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This week on the podcast, strap yourself in for a banger.

I welcome back my old friend, degenerate gambler Howard Linsen. We talk about stock twits, about social leverage, about his early investment in Robinhood, about why he's concerned about the degeneracy economy between meme coins and end-of-day options and parlays. He's concerned about what the next generation is doing. I thought this conversation was hilarious, and I think you will also. With no further ado, my sit-down with the one and only Howard Lenzin.

Wow, if only my kids could hear that

I know, they think you're just an old man They wince Use the finger and ask for pity

Surgically reattached Surgically reattached Is a lesson of how lucky we are I've lived without acute pain First of all, when I cut it off It's amazing how many people do do that

Was it still dangling on or was it severed completely?

You pick it up, you call 9-1-1 and you go, as a Jew, I wasn't sure if I boil it or freeze it. So that was the question I asked 9-1-1 because it's never happened to me.

Well, as a Jew, you're only supposed to take the tip off. I don't know if you cook it.

I don't know if you freeze it. It's like lobster. So the woman on 9-1-1 said, please don't bleed out. I go, that is not helpful right now. As luck would have it, I live on Coronado. Good advice. Don't bleed out. Good advice. I'm like, the one time I got to call 911, I go, let's not talk. Get me a machine over to my house. Get me a robot. So living in Coronado is a magical place. You've been there. A couple of times. And the great news about Coronado is the Navy bays, Navy SEALs are there. It's the greatest place in the world. They have a hospital right there? They do. But I'm saying there's cops and firemen everywhere. Everywhere, right. So literally, as I'm dialing 911, it's like they knew I cut my finger off. So as a miracle would have it, the young – I've never really had to be in an ambulance. So again, I'm lucky. And they took me off island because they found a hand surgeon who turned out to be 30 years old, which freaked me out. Right. Because I thought he'd sew it on backwards or whatever. Anyways, long story short, I was at peace. Once you realize you're going to live, because I've never had that happen, like something like that happen. Were you gushing blood? Was it frightening? Yeah, yeah, yeah. Yeah, as a favorite of my wife, I went to the neighbors to bleed. So it was like the next day it was spotless in front of our house. But as luck would have, everybody did a great job. The amazing thing, we make fun of so many things in America these days, the emergency system. I needed it. I don't care what I pay in taxes. It was amazing.

And yet you still have 10 fingers.

Yeah, I have 10 fingers for now. the joke

the family is, I don't want it, because it's kind of like a dead finger at this point. Oh, really? Will it be functional? Will you regain function? It feels like, if I'm using it, it just feels like a wet skin. Right. And so I'm not happy. But the doctor was like, you can decide later. It was his call. If you want a prosthetic or? No, not a prosthetic. If you just want to work with a nub. It's only a third of the finger. Right. So anyways, it was traumatic, but here we are. All right. Wow. Yeah, and there's great stories. If you're a storyteller, cut a finger off. I mean, if you want traffic on Twitter, bleed out.

Yeah, you'll get traffic, but no engagement. That's the problem with Twitter.

I want to go viral. I got nine chances.

21, if you want to be accurate.

Toes are not good in the outfit. Oh, no?

Fingers are good. And 21, the 21st, no go? The 21st, you could be president. So let's roll back a little bit and start with your early education. Bachelor's from Commerce University – Bachelor's in Commerce from the University at Western Ontario. Yeah, it's a famous business school for Canada. MBA Arizona State.

Famous for bums. Arizona State Business School. What does that even mean?

And then master's at Thunderbird School of Global Management.

Which was a great school now owned by Arizona State.

And a great animated cartoon in the 60s and 70s. Correct, correct. So given all that, what was the original career plan? Comedy. Yeah, I grew up.

You and Martin Short right out of Canada, right? Not Martin. He was already older. But I grew up in Toronto. And that was when I was 75 watching Johnny Carson on my first TV. um you saw everybody and it was like your living room and so it's toronto had second city at john candy martin short eugene levy second city was before saturday night live and so i grew up to around the same time weren't they a little earlier yeah yeah so i'm like 12 years old giggling you know and there was no internet so you're like go to the comedy clubs with your friends toronto had this club called yuck yucks which was a famous chain like the improv but of canada And you had Mike Myers. Another Canadian. Yeah. Everybody exploding onto the scene at the same time. And so I was doing stand-up in high school. Get out. But not good, obviously. But Mike Myers would come up. Mike Myers would come up and kill. He was like 17 years old. Right. Jim Carrey, 14 years old. Right. And killing. Right. And so everybody wanted to be a comic. No different than like the Web 2.0. Everybody went to Stanford to be an engineer. Right. In the 90s, it was investment. banking right now it'll be robots and ai it's just what's in the water and i grew up with comedy in the water and so that was the goal and obviously you know with jewish parents at the time that ain't flying especially i wasn't good right and so i went to school you you dropped that you

weren't good as like an afterthought i think if you're successful and earning a living well i even a jewish parent will put up with you now we'd be nuts like jerry seinfeld's mom is fine

with yes but i'm saying now if my son came to me and said i'm gonna go hit the comedy tour i'd warn him how dark it is but i'd say go make it go on youtube like right you don't have 10 000 hours you don't have to live in motels 10 000 hours yeah the faster you get those 10 000 hours and

the better that's right so you grow up in canada you start your career in phoenix and san diego and new york city i'm curious that's an interesting you know uh toronto phoenix san diego new york how did that geographical um upbringing affect your perspective as an investor

who was an investor i don't know because as a kid i was lucky yeah because if you're jewish in toronto or new york at that area you go to florida you know the original del boca vista and um but my dad was different and he discovered phoenix uh-huh and so in the 80s like phoenix was like swamp coolers and he just liked the weather and i don't know i'll let you know a

little secret the weather in florida ain't great it's humid it to my dad obviously that's what he

thought yeah so that's what he discovered phoenix and bought a home and i liked golf and biking and so lucky for me we had a i went instead of going to florida we were going to arizona and so i would go to the football games as a kid and i was like asu that was my dream just just just go to arizona state university which i ended up you know doing for grad school which isn't a great grad school but it was party school but that was my dream get out of canada right so i got lucky i you know my parents exposed me to you know arizona and i went to asu at the time It was amazing. And then if you're Jewish in Phoenix, because of the summers, it's like New York goes to Florida in the winter. Jewish people in Phoenix go to San Diego in the summer to get out of the heat. Right.

They want to be closer to the ocean. It's a nice weather. It's a six-hour drive, and it's 70 degrees. And I love La Jolla, and that whole area is just spectacular. It's called zonies.

So, Arizonans flood San Diego to Del Mar. I wish. And so, we grew up Coronado. I grew up, sorry. My in-laws had a place in Coronado. And so when we had kids, I'm like, get out of the heat if you're not rich. You summered in Coronado.

Yeah, not summer, but a week here, a week there. I wish California wasn't six hours away. If it was two hours away, 100%. We were just in San Francisco. It's fun again. It's a boom town. Tales of an apocalyptic hellscape have been wildly exaggerated.

It's still not my favorite, but it's cool. It's less homeless than New York. You know, I'm not just talking about homeless. The people are still.

They're educated. They're intelligent. I mean, if you're if you lose if you're not New York City, it's not New York. You know, when you leave New York, I don't know about you. I make a conscious effort to not be that New York abroad, even out of time, out of town.

Yeah.

California, especially San Francisco, it doesn't feel like you've left town. I love it.

Yeah. I mean, I just have the California bug. Yes. But coast to coast is a dream, and I get to live it. It's just a lot of travel. The thing about it, and I do like Florida a lot, but same as you, six hours, like Phoenix or San Diego, Florida is like not on the map. No brain, all right. No, no one does it. Like, it's not a thing.

Right. No, Phoenix to San Diego makes sense. Yeah. Next to Florida, just like New York to Florida makes sense. Correct. New York to.

So you asked how that happened. That's the rite of passage. Instead of Toronto, Florida, my whole life, I jumped to the West Coast. And then I discovered San Diego through my in-laws and my wife. And man. Yeah. Well, you've been to Coronado. Oh, yeah. It's lovely.

Yeah. So let me wrestle this back into submission. So you've worn a lot of hats. You're a hedge fund manager, a founder, a CEO, a seed investor. a media personality how do you describe to people who don't know you what you do it's a great

question my in-laws are in their 80s and they they still ask me what do we tell people you do and i'm like who the hell cares well and the world's now decided that for you no one cares right so what do you do right like i think we're getting back into like where it's you should be proud to have like a um what you call profession i don't have a profession so you asked how i got started as an investing i got started investing because i failed at everything else and which is kind of the larry david part of it is like i stumbled into it because the internet is like water it'd be like discovering california like internet was like tech so the 90s were like i didn't understand semiconductors right we're full circle right coder i'm not a coder i don't even know how things work I never did Radio Shack. Right. Right? Like walkie-talkies were freaking me out. So the odds of me being in tech are part of the comedy. Full circle, we are now back in a tech world. Robots, chips, like real stuff.

A little secret, we never left. It just kind of fell out of favor.

No, but I found the goofball era. Web 2 was the goofball era. Such as? Where you and I were at social media. You could be the class clown and have scale.

Okay.

Now that's gone again, and class clown, Now you need to be a bully again. You need to already have distribution.

Right. It's hard to build distribution today. So I'm saying- Being an early adopter is certainly an advantage.

But now it doesn't matter. You have to have real tech chops again. You can't pose like I am. Like I have imposter syndrome for the right reasons. Right. Because I'm an imposter. Meaning the internet left a little opening in 2006 for goofballs. And we got to participate in an era of free growth when Facebook didn't charge you or have an AI algorithm that blocked you. You could say whatever you want. People go, he's funny. And you could scale for free, which is why we had an internet boom, Web 2.0 internet boom right after the internet crisis. Now, we live in an era where those people are confusing their genius for a bull market. Right. And we're all sick of those people.

Can I push back on you a tiny little bit? Because I know you for so so well for so long. Hold the imposter syndrome aside. The early Internet rewarded people who could communicate effectively, be it work your way through the media via blogs.

Or short-form blogs like Twitter or other social media or podcasts or video and YouTube. There's a whole run of different ways to use the internet to scale. So it's not an imposter. You basically just kept tacking into what was working. Oh, this works. Let's do more of it.

Of course, but the era was free. So you had a great financial crisis. No one thought the internet was going to happen. So meaning Uber couldn't be possible without Google Maps. Like people say Uber is great. It wasn't possible unless there was an iPhone, the cloud, Google Maps. Metromedia Fiber, Global Crossing. Otherwise people would just be typing, I want a taxi without Google Maps. No one would know where to go.

That's right. And all of that only worked because of the bubble and the build out of Global Crossing and Metromedia Fiber. So I'm saying. $1,000 a mile bought for pennies.

No, but my imposter syndrome is born of, of course, I have an ego, but my imposter syndrome is surrounded by crazy people who are mistaking, as I was talking to Tim O'Brien, if this was, we went from a world where strength mattered, not that long ago, to a world where this matters. right no and i'm like people just the humility is gone and i feel it's with my kids and everything it's with the injury and everything you have to have some humility we need to get back to having some humility and laughing at our success and going wait a minute it was a bull market zero interest the reserve there was the free internet aws right you had youtube you had if you here's my question if you aren't successful that'd be more interesting i want to talk to the guy Like the Larry David commercial with FTX when he was like, oh, the circle, fire. Who needs a wheel? Who needs fire? That was such a great commercial because only Larry David or FTX, I know the guys who wrote the commercial. What made that commercial great is Larry David gets the joke. You idiots. He's in on it. You're in on the fact that, of course, you made money. You worked at Facebook. It grew because the product was genius and tricked people into signing up. You did nothing except ride the train. Now, I'm not saying smart people didn't work there, but let's remember, Game of Thrones, we're all dead. The people that are successful today are Marc Andreessen, Chamon, the people that I can't, like, are hilarious to me. They have no humility is that Game of Thrones era, we're all dead first, second, first scene. Right. There's a hammer in our heads. And you and I might have a chance because we're the court jesters. Right, that's right. And if we dance well enough. Dance for me, monkey boy. Andresen, dead. Chamath, dead. There's just a pitchfork in their foreheads on the first scene of Gladiator.

Well, if you, you know. So that's the imposter syndrome. You have people like Da Vinci that were consultants to the king to help build weapons and things. So unless you can, you know, early days of Palantir, unless you can say, hey, here's how to make a better catapult. Sure. You know, those guys survive.

So I'm saying I come along with like tweeting, stock tweets. It's like it was just enabling communication. Listen, I'm very proud of this stuff. And I also can laugh about how stupid it is. Like, I don't have another trick. Like, the Internet left this opening, kind of like discovering California. If you're early to discover California, it made it past the Indians and the mountains. Right. Didn't get robbed by, like, f***ing airs. Murdered, stampeded. Cash. Like, let's carry all our money in a stagecoast pulled by horses at three miles an hour. What are the odds we get killed? Right. It's impossible. So the internet left this opening, and I snuck through it. And it's fun to look back with some humor at the whole thing. You're going to laugh. I think the hole's closed up. Elon owns the pipes. Zuckerberg owns the pipes. True Social owns their version of a pipe. TikTok has an algorithm. How do you break through?

Because those things get tired, and the next gen says, just the way Facebook became, oh, my parents are on Facebook. I'm out. I'm going to go to Insta, and then I'm going to go to TikTok. And so there'll be something new.

I'm not questioning that. I'm just questioning it'll never be easier than when I made money. And I'm cool with that. Like, that's the imposter syndrome.

I don't completely disagree with you, and you're touching on a pet thesis I love to ask. What would have happened to you had you been born 100 years earlier? Yeah, first seen. Or even 25 years earlier, right? If you're born in 1940, what happens?

I'm a furrier. Look at my ox. Mo, take a look at my furrier. Beaver pelts. I have all these beaver pelts. I have a cafe that has so many dishes on it that make no sense. And I'm selling fur or something. I mean, I had no shot. I have no strength.

Right. Just think about how fortunate you were.

I cut my own finger off. Right.

So if you didn't bleed out, you're nine-fingered Howie forever. No, you should have turned that off. You stick your finger into the fire and you cauterize it. That's what the old-timers would tell you. Get a piece of steel in the fire. They'll heat up the iron. You just burn it, and that's your nine-fingered Howie.

All I thought about was like, is the ambulance going to charge too much? And should I bleed at the neighbor's house? Those were my first two thoughts. My wife will kill me that I'm bleeding in our yard.

Coming up, we continue our conversation with Howard Linzen, co-founder of Social Leverage, discussing what he calls the degenerate economy. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

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I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My extra special guest is someone I've known for too long, Howard Linzen. co-founder of social leverage uh one of the earliest seed investors in robin hood which is a chapter in my book oh wow let's do segment two and i have to start by asking about social leverage you've been doing this for 20 years yeah so how from the first seed fund you did to today yeah where you have a portfolio of 150 plus companies yeah how has this evolved first of What was the first company you invested in?

So the first company I invested in was so dumb. Cars Direct, 1998, the tippy top. As my wire left digitally my fingertips or whatever bank it was coming from, it was worthless. Right. Meaning like it was a series Q. Right.

But you were just early. Yeah, yeah, yeah. Pets.com eventually became Chewy. But I was late in that cycle. And now Carbano would have been.

Yeah, so I was the retail idiot. So I grew up, like I said, I went to ASU. You're going to be a furrier.

Right.

That's your chance. And a bad one because, you know. So the internet comes along. I fall in love with stock market because I had made some money at my first startup. And I had to be my own broker. And so Yahoo Finance, Jim Cramer, street.com. Like, they're still around. Right. So those were my onboarding. You were writing for the street.com.

They were the dominant, like, people who were younger don't realize. By the way, Yahoo's still massive. Kramer's still massive. I think the street.com doesn't get the traffic he used to. No, but Kramer's massive. Well, yeah, well, he's on TV twice a day.

But I'm saying this is 30 years.

Yeah. So that was my introduction to retail investing because I couldn't afford a Bloomberg. Still can't. So I can afford the drapes. I think you can afford a Bloomberg post. I could. I wouldn't know how to use it. Post Robinhood. I wouldn't know how to use it. Unless there's a phone line. What?

Huh? Charge. Especially with nine fingers. You need all 10 fingers for the terminal.

So I was inspired by you. The street.com had murder's row of writers. It's amazing. So a new investor. Yeah. I just would sit and wait for articles to come out. and yahoo finance so i was on the message boards perlman you like we were what was the first was on the message so cars direct was your first investment and 10 years later i got 10 of my money back after it being successful so so my first thing was a disaster what was your first successful investment so my first successful investment was a cold call that i made pre-internet in a company i probably talked about on the last show called the grip it was the so cute so i had the good fortune of being an hour before the internet before the internet an hour before the internet the thing before the thing was qvc i recall okay so before the internet still on tv qvc was the internet right meaning there was the whole of philadelphia was just old people on a phone saying yes yes we'll take your order and your credit card and if you were on qvc was a studio like this what was it we had a product called the grip i recall and it's in the qvc hall of fame so i made a cold call while i was a stockbroker to this kid thinking he was rich because back in the 90s it was just like the movie wall street you would get a newspaper and decide who you're going to cold call that right so i hated my job that was my first job out of college and i was cold calling to get rich clients and i called this kid and he ended up needing money like he was just promoting himself he reverse pitched you he he reverse pitched me right and And I had to cobble up $25,000 from my mom and friends. And I'm like, I'm in. And then he paid off his Amex with that $25,000.

By the way, every stockbroker and salesperson appreciates a good sales pitch. They're a sucker for a good sales pitch.

Well, he was promoting himself, and I was trying to sell him some, and he sold me on his company, which turned out to be a home-run company. What was the grip? He was a dropout, Mark Scattery, an unbelievable entrepreneur. And he had made this product with five balloons wrapped around this Siberian millet. And we were the largest Siberian millet orderers in the world in the 90s because we were making millions of balls a month by hand and selling them with corporate logos on them during the whole 90s run of pharmacies. And this was just a desk toy, a squeeze toy. Desk toy, but our genius was putting corporate logos on it. Nobody had done that before. Well, that industry was huge in the 90s, corporate giveaways, right, with trade shows and whatever. And we just got the right product at the right time. It worked. Oh, my God. We were just— How many did they sell? There's so many ball jokes, but they'd all get deleted here. We were the ball boys of the 90s. How many did these sell? We did $60, $70 million in sales. Get out. That's amazing. And the margins were crazy because, unlike retail, if you put Bed Bath & Beyond or Compaq on a ball, they own it. Right. There's no returns. Uh-huh. And so we just had this pet rock business where, like, Compaq would call us, we need a million balls for Comdex, and we'd just hire people, illegal aliens, and they would come into Phoenix, and they would all cut their fingers off by making these things. You made it in the States. We made it in the States. All our money was trying to figure out how to machine make these in the 90s, and we wasted so much money trying to, like, get humans out of the process. Compaq would order a million, pay you. Right, in advance. To start. Right. So we'd be buying cars. It was just a two-person company and like a bunch of like staff. And so we'd go out to lunch and buy cars because we were paid before we even started making the product. And so we were like – that's how I learned business, kind of like back to school. And you started this on QVC? No, QVC picked us up. And Mark used to go on TV. And back in the 90s in QVC, if it was selling, they just kept you out there like a cartoon character. They hadn't scientifically gone to the profit-per-second model because they were surprised at their success. So the grip appealed to, like, 70-year-old women who had carpal—like, they just like squeezing balls.

Little arthritis, little carpal tunnel. Little arthritis. Right.

So we created this $19 three-pack that had soft, medium, and—I swear to God, you can't make this up. And soft, medium, and firm. And QVC just kept Mark on stage all day, and the numbers would go.

Unbelievable.

And it was a miracle. That was our first success. So that was – so I was very much – that was my first internet success. Sorry, that was my first success. When did Social Leverage launch? So you and I both lived through this, the great financial crisis.

Uh-huh.

And that was an era of – so up until – 2007 2006 we lived in a world of financial leverage meaning and we know what happened at the end of that stacking you know excel came out people didn't have to my dad when i grew up with my dad in toronto if you did an acquisition it was like 700 pieces of paper with pencil taped together then excel comes out which of course nothing you know everything's made up at that point and one one sell-off can change the world but but we became a world the stacking things financial leverage right that was the banking era and the end of the financial leverage era came in 2006 2007 at the same time that social media came out so the the play on words was i want to do as an early adopter of social media i was like if an idiot like me so the idea was social leverage you can't implode with social leverage whereas it's financial of course well that was pre-canceled so i'm saying my thesis was oh my god an idiot like me who knows the right three people can just grow their networks for free forever right and so that was the birth of the the name social leverage it makes a lot of sense yeah it was just like a play on words some people will call me and go oh you guys do social investing oh it's the last thing i do meaning i'm not there's no impact it was just the play on words of financial leverage to social level i like it

but good point you can blow up on social leverage so now you're up to fund four fund six fund six wow i have the i and the v the goodness you passed on all of them i did we continue to do well until you come in soon as i come in it's over well that's when we shut down and and i famously um or infamously was an investor in stock twits and then when you pitched me on robin hood It's a line in the book. How that's the dumbest effing idea I've ever heard in my life.

You weren't the only one.

And it was. It was, I will, I will, I will. You're in the majority. You're in the majority. I own it in the book. And between you and me, I'll say, A, it was off brand. And B, no doubt that the pandemic lockdown helped them dramatically.

No, no, no. The thing about Robin Hood, because I was there from day one. And by day one, I mean it was another company, Kronos Research, before. They were like high-frequency guys and math guys. But you could only – this is about – you ask about investing. The life I've led, boots on – like just curiosity, your eyes, nose, ears, feet. You become a great investor by like touching, feeling. Right. You got to be on street level. The best investors are street level. I'm talking about private markets. Public market is a different thing.

So let's talk about private. Let's talk about startups.

No, so we were talking about Robinhood. So the great thing about Robinhood is it's not that I got it right. It's like if I didn't get that right, I'm nobody. Meaning I had to get that right. I was a Yahoo Finance user, street.com guy, E-Trade baby. You know what I mean? Twitter user, StockTwits founder. And if I had any nerve or any tech skills or any, like, real balls or whatever we're going to call it, I'd build my own brokerage. Like, I was there to do all that. But in 2010, even until Robinhood started, no one wanted to start it. Brokerage ideas were terrible ideas. So you have to understand that in 2013 when I saw Robinhood, no one in America – that's shocking that no one wanted to build E-Trade 2.0. Right. But what the venture capitalists were doing, they were enamored, and this is where venture capitalists, I always goof on venture capitalists, they were enamored with the wrong thing. At the time, it was like wealth front betterment. The VCs were enamored with assets under management, AUM. They felt like Vanguard was the one to disrupt. So everybody wanted to be the next. If you're a venture capitalist, you want to be the next Vanguard. And I thought that was flawed. I thought that was flawed because the margins are tiny. And you're never going to build something 10 times better than Vanguard. Meaning, wait a minute, what's wrong with Vanguard? Versus E-Trade, I'm like, it's s*** interface. You know, it's just ripping me off. And I was the right guy to get that pitch at the right time. So, of course, I had to do that deal. It would have been, that's why the podcast with the guy who passed, if I passed on Robert, I'd be a more interesting guest. So, how much did you put in to? well we did a hundred like we had it was our first fund so we were writing a hundred thousand dollar checks so it was a hundred thousand dollars at an eight million I thought it was expensive eight million dollars at an eight million valuation like at the time we were doing three million valuations so you know like I met them by Zhu and Vlad I flew up because they called me because of StockTwitch so they called me and said we have this app true. they were

They were out of money, and I flew up to Silicon Valley, and they showed up wearing Google Glass. Two idiots. Like, I'm like, immediately I'm out. Like, no one, you know what I mean? Remember that era? Glass holes is what everybody called it. I don't know what it was, but I was immediately like, what? And two dorks, but they showed me the app. They had this guy, Joe, who was their designer who had been at Facebook, and he showed me the app, and that's when I knew. It wasn't live. They didn't have their FINRA. They didn't have their broker. So it was really early. But because of Stocktoast and Twitter, I knew that if you build it, they will come. If you build a design, like Uber, if you build Uber for trading, okay, what people didn't get, again, was they were all betting. Hundreds of millions had been invested in Betterment and Wealthfront at the time. So the Silicon Valley was leaning into the Vanguard model.

Right.

So no one wanted to do the deal because who needs another brokerage? And by the way, building a brokerage, getting SEC approval, VCs don't like doing work. They don't like waiting a year. It's a grind, yeah. VCs do not like doing investment. Now they do because there's so much money in sovereign – you can get so much money and charge 2%. But back in 2013, it was like, show me something that's working. I want to be the Uber of that. So to take a year off and go get SEC approval, to go do those things, they deserve to be – It's laborious. And you had to wait.

You couldn't just go launch it and get sued. This is in hindsight. If you want to be the next Vanguard, wait, their secret sauce is that they have such scale, they can charge four bips and still make money. You're losing money at 25 bips.

And if you switch, you switch. But they have so much assets. So switching costs. So we could talk about this forever. I was in the right place, right time. Right people pitched me. Right valuation. Everything worked. I could tell you 100 stories of, like, everything lined up, and it doesn't work. Robinhood would have worked whether I showed up or not. Right. So we did 100,000. Now, obviously, we helped them tremendously with StockTwits. We were, like, responsible for hundreds of thousands of early sign-ups because StockTwits users loved the idea. Yeah, of course.

Free trading.

Free trading. No, but also the API, hooking in. You could slide right on. Right over. And trade.

Yeah.

It's pretty funny. Now, that idea in 07 when I had it, Jack and Av, like as a Twitter guy, I went to Jack and Av. Yeah, and Av. And Fred Wilson put me in the room with them. And I'm like, guys, what are you talking about Kim Kardashian taking a poop on Kanye West? That's not interesting. You know what's interesting? The president's going to tweet one day and the markets are going to move. Like this is literally my pitch to Jack and Av set up by Fred Wilson who was – they were like kumbaya, plane lands on a Hudson. Right. You know, we're growing our beards. No, you know, like, I mean, they were just the darlings. They didn't need ideas.

Well, it was the town center for the world.

No, they weren't massive. They weren't financial guys. They were kumbaya guys. They were builders. So my pitch fell on, like, who are you?

They didn't get monetizing Twitter through brokerage.

It's not about monet. They didn't understand what they had, Meaning selling ads against something that Goldman Sachs will pay infinity for. Meaning a new pipe where Bloomberg's charging $2,000 to get real-time information. Now, like Osama bin Laden getting killed, the futures – like in 08, whenever Osama was finally killed. 11, 12? I know where I was. Right. Because immediately I checked the futures and they had already moved. Right. And that's because of Twitter, right? Because some guy in Pakistan saw it and the futures moved. Right. Like, that's when it should have clicked. It's like, shut down everything, delay the feed 30 seconds, and you know what's going to happen? Goldman will call you Reuters, Bloomberg. They'll see that you're off by 30 seconds, and they'll pay you fortunes to get the real-time feed. Right. You and me, schmuck two and three, don't need real time. It's five minutes, right. So my pitch to Jack and Ev with Fred Wilson was like, slow down the feed because 99% of the population, and the way we're there anyways with AI, no one gets a real-time feed. Slow down the feed. Your phone will ring for the people that know that the feed's not in real-time, and they will pay you infinity to get the pipe. And they were

like, no, let's sell ads. So here we are. So you haven't talked about the cash tag, which I really want to talk about. Something StockTwits invented, a dollar sign, and then

AAPL is the symbol for Apple. So this is the Jack and Ed stories. So again, I didn't want to start company i just sold wall strip which you know which was my best work but again stupid but my best no personally i'm most proud of it you sell a company to cbs when you are literally an idiot

is the dream i think that's a fair disclosure yeah yeah like they said by the way as they

wrote as les mundas wrote the chat he goes i can't believe we're writing an idiot like this a check That was like that's the quote. I said, please write that like you and your book. Please write that you're so angry. So anyways, they had just bought my company. And literally a month later, I'm like, you made the wrong acquisition. You need to buy Twitter like Twitter to Quincy at who had bought my company at CBS. And I remember there was no iPhone yet. And Twitter came out and I thought it was stupid. You thought it was stupid. We all thought it was stupid. It was just annoying. Andy Swan, an old friend, was like, I get this. This is financial. Because, you know, at the beginning, we all had our BlackBerry. It wasn't even a native mobile app. It was just the web, and it was all venture capital. And my shtick in 2006, 2007 was I just peed at the Gramercy. So the VCs loved me. They were like, who's this idiot talking about his bowel movements? And then Andy Swan said, you know, this is like financial. This is like a new Bloomberg. Right. And I said, and I just, so, so the hashtag was the thing. And I'm like, it was all spam. Like, if you went to Apple, like hashtag AAPL or hashtag Apple, it was like, I went to the store and bought a green apple. Right. Like, that's literally what people were saying. It was so, now it would be like, let's nuke apples. But like, at the beginning, it was like, I bought a green apple. And I'm like, that's spam. So I sent Fred Wilson the first message that I'm saying like, and back then BlackBerry was the hot stock. And I'm like, I just bought dollar sign R-I-M-M. And Fred Wilson, who's the godfather of all this and was an investor in Twitter, sent me back a text and goes, this is genius. You need to start a company. And that's what sent me down the StockTwits path. Was Wilson an investor in StockTwits? No, because he was an investor in Twitter and he thought there would be a conflict. It's no conflict. I agree. But Fred is the OG. Why? Fred's the OG. So Fred's strategy is if he bets on one, he does. And I follow Fred's strategy. There's other people who spray and pray and don't care who they are. And 90% do that. But Fred was of the opinion back then is like, I work with you. There's going to be conflicts are a thing, like no conflict, no interest. He's very cool that way. But don't create conflict just to create conflict. So in his wisdom, he was like, you know, what's going to happen if you guys get in a fight and yada, yada, yada. So he politely backed out. But we were backed by good VCs. Raising money was not my problem. My VC should have said, Aaron, you know, it's not a good enough idea.

So, as an investor in StockTwits, I always wondered, why the hell did Twitter buy StockTwits? Well, they don't understand finance. They should have bought it.

You remember the last scene in Raiders of the Lost Ark? Yeah, of course. The whole movie is about getting. And then the last scene is, this is a very important, again, why media matters to investing. And it's just a black hole forever. Never to be seen again. The best tech companies like Salesforce, he understands corporate dev. Sometimes you buy something to kill it. Right. To say, and by the way, it's not Twitter's mistake. It's cost me a fortune. They're like my Newman. Twitter's like my Newman from Seinfeld. It's like Twitter. Like, you know. Now who's dating themselves? So, no, but what I'm saying is they're my Newman, like in Seinfeld. Meaning these people, it was a clown car, as Zuckerberg said. There's so many people that got rich. It was a clown car. Non-executing.

I love the line. Yeah, from Zuckerberg. It was in one of your recent posts.

Right, but Zuckerberg said it first.

Which was? It was a clown car, I don't know. That crashed into a gold mine.

Yeah. And so Twitter, and the real problem with Twitter was it was a financial product. And Elon knows that better than anybody in the end. Although he just. Well, he monetized it by stuffing it in a shell company. It's still like, it's an asset. he's made tremendous mistakes to think that Trump end-arounded the whole thing, meaning Twitter's supposed to be a real-time network. Right. They have to pull True Social. Right. True Social's worthless other than one guy who sits on top of Twitter, and you have to copy-paste his tweet. Like, so Twitter...

Well, on a different platform. Forgetting how

bungled the company is, the fact that they owned real-time and do not own real-time, and that I'm the schmuck that came up with the original like trump is going to tweet now obviously obama was president when i had this idea but like that the pipe matters and who is king of the pipe to think that trump beat elon at his own game is pretty insane he he is savvy in ways that people don't appreciate insane the truth social exists it's worthless but for one guy tweeting right Unbelievable. It's inconceivable. You bested my man of orange. So the poison cannot be in front of you.

So now, 2024, you come back to StockTwits as CEO. What motivated that? Are the early investors going to see an exit? What's going on? That's inside information. No, it's not public. No, so- It's not. public information, but it's not illegal inside information. No, Stockton's just like a corn on your foot. No, I mean, listen. Here's the thing about venture capital. Here's the thing about venture capital. Not everything should be venture capital. True. Okay, so I joke about this with my finger. Like, whose fault is it? Okay. I think Stockton's a great idea. The cash tag was a great idea. I'm very proud of it. Yeah, 100%. I'm not proud of having to run a company 17 years later. Not that it wasn't my dream when I started Stocktois, is to be sitting here answering questions about how am I going to make money. Let me bust your job. But you are very right to do this. So what I'm saying is I, and young kids need to know this, like math, not everybody gets to have a startup. Of course. Okay. Well, my venture capitalists, if they're as good as they say, and they are great, should have stopped me and said, this isn't quite venture capital.

Let me push back on that because I knew you were going to go there. I am. And your venture capitalists, and we know a lot of the same people, said, hey, there was a window to get out. You wouldn't have gotten an FU number, but you would have gotten a pretty good number. No, I never got a number. There was never. I thought there were discussions that just never came to fruition. There's always discussions.

Yeah. I thought you guys were on the one-yard line. I'm discussing it right now openly. There's always a price. Which camera? Camera two? No. So, listen, we have never – some things are only fairly valued for a second. Right. And some things stay overvalued or undervalued forever, as we know, from the markets. For sure. And I think StockTwits, I'll take full responsibility, we've always missed a window of positioning. Right. But the good news is StockTwits is thriving. Right. Yeah. It's doing well. This is a perfect – So, I'm saying like – Robinhood should really be the part. We were 10 years ahead of our time. If you think about where public – when I started StockTwits, retail investing was a laughing stock. And it still is to most institutions.

Much less so today than it was. So again, if you look at my portfolio – By the way, the private equity, private credit wouldn't be so hungry for retail investors if it was truly – They lead us.

They call me every day. Right. So there's two worlds that I live in. The world where retail doesn't take itself seriously, and private equity guys call me, CEOs of public companies call me to take, like, I'm in a crazy seat because I'm a goofball, but I am serious, you know, like, I am serious, like, I'm trying to be serious.

You used to be 60-40 goofball serious, now you're 40-60.

Yeah, it switches.

You're the new 60-40.

Yeah, I can laugh at myself, but I'm trying to run a serious business, right? Because it's been a long time. And we were just way ahead of the curve. Like, Jack and Ev didn't understand what we have. Fred Wilson understood it. right um there are very few people that understood very few people liked robin hood until 2020 and game stop then they like it for the wrong reasons by the way i don't like the robin hood that became like i'm not i call it the degenerate economy but when i invested in robin hood i didn't know the degenerate economy would exist i didn't know the prediction markets would exist i didn't know options would be their biggest product i was just wanting to see options are bigger than crypto for robin hood crypto tiny options is everything huh 90 of their profits will come from options any wow i didn't realize that how are they going to make money on zero commission other than options

people doing yolo trades payment for order flow margin loans that's just that's just media being bad media i'm going to tell you that the big shops like fidelity and schwab the single biggest line item of profitability are credit loans okay it could be i'm 90 i don't know i don't i don't No, I mean, at one point in time, it was over half at Schwab. I don't know what it is today.

When we invested in Robinhood, here was my thinking. First of all, I love the product. You've got to be a user of the product to be a good investor. I'm not the guy who's like, here's space check and here's a biotech check. What do I know? So the odds have to be stacked in my favor, first of all. But second of all, and they were. I was Yahoo. I was Yahoo Finance. I was you. I was blogging. I was doing everything. And they came along at the right time. But the pitch for me with Robinhood was not that they were going to make money. It was an $8 million valuation. At my event, people were like, how are they going to make money? I'm like, chill the hell out. They haven't even launched a thing yet. The point was Schwab was paying $150 to get a customer. To acquire, customer acquisition. And my thesis was, like Uber, Robinhood would pay zero. So if you get a million people, even if they're $4 in their account, that's a good arb. Those don't come along. Did I think it could be a $30 billion? I'm not so psycho that I thought I was investing in a $30, $40 million company. Billion. Billion. So, of course, I'm not that smart. But what I'm saying is I saw the ARB. And all they had.

had to do was deliver the product now it went way beyond my expectations that's the larry david by

the way you didn't give me that pitch the pitch was i'm sure i did the pitch was free trading millennials the whole next generation you're going to capture them before anybody else well i knew

that from stock to us i knew i'd capture them but if i say if i mentioned the arb trade people are like oh they're gonna have to raise so much money there was a lot of problems in hindsight yeah the

Yachtrade was why I invested. Would have been compelling. And again, it's a chapter in the book. I'll tell you a great – Hey, it's so off-brand for me.

One great story. Go ahead. Because this is just an investing story. So we're a very small fund. The first one was $6 million. Now we run $100 million funds. You cap it at $100 or – Yeah, I don't think our returns would be good. We like writing $1 to $2 million checks. I get that. Stay in your lane is something everybody hates saying. But I think in my world, unless you're fee gathering, stay in your lane. Like, people know what we do. You're going to laugh. I believe in that.

And I hate when people say it, but I practice it. That's an annoying way to say I disagree with what you're saying. Right. But what you're saying is, hey, here's our expertise. Here's my skill set. I'm a good monkey at this. I'm going to apply the area I know best.

So with ramen, so occasionally, and again, and I had breakfast with Fred this morning. We're talking about, like, you're a legend. Josh is a legend. Like I'm around, surrounded by legends because I've lived long enough. Okay. I've lived long enough and I'm curious and I'm nice and I call people to say hello. I'm a salesman. So who do I see this morning? Fred Wilson. Like who did I run to? Tim O'Brien. Like I'm friends with like people that have, you have signal because you have, you've been on the street and you have experience. Not maybe in space, but in what you do, you have signal. So with Robin Hood and I had learned from Fred Wilson, like if you really believe in something, and I'm not a poker player. Yeah, don't gamble. You got to go in as a VC. You have to. So Robinhood-

You're convincing me to throw money into fund seven, and that'll be the end of your run. But that's different. Every fund is like a crop of wine.

It could go sh**, depending on how, you know, we're wrong all the time.

Well, 2024 was a good vintage.

2020, 2021, terrible vintage. So when Robinhood was doing very well, but the two guys were like, it was not popular. All the VCs had committed to Betterment Wealthfront type model. So now they needed to raise another round. And I'm like, they wanted to raise. This is 14 or 15?

14. Yeah. I think that's when we spoke.

Yeah. So they were like, and I'm like inexperienced because we write one check. We don't have more money. So they call me up and they go, can you write us a term sheet? It was a very sophisticated way of saying like, you won't have to like actually invest. But if you come in, like we can shop, like we can kind of shop it around. So I'm like, dude, screw that. I want to invest. So over like July 4th week, I'm telling my partner, and it was two of us at the time. I'm like, let's just write an 11 million. They needed to raise 11 million bucks, and they wanted to raise it at some stupid valuation. It was 60 million-ish. And I'm like, well, we're never going to have to really write it. But even if we do, I can convince my friends, like, this is the one. And I called Fred Wilson. He goes, what are you calling me for? You know what to do. Write a term sheet. I go, but we don't have $11 million. dollars. And Fred goes, you'll find it. Just do it like a six-week, which is absurd. Now today, people write billion-dollar checks in an hour. But like, he goes, just ask for six weeks, right? So we, you know, whatever, you're typing it up, send him a term sheet.

Back then you had 10 fingers, so it was much better.

But, you know, 10 fingers, more errors. So anyway, so we write up this term sheet, We send it to them and they shop it as they probably index ventures. Jan Hammer, who's like one of the best investors, comes back with a term sheet of $11 million on $65 million. Wow. And like a five-day close. So like, you know, they got what they wanted. Oh, and by the way, indexing their term sheet, indexing their term sheet, like, f*** social leverage. That's a typical, like, who are they? Luckily, by writing that term sheet, Vlad and Baizhou did the right thing, and they carved out as much as we could. We couldn't even raise a million. So they carved us out. We put 800 grand in the Series A. If we had done the 11 million, I'd be a billionaire.

Right, 200x on the – Yeah. That's unbelievable.

No, way bigger at the peak. But we've had better investments.

You're not still sitting with the Robinhood shares.

A lot of my LPs – we distributed the stock. A lot of my LPs have not sold. I've sold it. Nobody says I don't ask. Our job is to deliver them. There you go. The the the cash.

I want to start with a quote of yours that I really love. OK. Quote, the whole world has become a casino. Thanks to A.I. and prediction markets, we are all more productive and. Degenerate now. Let's talk a little bit about the degenerate economy. Explain to listeners, what is the degenerate economy or the degen economy?

I don't like the word degen. So when I say degenerate, I say it in the humoristic way. You and I are degenerates. Because we'll buy a watch, we'll bet on a game, we laugh at degeneracy. We appreciate the art of degeneracy versus meaning laser eyes was dumb. right but degeneracy is an art form like speculation and i live i own and i joke that i own and operate two millennials and when you own and operate two millennials you watch you look over their shoulders those were your first startups no my kids yes but those were your first two startups the only startups that matter and did either of them merge yet do we have any m&a activity yet we need we need i'm not talking about dividends i'm talking about are they married No. So no mergers yet. No. My son was in a long relationship. Aren't you on the board? You should be chairman of their board. I'm on the board. I'm trying to get them kicked off. You're CFO also. I'm trying to get them fired. I'm trying to get medical checks to see if anything's working. So degenerate economy was born of this idea that I couldn't believe where we went, like with GameStop. Like, I was so stressed during the GameStop thing because I hadn't monetized their investment. I'm like, there was a weekend when Robinhood was worth $40 billion and it could have been worth less. Do you understand? Like, I wasn't rich. And I'm like, it wasn't even their, blame whoever you want. People lost their minds. Let me annotate. So let me just explain to you, if you have your phone. Go ahead. What Robin Hood perfected, which no one figured out, was like when we used to play pinball, there was always that kid who was so good at it. Crazy flippers fingers. Well, he could bump it without tilting it. Right. And he could just get the machine to dance for him. Tilt happened. Uh-huh. The app was so well designed. They couldn't execute, yeah. The app was so well designed that everybody pushed the same button at the same time. And it couldn't carry the... I remember when it was crashing. Do you understand? Sure. That's literally what happened. It was a design flaw. It was a design flaw.

It wasn't the design flaw. Nobody expected it to scale 10,000x over a week.

No, but if you push everybody to one button or another button, and then people come on and see me and say, push this button, and everybody's like, let's see what happens. And guess what happened? Crash, crash. Not to be repeated again. Hasn't been repeated again. And that's what makes the markets great. That hole was filled by the hole being created. Right. We haven't seen another thing like this. although recently with car avis but like gamestop broke the machine yeah and almost bankrupted the company right and and it was many lessons in there the most important was robin hood not in their hubris or anything they mistook success for a brand when you build a brand in four years not 40 years you don't appreciate that you have no brand value right And I'm like, no one understands this. Like, they were one of the first case studies in, like, what? It didn't deserve to be zero. Who knows all the things that went wrong? But I'm just some guy who's like, what the f**k? Right. I'm like, how embarrassing would it be if it goes from $40 billion to zero? And, you know, Galloway and all these guys were piling on and all these people piling on. I'm like, you don't even understand what's going on.

So, wait, let me tease this out of you a little bit. I thought you were going in a different direction, how degenerate the trading in things like GameStop and when Hertz was bankrupt and – or was it Avis? I don't even remember which. Some really foolish, reckless – and I think those of us with gray hair looked at it and kind of laughed because we knew exactly how that was going to happen. Yeah, the apes and all the A&C stuff. I hated it. But it doesn't mean I can stop it. That wasn't your concern. Your concern was, hey, here's a fire hose of new clients, new orders. This is the scale this company needs to become wildly successful. And they're just not prepared to deal with the sheer volume. And if this crash goes on more for a couple of hours, two days from now, this is a zero.

It was a zero. We can argue, I don't know the whole story, but I imagine someone called someone at the options clearing firm and said, you're bankrupt. And the VCs, lucky we're in so big, they had to put in more money.

They didn't have the reserve cash you need for margin trades of options.

We'll never know the real story.

So technically, SIBO is the counterparty on all trades. Yes. And they also own the platform. So they demand a certain amount of capital if you're going to trade X. Yes. And they're trading billions of dollars. They didn't have that capital.

So this is why my degenerate economy index was born, meaning I don't think AMC is in what's in my index, which is outperforming everything. SIBO is one of my number one position. Who benefits? So my degenerate economy thesis is finding the companies that benefit from global degeneracy.

You created this last year, two years ago? Three years ago. It's crushing. It's free. I just share it. Just to put some numbers on this, it's gambling, it's day trading, it's meme coin speculation. It's vaping, unfortunately. It's up 170%. The NASDAQ 100 over the same time period isn't even up 100%. It's up 94%. Correct.

You're almost doubling the NASDAQ. And I give it away for free, and I share the position size. Why isn't this an ETF? Because VanEck always talks to me. VanEck always is like, why do you want to be in the ETF business?

So, you know, you use ETF Architect. You know, I get it. Work with VanEck. This is a billion-dollar product.

Again, this is, I think, part of, like, you know, the age I'm at is, like, I don't want to be someone yelling at me that I, Kathy, as soon as I monetize it, it'll go to zero. Like, this thing will stop working. I love the idea that I can give it away for free. This goes back to the original social media. Meaning, what am I going to make? It's like, as soon as I start charging for it, the whole thing becomes stressful.

I took ads off the blog because they were annoying and ugly. And the amount of revenue it made was just too annoying.

You're saying the same thing. Yeah, I'm saying like, hey, man, I'm like, I got a little thesis. It's not that complicated. I love this thesis. I think people would be biased. So, TME, Hyperliquid now is in there. No one knows what Hyperliquid is. What's Hyperliquid? Hyperliquid is the thing, meaning today all I get pitched on are by the next Robin Hood. And I'm like, the world doesn't need another Robin Hood. But all they keep talking about is, you know, we've got perps trading 24-7 on Hyperliquid. It's the new salon now, let's call it, because I'm not a crypto guy. And I'm like, after getting 100 pitches of the same product and they all talked about Hyperliquid, but I just bought Hyperliquid.

And what's the market cap of that?

A couple of billions? It's like 12 people and one of the most profitable companies in the world outside of Singapore. Like the guy has no freedom because he's so rich. It's like a system. It's like a very fast chain. What's the symbol? H-Y-P-E. Hype. What a great symbol. Yeah. It's a token and you can buy it on Robinhood. I'm not promoting. I'm just saying.

Wait, so you could buy it on Robinhood, but does this not trade over the counter? You can't get it anywhere?

You can trade it as a, There's a DAT called P-U-R-R, again, I'm not recommending it, but I'm long a little, is a way that you can trade it over the counter. And again, you're betting on the fact you don't know anything about supply-demand. You're just, it's the system that everybody's trading on. Pure speculation. Pure speculation. On other people's speculation.

That's my thesis. This is speculation squared.

So anyways, so the degenerate economy is about picks and shovels. we can't stop if if a young person like my son and again i own and operate two millennials and and i don't want them betting my son will call me goes i can't believe i lost a 20 team parlay i go who are you even of my this is why i have to do a step in takeover of my son's company because i'm like take private are you talking to me like you asked me to vend my you 50 bucks to put on a 20 team parlay and you're complaining so idiotic so idiotic so i'm like trying to teach them not to be idiots you can have a degenerate economy you just need a little bit of math the problem is not enough kids have taken math and you also full circle on degenerate economy you have the wrong teachers right now i got brought on board by guys like you kramer the people who had experienced stuff fred wilson these kids are learning from chamoth and david sacks these guys were born of one generation they worked at facebook they worked for elon you could if you're not rich working for elon or facebook that would be interesting if you are rich and you're kissing the nipple of Facebook and that's not interesting. You were supposed to be rich. Right. Have some humor. A little humility or a little hubris. So my job is to teach my kid less hubris, more humility. Stop being a degenerate. Right. But the fact is you can't not be a degenerate when prices, kids are YOLOing because they can.

And it's frictionless. Frictionless.

And they'll learn. Some of these kids will learn how to be good put sellers or premium sellers. Very few. I understand. But the markets are very important, meaning having a price on everything is fantastic.

Coming up, we continue our conversation with Howard Linsen, co-founder of Social Leverage. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

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I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My old friend Howard Lindzen of Social Leverage is here. And when I say old, it's only partly because we know each other so long. It's mostly because he's an old man and is now 60 years old. years ago my wife and i i'm not a cruise person we were young we were broke we used to use this website called vacations to go.com you book last minute would cost you nothing like a week-long cruise through eight islands in the caribbean 500 bucks food and drink included booze included so as soon as they hit international waters the casino opens i am not a gambler we walk through And I just decide to look at the roulette table, not bet, look at it. And this is the difference between my wife, who taught fashion illustration and design, is a visual person. I'm a little more of a math guy. And I say to her, so we're watching 20 minutes of roulette, and it's just, it's so dumb. Yeah, I hate losing money. For random stupid reason. But I point out to her, look, the red pays or red or black or odd or even pay two to one, but you have zero and double zero. So it's not even odds. And then this group pays three to three to one, but it's one in four chance of winning. So they're making money and I'm going over all the math with her and she listens to all the numbers and says to me, I don't know about the ratios or the math. But all I can tell you is I see people – I see the croupier taking off a whole lot more money than she's handing out to gamblers. That's the takeaway. Be the croupier. Not the odds. Correct. Be the house.

So CBOE hit all-time highs. They're the house, yeah. Have you ever heard anybody on social media talking about CBOE? Never. They love that no one's talking about them. So the other thesis that I have is trends with no friends.

Uh-huh.

Okay, so I'm looking for trends because, again, I run a huge social media site, right? So if I have a choice between NVIDIA and SanDisk, everybody's talking about NVIDIA. You want SanDisk. I'm not saying I know much about SanDisk. We're just talking about Broadcom, same thing. Same thing. So on StockTwits, I can look for tickers that are trending with very few followers. No, it doesn't have to be. I don't like small caps, so I'm like 5 billion and above. No, I mean early.

I mean before it really goes up 10x.

So I, it's the one thing that Structwits has, and I have, AI, you asked me why I came back to Structwits, two things, AI, and the fact that, like, I can now code with cloud code, and so I can call bullsh** on engineers a little bit. Oh, this could take six weeks. I need it by today. Well, again, there's not today, but there's not six weeks. Right. Okay, so there's that, and then there's the fact that we have all this data, and we have a great community. So I wanted to come back and, like, see this thing through, and we're doing very well. the the the

The issue is now I can explain to people and I can pull out the data to show people trends with no friends. Meaning you want to find stocks that are trending that have very little discussion. Makes a lot of sense. Yeah, it's just intuitive. Meaning IBD, I learned on IBD, I love price relative strength. I've just added a layer to that that matches high price relative strength with low social. It's almost like the moosh of Vegas. I'm trying to find the stocks that know. Even though I run a social media site, I'm like betting on the fact that like they'll discover this in time.

You should talk to Ben Hunt and what he's doing with Perseans because they're too- Yeah, they have a narrative thing. But the combination of where the narrative is just starting to take up- Correct, typic. And where the trend is starting to- But I've been doing this for 20 years.

So I give it away for free. He's quantified it. Yeah, I hate the quant side. I just visually see it from years of being a non-quant. I went to ASU.

I don't even know math. But if you want AI to help you with this, the math matters. Yeah, I got to catch up with that.

That's awesome. But he also sees the world a little darker than I see it. I'm much more of an optimist.

You and I both. Yeah. But when I want to know what's the worst case scenario, like when the tariffs were first rolled out, not so much losing the finger, but his piece, the end of the Pax Americana. It's true. Was the end point where if this really goes off the rails, this is how bad it could get. Well, it's de-globalization. But he works out the details. He's great. Yeah. But again, you and I are both a little more of optimists.

I'm much more simple. Right. If I see something going up, that's my cue to look. And then if it's a certain market cap, and then I check stocks and I go, no one cares. I love that. Then I need to tell a story. Everybody needs to tell stories. Stocks are stories. And some people are great at storytelling, the Palantir guy. But again, the numbers eventually matter. And I'm trying to find companies going up, right? And that's not complicated. But then I have other layers to it. And I need to understand the catalyst myself. Like if it's just something I'll never understand, it's hard for me to ride the waves. So if I don't really understand and use the product, the odds of me getting scared out of a trade are 99%.

So let's talk about your – So that's my index. Let's talk about your startups who are becoming degenerates, your kids. Given social apps, zero commission trading, all the option stuff that's going on, for your kids' benefit, what sort of guardrails – I don't know if it's the product, regulation, educational – what do you wish was in place to protect them that isn't there yet? And let's also add, these are not minors. These are late 20s, adults out of school for almost a decade, real people. What guardrails should they have to protect them from their own worst instincts?

Listen, we put our negative hat on. It's like you can go buy bullets at Walmart. So it's like, what is a guardrail, right, in a world where you can buy bullets and everybody's got drones? So I'm like more like, okay, guys, if I hear that you did a parlay, we can't be related. So stop betting. Betting is different than investing. So if Shane at Polymarket, and they're partners of ours, if Shane or Tariq at Kalshi had pitched me those ideas at the same time that Robin had pitched me their idea, I would have passed. Why? I don't bet. I think it's stupid. Okay, like I think it's funny. And I think prediction markets are news better than the New York Times, no offense, because I like prediction markets because I don't have an opinion. I just look at the price and I go whether I believe it or not. I think that's the genius of it. But if Pauly Market and Kalshi went out to VCs and said we're the new news, their valuation would be a dollar. Right. OK. So we know the real story. They can't tell what they really are good at, which is news.

And by the way, they're not great at news. I understand, but neither is news good at news. It's probability of something happening.

But I'd rather not read someone's opinion. I don't need to see Elon's finger on the news because that's not the real story. Give me the numbers. I know it's fake, but I got a number. If Mondami isn't 90% and my daughter's mad, I go, Rachel, here's what you do then. Bet the other side. You'll make eight times or put— It's 10 to 1. 10 to 1. But I would bet money on Mondami. And if you really want to change how you think about the world, go help somebody on the other side who has a chance. Go put in the time. Go help Mark Cuban if you really want to be.

I love what he's doing on the health care side.

But what I'm saying to my daughter, I said, call Mark. I'll get you in touch with Mark. Do something. But just complaining about the numbers that you see. And the numbers were right. Whether they tipped it in a – again, I don't want to get in all like the fraud and all the fake stuff about it. But the numbers are much easier than reading an opinion. piece i'm gonna can i tell share something fun yeah so there was some of the early bets about outcome of the war and different events happening and i said in a quarterly call hey i don't really know uh who's putting we don't know who's putting these bets in yeah but if you stop and think about it if you're negotiating with another side this being the psyop because you spent half a million dollars to move uh the outcome of something that's the least money the department of defense will ever spend and anybody on their side is looking at this oh they're they're really going to put boots on the ground that's look at the track record here here here's a a wallet that's 10 for 10 oh my god we have to stop and think about you don't really know who's using this who's betting this who's manipulating but we didn't know that guy who got arrested that was a throwaway That's a false flag.

It's still better than Russia and China using our social media. Oh, my God. It's the worst.

And North Korea and Iran.

Yeah. So I'm not saying I'm an investor in Polymark and in Kalshi personally at crazy valuations because I wouldn't have invested. Like I just chased it in SPV personally.

The co-founder of Kalshi, the woman, what's her name? I don't know. But I know it's a woman. I just can't remember her name. No, she was a guest on the podcast. Was she great? She was really good. This is years ago. I'm not- This is three years ago. I should never even thought to put money into it. So that's what I'm saying because I don't bet. It sounded more academic than anything. It was academic. Yeah.

It still is because there's very few people using these products. For all the free press, it's like Twitter. There's very few people using Twitter.

Well, Twitter is starting to drain at this point.

No, but I'm saying at the beginning, it had a lot of power even though there weren't that many users.

It was a fraction of Instagram or TikTok. So production markets are the same.

It's an important fraction. It's a fraction of the news. But I'd rather my son and daughter go to page two of Polymarket because you know what they're going to see? News that they wouldn't ever look at in the New York Times. They can go look at the election in Peru and now at least they'll know the names.

Or Venezuela for that.

Or Venezuela. So I'm super bullish for different reasons on prediction markets. And I know there's like – obviously I have money on the side.

And this fits right into the degeneracy index. It fits in completely. How long does the Degen Index run for? Is this a short-term thing or does this have legs?

That's why I don't want to charge for it because I think I'm a – because Google and Apple are my biggest positions because they are the rails for the degenerate economy. They are the front-facing tool of it.

Apple because of the phones and mobile.

And Google because of the phones and YouTube and App Store. The casino games all run on App Stores, the free games that you have. They make a fortune off that Apple. Why not Amazon or Facebook? Amazon just added at the beginning of the year because of robots, Axon's in the portfolio.

Not because of the Amazon Web Service because of robots?

Yeah. I mean, you can't not own Amazon at this era in the degenerate economy because they are the center of it. Which robot shops do you like? Again, you could argue it's a degenerate economy, but you have to own Amazon. Any of the robot builders you like? No, because they're too early. I'm a personal investor in a few. Such as, give us some names. Aptronic, which is just massive. But again, it's a personal investment.

Do you have any interest in what Elon is doing with Grok? Yeah, but it's a holding company. Like, I don't know what the position is. No, it's kind of random. Meaning Tesla is a holding company for everything but SpaceX.

Or is that going to be the entity that goes public for SpaceX? I thought it was SpaceX. No, but I'm saying to SpaceX, why does he need two tickers? Like, again, I don't understand what the final being is. So why do I need to own some Elon holding company? I think that's stupid.

So you're betting on him and you don't think he's- I'd rather bet on something I understand. Okay, I'm with you. I don't disagree. I'm trying to figure it out.

Yeah, another recent ad is it's already doubled as Clear Secure. You know Clear when you go through it. It's just such a clear. So to me, if the world's degeneracy, you need security. Much more security. So Clear's been a home run. They don't have a lot of tech, but the great brand.

Yeah.

I thought they have tech. I think they license a lot of the tech.

Oh, that's not theirs? They don't own it?

Yeah. So again, once you dig into a story, My conviction comes like how much of this they own, but they're a hell of a brand. The company's been around forever.

And they have the relationship with FAA and the airports.

And they can do so much more around stadiums.

The brand matters. What are you talking about? You go to watch a Knick game. It's clear. It's clear on the way in.

That was my bet. It's just a clear trend. No one ever talks about it, too. So it's a massive uptrend. Broke out, and you never hear people talk about it. I like that.

If you use either Chase Sapphire Reserve or Amex, I want to say Platinum, you get a credit towards any travel, and Clear is just an automatic. It's a no-brainer. Yeah. What is it, $150 a year? It's fantastic.

My son would call me because that's the greatest gift he ever got, man. I'm like, wow.

When a 20-year-old knows something and an 80-year-old knows something, those are good trends. You know, that's a brand.

Yeah.

When just a 20-year-old knows it, not a brand.

Maybe it catches on, maybe it doesn't.

Yeah. CBOE, I love it because they power the whole thing. You can't do this without CBOE, CME, the Merck, you know, the New York Stock Exchange.

Let me ask you a question, a direct investing question before we get to our favorite questions that I think a lot of investors have a hard time with. I started on a trading desk, so I'm okay with losses. It's a given. But if you say to somebody, I want you to put a little money into these 10 or 20 stocks, half of them are going to go out of business, maybe five or a break even, you'll make money on a couple, and maybe one's a home run. How do you deal with that really fathead, long tail? You're not a math guy.

I'm so into indexing.

No, I mean on your private seed state. Like most of the seed investments you're going to make aren't going to give you a return.

It's a great question. How do you deal with, oh, I'm wrong all the time? I'm just bearish on my industry, right? I never, I believe it was a moment in time with Zerp. I think it got the country through its unintended circumstances. We live in all these unintended circumstances. Consequences, right. Yeah, unintended consequences, sorry. By the way, now that you're 60, that happens a whole lot more. I am wealthy, just born at the right time, a lot of unintended circumstances. Zerp is a good thing. Right. I'm not saying I shouldn't be ashamed.

If you have assets, if you're working stiff, like I used to be, it was tough.

Yeah. S&P is at all-time highs. Cash level is at all-time highs. If I hear those two things together, what do I think of? Inflation. Right. There's never been a better time to have assets. Right. It doesn't mean I don't know when it's going to end. Right. I have cash and stocks. It's a double whammy. So I'm lucky. I am so bearish on what I do for a living, meaning what value do I add in a world of 6% interest rates, tying someone up for 10 years when I can go buy Sandisk in the public markets and get 6,000% in a year? I'm not saying I'm smart enough to hold these things. But in a world where Robinhood and 1,000 Robinhoods are going to bloom, if you're asking me my biggest bet, public markets. Do the work. You have an analyst in Claude. Right. You can go see beaten ups. No one's following any stock. Everybody's momentum investing. Go find 10 companies. Why would you do a startup investing? Every kid wants to be an angel investor. I'm like, dude, do it in the public markets. You have liquidity and you're not locking up your clients for 10 years.

But you're not answering my question. Okay. Which is, how do you as an investor deal with the psychology of knowing most of your seed investments aren't going to work out? Is it just the nature of the beast? No.

Or does that weigh on you at all? No, I think it aligned with how I thought of the world. As someone who believes their high integrity, who wants people to believe their high integrity for my kid's sake, the integrity of telling my investors that up front is the release. Meaning, I'm not telling my investors we're going to be 90% hit rate. If you give me money, you're going to hate me. Because you're going to think the idea that I love is the dumbest idea, the Robin Hood. Quote, unquote. Yeah. Dumbest idea I've ever heard. You are betting on me to hang 30 pieces of art in Howie's gallery, the Larry David gallery. And you will pick – if I gave you the choice to invest in all 30, you would pick the two that went to zero. So you're betting on me to see the world my way. And then I'm not telling you we're going to make 100 times our money. But my job is to find one company that's a hundred bagger. Okay. So I have to know math. I have to do this. I have to have – just get yelled at by my LPs when they read our quarterly letters and go, that was the dumbest idea. I'm like, you're right. Like, I'm embarrassed. But our job is to find a Robin Hood, and we found many of them. You know, LifeLock, Robin Hood, Beehive. We just got one called Alpaca. Again, a trend with no fame. Alpaca powers a thousand Robin Hoods around the world. They're like the modern apex. So I'm saying, like, our job is to know what we know, take crazy bets, and sell that to our LPs. It's like, you're investing for 10 years. This is like, you know, it's not as good as it was in 2013 when rates were zero. And now it's a different game again. And I'm thinking, like, you've got Claude, and you can analyze the stock in, like, three seconds. I'm like, everyone's a CFA all of a sudden, if they want to be. What a great time to be a public market investor. And yet everybody wants to be a private investor.

It's so funny coming from you.

Yeah, no, no, in 2020, I've been writing about this since COVID. It's like, public markets are amazing because there's so many. Stupid people making dumb bets on Robinhood, and dislocation is everywhere, and it's only getting worse. And the degenerate economy is going to continue driving this theme. Yes, and I think most people should index, but everybody should learn how to pick stocks, too, in this era.

I got you.

Yeah.

All right, so it's almost midnight. I only have you for a few minutes more, and you have to end up at your event tonight. Cash tag awards tonight, yeah. Cash tag awards.

Breaking news, Octoberfest, October 6th, coming back to New York. That's our big event. That's exciting. Yeah, 1,000 people on the West Side.

I am looking forward to that. October 6th.

If you want to come, hit me up.

Let's do our speed round. Five questions. Two hours. Ten seconds each. I'm going to jump right into it, starting with. Boxers. Who were your early mentors who helped shape your career?

I think part of it, I hate saying this, I didn't have good early mentorship. So I really take pride in mentoring other people.

Who were your later mentors? I hear Fred Wilson all the time.

You, like people that I discovered, like the mentorship came from the community. Being the mentor led me, like StockTwits, being a giver opened me up to get mentorship. I think young kids are not getting good mentorship.

So just pure karma. Karma. I love that. What are some of your favorite books? What are you reading right now? I know what you're reading next. What are you reading now? Yeah, I got your book. I don't read. You're on flights all the time. What do you do? Just movies?

I'm so addicted to like HBO, Amazon. So you're watching series. Yeah, I built, I'm just very into content. That's my next question. But hang on, so you're asking books. I still love the classic, Shoe Dog for Business, you know, Phil Knight's book. I loved Agassi's biography. I like stuff. I just, my brain doesn't work with books.

Huh, that's really interesting. Tell us what you're watching on Netflix, HBO, Amazon.

I just re-watched The Nick. Have you watched The Nick on HBO Soderbergh? Why does that sound so funny? Oh, it's about the 1900s, the Knickerbocker Hospital. No, I did not watch that. Best show. Really? First season. It's like surgery wasn't done until, like, barbers used to do surgery in 1900. Right. All the rich oil guys started backing hospitals, and that was the original tech. Surgery was tech. Uh-huh. And it's just an incredible period piece about the 1900s in Soho in New York.

Huh, I'll check that out. On HBO.

Give us one more. There's very little good stuff on TV. I think Rooster's pretty good. Can I tell you something? On HBO.

You have that backwards.

There's too much good stuff. I think I've seen it all. Have you seen Landman? Great. But that's more like Harlequin romance kind of series. They're fun to watch, and the kids like them too. Okay.

The Nick you'll love because it's just periopee. Did you see Three Body Problem, if you want something a little more? No, but that's sci-fi, I think.

I don't like sci-fi.

You don't like sci-fi? No. So you didn't watch The Expanse?

No, I didn't like that either. I try it, and I never get into it.

Huh. That's interesting. I like Degenerate stuff. How do you feel about Spy, that sort of stuff? I love them. Killing Eve? Killing Eve's good. It was great.

I like Spy, I can rarely follow it well enough. Night Agent? Have you seen Night Agent? Yeah, it was good. Wow.

Yeah. How about any of the British period pieces? I love Britbox. I watch Britbox.

All right, so The Crown, Bridgerton. Not Bridgerton, but Britbox's a great channel. Yeah. There's that Criterion for old movies.

If you have BritBox, go back and watch – what was the name of that show? There was a show that came out around the same time as Friends, Coupling, and it has teeth. I mean everything from the 90s is a little dated, but whereas Friends was kind of milquetoast and mushy, this has a sharp edge and it's British. So it's nasty and funny in a way that only the Brits can do.

Okay, yeah. So I'm a media fanatic, but not like I'm weird. And I'm so bullish on YouTube, Apple TV. YouTube is just great. I just love YouTube.

All right. So final two questions. What sort of advice would you give to a college grad interested in either becoming a seed investor or a startup entrepreneur?

Well, I think there's no shame in being a number two, number three, or number four. So chief of staff is the new CEO. So go be someone's chief of staff. Like, don't worry about pay or title. Worry about finding something that's working this way. It's much easier to go work for a company that's just working. So go, like, ignore the title. Low-end job at a— Ignore the salary. Find a rocket ship and attach yourself, whether it's Manscaped. You're going to learn more. There are going to be smarter people around. And there's going to be, you know, less aggravation, more work. But hey, like if you're really serious. But you've got to grind it out for a second. I tell my daughter, it's like, if you're really serious about this, it's going to take a lot of work. But go do it. If you're not.

serious be a socialist like it's okay but like don't commit don't fool yourself like go work for a rocket ship otherwise who are you talking to so like there's no room anymore for these kids that like if you want to start a company do you know it's 24 7 right and if you and no one's going to like you and if you want to be a number two do you know what it takes to be a number two so i'm like be honest but like go work for a company that's working and our final question

What do you know about the world of venture and seed investing today that would have been helpful 65, 70 years ago when you were first getting started?

No, I think I luckily got the right mentorship and entered at the right time. I think you have to do it for a while. You've got to get a crop. Like if you're going to go do wine or weather matters, and same with tech. Like what matters with tech is you have to – if you were of the Google Glass era, not much worked. Right. If you were in the BlackBerry Fund 2008 – No go. No go, baby.

Unless you could have been an early investor in Apple or when they were public.

I think the public markets are underappreciated because seed investing became cool because of Zuckerberg and because of a few of these rocket ships.

See, I thought seed investing or venture investing really became cool in the 90s and then in the 2000s kind of faded.

No, it's never been more loved.

Today.

Oh, I go see these young kids. it seems like they know nothing and they all want to be venture investors. I'm like, have you ever bought a stock? You get wounded day one, stock drops 20%. Go open a Robinhood account and learn how to invest. If you don't know the public markets, what are you doing in the private markets? Got to graduate to private. Yeah. I think the guys who were interesting to me, and I'm not saying they still are, the crossover investors, the people that knew the public markets and then started doing private. And I think that was my edge. I knew how pricing worked. Whether I was right or wrong, I understood how markets worked in the seed investing. The prices made sense to me relative to public markets. Now the prices in private markets make no sense

to me. Howard, it is always a blast when you come in. You're a bucking bronco. I never know where we're going to go. You are not Larry David. You are the Zach Galifianakis of finance. He was just on Conan. I should put two ferns in here just for your arrival. Thank you, by the way, for for being so generous with your time and good luck at the cash tags awards tonight if you enjoy this conversation well check out any of the 600 we've done over the past 12 years you can find those at itunes spotify bloomberg youtube wherever you get your favorite podcasts uh i would be remiss if i didn't thank the crack team that helps put these conversations together each week Alexis Noriega is my overworked video producer. Sean Russo is my researcher. Anna Luke is my podcast producer. I would also like to just drop a little piece of information. The paperback of How Not to Invest comes out today. By the time you hear this, it'll be out already. What else do I want to say other than- You look good. Thanks. I'm Barry Ritholtz. You've been listening to Masters in Business on Bloomberg Radio.

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