elite culture. You need to build like Olympians.

Yep.

What is your framework for that?

Well, the framework Is every. Every. It's actually borrowed from Peter. Every successful company is a cult. And what a cult really means is you have a view about the world that's different than other normal people. And you're right to be successful. Like a cult doesn't have to be right, but the startup is a cult. That's right. And that's what makes a successful startup. So you have to decide very intentionally, from scratch what is your secret in terms of the market, the product, and your secret about people. Stitch them together into a set of beliefs. That's the cult. So the trauma cult is pretty unique. They did start with we're doing things in person in996 before it was cool. So this is. They started the company in like, maybe say, June 21. And at the time, lots of people said, oh, you can't do that. That's crazy. To me, it was like, duh. Of course. Every successful startup I've ever worked with from the time I got involved in technology in 2000, how exactly that culture. Actually, you're right. 996 was lazy.

Yeah.

I actually make this point to Mike all the time. Like, when I said PayPal, like 996, that would have been like an easy week.

Totally.

When I was a lawyer, 996, I would have been like, easiest thing ever. Like, I billed like 363 hours my last month as a lawyer. That worked. So, yeah. So, like, people want to be successful, have always been pretty dedicated. They have this attribute that they've adopted of Olympian work ethic, which is also true if you want to be a successful Olympian. Usually from the time you're somewhere between six and eight years old, depending on the sport, sometimes earlier, you start training and you train constantly, and you have a shot of qualifying for the Olympics, winning a medal, winning an NCAA championship. So they've distilled it that way, is you're working together with your team, just like people who train to be successful in sports. That's a metaphor that they use, a conceptual framework that they use.

Do you think culture has shifted since COVID Well, generally speaking, yeah.

No, it shifted, you know, in horrific directions. And. But I think it's being brought back. Like in New York City, it truthfully, people were working in office in New York City very fast after Covid. Like, at least when I've interviewed people or helped close candidates in New York over the last five years, nobody even asked the question if you have an office or you expect people to be in the office. It actually doesn't even come Up. Yeah, just. Well, of course you do. Or Miami, same thing. In the Bay Area, it lagged for a long time for a while, including, I'd say almost until 18 months ago. The only scaled modern company that I think was in office basically all the time was rippling. I think now you're seeing startups. I know Merkor is kind of, you know, very public about it and there's a lot more people building, you know, at the foundational level that way. But if you look at how almost every successful company was built, it's like heroic effort. And then once you stitch everything together and have a whole speech. I gave a lecture at YC in 2014 called how to Operate. Eventually you want to stitch this stuff together so it's a machine and. But you need the heroic effort to construct the machine. And there's no substitute for that heroic effort. In the beginning. In the beginning can be defined as the first five years, seven years, four years. Depends on how good you are stitching everything together and how fast you can build like this engine that just runs.

Yeah, I think in that interview you mentioned a quote that build a machine so strong idiots can run it.

Yeah, that's a Warren Buffett quote. But eventually, you know, we had a running joke in my PayPal days about we didn't think ebay was very well run and had a bunch of idiots, you know, his management team, which has proven to be true if you just look at the, the history of that company. But we had, the running joke was we had an over under bet of if Martians invaded ebay, how long would it take before the world to notice because they had a network effect business that the worst executives in the world were screwing up. It's really hard to screw up a network effect business for usually at least a decade. But I remember sitting in a management meeting at ebay after we got acquired, right after we got acquired and they hired some consulting firm as Bain actually to analyze the threat posed by Google to commerce. And their conclusion as a management team and with the assistance of Bain was, well, there was no threat posed by Google. Well, these days I haven't looked up Google's market cap, but I can tell you it's like at least 50x ebays all because they had management consultants running around and they believe these idiots. Where I remember sitting in the audience with Reid Hoffman and us like looking at each other during this presentation and saying, what the hell's wrong with these people? Like they're going to be toast in a matter of years and they were toast. They were toast. Both on two directions, actually. Amazon and ebay both destroyed. I mean both Amazon and Google destroyed them. And when we sold the company in 2003, they were the leading e commerce site, certainly in the West.

That's crazy.

So don't hire Meg women.

No, not that part. We'll leave that one out.

You can leave it.

Oh, gosh. Okay. So, well, that reminds me. So there's a calcium market that aliens. Do you think aliens will say that aliens exist this year?

That is a good question. Depends on that. I guess it depends on the definition of aliens. I don't spend too much time thinking about it, but I spend a little bit more time on the UFO stuff, a little less on.

What do you spend time on in UFOs?

Watching all these documentaries. They're kind of cool and interesting.

Which ones?

Oh, there's. There's a great one actually. Netflix had this really good one. It's. It's actually pretty fascinating. I forget the title of it. You can add it.

Okay.

It's pretty compelling.

Is it the one with the pyramids all over the place?

That one, it talks about this UFO landing in Australia in 1963, that they're both. All the kids who are very young, like 3 years old, all remember the same exact things. Even 30 years later. There's some actually evidence on the ground. But anyway, I let other people like be the UFO junkies and they report back to me. It's kind of a fun dinner conversation.

It is a fun.

I don't do conspiracy theories very much.

You don't know no conspiracy theories.

I'm not really. Now you.

Okay. So. Well, I'm going to still ask you one.

Okay.

Who do you think is running Elizabeth Holmes Twitter account? Sorry, X account.

I don't know, but I'm pretty good. We should hire him. Maybe get them to Open Door Media.

You should. You should definitely get them to do Open Door Media.

Do authentic Open Door. Like you may have noticed, Shopify executives from Toby to Harley to Kaz actually authentically post on X consistently. And that's part of their culture. And so I think we'd like to embrace that. Embrace retail as a movement. These are our customers. They're on a crusade and we should be transparent and use social media to communicate.

You are also very active on X.

Yeah, I've heard of the product.

But I have noticed like since joining Khosla again, your contrarian takes have. I mean, I'm not going to say they dulled down, but like you have gotten a little bit more Mellow.

Oh, my God, I'm getting old. Damn it. Yeah, well, I have better answer better thesis on this. My thesis is I ran out of contrarian takes because they've all been proven to be true. So, like, for example, I used to, you know, argue that stretching is bad for you and everybody thought I was insane. Like, this is probably the most controversial. And now there's evidence of why you shouldn't stretch second. Like, I remember, you know, Bloomberg wrote this profile of me in 2020, May 2020, where they described my theory on Covid as emerging as escaping from a lab, as a fringe theory. No quotes, no attribution to anybody, just dismissed it. Of course that's true. You know, I had like a bunch of contrarian theories about sleep, actually. So I grew up prioritizing sleep all my life. You can read interviews of me back in like 20, 20, 10 probably, when I talked about this and how is the most important thing you could do to be happy, healthy, wealthy. Obviously the evidence is incredible. Now anybody would even debate that the best thing you can do for your life is to sleep properly and, you know, sleep more up to a certain amount. And so I've been prioritizing sleep. I used to. Let's see. Well, I still believe that ketchup's really good for you when you're a kid.

Ketchup?

Yeah. People who are successful eating a lot of catch up when they're young. That one still gets a little bit of shocking.

So weird.

I haven't quite convinced everybody that yet. But if you do, there's a book that Tyler Cowan and Daniel Grossro talks about stellar people and their backgrounds. And they get close to that theory. They argue it with a sort of different, like, food, but it's similar. Malcolm Gwell also has a chapter on how ketchup is the perfect food.

Why?

I've just noticed, observationally that when I Sugary tomatoes friends, I'm like, how much ketchup did you have when you were a kid? Really? Yeah.

What. What is your view on the Diet Coke theory?

Well, so I've studied this one. I used to be a diet Coke addict. And when. I mean addict, I'd have between 8 and 10 every single day all my life. Like lawyer, entrepreneur. And then, and I read all the studies, people would say, oh, it. It's can't, you know, carcinogenic and all this stuff. It's not true. I read every single study that everybody would critique me. I'm like, show me some research and I'll read it. But then I got Convinced of one. There's a really well done study about eight years ago that took people with similar diets, similar body composition and allow similar calorie sort of intake per day. Allowed one cell of the experiment to drink Diet Coke. And what they showed in this study is that your body still produces insulin resistance as if it was sugary really. So you don't have the calories, but your body thinks it's insulin because of some combination of the ingredients and taste. And so if you spend all your life doing high intensity training and all these other things I do to avoid insulin resistance, it was kind of silly to be drinking Diet Coke is inconsistent with the goals. So I just stopped cold turkey, literally. I read the study, stop culture the next day. Have not had a Diet Coke in eight years.

Wow.

Literally not a single one. I used to have 8 to 10 a day. Like you ask anybody.

No water.

Sometimes like I run into people and they're just like ready. They haven't seen a while. And they like hand me a Diet Coke because I was so addicted to it. Now I have like green tea.

Which kind?

Iced? Any kind. Any kind.

Green tea ice, Big matcha guy.

And then I, I do have Celsius.

No, Keith, that is like worse than Diet Coke.

It depends who you ask.

Is it because you go to berries and it's there?

Celsius is, you know, like spiking your body a bit with caffeine.

Doesn't it have like heroin in it?

It's a proprietary formula. Nobody knows.

No one knows.

Look at the can. It's like a proprietary formula. The only thing they disclose, it has one of the active ingredients in green tea. Oh my God. Or something.

Jeez.

Have you tried $10 billion company?

It's a big company.

Yeah. So maybe, maybe, you know, maybe entrepreneurs should be innovating in that space too.

They should. Have you tried peptides? No, no peptides.

I have not tried any. I do have friends who are experimenting with them. People actually. Pretty interesting. Intrigued with the results they're getting. I'll probably run through a more rigorous like health care driven assessment with like one of my fancy doctors. But no, I've never tried any.

There is one thing that we need to address about berries. I read this online. You have publicly denied it, but there are rumors that you were doing push ups on your knees.

Oh, no, that's like absolutely absurd. The only possible scenario that would occur is if it was like my third class of the day and like I once in a while do take three classes a day, but Impossible, impossible. Impossible.

No way.

No.

Okay.

Army class though. If you've ever tried an army class in New York, sometimes instructors like three minutes of push ups consecutively and he gets really mad if you stop. So most of the guys eventually give out. But like that's pretty. The berries. It's impossible.

How do you have so much energy?

That's a good question. I think it's actually something you can teach yourself. Like it's an acquired taste. I think many things in life are that way. They're path dependent. You just decide to have energy and then if you have sleep, like, the truth is sleep is very effective. I do like things like cold plunges or cryotherapy. I believe in those.

Yeah.

I've got a little bit into this red light therapy stuff and reading about it, I can't really tell whether it's making a difference for me or not. But I've read the research and it seems pretty compelling with no downside. Send you stuff like that. But it's mostly I think just sleep. Adrenaline and sleep.

Adrenaline and sleep. It's good. It's great. It's good combo.

Yeah. As long as you recover. And I measure, you know, I wear this and have all these measurements on the recovery. But I basically don't believe in days off for anything. Work.

Yeah, I was listening. So in the Harry Sebbings podcast you were talking about. Okay, so even if you're not working, you're watching the highlight reels or you're watching back the tape.

Yeah. If you're an athlete, like it's not like you trimmed. Most athletes probably train six days a week, but the day they're not training, they're probably watching film. In football, they're certainly watching film. And so I think you can combine what you do just so like when I was running last, really running a company like at Square, Sundays would be work days, but I would be on a non calendar scheduled sort of approach, which would be I'd go in the office, I'd sit at a high desk with an iPad and with a huge red notebook and just draw my ideas. And people could come up and interrupt me, but I wouldn't put things on the calendar. So my brain would be at a different tempo and it allowed me to kind of brainstorm. That's why I had this huge red notebook that allowed me space almost like a mini whiteboard. And then I would be available for people who wanted to debate things, ask questions. And so it was a very different kind of day. And I think that can be effective, like rotating how you do your work is useful, just like training. Like, the problem with doing berries all the time is we do rotate body parts per day. However, the programming is pretty similar. So I think cross training is very good for your body. So I do like to lift and I like this army program. Unfortunately, it's only in New York, but, like, I think changing what you do once in a while is very effective. I like hiking too, if I'm like traveling.

Performance is a big part of building companies and investing in companies. There's a company you've probably heard a lot about. It's really popular. We're sponsored by Brex. It's this amazing company. They're all about spending smarter, moving faster, Intelligent finance, you're well aware of this, you love intelligent finance. Who is someone that you've learned a lot from and what was the biggest lesson?

Oh, I learned a lot from people constantly. Like, I've actually given a whole presentation, a whole podcast, a whole speech on, like, lessons I've learned from Vinod, Peter Thiel, Reid Hoffman, Max Lupchen. But I try to absorb from everybody. Like, found the benefit of working with a lot of talented founders is I've learned things from Christian at Trade Republic. I've learned things from Eric and Cream at Ramp. I've learned things from Mike Atraba constantly. The best, it really is, like, maybe the best part of the job. One of the two best parts of being a VC is you get to work with the most talented entrepreneurs in the world and you get to watch them and you learn things and then you apply, try to apply them the same. The other benefit is if you're intellectually curious, and this is why Delian became a vc actually is he's very intellectually curious. It's the only job where you get paid for learning new things. So every hour, every day is different. And I sit in a partner meeting and my colleagues at KV bringing in these very weird, unusual companies that are at the cutting edge of technology. And I learn. I sit there and learn by osmosis. And over the years, I've learned a fair amount about AI. I've learned a lot about batteries, things I never would have been capable of learning on my own. And so I really don't believe there's a better job for someone who's intellectually curious. I was intellectually curious from the time I was 4 years old. My mom loves to tell the story that we used to have the World Book Encyclopedia, and I read every single volume cover to cover.

Really.

That was my hobby.

Soccer, baseball, encyclopedias, yeah.

From scratch.

Oh, my God.

So, like, VC is like, that's what venture capital is. It's like reading an encyclopedia.

Can you recount everything you've learned from the encyclopedia?

Actually, I can't. I'm better, actually. Interestingly enough, my sort of oral memory is much better, really. So I can recount almost every conversation I've had with somebody.

Wow.

Which turned out to be. Is actually pretty useful. It's very useful as a lawyer. It's extremely useful, actually, as a vc in terms of board meetings. Like, so I typically run hot, meaning I run on a lot of boards. I serve on a lot of boards simultaneously. And sometimes I get asked, like, how do you do that? Like, how do you keep up and understand what's going on? And I've been fortunate enough to have a very strong memory, so I can remember numbers, metrics, presentations from years ago, and, you know, jump into the middle of a conversation and often remember better than the founder.

So do you listen to a lot of podcasts and audiobooks?

Well, I don't listen to too many podcasts. I do listen to 20 Minute VC. I've listened to Jack Altman's new series on Top. I found to be quite. Quite intellectually interesting, actually. But generally speaking, other than those two, you also listen to sorcery podcasts on an episodic basis. So, like, you know, once in a while I'll see a humorman episode. I'll be like, oh, that topic's cool. Like sleep or something and. Or cold. Cold plunge, Cold theory. Deliberate, he calls it deliberate exposure to cold or something. So once in a while I'll see a topic and I'll be like, that's cool. I'd rather read. So I like to read books. Like, real books, like old school printed books. That's how I learn.

What's your favorite book?

Favorite book is called the Upside of Stress.

Okay.

And is written by a professor at stanford named Kelly McDougall. And it really crystallized. So talking about conventional contrarian ideas, I used to believe stress is good for you. Like, I used to proselytize this everywhere to everybody I've ever met, from the time I was, like, in junior high school to forever. And everybody thought. Not everybody, but most people thought it was crazy. Like, they're like, stress is bad for you. It makes you, you know, sick and all. Blah, blah, blah, blah, blah, blah, blah. And then she wrote this book, and I discovered this book. And chapter by chapter, she argues in every possible way in an unequivocal fashion that the more stress you have in your life and the more you embrace it, you're going to be not only healthier, more successful, but you're going to be happier too. And so I give people this book all the time. It's the best.

We'll link it.

Yeah, we'll link. Link it to it. It'll. It changes people's life. I literally have had people come up to me after reading it and say, you just changed my life.

Wow.

So that's my favorite a lot. High Output Management by Andy Grove is the business favorite. I, for the first 18 years I was in technology, I reread it every single year and always found in my highlights, learning new things.

Wow. It's pretty insightful.

So those are the two to start with.

Those are good. Those are good starters.

The score takes care of itself. Bill Walsh, the lesson of how to build. Borrowing from football, how to build a company successfully. Those are the three canonical books for me.

That's a good starting list. Those are great. So we are just out of time, but I have like one question I've been dying to ask you. Have you ever swam in your fish tank?

No, you can't actually. You kill all the fish.

What's in there?

Well, there's exotic fish, but it's not, it's not. It's salt water. So if they got exposed to like any foreign body, they'd all die. So when, when, when the fish tank does get clean, like person has to wear like a wetsuit. You can't, you can't just jump in. Instagram influencer. Ask me once if one of the top, like three Instagram or tik tok Instagram influencer types asked me if he could like, oh my God.

Do you have a shark in there? What's in there?

Have a shark? No, no, there's. I don't think the fish would eat you or sting you, but it's just. They would die.

Yeah, that's not good. We don't.

No, it hap. They're very fragile.

Yeah. Okay. Well, Keith, it was a pleasure to have.

Pleasure to be with you.

Hey, it's Molly. If you enjoy our interviews, check out our newsletter Sorcery vc where we deliver a once a week top deals and tech headlines, email and also go deeper on our podcast interviews. Subscribe to Sorcery today and don't forget.

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