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Jason Calacanis
This 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 you have a news story or two?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
One news story. I feel like people are going to want to hear your thoughts about this. Angel.
Jason Calacanis
Is this Hassan on New York Times? Are we doing that in off duty?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
We could talk about that. We could talk about that some more if you want to share. Yeah. Loot maxing. I know you're a big fan of Angellist has a new product out called US VC. 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 coveredcall. He'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, a whole laundry list here. I'll pull up the tweet so you can see.
Jason Calacanis
So this is AngelList's new USVC US Venture Capital. This is an SEC registered fund that allows non accredited retail investors to invest in private pre IPO companies. Correct. OpenAI 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. What 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 $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. So you lose half your money. Sometimes you go 10x sometimes, but you're hoping for 2 and a half, 3x in this one you just pay a fee, 2.5% annually. So if this became, if it was the same analogy, had a hundred million dollar 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Right.
Jason Calacanis
In 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 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, we, I was a little bit too big for the platform. I was a little too annoying to him, I think because I wanted to get treated differently.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
So when you run a platform, you're a socialist. You're just like, I don't want to do negotiate one deal with JCAL and another deal with these other angel investors. I was like, well, I'm Michael Jordan, I've got a book, you know, I'm hot, 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. Correct. 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 Angelist there. So I have a position in com.com, i think we own about 5% of com.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. So it could be really nice. The other limitation is you can only take 5% out in terms of redemption. So each quarter they're going to target, I think 5%. But if they can't redeem, if they, 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yes. And I mean, I think that's 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. USVC 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.
Jason Calacanis
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 strikes to know who is doing this and what their motivation might be.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, the criticisms are coming from this guy Marco.
Jason Calacanis
S just in terms of like always good to know the source.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
He's in a similar business. I think I wouldn't.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
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.
Jason Calacanis
Yeah.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Okay.
Jason Calacanis
With 2000 followers. So always go into the peanut gallery, look at how old their account is. When did they make their account? Okay. He's been on Twitter for six years. Okay. He's only got 2,000 followers.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
It was really that this, this, this thread that he wrote or this big tweet that he wrote. It got over 620,000 views and it became kind of the center place. Ankur Nagpal, the portfolio manager of usvc is in the comments discussing it with him, it became kind of the hub for this whole conversation.
Jason Calacanis
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 Jews. May not be worth the squeeze. Here's the great thing about markets. If people look at this and
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
want
Jason Calacanis
the opportunity and they're non 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're an, you know, if you were Lon and you, Lon's got a decent nest egg. It's, you know, it's, it's not retiring yet. It's got another 10 years of work in him. Maybe 15.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, 15, 20, something like that.
Jason Calacanis
15, 20. You know, 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'. Em, you get four, not too. So if I want to play plo, you think I go to the big table? You think I put my entire. No, I, I would literally. Jason Caliganis played at the like 1, 2, $3 5 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. I don't care if it's, you know, 10, 20, 25, 50, whatever, 1, 2. I'm just there to have fun and learn. You 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. 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. Monetary 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, you know, ETFs, fantastic. Let a thousand flowers boom. Let the money move around. Anybody who's a participant in this understands no crying in the casino, you know, and it's your job to protect yourself at all times. Yeah, that's it. Okay, so you have 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? Not so fast. If you want investors and potential customers to take your new business seriously, you need to consider forming a Delaware C corp. And that's where Northwest Registered Agent comes in. They're going to give your new company a real identity. That means an address for your public filings, a domain, a custom website, a business email, and a, of course, a phone number. And that's going to take just 10 minutes and 10 clicks. They don't charge hidden fees. Customer service is available around the clock. They're not overwhelming your inbox with spam, and they make it easy to cancel at any time. So get all the advantages of a Delaware C corp. Independent, regardless of where in the US you're operating from. Visit northwestregisteredagent.com twist for more details. And the links are in the show notes.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I think that's pretty straightforward that don't invest in something unless you understand it and you're aware of the risks is a good rule.
Jason Calacanis
I'm not buying Mr. Microstrategies. You know why? Because I understand Bitcoin pretty well. I mean, I read the paper, you know, been covering it for since 2010 on this very podcast, one of the first podcasts to ever cover it. When Michael Saylor explains these, like five different vehicles to get exposure to Bitcoin, I'm like, too confusing.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, 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 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. Something I figure out.
Jason Calacanis
Yeah, well, here's the idea. Just buy Bitcoin directly, right?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Or Solana or your.
Jason Calacanis
Your coin or Solana or Tao. Yeah, I mean, you got choices of where to put your stuff. Okay, let's keep going.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Okay. Well, there's OpenAI released a GPT 5.5 slash Pro, setting apparently a new standard for frontier models. We could talk about that a little bit.
Jason Calacanis
Great. It's just yet another model. I don't think the jury's 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
There we go.
Jason Calacanis
They haven't done it already.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I think we're good with news. I think we're ready for off duty. There was. 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?
Jason Calacanis
I did, yeah. It's queued up for the audience here. This is interesting.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yes. 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 $33,000 on parley market 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 US would invade Venezuela and remove Maduro from office, which of course.
Jason Calacanis
Let's go.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
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. So 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 has vowed to hit him with stuff, 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.
Jason Calacanis
Okay, so I'm going to say completely reasonable what's happened here in terms of the action that's taken. However, I love the idea of our military placing a bet on themselves.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
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.
Jason Calacanis
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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yes.
Jason Calacanis
And many people have seen me go splashy cashy. So I will. If I'm betting, you know, $100 hand blackjack and I'm playing three hands, I got $300 going out there. I'm no bigwig here, but, you know, my friends will put like $5,000 a hand. But I'm playing 3, 100. I will take a $25 chip or I'll ask for change. Give me some tens, fives, 20 fives, whatever. And I put the dealer in. Sure, you can put the dealer in. And I splashy cashy in to change the mojo.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Sure.
Jason Calacanis
Especially if I got a cooler dealer,
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
you know, if you're enjoying the. The back.
Jason Calacanis
No, no. When I say cooler, if they're, you know.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Oh, you mean if they're giving me
Jason Calacanis
back cards, I'm suspicious. But anyway, I go into splashy cashy mode. This is what I think we should do. I think we should take the special forces and we should allow us to place splashy cashy bets for them. Oh, I see. So if they're going in.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
Like, let's say they were going in to get that pilot.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Right.
Jason Calacanis
And let's say there's 100 guys in the aisle. I want to be able to put 10k.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
On them succeeding in the mission.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
You want to wager on a live combat situation?
Jason Calacanis
I want to be able to put 10k. This is incredibly deranged.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I feel like this is a dystopian sci fi movie.
Jason Calacanis
It is like a dystopian sci fi.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Rich guys are betting on the war as it's.
Jason Calacanis
No, I don't want the proceeds from it. I want to put the 10k and
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
let them get forward to the als or. Yeah. SEAL Team Six.
Jason Calacanis
Yeah, let's go.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Whoever's. Like, it's. 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.
Jason Calacanis
Not good. When Kara Karen Swisher calls me Mini Trump. This is not good that we're so aligned. Oh, no.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Here's what our President had to say. Can you guys hear that?
Jason Calacanis
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. Was 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 sounds like she was involved in the operation. That's like Pedro's betting that his own kings, 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, there you go. He's. 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. This really struck. There's. There's a little bit of a melancholy tone that the president strikes in this, this second answer. So here he was asked, like, well, what do you think about. We. We hear a lot of these stories about federal employees getting caught, insider trading with this information, prediction markets. And they asked him just like, what do you think about that more generally? And here was Trump's answer.
Jason Calacanis
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 like it conceptually, but it is what it is. No, I think that it is happy with any of that stuff. But now 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, they have it, folks.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Ponderous answer from our. From our president. He's seems like he's really thinking about this in a way. He doesn't always engage with questions from the.
Jason Calacanis
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 gimmes.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yes, that's what they say, I think
Jason Calacanis
is the term for it.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, that's what they say. That's a gimme. Cheats it. Go like a little bit.
Jason Calacanis
They're like, sir, you're 30 yards from the pin. That is not a gimme. Three inches is a one yard is a gimmick.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
When you own the club, you know,
Jason Calacanis
who's gonna who's gonna tell you whatever. Anyway, listen, I. He is non alcohol. He is non gambling. Okay, fair enough. I think wagering is an important skill for people to learn. I like Eddie Duke's framing of it. Thinking in Bets.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Poker. Great.
Jason Calacanis
I like to the great Annie Duke. We should have her back on the pod. We actually produced the Annie Duke show for a while when she first got into podcasting at the original this weekend when we were doing it back in the day and we had the Charlie
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Rose set, it was all black behind us.
Jason Calacanis
Yeah, we were way too early on that one. But here we are rebooting and we'll be starting this week in venture capital back up. So we'll have three this weekend shows sometime in May, June in time frame. So just teasing that. But if. Thinking in bats, always good. If you're a startup founder, you're going to have to do this if. 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. It'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 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 at a venture firm now.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
When I first started watching poker on tv, she was like the one, the one lady who was in the upper echelon, like the championship ring all the time.
Jason Calacanis
As any hiring 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. You're going to get an incredible candidate to interview in the first week. And, you know, we were 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@LinkedIn.com hiringproffer. That's LinkedIn.com hiringproffer terms and conditions apply. That was at a time when it was pretty misogynistic and like, oh, women don't have intimidation. They 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. You'd have eight. 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. They 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Great Netflix documentary called Queen of Chess that's out there right now. That's about. 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. They'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 Gary Kasparov and the top players in the world and was really, like, pushing back against it.
Jason Calacanis
Is she the one who Queen's Gambit is based on?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
No. I mean, Queen's Gambit is a. Is a fictional story that was like a novel that was just, I guess, loosely inspired by some of these stories. But.
Jason Calacanis
Oh, okay, but this isn't like, the direct one.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
No, no, this is. This is Judit 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 guy 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.
Jason Calacanis
Obviously famous for. Yeah. So Kasparov, now very famous for challenging Sax's support of Putin and Russia. Those two get into it all the time. He's like, I'm from Russia.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I'm Russia. There's Gary Kasparov in the movie. He's in this.
Jason Calacanis
He's like, you cannot trust. You're like the greatest chess player in the world selling zacks. 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. This 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, Here she is not just Spiegelman, Nadja Spiegelman.
Jason Calacanis
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. They'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, 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.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
So, Jacob, this is the one that starts early on, like 18 seconds in is where she defines microluting.
Jason Calacanis
Okay, so we'll go here. Micro looting. I started going into the grocery store. I would pick up the thing that I wanted and then I would go. It's a survival technique. Gotta eat to live, Gotta steal to eat. You're paying for that, right? No, babe, food is a human right. People are taking small things from big corporations and they're feeling justified. Like, look, everyone's shoplifting themselves. Microluting one.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Okay?
Jason Calacanis
So this is microluting. And you can, like, they put that, you know, soundtrack behind it, and she's smiling and hamming it up about microluting. Microluding is stealing. It's petty crime. Putting a new name on it does not make it less abhorrent. You should not steal. But this discussion quickly escalated to loot maxing.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yes.
Jason Calacanis
So let's tee that up. If you would, would you steal from the Louvre?
Guest or third participant (possibly Nadja Spiegelman or another guest)
Yes.
Jason Calacanis
I would not be logistically capable of executing such a fact. But would I cheer on every news story of people that I see it? Absolutely. Yeah.
Guest or third participant (possibly Nadja Spiegelman or another guest)
I. I think it's cool.
Jason Calacanis
We gotta.
Guest or third participant (possibly Nadja Spiegelman or another guest)
We gotta get back to cool crimes like that. Like, you know, bank robberies, right? Stealing, stealing, priceless artifacts, things of that nature. I feel like that's way cooler than the 7000th new cryptocurrency scheme that people are engaging with.
Jason Calacanis
Okay, so let's stop there.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Feel like part. Part of it. I feel like what's going on is that they are talking. Like, you would talk on a podcast. Like, that is exactly the sort of thing I would say on, like, a movie podcast. Not being intended. Like, I don't really think you should steal anything. Certainly not from.
Jason Calacanis
Oh, you wouldn't say this. You wouldn't stay still from the loop. You might make a joke about a movie.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I might be like, you know what I miss when people were doing cool crimes? Like, I might say something like that, being ironically flip. But that doesn't mean I really want to go. I'm never going to do a bank robbery. I don't think it's actually.
Jason Calacanis
So let me this. You're giving them far too much cover. This is the. The New York Times, the paper of record. This is a serious publication. This is not just a random podcast. This is the editorial leader, I believe, of the opinion page. This or one of them.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
She's the opinion culture editor. So she's the culture editor of the op ed page.
Jason Calacanis
And listen, Hassan is just an individual voice, okay? More power to him. He's like Fuentes or, you know, Tucker or Alex Jones. Like, these are spicy people. I get it. They're performative. But the other two represent the New Yorker, the 150IQ, legendary. We only hire the best, most thoughtful people to express, you know, Important ideas and to drive the culture forward. These are two legendary publications I grew up with that I had in my home. From the moment I could read, I was reading these publications and read them for my entire Life. For 30, 40 years, I've read these publications. This is disgraceful to host a conversation like this where you're seemingly taking it serious. I think there's a large portion of the audience that is going to take this as serious and be inspired by it to go micro loot. Now, they might not loot Max, but if you're a disturbed person, if you're on the fringe, you, you might very well take this thinking and this ideology to other places. So when you are a media brand of note, it could be this week in startups, it could be all in. It could be New York Times or New Yorker. Legendary publications. You have an obligation to think through what you say. I have learned this many times when I get clipped and people say, oh my God, you said this, you said that, oh my God, you were wrong about this. It happens to us. So you have a responsibility. The entire tone here is so off that you're laughing and encouraging people to do it. You're not at a bar, you're not at a birthday party, you're not at a dinner party. You're representing the New Yorker, you're representing the New York Times, Hasan's representing himself. Be more thoughtful and understand. You're inspiring people. Because when you look at how people feel about corporations right now, the next bomb drops and this is where you have to be incredibly judicious about how you say things. This all ends with a discussion of social murder as a subset of murder and assassinations. Social murder, let's hear about it. People feel that murder is morally justified. And I'm curious how we thread that line. Yeah.
Guest or third participant (possibly Nadja Spiegelman or another guest)
Engels wrote about the concept of social murder and Brian Thompson, as the United Healthcare CEO was engaging in a tremendous amount of social murder. The systematized forms of violence, the, the structural violence of poverty, the. The for profit paywalled system of health care in this country. And the consequences of that are tremendous amounts of pain, tremendous amounts of violence, tremendous amounts of deaths. And that was a fascinating story from, for me, because Americans are very draconian about crime and punishment. They're very black and white on this issue. And yet, because of the pervasive pain that the private health care system had created for the average American, I saw so many people immediately understand why this death had taken place even before they knew who the shooter was or what the motive was we had universalized this pain. So much so that virtually every American has a similar experience, a shared experience, where they have a loved one that spent their last days, instead of spending them with their family, spending it on the phone talking to their healthcare provider to. To maybe get a little bit of economic respite so they don't carry on medical debt for their next generation, for their next of kin.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Okay, that sums it up. That's, that's, that's. That's pretty much the idea.
Jason Calacanis
All right, so listen, I didn't go to graduate school. You can use all the fancy terms you want. Social murder, structural violence. You can be as disappointed as you want. You can't encourage or not condemn assassinations and murders. There's no justification for killing the CEO of UnitedHealthcare. It doesn't matter how much you suffered. If UnitedHealthcare caused you suffering. That is not the proper vehicle, assassinating people. This is crazy and deranged behavior. That's all being bundled together. Stealing, grand stealing and violence towards individuals you disagree with. We live in a democracy. You can very easily, as we've seen, elect Mandami to pursue socialist versions of the healthcare system and deprecate, say, a capitalist version of it. They've got him in office right now. He's gonna make socialist grocery stores instead of capitalist grocery stores. You're gonna make buses free. That's the proper channel. You just under no circumstances can start to normalize the murder of anybody, whether it's, you know, cops murdering somebody, ice beating people up on that side, or killing of CEOs. There is no moral equivalence here. All violence is immoral. As Martin Luther King said, as Jesus said, as countless people have it out. If a person who is destitute steals a loaf of bread and writes an iou, okay, fine. They're kids starving. They take a loaf of bread, they write, I'll pay you back when I get the money. I understand that philosophical debate, but here, this is an incredible fail by the New York Times. Incredible. To not immediately say and disclaimer and discredit a person murdering a father, a CEO because they disagree with how they provide a product or service. I'll just leave it there.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I don't think. Yes, there's no justification for murder, for shooting a guy on the street in the back. I mean, to me, I always come back to the, you know, if you're embarking on a plan of revenge, dig two graves. Like violence is this endless cycle. It doesn't ever solve the problem. It just. Now people are killing Each other on top of this problem already exist. Existing. I believe that. I do think at the same time, I think that we're in this place because people do feel a little bit justifiably helpless. Like, you could say, sure, you could elect a guy like Mamdani, but we've been trying to elect people in this country to fix the health care system for most of my lifetime. I mean, remember Hillary? Care was the 90s when we were begging the Clintons like, please do something about this.
Jason Calacanis
It is a seemingly intractable problem in the United States where we pay twice as much per person for health care. People feel disappointed in it, but yet we have the best healthcare in the world. Right. We have the best in terms of people coming here.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
If you can afford it, we have the best technology. Agreed. And that's the frustration, I think, is people looking through the window, seeing this amazing healthcare system that we can't all get equal access to. So I think you do have to acknowledge the frustration. I think it's kind of the same thing with the data centers. Like, Americans hate AI. They see these endless AI deals happening, these 10 billion, $20 billion deals, every huge numbers in the newspaper, people getting fired, and they feel helpless. And the data centers are the one thing that's like, I could do something about this. I can, like, stop a data center in my town. It's my way of taking back a little power. So I think you have to acknowledge those feelings while at the same time pointing out murder is not the answer.
Jason Calacanis
There must, nor is stealing.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I don't think stealing from a. Stealing from a store, no matter what the store is, is not the answer. Stealing from Louvre clearly isn't the answer because that's the property of the French people.
Jason Calacanis
But I mean, if you were gonna make that analogy, oh, by the way, that woman from the New Yorker, it turns out her last name is Spiegelman. And I was like, okay, let me figure that out. Like, that doesn't seem like her ethnicity. It turns out her dad is the author of Mao's the Amazing Graphic Novel. Art Spiegelman is her dad. She's a massive Nepo baby. Her dad is probably. She's a Nepo baby.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Art Spiegelman's kid.
Jason Calacanis
I literally have had 20 people DM me. I went to Yale with her. This is like a massive person of privilege. And I'm like, oh, my God. So, great book. Let's unpack this a little bit.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Novel mouse, please. Like, that's an awful, Unbelievable, just incredible.
Jason Calacanis
Chef's kiss. Incredible. Buy it and yeah. Read it with your kids. Unbelievable piece of art.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
All right, so there, there's. Okay, so for off duty in our thing here, we've got go watch this opinions podcast and understand that go buy Mouse the graphic novel. You will just keep it forever.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Unbelievable.
Jason Calacanis
You got Annie Dukes thinking of bets. And you got this chess documentary called
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Queen of Chess on Netflix.
Jason Calacanis
Queen of Chess. So we're moving here through it. Let me address your helplessness.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Sure.
Jason Calacanis
Issue. If you feel helpless, you need to reassess some things. You live in one of the great economies in the world where you can move to different states or you can leave the country. People in China cannot leave the country. People in India, by and large, cannot leave the country and go somewhere else. You can go to Spain. I've had family members go to Spain, move to Canada, move to other places where they have universal healthcare and they get access to the universal health care very quickly. By the way, you can opt out of the system here without murdering a CEO. You can. And you know, listen, I don't want to give credit to Karen Swisher and Prof. G. Professor Cole takes Prof. G. Yeah. Which, by the way, I'm going to be on Prof. G. Markets. I'm doing a debate with Ro Khanna on the wealth tax. So the kid who runs it with him, his co host, asked me to be on. I was like, okay, yeah, that sounds like it would be entertaining.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Fantastic. Yeah, that'll be good.
Jason Calacanis
Yeah, that should be pretty funny. We'll have to you and I do some debate prep for Ro Khanna versus the asset seizure wealth tax. Anyway, he did a thing on his podcast where he said, resist and unsubscribe. He, like me, thought this ice violence was crazy. He said, here's a way to get Trump's attention. Tank the stock market. How do you tank the stock market? You unsubscribe and pull up resist and unsubscribe in the list of companies. He basically said, I'm going to ask my audience, which is large, to unsubscribe from these companies. And he was asking him, unsubscribe from Uber, unsubscribe from Amazon prime, unsubscribe from ChatGPT. There's a list here of all the different companies. Apple, Amazon, Google, Microsoft, Paramount, and Meta, Uber, OpenAI, Att. So he literally is taking, by the way, I think, this list. If you held it up and you held up the sponsors of The Prof. G. Pod, FedEx, Dell, I mean, I'll give Prof. G. Prof. G. Or as we call Him. Prof. Cold takes because he's made. He thought Tesla was going to zero and he thought Macy's was going to beat Amazon. He's got some pretty weird takes. Putting all that aside, putting aside that he trashes me and my friends incessantly, he's correct. If you want to, you have economic power in this country. You simply stop going to Whole Foods. You simply opt out of these subscriptions. There are ways to do this that are nonviolent and not stealing. You are under no obligation to have 20 services. You could share your Netflix password. You could go over your friend's house and watch Netflix. You can opt out of this. And that sends the best message. The problem is people who even have these feelings, they're consumers like everybody else. They love capitalism's output. They love the fact that you can go on Amazon and buy anything. They're all Amazon Prime. If you actually don't feel this way, take six months to stop buying things. It's easy to do. I've done it. I am a person of privilege. I have said to myself, I'm not buying anything on Amazon for a month. And I have kept myself to it. Like, you know, I have too many boxes around. I'm buying too much stuff. Let me absorb what I've already bought.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
And I go through an unsubscribe binge every year. He's right. There is a such a clean message you can give to people through protesting, through unsubscribing. Now, I don't understand why people are still buying ads on a podcast where they're telling you to unsubscribe from the brand. That, to me, is a little bizarre.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
You got to keep that funnel going. You know, you need new users.
Jason Calacanis
What's going on here? You're sending Prof. Giving, you know, $15 million in advertising. He said in order for him to tell people to unsubscribe from you that you guys have Stockholm syndrome.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
It's interesting that for him, unsubscribe does not mean stop accepting their advertising revenue. It just means stop buying their products. There's only one way.
Jason Calacanis
Oh, the other still.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Okay, yeah.
Jason Calacanis
But anyway, this is the simplest way to do it. It's the simplest way to do it. That's all. Well, I mean, just opt out.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
That's what I always come back to. It's like when, when I, when an influencer podcaster goes on the air and starts telling me, you know, quoting angles and quote the Communist Manifesto. And he's like, well, like, are you a communist or not? Like, A Bolshevik would be like, what are you doing sitting in that studio? Get out there and start lighting government buildings on fire. You know, like, have a dangerous.
Jason Calacanis
We are not advocating this.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I'm not. I'm not advocating. Of course, I don't. I'm not a competent. I don't want a communist revolution. But I'm saying if you did. If that was your perspective, that capitalism is corrupt, we have to tear down the entire system and make a new system. That's not what these people are doing. They're not invested in overthrowing them. And they're. They all seem very comfortable.
Jason Calacanis
So I think you got to walk the walk.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
You always have to take that with a grain of salt. If somebody is, like, firebrand, radical, we have to, like, upset the system. And, like, we have to have a revolution and get rid of capitalism in this country. Like, okay, but it's hard to take that seriously when you're in a New York Times studio shooting a podcast and you're usually, like, streaming live on the Internet for five hours a day in your nice house. And, like, I don't. I don't know.
Jason Calacanis
This is how I felt about environmental. The environmental movement. There was a guy, Ed Helms, I think was his name. The actor. Yeah. Who was on scene elsewhere.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
The.
Jason Calacanis
Ed Begley Jr. Sorry, I just. I was trying to.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
He, He. Yes, yes.
Jason Calacanis
He did not own a car. Right.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
The bus everywhere.
Jason Calacanis
And yes, bicycles everywhere. He has a gray water system at his house.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Correct.
Jason Calacanis
He uses solar. He will not buy packaged stuff. He buys unpackaged stuff. He lives the life.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, he's very.
Jason Calacanis
Then we had people coming to Ted crying on stage about the environment, and they flew there on a G650, and they own seven homes, and each of the homes is 20,000ft and it's air conditioned when they're not there. Like. Like, if you really actually feel this way and you're, let's say, Bernie Sanders, who owns, I think he owns four homes or something like that. Okay, that seems like. You're not walking the walk, bro. And if you're in first class, like, you're not a man of the people, and if you're spending money on all this crazy stuff for your campaign, you're not walking the walk. So if you're gonna be pious like this, if you're gonna be Hasan, if you're gonna be Spiegelman, whatever, like. And you believe in stealing stuff, well, maybe start at home. Like, what can you give up to the people who are poor and can't afford food? Like, I Would just like to see some, on balance, behavior that actually means you're walking the walk. And there are examples of this everywhere. You can opt out. I live in the great state of Texas. I don't know if you know the place. Lon, in this great state, there are people who homeschool. They're like, I don't believe in the education system. I don't like what they're teaching. I want to teach it at home. I'm religious. I have my own ideas. I think I can do a better job. They homeschool, they are like, you know what? I'm gonna hunt deer. I know this sounds crazy. And I'm gonna have a chicken coop and I'm gonna have a well, and I'm gonna put solar on my wrench. Like, I'm part of that community of be self sustaining, live off the land, have chickens. I have chickens. I have eggs. I haven't bought eggs for a couple years now. I don't hunt yet. But I'm going to. I'm going to learn how to hunt. I want to learn how to, you know, kill my own meat, whatever. I think at a certain point, walk the walk is what I would say to these folks.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah. In fairness to Bernie, not a communist, a social democratic socialist. So he's not saying we should go, you know, like, light all the buildings on fire and overthrow the government. He does own three homes, though.
Jason Calacanis
I mean, and his net worth is like 30 or 40 million, I think.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, surely. Yeah. He's got a home in Burlington, Vermont, in a middle class neighborhood. He's got a home in D.C. because he's a senator and he's got a summer camp on Lake Champlain in Vermont.
Jason Calacanis
Yeah, that's the one. That's the one I've seen pictures of. And you're like, come on, bro.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Purchased for about $575,000 in like 1972, I think, presumably.
Jason Calacanis
I think it's a $50 million house now. All right, listen, last thing here. Greenlight.com, again, not a sponsor, but I'm teaching my kids about money and I want to do this kids investment club dot com.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Sure.
Jason Calacanis
Where we teach kids about betting. And back to Annie Duke's book on betting and just the gambling culture in Generation Bet. Greenlight.com allows you to give a credit card to your kids, but you can also let them invest in companies as well. So we are, you know, doing the allowance thing and giving money for chores and you get like savings goals and you can use this credit card to go buy stuff and it just teaches you how to invest chores and allowance cash back savings. Yeah. And it's got a bunch of like family safety things. It's Robin Hood for kids. It's basically for financial literacy.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah, that's great. That's very clever. I wish something like I wish this existed when I was a kid. Nobody was like, you should teach your kids how to invest in anything or you should teach your kids about banking. Like I was learning three words in like, like 18 different languages when I was a kid. That was.
Jason Calacanis
This should be the first thing we teach kids. Kids need to understand about money. And like check out this. They have a game in this. There's a game level up where they like quiz you on stuff. And I am super interested in the space. In fact I started. So yeah, if you pull that up long. Kids Investment Club. So I'm sorry, this is the green light one. And listen, they're not sponsors or anything but I just think it's a cool product. And then there's Kids Investment Club. So I was looking for a CEO or a general manager for this. If anybody wants to be the CEO or General Manager of Kids Investment Club.com I have the domain name, I have teen investment club, etc. So and I've got probably 2,000 people who gave me their emails. So if you pull upkids investment club.com, you'll see it there right now.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
There we go.
Jason Calacanis
If somebody has wants a job, I would start this with you. My idea is to charge like $500 a year for parents and their kids to be part of this and then have 50 weeks of programming, two weeks off or maybe 52 weeks of programming and make it a live zoom. And then you know, 52 lessons in finance and then have different finance people come in and you can come to a live zoom. And I think we could have 10,000 people paying 25 bucks a month, 50 bucks a month for their kids and then all the archives. So to be part of the live thing and like, like maybe you do it like a course, I don't know. But there's some way to do this to make it sustainable and hire a team of five or 10 people to like actually do this at scale and make it a for profit business. And then all the videos eventually come out for free for everybody. Just you know, if you don't have money, but if you want to be part of it, you pay 500 bucks to be part of it. You take the course, you get a certificate. Now your kids graduating high school or elementary school with a certificate yeah. In personal finance, it's just so important to know.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
And no, there's no effort in public school ever. You, they just send you out into the world at 18 and it's like, there you go, figure out. I wonder why there's no effort to educate kids into how. How to be smart about credit cards, investing, how to even save. Just the basics of how to make a budget that you can follow.
Jason Calacanis
Gets taught this I realized and I learned in my life. You know who gets taught this?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
The children of wealthy people.
Jason Calacanis
Correct.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
You know who doesn't get taught this? Kids who go to public school.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Yeah.
Jason Calacanis
If you go to public school, this doesn't come up. If you come from a rich family, they're like, let me explain to you. Corporate debt. Let me explain to you. Margin loans. Let me explain to you. ETFs. You just sit there with your mom or dad and they explain all this stuff to you. And then you got some finance person in your family office, you got some rich uncle, and they sit you down and they teach you all this. They teach you all of it and they tell you what to do and what not to do. And the rich get richer and the poor stay poor. Listen, I'm going to start sounding like Hasan Piker and Ms. Spiegelman and G.S. spiegelman.
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
I think the answer is microluding, Jason.
Jason Calacanis
No, it's macro. Looting the lube and selling the Venus de Milo and then putting that into crypto. No, it's just like you can get educated and have Invest America. All right, listen, we did a lot of show today. I have an idea here. Did we do enough show to not have off duty part of the main show?
Host/Co-host (possibly a producer or co-host of Jason Calacanis's podcast)
Do you think we could save it for Monday or something? You want to say?
Jason Calacanis
Well, no, I have an idea. What if off duty we release as a separate episode, just take one of the sponsors and add them to it for the weekend or something. If we have like any sponsor that needs a little extra love, we'll see you all on Monday. On this Week in Startups. Bye bye. Do me a favor, check out this week in AI AI. Sign up for the email. Follow us. You know, we gotta wake up the YouTube channel. So any comments you put under there, you subscribe, you put on alerts. If you thumbs up a video, if you save a video to a playlist list to watch later, all of that gives a little signal that YouTube should pay attention to what we're doing. And we'll see you all on Monday. Bye bye.
Host: Jason Calacanis
Episode: Naval’s $500 VC fund, the Maduro Polymarket scandal, and NYT defends theft and murder | E2280
Date: April 25, 2026
This episode covers three major topics at the explosive intersection of tech, investing, and media controversy:
Jason and his co-host break down the public reactions, ethical dilemmas, and business models underlying each story, often framing issues through a personal, candid, and at times satirical lens.
What’s New:
AngelList has launched “USVC”—a closed-end, SEC-registered fund allowing retail (non-accredited) investors to invest in late-stage, pre-IPO startups for as little as $500, with no accreditation required—notably led by Naval Ravikant.
[00:19–01:19]
Business Model Details:
"It's a nice balance between the two. What's brilliant about what Naval did...He can just move what's on AngelList there." — Jason (03:17)
Criticism & Debate:
"Always go into the peanut gallery, look at how old their account is...maybe just trying to educate them just might not be worth the juice." — Jason (06:33, 07:02)
Learning by Betting:
Jason defends access to risk, arguing small stakes ($500) are a reasonable way to learn, paralleling investment to learning poker at low stakes.
Quote:
"Learn by betting. Yes, that's what I do. I place bets to learn." — Jason (08:08)
Meta-lesson:
Both hosts note: Don’t invest in things you don’t fully understand—no matter how accessible they become.
[11:09]
Story Summary:
A U.S. special forces soldier, Gannon Ken Van Dyke, placed $33,000 in bets on Polymarket about the imminent U.S. operation to oust Venezuela’s Maduro—winning $409,000. Polymarket ID’ed and turned him in; he now faces charges for insider trading.
[12:38–13:46]
Reactions & Ethics:
"I love the idea of our military placing a bet on themselves." — Jason (14:08)
Host: "You want to wager on a live combat situation?"
Jason: "This is incredibly deranged."
[15:50–15:53]
Presidential Response:
They play a clip of President Trump’s unusually serious take:
"The whole world, unfortunately, has become somewhat of a casino... It's a crazy world. It's a much different world than it was." (Trump, 17:28)
Meta-lesson:
Jason and co-host reflect on the pervasiveness of betting as a metaphor for modern life, with Jason rooting it in "Thinking in Bets" by Annie Duke.
The Media Debate:
Jason sharply critiques a New York Times’ podcast where the notion of shoplifting (“microlooting”), big-art heists (“loot-maxing”), and justifying the murder of corporate leaders due to “social murder” are discussed with a jovial, unserious tone.
[24:24–27:00, 30:02–31:49]
Key Podcast Quotes (NYT Segment):
"Food is a human right... people are taking small things from big corporations and they're feeling justified." — NYT podcast participant (25:12)
"We gotta get back to cool crimes... like bank robberies, stealing priceless artifacts." — NYT podcast participant (26:22)
"The systematized forms of violence, the structural violence of poverty... Americans understand why this [CEO’s] death had taken place…" — NYT guest (30:02)
Jason’s Response:
He condemns the normalization of violence or theft as left-wing performativity, especially when coming from serious media institutions:
"You have an obligation to think through what you say... This is disgraceful to host a conversation like this where you’re seemingly taking it serious... You have a responsibility." (27:11)
Co-host’s Reflection:
Acknowledges American frustration with health care and big tech, noting people’s helplessness sometimes breeds nihilistic or self-destructive discourse, but violence/stealing is not an answer.
Practicing What You Preach:
Jason and co-host discuss the hypocrisy of “radical” podcasters who comfortably live inside the systems they denounce, contrasting them with figures like Ed Begley Jr. (who walks his environmentalist talk) and real homeschooling off-the-gridders.
Economic Non-violence:
Financial Literacy for All:
On the motivation behind the AngelList fund:
"If you wanted shares of those in this, I would absolutely consider it. And so fantastic. Great. More liquidity for founders, for investors is a good thing. Monetary velocity is very important for an economy." — Jason (08:08)
On “splashy cashy mode” while betting:
"This is what I think we should do. I think we should take the special forces and we should allow us to place splashy cashy bets for them." — Jason (15:38)
On media responsibility:
"You are inspiring people. You have an obligation to think through what you say... This is disgraceful to host a conversation like this where you're seemingly taking it serious." — Jason (27:11, 33:54)
On non-violent protest:
"There is such a clean message you can give to people through protesting, through unsubscribing. Now, I don't understand why people are still buying ads on a podcast where they're telling you to unsubscribe from the brand." — Jason (40:26)
On real empowerment:
"Kids need to understand about money. This should be the first thing we teach kids... The rich get richer and the poor stay poor." — Jason (48:48–49:25)
This summary captures both the substance and flavor of the episode, highlighting how Jason Calacanis and his co-host thread technology, investing, and media culture through the urgencies and absurdities of today’s business world.