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The One Man Accelerator at The Four Seasons & Why VCs Can Be Sharks | Josh Browder

Josh Browder is my favourite emerging manager. As the Founder of Browder Capital he has been the first check into unicorns like Micro1, [Owner.com](http://owner.com/) and Yuzu Health to name a few. He turned his Thiel Fellowship Grant of $100K into a whopping $10M angel portfolio. All new investments move into Josh's Four Seasons Residence where he then trains them on company building. They are only allowed to leave when they raise their seed round. In addition to this, Josh is the Founder & CEO @ DoNotPay, the now profitable company that has raised $22M from Marc Andreessen and others. ----------------------------------------------- Timestamps: 00:00 Intro 01:34 Why Young Founders Have No Option But to Succeed 04:39 What Joshua Looks for That Others Miss 06:55 How to Spot a Fake Founder 08:54 Joshua's One-Person Accelerator 11:14 The Three Reasons Pre-Seed Companies Fail 16:04 Breakfast With Marc Andreessen at 18 37:38 YC vs Joshua's Spare Bedroom 43:08 The 1000x Investment: What Joshua Saw in Ali Ansari 45:51 IQ Is Overrated 46:59 Never Tell Founders What to Build 1:03:07 DoNotPay Pays Dividends 1:05:29 Hire People Who Scale Themselves 1:07:36 AI's Winners and Losers: The Giant Transfer of Wealth 1:09:26 Why Joshua Buys Land With Every Dollar He Makes ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Joshua Browder on X: https://twitter.com/Joshuabrowder Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #joshuabrowder #startups #peterthiel #donotpay #angelinvesting

Josh BrowderguestHarry Stebbingshost
May 18, 20261h 35mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:34

    Intro

    1. JB

      If you're not motivated by the fear of losing, I think you're asleep at the wheel. At the very beginning, there's three reasons why pre-seed companies fail. They run out of money, they run out of hope, and [beep]

    2. HS

      Now, if I could invest in one emerging manager, sub $50M fund, it would be this manager today, Josh Browder, Browder Capital.

    3. JB

      There are three types of people: those who make it happen, those who watch it happen, and those who wonder what happened.

    4. HS

      He makes founders that he invests in live in his spare room at The Four Seasons until they raise a seed round.

    5. JB

      Pitching VCs is like a game of poker. You should never reveal too much information about what you're seeking.

    6. HS

      Also, he turned his Thiel Fellowship 100K grant into a $10M angel portfolio. He was one of the first investors in companies like Micro1, Yuzu, and many more.

    7. JB

      For every Anthropic employee who's making 20 to 100 million, there's 7,000 Block employees being laid off. It's not sustainable. You can't have 50,000 people with all the money. I think actually there could be a revolution in our lifetime. Something has to change.

    8. HS

      Ready to go? [upbeat music] Josh, dude, I am so excited for this. You mentioned very kindly before the show about my levels of prep. I, I think it's stalking to some extent, but I have loved getting to know you. So thank you so much for joining me first.

    9. JB

      Thank you for having me. Growing up in the UK, um, I'm proud to have known of you before you became a world-famous

  2. 1:34 – 4:39

    Why Young Founders Have No Option But to Succeed

    1. JB

      podcaster, so.

    2. HS

      [laughs] Dude, I, I think most of the stuff I post these days actually just, uh, rage baits most people on LinkedIn. [laughs] But I wanna start with one that I always actually wonder with CEOs that I interview and meet, which is, what actually inspires or motivates you more? Is it the fear of losing, or is it the immense satisfactory feeling of winning?

    3. JB

      If you're not motivated by the fear of losing, I think you're asleep at the wheel. Um, there... Only the paranoid survive, and the world is changing. It feels like the world is changing a year's worth of progress every few weeks, so definitely the fear of losing.

    4. HS

      You know, when I started, you very kindly said, like, um, about get- getting to know me through the show. I still kind of have this to this day, in all honesty, and this is why the show's become more and more successful is 'cause I don't really care what people think. But, like, I was terrified of being Macaulay Culkin. You ever seen... And he was very famous when he was young, and then, like, nothing became of him. And I was terrified of being the, like, shot in the pan. Did you ever have that? Because you were very successful young, and I remember seeing you in the same vein, like on magazine covers, raising $22M. Did you feel that pressure early?

    5. JB

      There's a saying among the Thiel Fellows that, um, they have an expiry date. And we all know these people who are very hyped and then maybe didn't, uh, stay relevant, and they just... Some of them lost their minds, and so that was always a huge fear of mine. You always have to constantly be reinventing yourself to kind of stay relevant and adapt 'cause the world changes very quickly. But I started DoNotPay in high school when I was 17, and that was a completely different world back then. That was in 2015.

    6. HS

      Dude, it was so, so different. I, I am actually just gonna start with that actually and, and kinda mix up the schedule because you bet intensely now often on very young founders, and I spoke to so many of them before this show.

    7. JB

      Yeah.

    8. HS

      Why is it that you place such a bet and conviction on very young founders so much earlier than maybe others would?

    9. JB

      So I think young founders have no option but to succeed. Um, if you back a Google engineer, um, the first thing they'll do is they'll hire 10 of their friends, and it's like this endless, like, scheme of hiring. Um, the first thing a young founder will do is they'll build the product, and they don't have anything to fall back on, especially if they have a chip on their shoulder. They, they really... The only thing they can do is succeed. And so I think the grit level with young founders is 10X, and being an entrepreneur is like eating glass. If you don't, like, um, have a true kind of dedication to win, uh, they'll y- they'll give up at the first opportunity.

    10. HS

      It is the shittest question, um, which I've often been asked, but actually I've found there's more and more nuance to it, and Dak should- Graptal told me I should ask this. He said, "Y- you back founders that others maybe wouldn't when you actually look at them in that instance." What is it that you look for that is non-obvious or atypical in the founders that you do invest

  3. 4:39 – 6:55

    What Joshua Looks for That Others Miss

    1. HS

      in?

    2. JB

      So the number one thing I look for is a deep connection to the problem, that they won't give up. So I, I, I go back to my own journey. I'm Mr. DoNotPay. Um, I'm the type of person to get 10 parking tickets just to test out the service or wait on hold for hours to save 20 pounds or dollars, I guess. Um, and I look for those founders with, with a really deep connection to the problem. So for example, I was in the very, very first pre-pre-seed of a company called Owner.com with Adam Guild, and he built the initial version of the p- his product to help his mother's dog grooming business. And so many of these founders come up with these BS stories, but, um, that is a real story, and he really did it to help his mother. And similarly with me, I, I really did it because I hate the government with parking tickets. And so I look for that sort of founder-market fit where they're, they're their own first customer. And I joke, if you're building for yourself, at least you have one customer.

    3. HS

      Do you worry about the susceptibility of founders when they're that young? Like, bluntly, I see a, a lot of very young founders now getting so caught up in the fundraising game that it's like, it's almost a game of, "I raised a round" and "From who?" And it's like-We're building a business to create a product for customers. Let's not forget why we're here. Do you worry about that?

    4. JB

      Yeah. So I escaped the UK to go to Stanford, and there was a, um, Stanford Review article, which is a student publication, and the publication said it's easier to, for a f- a Stanford student to get into YC than it is for them to get a job now. And so we've seen a rise of, um, I would say, fake founders, where they don't have that connection to their problem and they're just starting something just because it's cool or because they have nothing to do for the summer. And actually, being an investor, you have to be very careful about backing students over the summer, um, because part of the signal is they've dropped out and they're going all in on this, but of course, during the summer you can't actually tell if they've dropped out. So, um, I'm actually i- scale back a bit during the summer, not because I'm in Capri like all the other VCs, but because you have to worry about these fake founders.

    5. HS

      How do you determine whether someone is a fake/tourist founder versus not? I look at some of mine more recently actually, and, and I've made this mistake, right? I thought they were mission-driven, and it transpires afterwards that

  4. 6:55 – 8:54

    How to Spot a Fake Founder

    1. HS

      they're not.

    2. JB

      So I have a, a huge list of heuristics, and I i- have small signals and big signals. So a small signal would be, um, let's meet at 11:00 PM. And, um, the, the best founders would say, "Sure." Um, the mediocre ones would say, "Oh, no. Um, can we meet, uh, Tuesday week?" Um, so we meet at 11:00 PM, and, and then we just, I just like hit them quick fire with questions. And everything they say I want them to validate, and it's almost like a visa interview. So for example, they'll say, "I'm at 5,000 in revenue." I say, "Let's look up your Stripe right now." And, um, the, the, the fake ones get really nervous. They're, they're like, "Oh, I don't have my Stripe on my phone." What serious entrepreneur doesn't have the Stripe app on their phone? Um, and then I go into, like, these tactical questions, like what's your goal for the next three months, six months, one year? Um, a D-minus answer would be some vague nonsense like, "I wanna get a partnership with Anthropic." Um, an A-plus answer would be, um, "I'm going to like fly to Milwaukee to meet with a dentist to get them to sign my $500 a month SaaS plan." So it's like very tactical. Then I look for, um, do they have a top 1% skill in something to achieve their business goals? And you see the best entrepreneurs, they've proved something in their childhood. Um, maybe they were selling Minecraft servers, like Adam Guild or John Andrew, the founder of Wonder. Maybe they were doing sneaker bots, like the founder of Whopp. Um, my generation, when we were growing up, it was very big to do jailbreaking. So jailbreaking or competitive drone racing, so many of these things. And it doesn't have to be engineering. Like, I backed the youngest engineer at Amazon. That was really cool. But it can also be distribution and, like, making sure their sneaker bots get to the, the right audience.

    3. HS

      I heard from some of the founders that you will house them in a, a Four Seasons Residence. [laughs] Can you talk to me about this and how you structure that environment

  5. 8:54 – 11:14

    Joshua's One-Person Accelerator

    1. HS

      that you put them in?

    2. JB

      I, I noticed over the years... So I've, I've tried all sorts of investments over the years and, and things have done very well, but the best sort of investments are the day one investments for me, and I think everyone is playing different games. Um, some people are playing the games where they're getting into the hottest companies, 100 million valuation, and then they become worth 25 billion one day. Um, the game I'm playing is, um, I'm getting into founders who when they're just starting they're not polished at all and they can really use my advice and my reliving my founder journey to polish them, and, um, I try and get in sub 5 million valuation. And the question I'm sure you have is, how do you account for the adverse selection of getting in at those low valuations? And I noticed that over the years the best founders that I invested in, I actually live with them at some point. Um, I was roommates, uh, with, uh, the founder of a company called Assured, um, where we both rented the house where Facebook was started over the summer at Stanford. Um, I was roommates with the founder of a company called Yuzu, where, um, he worked at DoNotPay, so he lived at the DoNotPay house. The founder of Micro1 lived in my spare bedroom, uh, when I f- was his first investor.

    3. HS

      And what is it you see in the best in those periods?

    4. JB

      So I've made so many mistakes with DoNotPay. 10 years, I'm 10 years in now. I can give them a crash course so they don't make the same mistakes as me in a matter of three weeks. And bear in mind, these are very young college first-time founders. So they don't even know the difference between pre-money and post-money valuation and all of this. So it's almost like a one-person accelerator. It's, it's one person, one partner at the accelerator, me, and then one, one founder or one company. Um, and you mentioned Four Seasons. Um, I would say it's not that luxurious. It's adjacent to the Four Seasons. It's technically a Four Seasons residence. But sometimes if there's four co-founders, it's four beds in a, in one room. So I'll, I'll rent beds for $50 a night, and then they all, um, one company, they live in one room. And I say to them, it's like it's in California, so it's like Hotel California, where you can't check out until you've raised your institutional seed. And then I, the company is off life support, and I can, like, relax a bit.

    5. HS

      I can... I, I just have to kind of-

    6. JB

      Yeah

    7. HS

      ... delve into this process. What are the main fuck-ups that they make in that period where they're there? What do you need to shape, polish, or create in

  6. 11:14 – 16:04

    The Three Reasons Pre-Seed Companies Fail

    1. HS

      that period?

    2. JB

      At the very beginning, there's three reasons why pre-seed companies fail. They run out of money, they run out of hope, and co-founder disputes. Um, the running out of money is, comes down to pitching, and I help, um, I'm lucky to have pitched almost everyone in Silicon Valley over the years, successfully and unsuccessfully. And so I teach them how to present their business. Um, running out of hope is, is also really important. I want them to make them feel like they're making progress every single day. Um, so I'm like en- encouraging them to ignore all of the kind of vanity signals of being a young founder in SF and actually focus on their customers. And then co-founder disputes and building the team, I sometimes recruit my, uh, smart friends who are not ready to start a company into their organization, and I get them the vesting and all the boring stuff. Uh, like everything that YC would say, I, I, I say to them.

    3. HS

      It's so interesting there. We had money, hope, co-founder dispute.

    4. JB

      Yeah.

    5. HS

      Co-founder dispute is one that really kills companies, I find. How do you measure, analyze co-founder relationships when they're staying with you, and any lessons there?

    6. JB

      So the good news is that with all sort of red flags, young founders are very bad at lying. So, um, if they say we're, we're kind of best friends, and then they start interrupting each other, you kind of know that that's not true. Um, so I look for kind of a long history. The best co-founder dynamic that I've seen among young founders is friends from high school. So I, I was the first... And they live with me as well. I was the first investor in a company called Halidea very recently, and they were, uh, friends from high school, went to different colleges, dropped out and rejoined. So that's the, that's the kind of perfect, uh, dynamic. Um, one thing I'll say is I, I've noticed a really worrying trend of people reverse engineering what I say on podcasts and in articles to pitch me exactly what I'm looking for. So sometimes, so just now I said, um, friends from high school. I can guarantee you in three weeks someone is gonna say, "We were best friends in high school." And so this is a worrying trend where they're using Claude and ChatGPT deep research, and so I have to worry about that.

    7. HS

      It's, it's the biggest challenge that we actually have 'cause w- I've been very prescriptive in the past that I look for, and this sounds awful, but, like, family trauma is a big sign of, like, future-

    8. JB

      Exactly

    9. HS

      ... founder success.

    10. JB

      Yeah.

    11. HS

      Gaming and then early entrepreneurial success. I would say 9 out of 10 young founders that we meet pitch those three exactly, and you're like, "Wow, [laughs] this is very aligned."

    12. JB

      Yeah. It, it's disgusting. Um, it's a ce- certain type of fraud. I call it ideological fraud.

    13. HS

      [laughs] I agree completely. Can I ask you, when you bring them into the house, is that when you put the money in?

    14. JB

      Yes. Um, so I put, I put it in just before. Um-

    15. HS

      Okay. And, and is that a same size check at a certain p- price?

    16. JB

      Yeah, yeah, and it, it varies depending on how many co-founders there are. If it's just one... I sometimes, I sometimes I, I don't mind solo founders. Um, if it's, like, three dropouts from Harvard, then the price reflects that.

    17. HS

      Do you find that 5 million price is still attainable?

    18. JB

      It c- That's, that... It s- sometimes can be lower, sometimes can be harder, higher.

    19. HS

      Because I just find dropouts from Stanford or Harvard in particular-

    20. JB

      Yeah

    21. HS

      ... just see TechCrunch and see Twitter, or X [laughs] and, uh, go, "I'm, I'm 25. I'm, I'm a CS grad from Stanford."

    22. JB

      O- oftentimes it's so early that it's, it's, it's definitely possible. Um, for, from my latest fund, um, it's... I've done 33 deals so far. The median across the entire fund is five. The minimum is 1.5, maximum is, uh, 21.

    23. HS

      Do you worry about the level of fraud that's going on with the current ecosystem with the founders that we're seeing? Uh, do you worry about that increasing with the pressure we're putting on?

    24. JB

      I think that at the earlier stages, the only fraud there can be is ideological, which is not illegal. It's not illegal to say you've had childhood trauma when, when you've actually grown up middle class, and that's a huge, huge issue. It, it's interesting because the best founders are hustlers in some ways. Um, so it's, it's a, it's a balance. Um, I actually think it's becoming easier and easier. The world is becoming much more transparent. Um, you have Twitter sleuths who will detect anything. As, like, several companies recently have been taken down because of, like, someone published an article about SOC 2 or something like that, and the entire company is done. Um, so I think actually fraud, the, the illegal type of fraud is becoming harder.

    25. HS

      You mentioned you've s- pretty much met every venture investor in the Valley. What was the best venture investor meeting you had? You know some where you just meet them and you're like, "Wow, this, this person is really [laughs] smart."

  7. 16:04 – 37:38

    Breakfast With Marc Andreessen at 18

    1. JB

      I, I think it was Marc Andreessen. Um, like so many founders, I, um, after DoNotPay got, um, all of the hype and, um, we were starting to get a lot of usage, um, he reached out on X and he said, "Do you want to have breakfast?" And I was very mission driven. I w- I was not one of these, like, cust- like, Stanford founders or anything. I was actually on the verge of making DoNotPay a nonprofit. In fact, I had a pitch to, like, nonprofit-style investors. Not investors, just funders, to make, like, a legal nonprofit to help people with their rights. I was that focused on fighting the system. And I went to this breakfast, and Marc convinced me that the biggest organizations are for-profit entities, and you can have 10 times the impact of a for-profit company because the incentives are aligned. And DoNotPay was a very small example of this, but I guess you're seeing this today with OpenAI, with the $150 billion lawsuit, um, where they switched from non-profit to for-profit. So that was the first major lesson I learned, I would say.

    2. HS

      How old were you at that breakfast?

    3. JB

      I was 18 or 19. Um-

    4. HS

      Were you nervous?

    5. JB

      I, I was so nervous, and, um, it was a breakfast meeting.

    6. HS

      Where was it?

    7. JB

      It was, it was very... It was at his hou- at his house in Atherton, and he came down in, like, breakfast clothes, and-

    8. HS

      What are breakfast clothes? [laughs]

    9. JB

      I was, I was fresh off the boat. I'm not trying to get in trouble, but I was, like, fresh off the boat-

    10. HS

      [laughs]

    11. JB

      ... from the UK. Came down in breakfast clothes, and, um, yeah. He's, he... Um, but I would say all of the luminaries are incredibly nice people. Um, yeah. But Marc Andreessen is by far my favorite, and I'm very fortunate. He's my first investor at DoNotPay and also first invest- first institutional investor for my fund.

    12. HS

      That, that is-

    13. JB

      Yeah

    14. HS

      ... absolutely amazing. I love that. I also love breakfast clothes. [laughs] I have no idea what that is. Do you think venture investors add value? You know, Keith Rabois says, "The best founders I work with, honestly, they don't need venture investors." Most VCs on LinkedIn or Twitter tell me that I'm an idiot for saying that. Do, do you find that to be true? What, what side of the fence do you sit on?

    15. JB

      I have a friend, he has a great saying, which I'll copy, "There are three types of people: those who make it happen, those who watch it happen, and those who wonder what happened." And, um, I think at best venture investors are in the second one. Um, sometimes, unfortunately, they can be in the third. So the biggest issue is, like, they don't go crazy on the founders, which happens a lot. Um, but of course, they can add value at strategic points.

    16. HS

      Going back to the, the core ingredient of success in venture that the founders themselves, you, you're a dropout. Um, how do you think about the value of university today? And if you were sitting with, you know, a, a university student today advising them on whether it's worth staying or worth pursuing a dream.

    17. JB

      People see their life as paint by numbers. So they say, "If I g- go graduate, I go to business school, I go work at X company, then in five years I'll be ready to start my company." The problem is the world changes so quickly that the paint by numbers approach doesn't work anymore. And so I would say to any founder who has an idea of what they want to do, they should just go for it, and the world won't wait for them. Um, on the other hand, you see a lot of people drop out just for the sake of it. In fact, um, when I, when I dropped out, um, in 2018, I actually had, like, one or two classes left at Stanford, so I was very close. Um, it was very kind of taboo to drop out. Um, now dropping out is almost the establishment, so you see people drop out just for the sake of it. And I think that's definitely wrong, um, because there are huge advantages to co- to being in college. Um, w- even if you're doing a startup, like, you can recruit your friends, um, you have your college email, and people will, um, take you more seriously if you email them from Stanford or mit.edu. Um, also, people give college students more of a free pass. Um, if all of these founders who are getting this controversial stuff were in college, they, they might, they might be able to kind of pivot more quickly.

    18. HS

      Do you think... You know, your, your father's an incredible figure, incredibly respected figure, but there was a little bit of a safety net. Do you think that your ability to have a safety net slightly enabled you to drop out?

    19. JB

      No. I think, um, the, the opposite was true. So I was sitting at, um... And I've never told this story before, but I was, um, sitting at a poker game at Stanford with my friends. And this is no exaggeration, I, I got a, um, news alert, um, saying... Uh, so my father is a human rights activist, and he's, like, a enemy of the Russians, and it was a news alert about my father, and this, uh, that he'd just been arrested. They'd just... The Russians managed to get him. And I think it's taught... It's just made me incredibly paranoid. And so I, I think I was more paranoid, um, because of, uh... Most people, um, don't have the mafia after your family. And, and so I, I was extr- um, always cons- like, paranoid and fearless. And so I think actually, um, it ki- it kind of made me m- more, more paranoid to, like-

    20. HS

      Take big swings

    21. JB

      ... yeah, take big swings. [laughs]

    22. HS

      What did you do in that moment?

    23. JB

      I called him. Then the... It didn't go through. [laughs]

    24. HS

      [laughs] Hopefully good.

    25. JB

      Then I called my mother. Um, and then I, like, cashed out my chips and left the poker game and dealt with the situation. A- and as a 19-year-old college student, there's very little you can do in that situation. And, um, but my biggest thing was trying to make sure he didn't get extradited to Russia, because if he got extradited, really bad things would happen. Um, and so I went to an event, British students at Stanford, and it was hosted by the, um, um, consul general. And I thought, the one thing I can do, I maybe I, like, email the consul general. So even as a teenager, I was just trying everything. Of course, that made no difference.

    26. HS

      [laughs] Do you know what I find very funny? Is [laughs] if you, if you had been like, "You know what? I'll deal with this later. I'm playing poker right now." [laughs] That is, uh, that, that is quite the story. I'm, uh... Yeah, that, that, that-

    27. JB

      Yeah, it was a Financial Times news alert.

    28. HS

      Yeah, that's, that's pretty terrifying. Can I ask you, when you think about, like, a really challenging time like that, seeing that news, can you take me to a really hard day you had with DoNotPay, and how did you learn about yourself from it?

    29. JB

      So this is probably the, the hardest point of DoNotPay, which is, um, three years into the company. So I, I'd raised the pre-seed from Andreessen, from M- Marc. Um, and it came time to raise the seed, like, two or three years later. And DoNotPay was incredibly popular. Millions of people were using our free product, and I thought it was a slam dunk pitch, and that was a huge mistake. And I was going down Sand Hill Road because all the VC's funds were in Sand Hill Road back then, and one after the other, they were rejecting me. I, I w- I went just down the list, rejection, rejection, rejection. And this was really depressing because I'd actually just dropped out, like, a week before. And there's... As passionate as I, as I was about DoNotPay, there's only so far I could go with just me. I needed to hire a real team and then raise some serious money to keep it going. And I had, like, two or three pitches left. Um, and I thought, "If these don't go well, I'm just gonna throw in the towel and, like, do something really depressing like, like, go work for big tech or, or something. Go work at Google, um, because I, I just have to give up. Maybe even go back to Stanford." And, um, so it was the next day, it was one of my last pitches, and, um, I, I guess this kind of speaks for, um, how bad the situ- situation was, but I turned to my outside counsel lawyer for advice. If you're turning to outside counsel for, like, business advice, then you know things are really bad. [laughs] And, um, he's an amazing lawyer. He's a partner at a firm called Wilson Sonsini. His name is Damien Weiss. He's, like, on the cap table of all the l- um, amazing companies. And, um-I, I told him the predicament I was in, and he said, "Well, do the whole pitch in front of me right now." Um, and so I gave him the whole pitch, and he interrupted me halfway through and he said, "You're doing it completely wrong." Um, he said, "First of all, they're not investing in the, the PDF deck or some presentation. They're investing in you and the product. And so the fact that you're not doing a demo is criminal." And, um, so I've qui- kind of quickly scrambled together a demo of a robot appealing someone's bank fees because DoNotPay was expanding to bank fees in the US, and added that to the p- presentation. He said, "Second of all, um, no one really knows what this can be. You should put the logos of the biggest companies that you one day wanna emulate." So I stuck in the logo of Intuit, which is a $200 billion company in the US, and I said, "We wanna be the TurboTax", which is one of their products of consumer rights. And I also put the Honey logo, which was just acquired that year for 6 billion, and then I put Credit Karma, which was acquired for 8 billion, put that in the deck. He said, "Finally," um, this was around the time of the Cambridge Analytica scandal, um, "you shouldn't say you wanna do advertising. Advertising is not very fashionable right now w- among VCs." Um, so I, I said, "Okay, what should I do?" He said, "Subscription." So I put in subscription. And I didn't even really believe that it could be like people would subscribe to it, but I put in subscription, and it, he turned out to be right. Everyone, uh, w- now subscription is our main business model. Anyway, so I made those three very minor changes to the deck and did my presentation the next day. And Harry, it was like a night and day difference, and everything changed. Not only did they wanna invest, they like... They left m- I left the room for a few minutes, and I came back, and they wanted to invest on the spot. And, um, first of all, all, uh, Silicon Valley is such a kind of herd mentality place, even the people that previously rejected me, once they found out that this firm wants to invest, everyone started to like r- rescinding their rejections. A- and, and I thought that was a bit depressing. And s- and second of all, um, it taught me a really valuable lesson, which is, um, nothing changed about the company, nothing changed about me, nothing changed about the team, nothing changed about our usage, but the most minor differences in framing and strategy made all the difference. And that's actually the, like, some of the lessons I give the founders I invest in. If things aren't working, you just need to change the framing just slightly, and that can make a, like, monumental difference.

    30. HS

      What do you find is the biggest problem with the framing that founders often come in with?

  8. 37:38 – 43:08

    YC vs Joshua's Spare Bedroom

    1. JB

      individual

    2. HS

      We said there about the external-

    3. JB

      Yeah

    4. HS

      ... validation and kind of some group like thinking. I, I am interested because often... [sighs] I don't know how to put it, but like the Thiel Fellowship and say like a YC are compared in the same bucket. How do you advise founders on the value of YC today and how they should think about that?

    5. JB

      Every founder needs some fast believer, whether it's taking my spare bedroom or the amazing programs out there, the, um... I really think you, you need a fast believer, and YC can be a great fast believer for them. I think, um, some companies do better in YC than others. The problem with any accelerator, not spec- speaking specifically about YC, is you're competing for attention with all the other companies in the accelerator. Um, if you're the top of the accelerator, then that's incredible. You're the king-made or queen-made company. But if you're like a middling company, it might actually be better to not be compared to all those other companies. And going back to my spare bedroom, um, it's a supply constraint. There's only one spare bedroom, and so it actually is a bar for me as like do I want to put these people in my spare bedroom? And there's only one, so I, all my focus is on them, so there's no dilution in terms of the brand. Like, I'm not doing 100 companies in my spare bedroom. In fact, one of my LPs asked me, "Why don't you start buying a hotel or rent out a hotel and just do 10 at a time?" And I said, "Well, that's, that removes the artificial constraint of one." And so I think that's why I try and be different. It's like a one-person accelerator

    6. HS

      I have a unwavering man crush on Matthew McConaughey, and he actually says something brilliant, which is, "Limitations reveal style."

    7. JB

      Yeah

    8. HS

      And I, I think it's very much aligned here to the constraints of your... [laughs] I would love to partner with you, Josh, and say, "Hey," [laughs] this is the content marketer within me, "Hey, could we get like a house and do founder house and do five or six and turn it also into a content business?" [laughs]

    9. JB

      So I was thinking of buying the Facebook house. It's actually not that expensive house, the actual house where Facebook started. And when I was starting DoNotPay, um, I, I didn't know it was the Facebook house. The first I found out it was the Facebook house is there's a bus of, um, tourists from Asia who would show up at the house, and it would be like Avenue of the Stars. Like, I guess grow- growing up, I would visit LA, and you'd like go on a bus with all the stars and, and this was like on the tour route. And this bus showed up of these tourists, and I said, "What are you here for?" And they said, "We're here to see Mark Zuckerberg's house." And I immediately thought, "I guess this is the content marketer in me. Um, you can come in, but you have to subscribe to DoNotPay." So w- we had a DoNotPay employee outside with a clipboard, and, um, to enter the house, you actually had to become a DoNotPay user

    10. HS

      [laughs] That is amazing. I'm just wondering, what are the limitations on expansion for you? The one bedroom was. Could it be three? Could it be six?

    11. JB

      That's such a LP question. Um, I think-

    12. HS

      [laughs] Thanks, Josh

    13. JB

      ... I, um, I think, um, you should start a fund of funds. You have amazing judgment. [laughs] Um, I, I think there's something special about one.

    14. HS

      Hmm.

    15. JB

      Um-

    16. HS

      How long are they in there for?

    17. JB

      As long as it takes. Hotel California, they can't check out until they're in a stable spot. Usually, that's a few weeks

    18. HS

      Usually a few weeks?

    19. JB

      Yeah

    20. HS

      Wow. Okay, and so you'll tee them up then for a round, and so you'll introduce them to-

    21. JB

      Maybe a traditional pre-seed or seed, yeah

    22. HS

      And so you'll introduce them to 10 to 15 VCs

    23. JB

      Yeah, and I will go very personally to do everything to help them. So oftentimes there's arbitrages. I'm moving them internationally. I'll put their O-1 genius visa on my credit card. I'll use all my social capital to introduce them to whoever it takes. Um, I ha- I had one person, um, he was building in data centers. I phoned up my old friend Jamie and introduced him to Jamie from FluidStack. The, um, do anything as, anything possible to kind of build up credibility, build their team, and get them in a stable spot

    24. HS

      I absolutely love that. It's, it's so rare to meet someone like that, and it's so rare to, to be able to do that 'cause most people run portfolios, and you just don't have that. Can I ask you a tough one, which is like, have you ever lost belief when you've seen them in the first few weeks?

    25. JB

      No, I, I, I, um, I've never lost belief in someone who stayed with me. I, I think there's enough filters before that. The opposite is true. I've, um, accosted them at 2:00 AM while they're sitting on my couch. I'm like, "I wanna put in another 300K." [laughs]

    26. HS

      [laughs]

    27. JB

      It's difficult to say no. [laughs]

    28. HS

      That, that... Yeah.

    29. JB

      Yeah

    30. HS

      You're, you're staying at my house.

  9. 43:08 – 45:51

    The 1000x Investment: What Joshua Saw in Ali Ansari

    1. JB

      No. The op- the opposite is true, actually. The, the crazier it is, um, the, um, the better they do. Um, so Ali Ansari is a Micro1. It was objectively my best-performing investment in terms of multiple. The founders get upset when I reveal exact valuation numbers, but let's say over 1,000X, well over 1,000X, um, and based on the, kind of the scale of the business. Um, and when I met him, he, um... I said, "I'll invest only on three conditions." So it was a California LLC, uninvestable. It has to be Delaware C Corp. Um, he was based in kind of Los Angeles as a solo founder, um, and he was running a kind of a staffing business, um, which there's a million staffing companies, even in the UK. And so I said, "You have to move to the Bay Area. You can live in my spare bedroom. Um, you can, um, you have to reincorporate in Delaware or, or shift to Delaware. Um, a- and, um, you have to use- do a software-style product. I don't mind what you do, but it can be anything." And we grinded, and he's the hardest, one of the hardest-working people I've ever seen. Um, and actually, um, he still lives in my building to this day, and I, like, come at 12:00 AM, and he's, like, working, like, um, middle of the night. And he did all those three things, and it changed everything.

    2. HS

      Dude, what did you see in him? I, I don't mean that rudely to Ali. He's... Or I've seen him actually introduce his... He's clearly brilliant now, but you learn and develop. Staffing business? How... I- I'm sorry to be rude. How uninteresting. As you said, there's millions of them living in a... What did you see in him that made you so convinced that he would pivot, change the company location, change his location?

    3. JB

      Never give up. Um, if you back someone who's above average IQ, very smart, um, and never give up, of course they'll succeed, and I think this is actually a mistake a lot of VCs are making. They are focusing too much on, on these credentials. So there's a race right now to back the math Olympiads. Um, VCs are, like, going to spelling bees and math competitions in high school. And I think IQ is very important. You need someone smart. But much more important is they'll never give up, and I could tell from my own journey and, and interviewing people for the Thiel Fellowship and seeing so many founders, that Ali was someone who would never give up, and he's, uh, he's, um, overcome huge challenges along the way to kind of build his business.

    4. HS

      Do you agree with Ken Griffin, who said on the weekend that he likes athletes with above average IQ?

    5. JB

      Yes. I, I, I would agree with that. Um, I, I think athlete- athletes is one form of never giving up, and, and you can kind of tell. A huge chip on your shoulder is another way.

  10. 45:51 – 46:59

    IQ Is Overrated

    1. JB

      There are so many.

    2. HS

      Totally agree. You, you... We said there about Micro1 and Ali. Take me to that then. Like, so he's in the house, and then he's going out to raise. You're introducing him to VCs. How was that first round?

    3. JB

      Once, once the minor things get sorted, um, it's, it's actually quite... There, there's so much money. People ask me, "Are you worried about competition from XYZ, uh, XYZ B- B5 seed firm?" I'm like, "No. That, that's, that's an... They're, they're helpful. They can kind of join these companies and g- and kind of, um, babysit them." And, and so once these minor things are sorted, it becomes legible fairly quickly, not for, like, a, a unicorn, but, um, certainly for an institutional seed.

    4. HS

      How much weight do you put on the idea, to your point on, like, Ali, where his-

    5. JB

      Yeah

    6. HS

      ... never give up in a staffing business? Awful. [laughs]

    7. JB

      So this is the biggest mistake I think I've made as an investor over the years, which is as a investor and entrepreneur, my imagination can run wild as to what they can build. I think if only they did this, it would be huge. Um, the problem with that is unless it comes from them, it's not their life's work, and so I'm very cautious.

  11. 46:59 – 1:03:07

    Never Tell Founders What to Build

    1. JB

      I, I have a rule. I never tell the entrepreneurs what to build, which, which might seem surprising, um, as an investor. I say to them, "It's your job to build the product and get customers. I can help with everything else." And so I never index too much about the idea. It's about the person. With that said, there's, um, a few things that I'll never touch. I'll never touch crypto. I'm not getting into whether I believe in crypto or not. I think it has huge use cases, but I think it's best left to the crypto funds. Um, consumer hardware is tough, um, y- because of var- various, various different consumer hardware issues. So I try and, uh, stay away from that, at least for my fund. But beyond that, anything.

    2. HS

      Totally-

    3. JB

      And wet science as well. I stay away from that.

    4. HS

      I agree with you. Uh, well, I would say kind of, uh, uh, for me it's a specific about biotech and life sciences, where it's like it's far too intellectual for me, and it's like Atlas exists for a reason. You should go and see them.

    5. JB

      Yeah. I'm not a scientist.

    6. HS

      Has what you need changed? I would say, again, the show is successful 'cause I'm very open. I would say we as a firm are struggling to make the transition between what was good, one to five million good enterprise clients, to what is expected now, which is, you know, Ligora, one to 100 million in 18 months. W- L- Lovable, one to 100 in 15 months. Has what you need to see changed?

    7. JB

      No. I'm more excited than ever. Uh, everyone is pitching this AI infrastructure nonsense, like we're building agent observability, like the jargon levels. I, I'm British. I, I think that's all BS. Like, they just add on the jargon. I love people building real businesses, so the more real it, it is, the better.

    8. HS

      What's real? Like...

    9. JB

      So... And I think-Enterprise AI is really exciting. Um, like Assured or Owner or, or, um, Micro1, things like that.

    10. HS

      And what you mean by that, just so I understand, is like I sell a product that people pay for, and it's a simple transaction in that way, not the market will move towards our way of seeing data access for agents.

    11. JB

      Yeah, and actually-

    12. HS

      But how do I detail-

    13. JB

      I, I, I mean-

    14. HS

      ... Joby?

    15. JB

      Yeah, I mean, if you can't explain the business to someone at the pub in the UK, like i- if you go to a pub and say, "I'm building observability for AI agents," they'll li- laugh at you. Like, but if you say, "I'm building like software to automate, um, health insurance claims," that makes sense.

    16. HS

      Yeah, I, I totally get that. When we go back to the Alis and the Micro1s for the fundraise, what do you advise founders when they get multiple term sheets and the heat is on?

    17. JB

      That there's kind of two groups of firms. There's like the kingmaker firms that you should accept at any price. Um, one example would be Founders Fund or Sequoia, uh, or people like that. Um, and so if you get an offer from them at X, and the offer from, um, someone else is at 2X, you should take their offer because even if you're maximizing, um, amount raised and minimizing dilution, in the long run, um, it, it, you're king-made, and it will save you in the next round. Um, so you should definitely go for wh- but the, the, another mistake these entrepreneurs make is they have the list of the kingmaker firms as too big. Um, there, there's probably like some tier two firm that think very highly of themselves that aren't in that same level as, as Founders Fund or Sequoia.

    18. HS

      No tier two firm thinks they're tier two, to be very clear. [laughs]

    19. JB

      [laughs] Yeah.

    20. HS

      Um, uh, can I ask, I'm not gonna ... Can I ask you if I were to put the pressure on and say you can have three firms in tier one and three only, what would they be?

    21. JB

      Oh, I, I, I, I, I-

    22. HS

      [laughs]

    23. JB

      No, it depends on the sector. Um, it, it really depends on the sector. Like if you're a consumer company, getting Forerunner could be the king- king-making thing. If ... Generally, it could be Founders Fund or Sequoia or, or something. So that's a very diplomatic answer.

    24. HS

      That's a very diplomatic answer. I often think that king-making exists, very candidly. Do you agree that king-making exists? You said it a couple of times.

    25. JB

      100%. We live in such a noisy world that people outsource their judgment to established brands.

    26. HS

      The thing I think you've also seen that people really don't anticipate is how king-making really correlates to customer adoption. And what I mean by that is if you look at, and you ask Winston at Harvey or Max at Lagora, a big part of their customer acquisition is relying on their venture investors to bring mega law firms. Like, it is a revenue generator.

    27. JB

      Yeah, and it's not just law firms. Um, even, um, consumers who use DoNotPay, um, I, I think I'm sure lots of people have signed up because of the investors that backed us.

    28. HS

      You mentioned the word dilution there.

    29. JB

      Mm-hmm.

    30. HS

      I'm seeing more and more fund, uh, founders, sorry, who are like, "Oh, I'm being very dilution sensitive with this round," and it's, it's often very early rounds.

  12. 1:03:07 – 1:05:29

    DoNotPay Pays Dividends

    1. HS

      Was there a moment where you were like, "We're not a traditional VC company, and I'm not gonna go down this route of, like, raise, raise, raise, headcount, rah, rah"?

    2. JB

      I think from the very beginning we were always f- w- I mean, the, the clue is in the name, like DoNotPay. We, we, it, we... I joke it's not just a company, it's a lifestyle. I'm like Mr. DoNotPay. Um, and, and so we would never want to do anything stupid. And when I was hiring my friends, um, I was always hiring the people who were, like, browsing Reddit at 2:00 AM trying to save money. Um, and so we're really in it for the DoNotPay, and so we, we never kind of, uh... I, I think, I think this is controversial. I think founders who burn all the money, I, I think that's not cool. I think it's kind of lame because why did they run out of money? Why didn't they just cut the burn? Um, and, uh, obviously some founders fail because of some, like, black swan event, and I can understand that. They take a massive swing, and there's, like, a ba- like some huge litigation or something, like a patent thing that Apple crushes them or something. That makes sense. But if they just run out of the money, that's not cool. That's kind of lame. They should have just managed their burn better.

    3. HS

      I totally agree with you. Um, okay. And so the dividends-

    4. JB

      Yeah

    5. HS

      ... how does that work? Basically we're so profitable-

    6. JB

      Yeah

    7. HS

      ... we just dividend out.

    8. JB

      So we have more money than we've raised, and we're actually doing another dividend next month, so it's, like, quarterly. Um, we're, we, yeah, we're planning on doing it now quarterly. Um, and, um, the investors, I think it works for us because the investors got in at such low prices. We, we never, we didn't raise 100 million. We could have at the peak of 2021.

    9. HS

      You raised 22.

    10. JB

      Yeah.

    11. HS

      Yeah.

    12. JB

      Which when I was, uh, fresh off the boat from the UK dropping out of college, that seemed like the world of money. But in the grand scheme of things, given the scale of our business, it's not actually that much money.

    13. HS

      Do you worry that to your VCs you're not a success? And I didn't mean that badly, but just, like, you know as well as I do, we look for fund returners. You're not gonna dividend your way to a fund return.

    14. JB

      I think that we are gonna take some big swings this year. Um, we are looking to kind of roll up some different consumer things within DoNotPay, and so we, we're still, I'm still 10 years in, ex- still extremely excited and ambitious, and who knows?

    15. HS

      You said there about hiring friends.

    16. JB

      Yeah.

    17. HS

      How do you advise founders on how to build the best first five

  13. 1:05:29 – 1:07:36

    Hire People Who Scale Themselves

    1. HS

      to 10 people?

    2. JB

      I think business school is actually a counter-signal. Um, I, I'm not gonna be very popular among the business school people, but, um-

    3. HS

      I agree 100%.

    4. JB

      Yeah.

    5. HS

      Um, my favorite is when it's, like, in the LinkedIn title though.

    6. JB

      Yeah.

    7. HS

      Yeah.

    8. JB

      So stay away from the strategy hires. Strategy is a meaningless hire because, um, what does that even mean? Everything is strategic. Um, I think connection to the problem is really important, similar to investing. Um, like DoNotPay employees, they, they're auto-scaling themselves. Um, like we had one DoNotPay employee, he would go to Target, the US, um, retailer, and he'd buy prepaid Visa gift cards so that whenever he would sign up for a treat, free trial, they wouldn't be linked to his direct debit real payment details. And we were like-

    9. HS

      And this was one of your products.

    10. JB

      Yeah. That would be like, that would make a great product. Um, so we're trying to b- hire people to scale themselves. Um, my very first hire at DoNotPay, obviously I built the thing myself. The design looked terrible. It, it gave me a headache. It was like a moving, uh, road background. Um, and you would look at it, and it'd give our early users headaches. We would give, uh, c- we'd get complaints. So people would get headaches from the design. So the first hire for me was a designer. So you need to, like, fill, like immediately solve these bottlenecks quickly.

    11. HS

      I absolutely love that. What role does not exist today that you think will be very commonplace within five years?

    12. JB

      Custom evals is, like, uh, um, e- ev- evals. So everyone is v- very excited about foundation models, like-Claude code and all, all of this stuff. But I think the future of AI will actually be organization-specific, specifically around the data that DoNotPay has, where we're u- doing evals on our own data. So I think custom eval hires will be really big.

    13. HS

      Do you worry about the concentration of value to very few numbers of companies? If you look at, at where markets think valuations will go and where companies will go, it looks more and more like eight companies will take $5 trillion plus of market cap, and actually could eat up large parts of the software market

  14. 1:07:36 – 1:09:26

    AI's Winners and Losers: The Giant Transfer of Wealth

    1. HS

      in some respects.

    2. JB

      I think there'll be a rise of, um, medium-sized businesses, like almost DoNotPays that fill the niche, and then these massive companies. But the, the middle, where there's just, like, a large company, I think they have to be very worried. I, I, I was saying to a friend, for every Anthropic employee who's making 20 to 100 million, there's 7,000 of, like, Block employees being laid off. Um, and, and so I think there is a, a huge transfer going on between the extremely large companies and the quite large companies. But I think the smaller ones will still have a role.

    3. HS

      Do you worry about what happens to San Francisco when you have, I think it was announced this morning, 600 OpenAI employees that took out an average of $11 million?

    4. JB

      I, I think there's a lot of pain happening in San Francisco at the same time. I think a lot of Meta employees are being laid off, a lot of big tech employees are being laid off. Um, I think there's, like, two types of goods. There's, like, absolute goods, like a standard apartment or some food and things like that, and I think the, the price of that will stay the same. But then there's, like, positional goods. There's only, like, eight seats in Delta first class. There's only eight houses, uh, where they wanna buy, like, uh, on the best road in San Francisco, and the positional goods will just go off the charts. So if you're someone who values your success in life by attaining positional goods, like one of the eight houses that everyone wants to be in, good luck.

    5. HS

      You... I, I spoke to so many of the founders that you work with. Um, most of them said about buying land as something that we should talk about-

    6. JB

      Yeah

    7. HS

      ... which I was not expecting by any... I when the first... When I think Dan should... Graptal said it. We were talking, I was like, "What?" Uh, 'cause I type, I write, take notes. And I was like, "What? Buy, he buys land?"

    8. JB

      Yeah.

    9. HS

      Why do you buy

  15. 1:09:26 – 1:35:03

    Why Joshua Buys Land With Every Dollar He Makes

    1. HS

      land, Josh?

    2. JB

      Um, so, um, in terms of, like, my diversification retirement, um, I take all the money I make, and I buy land. Um, I don't put it in the stock market. Um, I don't, um, buy... I don't keep it in cash because I think the dollar is, it doesn't have a good future. I don't buy bonds or anything like that, and I buy land. Um, it could be being British. Uh, there's a famous quote from Winston Churchill, "Land is the only scarce resource." And I think I'm diversifying on two outcomes. The first outcome is that AI creates, like, a, um, post-economic world where it replaces all big companies, and the only thing that's, that's scarce that's left is land. And so AI doing extremely well, land can still be valuable. And then the second is maybe, maybe it's all a bubble and all of tech goes to zero, but land will still be valuable. And the land I buy is, uh, in Nevada, um, far away from the tech bubble, um, and, um, it has, like, nail salons and all sorts of things. So it's passive, um, investment, and, um, it's just diversification for, like, the AI, the various outcomes that will happen with AI.

    3. HS

      Why Nevada?

    4. JB

      Um, I think there's, like, secular trends regarding it being very, uh, pro-business, um, and population growth. Um, in fact, there's only... Three things are true in Nevada. Um, there's no state income tax, there's very low property tax, um, and, um, it has a rising population. Um, and that is not true, in my opinion, anywhere else in the US. Um, so if you compare it to Florida, for example, there is no state income tax, but very high pl- property tax.

    5. HS

      Hmm. Do you worry about the rising hatred towards the super-rich in the US?

    6. JB

      I think that it's, it's not sustainable. You can't have 50,000 people with all the money. I, I think actually there could be a revolution in our lifetime. Something has to change.

    7. HS

      It's my biggest worry, actually, today. You see it in the UK too. We all sit here in the bubble of London.

    8. JB

      Yeah.

    9. HS

      You know, 33% of children stay in the UK grow up in poverty. It's an astonishing fact. What, what, what do you think happens in that respect? Is that just social revolution and unrest? I mean...

    10. JB

      I'm an optimist. I think that, um, the jobs that will exist in 20 years, we couldn't even imagine what jobs would exist. Um, like AI data cleaning, like these companies like Mercora, Micro1, those jobs didn't even exist five years ago, five years ago. And I think similarly, AI will create a huge number of jobs, maybe, um, working in air conditioning in data centers and all of that stuff. Um, the problem is there'll be a shift in the economy, and people will have to transition, and I think the government will have to get a lot better at helping people transition.

    11. HS

      Has Trump been better for business for you?

    12. JB

      Absolutely. I, I, I think that whether you agree or disagree with what's going on right now, um, it's objective that for tech, um, the current administration is a lot better. Um, Lina Khan, in my view is, is evil. Um, several companies I invested in had their acquisitions blocked by, by the kind of Lina Khan style, uh, approach. Um, and the, the worst kind of Lina Khan story I heard is there's, like, a, a biotech company that, um, was being acquired by a, a much larger kind of pharmaceutical company, and Lina Khan's FTC blocked the acquisition. And to this day... And the drug didn't get developed, and to this day, 50 people die a year because, because of the acquisition being blocked. So I actually think that, um, the, the kind of tech policies of the last administration were not very good.

    13. HS

      You said the dollar d- maybe doesn't have the good future. [laughs] I think, I think I, I put a lot of my money in dollars. Why, why not? And sh- why should I think differently?

    14. JB

      I think that, um, inflation every year is just going crazy, and it's just going to get worse. Um, I mean, house prices in SF seem to be doubling. Um, th- things are not what they used to be. Um, and the only way to stay ahead in this AI world is, is to have real assets.

    15. HS

      When you look at real assets, so like what, what is your IRR on like a, or return profile on a land in Nevada, genuinely?

    16. JB

      It's, it's only like 10 to 20%, um, but, um, it is very safe.

    17. HS

      That's better than I thought. Like, for real estate, that's not bad.

    18. JB

      Yeah.

    19. HS

      Like on a stock portfolio, in a good case you're like 15%. Good case.

    20. JB

      There's all sorts of advantages, like you don't have to... Ah, you can... There's depreciation and things like that.

    21. HS

      That's absolutely wild.

    22. JB

      Depreciation doesn't exist in the UK.

    23. HS

      Is there anything else you do weird with your money?

    24. JB

      No, that's it, and I just set it and forget it with the land.

    25. HS

      We, we mentioned like the pain of big tech, and it's sad to see the layoffs. W- was that in your mind just mass over-hiring from COVID interest rate times, or was that actually AI causing efficiencies?

    26. JB

      I think it depends on the company. With Meta, I think it's AI driven. Um, they're-- it's clear that they're spending so much money on their data centers, and AI has made their engineering more productive. They need fewer engineers. But maybe with a company like Block, um, maybe it's controversial, but I think it's more about the COVID over-hiring.

    27. HS

      Do you buy that we will have dramatically smaller companies in the future?

    28. JB

      Absolutely. Um, I, I think that i-i-it's objective. Y-you, you don't need... I mean, even with DoNotPay customer support, uh, we're seeing optimizations. Previously, you had to hire like three people to do the job of one person. Now, now, um, so we do have like 10 extra, like, contractors for customer support. We, we found that maybe even that, that's too many. Now they press a button, and an agent kind of identifies the issue and pre-processes the refund, for example.

    29. HS

      What do you think of competitive markets? You mentioned customer support there.

    30. JB

      Yeah.

Episode duration: 1:35:14

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