All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

Today's show: It's another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover. Together they're going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone's different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more! It's an essential watch for anyone building or investing in companies in 2025! Timestamps: (0:00) Introducing our amazing investor panel! (03:15) The panel shares their First Fund experiences (10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www. Squarespace.com/TWIST (11:27) Show cont… (12:46) Where we're at on the investor Greed-Fear Index (13:54) The delicate art of investor discipline (20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (21:59) Sophia's criteria for a follow-on investment (24:17) Founders are going direct on social media (29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist. (30:49) Show cont… (32:33) Why we're seeing so many more Series Bs (33:30) So when do you trim a position? (39:35) There are SO MANY COMPANIES! Why surface area matters. (43:25) Durable vs. brittle revenue and how to tell them apart (46:15) When it's time to angel invest outside your fund (49:04) The panel's approaches to capital recycling (57:15) The benefits of co-working "jam sessions" Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: (10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www. Squarespace.com/TWIST (20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist. DISCLAIMER *All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC. Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use. Rate as of 7/18/25. APY is variable and subject to change. Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jason Calacanis?

  That is then determined by your deal flow. Do you actually have three other bets that are better or as good? And that's really the, I think, the art of the discipline here is knowing when to use four bullets to hit the target versus, you know, just pay. And we have this happen all the time. And the way I've now taught my team to do it, because we now have 11 people on the investment team, is I've taught these young folks to say, okay, in our accelerator, we're investing at a $1.7 million valuation, right? So in order to own 7% of that, of that $10 million company, I've spent 700K. Okay, would you rather make 525K bets? Six, five, 525K bets?

• 0:44Jason Calacanis?

  Or own 7% of this one at $10 million? And compare it, this is a very easy way to do it. Look at the accelerator class that just graduated with 12 startups. Is this, where would this company rank in there, in that group? If it ranks number one, or it's like by far number one, it's better than all 12, okay, you got a case to make. If it ranks number five or six of those 12, well then, why are we doing that?

• 1:11Speaker 01

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• 1:54Speaker 01

  Learn more at public.com/twist. Hey, welcome back to TWIST, This Week in Startups. My name is Alex and we have an investor panel for you today, including our homegrown champion, Jason Calacanis, from both Founder University and the Launch Accelerator. And then we have Ryan Hoover, best known for tweets, cat pictures, and the fact that he is a founder over at The Weekend Fund. And then we have Sophia Amoruso from Trust Fund over in the UK. Sophia, Ryan, Jason, how are we all doing?

• 2:21Jason Calacanis?

  I'm in Park City and really excited to see you, Sophia and Ryan. It's been too long. Ryan? Such an amazing founder. He did Product Hunt. Still, I mean, founders today, Ryan, still, my portfolio companies. Will you share us on Product Hunt? I mean, you built something that less. That's got to feel pretty good, huh?

• 2:41Speaker 02

  It's been almost 12 years, which is insane. I'm starting to feel really old. I don't know. When I was, when I was 25, you know, talking to all these, in my eyes, 35 old men, you know, VCs, I was like, wow, these guys are kind of old. Now I'm 38. I'm one of those guys.

• 2:55Jason Calacanis?

  Yeah, yeah, it happens quick.

• 2:59Speaker 01

  And the Weekend Fund is on its third fund, Ryan, I believe?

• 3:03Speaker 02

  Yep, that's right.

• 3:04Speaker 01

  Yeah. And then Sophia, your venture capital fund trust fund is still on its first fund, according to filings that I could find.

• 3:10Speaker 03

  That is correct. Yep.

• 3:12Speaker 01

  And Jason, you're on launch four, I think?

• 3:15Jason Calacanis?

  Yeah, I'm on a fourth fund. And then arguably, I'd say it's really our fifth because my angel list portfolio and my Sequoia Scouts portfolio kind of predate that. And that was, would have been like Fund Zero. So probably Fund Four is the official fund name, but it might be Fund Five. And I've got to make a decision in the next year. Do I do Fund Five? Or do I retire? Or do I just work for my own balance sheet, which is what happens to a lot of funds. I think Homebrew decided to go off their own balance sheet, I think. I don't know if we've seen this a couple of times, but sometimes you get to the point where you're like, the process of raising money from LPs takes so much time, is so painful, requires so much communication post,

• 4:00Jason Calacanis?

  that if you have the ability to just work from your own balance sheet, you just eliminate, I don't know. What does it take you, Sophia, in your first fund to raise money and communicate with your LPs versus actually doing the job of finding and investing in companies? In year one percentage?

• 4:18Speaker 03

  Year one, I was like, yeah, I would say 20% of the time was talking to, you know, founders and the rest of it was fundraising. The fundraising didn't take too long. I think I spent a lot more time with funds and funds and institutional investors who weren't right for the size fund that, you know, that I was building or for Fund One. So I could have done it more quickly if I had just focused on individuals and people that I knew and the people who made up, ultimately made up my LP base, including you, and people like Markin, Drayson, and Hot Shots, David Sacks, your buddy.

• 4:55Speaker 02

  Got to collect them all. Got to get all the besties for the next one.

• 4:57Speaker 03

  All of them.

• 4:58Jason Calacanis?

  It's happened a couple of times.

• 4:59Speaker 03

  I can continue.

• 5:00Jason Calacanis?

  Yeah, we have, I don't know if there's a fund with all four, but my friend Sandeep Madra, who's now sold his company to Grok, all four of us were investors in his last company and the company before that. But that's more of a poker table thing. He always, when he would raise money, would just at the poker table, say, I have a 200, like last time was like, I have a 250K allocation for besties, you know, first come, first served, whatever. And I was like, yeah, no, that's great. But, you know, I'm going to provide a little more value. So I think a 750K, but nobody needs to know, whatever. And he's like, yep, every single person said the same thing. You're all just at 250.

• 5:34Speaker 03

  He invested in the fund. He invested in trust fund because we were a poker table.

• 5:38Jason Calacanis?

  I told him to.

• 5:38Speaker 03

  And you were like, you're investing, you're investing. He was like, okay, 50K. I was like, yeah, that was easy.

• 5:44Jason Calacanis?

  A little peer pressure. I was like, we gotta, we gotta get the ball rolling here for Sophia.

• 5:49Speaker 03

  Honestly, like, I raised a lot of money at the poker table, like, not just your, you know, poker table, but sitting around, getting to know people, people, you know, you talk to people, you, you know, and then there's other people there who might vouch for you and be like, oh, yeah, something about this person, you know, Anthony Noto from SoFi played, you know, poker with at the, you know, code conference. And poker's just, you know, I'm telling you, Ryan, Alex.

• 6:13Jason Calacanis?

  It's the new golf. You get to know people.

• 6:14Speaker 03

  Yeah.

• 6:15Jason Calacanis?

  You know, it kind of works. Ryan, you had an incredible advantage. And that was, by the way, the last time I hosted my, Sky Dayton, myself and Brooke Hammerling would host a poker game at the code conference. That was the last code conference, the last time I hosted the poker game there, because Kara Swisher kind of hated me, I guess, at the end and, you know, hated Saks and hated tech, tech people, entrepreneurs, the whole day. So it was like, it just became untenable because we would have some of the press there. But the press hated the CEOs and the VCs. So every year, for 15 years, 20 years of

• 6:55Jason Calacanis?

  doing it, I just watched as like, the animosity between the two groups grew to the point at which I was like, why am I putting these two groups of people who hate each other in the same room? And then I was like, fuck it. I'm just taking the best one, Alex, for myself. I'm I'm taking him out of the journalism ghetto and I'm taking him for my side.

• 7:15Speaker 01

  I was just thinking that if you really want to have people who don't get along, the poker table is the best place to do it because it's the only place where it's socially acceptable to lie and steal from one another.

• 7:24Jason Calacanis?

  Yeah.

• 7:24Speaker 01

  Within the rules of the game. It's perfect.

• 7:27Jason Calacanis?

  Ryan, you had a big advantage with your first fund, I think, because you were had sold to Angelist at that time or you were doing a syndicate or something, maybe.

• 7:35Speaker 01

  Yeah.

• 7:35Jason Calacanis?

  How's it going for you raising funds and that part of the business? I'm curious.

• 7:39Speaker 02

  Yeah, I mean, well, the first fund, it was right after shortly after Product Hunt sold to Angelist. I stayed on as CEO for four years afterwards, but raised the first fund and my goal was a million dollars. I was like, I'm going to raise a million. I'm going to try to raise a million dollar fund. That grew to three million. So like way oversubscribed, massive fund, three million. And, uh, and yeah, being in the flow and, you know, a lot of my like former investors who, you know, backed me and the team at Product Hunt were LPs and still are. So yeah, some advantages there for sure. And then honestly, it's, we'll see how the market is. We're not raising now, but we will, you know, in the future and it's changed a lot. This last, the current fund that we're in right now was, was raised in 21 and we all know, you know, 2021 was, was a very bullish time.

• 8:22Speaker 02

  Uh, and it was, to be honest, not that difficult to raise, relatively speaking to what I've heard from other GP, especially like emerging managers right now. So, uh, we'll see.

• 8:31Jason Calacanis?

  You snuck in the window because when Silicon Valley Bank blew up and Lina Khan took the reins, that was the end of the, uh, the end of the innocence. Like it was so enthusiastic and then there was just four years of complete depression, which Sophia, you got to raise during.

• 8:48Speaker 03

  Yeah. I mean, I was raising at a time when, you know, it was 2023, when I was like a couple of years old. And I think that everybody was talking about the bloodbath of the, of the managers who had raised during 2021 and that they've invested in these companies with these wild valuations and that, you know, I was in a period where there was a correction, but also there was a, what do you call it? When, um, You know, funds hadn't marked down their private, you know, they were over allocated on venture. You know, it was a weird time where the market had dropped, but you know, funds hadn't marked down their portfolios.

• 9:30Speaker 03

  So, but yeah, I'm glad I didn't raise in 2021 because I also know, just speaking to fund managers who raised their first funds in 2021, they weren't getting the hard questions that I was getting.

• 9:45Speaker 03

  Because it was, it was much, you know, easier to raise. And so I feel like it not being the easiest or raising in a different environment forced me to learn how to answer questions that, from what I've been told, some emerging managers didn't have to because of the environment at the time.

• 10:04Jason Calacanis?

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• 10:48Jason Calacanis?

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• 11:28Jason Calacanis?

  Yeah, mark to market, putting your marks, I guess, is the term you were looking for, Sophia. People use all different terms for it.

• 11:35Speaker 01

  I want to go back to micro funds, though, because this is interesting. Ryan, you sent over some data from Angel List that said essentially emerging managers, smaller venture capital funds are having a much better time through Q2 fundraising than they were Q1, Q4 of last year, et cetera. So it seems that there's been a bit of a resurgence in LP interest in smaller venture capital funds. And I'm just curious, Ryan, have you noticed that shift amongst your own LP base? And is that going to change your fundraising schedule, bringing it up, perhaps?

• 12:01Speaker 02

  I'll have a much better perspective when we start raising, because that's when you actually really know, are people actually going to invest? They often like reach out and say, hey, are you raising? We get those emails, I'm sure Sophia, you get those emails all the time. But you never know until they actually write the check. But yeah, I'm in touch with Avalok and the Angel List team. And they reported between Q1 and Q2 this year, 43% increase in LP capital into the Angel List platform, which is sort of an index of a number of funds, maybe skewed a little bit slightly towards like syndicates, SPVs and smaller funds. But that's a huge, huge increase. And, you know, part of it, my theory is we're seeing a lot of optimism around AI, of course. We're seeing, you know, Figma being like the, you know, one IPO that's going out that hopefully will inspire more liquidity in our ecosystem.

• 12:46Speaker 02

  And so I think we may see a rebound, who knows? So I'm not going to try and predict the macro. And at the end of the day, I'm just, you know, continuing to invest.

• 12:54Jason Calacanis?

  I'll predict the macro. Yeah, you know, there's like a greed fear index and we're now deep in the greed index. And I think we were from Silicon Valley Bank blowing up, Trump presidency, Kamala presidency. Both of those, I think, were big unknown scaries for people. Like, is it going to be, is it going to be like Trump has gone wild? Is it going to be Kamala's raising tax rate, you know, raising more taxes? And, you know, could be actual chaos. So uncertainty of the past two years, combined with

• 13:31Jason Calacanis?

  You know, no optimism and no distributions, I think led everybody to be at greed. I would say, yeah, it's interesting. It came up as a 69 there. I was going to put it at 420. But I think we're

• 13:44Speaker 01

  I didn't know you were pricing Tesla robot taxi rides.

• 13:46Jason Calacanis?

  Wait, your birthday's 420, Sylvia?

• 13:48Speaker 03

  Yeah, all my friends ditched school on my birthday. It was so lonely.

• 13:53Jason Calacanis?

  It all makes sense now. So I think we're, we're heading into a greed cycle. Where people are starting to have FOMO and greed again. I missed out on this round. I don't own SpaceX. I don't own Stripe. I don't own Android. How do I get those? Oh my God, humane robots is the next big thing, but they have no revenue. But they're doing an SPV at, what was that, 30 or 40 billion? They may have a customer BMW, but BMW said they're not really using it in production, but maybe they are using it in production. Like all of that are the signals to me that greed is trumping fear.

• 14:33Jason Calacanis?

  And that's good until people lack discipline in their entry prices for, you know, people in our line of work, seed and pre-seed. Which is where you get yourself in a ton of trouble. So anyway, good time to be playing the game. And the distributions are going to make people frisky. When that Figma goes out. With Circle going out, CoreWeave going out, I think we're just going to see tons of money start to recycle, recirculate, recycle. All of those things. Doesn't surprise me. Angelus is the tip of the spear.

• 15:05Speaker 02

  Yeah, evaluations are also up. They, Avolco is sharing some numbers. Pre-seed is flat, according to them. Seed is up 15%. Series A is up almost 10%. Series Bs are up 40%. Now, maybe that's a smaller sample. You know, hard to, hard to measure the macro, the full macro on that, but valuations are high. It's a lot different when I started Weekend Fund. Average entry price, I think, was like six and a half mil post.

• 15:27Speaker 01

  Is that a pre-seed or a seed number, Ryan?

• 15:29Speaker 02

  That was over the entire fund. So combination of seed and, and pre-seed. And that was like the median, I believe. So yeah, much, much lower than what we're seeing right now in the market.

• 15:40Speaker 03

  Ryan, what valuation and stage do you target? Like what's your, you know, I've heard funds that like, we don't invest past 15 million post and it's like, There's a lot that you're going to miss, right? But discipline's important as a fund manager. It was so much more fun as an angel, being able to invest at like any stage. But it's one thing that I know LPs will evaluate our funds by is how much we stuck to what it was that we said our fund construction was going to be when we talked to them the first time.

• 16:08Speaker 02

  Yeah, I mean, I constantly question myself on this. We do have some price awareness, not maybe sensitivity is maybe not the right word, but awareness. We do pass on deals sometimes when the valuation seems extremely high and it's like pre-launch and there's not a lot of like objective proof points. But at the same time, we're also hit to kind of play the game, play the ball. What's the metaphor? Play the field? Play the game on the field? Play the game on the field, yeah. And we obviously don't want to miss out on the best company. So we're reevaluating a lot of that right now, actually, and thinking through even our strategy in the next fund and how we deploy capital. Historically, we've written about 300K average check size. Our goal is to have every company, you know, if it's a unicorn or above, like could return the fund. But the reality is the valuations are getting much higher.

• 16:54Speaker 02

  Also, the optimistic approach is, hey, what is a billion dollars? Like today's billion unicorn is tomorrow's 10 billion, you know, decacorn. These companies are getting big very quick. And if you look at just how, I mean, I hate to say AI, but AI is also eating into more of the market. It's going to eat into services in terms of like the GDP of the world. And so you can actually see some of these companies that used to be unicorns be much bigger today. So.

• 17:19Jason Calacanis?

  That's an interesting point, Ryan, because it's almost the snake's eating its tail. If we succeed with these AI companies, then we lower the revenue and here we go. That could be problematic. It's, I think about it in like how many bullets you have in the gun, right? And sometimes you're like, well, this is a really good target. I'm willing to take three shots at it, which is like triple the valuation. And so I too, when I organize our fund, hey, we're going to have 300 names in this $45 million fund. Our average ownership is going to be 6%. Add a 6% average ownership, get diluted to 3%. We need approximately a unicorn in the $1.5 billion space to return the fund.

• 18:01Jason Calacanis?

  Every investment has to have the potential to be a unicorn, or why are we making the investment? Which means it has to have a great team, you know, good product velocity and going after a big market.

• 18:14Jason Calacanis?

  And so then you have to ask yourself, is this worth, you know, if I'm paying instead of 6 million, if that's your average valuation, okay, there's a 24 million, okay, am I better off making this one bet or making four bets? And that is then determined by your deal flow. Do you actually have three other bets that are better or as good? And that's really the, I think, the art of the discipline here is knowing when to use four bullets to hit the target versus, you know, just pay. And we have this happen all the time. And the way I've now taught my team to do it, because we now have 11 people on the investment team, is I've taught these young folks to say, okay, in our accelerator, we're investing at a $1.7 million valuation, right?

• 18:59Jason Calacanis?

  So in order to own 7% of that, of that $10 million company, I've spent 700K. Okay, would you rather make 525K bets, six, five, 525K bets, or own 7% of this one at 10 million? And compare it, this is a very easy way to do it. Look at the accelerator class that just graduated with 12 startups. Is this, where would this company rank in there, in that group? If it ranks number one, or it's like by far number one, it's better than all 12, okay, you got a case to make. If it ranks number five or six of those 12, well then, why are we doing that? Instead of doing another accelerator class, because we have so many people who want to come to accelerate.

• 19:41Jason Calacanis?

  Now that is, that assumes you have an accelerator people want to go to and that are high quality enough. So this is the thinking on everybody's mind, exactly what you're going through, Ryan. And Sophia, you're going to have how many names in your fund? Where did you wind up at?

• 19:56Speaker 03

  Probably like 22. I'm at 14.

• 19:58Jason Calacanis?

  Okay, wow.

• 19:59Speaker 03

  More concentrated than I had anticipated, but I've also done some follow-ons with some of the companies that I really, really believe in. And it's just much easier to, like, you know, throw my weight around for the guys that are going to like knock it out of the park than... I think continuing investing in companies that are gonna still need a lot from me, but you know, I have less, you know, I have less data to operate on. So I'm curious about, you know, I didn't, everybody in these, you know, with these like micro funds of like no reserves, no reserves, but I'm also like, you know, just, I think math aside, logic tells me to double down on a winner, right? Like, I think just everybody like believes

• 20:42Speaker 03

  in that you give an employee a promotion, whatever that is, you know?

• 20:48Jason Calacanis?

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• 21:30Jason Calacanis?

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• 22:00Speaker 01

  Sophia, what are your criteria for making a follow-on investment? What's the standout thing you're seeing in those companies that makes you want to deploy more capital into them? Is it revenue velocity, product velocity?

• 22:10Speaker 03

  Revenue traction, speed of development. So, you know, two of the pre-seed, I invested in two pre-seed companies of the 14. And both of those guys went on to raise really big seed rounds. And I think when, it hasn't been very long since I've spoken to the founder, but the product has moved so quickly that I need to touch base with them to ask how to describe it next time I talk to somebody or when I'm going on a podcast. I think that's a really good signal. And, you know, it's like Nectar Social, for example, like these, it's two sisters. They're ex-meta, one's an ex-meta, ex-product folks. And they live in Seattle.

• 22:55Speaker 03

  And it had been, I don't know how long, maybe six months from the time they raised with just a deck. And, you know, Ms. Bud, the co-founder, came over to my house and showed me this product. And I was like, holy shit, like, this is something I wish I had, you know, at Nasty. Yeah, this is something, you know, every brand needs. And now it's like, you know, they're working with Olly Pop and Jones Road Beauty. They just signed on Goop, like, they've got like real revenue. And the product is like, I use the product for my social media. It's like, you know, it's for brands, but I use it for, for certain like AI kind of automation and stuff. And, you know, I was, my mind was just really blown in what I think founders are, you know, are able to do now with AI, you know, punching above their weight, being able to use these tools and have teeny tiny little teams is really encouraging.

• 23:39Speaker 03

  So also the founders who are, you know, taking advantage of that and either scaling down or staying small as they go from pre-seed to seed is something.

• 23:49Speaker 01

  So we've talked about revenue growth and also how fast they're shipping and also these team sizes. I feel like we're really circling this that he describes as the new status symbols in Silicon Valley. And if you're on the audio version, it's, it says that raising is now revenue, press is now social reach, credentials is now shipping and big teams are now small teams. Jason and I talked a lot about the set of team size thing. But Ryan, it sounds like Sophia and you are in pretty close agreement about what's changed in the startup game.

• 24:18Speaker 02

  Yeah, I mean, it's you're seeing a lot more people showing off their revenue numbers on Twitter. And it's creating, I mean, I'm not gonna lie, like sometimes some FOMO, I'm like, oh shit, like, I didn't even see this company. Oh, my gosh, they're making like 50 million in revenue in the first 12 months. Like, this is insane. And so you're seeing a shift in how people are pumping their chest, whether we like it or not, like, revenue is the new status symbol beyond just raising. Now, raising still matters. Like, if you get a brand name firm backing you, that still matters, but that's secondary to revenue at this point. And also, it's a leading indicator into getting those funds, obviously, interested in what you're building. You also see a massive shift, of course, in the past decade from like press to social. And in many ways, like Twitter's become the new launchpad in many cases, partially because the algorithm

• 25:00Speaker 02

  makes changes. If you think about it, like, before, if you were a no name founder, you probably had, most people don't have a large social following. You put something on Twitter, you don't get a lot of play. Now you have an algorithm, it heavily incentivizes videos for like demos. And, you know, this is changing a lot of how founders are sort of playing the status game and showing off what they're building and what they've achieved. And so it's very different than when I, you know, moved to San Francisco in 2010 today.

• 25:28Jason Calacanis?

  Signaling is like, go ahead, no, go ahead, Sophia.

• 25:31Speaker 03

  No, is it okay if I ask questions?

• 25:33Jason Calacanis?

  You are, that makes it a dynamic discussion, yeah.

• 25:35Speaker 03

  I'm not the host.

• 25:36Jason Calacanis?

  No, no, that's when it's at its best.

• 25:37Speaker 03

  I'm just so, I'm exhausted. I don't even make that much content, and I'm fried. Like,

• 25:42Jason Calacanis?

  You make a lot of content. What are you talking about? You are

• 25:45Speaker 03

  Not like you.

• 25:46Jason Calacanis?

  Three, four stories a day. We just make different things. I make four podcasts a week. You make, what, three or four social clips a day?

• 25:54Speaker 03

  No, I don't, I mean, stories are just so lazy. But like, you know, sure startups have to like, create content, maybe, maybe not. But fund managers, like, some of these guys have like, massive TikTok presences and, you know, they're, I just like, I feel like the older I get, the less capacity I have, like, in general, to just do anything. And I don't know if that's like, brain fog, or like, hormones, or laziness, or perspective, or, you know, work-life balance, which I don't, like, that's not something I think a lot about. But,

• 26:26Jason Calacanis?

  That's a big statement from you, because your advantage, your unfair advantage, is your massive social media following. And that's what draws in a lot of founders, and that you're high profile. But, you know, there's something very interesting in the signaling, Ryan, that I think you pointed out, which is, the For You page means you could be a nobody. And the algorithm will put you in front of the somebodies. That's distinctly different than being like a reply guy and trying to like be in Keith Reboi's replies. You put out a great video, you put your revenue numbers, it trends. Keith Reboi sees it, Sophia sees it, you see it, I see it, Alex sees it. Or people put out like the Clue Lee video or the response video to it, like all that stuff, you just wind up seeing it.

• 27:11Jason Calacanis?

  So now you're aware of it and it's part of the overall trend. I would say there's like two trends here. Going direct and then the for you page surfacing nobodies. You know, like outsiders being able to get in front of insiders. Those are actually two very interesting things we've surfaced here. But I like the idea that signaling is changing and that people are looking for, you know, if you have revenue and then the next thing will be profits. So you will see, I'm starting to see some founders.

• 27:41Speaker 02

  Profits? We don't care about profits. We just.

• 27:44Jason Calacanis?

  I've had two founders this week when they sent their note, say, we have 24% margins right now. Two different ones. One's a media business and the other one is like a SaaS business. And they were like, I'm like, we're reporting on profits now. I'm like, how are you deploying the profits? We're paying taxes this year or are we investing in that, you know, in something because that's what we want to do. But signaling is super critical for founders to understand and for investors to understand because it kind of creates a shared dialogue. What you were talking about before about like the product velocity, Sophia. I like to come up with terms and the term we use internally. So we actually have our own vernacular is product velocity. When we see a founder with product velocity, that means something.

• 28:29Jason Calacanis?

  And then we have a specific criteria for follow on investments to Alex's original really good question. The other thing you didn't mention, but by name, but that you insinuated was, hey, they raised money. And then I saw that that company, Nectar Social, had raised money from True Ventures and Google Ventures. Our criteria is revenue growth, lead investor joining the board, and the track record of that lead investor. And so if we're going to follow on, if you have three, four, or five X revenue growth, we're following on, like, that's rare. And if you have a lead investor who I know, or we know, who's notable, who's invested in a great company before, how did you convince them?

• 29:12Jason Calacanis?

  Now, there's two possibilities. Either your company's great, and they recognize that and decided to lead it and join the board. So joining the board is a subset of that criteria, because a drive-by 250K check from a large fund, not really good. So in that case, I'm guessing True Ventures is either joining the fund or put in more than 250, 500K.

• 29:37Jason Calacanis?

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• 30:49Speaker 03

  Yeah, they co-led, they co-led the...

• 30:53Jason Calacanis?

  And is one of them joining the board?

• 30:54Speaker 03

  Yeah, I think Tony did it. Frederick may have. But like, you know, as a first time, you know, fund manager to be like, you know, there was like some random Texas firm had leaned in and wanted to preempt something. And I was like, guys, who are you talking? They don't have relationships in the valley. And I was like, you guys should talk to like the big boys. Let me introduce you to Frederick and Tony. And then I introduced them to one other top tier firm. That's like a dream firm. And, you know, both, all of them wanted to lead. And GV and True were basically like, okay, we'll co-lead. We're not going to get, you know, the 20% allocation that we want, but we'll each get 10%. And it was like, they just showed up and were like, who are these freaks? What is this? This is so amazing. That was it. It was just like on the merit of what they had built.

• 31:38Speaker 03

  And it wasn't, yeah, their relationships or anything. I certainly can't convince anybody to invest. It's not like, I don't have that kind of influence to be like, ooh, you know, but for me to be like, I don't, I don't know what I'm, you know, I haven't invested in that many pre-seed companies even as an angel, but to be able to send it up to tree and have like, you know,

• 31:56Jason Calacanis?

  Well, the fact that people will, the massive advantage you do have and the value you're providing to those is you validated them with your time and skin in the game. So therefore, when Tony looks at it, he says, well, Sofia's got 22 bullets in her fund. I heard this week in startups, she used one of her 22 bullets. That actually, skin in the game means something. And I think that's a massive advantage that pre-seed funds provide to seed funds or seed funds provide to Series A. And that's kind of what makes the ecosystem work. The other notable thing, I don't know if we have more data to bring this, to re-ground this, Alex, but the other thing you mentioned, the Series Bs were massively up.

• 32:39Jason Calacanis?

  This makes sense to me, Ryan, because you have so many of these mega funds with billions of dollars. And for them, they have to put more money to work. And, you know, that is going to lead to valuation increases. So then that leads us to the discussion. We had a company this week, we invested in two years ago, kind of maybe a, call it a $15 million valuation. Two, three years later, maybe three years later, they're at a $500 million valuation. Do we sell 20% of our ownership and send distributions? Since that investment is now theoretically 30x, that would be 32x. Do we trim 10, 20%?

• 33:25Jason Calacanis?

  Or do we take our pro rata or do we do both syndicate our pro rata? What do you think, Ryan? How do you think about when you trim a position? Because distributions are rare and the opportunity to distribute is rare. What's your current philosophy on that?

• 33:40Speaker 02

  Yeah, we so we've done this once. We did this about 18 months ago. We invested in the seed round of deal in the first fund and that was a 10 mil post. It's gone on, you know, I think the last round was on $12 billion valuation. And 18 months ago, we're like, well, okay, we have an opportunity to sell 14% of our our position to return the fund.

• 33:59Jason Calacanis?

  And that's a 400x return roughly?

• 34:02Speaker 02

  Yeah, yeah, it's like 10x fund returner on paper. And, you know, we'll see, it doesn't count until it's true DPI. But we're like, well, let's let's get one DPI, one x DPI.

• 34:11Jason Calacanis?

  The spy thing isn't going to sink your DPI. You'll be okay.

• 34:14Speaker 02

  Yeah, yeah, we'll see. No, it's I'm bullish. I'm bullish on the company. I was bullish back then, I'm bullish now. And granted, we did sell lower than the $12 billion number back then because this is also when the market was also in the the slumps a little bit. But the thought was, okay, one, our LPs, they've been, you know, they're going to be so happy to see some liquidity. No one's getting liquidity like 18 months ago. Two, we're still going to have 84%, 83% of our position remaining. So even if we make a mistake and it, you know, 10x is from here, we're still good. So we did make that decision and it was the right one, even though today it would sell for like more than 2x, you know, in the market from what we sold back then. But um, so anyway, to answer your question, Jason, I don't know. It's so subjective. I think it's wise for early stage funds, maybe after five, six, seven, you know, eight

• 34:59Speaker 02

  years in their positions to start thinking about liquidity and 20, 30% off the table, even if they have high confidence that, you know, it's going to go up from there. My best advice.

• 35:09Speaker 03

  How are you about recycling? Recycling? Teach me about recycling.

• 35:13Jason Calacanis?

  Well, anyway, I actually have thoughts on that, too. My best advice is if you have an opportunity, since they're so rare, take it, sell 10 to 20% twice, maybe three times. And then by the end of the story, you have 70% of what you could have had. No LP is going to be upset about that. And they're quite the opposite because if you gave them that money, you know, 18 months ago, and then they put it into Sophia's fund, they're looking at it as, you know, okay, there's a time value to money, too. And then what if that company implodes? And that specific company had like a lawsuit and a couple of challenges, if I remember correctly,

• 35:51Jason Calacanis?

  with their competitors. And so I had a company that got to a billion dollar valuation. We sold 18 million of our position. We kept 80%. That company's now worth 300 or 400 million. We look like, and that was two years, three years ago, we sold it. We look like geniuses, return the fund. Our syndicate got a bunch of money. And so, and we did it with Comm. I personally did it with Uber, right when Masayoshi Son was offering to buy shares in the 30s. Now, it seems crazy with Uber at 90 that I sold in the 30s. I feel great about that trade because I bought a house that doubled in value during that time. So then, the truth is, with the time value of money, maybe I left a third of 15% of my investment. It just doesn't matter.

• 36:34Jason Calacanis?

  What does matter is downside protection. So that's my sort of take on it. And man, I have

• 36:41Jason Calacanis?

  two, only like really two regrets. I was offered to sell some Robinhood at $30 a share, and we wound up distributing at, I think, $14 a share. When we distributed, I told everybody, "Hold your shares," because it went public and we were pre-seed investors. You know, some people sold it, some people held it. That $14, now it's at $100. So that fund, the difference would have been like a, I don't know, 10x fund versus a 3x fund, if you held your shares or whatever, 4x fund versus 10x. I don't have the math in front of me, but it's significant. So I was like, "Oh, maybe I should have held my shares in Robinhood," and held on to the public shares and distributed them two years later, which is what Sequoia has been doing quite effectively.

• 37:24Speaker 01

  Yeah, it's at 107 right now, Jason.

• 37:26Jason Calacanis?

  Oh, what am I doing on this podcast? I'm rich. I buy. I'm gonna go mountain biking. What am I doing here? No, it's like I woke up one day and like, you know, hundreds of thousands of dollars in Robinhood shares that I got as my carry turned into millions of dollars in Robinhood shares. It's a great thing about being a VC. If you love the company when it was private and it makes it to public, why would you sell it when it's public? Like unless the founders aren't there or something dramatic happened. I mean, obviously, you have to re-underwrite it every year or every six months. But man, let your winners ride.

• 37:58Speaker 01

  And Jason, answering your question about Q2 Series B valuations, I have that for you right here, which is, you can see, they are going up, much like every other round. But the biggest gains that we're seeing are in the super late stage, the D-plus era of venture. Does that match, Jason, what you expected to see?

• 38:18Jason Calacanis?

  Yes. There's so much late-stage money available because companies aren't going public. Until, until LPs and GPs see companies going public earlier, they're going to keep making these late-stage investments out of their, what would have been their public allocation. They'll just be like, okay, I'll buy Stripe, SpaceX, Andro here before they go public, because, you know, those companies probably should have gone public already.

• 38:49Speaker 01

  So on the point you made about profitability earlier, Jason, is that, is that what happens when we have smaller team sizes and just faster revenue growth? Because to me, it sounds like startups are just getting more efficient overall. I'm curious if it's more of a mindset shift, or if it's more just this is what happens when you spend less money by hiring fewer people.

• 39:08Jason Calacanis?

  I mean, we've seen this step function happen, I think, three times in my career, like client server, cloud computing, slash mobile, that time period, and then now with AI. So if you keep lowering the time it takes to get a product to market and the amount of money, it used to be a year or two to get a product to market and $5 to $10 million. Then it became like $1 million in six months. And now it's six weeks in an accelerator and $50,000 to get a product to market. I mean, it's not even comparable. So many more startup bets to make. That's why I'm trying to increase the surface area. That's my big, if I have any realization this year compared to last year, is that surface area really matters? Because there's just so many more companies.

• 39:53Jason Calacanis?

  So you have to take many more meetings, many, place many more bets. To your point, Ryan, like, how did I not know about that company? That was Sequoia's experience when Techstars, Y Combinator, and Angelus came out. They're like, how do I not know about these companies? And they're like, I guess we can't know about them. There's just too many companies. Now, it's, I think we're going to see, I don't know what Cambrian explosion means other than a big one. So somebody educate me, what is Cambrian? But whatever Cambrian, it sounds good, sounds intelligent, but I think it's like a 10x. I think we'll be sitting here in two years and have 10 times as many startups. Hitting, you know, product market fit than we did five years ago.

• 40:30Speaker 01

  The Cambrian explosion, Jason, was about 500 million years ago and it was a rapid diversification of types of life and the main hypothesis is that there's more oxygen, so more life got started.

• 40:39Jason Calacanis?

  Yeah, so that I knew that. I was testing you, Alex. I knew the Cambrian explosion.

• 40:44Speaker 01

  Well, now I only knew half of that, so.

• 40:46Speaker 02

  Now, now, anyone, and it's gonna get better and better, can build, use software to build their solutions. And so historically, you'd have some accountant in the Midwest, maybe, who really understands their space, understands their customers, understands their own problem, they can at least build like an MVP. And yeah, maybe the vibe-coded tools are not production-ready. You know, call back to T, perhaps. I don't know if it was vibe-coded or not, but, you know, it's a security issues. But it's gonna get better and better. And so I think the number, not think, it's pretty clear to me that the number of builders are going to increase. Now, whether those are all startups and like venture-backed companies is another question. But we're gonna see a lot more building and creating and shipping.

• 41:22Speaker 03

  So, speaking of this, I just invested, this is the first angel check I've written since I started the fund, because I just have been really focused on the fund. But the founder of Lovable DM'd me like a week ago and was like, hey, we should do stuff together. And we got on a call and they were like, we want you to angel invest. And it's like, I think, you know, it's not gonna be like a huge check, but, you know, they're the fastest, fastest-growing startup ever. They just reached 100 million in ARR eight months after launching the product. They're at like a 1.8 billion dollar valuation.

• 41:56Jason Calacanis?

  Anton from Lovable, yeah, I had him on the pod. It's very impressive piece of software for this vibe coding.

• 42:02Speaker 03

  It really is. And this is kind of exactly what we're talking about. People are creating software in 48 hours and generating like tens of thousands of dollars worth of revenue on it. And these are just, you know, these aren't even necessarily startup founders. So I'm curious, I mean, I don't know, how much time have you spent thinking about something like Lovable? And like, as an angel, that's like, I think that's probably, I don't know if it's the highest, you know, the, it's not a late, it's not late, but it's probably maybe the most expensive, you know, check I've ever written. Do you think I'm making a good decision?

• 42:32Jason Calacanis?

  I mean, you're basically looking, what's the... Price to sales ratio, price being the valuation of the company, sales being the revenue of the company. Price to sales should really just be valuation to revenue? Would be a cleaner way to say it so people would understand it. So is it a billion dollar company now or 10 billion?

• 42:53Speaker 03

  It's 1.8 billion, but in eight months, they've reached 100 million in ARR.

• 42:58Jason Calacanis?

  So it's 18 times sales.

• 42:59Speaker 03

  The velocity is like.

• 43:01Jason Calacanis?

  So the question is, will that sales continue? And the thing I'm hearing against this, Sophia, is people are sampling these products at an extraordinary rate. I would say similar to when apps came out, remember you buy a flashlight app for a dollar? You buy a game for $2.99 and like play it for five minutes and then never do it? Because you're like, well, it's only three bucks. Paying 20 bucks for a lovable or any AI product, you use it for a couple of hours and then you cancel it? Or you use it for three months, you cancel it? That's going to be the question is, is that quality revenue? Or is it brittle revenue? What's the revenue? Is it durable revenue? I think is the way I would say it versus brittle.

• 43:42Speaker 03

  Yeah, what's their churn like?

• 43:43Jason Calacanis?

  And the way you can determine that is when you talk to the customers, is this an essential part of their workflow? Is anybody here ripping out Slack or Notion or Coda? If you use those things like, I can't imagine ripping that out of my company or Google Docs ever.

• 44:02Speaker 03

  Have you seen Craft?

• 44:02Jason Calacanis?

  Oh, use the glue? Is that glue or?

• 44:04Speaker 03

  No, no, it's like Notion, but easier to look at.

• 44:08Jason Calacanis?

  Oh, really? I don't know that one. Craft it's called? I use Notion Coda, but once you get deep.

• 44:14Speaker 03

  I used it for the last LP update.

• 44:15Jason Calacanis?

  Oh, fantastic.

• 44:16Speaker 02

  I read that. It looks great. It was very well designed.

• 44:19Jason Calacanis?

  So I guess, Ryan, what are your thoughts on brittle versus resilient revenue?

• 44:25Speaker 02

  I mean, there, well, obviously churn matters and retention matters and everything. But also there's this interesting time where, so Evada, my partner on the fund, and I have chatted a bit about this more recently and she wrote a blog post about this. Maybe I'll share the show notes or something later, but. We're in an interesting time where the foundational layer, the foundational models that everyone is building upon are just getting better and better. And so without you as a builder, founder, doing anything, theoretically, your product is just getting better. And there are certain use cases where it hasn't reached that tipping point where the utility has met consumers' needs, but it will over time. And you building on top of these foundational layers, you don't need to do the heavy work. Not that it's difficult

• 45:06Speaker 02

  to build everything around it, but you know, there's so much opportunity coming and it's almost more about being in position and capturing users so that when the foundational models and AI is good enough to solve the problem that you're promising, then you're there. And so that's actually a shift. It's very different than like cloud infrastructure. When cloud infrastructure came around, that like shifted, you know, cloud computing, SaaS, all of that shifted dramatically, but that was more binary. It was like you put in the cloud or you didn't. Like maybe got a little faster, maybe got a little bit cheaper, but didn't foundationally change your underlying product and offering. And so there's something that we're looking at.

• 45:39Jason Calacanis?

  This is a profound insight, Ryan. So good to talk to you. I haven't talked to you in a year, but you always have these like really good insights. So what you're saying is imagine if your AWS account, your S3 storage made your product better while you didn't ship any new product. That's like a really interesting thing because there's you improving your product and then there's your underlying technology improving your product. So you could argue like AWS got cheaper, where the storage got cheaper, or maybe it got marginally faster, but that's not the same as what LLM's advancing is doing. Sophia, are you going to make that outside of your fund or inside of your fund?

• 46:19Speaker 03

  Outside of the fund. I mean, it's not, it's not, you know, I'm investing at like sub 20 million.

• 46:26Jason Calacanis?

  You've got to talk to your LP. Make sure, as one of your LPs, I'm saying put it in the fund and make an exception and it's a learning experience.

• 46:33Speaker 03

  I haven't done it yet, but I think it's like, I don't think it's, I don't think it would be a challenging 10x. And I think if I was, you know, I-

• 46:40Jason Calacanis?

  Do it. Do it in the fund. You don't want to get-

• 46:42Speaker 03

  Because I have relationships with founders, even though I'm not like a lean check, I've found it pretty easy to contact a founder when they like, you know-

• 46:48Jason Calacanis?

  Of course.

• 46:49Speaker 03

  ...raise subsequent fundraising and be like, hey, anybody want to buy, you know, can I sell some secondary shares? So, you know, you know, like-

• 46:55Jason Calacanis?

  As an LP, I would say do it in the fund and say, this is an experiment. We have 22 bets we're making. One of the bets, we thought we'd try a later stage one and see what we learn there. And, you know, obviously- We don't think this could be a 200x, but we think it'd be a 10x and that could be accretive to the fund and, you know, it would be a single or double and it would be lower risk. So we're going to maybe experiment in this fund and the next fund and having a couple of those, if it's a special circumstance where I have access. I did that with Cloud Kitchens. I have access to, and I'm friends with Travis. I had the opportunity to invest in his fund and my third fund for Cloud Kitchens. It was extraordinarily high out of, you know, our normal investment zone, but I put

• 47:38Jason Calacanis?

  10% of the fund in because I was like, I could bet on Travis to 10x 10% of the fund and return the fund. If he doubles it, great. If he triples it, great. It's all accretive and I have unique access. So that's like the unique access carve out that as an LP in your fund, I would be really upset if you didn't take it.

• 47:55Speaker 03

  I mean, it's a tiny check. It's just our ownership, like all of it.

• 47:59Jason Calacanis?

  Don't worry about ownership. Just worry about what you think the return is.

• 48:01Speaker 03

  Yeah.

• 48:02Jason Calacanis?

  If you think it's low chance of not returning and it's high chance of returning low single digits, it fills in the fund. It may not be a fund.

• 48:12Speaker 03

  I think it'll, I'm, I feel good about it. I wouldn't be considering it as an angel check if I didn't, so.

• 48:16Jason Calacanis?

  In order to return the fund, if you have 22 bets in the fund, it has to be 20x. So that's going to be hard to do, but 5x would be possible.

• 48:25Speaker 03

  Wix is worth like 20 or 30 million or something like that.

• 48:28Jason Calacanis?

  Billion, yeah.

• 48:29Speaker 03

  Billion, yeah. It's like.

• 48:31Jason Calacanis?

  It feels like, it's so funny you bring up that company because I was in a meeting with Kelly, who's running our syndicate and I was asking for an update and she said, yeah, I'm building a new portal. And I'm like, oh, okay, that's interesting. We hired a company to do that or we got a freelance developer. She's like, no, no, I'm building it. I've been vibe coding in lovable. Wanted to show it to you. It's a little early, but here's what it is. And I was like, oh, you could build a portal like Angel List, you know, for our private syndicate without being a coder. Okay, interesting. It feels like there's something bigger. Sophia, we had a hanging, a hanging question about recycling. Do you recycle 10% of your fund, Ryan? What's in your docs? What do you do?

• 49:17Speaker 02

  So both recycling and follow on is flexible. So we don't have anything that's strict in our LPA or anything like that. My position with follow on and that kind of flows into recycling a bit is, or it's related, I should say, is on the follow on side, it's like if we believe in this company, all things being equal, even if we're not an investor, would we invest in this company at its valuation today, knowing what we know now? With regards to recycling, we recycle within a certain time period generally. So if we get returns, sometimes companies shut down, they return the capital. We recycle that capital. But if it's year six of a fund, year five of funds, we tend to distribute from there. I mean, by then we're also on another fund entirely. So that's how we've approached it.

• 49:58Jason Calacanis?

  Yeah, I've recycled, I think, 10% and I think in a couple of the funds that we've done. You know, it's, you have to play the game on the field, I think, Sophia, since you were asking for advice. And for me, the game on the field is if there's no DPI and that provides DPI to your LPs, that's the more important thing than recycling. If you're already returned the fund, you're in the black and it's just a matter of how much you're going to return. Yeah, then it feels like maybe recycle it if you have the opportunity. Like if lovable is available and you had a million dollar return, putting a million into lovable in a $10 million fund. And now it returns 5X and now it's, you know, you're at 15 million returns of funding.

• 50:41Jason Calacanis?

  It could be whatever, really accretive, you know?

• 50:44Speaker 01

  Jason, for founders out there who are listening and may not be familiar with capital recycling, can you just break that down for the folks out there?

• 50:50Jason Calacanis?

  Super simple. In fund documents, when you get the first returns back, if you had a $10 million fund, you might say, we're going to recycle the first 10% of funds that come back. So if you have any early wins, instead of distributing the million dollars, which LPs probably don't want a quick win of 10% of what they put in. If somebody put in 100K, getting a 10K check is nice, but not life changing. Hey, maybe we take that million. We know there's a winner in this portfolio. It's, you know, that Nectar company. And hey, let's put the million into Nectar and we'll be alongside True Ventures and we'll have even more ownership in what we believe is a really high conviction bet. So it's just a way to goose the eventual returns of the fund, you know?

• 51:34Jason Calacanis?

  Now, if you didn't have any winners in the fund or breakouts yet and you couldn't identify them, then you probably would want to just distribute those returns to your LPs.

• 51:44Speaker 01

  Just because they probably don't want to take on extra risk at that point in time?

• 51:47Jason Calacanis?

  Yeah, they would probably want you to work towards doubling or tripling the money. As an LP in 21 funds right now, I, yeah, it's too many. I've been saying no to a lot of people.

• 52:01Jason Calacanis?

  I said to everybody, like, if you double my, if you double the money I gave you, you know, and it's just basically like stock market returns, I'm happy because I don't need access to this capital anyway. It doesn't need to be liquid. It's like a wealth bomb for my daughters down the road. But if you quadruple it or five X it, then it's meaningful for me and I'm stoked. And if I can get bill relationships or get intelligence from Sophia, you know, she's got this great company, Nectar and what was it? Nectar Social?

• 52:32Speaker 03

  Yeah, Nectar Social.

• 52:33Jason Calacanis?

  Okay, like if I ask Sophia, can I get an intro? She'd be like, sure. You're an LP. Of course I'll give you an intro. Like, and Mark Andreessen specifically does this. He was an LP on my first fund, but we had a mini micro falling out because he wouldn't come on the pod. Then why, why are you an LP? And he's like, well, do I have to come on the pod to be an LP? And I said, you know, now that I think of it, yes. And he's like, okay. And I was like, okay. We haven't really spoken since. I mean, we had a couple of little back and forths, but.

• 53:01Speaker 01

  That's a little petty then why he blocked me. Okay. Well, on that note, Sophia, I think it's very interesting that you brought up Lovable because they are such an amazing breakout company from Sweden, if memory serves, and you're based over in the UK. So I'm curious. Are AI startups in the European area performing as poorly as some American VCs think? Because there's been quite a mean lately of, you know, America builds, Europe regulates, Europe's dead, et cetera. But Lovable seems to break that mold. So I'm curious.

• 53:27Jason Calacanis?

  I'm right here, Alex. You could just say Jason.

• 53:30Speaker 01

  So Jason hates Europe, especially France.

• 53:32Jason Calacanis?

  No, I just don't think I'm going to find the next unicorn there in all likelihood. That's all. Certainly not in France.

• 53:40Speaker 01

  Is that correct, Sophia? Or are we being a bit too freedom fries over here?

• 53:44Speaker 03

  I've been here four months, right? So, I mean, my-

• 53:47Jason Calacanis?

  If you're an expert, go.

• 53:48Speaker 03

  You should speak with us. Definitely not an expert. You know, I think, you know, I've spent a bunch of time with like Brent Holberman and Founders Forum and went to the Founders Forum event a couple of months ago and spoke at London Tech Week and whatever. So I'm like just immersing myself in the ecosystem. But, you know, I think, you know, Founders Forum was really exciting. There were some exciting companies. The founder of Lovable spoke, founder of Propo-City spoke. But in terms of Europe, I feel like Estonia and is, is, there's like a, the concentration of startups in Estonia and the, you know, how it lends itself to being founder friendly or whatever. I'm not, I don't, I read about it and I forgot the details, but it seems like Estonia is kind of having a moment.

• 54:34Speaker 01

  Isn't that where Skype was from originally? Am I crazy? Jason, back me up here, Skype?

• 54:38Jason Calacanis?

  No, I think they were Swedes, but they might have been from an Eastern Bloc country. You might be right. There were three founders, so-

• 54:48Speaker 01

  We're both right. It was founded by Sweden, people from Sweden and Denmark, but was primarily developed in Estonia.

• 54:52Jason Calacanis?

  Got it, yeah. So, you know, the Nordics are special because those people have a design aesthetic that is really high. And it's really cold and there's nothing to do for six months of the year, so they just work. Whereas in France, Italy, Spain, it's lovely. Why would you spend 12 hours working on your startup, 14 hours? Why would you give up a weekend? If I lived in Italy, I would not be working on my podcast and I would be out and about. I would be getting pasta, branzino, whatever. And the lifestyle does drive. I've seen this in every single local market.

• 55:32Jason Calacanis?

  If the lifestyle is amazing, you got rich parents, cost of living is low, people are going to go out and just have fun and live their life. If the nightlife sucks- And there's nothing to do like San Francisco, like literally, if you're in Palo Alto, your last meal is 9:00 PM, unless you're going to like the 24 hour Denny's like there's like two choices, Denny's and like an Arby's by the airport. Like that's it. You know, even In-N-Out Burger closes like at midnight in the Bay area. So.

• 55:58Speaker 01

  This is why I never actually believed the VCs who said that Miami was the next big startup town. I'm like, it's way too much fun.

• 56:04Speaker 02

  It's been boring. I think San Francisco, I'm way more social. I have way more fun in San Francisco than Miami.

• 56:10Jason Calacanis?

  That's because you like to go to hackathons. That's about you, Ryan.

• 56:13Speaker 01

  Yeah.

• 56:13Jason Calacanis?

  Ryan's not going to the club or surfing. Are you surfing in LA? What are you doing?

• 56:17Speaker 02

  I went surfing the first time this year in Costa Rica.

• 56:19Jason Calacanis?

  So you didn't get the bug. If you got the bug, you'd be out there surfing four days a week. That's when you know you're fucked with your investment is when the founder is surfing four or five days a week. LA is amazing for lifestyle. Sophia knows that.

• 56:34Speaker 03

  It is. I have zero company in LA.

• 56:38Jason Calacanis?

  I mean, I mean, getting people to work hard is my like, I've developed strategies around it, but I have now realized like working hard and putting in 10, 12 hour days and effort is for 10% of the population. Like having a career, I think is for 20% of the population. I think just everybody else's live to work to live now. The number of people and it's a generational thing and it's no judgment. It's just the observation.

• 57:11Speaker 03

  So I just tried to.

• 57:13Jason Calacanis?

  Big time.

• 57:14Speaker 03

  I just hosted trust funds, first founder residency in Mallorca for a week. And so invited all my portfolio companies out. I was like, I rented this, I mean, a very, the management fees on a $5 million fund aren't very high, but I dropped like, it was probably a $20,000 expense. And I got this like seven room villa and was like, if you want to come out here, I've got this. I'll feed you. I ordered a chef one night. We went out to different restaurants. We went to the beach once. We went on a boat, which was like amazing.

• 57:44Jason Calacanis?

  Do people co-work?

• 57:45Speaker 03

  They co-worked. Yeah, and I sat with them. I'm like, oh, cool. I get to be in Spain, be near the ocean. These guys get to sit in our pool. We get to talk about like, you know, whatever latest thing they're paying attention to or reading and all educate each other. I get to sit there and mentor them like on my time zone and everybody kind of like gets what they want and like get to build relationships. So I'm really excited to institutionalize that into the fund because it's like a selfish.

• 58:12Jason Calacanis?

  Genius.

• 58:12Speaker 03

  You know, it's I feel like.

• 58:14Jason Calacanis?

  No, no, it's genius.

• 58:15Speaker 03

  It's just like no comp, no talks, no, totally unstructured.

• 58:20Jason Calacanis?

  What I love about your idea is that's going to inform your follow-on investment. It's also, they're going to help each other. So we call them jam sessions. We do something similar, but it's just a jam session or a pod. So we have our companies get together and do a pod where they meet every month and we have 11 investment team members. So they have about 30 potential founders in their pod. They get five to 10 to show up every month. They share what they're working on, what their challenge is on. You go around the circle and they help each other and we're just facilitators and founders love meeting with other founders because I, my thesis, Ryan, is founders are mutants. And like, I get

• 58:58Jason Calacanis?

  to be Professor X, you know, like we're the school for mutants and they feel uncomfortable around humans, but they feel very comfortable when they're with other mutants. When you see those great scenes from the X-Men movies when they're in the school together, they're like joyful and fun and nobody's being judged because like I can make an ice cube, you can light something on fire, I can walk the walls. Yeah, we all have something we can do that's an incredible skill. But then you put them with humans and it's like they're misunderstood, you know, and they're just, it's not fun.

• 59:29Speaker 02

  They don't trust. I mean, there's a lot of empathy and like trust that that's, we used to actually do this at weekend fun. We just opened it up the portfolio saying, hey, we're gonna do a Zoom hang. There's gonna be max five, seven of us and we're just gonna chat about like what we're working on, what challenges you have. And yeah, there's more trust. And of course, you put that same person in front of like a VC especially or their team, like they're gonna act different. They gotta, they have to look confident. They can't be honest. It's a totally different, it's an environmental thing.

• 59:54Speaker 03

  Is there a way that ongoing you guys, do you have like a Slack channel for your founders? Is there?

• 59:59Jason Calacanis?

  We have a Slack instance, yeah.

• 1:00:01Speaker 03

  You do? Do they use it?

• 1:00:02Jason Calacanis?

  It's unbelievably popular. We have 400 portfolio companies in the 12 years I've been doing this from a Sequoia Scout, Angel List syndicate to now. And we even have the failed companies in there that are shut down and we let them stay there. And we have an accounting, tax channel, growth channel, and we have their channels and we have our entire investment team in each of the private channels for their companies and we'll talk to them there. And they help each other. It's not us leading it. They lead it. And it's, and then this book phase, it's, I think it's a great thing to do. Persistent, great place to do it. You have to also staff all these things. So as a fund, especially a small one, you gotta pick, like,

• 1:00:45Jason Calacanis?

  you can't start 20 programs. You gotta pick the three most effective that you enjoy. So what's great about the one you chose, Sophia, is you like to be in a great Airbnb in a city and try new food. You're like me, you're a foodie, you like to travel. Ryan likes to be on his computer. He wants Product Hunt. He's obsessed with being on his computer and products.

• 1:01:06Speaker 03

  No, Ryan's a surfer.

• 1:01:07Jason Calacanis?

  No, he's surfing. Ryan has surfed.

• 1:01:11Speaker 02

  I have, I have once.

• 1:01:12Jason Calacanis?

  But Ryan really likes to be online. He's addicted to being online in online communities. He created one of the great online communities of all time, Product Hunt. That's, you can always tell it's a great community if it still exists. Product Hunt still exists. So that means it's a great community. They got Product Hunt. So that works for you, Ryan. You like to co-work. Sophia or I, co-working for five hours on a Zoom might be death. Like, we might be like, ugh, it's draining to be on a Zoom.

• 1:01:36Speaker 03

  It's so draining, you guys. I have to go. Sorry.

• 1:01:39Jason Calacanis?

  No, that's, that's why we taped an hour. All right. What are the news stories? Let's do a lightning round news stories. This has been great, guys. It's just great to catch up with you two and share notes.

• 1:01:48Speaker 03

  I was so intimidated. I still get so intimidated about joining podcasts for whatever reason. Unless, you know, most people just want me to babble about my life. And it's like really easy to talk about yourself, but talking about smart people things, I'm like, am I smart? I'm just always asking myself if I'm smart.

• 1:02:04Jason Calacanis?

  So full of it. I know your shtick. You're like, I've only built a $350 million company.

• 1:02:12Speaker 03

  It was overvalued.

• 1:02:15Jason Calacanis?

  Not your fault.

• 1:02:17Jason Calacanis?

  You've nailed it, like self-deprecating.

• 1:02:21Speaker 03

  I don't imagine being inside my head. It's fucked.

• 1:02:24Jason Calacanis?

  You're just saying the same things that I say. I always send Sophia a thumbs up or a heart on her social just to let her know, like, you're doing good, girl. Keep going. You can do it. All right. You know, I always like to give everybody the ability to plug a startup or two or an investment or two that they're super excited about. What do you got, Sophia? And maybe Alex, we could show what ever she pulls up.

• 1:02:47Speaker 03

  You know, when you were talking about portfolio companies working together, one thing that's really cool is one of my portfolios, Nectar Social, is a customer of Agree.com. And Agree are another one of the breakout companies I invested in pre-seed. They're basically going to replace DocuSign. And what they're creating is a signature to payment flow where when somebody signs an agreement and there's an invoice associated with it, they pay before the flow is over. So you don't necessarily have to send an invoice. And so they have a lot of SaaS companies. They work with Beehive. I made a TikTok about them and I guess like they got like a four million, a customer with like $4 million a year in revenue, like who like found them on my TikTok,

• 1:03:27Speaker 03

  which is like really cool. But yeah, they've got like 40,000 customers. And they, they came to me through, I literally like look through the, you know, the pitches that come through the website and most of them are like consumer, just like off thesis. And I like, I looked at this and it was like Agree.com. I was like, what's this? So they just literally like cold pitched me. They could have gotten to me, like we know mutual people, but they cold pitched me and I was like, this. And they just raised like a $10.2 million seed round, like a year after their pre-seed, so.

• 1:04:03Speaker 01

  And Sophia, you also mentioned Baton.

• 1:04:06Speaker 03

  Yeah, so Baton Market, I invested at seed. They just raised their Series A from Obvious Ventures. And so they are building a marketplace for SMBs to find qualified buyers and for people who want to buy mostly like local, kind of ugly businesses, I guess, is the trend. You know, profitable businesses, someone who might be doing like a roll up of like dry cleaners or, you know, yoga studios or coffee shops. And so Baton Market makes it really easy for people to acquire companies. They're doing amazing jobs.

• 1:04:41Speaker 01

  Awesome. Now, Ryan, you sent in three companies of yourself. I believe one of them was Deal, which we've already talked about, but you also mentioned Atlas, which is a very interesting company that I did not see coming.

• 1:04:52Speaker 02

  Yeah, Atlas is a, so Met and Mohawk, we invested in the C round, has gone on to raise a Series A and B. And what they're building is a sort of a layer to apply for visas, particularly starting with Indian travelers. Us in the US, we sort of have an advantage, like we don't need to apply for visas, you know, for a lot of different places to travel, but for Indian, you know, consumers, they need to apply for visas. They have to go to these like janky government websites and wait a long time. And they basically created this really clever wrapper, not in the negative sense, but a wrapper around this entire experience where you can actually apply and do everything within the mobile app. And it also shows like you're tracking and everything. And it's just a really interesting space. It's a massive market that I think a lot of people are overlooking.

• 1:05:33Speaker 02

  And my favorite part about Atlas is Mohawk, in the very beginning, he was just like effectively building APIs on top of government websites through web scraping was how they started. So it's like, all right, these government websites don't have APIs. They're not like modern. Let me just like effectively build our own API and build on top of that. And, you know, this is also a time like right before COVID hit, which is also an interesting time to be building a business like this. So anyway, I love the CEO Mohawk and what he's building there and just creating like more flexibility and convenience with traveling is just, I think, a net positive for the world too.

• 1:06:05Speaker 01

  Okay, Jason, what do you got?

• 1:06:07Jason Calacanis?

  So we just wrapped up Launch Accelerator 34.

• 1:06:12Jason Calacanis?

  And two companies that really got a lot of attention. One was Auto Lane, which is by a serial founder. He previously had a company called Neighborly, which rented storefronts. And Neighborly was this great idea that died during COVID, victim of the COVID wars. But you would take a storefront and people could go there and rent it by the hour for a book club, for a rehearsal dinner, for an offsite. And people loved it. And there was all this extra, you know, if you live in LA and you've been to like, I don't know, West Hollywood, there's all these storefronts, or Montana, or, you know, there's all these storefronts everywhere.

• 1:06:54Jason Calacanis?

  And so imagine taking one of them and making it an Airbnb, essentially. Anyway, that failed. He came to me with this new idea, Auto Lane. He said, you know, self-driving is here. And I said, yeah, I'm aware. I've got a couple of investments in that space. And he said, people are going to be doing self-driving deliveries and pickups. I said, say more. He said, imagine your Walmart, HEB is the big chain of like grocery stores in Texas where I live, and you have a Tesla coming to pick stuff up, a DoorDash car, an Uber. I'm like, well, they have all those coming. He's like, yeah, it's chaos already. Now imagine you add 10 different fleets of automated cars. So they're building the operating system to manage that.

• 1:07:38Jason Calacanis?

  So they sell into a Walmart or to these other places, you can pull up the website. And that gives them software to know, hey, these are the parking spots for the automated vehicles, and Ryan owns a Tesla Model Y. Ryan, you might send your car to the central market and/or this Whole Foods. That's a distinct possibility. So instead of ordering from Instacart, imagine, Ryan, you ordered from...

• 1:08:09Jason Calacanis?

  Whole Foods and then Whole Foods brought it out to the curb and put it in the back of your car.

• 1:08:16Speaker 02

  Autonomically, without me doing it, being there.

• 1:08:18Jason Calacanis?

  Without you doing it, but it's your car.

• 1:08:19Speaker 02

  Yeah, right.

• 1:08:20Jason Calacanis?

  Or so now, Sophia, imagine like, oh, you get dropped off at work and then it goes and picks up your Air One lunch and your team lunch and then brings it back to your office and parks in your parking spot. How does that whole handoff at Air One work? Then imagine a man, Air One, or I don't know, um, pick a company, Domino's Pizza decides they want to own the fleet. So Domino's Pizza says, okay, we're going to have five Model Y's or Waymo is selling their technology to Toyota now and Volkswagen has their own thing. So they buy five Volkswagens and they decide they're going to send these Volkswagen IDs out to deliver pizza. Well, they still need an operating system to manage all that. So anyway, he's building that operating system and all the handoff and he's super early.

• 1:09:05Jason Calacanis?

  But what was amazing is this founder is a fundraising machine and that's a new criteria for me. We have 13 criterias for investing, product velocity is one of them, world-class design, serial founder and alumni of our programs. This person has all of those, but he's also a fundraising machine. So I added that as one of our 14 fundraising machine as a tag for like a founder we love. Cause some, we have some founders who are great at product velocity and great ideas and great at recruiting, but for some reason they can't raise money. Infuriating and frustrating because it's like they have all the other qualities. So anyway, I love that one. And then another one that's really interesting, this team think came out of Google or Uber, I can't remember.

• 1:09:48Jason Calacanis?

  And it's called Doctors and you may have heard people are doing self-directed healthcare. And where you're seeing self-directed healthcare most of all is in travel, elective surgeries.

• 1:10:04Jason Calacanis?

  I don't know what they call those, but elective surgeries and traveling to places where you have the highest rated providers and the lowest price. Medical tourism? Medical tourism, thank you. So, medical tourism is part of a subset of a bigger theme of self-directed healthcare, which I think like superpower, whoop, aura, eat sleep, that's all like self-directed healthcare. This is different. This is like elective. So, people are going for dentistry to Mexico, stem cells to, you know, Panama, all types of augmentations and facelifts in South Korea.

• 1:10:45Jason Calacanis?

  So, they started with hair transplants in Turkey and then their, their secret that they figured out that nobody else did is this is all happening on TikTok. And there was this like fear that people had, is this safe? Should I do this? And then there's the people who are, you know, have these centers in Turkey and they're trying to convince people it's safe. And it turns out TikToks help people bridge that gap. And so, that's their first one. And then the next one I didn't know was in Spain, Portugal, France, freezing your eggs and doing IVF is like $5,000. In the United States, it's $30,000.

• 1:11:24Jason Calacanis?

  So, now people are going to two harvest cycles for 60 days. And it's like, so I asked them, like, when people do that, are they doing it because it's that much cheaper? Or are they doing it because they want to have a two-month vacation in Spain or Portugal or France? And you know what they said to me? Yes, it's both. You can spend $5,000, get an Airbnb for $5,000, have an incredible relaxing 60 days in France, harvest your stuff, and but you need to have some marketplace between them. And so, they're the marketplace between them. So, there's two. That just graduated last week, or this week, actually, from the Launch Accelerator. If you want to come to the Launch Accelerator, launch.co/apply. We've done 34 cohorts.

• 1:12:09Jason Calacanis?

  It's been really fun.

• 1:12:11Speaker 01

  All right, well, friends, that brings us to a wrap for today. And Sophia, thank you so much for coming on. Where can people find TrustFund? And where can people find you on the great wide internet?

• 1:12:19Speaker 03

  Trustfund.vc, and then I'm Sophia Amberusso, pretty much everywhere.

• 1:12:25Speaker 01

  Pretty much everywhere.

• 1:12:26Jason Calacanis?

  Instagram is, you're big on Instagram.

• 1:12:28Speaker 03

  TikTok? I don't spend as much time. I don't always cross-post. But yeah, I'm just focused on Instagram. I'm an elder millennial.

• 1:12:36Jason Calacanis?

  Yeah, elder millennial Instagram, right, yeah. I'm a Gen X, so I'm on X.com/Twitter. Where are you, millennial Ryan?

• 1:12:45Speaker 02

  Millennial Ryan, I'm on Twitter. That's where I spend most of my time. R Hoover. Yeah, I'm not on Tik. I mean, there is a TikTok. You'll find it if you search, but I'm not gonna, not gonna say it's good content.

• 1:12:57Speaker 01

  And the website is weekend.fund, I believe.

• 1:13:00Speaker 02

  That's right.

• 1:13:00Jason Calacanis?

  Yep. We're at launch.co.

• 1:13:02Speaker 01

  There you go.

• 1:13:03Jason Calacanis?

  With no M. I'm still trying to get the launch.com, but I'm fine with the launch.co. Founder'university, which is our pre-accelerator, where we teach people how to start companies, which will be coming to Saudi. We, press release went out. I haven't really talked about it too much, probably. But Founder University, the second city in the world will be, after the United States, is going to be in Saudi. And then I'll probably bring it to two other countries in 2026. We're announced two countries in 2026. And I'm at Jason on Instagram and at Jason on the Twitter X.

• 1:13:35Speaker 01

  All right, well, we're back on Friday. Thank you all very much. We'll see you then. This has been Twist.