The Exchanges

Q That actually brings me to an element in your book where you say that companies are bought and not sold. On the show previously, we've had Josh Felser at Freestyle who said that they're sold and not I'm intrigued. How did you come to this conclusion, and what's the thesis behind that thinking?

A Yeah, the truth is, if you go out and you try to sell your company, people are going to look at it and go, what do you do? Who are you? Why would we need this? And it's, it's not a priority for them. I've seen it over and over again, where companies say, hey, we're running out of money, we're going to run a sale process, and it's never gone well. Now, if a All of the people with huge chip stacks start looking at it saying that is going to be a rocket ship. It has escape velocity. It's going to get to orbit. And once it's in orbit, it is very hard to take a company that's in orbit and get them to crash back down to earth. In fact, it will take decades. So even AOL and Yahoo, which went through decades of mismanagement each, they are still alive and they still exist and they still have a combined billion users, right? That's Yahoo and AOL. The laughing stocks, the most mismanaged companies still have a billion users combined, and they still produce billions of dollars of revenue. So that shows you how hard it is to displace something once it's in orbit. So what happens is if something like YouTube stumbles, like where they had their big legal case, a company like Google comes along and says, yeah, we'll buy it from you. You put five hundred million in escrow and let's go. Or Instagram, you know, they raised at a five hundred million dollar valuation. A couple of weeks later, Zuck…

AI assessment note: “if you go out and you try to sell your company, people are going to look”

Q Let's finish today with what would you most like to see change in startups and VC?

A Great question. I think, I mean, this is one of the most efficient, insanely great industries in the world. I would like to see on the, on the VC side, I would like to see more people participating in the speculative rounds. So a lot of VCs have given up on doing early stage investing, and a lot of them just look to people like me or YC or other people, and they just outsource the whole goddamn thing. I'd like to see some of those people dip down a little bit and maybe play some 250 K, 500 K bets, but I don't think it's likely to happen, but that's why I have an opportunity, and people who read the book to become angels have an opportunity. On the founder side, I would like to see more founders take the work seriously, stop going to Web Summit or Summit at Sea or TEDx or other bullshit, And start adding more skills and get more focused on their customers and revenue. There is a major distraction culture in founder land where everybody thinks they have to have a podcast, have a conference, go to conferences, and there's too much networking going on and not enough skills development and client development. So I think we have a massive amount of tourists right now, and I think people want to have the rewards that they see great entrepreneurs have. Before they're profitable as a company, I tell all my founders, until you are profitable, until you're lording over the investors becau…

AI assessment note: “I would like to see on the, on the VC side... On the founder side”

Q Do you blame founders for selling out early?

A No, of course not. You know, listen, if you have zero dollars in the bank, I sold Weblogs Inc. for thirty million dollars in Blogsmith. And I had negative in the bank, and I had one partner, and then one investor in, um, you know, Mark Cuban, and, you know, we could have held on, and I think Gawker, 12 years after we sold, sold for a hundred and twenty million. They gave forty million of it to Hulk Hogan. They gave forty million of it to their investors, and I think they netted out maybe 30 or forty million for the founders. In other words, they sold for almost the same as us. They probably would have sold for double or triple what we sold for, but I would have had to spend 12 more years of my life on it. So there's an opportunity cost there. And if you can bank a quick ten million dollars or five million dollars, I'm not sure if you are a lord. So unless you're one of those lucky sperm club members, of course, you have to bank a win. For the love of God, if you have the ability to take down five or ten million dollars, you got to do it. You got to do it for your family. Now, one great thing that's occurred in the last five years or so is the ability for VCs to give founders the ability to sell some shares and And to not have this panic that we all had 10 years ago. So 10 years ago, Flickr got sold for twenty million bucks, Delicious for 15 or twenty million dollars, and Dig, a…

AI assessment note: “No, of course not. You know, listen, if you have zero dollars”

Q Let's finish today with what would you most like to see change in startups and VC?

A Great question. I think, I mean, this is one of the most efficient, insanely great industries in the world. I would like to see on the, on the VC side, I would like to see more people participating in the speculative rounds. So a lot of VCs have given up on doing early stage investing, and a lot of them just look to people like me or YC or other people, and they just outsource the whole goddamn thing. I'd like to see some of those people dip down a little bit and maybe play some 250 K, 500 K bets, but I don't think it's likely to happen, but that's why I have an opportunity, and people who read the book to become angels have an opportunity. On the founder side, I would like to see more founders take the work seriously, stop going to Web Summit or Summit at Sea or TEDx or other bullshit, And start adding more skills and get more focused on their customers and revenue. There is a major distraction culture in founder land where everybody thinks they have to have a podcast, have a conference, go to conferences, and there's too much networking going on and not enough skills development and client development. So I think we have a massive amount of tourists right now, and I think people want to have the rewards that they see great entrepreneurs have. Before they're profitable as a company, I tell all my founders, until you are profitable, until you're lording over the investors becau…

AI assessment note: “I would like to see on the, on the VC side... On the founder side”

Q Would you say that's the next sector to be disrupted? Or to really emerge?

A Yeah, drones, three-D printing, and virtual reality, um, and machine learning, uh, and the on-demand economy, these, like, sort of trends are all starting to merge and, and sort of build off each other, and really build off the back of smartphones, whether it's the sensors in the smartphones, or the broadband network, or GPS, all that stuff is starting to converge, so, you know, you'll have companies that couldn't exist if we didn't have Samsung and Apple, uh, Battling it out, making better and better, and Foxconn, making better and better sensors and chips, so I am super bullish, um, on drones. I think three-D printers are starting to really help people who are making other hardware, so it's sort of a picks and shovels kind of thing, and then, you know, I, I really have never believed in virtual reality until this latest cohort of companies. Sixth Sense is a really interesting company that's Does the motion tracking where they, they put like things on your head or your wrist or your ankles, and you really know where your body is in three D space and, you know, obviously Oculus. So I think that stuff is really going to work for video games and adult entertainment, and it could work for education. So, you know, I think it's going to be kind of mind blowing that you're going to be able to, like literally we could put out the training course for how to do hearts or open heart surg…

AI assessment note: “Yeah, drones, three-D printing, and virtual reality, um, and machine learning”

Q I'm intrigued. You spoke about the macro there, the wealthy becoming absurdly wealthy. How do you view Silicon Valley now? You're obviously in the midst of it. How do you view the macro environment now and where we're at in the cycles and your perception around wider, wider startups and the funding environment?

A Well, we're about to hit a decade-long bull market. You know, we had the financial crisis in the Was caused by bankers over hyping tech, obviously. So I, I don't think that tech industry is at fault in any way. I think the people who are paying high valuations for companies are, you know, if you look at something like Blue Apron, which is a fine company with a very innovative product, they, they had to lower their price for their IPM. They were going to go out in a 15 to 18 dollar range, and maybe they're going out at 10 or 11 dollars. This is healthy. It's healthy that the market says, hey, we know you want to raise at a high Valuation. But we don't want to buy your stock at that high valuation. And the people who bought, I think, Fidelity, I read, bought their shares at 13 dollars. So Fidelity will be two dollars underwater when the company goes public, or three dollars underwater, perhaps, according to what I've read. Well, that seems like a bummer, but Fidelity knows what they're doing. You know, and Fidelity overpaid a little bit, you know, in some cases. That's okay, because they'll overpay some cases, and they'll underpay for Google, or Amazon, or Facebook, or Netflix, or Uber, or Airbnb. Or in many cases. So while people are saying, oh my God, it's so hyped, and valuations are so high, the people who are setting those valuations are the most sophisticated financial peop…

AI assessment note: “Well, we're about to hit a decade-long bull market.”

Q So I'd love to start by hearing about Uber. I mean, we obviously hear a lot about your investment in Uber. Incredible. And how did that come about, and how excited are you for the future of Uber?

A Well, I'm obviously delighted with, you know, how the company's turned out, but it's not unexpected that this would become an important company, because the founder, Travis, um, who I've known for 15 years, um, when I was a journalist, I interviewed him when he was doing Scour, which was a peer-to-peer company, sort of like Napster, but it did every file type, um, and I remember when he was very young, maybe 23, 24, I was interviewing him, and I was a couple years older than him, Running a magazine, Digital Coast Reporter and Silicon Valley Reporter, and we had a hundred VIPs in a room at Casa Del Mar in Santa Monica, and he had just been sued for a quarter of a trillion dollars by the movie companies. Yeah, and, um, he was visibly shaken from this, um.

AI assessment note: “because the founder, Travis, um, who I've known for 15 years”

Q I had breakfast this morning, actually, with a very successful individual, Remain Unnamed, and he said the tech, kind of, elite today are the aristocracy of our time, and the aristocracy are always taken down by the feudal society, the well-known ones first. Do you agree with this kind of pessimistic view about the downtaking of an aristocracy society?

A So, yes and no. The part that I would disagree with is, and you can correct me if I'm wrong, because I'm, I'm from the spin-out nation, America, not the original, the UK. The aristocracy you're born into, and with the exception of Tim Draper's kids, and Tim Draper himself, and Ron Conway's kids, Nobody has been born into venture capital, and even in those cases, it turns out the hardest working people I've met in venture, or some of the hardest working people, are Ron Conway's kids and Tim Draper's kids. These individuals who were born into it are incredible hustlers running Draper University and angel investing, and, you know, they're just known for being hardworking, so I disagree with the aristocracy part, but I will say that we are Because of the polarization of wealth in society, and the rigged system in America that makes the wealthy ultra-wealthy, and the ultra-wealthy absurdly wealthy, and the poor and the middle class are getting ground down, and they're having a hard time even holding on to being middle class, so they're moving from the upper middle class to the lower middle class, from the middle of the middle class to the upper parts of the poor folks in the country. That's Unfair, and that system is broken, and that needs to be fixed, and it's part of the reason I wrote the book was, I don't think the middle class, and certainly not folks who are poor in our countr…

AI assessment note: “So, yes and no. The part that I would disagree with is”

Q And where do you sit on Bitcoin? Obviously, it wasn't one of the ones you suggested there as your decision.

A Yeah, no, I mean, I wrote about it before anybody, and I should have bought it at a dollar or 50 cents, whatever it was trading when I wrote my piece, you know, the world's most dangerous currency, um, and so that was a miss on my part, stupid one. Um, you know, obviously, the blockchain and some of that stuff is very interesting. I think Bitcoin has an equal chance of going to zero as it does to a thousand dollars again. I think it could be, like, the first person up the hill who fails. You know, it could be the Mosaic browser, or it could be the Netscape browser, where, like, you know, the web is super important, and the Netscape browser, you know, and Mosaic browser, and what Mark Andreessen did there was super important, but it doesn't exist anymore. I mean, it exists as Mozilla, maybe, but, you know, sometimes the first person who, you know, goes up the hill gets all the arrows and dies, um, and so it might be that stellar, you know, um, is, you know, the next one up the hill, and they make it work because they're a non-profit. I don't know. Um, but, you know, I have to say, it's kind of embarrassing for all these VCs and founders that they, they can't make this product mainstream or find a decent application for it other than speculation or money transfer across borders. Um, they really need, these founders kind of suck. I mean, really the founders in the Bitcoin space ar…

AI assessment note: “I think Bitcoin has an equal chance of going to zero as it does to”

Q Who does your biggest competition then in the podcasting sphere?

A Um, well, here's the thing. I, I I'm definitely the number one startup podcast. Leo Laporte's definitely the number one tech podcast. Um, and then, you know, Kevin Pollack, Adam Kroll are the, you know, the best in the, in the media one. Um, so I, I don't know that I'm up against anybody really, um, in the podcasting space. I think I'm probably, you know, at the top of my specific game, but there's really not that many people I'm competing against. Um, and you really, if you just, um, The person who doesn't quit actually becomes the best. So, you know, there's a, in podcasting, it's really just about not giving up. Um, and so the people who keep going, you know, if they just get literally one percent better every episode, if you do 500 episodes, you're going to be pretty fucking good after a while, right?

AI assessment note: “I don't know that I'm up against anybody really”

Q Have a gift for reading people, and knowing who the good spot, that eye of the tiger, I remember you said it, I think in a product hunt podcast, you called it the eye of the tiger in the entrepreneur's eyes. How do you spot that? Is it their passion?

A You know what? It's, it's very, it's very weird. I could try to explain it to you, but I would seem, like, really pretentious. Um, but the truth is, you know, when I'm talking to somebody, I almost feel like I see past their eyeballs, and I see into their brain and their soul, and I see if they actually give a shit. And I can tell you, you know, seven of 10 times they meet with a founder, I can tell they don't really give a shit about what they're doing. They're just like, they're doing it because they want to be a founder, they're doing it for some reason, and But this isn't their passion. This isn't the idea that's gonna do it for them. But sometimes, you know, maybe 30% of the time when I'm talking to somebody, I can see, like, holy cow, this person really cares about this. Ok, so now I've, I can very easily knock out seven of 10 people, you know, when I'm meeting with them. And I just, in my mind, I say, like, listen, this is not, this person might be successful, but generally speaking, people who are not passionate and really believe in their idea And really want to do it. Um, you know, like it's not worth me investing in them because it's probably a one in a 500 chance that they're going to be successful. Now that last 30%, it's probably, you know, it's still a 10 or 20% chance that they're going to get me a great return.

AI assessment note: “I see into their brain and their soul, and I see if they actually give a shit”

Q And how do you measure your success then? Is it the exits? Is it your value?

A That is really the key question, and I think you nailed it there, Harry, which is, what scorecard are you playing by? Now, there's going to be the scorecard of returns, and that's important, so I don't know if I could ever catch up to Chris, um, but I know that in terms of how helpful I am, I know that I'm as helpful as Chris, right? In fact, some people might argue that I'm more engaged than Chris, or, you know, because I have, um, the show, and the, you know, because I have the podcast that reaches so many people this week in startups, and I have the largest startup conference for our launch festival, I have a couple of things that he doesn't have, right, that can really help a startup.

AI assessment note: “in terms of how helpful I am, I know that I'm as helpful”

Q Point number one. I did like backward maths on it to just understand how that split up. It's about two billion dollars for venture and for early, um, is how that equates, and then, you know, seven billion across other vehicles, mostly growth. Um, so the nine billion is a bit misleading, but the question becomes to my tweet, if you're not playing the big game, Do you really matter?

A I think it's bad for, I think, listen, kudos to Lightspeed, right? They're playing the game on the field and, um, it's great. I do, I do think it's bad for seed VCs. I put bad in air quotes, right? Because whether it's two or nine and you got to slice these funds up to Harry's point, right? To really understand what's going on. It's not all nine for seed. It really means you don't care what you pay for seed. It just doesn't matter. And you work for speed and let's do the math. I mean, how, you know, what, This is why we have 20 or thirty million pre-seed rounds, because it just doesn't matter at that scale, does it? You just got to get into one hundred billion outcome. I'm not, I'm not saying it's bad, it just, it continues to contribute to the barbell, the barbell side of venture.

AI assessment note: “I do think it's bad for seed VCs.”

Q Would you call Sokka an angel though now? I mean, surely he was, uh.

A You know, I don't, you know, Chris and I are very good friends, and, you know, I think he's very selective right now, and he's kind of like laying back a little bit. So, I don't know exactly how to define Chris, other than he's a mensch and a legend. Absolutely. Just leave it at that, you know, what he chooses to do going forward, you know, who knows? I mean, I think the guy has done so well, he's got to, like, step back a little bit and think about, you know, gosh, if you hit, you know, it's sort of like being, like, Michael Jordan or something like that. At a certain point, you're like, well, I've got seven rings or six rings or whatever. Like, what am I playing for exactly? Yeah. And I think he's probably in that mode of like, hmm, I don't ever have to work again if I lived a hundred or a thousand lifetimes. What exactly do I want to do on this planet? And, you know, I have to say, when you look at the scorecard in life, you know, I sort of talk to people about the two scorecards.

AI assessment note: “I don't know exactly how to define Chris, other than he's a mensch”

Q Dude, business completely uninterrupted. Churn, zero, profitable, killing. Jason, rippling ordeal?

A Going to the start of the conversation, if we're ending the conversation. Um, a billion's still early to me today. Not because I don't have profound respect for a billion in ARR, but because I worry that for us to get our exits, we have to see enough acceleration past that point. So at the end of the day, deals pain point from, I think inception today is more acute than rippling's. Okay. It is an acute pain point. It is a problem that we've all lived as a founder. We've lived at very difficult to solve this, this international onboarding versus rippling is a very clever problem to upload. Right. Rippling was, uh, Zen payroll and Zenefits done better, and a problem that every US startup and company has, but there's, there's already point solutions there, right? So.

AI assessment note: “deals pain point from, I think inception today is more acute than rippling's.”

Q Um, and do you get security from investing in accelerated startups?

A I have my own. So, you know, for me, I would rather just accept people to mine and work with them. And so in my accelerator, we only have seven companies. I, we have 18 classes, and I come to 14 of them. You know, so if you look at Dave McClure or Sam Altman, you know, or Paul Graham, I think you might get as a startup, you know, you might get to meet with them once or twice or something, and you're one of a 120 or 50 companies per cohort. I've done kind of the opposite. Uh, I'm like, I say no to 20 companies I want to accept. And I just take the seven, and I spend a lot of time with them. So they get, like, you know, a lot of Jason time, where, like, if you join one Combinator, how much Sam time do you get? How much time do you get with Paul Graham? Probably very little. Um, you know.

AI assessment note: “I have my own. So, you know, for me, I would rather just accept people to mine”

Q Red Swish was a decent exit, wasn't it?

A Yeah, I think they did 25,000,030 million. Uh, Mark Cuban was an investor. Mark Cuban's invested in my companies. We're all kind of in the same, came up in the same web one point. Um, so I think, you know, people on their third, fourth swing at bat can do really well, whether it's Evan Williams with Twitter. He did, uh, he did Odeo and then blogger before that, but Twitter obviously was his third time up at bat. So I love founders when they're at the third time at bat. And when he showed it to me, I asked him if I could invest because I had passed on investing in Twitter and I passed on investing in Zingo, which are two of my very good friends. Other Startups. And I didn't really consider myself an angel investor, but, you know, it turns out that angel investing, I think at its best is, you know, investing in people, and investing in their passion, and trusting them, and it turns out, like, I'm pretty good at reading people. I may not be the greatest entrepreneur. I'm certainly not. Um, I'm definitely not the smartest guy in the room. Typically not. But I'm pretty, pretty darn clever when I need to be, and I,

AI assessment note: “Yeah, I think they did 25,000,030 million.”

Q Um, and do you get security from investing in accelerated startups?

A I have my own. So, you know, for me, I would rather just accept people to mine and work with them. And so in my accelerator, we only have seven companies. I, we have 18 classes, and I come to 14 of them. You know, so if you look at Dave McClure or Sam Altman, you know, or Paul Graham, I think you might get as a startup, you know, you might get to meet with them once or twice or something, and you're one of a 120 or 50 companies per cohort. I've done kind of the opposite. Uh, I'm like, I say no to 20 companies I want to accept. And I just take the seven, and I spend a lot of time with them. So they get, like, you know, a lot of Jason time, where, like, if you join one Combinator, how much Sam time do you get? How much time do you get with Paul Graham? Probably very little. Um, you know.

AI assessment note: “I have my own. So, you know, for me, I would rather just accept”

Q A really interesting one. Where's the future of podcasting?

A Well, here's the thing, you know, I started this podcasting company this weekend with my friend Kevin Pollack, like, six years ago, and then we gave up after about three or four years on trying to get other people to do it. Because it seemed like only, the only way it worked is if some crazy maniac with a really good reputation and network was willing to work for free for a couple of years, and then the podcast would magically work in year four or five, like Adam Carolla's is, or Kevin Pollack's is, or Leo Laporte's is, or mine does. So we may have given up too early, you know, on this weekend, um, and doing that network, but we just couldn't get people who were, we could get people who were up and coming to do podcasts. We couldn't get people who were arrived to do podcasts. Up and comers, You know, they got to spend four or five years doing it to even get somebody to pay attention and maybe sponsor. If you're somebody, it takes two or three years to get somebody to get people, you'll get people to pay attention in year one if you got a little bit of an audience, but it'll take two or three years to get revenue. So, you know, this week in startups is now, it's 5000 dollars in advertisement. We do a 104 episodes a year, two ads, so it's 208 ads a year. Some people get discounts. I mean, it's, it's going to hit a million dollars in revenue. Um, and there's like four or five full…

AI assessment note: “it's going to hit a million dollars in revenue.”

Q Um, I want to start with, we were just talking beforehand about how in the 58th week of this week in Anthropic, we say anything different and provide different commentary. The question that I'm going to start on, Jason, is one that you just highlighted brilliantly, I think, which is Anthropic files to go public. Is Anthropic filing to go public and going public good for the ecosystem or not?

A Listen, we, we, we don't need to talk about how the ARR increased 28% since the last show. I mean, it's pretty good, ok? It's, it's the fastest growing enterprise software startup of all time, of all universe throughout past Alpha Centauri. But now it's also going to be the, probably the fast, certainly the fastest to IPO to anything near its scale, right? This door of SpaceX is going to IPO in five years, five years to a trillion, ok? Cursor acquired for sixty billion in four years, assuming the deal closes, ok? Why would you bother with most of the companies in our portfolio? Why would you bother to even meet the founders? Why would you do anything as a VC? No, other than spend the next 24 months hunting these. And as an employee, here's the really tough question. Why would you work for any of these companies? Like we have the CEO of Ironclad is now the head of legal at Anthropic, right? Or OpenAI. Sorry, I got backwards. Jason Boeing, or is that he, he, he, he leaves, maybe he's still chairman of Ironclad, but, um, why would you do anything When you can build a trillion, when there is, there is not impossible to build a trillion dollar startup in five years, why would you rationally do anything else? Why would you even try to have a four hundred million dollar exit, two billion dollar exit? Isn't just a waste of our time? I mean, I know, I know Rory will pick at this, don't …

AI assessment note: “Why would you bother with most of the companies in our portfolio?”

Q If I pressed you on saying who the winner of that will be then. Who will that be? Will that be a cursor? Will that be a claw code? Will that be a figma?

A Honestly, and I know this sounds Captain obvious. I honestly think it's going to be who wants it the most. You almost have to work so hard. You have to 12 12 nine as hard as we're working at cursor and it's been great. We might have to work even harder, but maybe Figma works even harder. I know this sounds silly, but everyone can copy each other in weeks now, not in months or years or quarters. And it's who really, really wills it into existence. I don't think we can sit back as VCs and just even with our kink Great King making checkbooks. I don't think we can fully control the outcome. I think the ones that work that produce 10 times more output are honestly the ones that are going to win the leaders. I don't think we can predict. It's easy to bet in favor of cursor over Figma because Figma took what a decade to get to a billion and cursor took, you know, a year. So if we're momentum better bettors, we have to, we have to bet cursor, right? Even though there's reasons to bet against it, right? They don't, they're not designers. They don't have the base. They don't have the customers. But if I had to pick, I would bet on that, that, that, that rapidity today.

AI assessment note: “if I had to pick, I would bet on that, that, that, that rapidity today”

Q Jason, how do you square that away though, with your statement before, which I always remember, which was, you know, you can see a future where you have so many more instances of Superbase and you need like, 10 X more. You just couldn't consume enough compute combined with Benioff saying .1% of Salesforce Has AI. What happens when 50% have it? How do you square away those two opposing?

A I don't know that there's, it's a good, like, I'm, I feel like I'm becoming one of those curmudgeons that says you should only invest in trillion dollar markets. I'm, I'm agreeing with it because, I mean, Amazon just went down in part, I mean, whether it's DNS or whatever, it's database contention with Dynamo because so many folks needed, uh, databases and Supabase hit Amazon issues because so many people need databases. So look, listen, every single app in the world needs A database. And what's changing is now folks might need 10 databases or 20 databases instead of one. So it actually is just the point. You should take more and more super base risk investing because the TAM is not only massive, but even bigger and maybe do less vertical AI agents that you think makes, uh, that, that is like a small part of what service Titan does, but it's, but it's amazing, but it also might increase the odds your portfolio comes up snake eyes. Cause you're trying to do all the super bases at pre-revenue at 200 or like, or like, uh, you know, throw, throw the dice at them at five K a month in revenue. You're gonna have a high loss rate too.

AI assessment note: “You should take more and more super base risk investing because the TAM is not only massive”

Q And how do you manage that? How do you ensure that you don't Lose one side of your life whilst the other grows. Obviously, incredibly successful.

A You have a huge amount. Maturity. I mean, there's a lot of maturity that occurs, I think. When you're young, I think you're driven by adrenaline. You're driven by a lot of different things. I know a lot of driven people, obviously, and I invest in some of them, and your drive when you're young, I think, and what makes young people successful is sometimes a very basic Motivation. If you look at Maslow's hierarchy of needs, if you look at the dynamics and the psychology of motivation, competitive motivation is a very immature motivation. It also happens to be perhaps one of the most powerful. Uh, so Michael Jordan or LeBron James, they got up for the competition, right? They wanted to be number one. I really want to be the number one angel investor in the world. I, I, I desire that. I want to be better than anybody else. Even Chris Sacco, who's a dear friend, even Tim First, I'm competitive. I would like to be better than them.

AI assessment note: “I really want to be the number one angel investor in the world.”

Q I have seen before, to be fair. The company scaled to two and a half billion dollar valuation and very quickly has been very successful. I'm not going to pick on Corgi. I don't want to, but I'm just asking, in your best performing companies, Are you seeing a different level of intensity and work ethic than you've seen in prior cycles? Or is this just kind of rage bait?

A Can I simplify it? My, my learnings. I wrote this on Twitter, but so my very first startup job, I told the start, my very first startup job, I never worked at a startup before and I roll in on Saturday to the office at nine AM and it's me and the co-founder. And I'm like, well, I've never worked in tech before, but in all of my services jobs, I worked six and a half days a week. I worked night. I didn't, we just didn't call it nine, nine, six. I just had to work six and a half days a week before I worked at a startup. And he's like, it's so great to have you here. I haven't seen anybody in the office on a Saturday morning in a long time. So he was there, right? Founder was there as a founder. I worked seven days a week, right? Um, I think the only thing with nine, six, I think we're getting confused. There was a while in late, 20, 2020, 21, when no one really worked. But in generally it's just how deep does it go in the organization? How deep does working Saturday and Sunday go? And, um, I just think while many folks think it's toxic, if you're trying to build, I remember what the cognition guy said, what's the CEO's name? The cognition guy.

AI assessment note: “There was a while in late, 20, 2020, 21, when no one really worked.”

Q What do you make of YC's scaling? It's an often controversial topic that I've heard many investors discuss, moving even to two days now. What do you make of it and the quality that's happened to the startups?

A So, it's easy to criticize Y Combinator because they're a little persnickety on the edges, they're a little bit, I think it's some people's perception, but I'm a little persnickety and cocky too. If you're good to do, you should crow about it a little bit. So I think a lot of the hate at Y Combinator is candidly people who are threatened by them. Now I'm not threatened by them. People who go to Y Combinator wind up coming to my incubator and do my incubator after it's happened. And I've had people who do my hackathons or who do my, my incubator and then go to Y Combinator. To me, it's great. Sam Altman and I have a great relationship. You know, we, we, we've had our debates in the days. We play cards together sometimes.

AI assessment note: “I think a lot of the hate at Y Combinator is candidly people who are threatened”

Q you. I think it's easy when you love what you do, but I want to talk about you today. This is about you. You've got a fantastic new book. As everyone who listens to the show will know, I don't read very often, but when I read this book, it was incredible. So talk to me about the book, and why now for you? Why was now the right time?

A Great question. I revere books. I think people write books largely for the wrong reason, and you've probably had this experience where you know somebody who You know, they're an acquaintance or even a friend, and you think, this person is not the sharpest knife in the draw, and they come up to you one day, and they hand you their book, and you think to yourself, this person is not very successful at what they do, and they've written a book, and you go, why is this? Why would you waste all this paper and everyone's time? As you said, you don't read a lot of books. It's a major commitment. Five, six, 7:08 hours of your life. The price is a great deal, right? Books for 10 or 20 bucks. I mean, I think it's a pretty amazing value proposition. They should probably cost 50, I can't understand why books are so cheap. Putting that aside, I think the reason they're so cheap is because so many idiots write books, and so over the years, I've been offered to write a lot of books. For 10 years, I've had the great, over 10 years, I've had the greatest book agent ever, John Brockman, who does edge.org, which if you're a scientist and you're into science and technology, you probably read Larry Page and Elon Musk will all read the website. It's edge.org. It can't say enough good things. But anyway, I turned down doing blogging for dummies or Like podcasting for dummies, or startups for dummies. …

AI assessment note: “I turned down doing blogging for dummies or Like podcasting for dummies”

Q You mentioned kind of later liquidity there. I'm really intrigued because Uber's famous for not providing such later liquidity to investors. What are your thoughts on that and the constraints around that?

A It depends on who you are, and it depends on when you invest it. So typically people in the later rounds are locked up, but the earliest investors are not. And depending on your relationship with the company, you can have a different opportunity than other people. So I think it's important People have a lot of different questions I like to ask, and there is no exact right answer, and I, I ask different questions, um, at different times, but I think I like to ask very open-ended questions, because I'm trying to get a read on how things are going, why they're doing what they're doing. So the shorter the question I find, and you probably have experienced this as an interviewer of 850 people, or a thousand and a 150 people who didn't get on the show, what are you working on is a great question. I consider that like a great first question. And the reason I ask it in that way is that in a way it celebrates the founder and what founders do. You and work, right? Those are two of the five words in that sentence. What are you working on, Harry? And it's work. We know you're working on something, right? You're not a talker. You're a worker. And why are you doing this? Again, it's five words, but it really is one of the most telling questions you could ever ask people. And I just sit there very quietly and listen to them. And I let founders speak and speak and speak until they have nothing…

AI assessment note: “People have a lot of different questions I like to ask”