Cold open
I have strong conviction that we’re in the early years of the biggest bubble. NVIDIA becoming the most valuable company on the planet is just the precursor towards the bubble of all bubbles. What are your biggest lessons from Peter? He just views the world under a different lens. And with that lens, he’ll see something very different from everyone else. If you look historically over the decades, if you just sit on all the companies when most will go to zero, your power law winners will be so massive. They’ll just dwarf everything else. I’m not practice of selling, I’m in the practice of finding and building companies and sitting on these things for life.
Intro
My word, what a 20 VC we have in store for you today as we welcome Kevin Hartz to the hot seat. Now, do we think Kevin is the most successful angel ever? Check this out. He did Airbnb, Pinterest, PayPal, Ram, and Anduril as an angel. He’s now the co founder and GP of A* Star with over $600,000,000 in assets. And before becoming a full time venture investor, Kevin co founded Eventbrite, a publicly that he served as the CEO for the first eleven years of the company’s lifetime.
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Conversation
Kevin, I cannot believe that we have not done this in person before. First, it’s wonderful to have you in London. Second, thank you so much for joining me today. Thank you, Harry. It’s wonderful to be here in London. That is so kind of you. And as I said, I love doing this in person. It’s so much nicer for me. Dude, I think so much of who we are is shaped by our childhood. So I remember when my mother got MS, and it really was it was hard, but it was a very defining moment for me.
When you think back to your childhood, what was a really defining moment for you that sticks out in making you the person that you are?
Harry, you know, I always look for founders that have overcome some incredible obstacles or moved mountains, and my childhood was fairly uneventful. I just had an idyllic childhood all the way through, you know, wonderful parents and went on to Stanford University. I’d say I hit my kind of life crisis or uncertainty post university.
What was that?
I would just say I had a crisis of how I wanted to have an impact on the world and very fortunately happened to be in the right place at the right time. And that is in Silicon Valley during this incredible first wave of technology innovation in the internet. Boom. I was lucky.
Can I
ask
you a weird question? But did you think that you would be successful when you were young? Often people have sometimes inevitability of success. They knew that they would be successful.
Most people I talk to that are founders that have gone on always knew from the very beginning. And I would look up at my father who is now a retired attorney, and I would say like, wow, how am I ever gonna do better than my dad? He’s a partner at a law firm. Wow.
I love that. And it also goes against the, like, what you hear, which is like, I always knew I would be in this inevitability, which is almost quite hard for people listening because it’s sometimes insurmountable. It
is. And I think it wasn’t a drive for success. It was a drive for learning and really not to be bored. And that’s why Silicon Valley is just so intriguing, so intellectually stimulating to all of us. It’s like why we really do this.
I think, you know, childhood shape us, but so do the people around us. And I spoke to Julia before the show, and she mentioned three people in in particular who maybe shaped a lot of who you are and how you think just from the time that you spent with them. One of them was Peter Thiel. And as I wanna start on this, I’m a huge Peter Thiel fanboy. What are your biggest lessons from Peter? And how did Peter impact your mindset?
Yeah. I’m a huge Peter Thiel fanboy. The things he he says are indelible. Like, he’ll say things that maybe don’t register at the moment, but then later on, you’ll really understand, you know, what it meant. He sees the world in in a different manner. I I would say that Peter, like a lot of people at Stanford, is incredibly brilliant. But it’s also that he just views the world under a different lens. And with that lens, he can kind of tease things apart and interpret things in a way that when you look at an object or you look at, you know, one of these tests of an inkblot, he’ll see something very different from everyone else.
I spoke to Roelof last night, actually. He’s, again, another, you know, hero of mine as an ambassador. Both South
African, Peter and Roelof. What did you learn from Roelof? Roelof was just always metered and always has sound advice. I I don’t mean to make him sound like a boring person, but he is, you know, in the biggest crisis when the ship is being thrown left and right. He is steadfast and calm, and, you know, somebody of such good judgment and insights and so worldly is absolutely somebody you want in your back corner.
The final one is Pierre Lamond. It’s an interesting one because it’s a different profile to both Peter and Roelof. Not South African, French. Totally. And also operator based.
Yes. So
Pierre, what was the lesson there?
Pierre is all about excellence. And, you know, how do you uplevel to be the greatest company in business and operator that you can be? And he always had extremely high expectations of everyone around him and the companies that he’s involved with. And maybe to give an impression, because I think it’s very applicable today, when he led the investment for Sequoia, it was Pierre and Roelof. Roelof was the junior partner, had just joined from PayPal and invested in in Zoom. And when he led that investment, we started to have regular one on one meetings.
And in the very first meeting, I’ll always remember he said, Kevin, I want you to go up to the whiteboard and I want you to write your direct reports down, but I want you to force rank them, you know, one to seven or how many was. And so I go and I write the seven names down. He picks up the marker, walks over to the whiteboard, and he crosses out the seventh name and he says, fire that person. And it was a shock to me, but I do see what he was trying to get there, and that is that excellence has to abound in an organization and no room for error.
And he was sending a very powerful message by doing that.
Speaking about kind of the talent assessment that, know, Roelof, your wife, many other people, founders that you’ve backed said that Kevin’s greatest trait is his ability to spot truly unique talent very, very early. This is from Roelof saying that you’re the best in the world when it comes to this. How do you identify true talent from people who are just pretty good at selling?
You know, I’ll say a few things. I like kind of head shrinking, you know, teams and CEOs. I like to learn about their background. I like to hear what hard obstacles they overcome. And so I got a little embarrassed when you asked me about my background because I probably would have never given myself a check for, like, growing up in an easy, waspy, white middle class American town with no hard upbringing and a town full of lawyers and real estate people and doctors versus, you know, people like Max Levchin that, you know, escaped from Eastern Europe and, you know, Chernobyl.
Well,
let’s play a game. How did you first make money? Did you ever do anything when you were young in terms of anything entrepreneurial? Quite
a bit. You know, I always had like a little shtick going, and I wonder where that came. In college Like how old were you? I would say I was always kind of like selling things on the side in like my teens. But in college, I actually had a Facebook business pre internet. Oh my god. That’s old. It was called faces in the crowd and it was a picture book of students on campus. And, you know, we would get all the students photos and we would get advertising from, you know, all the local places, and then we would sell the books.
And I think I should probably go after Meta at this point now.
Did you do well in school and did you enjoy school?
I loved school. I loved learning. I had ADHD and had to take such a broad variety of classes of every sorts.
Okay. So it’s interesting. You just said that you wouldn’t have given yourself money, but like when you actually do the background test, which is exactly what I just did on you on Founders, that you would be smack bang in the middle of my, I’ll give you a check. Why? Great entrepreneurs always start something early. No one starts something when they’re 25 having come out of MIT or Stanford for the first time. Always their entrepreneurial flair early. Two, you either hate school or you love it. People that are okay tend to not be great.
Really interesting. The binary is where you get great. And then also, like, ADHD is another, you know, as well as I do, clear sign of, like, the best founders have it. Kinda actually a weird one, and I had Ara from Service Titan on the show last night. I had Daniel from UiPath on the show a couple of weeks ago, and they both said if they had got $5,000,000 rounds in the early days, the business would not be what it is.
Yes.
And I worry that we have too much capital too early and that great businesses are being destroyed by too much capital too early. Do
you fear the
same?
We’re vehemently in agreement. This is, you know, the challenge of our time. I feel there’s like Boyle’s law as applied to capital. So if you raise a million dollar round for your seed company, you’ll spend it and build a company with that million. But if you raise 5,000,000 or 10,000,000, you’ll spend it just the same and get to the same milestones. It’s kind of like the capital expands to fill like the bank account, but used in the same manner. And we’re kind of awash with capital.
So this is a period where we have so much capital, so little hands on assistant in insights. We don’t need the eighties or nineties to come back where venture capitalists would like strangle founders and throw CEOs out of office after, you know, 0.5. But there’s no checks and balances. Balances. And so even the best founders have a lot of trouble when you have so much capital and so little oversight that you kind of drift a little bit. You don’t have the same kind tight discipline that you have if every little penny counts.
Do you think VCs add value? And when you say about oversight and governance, I get you from the fraud perspective. But on the trust side, I’m kind of like, listen, if I invest in you, I trust you. And I I don’t feel like that we need to be kind of the overbearing parent being like governance.
I’d explain it like on a spectrum, and I’d put my two favorite peeps on each side. So I’d put Roelof and Sequoia on, one side of the spectrum, you know, which is more hands on providing services, providing oversight and insights and recruiting and everything else. And then Founders Fund and Peter on the other end of the spectrum, that’s the belief that, look, if you’re an Elon Musk or a Zuck, you just need the money and go at it and you’ll figure it out. You don’t need a outsourced PR team to help you with these things.
You’ll solve these. But given those two extremes, I actually lean more towards the Roelof Sequoia side because I’ve just seen that help and oversight and having that kind of star chamber of great talent cut so many corners of mistakes that would be made.
I agree, but that’s just the brand. When you get Sequoia Invest, there are fantastic people who are like, great. This is a stamp of approval. I want to join a rocket ship. And Sequoia Investing is a leading indicator indicator of that in a lot of talent’s mind. I don’t think it’s the talent teams behind it that make great teams for the companies. It’s incredibly compelling founders who leverage the Sequoia brand.
The lead director, however, does help that founder match with those areas of, I wouldn’t call it weakness, but areas of go to market or growth hacking or engineering or reliability, you know, just help, you know, to shortcuts a lot of these areas that, you know, founders will make a few mistakes before they get right.
I would argue the very, very few great founding teams really truly stick together for a long period of time. I think Stripe and, you know, the Collisons is a great example of one that has done. What I think is most important is like the spikiness of the single best person, which is like when you choose that one person, could be Elon, could be Steve Jobs, could be you name it, that the spikiness is so great. That’s fair. It was interesting. I had Matt Clifford from EF.
Yeah, I know Matt. Yeah, and he said the single most important thing actually is not the combined skills of the founding team. It is the spikiest point of the single best founder. That’s our single biggest lesson from ten years of EF. That is
a very keen observation.
When have you got talent wrong and what did you get wrong with it?
Sometimes talent is so raw that, you know, they run off a cliff or lack maturity and judgment fails. And a founder is kind of always right on the bleeding edge of things going dramatically wrong or dramatically right.
Do you prefer serial entrepreneurs or first time founders? Because I always favor serial entrepreneurs Yeah. Which is ironic given my age. But I’m like, you know, you make so many mistakes the first time around that you just avoid the next time, and you can save so many dollars and so many hours learning the second time. What’s your preference on cereal versus first time?
Well, I should be, you know, statistically focused on cereal, and we back a lot of cereal founders. However, I just have a soft spot for first first time founders. It’s, you know, the teens. It’s the Bill Gates and his teens or Mark Zuckerberg and his teens. It’s the first time around that it’s so spiky or they’re really swinging hard. It’s that age, you know, the army sends the marines in and their 18 year olds because they’re fearless and they just really go for it. But it’s also a period of creativity, you know, where I have to say I’m I’m ageist.
I’m ageist against myself. You know, the Nobel Prize winners have all been, you know, I think within a very constrained age range of creativity and insight and genius or the Beatles, you know, they broke up by the time they were 30 years old. And my goal is to kind of find the Beatles of the the tech world, those great teams and individuals and talents, the Paul McCartneys and John Lennons.
Can I ask a weird one? Why did you do Airbnb? At the time, it was not obvious. You know, it’s famed how many people passed. And it’s a weird idea when you can view it in isolation and put it in context of the time, which is people would let other people stay in their homes, they don’t know them, and that would be a business.
You know, these types of seeds like the seed of Airbnb, the seed of Pinterest at the time, even seed of PayPal, you know, were very non obvious. And the case of Airbnb, you know, we’d go over to, I think the loft was on Natoma that Brian and Joe all lived together and they were building together and we’d go over and hang out with them and, you know, they were just working nonstop. And I mean, I like to think about Airbnb as kind of distributed storage, but not for bits or images or sound or video.
It’s distributed storage for people. You know, you can have a EMC big drive like on prem in your enterprise or you can have things distributed and it’s far more efficient and cost effective. And when you think about Airbnb, they built the kind of perfect massive distributed hotel throughout the entire planet. And what a wonderful business and what they conceived in those days in their loft is, you know, what is here today, a massive scale.
Can I ask how big a check did you write into the seed round?
It was a fairly small check. Now granted we made them an offer. Was I was angel investing and working on Eventbrite and I was angel investing with Keith Rabois and Javed Karim and Javed is the co founder of YouTube. And, you know, we just fell in love with those guys and made them an offer. And Sequoia outdid us and got the lead, but they cut us in nicely because, you know, Brian, Nate, and Joe seemed to like us and Roelof as well.
Can I ask you concentrate capital on the way up? And was it an obvious winner from day one?
We were able to put some amount of capital in the a that Reid Hoffman led, which thank you Reid for making some room there. But then from our perspective, it popped so fast to a billion valuation at that time in, you know, 2011 or ’12. It just seemed like, okay, it’s run away from itself. We never really had the chance to concentrate capital and mostly because it was such an efficient business that just didn’t require the rounds that other businesses like, you know, Facebook seemed to be raising quite a bit and there was a lot of activity and a lot of secondary Airbnb.
There was almost zero secondary.
Bummer.
Bummer. Wow. I’m Yeah. Not sure if It depends which way you want to
do. Do you always hold? Do you ever sell? Like, my biggest mistakes in the last few years, honestly, Kevin, were Be Real, a clubhouse. I could have sold in all of them, and I didn’t. Any big lessons for you on, like, selling on the way up?
Yeah. You know, I just kind of feel that, you know, if you look historically over the decades that if you just sit on all the companies, you know, and most will go to zero, your power law winners will be so massive, they’ll just dwarf everything else. I’m not in the practice of selling, I’m in the practice of finding and building companies and sitting on these things for life.
You mentioned the liquidity word there, and this is the thing that changes when you move from angel to venture fund. You manage other people’s money, often institutions money, they have liquidity needs. And if it’s your angel money, let it ride. You know what? Fine. But if it’s fund money, sometimes you’ll need to show liquidity for the next fund. Sometimes you’ll have pressure from LPs to get liquidity back. There is a change in how one views liquidity sometimes. Not always, but sometimes. I’m just fascinated, Kevin. Why did you move from angel to VC?
I mean, I like a challenge. Sometimes venture people aren’t so nice. You are, Harry. Don’t get me wrong. I liked I I love angel investing, but it’s just time to graduate up to the big leagues, and and that’s kind of the the story here.
Do you think the current venture product is good?
Probably not, but we’ll have to prove to the world that we’re worthy. I love how Sequoia says we’re only as good as our next investment. And, you know, that’s the mindset is you just can’t say, oh, back in Airbnb and Pinterest and Jason loves to talk about his investment in Uber.
I mean, I’m amazed. I didn’t know he did Uber. That’s such a surprise to me, Kevin. Well, really, that’s fascinating. Used to listen to him when I was running and every time, like, you know, I’d be dying running and then I’d hear, you know, when I invested in Uber and I managed to survive to laugh. Very funny. But, you know, I respect him intensely for his duration. Like he taught me one thing that’s very important in media. It’s a simple game. You just have to survive longer than anyone else.
Oh my God, has he ever?
He has done, and it’s just incredible.
The reason I have to like throw him under the bus a little bit with the Uber Uber stuff is he used to call me up at Eventbrite and scream at me like he had a big rivalry with TechCrunch. And when we would ticket things for TechCrunch, he would get really angry and like just call me up and scream at me for doing that.
That’s very funny. So when we think about A* Star today, how big is the fund?
We’re in our second fund. We’re just starting to deploy it. We’re a $300,000,000 fund. Mhmm. 600,000,000 total under management.
Okay. So a $300,000,000 fund, where are we in the stack? We’re pre seed and a?
Pre seed and seed Yeah. And then some b, you know, kind of this seventy, thirty mostly seed. But then when we see a great b, we love getting involved.
Okay. So we’re kind of this interesting barbell approach where we kind of skip the a Yes. But then we’re pre seed seed and then b. Yes. How many pre seed seeds do we
have? Dozens at at this point. We launched about three years ago.
Do you do like market sizing analysis? Do you TAM outcome scenario planning? How do you think about that?
There’s always this discussion and people say, oh, TAM and TAM. This like brute TAM analysis is maybe overdone. I’d focus more on the teams, you know, great teams always find their way to slingshot from the small market to the big market or it takes the small market to get into a big market. So I think it’s more of a qualitative assessment in most cases.
I’ve got to be blunt. I think seed market right now is not a good place to be investing. I find multistage funds have become so aggressive at seed and provide a good product that actually it’s a new enemy or compass in many respects. We have incredible founders like the Coalesons, like Dylan Field, Daniel Gross, who are investing and creating a new class of competition. And then we have all the existing competition from traditional seed funds. Yeah. And pricing is as high as it’s ever been.
Yep.
Am I wrong?
It’s terrible. Nobody should go into seed. I would just everyone should cease all operations and investing in
You joke, but like when five on 25 is the average average entry, which it is for great companies, great founders spinning out, that’s a hard business to be in.
Mhmm. Look, you know, without a doubt, we’re out of that era where, you know, a active investment for certain traditional funds, you know, they had to own at least 30 or they couldn’t be actively involved. You know, like those days are are kind of long gone. Do you have ownership targets? We do target the double digits, but, you know, there’s always the exception. As we all know, like, we would rather be with a smaller ownership with an extraordinary founder than, you know, high ownership with a company that goes nowhere.
That’s interesting. Do you worry about accepting smaller checks where you’re not leads in rounds because then you’ll be known to accept that. We have this internal debate always, like, do we need to lead every round or not? Because if you don’t, your competition will use it against you and say, Kevin’s amazing, you should have him. But he does take smaller checks.
Maybe I’ll put a personal check-in or something like that, but the fund, we’ve got a lead or co lead. Do you think we can go
back to an environment of cooperation? It feels much more sharp elbowed.
It’s much more sharp elbowed, but maybe it’s reverting to the mean because, you know, in times past in eighties, nineties and so on, you had these high ownership percentages, but greater mortality rates and just the extraordinary outcomes that we’ve had over the last couple decades of trillion dollar business now. So the stakes are very, very high, but it does feel like a period of less cooperation and there needs to be a very specific reason why funds would work together.
One kind of aspect, it’s an interesting aspect, is that operators who are also investors. How do you think about whether operating makes you a better or a worse investor? Ben, yeah. Do you think it makes you more empathetic? Because I invest with a lot of amazing founders, and they are hard on founders. Mhmm. Like, much harder than VCs are, because they’re almost kind of in the chair. They’re like, don’t give me that bullshit excuse for missing your revenue numbers. I miss mine too. Like, quit whimpering.
And I’m like, woah, I wouldn’t.
Well, I mean, you know, a lot of venture investors are sociopathic, so that’s part of the explanation. But I kid, sort of. But what would I say about that? Empathetic. You know, look, what we’ve seen, I I wanna say that operators are the the best and there used to be a vibe in the valley that said, oh, you gotta be an operator to be an investor, a venture investor. You’ve had a walk in the shoes. And that’s changed and you see a journalist become one of the greatest venture investor, Michael Moritz slash Harry Stebbings.
Thank you so much. Sorry. Joe, I was And then what else have we seen? People just go Bill Guril come from what was banking? Jeremy Levine from Bessemer was always in venture. He never operated, and he’s been an extraordinary investor over the years.
Talk to me about the B side. Like, that’s an interesting one. How do you think about reserve allocations? Is that reserves on the pre seeds and the seeds?
No. The Bs are separate. These are new investments. So, you know, for example, we let a B about nine months ago and ten months ago in a company called WAP.
How big a check do you write for that then? Not for that necessarily, but like the Bs, you’re leaving a B. 10 to 20. 10 to 20. Do you have a big enough fund? If we say the average then is 15 and you need 10 to 15, you’re 175 to 200 on Bs.
I was told there would be no math on 20 BCs, but you know, perhaps. But I guess it’s a world class problem to have to be constrained on capital. Like I’ve always found that it’s hard to find good places to get capital to work. And when you find it, you just go for it and you’ll find a way to get more capital there. So it just feels like the capital trickles out because you’ve got to be very patient and patient and patient and wait and wait for those great companies.
Are you finding B a better place to be right now? People often talk about like B is dead and C dead.
Oh, god. G is far from I I mean, all the time that, you know, especially eighteen months ago when it was crickets, like, what a great time to be investing in that area. I mean, it’s been great. And and so whenever somebody tells you that an area is dead, make sure you heavily canvas that area and go after it hard because there’s great stuff happening there.
Have you found your mindset change on companies that you like moving from angel to VC? And what I mean by that is like, you know, you don’t always need the massive outcome when you’re an angel, for example, like a billion dollar company, you get in early enough, great, fantastic, awesome. But when you’re a VC, yeah, but actually that might not even return the fund. And sometimes the mindset really changes. Were there any core changes in how what you found attractive in an investment changed between being an angel and a VC?
I think I’ve just been lucky to have always been around people that have extremely high standards aspirations far beyond just returning a fund. And, you know, I just kind of turn off if it’s great if somebody wants to build a nice sized business and have a good cash flow and operate things, but, you know, we’re looking for those extraordinary outcomes.
Do you think you can predict them? When you look at Bessemer’s memos, you know, Procore was a $300,000,000 company. It’s now $1,010,000,000,000. Snap was a $500,000,000 company. You know, Shopify went public at 700, and I think they sold it all at 2. Your biggest winners, you always underestimate the size of. If I told you Airbnb is the size that it is today, you’d be like, never expected that.
Well, you know, certainly I think that the internet space just expanded beyond like our wildest notions. And, you know, so these markets, think about remittance where Xoom went public in 2013 and PayPal acquired it in 2015. But that market expanded so dramatically, you know, since then. It’s that kind of vote or that reaffirmation that, you know, maybe you should stay independent because you can just keep compounding and compounding in the markets.
You know, it’s funny. When you look at venture, there’s there’s sourcing, there’s selecting, there’s servicing, kind of three core pillars, pre selling, that make a great venture investor. If I were to ask you, what are you best at and what are you worst at? Where would you rank the three?
I’m lousy at selling. I can only be kind of sincere in what I offer. I might be a little irked when I see somebody like overselling or BS ing a lot or trying to find ways to kind of win a deal. I don’t think you should win a deal. I think you should earn the right to work with a founder for many, many years. Are they
not the same?
No, they’re very different. I see a kind of slick used car salesman kind of mentality, which is almost like a dupe the founder into signing, you know, versus really what’s best for their business and so on. And, you know, that’s what I maybe offer sincerely. Sourcing is just a factor of, look, as I spend more time in the valley and have a lot of great relationships of founders or other investors or so on, like, you know, the network is very, very broad. Yeah. Selection, what can I say about that?
It’s always a sin of omission. You know, you always think about the ones that you let through or didn’t pursue.
What one did you not pursue that you think of most? And what is your subsequent reflection on that?
Well, I think of Keith when I was stepping down as CEO of Xoom. Keith and Roelof held a lunch for me in San Francisco. And Keith was talking about this YouTube thing. And I was just kind of burnout. It was like a very bittersweet, shitty time to be stepping out of Zoom. And I’m just like, video online? That’s so stupid, you know. Chad was a graphic designer. How would Chad know how to you know, so just completely missed that YouTube thing, for example. What was the reflection on that?
The reflection is very clearly your mindset. It’s always be positive and open minded. Let’s say you’re having the worst day of your life and you meet a founder, like you still have to believe and you still have to have that view and really, really listen, because that mindset, if it’s off, this little casual interaction becomes something really crazy.
It’s the thing I love most about this business, actually, which is unlike any other job, I think in the world, one single meeting can change the life of you, your family for many generations. I say to the whole team, you can never be off with a founder. I think people forget that. Are you honest with feedback to founders?
No, totally dishonest.
It sucks. But like, seriously, like, sometimes it is the founder that is the problem, and you’re like, honestly, I just don’t believe in you. I don’t think it’s right to send an email back saying, I don’t believe in you. I’m probably wrong. Who am I to say that you’re not good enough? But
there’s always good things to say to that. You could say like, why don’t you look for some complimentary expertise? Maybe you should bring on board a co founder that can do this, this, and this, or But once you start explaining too much, you know, it just goes back and forth and back and forth, then time is short. So what do you do? I’ve I’ve just unfortunately have to be very curt. You know, like I always remember seeing Michael Moritz give a talk about Google in the early two thousands, and there were all these founders there.
And he puts his phone up to his face and pretends to talk and then like walks out of the building, you know, and so nobody would like bother him. And like that’s splitting the ocean to get, you know,
like, away from that. How do you feel about exploding term sheets? I see them quite a lot nowadays.
Well, little known secret is Keith, Javed, and I gave an exploding term sheet to Airbnb, and Paul Graham said no bueno and teed off on us. It worked out. We got cut into that round, but you don’t forget things like that. You just do not forget that. I don’t think I’ve ever told that story.
Were you
nervous when he said no, bueno? I think he posted on it. He didn’t call us out, you know, he chided us privately, but he didn’t call us out publicly. He called out the practice of doing it. You know, you really
kind of understand as well. Exploding term sheets have a horrible signaling name, like they But just actually, if someone’s gonna literally go around and say, hey, Hartz has given it to me at 25. Does anyone want to do it at thirty? Obviously, that’s not great. There is a reason for it.
There is a reason for it, but you would hope that you found a partner that’s not gonna shop it. And maybe if they’re gonna shop it, then it maybe wasn’t meant to be. But they’re always
gonna shop it. They’re running a process. And you could argue that’s their job to run a process to get the highest price. Yeah. But, like, that’s my point. I don’t want to be in a process.
Yeah. Well, the issue is is that you put a term sheet out and it, like, explodes on Friday at 5PM, but does that mean
back at 05:15.
Did I miss the But does that mean that you at 05:15, you no longer want to invest? No. Like, the investor will always be there. I think it’s fair for founders to go out and assess the market and more importantly, the partner. And so we just have to unentangle ourselves. You can there’s bad behavior on both sides. There’s like the obnoxious shopping, just give us the term sheet and I promise we’re going to get this done. I just need a couple days. And then, you know, you find out that they went and shopped it like crazy.
But to the flip side, a fund can lock a founder down. That founder just hasn’t done their work or hasn’t been able to do the work to speak to other investors and find out how others could be of help. And so How do you lock founders down, Kevin?
This is something that, again, the show is very successful now because I think I’m very open with my struggles. I struggle in locking founders
Well, we can’t lock them down kind of like like Silence of the Lambs. The handcuffs. Yeah. Sounds like Hannibal Lecter. Those pink fluffy handcuffs don’t work. Yes. Like it has to be a very voluntary you know, like we we just have to use honey, not vinegar, or what’s a good British I bet there’s a very trite Oh, there’s a sun packed
peanut butter. Quickly do you know when a deal’s working and when it’s not working?
Oh, there’s some that you know is gonna be a struggle, and then others that wander in the woods for, you know, that take a long, long, long, long time and and people almost forget about them. Or you got investors telling his founders to return the money and they stick with it. The most important thing is just patience. Certainly, you want them to maintain a sense of urgency, but you just have to see patience because you just see time and time again, time as the thing to solve the problems and to get into orbit.
And then there’s the ones that just work from day one. What do you think you’re talking about three value drivers? Airbnb, Pinterest, Bitcoin. I was in Wyoming drinking whiskey with in October 2011, and he started talking about this Bitcoin stuff. Uber was Series Bitcoin then? A good amount. Investors never give you, like, exact answers, you know, and you want exact numbers. But investors always like skirt around it. I mean, you know, I always have a soft spot. It was a poor it was like a relatively mediocre return because of all the capital.
But PayPal going public was like one of my first investments. From a multiple perspective, what was that? Not that not that great. Have to go and look at it twenty ish or so, you know, but you would think. If I’d held it longer, because what happened is eBay acquired it, and then eBay had a run-in the early two thousands.
What’s your biggest zero and what did you learn from that?
Biggest zero. It was like a kind of turned out to be a kind of classic Sequoia investment that I did with Roelof was in a company called TokBox, t o k b o x. It was early live streaming. No. Oh, yes. He was there. Yeah. He was there. Yeah. And which he went on to go Kevin, to
I am a student of this business. My god. Yeah. Yeah.
Wow. I actually recruited him for that through cause I knew Jack Abraham who started Milo. Yeah. That’s so funny. Wow. It just blew my mind that you came up with that. And I’m
like the most useless encyclopedic knowledge of this business.
No. That’s far from useless. Like, that’s incredibly important to know the lineage of these things.
History is very important. Yes. Okay. So TokBox.
So TokBox was, you know, live video before kind of FaceTime and all this sort of stuff. And Roelof got involved and led the Series A. Keith Rabois and I had seeded it, very actively involved in it. You know, just kind of everything that could go wrong went wrong, scaling issues, market fit. Tony and we even had Tony Bez join who was, you know, he had joined the board of YouTube like after Roelof had and and so we were kind of like getting that group back together and it just wouldn’t take.
Now the interesting thing is that, you know, Sequoia found and, you know, helped it park with, I think it was Spanish Telecom acquired it for like 70,000,000. So we got like a small return, like a two x or something, but just not worth the time and the pain and the broken glass of of that. And then it’s, you know, the hard part is is that, you know, it was at that time when Sean Parker was doing something with video. What was the name of that? Oh, wow.
And it was I know exactly. The one where people would put their privates. Plato. It was a different airtime.
Plato is another one of his.
Yeah. Yeah. Plato. But airtime in what was the one where people would live video and it was this Russian kid and it was it just kinda blew up. It was like the earliest live video streaming. What? Trivage Q? Not that was actually I was at Founders Fund in Siamese. That was big. That was awesome. That was a remember we tragic used to leave work Yes. In The UK to be there for Trivage Q. Yeah. Somebody should bring that back. With you. I think I think there was it was a tragic ending.
You know?
I I know. I think there’s a real incubator business to be done in looking at historic Yes. Successes Yes. That went wrong for reasons that could be mitigated.
Completely.
Yeah.
Completely,
completely. Do wanna cofound that HQ? Yeah. I’ll put $10,000,000 in a few of Yeah. Let’s do it. I’ll match yours. Yeah. It’s not a bad idea. Okay. We’ve got that. Because you actually have product market fit around ideas. Mhmm. Like, the idea of time dense concentrated events is super cool.
I mean, if you brought HQ Trivia back, it would also be this like nostalgic vibe. But
I think the other thing that people forget is like just how hard it is to get attention today. I always say this to the team, but I say the only thing more competitive than the computer attention economy. And actually people don’t think enough about how do I get like macro headlines. And actually if you bring back HQ Trivia Mhmm. And you and I would have put $10,000,000 in each to bring back an incubator that brought back retro hits
Mhmm.
You would get in some of the biggest publications. You would get to a big number of users pretty quickly.
What else would we bring back? I wanna bring back Hot or Not. Listen,
think Be Real was a fantastic product Be Real. There you go. And so there is quite a lot that you could actually bring back very efficiently. What would you not bring back? Oh, that’s a really good question. You know another one that I would bring back? It was a massive cash cow in London, Madbid. Do you remember Madbid? No. You would buy a laptop for about £10. Oh my God. You’re like, how do I buy a MacBook Air for £10? Yeah. To bid, you have to put down a pound.
And so to basically bid a 100 times, you have put down a £100. And so for a MacBook Air that sells for £10, it’s actually what is that? $10,000. So for a $2,000 laptop, they bid five times that in bids. Amazing. The gamified version of like eBay in a really cool way.
I’d bring back Friendster. Oh, why? No, I wouldn’t. It would be too difficult now.
It’d be a freaking nightmare. Yeah. No, I told you, think about
market
timing when you invest.
Yeah, of course. Human nature is to look at things that are working now and think like, oh, let’s build something. You know, you see all of a sudden everything kind of pop up being memetically duplicative of something that’s doing really, really well. And the response is no, look three, five, seven years ahead, not now. That is a big issue is, you know, is not looking far enough ahead.
Kevin, is it wrong to ask your money back as an investor?
It kind of depends on the the level. Guess, you know, I’m again focused on more of the big outcomes and things that aren’t gonna work aren’t gonna work. It’s the power law winners that are gonna really drive the the returns.
Is there a power law winner that you thought would be a power law winner that didn’t turn into a power law winner?
You know, I think the jury’s still out. There’s still a lot of value there in OpenSea. Was just the investor in OpenSea, and during the boom of 2122, it was valued at 13,500,000,000.
Why would you not sell some then, given doing the seed there, Kevin?
Yeah. I, you know, often think a lot about that. And, you know, my mindset was honestly, you know, when you see that fast level of growth, you’re thinking about what the GMV is going to be, you know, over the coming quarters. And you don’t think of it as dropping dramatically. You think of it as continuing to head up at a rapid pace.
But it does. I mean, I I mean this nicely, I’ve been pushing back. It doesn’t matter, dude. Like, you get in at seed, that is an astronomical return. You should at least take some off the table. No? Would you have taken some off the table if you’ve done it with the fund at seed?
Well, you know, I I guess I should say yes, because it only behooves me to answer yes. But and there is, you know, that round, that $13,000,000,000 round with Coatue. Yeah. Was extremely tight. Like, they were they wanted more stock. And so the avail the secondary was there and available. So there was a chance to sell. But you would say the same thing about the $10,000,000,000 round that Facebook did with Microsoft. Should people have sold that?
No. But he did the seed, honestly. Mhmm. Just pause. Of course, you shouldn’t have done from a pure quantitative assessment. But if you did the seed and you had the chance to sell 25% of your holding Mhmm. And return huge number, 300, 400 x, and ride 75%. I don’t think many people regret that much selling the 25%.
Yeah. I think it depends on what your goals and outcomes are. You know, there’s something to letting it ride. Like in the case of Facebook, which is now worth what? 7 or 800?
Yeah.
Harry, you’re 26. You know, you should be just compounding. Like, your your winners just like keep them growing and growing. Do you
wish you’d taken more risk when you were younger, Kevin? It’s very kind of you to mention a compounding nature and my age. Yeah. I mean, What could you not take risk on that you wish you had?
Yeah. I mean, it’s always around an investment or working with a team. I mean, you know, I talked to Peter at the time he was putting the team together for PayPal, and I had invested in PayPal, I’m like, why would I join PayPal? You know, like, I’m already an investor in it. I already have shares. You know, but the answer is, you know, go all in. Then when the day that the acquisition of PayPal by eBay was announced, Peter had resigned and I met him up at the Sundeck restaurant up on Sand Hill Road.
And he said, you know, Kevin, I’m working on this business and, you know, we’re taking kind of the fraud algorithms from PayPal that kind of find these associations between disparate nodes and and we’re going to use this to to catch terrorists. And, you know, do you wanna get involved? And I I said, Peter, you’re a libertarian. Why would you want something so, like, invasive of one’s privacy? And that was the wrong response. Shouldn’t have done that. I should have joined Palantir. Can anyone do a deal?
Can anyone do a deal? If somebody says with absolute conviction, I wanna do this and I’ll put my life on the line for this, you know, then absolutely.
I think it’s really important. I got asked by an LP this morning talking about your voting structure. And I said, I think voting structure is complete bullshit. Seriously? Love Well, don’t tell your LPs that. Oh, no, I do, because I always present them the outcome scenario, which is, you know, if you’re actually strategic, you always vote a six out of 10. Because if it’s Uber, I was a yes, and if it’s a terrible company, was a weak yes. It was basically a five. Like, it was weak.
So it brings politics to a new level into a partnership that just doesn’t need to be there. If I’ve hired you as my partner, and I’ve given you equal or really meaningful carry, and I dedicate years of my life to owning with you, if you really want to do a deal, why the fuck would I not let you? Yeah.
Yeah. I admire Founders Fund for how individually driven it is around conviction of a single partner.
Did you have any big lessons from being there? Oh, endless. What are the biggest that you took with you?
You know, so many. I think it’s such a great form of venture that they practice. It is very conviction driven. It is the emanation of the power law. It was Peter and Brian Singer and Napoleon that took what did they take? I think they sold Spotify at the $8,000,000,000 price, pissed off Daniel Ek, and rolled it all into Airbnb at the 2,500,000,000. And so they’d doubly, like, went into things. And so that kind of going all in is very important. When when you look back at a fund, you just don’t want something that’s just kind of like blah, you know, a little bit of mushy of everything and doesn’t have its like big power law winners.
Like you just boil funds down to the SpaceX fund and the Facebook fund and the Airbnb fund and the, you know, and so on and so on.
I remember Brian Sigham and telling me the enemy of great venture returns is capital concentration limits on a per company basis. That’s so Brian. Yeah. You should be 30% in on your big winner. We were on Airbnb. We were on Bitcoin or whatever that was. Always remember that.
I did push them at their AGM around the Airbnb deal, and I so I give myself a little credit. Because I’m a venture capitalist, you’re supposed to give yourself credit for all these things. It probably wasn’t. You basically
founded Facebook. Right? Yeah. I found Facebook, you know, facing the
crowd. That was mine. But I remember really saying, like, you guys need to look at this company. But all that is patting on on the back. Brian’s so interesting because he would just when when I was, like, ready to go with the company, he’d just say, Kevin, you really, really, really believe this will be the one, you know, he just like shakes you, you know. And it used to, you know, agitate me a tiny bit, but I appreciate that now.
Do you ever tell founders when you don’t believe anymore? When things are not going well, do you just quiet quit?
A Rulofism is when things are going really poorly, that’s when you’re supportive and nurturing and not hammering, believe it or not. When things are going great, then you dig in and like hit them hard. That was a Roelofism that’s been so key. It’s incredibly helpful.
Really?
I know for a fact.
So you think when it’s not going well, like, oh, it’s okay and you’re supportive and that’s nice. Mhmm. It’s better than actually, hey, we need to fucking turn this around. We can do this, and that you’re much more tough. Sometimes tough love is needed.
Tough love is needed when it’s doing extraordinarily well. When things are going terribly wrong and there are the butterflies and stomach, you know, is like seized up and teammates are quitting and somebody’s hacked the site or whatever, you know, all these things, like really being a solid productive voice of calmness and support is extraordinarily helpful.
I think it’s about like understanding what the person needs in the moment. Some people do need that, absolutely, and it’s unbelievable. But some people don’t resonate with that. And actually, they need like for me, when it’s really hard, I’ve had some shit times, Kevin, it was my mom giving me a kick up the ass and saying, you gotta wake up tomorrow and fucking stop moaning. Get on with this. It’s so individual let Kind of a weird one, Kevin, but what are your biggest lessons on what it means to be a great father and what great parenting is today?
I have to be careful not to put too much pressure on my girls to, you know, in this in this age of so much intensity in The Bay Area and Oh, school and absolutely. My 16 year old, we found she had a very severe eating disorder at end of December. We caught it luckily because it was fairly early on because of her annual exam. And so we saw the significant drop in weight. She’s a dancer. She has something called SIBO, stomach intestinal issues that had been another driver of having your limit or food.
She was straight a straight a student. She was under a lot of pressure dancing twenty plus hours a week and she just stopped eating and she’s ended up in the hospital now three times. And, you know, it’s this multifactorial illness that is so prevalent for this times that we’re not aware of that comes from social media and dance and all these other pressures and it’s culminated in this terrible illness. So I’m very cognizant of the pressures we put on our kids.
I didn’t talk about this too much, but I was bulimic when I was young. It’s the most hard, I think, addiction problem to deal Hard thing with food, you can’t just stop eating. You can’t stop your interaction with food.
I understand in bulimia there is also some gratification post or some endorphins or A
100%.
Yeah. And the recivitism for eating disorders is off the charts. So like everything else, it seems like if you have cancer, diabetes, you know, there’s so many different treatments and scientifically focused treatments, but in eating disorders, there’s nothing. And so these kids just go over and over and back in the circular motion. And I’m like in shock of how barbaric the treatments are for the they’re just non existent. There’s something called family based therapy, which is you sit down, eat with your child, meal after meal after meal, and it’s agonizing because it’s it’s like having a phobia and having to you know, if you’re scared of spiders, to be in front of spiders all day.
The hardest thing is they have to be the ones to initiate the change.
Yes.
Was it your daughter that did that?
She she we don’t know if she’s still ready. She has to you’re exactly right. It’s like there is a the thrill or the notion of being thin and being a certain way and not wanting, you know, to change. And that’s how we’ve ended up in the hospital three times. And we hope now she’s making that right move and that she wants to get better and understands. She had to withdraw from school. She is finishing her semester online through online school, which is a godsend. It’s incredible.
It’s like the Oxford tutorial method online. But she is yeah. You you do have to want it, but I could never imagine like an American kid. Like my sophomore year in high school was great years. Like, so much fun, close friendships. And I don’t never knew anyone even withdrawing from our high school before for any kind of medical. And then for her for her to go through this is just agonizing.
I remember with my mother. My mother’s an alcoholic too. And it was the hardest thing because for a good few years, I just had to watch the person I love more than anything suffer, and there’s nothing that you can do.
That
is really hard.
Yeah. I think there are are many more treatments that should be applied, you know, that should be more prevalent. I don’t know whether it’s TMS, if you’ve heard of transmigral stimulation, if I said that correctly. Transmagnetic stimulation, different ways to kind of provoke the area of the brain and correct whether it’s an eating disorder or alcoholism or addiction pathways
or
so on.
But before we do a quick fight, two of my biggest concerns is actually like eating disorders, young eating disorders in men is one that’s really not talked about as well. Especially for boys, it’s even more of a and then just like depression and loneliness. Mhmm. The hard thing is, Kevin, like, job is to invest in amazing products that hopefully make the world better, have great impact, I think. I can’t find businesses in that. Calm or Headspace of the world, makes mental wellness, health, they’re not great businesses.
Is this our job? The challenge of this era, of our era, is neurological issues. Like Peter always tends to be three steps ahead of us on all of this. He’s been after this area for a while. But, know, as we beat back cancers, as we beat back heart diseases, disease which unequivocally has happened, Alzheimer’s, Lewy body dementia, you know, all these mental illnesses, bipolar, like these are are the prominent illnesses of our time and there need to be therapeutics developed for it. Yeah. This should be just as I think it was Richard Nixon in, like, the seventies said, let’s go after cancer.
You know, we need to to go after these neurological disorders that are becoming so prevalent in our society.
I totally agree. I could talk to you all day, Kevin. I love the way I haven’t really looked at the schedule. I spent hours supposedly doing it. But okay. So I wanna do a quick fire. So I say a statement. You give me your immediate thoughts. Does that sound okay? Yes. So what have you changed your mind on most in the last twelve months?
The rapid ascension of the defense segment, like how it’s gone from zero to 60. You know, certainly Palantir, then Anduril, but now, you know, how the world has dramatically changed and how unprepared The United States is.
What VC do you most respect and learn from?
You know who I spent some time with when they were getting their first fund going was a group called VY Capital. Yeah. Alexander Thomas. Yeah. John Herring and Alexander Thomas. Their style and pace and patience and wisdom is is extraordinary.
I I completely agree with you, and actually very much aligned to your thinking on upside maximization. Truly focus on the mega outcomes. So I totally agree with
I’m in a lot of funds, and holy Moses, that fund one is en fuego.
What’s the biggest advice to someone entering angel investing, Kevin?
Just rope off some money you wanna lose because you gotta look at you’ve gotta, like, take a lot of swings at bat. So I think, you know, Renaud has, like, a corollary to this that you’ve got to, like, burn through, like, 40,000,000 adventure before you really know what you’re doing. And, you know, angel is is you just gotta start learning and and pattern recognizing. You do that by taking risk.
I totally agree with you. I’d also say write the same size check every deal. Everyone thinks, oh, okay. Different conviction levels. I’ll write a 100 k check and I’ll write a 25. You’re not that smart at pre seed. Just write 50 k checks every time. Mhmm. Super important. Which VC would you most like to swap portfolios with?
Y Combinator continues to have this, like, ideal venture model in every class that comes around. Like, the whole valley says, oh, now they’ve really jumped the shark. They’re no good anymore. But like year after year after year, keep producing these incredible companies with With these
Gary coming back as well. Passed right again. So I totally agree with you there. Why is that I
passed on Gary when he was working on Posterous.
It wasn’t a great outcome.
No. I just thought I’d throw that out there. It’s a weird flex. Well, he might have earned billions in That is absolutely amazing. And he’s helping San Francisco, though. He’s doing a Unbelievably. I mean, this
guy is incredible. Yeah. He’s
having his day.
Yeah. Yeah. No. Absolutely. Tell me, why is now a good time to be a founder?
We are blessed with the capital gods. Like, this is an incredible period. Like, don’t get me wrong, and I haven’t I’m gonna say, like, I have strong conviction that we’re in the early years of the biggest bubble. And I say bubble because we’re in this world of capitalism. The signs that I see, NVIDIA becoming the most valuable company on the planet, is just the precursor towards the bubble of all bubbles, the AI bubble. There’s going be so much made and created, and of course, there’s going to be so much foolishness to come.
But then you also have these compounding, like, add on bubbles of crypto and fintech and, you know, this worldwide economy and tech economy that’s emerging, new areas of clean energy. We just got involved in an industrial biotech company called General Biological. So there’s so many different platforms to build off. I always look for platforms to to invest like the why now question is. In the beginning, the transformers came and Sam created ChatGPT and there was Plentiful, the fastest growing company came out of that. And that tells you that the platform is here and build apps on top, and we’re gonna have so many different opportunities around this.
And
So will venture numbers be better or worse moving forwards? More capital, but more platforms, more breakthrough technologies.
Well, there’ll much better than that 2122 catastrophe that that we just saw of, oh my god, that that was horrible. So, I want I I wanna say venture returns will absolutely be better because if you index against that, that’s that’s not too hard to compete against.
Did you fuck up in ’21 or ’22? Oh, yeah.
Who didn’t?
Final one for you, Kevin. What question are you now you’ve had done many interviews over the years. You’ve been asked so many questions by so many different brilliant people. What question are you never asked that you should be asked?
Perhaps it would be just that question that everyone always answers insincerely about what their weakness is, but like, what is your mental illness? Is it depression, anxiety, bipolar, addiction? To be honest about it.
Kevin, listen, dude, I so appreciate you. You’ve always been so kind to me and so supportive when I was very, very young, and I just really appreciate you. So thank you for doing this. You’re still
very, very young.
Less young than I was,
You’re younger than Harry Stiles. Right? That’s crazy.
I mean, was just so much fun to do. I have to say, so much of that show got edited out because it was maybe a little bit less PG rated and utterly hilarious. But I wish we had a bloopers edition where you could see behind the scenes for that. But sadly, not quite yet. I wanna say a huge thank you again to Kevin for being such an amazing guest, and that was so much fun to do. But before we leave you today,
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