Naval’s $500 VC fund, the Maduro Polymarket scandal, and NYT defends theft and murder | E2280

0:00This is disgraceful. You have an obligation to think through what you say. Crazy and deranged behavior that's all being bundled together and violence towards individuals you disagree with. We live in a democracy. All violence is immoral, as Martin Luther King said. As Jesus said, this is an incredible fail by the New York Times. So are we going off duty or do you have a news story or two you want me to comment on? I got one news story. I feel like people are going to want to hear your thoughts about this. Angel is - Is this Hassan on New York Times? Are we doing that on off duty? We can talk about that again.

0:27We can talk about that some more if you want to, sure. Yeah. Lute Maxing. I know you're a big fan of Lute Maxing. AngelList has a new product out called USVC. They're offering exposure to venture investments with a$500 minimum. No accreditation required. The goal is long term capital appreciation, not traditional liquidity. It's a little bit like venture for normies, venture for kiddos. That's sort of how people are describing it. There's been a lot, Jason, a lot of discussion over the last 24-48 on X about this. Criticism has been really sharp. There's a viral thread from a guy named Mario at covered underscore call.

1:07He's calling this yet another grift in the world of retail accessible VC. And he says retail doesn't need access to private markets this badly. A whole laundry list. Here, I'll pull up the tweet so you can see. So this is AngelList's new US VC, US Venture Capital. This is an SEC registered fund that allows non-accredited retail investors to invest in private pre-IPO companies. Correct. And my friend Naval is doing it, Ravikant, who's been on the program. And so they've got a bunch of portfolio companies in there that people want. The way this works is these are, I believe they're called closed-end funds.

1:48what they allow you to do is you, instead of paying carry, the 2 and 20 you hear about venture capital, 20 % carry, 2 % fees a year. So if you had a$100 million fund and you turn it into a $300 million fund in returns, that means you had 200 in profits. The VC would get 20 % of the 200, not the 300, but of the gain. 20 % of the 200 is$40 million. So that's what VCs are hoping for. They're hoping to triple your money. You're hoping they triple your money because you would double your money in the stock market is the theoretical concept here. Once in a while, you get an outlier that pays 5x. Once in a while, you get a dud that pays 0.5x.

2:32You lose half your money sometimes, you go 10x sometimes, but you're hoping for 2.5, 3x. In this one, you just pay a fee, 2.5 % annually. So if this became, if it was the same analogy, you had a$100 million fund, you would be, as the fund manager, you would get$2.5 million a year. So in 10 years, instead of getting the$40 million in carry, you would get$2.5 million a year guaranteed over 10 years. So you get$25 million. So it's kind of a wash for either party in terms of the fees. the issue becomes, in one case, the VC is really incented to swing for the fences because the carry is not guaranteed.

3:17In this case, the 2.5 % fee is guaranteed. So all you're trying to do is increase the assets under management. If you get it to a billion dollars in holdings, you're making $25 million a year, which means you make$250 million over 10 years. You got a pretty great lifestyle, you know, and okay, there you are. It's a nice balance between the two. What's brilliant about what Naval did is this is taking the SPVs, the special purpose vehicles that I participated in and that I moved my business to the syndicate. Naval and I had like a mini falling out. You know, I was a little bit too big for the platform.

3:54I was a little too annoying to him, I think, because I wanted to get treated differently. So when you run a platform, you're a socialist. You're just like, I don't want to negotiate one deal with J. Cal and another deal with these other angel investors. I was like, well, I'm Michael Jordan. I've got a book. I'm hot stuff. So I want a different deal. And we couldn't come to terms, whatever. So I did the syndicate. All good. We're still friends. But the brilliance of what Naval did here is the people who have the SPVs on AngelList are, from my understanding, being invited to put their shares into this.

4:25Correct. So he doesn't have to hunt for shares or go on a crazy hunt to buy secondary for people. He can just move what's on Angelus there. So I have a position in Calm.com. I think we own about 5 % of Calm.com. If the company was worth a billion, I could move that$50 million into this fund. I think we would get liquidity. The fund would buy it. And so that would move all of these SaaS companies or over 10-year-old companies. And you could get liquidity. And the public could own them. and the public wants to own them before they go public. Right. So it could be really nice. The other limitation is you can only take 5 % out in terms of redemption.

5:02Yes. So each quarter, they're going to target, I think, 5%. But if they can't let you redeem, then you're stuck in it. It's not like having public equities where you can just leave an ETF. Yes. I mean, I think that's what a lot of the complaints are. And there was another great sort of blog post. Hari Raghavan addressed a lot of the complaints. It was saying this is basically retail investors who are used to public markets who don't understand how private markets work and are objecting to things that are just part of the nature of how venture capital works. So, yeah, this was his post. Don't listen to the peanut gallery.

5:36USBC is a watershed moment. I mean, you picked up on a lot of what the complaints are. They're arguing that because the portfolio manager is incentivized based on assets under management rather than performance, he's going to focus on finding new investors rather than taking care of the current shareholders, making him more like a salesman than a fund manager. That's what the original complaint was saying. Who is this saying this? Don't listen to. I know it's important for us to just, you know, in terms of us calling balls and trikes to know who is doing this and what their motivation might be.

6:08Yeah, the criticisms are coming from this guy, Marco S. Just in terms of like always good to know the source. Yeah. He's in a similar business. I think I wouldn't. Oh, the other guy, Marco, who's making the complaint. He is a research lead for Artemis, which is an investment research platform. So he's a public investor, researcher, advisor, expert, whatever, what have you. Yeah. OK, with 2000 followers. So always go into the peanut gallery. Look at how old their account is. When did they make their account? He's been on Twitter for six years. Okay, he's only got 2 ,000 followers. It was really this thread that he wrote or this big tweet that he wrote.

6:48It got over 620 ,000 views and it became kind of the center place. Ankur Nagpal, the portfolio manager of USBC, is in the comments discussing it with him. It became kind of the hub for this whole conversation. So this is a very important thing. when you're building a business and people come and criticize it, you have to make a decision. Do you want to engage or not? And should you engage? As a person with 2 ,000 followers, they've been on the internet for six years or whatever, they may have a very neophyte view, and just trying to educate them just might not be worth, the juice may not be worth the squeeze.

7:24is here's the great thing about markets. If people look at this and want the opportunity, and they're not accredited, so they're theoretically not sophisticated, if they put their money in this and they lose, the way I look at it as an American who participates in the markets in a very vibrant way, public, privates, and everything in between, and once in a while I'll do a wager, play poker a heck of a lot, People need to be able to place bets. They need to be able to try these devices. If you were Lon and Lon's got a decent nest egg, it's not retiring yet. It's got another 10 years of work in him, maybe 15.

8:06Yeah, 15, 20, something like that. 15, 20. He could buy$500 of this. Learn by betting. Yes. That's what I do. I place bets to learn. Now, I don't place a giant bet to learn, but if I'm learning PLO, Pot Limit Omaha, you know the four card variant of texas hold them you get four cards not two so if i want to play plo if you think i go to the big table you think i put my entire no i i would literally jason calaganes played at the like one two dollar three five dollar plo table last time i was in vegas i'm not an expert plo player i have some expertise in nolan home having played for over 10 years so i'm like i don't care what table i said i just i just said sit me at whatever plo table is open And I don't care if it's, you know, 10, 20, 25, 50, whatever, one, two, I'm just there to have fun and learn.

8:56You could just place a$500 bet on this lawn if you wanted to and learn. I would encourage you to place$500 bets 10 times in the next month and then learn. I have started this with my daughters. I am now letting my girls, you know, basically invest in the public market. So with my 10-year-olds, I was literally talking to them about what stocks to buy. Congratulations to the team over there. If any of my startups, I did my first like 50 SPVs, my first 50 syndicates on Angelus. If they wanted shares of those in this, I would absolutely consider it. And so fantastic. Great. I'm happy for them. More liquidity for founders, for investors is a good thing.

9:42Monetary velocity is very important for an economy. So the fact that people have choices, angel investors, syndicates, incubators, pre-incubators, pre-accelerators, public markets, these closed-end funds or whatever they are, ETFs, fantastic. Let 1 ,000 flowers boom. Let the money move around. Anybody who's a participant in this understands. No crying in the casino. And it's your job to protect yourself at all times. Yeah. That's it. Okay, so you've identified a real problem and you put together a solid solution and a business model that you believe in. So you're all set to launch your new company, right?

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10:56So get all the advantages of a Delaware C-Corp independent, regardless of where in the U.S. you're operating from. Visit northwestregisteredagent.com slash twist for more details. And the links are in the show notes. I think that's pretty straightforward. work that don't don't invest in something unless you understand it and you're aware of the risk is a good rule i'm not buying mr uh micro strategies yeah you know why i because i i understand bitcoin pretty well i mean i read the paper you know i've been covering it for since 2010 on this very podcast one of the first podcasts to ever cover it yeah but when when michael saylor explains these like five different vehicles to get exposure to bitcoin i'm like Too confusing.

11:39Yeah. There's no way to talk about what he's doing and not make it sound like a scheme. Like every time somebody is like, I'll explain to you a microstrategy. Okay. First, here's what you got to say. It's like, you've already lost me. Once it's that complicated, I'm not interested. I'll go invest in something I can figure out. Yeah. Well, here's the idea. Just buy Bitcoin directly. Right. Or Solana or your coin. Or Solana or Tau. Yeah. I mean, you got choices of where to put your stuff. Okay. Let's get going. Okay. Well, there's OpenAI released GPT 5.5 slash pro setting apparently a new standard for frontier models.

12:10We can talk about that a little bit. Great. It's just yet another model. I don't think the jury is out yet. This week in AI, they will run it through its paces against the previous version and Claude. And you can look for that demo video next week. There we go. They haven't done it already. I think we're good with news. I think we're ready for off duty. There was a story here I did want to talk to you about, though. Did you hear about this special forces soldier who apparently bet on the Venezuela Maduro raid on Polymark? I did. Yeah. It's queued up for the audience here. All right. This is interesting.

12:42Yes. So federal authorities have charged Gannon Ken Van Dyke on making bets on the raid that removed Venezuela's Maduro from office. Van Dyke allegedly bet thirty three thousand dollars on Polymark, 13 bets starting in December and going through January. He won$409 ,000 on these bets because he was he was, in fact, betting that the U.S. would invade Venezuela and remove Maduro from office, which, of course, let's go eventually did. So here's the here's the actual Justice Department quote following his successful trading relating to Maduro and Venezuela related contracts. Van Dyke allegedly sent most of his proceeds to a foreign cryptocurrency vault before depositing them into a newly created brokerage account.

13:26So it kind of seems like he knew he was sort of getting away with something and trying to sort of avoid the authorities. The CFTC is about to hit him with civil charges. And Polymarket apparently are the ones who identified him and turned him over to the authorities. Their statement, insider trading has no place on Polymarket. Today's arrest is proof that the system works. OK, so. I'm going to say completely reasonable what's happened here in terms of the action that's taken.

13:58However, I love the idea of our military placing a bet on themselves. So. You do want them to feel confident. I am glad that those guys are going in, or ladies, I'm glad that they're going in feeling like we got this. That's how I want our military to feel. So I think from where I'm sitting, When I play blackjack or roulette or even poker sometimes, I will, if I'm in a funk or I'm feeling frisky, either way, either end of the bell curve, I will move into my patented splashy-cashy mode. Yes. And many people have seen me go splashy-cashy. So I will, if I'm betting, you know,$100 a hand, um, blackjack and I'm playing three hands, I got$300 going out there.

14:54I'm no bigwig here, but you know, my friends will put like$5 ,000 a hand, a thousand, but I'm playing three$100 hands. I will take a$25 chip or I'll ask for change. Give me some tens, fives, 25s, whatever. And I put the dealer in. Sure. You can put the dealer in and I splashy cashy in to change the mojo. Sure. Especially if I got a cooler dealer, you know. If they're chatty, if you're enjoying the back - No, no, when I say cooler, if they're, you know - Oh, you mean if they're - Giving me back cards, I'm suspicious, dad. But anyway, I go into splashy cashy mode. This is what I think we should do.

15:26I think we should take the special forces and we should allow us to place splashy cashy bets for them. Oh, I see what you mean. So if they're going in - Yeah. Like, let's say they were going in to get that pilot. Right. And let's say there's a hundred guys in the out. I want to be able to put 10K on them succeeding in the mission. You want to wager on a live combat situation. I want to be able to put 10K. This is incredibly deranged. It's a little, I feel like this is a dystopian sci-fi movie. It is like a dystopian sci-fi. Rich guys are betting on the war as it's happening. No, I don't want the proceeds from it.

16:06I want to put the 10K and let them get the return. Forward it to the SEALs or yeah, SEAL Team 6. Fuck yeah, let's go. Whoever's like a turn. It's fascinating that you would say that because you and President Trump, he was asked about this. And your perspectives are very aligned. I'm going to share. Yeah, I'm going to share. This is not good. When Karen Swisher calls me mini Trump, this is not good that we're so aligned. Oh, no. Here's what our president had to say. Can you guys hear that? I like it. He's got a little bit of confidence. I like the fact that he's confident. And I love the soldiers making a little bit of cheddar.

16:38Was he betting that they would get him or they wouldn't get him? It sounds like he was betting on his removal from office, that Maduro would be removed. It just sounds like she was involved in the operation. That's like Pedro's betting on his own Kings. It's up to the heat, because they kept him out of the Hall of Fame because he bet on his own team. Now, if he bet against his team, that would be no good. But he bet on his own team. I'll look into it, yeah. There you go. He's not upset about it because he's betting on his own team. One more. Here's one more little snippet of Trump's reaction, which I thought this really struck.

17:10There's a little bit of a melancholy tone that the president strikes in this second answer. So here he was asked, like, well, what do you think about, we hear a lot of these stories about federal employees getting caught insider trading with this information on prediction markets. And they asked him just like, what do you think about that more generally? And here was Trump's answer. The whole world, unfortunately, has become somewhat of a casino. And you look at what's going on all over the world in Europe and every place are doing these betting things. I was never much in favor of it. I don't like it conceptually, but it is what it is.

17:44No, I think that I'm not happy with any of that stuff, but they have all these different sites. They have predictive markets. It's a crazy world. It's a much different world than it was. All right, there you have it, folks. Ponderous answer from our president. It seems like he's really thinking about this in a way he doesn't always engage with questions from the public. Well, I mean, listen, he's not into alcohol. He's not into gambling. He is into golf. I don't know if he gambles on his golf or wagers. I heard sometimes he's a little loosey-goosey with his gimme's. Yes, that's what they say. I think it's the term for it.

18:16Yeah, that's what they say. Like, that's a gimme. Cheats at golf a little bit. They're like, sir, you're 30 yards from the pin. That is not a gimme. Three inches is a gimme. One yard is a gimme. When you own the club, you know, who's going to tell you? Okay, whatever. Anyway, listen, he is non-alcohol. He is non-gambling. Okay, fair enough. I think wagering is an important skill for people to learn. I like Annie Duke's framing of it, thinking in bets. Poker great Annie Duke. I like the great Annie Duke. We should have her back on the pod. We actually produced the Annie Duke show for a while, which you first got into podcasting at the original this weekend when we were doing it back in the day.

18:56We had the Charlie Rose set. It was all black behind us. Yeah, we were way too early on that one. But here we are rebooting, and we'll be starting this week in venture capital backup. So we'll have three this weekend shows sometime in May, June, in time frame. So just teasing that. But if thinking in bets, always good. If you're a startup founder, you're going to have to do this. And we're all doing it all day long. So we do it when we're like, okay, I'm going to go to the airport. How much time do I need? You're placing a bet, you know, in terms of how many minutes. There's the book, Thinking in Bets.

19:29It's a quick read. Get the audio book. I think she reads it. Just required reading. So I guess we'll start off duty here. Sure. And I'll give you Thinking in Bets as a great book from the great Annie Duke, who was a, you know, real pioneer in poker in terms of a female in poker who dominated the field. Yeah. In those early days of the poker boom. And now she is a consultant to, I think, venture firm. She might even be working in a venture firm now. When I first started watching poker on TV, she was like the one lady who was in the upper echelon, like the championship ring all the time as any dude.

20:06Hiring can be its own full-time job. And hey, guess what? I already have a full-time job. I make podcasts and I invest. But when you're running a small company, we both know every hire matters. You don't want to waste any of the seats you have at your company. And the best partner you can have is LinkedIn Hiring Pro. Why? There's a billion people using LinkedIn. All the great talent are there. If you're proud of your work, you build a LinkedIn page and you update it. LinkedIn Hiring Pro is going to streamline and simplify the entire process for you. Nearly 60 % of companies using LinkedIn Hiring Pro.

20:37You're going to get an incredible candidate to interview in the first week. And, you know, we're looking for a new producer for the pod. We did shout outs here on the show. We posted it on my social media. We asked friends. You know where we found our next great hire? LinkedIn. And it was competitive. We had like three or four really good choices. So hire right the first time. Post your first job and get$100 off towards your post at linkedin.com slash hiring pro offer. That's linkedin.com slash hiring pro offer. Terms and conditions apply. That was at a time when it was pretty misogynistic and like, oh, women don't have intimidation.

21:13They don't have bluffs in them. They're not aggro. They're not aggressive. They're not strategic. They're not mathematical. I mean, it was pretty, I remember when I started 25 years ago playing cards or, yeah, about that. You know, it was not friendly to women. And it was not a friendly environment. And people thought, well, you could just bully any woman at the table. And I watched it. People would, you know, you'd have nine guys and a female at a World Series of Poker Table or at Commerce Casino or Hollywood Park. You'd have eight guys and a woman. And I would watch. The guys would test the women much more.

21:49They would raise them, et cetera. Which, if that's happening to you and people perceive you as weak and they're betting into you, you can exploit that. because you can just tighten your range, play stronger hands or re-raise them. There's a lot of ways to effectively counter that, like going all in. Great Netflix documentary called Queen of Chess that's out there right now. And it's fascinating because it's exactly the same in the world of chess. When women first started playing in the 60s, 70s, even the 80s, all the male chess players were like, they don't have the right constitution. They're too emotional.

22:22They're not logical. They can't do the math, like whatever, whatever. And it's about, you know, there's this early female chess champion who was playing Garry Kasparov and the top players in the world and was really like pushing back against it. Is she the one who Queen's Gambit is based on? No, I mean, Queen's Gambit is a fictional story that was like a novel that was just, I guess, loosely inspired by some of these stories. But, um, okay. But this isn't like the direct one. No, no, this is, this is, uh, Judith Polgar. She's a Hungarian chess prodigy. and starting as a teenager she was playing against like the the top competitors in the world and she had this kind of rivalry with gary kasparov the sort of famous russian champion who he played deep blue famously the ibm ai computer in those early days anyway this is a great it's a great documentary that follows her whole she's obviously famous for yeah so kasparov now very famous for challenging sacks of support of putin and russia those two get into it all the time he's like I'm from Russia.

23:22I'm Russian. There's Garry Kasparov in the movie. He's in this film. He's like, you cannot trust. You're like the greatest chess player in the world telling Zags you can't trust Putin. Yeah. It's hilarious. Hassan Piker is a streamer who's very far left, socialist left, and has said a bunch of spicy things that people are concerned about, like killing landlords and letting their blood flow in the street, which I thought was a joke of a quote. But it turns out people very quickly showed me the quote and he's being bombastic, performative, I guess. But there's been a lot of hand-wringing on the left.

23:58This isn't a political show, but when we go off duty, we'll delve into things because this is an important one because it speaks to anti-corporate sentiment. So I think I'm well within the twist purview to talk a little bit about this. Now, and I'm also, I'm a media executive. The New York Times hosted this discussion on their opinions podcast and their culture editor hosts it. She is, yeah, here she is. Nadja Spiegelman, Nadja Spiegelman. Okay, so she is smiling here, and this is a very jovial podcast. Why is that important? Well, it's three millennials in their mid to late 30s, 36, 37-ish. These are adults who've been in the workforce for 15 years.

24:42They're very well-educated. One of them works for The New Yorker. One of them works for The New York Times. And one of them is one of the most followed streamers These are legitimate, you know, seemingly intelligent, well-spoken individuals in a discussion here. And the first thing I think as a quote we should probably start with is the concept of micro-looting and then maybe go to macro-looting. So, Jacob, this is the one that starts early on, like 18 seconds in is where she defines micro-looting. Okay. So here we go. Micro-looting. I started going into the grocery store. I would pick up the thing that I wanted and then I would go.