#403: Keith Rabois – Advice For People In Their 20s (From A Silicon Valley Legend)

Keith, welcome to the podcast.

I really appreciate you coming on here today.

Pleasure to be with you. So, I'd love to start with Margaret Thatcher. Why did you admire Margaret Thatcher?

Well, if you can see, I have Margaret in the dock right here. These are her, we'll actually do a live demo. This is all the official, this is Margaret posing for her official portrait and the one in yellow is the one she actually wanted as a birthday gift. But, Convenient question. So Lady Thatcher was the best in terms of principled execution and immune from criticism. So change society, maybe more than any other leader of the 20th century, based upon foundational principles in a meritocratic way. And and really altered the course of history through her own will. Other than that, it's a pretty good career.

Well, I found it interesting.

Here's what I did growing up. Basically independent thought, ability to think for herself. She used to say, I don't read the papers. They might deter me. She learned to assess ministers in three minutes or less, which was always my goal. for founders, but the ability to apply principles to change society in a hostile world is incredibly impressive.

I found it so interesting that you said when I got to meet her, it was like meeting God and that there was an aura around her. What do you think that was about?

I've never met any other human that had that impression. It was as if God just walked into the room. that it's always hard to describe, which is probably true if you ever did meet God. It's like these UFOs, you know, how do you describe like something that's, you know, out of this world? But it had that, like the magic and the energy and the attention and the gravitational pull as soon as you, like, walked into this little mini theater.

So Margaret Thatcher was one of your earliest role models. Who else?

Yeah, she, she, maybe the only one true idol growing up. Yeah. Um, my favorite expression too, to this day, actually I borrowed from her, but I didn't, it was actually subconscious enough that I didn't even realize it until last year. So, for like 30 plus years, I've been borrowing her favorite expression and using it as my own and not even know, not even remembering the derivation. So if her favorite expression was like, no, no, no, would be my favorite expression. and my babies now imitate me saying this, but I didn't really remember that as a derived from her. And I was watching season four of the Crown, and there's this scene in there where she says, no, no, no, I'm like, oh my God, that's where it came from. And I really forgotten this for over 30 years.

Wow. That's remarkable how we pick up on little influences from people that we admire like that and that we don't even realize it.

And that's been pretty foundational for me. I think part of the art of being successful in different fields is saying no, saying things no, not having FOMO, generally speaking, is a good thing. I have a phrase called JOMO, which is joy of missing out, and then saying no to things that are going to deplete your time and energy, not wasting time and energy. So no, no, no is really critical. That's why I'm actually somewhat happy that my babies are mimicking me already.

What's your favorite thing you've said no to in your life?

Oh my God, there's so many. When I lived in the Bay Area, I basically said no to every invitation, almost every invitation to go to any event, any party. They're all useless and destructive. So they basically refuse to go to any. Miami, of course, they have better things to do with our time, so we're more likely to say yes.

Before you went to the Bay Area, before you went to Miami, you met a guy named Peter Thiel at Stanford. And on your Wikipedia page it says, while at Stanford, Ruboi became acquainted with Peter Thiel, then editor and co-founder of the Stanford Review. I'm curious, it's very apparent to me from studying you for the past week that the most important thing you have is your ability to spot and be around talented people. And you could argue that that first meeting with Peter Thiel and meeting him set up the foundation for the rest of your life. So for young people, I mean, I'm sure you had been a success either way, but that meeting was impactful. So I guess for people who listen right now and are in their 20s, how do they get better at putting themselves in the positions and finding the Peter Thiel of their generation.

So a couple of pieces of maybe insight that are counterintuitive. So I met Peter and the details may matter here because I think it'll illustrate a pattern. I met Peter because I was sitting in my freshman dorm room and this random guy shows up just delivering newspapers, like printing newspapers. And it happened to be, he was delivering the second edition of the Stanford Review. It happened to be the guy was Peter. And so it wasn't like some orchestrated intentional plan, anything. And so I think the lesson I take away from that is the most important people you meet sometimes that will be foundational in different ways are in random environments. They're not consciously networked, et cetera. And the art is paying attention, like actually to people. Some of the most important people in my life I've met at Barry's in the middle of a class. And I think that it's when you're in an environment noticing things, noticing people looking for little signals of like who to filter, you cannot in fact spend all your time with everybody. So you have to pick up on little signals, but I watch other people I know, friends of mine, and it seems like they don't pick up on these little signals. And so I've had this conversation with them about trying to reverse engineer. I've literally had this conversation with one of my good friends. and went through the most impactful 20 people in my life and how I met every single one. And 18 of the 20 or 17 of the 20 are very randoms.

Could we break down some of those interactions and what happened exactly?

Yeah, I mean, literally two of the 20, three of the 20 probably met at Barry's in the middle of class, but I was mostly trying to do my workout. So you never know. Actually, five now thinking about it, I read that one who introduced me to his partner, who's my number two person, I'm hoping store at Barry's on a Saturday morning. It's just like always noticing people in nature that have some spark and then deciding to double down and invest more time and energy. So I think it's like always trying to find interesting people. It's worked pretty well, but it is sort of an acquired taste. I don't do any, almost none of the people that are important to me that I meet in any conventional way.

It sounds to me like finding the spark is really important. Looking at that and being like, all right, this person has something about them. Could you characterize that?

Genial or something intriguing? Definitely. And maybe at some point he developed some intuition. So let me tell you a story about Delian, my partner and a founder's fund, worked together for a long time. Now, how I met him, he was an intern at Square, which isn't that original, but there's a lot of interns at Square, truthfully, probably in his day, 30, 40 at least a year. And he reached out to me after his internship and he had applied and been accepted to a Thiel Fellowship. He's been dropped out of MIT. and he sent me this email saying, like, literally reads, I don't know if you remember who I am. My name is Delian Asperuhoff and blah, blah, blah, blah. And I wrote back like 10 staff in. So I was like, of course I know who you are. And so later, years after we became friends, two years later, he asked me, like, why did you respond to my email so fast? And I told him this anecdote, which was like, look, you were kind of a mess as an intern. You wore like tank tops and mismatched shoes and cause trouble and distract people all day long at work. But what was interesting to me, it was not that, it was that nobody complained. And so my inference from that was that you must be pretty good at engineering because people used at Square, when I was COO, people would complain to me about literally everybody and everything all day long. It was like the chief complaint officer is like my primary job. They'd be complaining about the food we were serving, they ever there. And so the fact that no one ever complained to me about Dalliance suggested that he must be really damn good to offset all his mess. It's crazy. And so when he sent me an email, I'm like, oh, this is a really good crazy engineer. But those people tend to do wildlife.

It's funny you describe when you're building some of these companies how you're looking for the data that doesn't make sense in a dashboard so that you can double down on it. and that's a perfect example of that as well.

We're actually connected to the dots that way before, we'd be delving into that story, but it's a really good comparison.

And I think what's so fascinating about you is how you've trained your brain or your brain has been trained to look for exponentials in not just data, but also people, which is a fascinating thing. When did you realize that about yourself? Because I know you spent your 20s doing law, which was not an exponential thing.

Definitely not exponential. But I don't, you know, and that's not sure it's exponential, but it is looking for outliers or anomalous data. The way I describe it typically is anomalous data. We had anomalous data at PayPal. That was pretty critical to the company's trajectory and history. LinkedIn found some anomalous data. Square found some very anomalous data that was also indispensable to the company's success. So I've always been attuned as a business person that what you want to find is anomalous data. And so maybe that's my grounding, foundational experience at PayPal. I learned how important it was. So the classic, why the retold story about PayPal at this point is how eBay, which was the important part of a market that propelled the company, was not in the top 10 target markets for the company. But David Sachs, who at the time was VP of product and later became COO of the company, said, aha, I see 54 eBay users rating in their listing PayPal with PayPal. he, a lot of his colleagues at the time wanted to keep those users out of PayPal because they were not in our target market. And David came into work the next day and basically said, aha, we found our target market. It's eBay. And so that was a lesson that was pretty impactful to me and probably then therefore look to apply that lesson in other places and maybe with people that I hadn't really connected to those two things before, but they're pretty similar. And now that I Now that you mentioned it, the people side is really, if you're looking for people who are gonna accomplish outrageous things or borderline irrational mission, they tend to have anomalous parts to them. Like the only people who change the world, change an industry, are pretty extraordinary in at least one dimension. And so if you don't see that extraordinary spike, the chance that this one particular person is gonna change an industry, reinvent it from the proverbial garage, or changing industry like music or change the world through politics is literally zero. So that means that's not going to be the next president I say. So it means it's not the person you should write a C check to, and that's not the next Kai Kaigo or something like that.

Were there any signs in your childhood that you were going to be someone who could change the world in some respect?

I don't know. I've heard some really funny, amusing stories, but I think they're all subject to a lot of hindsight. I did have some kind of irrational characteristics that were pretty good. For example, somehow the story I think my mom prefers to tell the most is, so I was five years old, I figured out that my younger sister was somehow poisoning the whole neighborhood at three years old with these little brace necklaces from Mexico that my grandmother had purchased for her. And at five years old, I had enough wisdom to go run home to my parents and tell them and complain about the kids in the neighborhood. all like doing this stupid thing. And it turned out it was actually poisonous and they all had to go to the hospital. They all had to get their stomachs like totally... And I was like the only kid who didn't do this at five years old. So somehow or another I had some brains, no early. But that's literally my mom's favorite story.

There was a sense in you that you shouldn't conform to the crowd.

Yeah, and that somehow or another, maybe I was too risk averse or whatever to do these stupid things. but it's also probably true why I've never used a drug in my life. It's the same Jomo.

Oh, wow. That's interesting. You know, a lot of people listening to this are in their 20s, entrepreneurs or want to change the world in some respect right now. And I'm curious to go to the place of being a lawyer in your 20s. And you've said before, after 3.5 years of practice and a year and a half of clerking, I realized there might be better things to do with my life. I basically wasted all my 20s practicing and studying law. Almost anyone who's under 30 listening to this is almost surely better off to a better start than I was.

That's pretty much true, right? I wasted a decade teaching the wrong thing. So, yeah, I definitely could have, you know, the opportunity cost of that decade is pretty high.

Take me back to the moment you realized that.

Well, what happened was, you know, I had the benefit of attending Stanford with a lot of people who built things during the first generation of the internet, known as now known as the internet bubble. And they were, many of them were constantly calling me up during my legal days from like the late, in the late 90s, trying to recruit me to like leave, I was on the East Coast, like DC and mostly New York. And they were constantly saying, you gotta come back to Silicon Valley, you gotta come back to Silicon Valley, like, you know, gold rush, blah, blah, blah, blah, blah, all this stuff. And twice a year, I'd go back to the Valley, check it out more actually truthfully to visit my friends than to actually check it out. But it was a good excuse to say, I'm like, you know, professionally, you know, checking out opportunities too. So in any event, I would be back in the Bay Area about twice a year. and these people were constantly trying to recruit me or hire me or whatever. And then after three and a half years of doing this, you know, trek to the Bay Area, the height of the internet bubble, literally the height of the internet bubble in February 2000, I actually decided to be crazy enough to join them. And so six weeks later or so, the entire market collapsed. So probably a sign of the times that you could get like a conventional lawyer or risk averse lawyer like me, to drop out of litigation and become an entrepreneur. But I did. And then when the market collapsed, I was maybe foolish, maybe not. I decided to double down and just like, okay, we got to make this work somehow. I don't know if I really knew what I was getting into when the market collapsed again in June. And it was, you know, five-year pretty much difficult time in technology, but I didn't abandon it. I stayed with it, made it work, and, you know, I've been doing it pretty much ever since.

What I'm interested in is the decision making process. You've had a bunch of these calls over and over again. But it was like, why in February of 2000 was that the moment that you actually took the jump?

Well, the superficial answer is I built 360 hours in January of 2000, which I do not recommend to most people. Oh my God. Do some simple math of like, That's build not work. So there's a discount factor from work to build.

How many hours are there in a month?

Not a lot more than that. Yeah, it's really hard to build 360 hours, trust me. So in any event, it may not have been totally accidental the month after is when I quit law. But there was a specific opportunity, a specific person who's recruiting me And it was intriguing enough. I felt the person could teach me the fundamentals of internet businesses so I can get up the learning curve. I felt the business and what the company was aspiring to do made sense for some of my background. And so the combination just clicked. And then I called up, had one, maybe two friends, I called up and asked for advice. And, you know, their feedback was very strongly positive that I should do this, I should embrace the opportunity. said I decided kind of on a whim to do it. And then, you know, jumped in cold turkey, started, quit, started, and, you know, and survived.

What did you learn in that first year?

Actually, a master's in our thing. That year was incredible learning. Maybe the bacheloring, you know, year of my life. I had to pick up business from scratch. I literally knew nothing about business. I never touched business before. and how to run important components of a business under pressure as the world, the NASDAQ was collapsing and the world of internet technology companies was collapsing and the finance was collapsing. So it was a great learning environment from that perspective. How to learn to manage people, I'd never managed people before. So all this, I had to learn it. That's great learning, but I had to learn how to do it. I'd never built a spreadsheet before, I'm not sure I ever built one after, but I never had to learn how to use Excel. which I still have not mastered. But anyway, I've learned all business strategy, business thinking, hiring, recruiting, managing to some extent all in like six months. Wow.

And then when did you deal with the state of Louisiana, I believe? That was three years ago.

That's like February 20, February 2001. So the precipice of our IPO at PayPal. We received this unfortunate letter from the Banking Commissioner in Louisiana that we were allegedly practicing banking without a state license. So that caused a real problem because it was literally the premise of our IPO. And it was more complicated than it even might seem, and that might be scary enough for most people. But what happens is any delay in our IPO, we had like a, maybe a 10 day buffer, or we would have kind of missed an entire window to go public. our finances would have been, quote unquote, still, meaning they would have needed to be re-audited, that would introduce all kinds of uncertainty. So we really needed to get public and so we needed to fix this problem very fast.

And yeah, I mean, it seems like the amount of things that you have dealt with in your career of insurmountable odds and finding a way to talk to the state of Louisiana and rewrite the laws, like, that's a remarkable thing.

And so, you know, interesting enough, so I'll tell you how we solved this. It's a little bit different. We, the first instinct of the, you know, company CEO, Peter General Council, John is very good. And Reed Hoffman worked on this really closely, was we hired all the right obviously, Louis, Louis, Peter had some connections there to a lawyer he went to Stanford Law School with. And so we were in the right hands. We just still couldn't unshake, you know, the commissioner of his stop. And so I had this, like, random question. I said, you know, in the middle of, like, kind of a random brainstorm meeting, well, how many users do we have in Louisiana? And, of course, nobody knew the answer cold, but. So we quickly ran a query, and we found out it was actually a decent number, like, measured in the low thousands, but Louisiana, that's a reasonable fraction of voters. And I was like, okay, great. Well, let's just tell the commissioner that we're gonna have all these people call up and, like, you know, send them emails. And so our lawyers kind of conveyed that, like, you know, there's all these people whose livelihood is being jeopardized by the commissioner's arbitrary and reckless behavior. And, you know, these people are definitely voters and they want to complain. Who should they complain to? So all of a sudden, within 12 hours, they were like, you know, your legal arguments are a little bit more compelling than we thought. You know, maybe you're not practicing banking, blah, blah, blah.

And so it went away. But it was all because we had 3,000 voters in Louisiana and that's a.

Meaningful fraction of the state.

So you took advantage of the resources that you had to execute against the strategy at that moment?

Yeah, in fact, I actually wound up passing this lesson on to some people I knew at Uber back when they had problems. And they actually leveraged this very successfully in DC, I believe. And then later, written large, DoorDash, Uber did something like this. on a proper statewide proposition in California.

Speaking broader about like this topic about you have preexisting laws that exist and then you have technology disrupting that whole arrangement. There's going to be some friction and some battles that are always going to be fought. How do you best convey to the structure that is present what is coming?

Well, generally I wouldn't. Part of the art is Peter actually coined the phrase, as far as I know, too big to fail in 2000, 2001 at PayPal before it became a popular expression. And his basic point was we need to grow really, really, really fast at PayPal because all the people that don't like us in government entities, Visa, MasterCard, these monopolies, eBay, they won't have leverage if we're large enough. we need to get large enough. So you're vulnerable. When you're really small and cute, nobody cares what you're doing. And then you become larger and people get terrified. And that's when your enemies can strike. And then you, if you get too large, you become quote unquote, and Peters view too large spell. Then you have all the, you have counterweight, basically, of users. You have an assault base. You have people really satisfied with you, and you can deploy them. So the art is to close that gap between too small and cute and too big to fail as fast as humanly possible. So that's what I've been recommending. You can see other people have kind of followed that playbook. Often borrowing pretty consciously from the playbook.

What's the part of- yeah. What's the part of the journey of that journey that you find most joy in?

Oh, well, first of all, growing. Creating momentum is great. I mean, inertia is not your friend, it's a founder's purr, it doesn't matter whether you're regulated industry or not. period. You need to overcome inertia and turn it into momentum. That is the most value creating exercise in many ways. So that's fun if you can get it right. And then that does allow you to have leverage against large incumbents that may or may not like what you're doing. Whether they use a political process, a legal process, or business process to try to slow you down, if you get the right momentum, you can punch back.

And part of that process, I'm assuming, is having 70% conviction and actually making decisions when you do so.

Yeah, so anytime you're going to play around in the political process or regulatory process, it's going to be somewhat controversial because there's a chance it backfires. You can't always totally control. You can get insightful and smart and savvy about whose interests are what and how to play those cards. I spend a lot of my time at PayPal actually working with 17 different lobbyists managing the federal government. But anytime you pull that kind of trigger, there are some dimensions that you lose control of. And so you need to be prepared for the downside too and be able to educate your team, your executives, your CEO, your board about, I'm playing with a bit of fire here. The probabilities are great or we would not be doing this. But understanding there's a lot of art to when and how to do this is absolutely critical in a regulated industry.

Is there a moment that you remember from the fire blowing up in your face and that that was a pivotal moment for you?

You know, I'm not sure it ever really has. I think sometimes you get too nervous yourself, which is part of the job. A lot, it definitely had a lot of sleepless nights about things, understanding the way things could backfire. But I don't remember a time where it actually backfired. Wow. Maybe that means you should do more. I mean, the lesson may be people worry too much.

Yeah, that's interesting. Talk to me about where currently you believe that there are breakthroughs that are waiting to happen. I know because I know that everywhere. It's everywhere. But when your vantage point, having been so close in so many technologies, where is the current oh, wow. Like, how are we not further along on this axis?

Well, you know, honestly, I don't really have any answers to this because I don't believe in, like, trying to predict the future of technology. I believe in that. That's what founders do. And the right founders find opportunities to leverage a new opportunity, a new capability, a new technology, and turn it into something great. So I just sit back and wait for a founder to walk into my office and say, Here's the future and I can deliver it. And then I usually say, Here's your money.

And then in what you're looking for people who have greater than a 1% chance to change the world and you're looking for a spark and seeing that person, how do you identify that that's the right person that could actually make that change happen?

Well, you never 100% know, but what you do know is the probabilities are greater than zero. And so, the upside of changing the industry of the world offsets some mistakes because the upside is real, both in terms of impact and in terms of financial impact for an early stage Series A investor, which is mostly what I do. And so the art is trying to figure out, does this person have an unfair advantage vis-a-vis the rest of the planet in accomplishing this? And if you feel that they do, then it's a pretty good early investment decision.

You've said before about the importance of the upside of stress. That's one of your favorite books, and if not the favorite or most recommended. And I'm curious, at what point in your life did you feel most stressed?

I like stress. I kind of crave stress, adrenaline stress. So actually when I read the book, it wasn't like anything new for me. I believed all of it. The best thing about the book was that I had something to proselytize and give to other people. I was failing with some people, like convincing them that I was right. But then she, the author, Marshall B. All the evidence is incredibly compelling. There's no way to read the book and not change your life. So it just reinforced everything I believed, which is stress is the reason for living, which is challenging yourself. You need to challenge yourself every day. You're either growing or you're decaying. And if you're not challenging yourself, you're in decay mode. So actually, new and challenging all the time.

At what point do you feel most stressed or what point have you in your life?

Well, running a company is challenging constantly, mostly because as I talked about in the YC lecture, how to operate, recognizing people is constantly draining. The reason why is everybody in any organization of any size has different interests, has their own personal professional family issues. And so you have an assembly of a couple hundred people. And if even if only 1% of the people have a problem every day, that's your problem too. So it means you have a problem every day. And so navigating that is pretty draining actually compared to all the intellectual stuff is actually pretty easy and not very stressful.

Do you feel like you take on the problems of other people like more so than the average person?

I think if you're an executive, you kind of have to, like, for your team. Like, I don't think there's any way around that. Like, Jeff Jordan taught me this back when he used to run, like, eBay and PayPal is like one percent. He taught me the proverbial expression. One percent of your employees will have a crisis every day. And, you know, you do the math when you have 365 people. That means you have a crisis every day.

And what do you do then?

Obviously, you, you need to help them. People navigate the crisis and that may be sometimes like substituting the people or, you know, but often we can help them. Depends what the source of the crisis is. But I've seen every kind of this crisis. Like either at Square, we had this, you know, unfortunate incident. We moved this colleague from Seattle down to there. He's going apartment shopping and he gets shot. Like literally this week apartment shopping before starting work. Like this is what happens, you know?

You got shot?

Yeah, it's like San Francisco.

Oh my God. Wow.

And obviously that's, well, the time is more extreme. It's probably more common these days, but like, but, but it's just an illustration of every day there's something, some variant of that.

What makes for a great leader?

That's a good question. I actually think it's hiring. you know, the team you build is a company build by borrowing, you know, a lesson from Vinod Khosla, but it's a little bit like sports. You can be a pretty good coach, but one way to be a pretty good coach and be very successful is to have the best athletes. So there's not a lot of substitute for talent. So the best thing you can do is learn how to recruit, source, recruit, assess, and close amazing people. Amazing people will do a lot of amazing things more often than not. critical density of talent, like being able to assemble critical density of talent.

Could you take me through the process of you doing that with a specific person?

Well, yes, because I think the art of assembling a critical density of talent is you have to look for people with either different traits or in places that other people aren't looking, otherwise you won't get a monopoly on talent. So this is a lesson I borrowed from Peter Thiel, like the first week. We had PayPal. He took me on a run, jog around the campus to check, you know, to check in with me in my first week, see how things were going, get feedback. And he kind of taught me this lesson that the only way to scale a startup is hiring undiscovered talent. You don't want to be competing on comp and assessments with like all the large players that be. You're never going to win that battle and create, you know, unfair advantage and talent density. And so that I understood the logic right away, like in the middle of the run. The challenging part is actually doing that. Like how do you find these people? How do you assess them correctly and then manage them? And so all of those took me years to dial in, but I think I've dialed them in pretty well. So I've been able to find very consistently across the last 23 years, undiscovered talent, empower them and watch them really succeed.

I was talking to Jack, your chief of staff before this, and he said, how, I asked him, how do you get the job? And he said, I just kept asking. And eventually, there's some truth to that.

He also worked, he also worked really hard. He would be the first person in the office most days, you know, insisting that he was in the office by nine. There's a lot of other traits, like, that's just a little bit of implication.

So what else did you find in him? Because I'm, I'm guessing there's a lot of people out there who would like to be Keith Robois, chief of staff, or do some work for someone similar?

Well, the role. So this role is a little different than most. So part of what you're doing is a little bit like speechwriting for the president or something. You're really trying to absorb someone else's brain, not really develop your own per se in this role. So when you're hiring for this kind of role, I think the key insight is what's the likelihood of the person, how fast and how likely can a person absorb your brain? Because they really do need to mirror your thoughts. And so there's a projection from that. So, you know, Delian, as I mentioned, was my first chief of staff. I never really believed in the model before, but I tried it out and it worked really well. So Jack's now the fourth, you know, fourth chief of staff. But a lot is what are the probabilities that the person can really mirror how your brain works.

That's a very useful skill, mirroring and absorbing someone's brain.

Talk about like actually the metaphor works. Whereas a law clerk, this is the first job you do if you're kind of a prestigious law grad, you clerk for a federal judge. And so my goal would be to draft opinions for the judge. And if I was doing my job really well, she would like the draft and have to edit it virtually, not at all. It's a real high order bid. I used to be really frustrated with her red lines and be like, try to get better and less red lines. And, you know, eventually she knew, she knew I was doing this. I'm like, counting every red line is my mistake. She's like, it's okay, you know, I could do some of the work myself.

You can make mistakes, it's allowed.

Yeah, anyway, you want to be drafting an opinion that is consistent with her views of the world, that is implementing as if she had infinite time, what would she want to have drafted? That would be my goal as a lawyer. So you kind of learn that mentality and then just apply it to the business world.

How would you suggest someone get better at that skill?

That is not easy, actually. I think you can try reading the same sources, like the raw materials and stuff. I'm not sure you can learn it so easily. I think people have sort of brainwave matches and not. There's a famous study at Dartmouth that's been connected over the last five years with MRIs that you can kind of predict who's going to be friends with who based on their brainwaves.

Oh, wow.

I'm not totally sure, like, you can just learn to mirror, but, like, speech writing, same thing. I think there are some speech writers who are very successful and more malleable. And then there's some people who had, like, Reagan's voice perfect, perfectly, like Peggy Newden. And I'm not sure if Peggy could write for Obama or vice versa.

One thing that comes to mind is, is actually writing out by hand the speech that you see or particular writing that you like because you'll get more in the flow of that person's thinking.

I think that works really well. It's a trade I used to use all the time as a lawyer and when I was speech writing. Jack Dorsey also used to do this at Square. He'd handwrite important presentations. I think it trains your brain really well. The absorption is pretty critical. It fills in logical gaps. I think it's an excellent exercise.

Yeah. Going to advice that you once believed but didn't, you said, For 40 years, I believe success required unique insights or secrets. Now I am persuaded that it mostly just requires ignoring the stupid advice people dispense. I think most of success is pretty much common sense.

You just have to do it every day consistently. So there's lots of fancy thinking out there, like blah, blah, blah, blah. If you just do the right things that everybody knows are the right things, but you do them consistently without excuses, You wind up in a lot of good places. So I think just crowding out the noise and crowding out the excuses. And there's lots of sources of excuses. There's always some like, well, what about this or what about that? Or I don't feel well today or blah, blah, blah. And it's just like doing the most fundamentally sound things you can as consistently as possible.

What's the worst advice you've ever received?

Great question. I don't know. I'm pretty good at filtering out really bad advice for myself, usually. Okay, probably guys in one ear out the other pretty quickly. So probably doesn't get much attention.

That's fair. Because in order to know good advice, you have to have applied bad advice, I feel like.

Yeah, no, you definitely have to learn. I mean, look, you do learn from mistakes. You don't want, you they're only making as few mistakes possible to learn from other people's mistakes, blah, blah, blah, blah. But it is impossible to try to do something difficult and not make some mistakes. Venture is the perfect animal for that. If you're extraordinary as a seed and series A investor, you're probably right 40% of the time and wrong 60. So you're gonna make a lot of mistakes, like playing baseball. You're not gonna get a hit every at bat, and it's like insane to think so. So you definitely have to know the degree of difficulty of what you're trying to accomplish. before applying, like, is this a mistake or not? The kind of mistakes I care about are things that could have been done better, thought about better, made better decisions with information that was available at the time. That stuff definitely is more painful. I don't really try to rethink things that didn't work out because a lot of times you couldn't have made really a better decision at the time with the 70% confidence intervals.

What's the most painful mistake? that comes to mind?

Not. Well, I signed a signed term sheet with Robinhood to leave to leave their seed. And they came back with a request afterwards to join their board. And for variety of reasons, we decided at KV that I couldn't do it. That was pretty painful. Rippling. I also was one of the two people that extended a term sheet to Parker in the seed round for Rippling. and had another offer at $10 million more valuation. And I probably would be able to be the lead investor with a moving by $5 million. So that's extremely painful.

Yeah. And are those chips on your shoulders now? What drives you today?

Well, so the reality is with the Robin Hood mistake, I definitely learned from the lesson. So kind of a similar situation presented itself with a company named Fair. So, to the co-founders of Fair had worked with me at Square, played soccer with me forever. And so I knew I wanted to lead the vast, lead the vast in the round, et cetera. But they explicitly required me to join the board. And I was like, oh, God, this sounds like Robin Hood all over. And so what I decided to do is say, yes, I will join the board. And I just decided not to tell my partners at KV this time so they couldn't talk me out of it.

I think they're happy now. I think it's going to return the fund. you mentioned the soccer, didn't you? In your, when you were starting in Silicon Valley, didn't you start with having.

A soccer league of some sort? Well, yeah, it was, like, less formal, like, towards the second or third year at PayPal, when things started to work, we started playing soccer a fair amount. And then I brought this over to LinkedIn. We had a LinkedIn organized soccer game at least once a week, maybe twice a week. You know, some LinkedIn colleagues and friends of mine, like, my friend Rolla Bojja from Sequoia. I once broke his ankle playing soccer, which he will never forget, never forget about. But he still has X-rays on his phone to show people that this is what I do to people. But in any event, it wasn't intentional. But anyways, we played soccer, and then later in the Bay Area joined a much more aggressive serious soccer league, probably like 2008. But like the LinkedIn and all was more like fun, entrepreneurial, but pretty talented group.

Yeah, I think that's just great advice for people in their 20s. It's like find a way to do some activity that gets you sweating with other people doing something similar to you.

I funded a few people off the hired or funded a few people off old soccer teams. So soccer, they generally done pretty well.

Really?

Yeah.

So soccer buries those seem to be common. Places that you find talented people.

Yeah, I mean, like, think about it. I'm gonna play soccer anyway, or back then definitely play soccer anyway. And I'm gonna go to areas definitely anyway. So might as well turn into opportunities.

To spot talented people. One of my favorite takes from you is that I've never found humility to be correlated with success. In fact, I find it inversely correlated because it's so interesting how in today's day and age, we put up humility as a virtuous trait. But you make the argument that it's not.

Yeah, I mean, the benefit of having some successes, you get introduced to a lot of people in other fields, like famous athletes, famous DJs, famous politicians a lot. And none of them were successful or humble. Like, you may not know it sometimes from the public persona, but like, definitely these people have significant confidence in what they're doing. And it's backed by reality. That's the difference. is, you know, Joe Namath, who is a very famous quarterback for the Jets, you know, once said, if you could, if you can do it, it ain't bragging. And basically most of these people are kind of have that personality trait.

Do you think that the bravado came before the actual action?

That's a great question. I think sometimes, yes, because people know when they're really good at something. So I once had this conversation. I was trying to explain Angel investing to Derek Jeter. and he kind of, he's asking me like, what I do sort of, I was trying to explain it and I said to him, when you see a rookie in spring training, can you tell from the first about whether they're gonna be successful? And he said, yes. And I said, so how do you know? And I, when I asked the question, I thought it'd be like something they should put in swing or, you know, some of the technique kind of thing. He's like, the confidence. Wow. And I was like, that makes so much sense because actually the reason why someone in spring training for the Yankees back then, would have confidence is they know their technique is good. Like they don't, it's like, it's like recursive to the, the fundamentals are sound. That's what leads to the confidence. They know their bat swing is like impressive, you know, etc. So I think that it, you can, you can triangulate that, but you have to have, sometimes you have to get to, people are taught to suppress it. So it's not obvious, all these people, it's not obvious when you first meet them. I'm not saying it's publicly obvious, but when you meet them and get to know them well, there's definitely a lot of confidence. I mean, Made fun of my friend, Kaido. He opened his act, obviously a quite good DJ. He opened his act in Ultra last year, I think it was last year, to one of his better songs called Stole the Show. And so afterwards, I was like, that's pretty cocky way to start your set. And him and his manager laughed.

Yeah, because he believes he stole the show and that his presence there was.

Fine, but opening to it's a little aggressive. Yeah, that's what I was making point for.

So you're hanging out with Derek Jeter, Kygo. At what point did life feel different for you? Like, oh wow, I've been waiting for this.

To be clear, it's not a daily activity. I just like, one of the things that's interesting to me. So I have that personal interest in sports and EDM music. So like, it's not accidental. But more importantly, what I've noticed is when you talk to successful people in different fields, how many calling, common characteristics there are. And so what I'm always doing when I'm talking to people like this is asking them questions about their field and what's led them to break through. Like, how did they become successful? Like, why? Why them versus other people? Can they tell which upcoming DJs are going to be successful or not? You know, how do they, what are they looking for? And so that's what my brain is actually trying to train myself by talking to them. And it has been shocking to me over the last maybe 10 to 13 years of having the luxury to meet people like are pretty successful in different fields. how common the characteristics are. So for example, I'll give you a tangible example. One of the first times I got to hang out sort of on stage with like a really good DJ in the middle of his set, I noticed that for the stage you can actually see all the people in the audience's eyes. Either is assumed in the audience as this anonymous figure, you know, kind of blah, blah, blah, blah. And so I mentioned this comment to this DJ. And he said, yeah, yeah, yeah. That's how I can tell my songs are working. I just look to see if they're staring at their friend, if they're looking at their phone, and I'll edit the song, you know, change the song, like based upon, like, whether people paying attention or not, I'm just looking at their eyes. And as soon as he said that, it's like, oh my God, that's like for speaking. Like I do a lot of public speak speaking stuff, you know, with audiences, Q&A. And so the goal is to not let anybody in the audience, I should be interesting enough and provocative enough. that nobody in the audience should be picking up their phone. And actually, I've given two presentations in the last year where in the last six months, actually, where it was really true in an audience that typically on average would pick up their phone every couple of seconds. And that's how I know I was interesting, is that I've actually literally taken this lesson from a club in Vegas and applied it to purely professional endeavors.

It would be so interesting to track the amount of times that someone looks at their phone while someone's giving a.

Speech to calculate Truthfully, it's really, especially for an audience. So both these, both the audiences I did this recently at where we're both CEO audiences in their attention span is quite limited. And if you're dry at all or not interesting at all or not useful at all, they're immediately grabbing a phone. And so, but they'll pull it off twice in a row. But it really derives from like this, you know, kind of the experience I had in Vegas of all things.

So, so cool. I like to end these podcasts with challenges for people, challenge for the audience. Is there something you can challenge the audience to do to live the best possible version of their life?

Well, I think it's read upside of stress if you haven't already and apply that to your daily lives, your professional life, your personal life, and try to find a challenge every day, something that challenges you every day, and then you'll be growing every day and you won't age if you're growing every day.

Keith, thank you so much for taking the time. I really appreciate you. Where else should we send people to.

Connect with you further? Well, most people follow me on Twitter or chat @rabbleway. There's lots of podcasts, but they're pretty random.

Yeah, linked below, as well as some of the ventures you're up to. Thank you so much for your time. Thank you.