Martin Shkreli Breaks Down the Collapse of Situational Awareness
30 Jul 2026 · 44 min
In this hour‑long podcast, host Jordi Hays and moderator Speaker A sit down with former hedge‑fund manager Martin Shkreli to dissect the rapid implosion of the AI‑focused fund dubbed “Leopold”. Shkreli frames the event as one of the most chaotic months in Wall Street history, comparing it to past liquidity‑driven collapses such as Long‑Term Capital Management and Amaranth. He explains how rumors of distress surfaced mid‑week, leading to a cascade of short‑selling by other funds attempting to “shoot a fund” – a common practice of selling shared positions to accelerate a liquidation. The conversation moves through the fund’s structure: roughly $45 billion in gross market value, 4× leverage, a large exposure to Anthropic (≈$10 billion) and other AI‑related equities, and a thin equity cushion that would be wiped out by a 25 % drawdown. Shkreli details the role of prime brokers, noting that they earn a spread on financing and can rehypothecate assets, making leverage their “best friend”. He describes the bidding war among Jane Street, Millennium, and Citadel, highlighting Citadel’s historical role as a market‑maker and rescuer in distressed situations. The discussion also covers fund‑level governance – high‑watermark and claw‑back provisions on the 2 %‑20 % fee structure – and the difficulty of unwinding illiquid AI stocks, including the “advertisement” process, market‑maker IDs, and the need for a buyer with multi‑year liquidity. Shkreli shares a personal anecdote about over‑betting, introducing the Kelly criterion and a portfolio simulator that shows most traders (retail and institutional) over‑size positions, leading to busts. He contrasts this with a low‑turnover, cash‑heavy style he observed at a former SAC Capital manager. The episode also touches on journalistic timing, the tension between early disclosure and protecting sources, and the broader cultural shift of AI‑driven capital flowing from the West Coast to traditional Wall Street. The conversation ends with reflections on leverage mechanics, the future of the fund’s LPs, and the broader market’s potential for a prolonged correction.
Chapters
Let's bring in Martin Scrawley to break it down for us. I believe he's here. How are you doing, Martin? Good to see you again.
Hey guys, I'm doing great. How are you? Oh, perfect. Perfect.
How's your last—
take us through it.
24 hours.
Last 24 hours been like for you?
It's, it's been interesting. I do invest myself, so it's been a, it's been a probably one of the craziest months in Wall Street history. I was talking to some friends last night about Long-Term Capital Management, uh, Amaranth, uh, other famous liquidity-driven blowups. And, uh, this is up there. Uh, and, um, yeah, it's just a really crazy thing. We had heard rumors, um, sort of mid-last week, and then they really started crystallizing, um, last night, um, and this morning, obviously sort of a fait accompli. And I actually think they did a wonderful job of of keeping it relatively quiet. I think some players were already positioning, say, early in the week, Monday, Tuesday, looking to do what my old boss Cramer used to call, you know, shooting against a fund. So if you know somebody has to liquidate, the best thing for you to do, unfortunately, sadly Darwinian, is to go sell all the positions you have in common and go start shorting everything they have. And it accelerates the the sort of downfall as quickly as you can. And this is a very common practice when these things, you know, happen. Certainly not something I had overlap positions with them. So certainly nothing I would do. But no, a wide number of funds that were shorting all these stocks hoping to cause a panic and a crash.
How do you trace back the start of this correction? Is it the war? Is it oil? Is it jitters around open source or just hyperscaler capex. There's so many different narratives around why the AI infrastructure trade, the bottleneck trade might be weakening. At the same time, it feels like there's some really solid progress and the models are progressing along like pretty like as expected.
Yeah. Yeah. You have the labs having some of the best months in business history of any companies ever.
Yeah.
But then all the infrastructure correcting.
Yeah, none of that stuff matters. The only thing that matters is the propensity of the buyer and seller to buy or sell. And what you had happen was the smart guys get in early, start buying, see the prices go up, buy some more. And then less smart guys take note and say, I want to do that. I want to be up 400% this year, too. Guys like me started buying right near the top. I was just like, hey, this is great. I love memory. I love bottom nuts. And, uh, and then, but, but the weakest hands are buying at the top, so they're also the first to sell.
Sure.
First to panic.
Yeah.
And it just creates this, like, you know, every bubble's sort of the same. You have this euphoria, this peak, and then, you know, everyone sort of panics at once. And, you know, the fundamentals basically don't make a difference. You know, I think today they drive the marginal buyer and seller, but the 80% or 90% of the assets, shareholders don't change hands. It's that 5% of the margin that's deciding the price. And if that 5% is in the state where they're levered up 3x or 4x, as we heard SALT was a 4x levered fund, which is— that's a lot of leverage. A 25% drawdown takes you out of business. Interestingly, we heard that 3 firms were bidding on the assets. So Jane Street, Millennium, and Citadel were sort of brought in in a closed, closed circle sort of late Friday to bid on the remains of the firm. And we got offered a look at $100 million of Anthropic stock, which we were puzzled, puzzled by. You know, sometimes you see these SPVs, sort of interest comes across. Here and there. And we thought that was interesting. I sort of raised my eyebrow and said, is that Leopold? Because sometimes when you want to sell $4 billion or something, you don't come out and say you want to sell $4 billion. You come out and you say you want to sell $100 million of it. And usually, a guy who wants to buy $100 million is enough to buy $500 million or more. And you sort of feel them out and say, here's $100 million. OK, do you want $5 billion by any chance? And then your eyebrow starts to raise a little bit that maybe he's got even more. Now, of course, this is a really odd situation. So we heard Millennium did put in a bid. Citadel's bid was better. I think Ken wants to be the guy that everyone goes to when they're in trouble. And that's the— Buffett is getting older. This is not the kind of stuff Buffett wants to do anyway. But Citadel did this in the Amaranth deal. When Amherst blew up natural gas futures, I think Citadel took that portfolio. And virtually every blowup in finance, they've come to the rescue.
Well, you have Enron, where they just raided all the talent.
Yeah, they wanted to do it at Enron as well. I think they just sort of— Ken is a very smart guy. He sort of shows up and says, how can I be a partner to the Goldmans and the Bank of Americas when they need to get out of a really risky position, they basically take over the book. So I'll give you an example. You're asking the question. So let's say you're at $45 billion, to sort of try to trace this back. And $10 billion of that is in Anthropic, from what we understood. So you have $30 billion of cash in your bank account. And running 4x levered means you have $120 billion gross market value. So if your GMV drops, I don't know, 25%, that doesn't sound so bad at $120 billion. Maybe that's, I don't know, $30 billion. So you're down to $90 billion. But that's not your equity. So your equity drops from $35 billion to $5 billion. And no prime broker is going to let you keep $90 billion of gross market value, because once you dip your equity below zero, it's their loss, not yours. And they're not going to lose a penny after Archegos and after these other blowups. That's not their job. And they have the right to take over your portfolio, which is something I hope nobody ever has to experience. But they basically call you in and say, listen, these are our assets now. We're going to decide what their disposition is going to be. And the rumor is over the weekend, he contacted about 10 parties to place Anthropic in an effort to shore up liquidity, selling the Anthropic stake for allegedly the offer was at $1.1 trillion equivalent market cap, which, you know, I think roughly where it's trading. And, you know, it's unclear whether that was sold or half of it was sold. It's what we reported, that, that half of it was sold. It's still a little unclear who bought that. What's happening exactly, but that's, that's the best we've got. And then, you know, when it came to, um, the public, you know, book, it does sound like, um, you know, the, the buyer of that book basically got a, from what we were told, a $3 to $4 billion insta markup. So they basically now have to work them, they have to work out of $3 to $4 billion. Yeah, uh, more than $3 to $4 billion, quite a lot more. But in essence, if they work out of these positions without disrupting the market, they'll have printed $3 to $4 billion on the trade, which is unusual and interesting trade, but really exciting. One of the parties reached out to me last night, one of these 3 parties, interestingly, after my reporting. And they said that, in essence, in sum and substance, yes, Leopold flew a little too close to the sun, and your numbers are are a little off. And I asked what direction, and they wouldn't confirm or deny. I received a lot of pushback on the reporting, to your point, privately and publicly, that it's not so bad, and that he's only down 30%. 30% you can kind of live with. But also, if Anthropic hasn't changed its mark, that means you were down 60% in the public book. And if you're forex levered, You know, that means you're sort of down 15 on the public book, which sounds too good to be true if you're trading these stocks. They were down like 15% a day.
Yeah.
So we've also heard the other, other AI funds are hurting, maybe not as much as in trouble, but, but certainly hurting as well.
Where does the fund go?
He gives some good— he gives some good cover to all the funds that were effectively copy trading him.
Oh, sure.
Maybe even being more risk-on and later to these positions. Because they were— they're naturally just late if you're trying to copy trade someone and you're trying to catch up, you know, you're trying to catch up. Yeah, more leverage. You're, you're, you're coming into these trades way later. Um, do you, do you recall, uh, like, how did you process Ryan Jacob in, in around the year 2000? Because you were at Cramer's firm, I believe you joined maybe right before the Ryan Internet Fund started collapsing.
Yeah, there's also the Amarin Fund. There was a fund in the '60s called the Manhattan Fund that Warren Buffett criticized for being the go-go kind of like the, uh, fund was run by a guy named Gerald Sy. And so like every generation, you've seen the memes about Cathie, you know, um Every generation has it, the guy that believes in that cycle and goes balls to the walls on that cycle. And look, I have a lot of respect for somebody who's willing to do that. I used to tell a friend who did the same thing, he followed this trade, but he was very early. So he had Leopold-like numbers. And he did hedge it at what sounds like close to the top, so a miracle trader, best trader I know. And I joked with him, I said, you know, if Leopold sells at the top and turns short, like, I will absolutely adulate him as the greatest of all time. It's just that, you know, usually when you're so spellbound by that narrative of whatever happening, in this case, AGI, you know, there are people out there that say, look, AGI is here slash coming. When it comes, the entirety of finance is not relevant anymore.
Yeah.
You know, we might as well just run it up and kind of see the end of days this way. And of course, there's some guy sitting on a trading desk at Goldman Sachs. You're like, these people are fucking nuts. You know, it's just the stock market. No big deal.
Did you— given, given that Leopold had, had been at FTX right up until the, the, the fall, did you think that maybe as, as risk-on as he was, like maybe he was like, you know what, I just, I can't go through that again. He wasn't necessarily— he wasn't necessarily directly tied to any of this sort of nefarious activity. At FTX, but he did have to viscerally experience it and I believe resigned the day of the collapse. And yeah, I would— I just would have expected to not like run it. Yeah. To run it back like so quickly. You would expect even like, you know.
Yeah.
Go and do it. Have a normal, you know, great career for a decade or whatever. Then maybe come back to leverage and be like, I'm ready to dance again.
But There's a lot of questions. One question is, what's his carry? A lot of firms in the hedge fund industry, believe it or not, they have clawback provisions for carry.
Like high-watermark provisions, right? So you have to clear something?
Sure. Everyone has a high-watermark. But what's increasingly happened is a carry provision where you have to return the 2 and 20 you earned if you have a severe drawdown, which could actually end up being a tough situation. As you guys know, the fellow is getting married this weekend as well, which is a little bit of tragedy with a little bit of triumph mixed in. But obviously, when this happens—
But how common are those clawback clauses? Because you have to imagine in this fundraise, he had massive, massive leverage.
Demand was very high.
Demand was very high. That feels like a term that—
The numbers were so good.
It's a more institutional thing. And speaking of which, obviously, the guy basically had no experience. And again, in times like this, nobody wants to grave dance. And I'm not doing that. But I had some institutional friends, one of the biggest fund of funds in New York, for example, who passed on Leopold, basically laughed at him and said, there's no way I could invest in this. And of course, he goes on this tear, makes like 20x or whatever it was since inception. And does fantastic. And he feels sort of sheepish, but ultimately somewhat vindicated after all of this. So you did have a manager that had no experience, kind of a long-only or extremely long-biased, starts to do privates, which for many hedge funds is kind of the death knell. You know, when hedge funds put on their VC cap and try to do what those guys do, it often doesn't end well. And that goes back, like, 50 years, basically, of hedge fund history. And very few people have been able to do both. And the other thing I'd point out is we're going to see July numbers very soon here from, from quite a lot of hedge funds that I think were in the same trade.
Sure.
And so this, this is not just Leopold's $100 billion gross. It's like that times maybe 5 or 10.
Sure.
And the market— well, the market's liquid, but that's a lot of downward pressure in a few weeks. And, you know, it's amazing to see this all compressed in a month, whereas like the dot-com bubble took 3 or 4 years to patiently go up and patiently go down. Seeing that compress instantly is interesting. What's going to happen next is really going to be fascinating. There's some theory out there that we see all-time highs again now that all this liquidity is out. And there's other theories there that we actually were just having this nice, big downtrend, and that this liquidity pop will fade, and we'll be back down further and further. You know, nobody knows what will happen, but it's certainly— while you're right that, you know, the Anthropics and OpenAI are having record business results, so is Microsoft and Google and Meta for that matter. There's still, I think, some more discerning questions about is, are, is this CapEx investment worth it?
Sure.
You know, they rewarded Microsoft for being prudent. They punished Meta and Google for not being prudent. So one wonders what, what the future will bring there. But Yeah, about as crazy as things have gotten on Wall Street in many years, probably at least since FTX, and certainly crazier than the sort of Tiger SoftBank venture boom of '21. And then, you know, really since then, the '08 insanity. So it's, it's, it's quite a spectacle. And I think, you know, no matter how much people want to learn the lesson of leverage over and over and over again, we all seem to repeat it. And You know, it is what it is. But I think that the Jane— the Jane Citadel Millennium kind of like entire hedge fund complex sort of becoming this like shadow bank is quite interesting, you know, in that like these guys are, are sort of there to— normally the banks would sort of take this on the chin. But now that there's other folks who are like, you know, Jane was an LP, for example, and reportedly was not interested in bidding, which is fascinating, may have taken the Anthropic, however. Really unclear. We're going to learn more, obviously, as some days go on here. But it's, uh, it's an unprecedented time. And, you know, really an insane story that, uh, may just get more insane as we learn more.
Is there a world where the fund continues? Because I'm just hearing the numbers and it's like, you know, for up at $45 billion, the actual money into the fund was maybe $5 billion or something. If you sell the positions, there's a world where wind up with like $10 billion in a bank account, and the LPs are like, well, we gave you $5 billion. Keep going. Get back in the game.
I hope that's the case for the LPs who are awesome, for the fund manager who obviously got quite a lot of whiplash. But at the end of the day, there's this concept on the Street, as you guys know, like, once there's blood in the water, these positions would go to zero. Like, we'll send Micron to $5 just to liquidate this guy at $3. Right? The craziest thing is that's the nature of Wall Street. When this happens, and there's a guy that has to sell $100 billion, you'll have a trillion dollars in front of them just like, let's see this guy cry uncle. It's the saddest, most Machiavellian thing, but he had to blow up. There's no other ending, sadly. Because of the leverage level, it's just like one slight— I remember my old My old boss was a Tiger portfolio manager, reminded me of the 2000 era where there's this very slight change in tone from one optical component supplier. That's like him and his partner from Soros just decided to go as short as they could. It's because they knew ultimately, these vulnerable hands were sitting there after the easy part of the bubble was over, you had this like, okay, what's next? Things have to get a lot crazier. You saw Dwarkesh's tweet. Things like that would have to happen for there to be enough second derivative for somebody to be surprised. Everyone knows AI is in this boom. Everyone knows chips are in this boom. What could possibly shock you to the upside? Not much. So if you hear any little like, eh, we're not going to spend as much, the whole shit hits the fan, and it's just too heavy. So I actually wonder if we're not in for a longer, more protracted decline. Things feel great today. You know, you have this huge boom, this relief rally. A lot of the froth is out of the system. But, you know, what next? You know, I don't know that, you know, a patient and calm market is going to emerge because you had these hyperscalers and the big companies, they FOMO too. They FOMO just as hard as Leopold did, right? If not harder. So this isn't just him. It's the whole world collectively saying, fuck, I got to— I got to go all in on AI. And it's, it's, and who, who had the guts, you know, other than one man, Tim Cook, in the back saying, not me.
Do nothing, win.
Yeah.
Yeah.
No, really, it was Tim Cook. Yeah.
Yeah. The, the, the funny thing, you know, we, we had been joking, uh, we were joking in like Q4 when, you know, they're prior to like coding agents really starting to rip, you know, OpenAI revenue growth had like slowed a little bit and like there was some jitters and. And a lot of this stuff wasn't, you know, public at the time, but you, you could tell some of the kind of crossover types were like getting a little nervous, right?
They kind of expected MAU, DAU numbers.
Yeah.
Yeah. You know?
Yeah.
And really plateaued.
And, and, and then we, and then there was a correction, like there was like briefly, you know, for a period it was probably like 8 weeks. It was like, okay, like, uh, and then it started ripping again and we were taking like a sort of a, um, bit of a joking, like, victory lap being like, cool, like, AI corrected, you know, bubble popped, bubble popped.
We're able to build back sustainably. We're good from here on out. It's smooth sailing. No, I completely agree.
I think the most unexpected thing would be if we saw brand new all-time highs for the entire thing. I think almost everyone on Wall Street is skeptical this will happen, which means it has a chance. Yeah. Yeah. So you're saying there's a chance?
I love it. Can you, can you give me a little bit more insider baseball on what it takes to unwind a big position as a shareholder? Because a lot of people who are not inside the hedge fund world are sort of maybe confused around, okay, yeah, you own $50 million of a $1 billion chip stock. Can't you just dump that on retail? Can't you just like sell markets, sell that on E-Trade or Robinhood? And in fact, it's much more complicated when you're at this level, even though it's public markets. There's not just a big button. Can you walk us through what it actually takes to like sell a big position when you're at that level?
Yeah, there's, there's a lot that goes into it, interestingly. So the first is you have this advertisement system. So if you sell into the into the market, you can try that. And that's called selling into the screens. The screens are the numbers on your screen. Anybody could buy and sell, Robinhood, whatever. So you don't normally do that if you can help it. Selling on screens is at least somewhat quiet. You can just sort of trickle out. There's always this conspiracy that as I'm selling on the screens, there's some guy who can see my screen. And he's like, this guy's got a VWAP market order to sell 10 million shares. That's like, I'm going to tell somebody. And that knowledge would be very, very powerful. And There's even some even crazier conspiracies out there that quants could actually use different— all kinds of insane ideas around what they can do to sniff out that this is happening. There's people that are scared of that. Then you can pick up the phone, and this is the way you'd normally do it, and you call Goldman, and you say, listen, I need to sell 5 million shares of Microsoft or something like that. They say, hmm, should we take it, or do we find a guy that wants to take it, and they'll sort of try to decide. Now, Microsoft is easy. If you're trying to sell Sharean AI, a neo cloud in Australia that nobody wants, that's a tough one. And you own like 10 days of volume. So if you try to hit the screens, you have 10 days of volume. You'd have to be the entire volume for 10 days before you'd be out. You'd probably take the stock down 50% or more, and you don't want to do that. So you try to, you know, do this advertisement process, um, And you basically can post in the stock market that you're a seller of a stock. And you can post that— your 4-digit, what's called market maker ID. And so Goldman's is GSCO. So GSCO would be a seller of, say, Neebius, which was one of his positions. And so you'd call up. You'd say, OK, Goldman. I'm a client, too, of Goldman. What do you got on Neebius? And the guy would say, listen, we got a pretty big seller here. And say, how big? Half a million shares? And he's like, a lot bigger. And so you'd say, hmm, OK. Because they have to advertise that they're working your order. So they have to sort of tell people that there's a seller. They kind of are trying to be coy about how big, but they're not going to waste somebody's time either. So the guy who's heard that there's a big seller, well, he might turn around— he's not supposed to do this— he sort of might turn around and say, there's a huge seller of Neebius out there, and I'm just a little baby fish, maybe I could short 50,000 shares and get in front of this guy. If you're an actual interested buyer, you might also still be nervous, because you'd say, well, if he's really got a ton of size, I might have to be judicious about how I step in. And so if you combine that with the pressure in the market, and you add it all up, and then Usually what you do is you'd have to say, oh, I know a guy that works there and let's see if he's returning calls. And, you know, when you hit up the guy and he's not on Bloomberg, he's hard to reach, it's kind of like, well, it sounds like it could be them selling. So it's not too many people that own that many shares of that security. So you look at the holders list and you're sort of like, who could it be selling 10 million shares? So you call Fidelity and they say, no, we're not selling. You call the next guy. No, we're not selling. Next guy's an ETF. Next guy's an index fund. It's got to be him. And so if it's them, and then you start noticing all of their positions are down, it gets really hard. So ultimately, the bank decides— because you might say, I don't want to sell. The bank says, I don't care what you want. We're selling regardless. And Goldman Sachs is not in the business of holding AI stocks. We're going to sell at any price we can, because our board would rather know for sure that we're down $1 billion and just rip the Band-Aid off than to wonder if we could lose 50%. And so it's Goldman's position that we're just going to just cut the arm off right now before it metastasizes. And so they'll do a fire sale. And of course, Goldman's smart. They're going to reach out to a guy like Citadel or somebody else to place it carefully. But selling the whole portfolio in one shot was a very smart move. Now, again, we've heard the discount could have been as big as 20% to 50%, which is mouthwatering discount to buy some quality companies at. But to end it and have finality, what was really— to answer the question finally— what you really needed to do is the buyer of these stocks has to have the liquidity to hold them for 5 years and do nothing. Because the market— guys like me, and to a very small extent, and guys much bigger— will sit there and say, I don't think you can hold this. And they'll start shorting it, and shorting it, and shorting it, and trying to make you cry uncle. Kyosha in Japan, one of Leopold's holdings, also one of mine, is trading at 3 times earnings. They basically forced— you're forcing the guy to really sell. And if you're going to hold this stock, you have to make sure that you can hold it until it's 2 times earnings or 1 times earnings. And the only player big enough and powerful enough to hold $100 billion and not blink is somebody like Citadel. And even still, some people— there are rumors out there that the people who are going to try to crash your citadel, which I wouldn't advise, but something like that where maybe they'll now have to suffer the same contagion. So it's a very crazy time in the markets. And I don't think we've seen everything yet, because I do think there are some large tech funds that have had the same trade on. I do think liquidation is over, thankfully. But I do think that there are some funds that are about to be found out to be down 30% or down 40% or something like that.
Take me through the mind of Ken Griffin like a couple of weeks ago, there's this rumor that he was sort of like pushing or signaling that there might be a rate hike. But what I'm interested in is if you suspect that there's going to be a fire sale on X, Y, and Z companies, is there a world where you build the hedges before you acquire those assets, or is that too 4D chess? Because that if they, if they wind up acquiring these for 50%, 20% off,, but they already have offsets, then they sort of come in market neutral. Is that possible?
I don't think so. So I'm familiar with Citadel's performance for this month, which is surprisingly up. So I think they're probably one of the only hedge funds in the world this month. Yeah, it's up. So they're actually very small.
They were actually hedged is what you're saying.
Yes. They have a diverse platform of different businesses. A guy trading weather, a guy trading rates, a guy trading stocks, you know, about 1,000 guys trading stocks. And they have a computer fund called Citadel Securities that is a market maker that trades a good chunk of the volume of every instrument in the world. And ultimately, I think that the prime brokers, the Goldmans and Bank of Americas, they do so much business with Citadel. And they've done this before, where they know who to go to, just the same way the US government went to Warren Buffett when they wanted to shore up Goldman. They know that the right person to call is Ken, and he is really going out of his way to make himself the guy to call. And I think that is a great brand, because you may not need to be that guy more than once every decade. But look, once a decade to make a free $5 billion or $10 billion is a great, great guy to be. And it's sort of like he becomes a dependable, trusted partner to these banks. And if he wants something from the banks, he's helped them. Because without him, they might have had to sell that at a negative number. In fact, some people think— I don't think this is what happened, but some people actually think the equity in Leopold's prime brokerage accounts went negative.
Okay.
Which I think is, you know, something that, again, the Goldmans and Bank of Americas try to stop you before you get there.
Sure.
But, you know, they also don't want to sell, like I said, a share in AI, which is an illiquid, tough-to-sell security.
Sure.
You know, they'll sell out your Micron very fast, or you'll sell it out before then. But if you're left holding this bag of liquid crap that you have 60 days of volume to get out of, it's pretty tough to sit there and tell your prime broker, don't worry. Which is why, again, I think he needed cash. Probably somebody on Monday or Tuesday tapped him on the shoulder and said, your margin's looking a little thin. Can you add a couple billion here or more? And things happen so quickly that there was just no time And yeah, it's— I think Citadel learned about this at the 11th hour, as you're supposed to. The firm didn't leak out that they were hurting. They didn't have, to my knowledge, daily performance. In fact, from what I'm told, situational awareness as a young hedge fund was not so great with communication. Not surprising, especially with monthly and quarterly letters. Could have been more timely on some of those. So it's a small group of a couple of guys. So I don't— yeah, that this was the same.
You rewind, what was it, only a month ago that the— or 13F was late, 13F was like late, and everyone was right, right, like he sold everything, work out— did he work out some kind of deal to get it, you know, keep it confidential? But it, it sounded like you just like didn't get around to it. They had other priorities maybe. Do you think you can mention the Do you think you can rebuild a career as a venture investor? Because in venture, you're just gigalong always. It's one of the few forms of investing where it's just so hard to get out of positions.
That's the thing.
I mean, why become a hedge fund manager? I have a friend who wants to start a hedge fund. I told him, this is the most painful, horrible business in the world. Why do this? Start a newsletter business that makes $100 million a year, even $50 million a year of revenue, you've done better than almost every hedge fund on the planet. You do not want to do this job. The reason people do it, and I did it too, and I would never do it again, is it's the sexiest thing in the world. You think you're— the glory is incredible. Yeah, you're the master of the universe. I had friends wanting to quit really high-profile jobs to be a hedge fund. I was just like, you're out of your mind. You don't know what this job is. It's waking up at 3 AM, checking checking Korean stock prices and waking up back up at 6:00 wondering what's happening in the world, stuff like this. There's absolutely no productive thing you're doing. You're providing capital. Other than that, you're really playing this high-stakes crazy poker game and it's certainly fun and interesting, but when it's painful and raw, I hope he'll do something. He's a brilliant person. Brilliant people like that, look, Peter Thiel, had a hedge fund that didn't quite have this level of liquidation or anything like that, but it had a rough last few years. And Thiel was able to obviously not only continue his venture investing efforts, creating one of the biggest funds of all time, one of the most successful funds of all time, investing personally, doing amazing, also getting back into macro trading with Thiel Macro, which supposedly has done well. So I do think there is this period of a few years that, you know, he can reset and take the learnings, take whatever talent, skill, and certainly genius— that nobody denies that he's a brilliant guy— and rebuild. I don't think it's the end at all. And I hope he's keeping like that even temperament about this because, you know, I think a lot of people respect him quite a lot. 100%, no matter how this turned out, you know, he'll be back and successful. But it is a little bit of a humiliation thing that I think most people on Twitter and other places are sort of saying, well, the market tends to humble you. And this is like an extremely humbling moment from being, you know, just 2 months separated from the biggest hedge fund on planet Earth and most successful to being forced to, to sort of liquidate. That is quite a rapid sort of, you know, reversal.
Also, just imagining what the fund looks like in 2 or 3 years if you just survive, right? There was a clip that was circulating yesterday from his appearance on Dwarkesh where he's like, "Oh, there's obviously like 100x left before AGI," right? So, he was like up 20x or whatever thinking like, "I got so much room to run," but just couldn't stay in the game. I got to say—
Yeah, there's always a risk.
I got to— yeah, I got to say, it felt like a— felt like a huge moment for you and your business just because everyone, the whole finance world was learning about the situation from your post. I'm sure a lot of people were glued to your terminal and it felt like a changing of the guard because, again, you were getting pushback. You were getting some pushback. But then 2 hours later, it was like Financial Times and Bloomberg and Wall Street Journal. They're all kind of clearly they needed a couple hours to like run it down. But you got to it first. And yeah, I was, I was quite impressed.
Thank you.
Yeah.
I mean, I think that, you know, we've talked about this in the past. I mean, there is a changing of the guard. You guys helped change the guard in your space. And I think that, you know, the folks at the Journal, the folks at Bloomberg, the folks at these other companies, they're fantastic. Reporters, but they're not active or former players. And, you know, we will hear— we will always hear things before them, uh, because especially on the street, um, because that's just—
well, the crazy— the craziest thing is you, you actually waited until it was like over effectively to, to share, right? Like you had been hearing about this.
There's a lot that we sit on.
Yeah, yeah, yeah. You know, we've been in that position like hundreds times where it's not appropriate to share anything. And sometimes you're sitting there being like, I'm really surprised that legacy media hasn't picked up on this story. It feels like it's just common knowledge. And there's definitely a time and place to just not say anything and let something work its way through the system.
Yeah. I mean, to give the devil their due, the Information is also quite good at this type of thing. And they are particularly good at scoops on OpenAI, which I still haven't unraveled how, but they're obviously very good reporters. But a reporter at a place like that in trad media, they generally don't care about burning bridges and resources or contacts. So they want that news out yesterday. I do care. And it also is a conflict of interest because I don't want to hurt somebody that's given me good information. Betray their confidence, because I have to keep the confidence of these folks if I want to keep talking to them. But I also, in the case of this situation, as the carnage was unfolding, there's sort of the balancing the need for everyone to know with the need for protecting friendships and relationships. You have to make that judgment call each time. I hope that our customers understand that there will be things that we know before others that we can't disclose because We want to protect folks and protect our friends. Bloomberg, Wall Street Journal, they'll never do that. They're, they're always going to serve their customer who is the reader. We can't necessarily do that. You probably know things about Alitany, like you said, hundreds of times, different fundraisers going on, different things like that. And yet we have to all keep our lips closed because, you know, that will be the last time we hear about a fundraiser. And I think that this was a situation where it sort of merited discussion. It was going to happen momentarily anyway. I, in fact, to your, to your point, the thing that got me to publish was my friend saying everyone is hearing this now. Once that happened, I said, all right, well, you know, it's time to let— I can let the cat out of the bag. It's about to be let out anyway.
So, yeah, I have two more quick questions if you have a minute. One is just about how leverage works at a hedge fund. I think you know, again, from the retail perspective, from the much smaller player, you might know that you can go to a, you know, a brokerage and get a little bit of leverage. But what does the process look like as you're scaling into the tens of billions of leverage? At a certain point, you have to go to all of the banks, certain banks. Who's actually like, what is that process to get leverage at that scale actually look like?
And also, let's let's appreciate for them for a moment that I feel like just a month ago the West Coast broadly was taking this insane victory lap, being like, the West Coast has eaten Wall Street. Like, the best and biggest hedge fund is no longer on the East Coast. Like, we just have everything now, finance and technology. And then, and then just deeply humbled, uh, within the span of, of 30 days. Uh, and it turns out Turns out you guys over there, you know a thing or two. And here we are asking you, so how would one go about getting—
So one of the things that I think is not well understood is the prime broker make a spread on— I think this is somewhat understood— is they make their business to make a spread on financing. So if you go to a prime broker and say, I'm never going to use leverage, never. They say, I'm never going to use leverage, and I'm never going to really trade a lot with your firm. You're just going to sit there and say, we'll still take the assets, because we can rehypothecate them and lend them to the guys that are going to take leverage. But in general, that's not a great customer. So if they're making a 1% spread, which actually is a relatively huge amount, and you're borrowing 4x, you're actually giving them 400 basis points of free money. Which is fantastic. In fact, their borrowing costs are probably less than so far. So they may be getting as much as 600 or 800 bps of free money on huge amounts of capital. So leverage is the best friend of prime broker. Now, the risk guy is sitting there saying, well, wait a second. I love lending, but I don't like lending to concentrated portfolios. I don't like lending to short sellers. Short sellers can get big, big, big leaps in their portfolios, like GameStop, for example. So the most that a long can lose is 100%. But if a 4x lever, the most long can lose is 25%. So there's sort of this mix of things you have to think about. I think getting into the privates is usually, for me, a really bad sign for almost every fund, because it's— as tantalizing as private companies are, there is a whole group of people on the West Coast who are much better at that than the guys on the East Coast. And of course, there are funds now like Altimeter and Coatue and others that, that are doing both and doing both.
Yeah. And what made that— what made it so tempting, obviously, for Leopold, that just how close he is to— like, he couldn't be closer to Anthropic. And it's a company that over the last 6 months has had 100x the demand relative to the allocation. Right. So it just felt like You know, and I don't know who knows what the, what the structure on those investments look like, but it's like if you're going to break your rule and do privates, like then that's the company to do it with. But then you still get into a situation where you're like, wow, I really wish this was more liquid.
Yeah, I can't press the sell button.
Give us an update before you leave on, on Korea broadly, because, you know, a lot of people are commenting on, on, on just how similar Leopold's approach is to Korean retail. I don't know how true that is, but I can imagine, like, it's, uh, there's blood in the water over there and the whole country is probably in shambles.
Yeah, I think so. I made a quality criterion calculator and like a little portfolio simulator tool that, you know, basically And Paul Trader Jones said this a while back, and I had a problem with this. Every single trader out there makes one— seems to make the same mistake over and over again, which is their position size is probably 2 to 10x more than it should be. And if you actually— so it sounds nuts, right?
Yeah.
But if you actually run the simulator, and we— ours is kelly. So Kelly was a guy at Bell Labs. He was a member of the technical staff. He was original OG MLTS. And so Kelly came up with the proof called famously the Kelly criterion, which gamblers use— mostly was a gambler thing before a finance thing. And it proves the optimal bet size. And the optimal bet size is your edge subtracted by the reciprocal of it. So if you have 55% edge, your optimal bet size is 10%. That's still quite volatile for folks. And so people do half Kelly or quarter Kelly. Most folks actually don't have an edge when they trade. But if they did have an edge, they're trading as if they had a 4x or 5x Kelly edge, which is interestingly— like, you might say, OK, well, that just sounds swashbuckling, and like, the guy takes a lot of risk.
No.
If you run the simulator, you will go to zero each time. And the simulator is a really cool tool that shows you even with a 60-40 edge on every trade you make, you'll go bust if you overbet. And it's an eye-opener. We might say, who has a 60-40 edge in the stock market? Nobody has a 60-40 edge. But you will absolutely go bust if you don't size correctly. And it's something that I've had to learn very painfully, very, you know, over the years, that I'm almost always overbetting. And I think every fund is sort of the same. And certainly, every retailer is the same. And it's just sort of a weird variance math game that very few people actually map out and say, can I simulate portfolio and just to see what is the sort of the right thing to do in most cases? In fact, after I left the Tiger Cup I worked at, I worked briefly in the office of a guy who worked at SAC Capital, now called Point72, for years. He was one of the best managers. He's a quiet guy nobody's ever heard of, retired, but I got to watch him before I set up my own hedge fund and did the exact opposite, way overbet on everything. I got to sit with this guy for a few months, and I was astounded. What I found is that he was managing, I don't know, $300 or $400 million of his own, basically. He almost never used the capital. 80%, 90% of the capital was just cash. And he would just make these tiny trades. And the guy had almost never had a down— I think his record was he never had a down quarter in 20-something years of trading. And he had like 20%, 30% returns, which is great. And the guy just did these little nibbles. He never lost money. And it was this incredible thing. And then, of course, the second I get the chance to get some capital, I'm 8x leverage. You know, it's just like, you know, it's the dumbest thing in the world, you know, and you live and you learn.
Psychology. Psychology. Well, thanks so much for coming on the show and breaking down. This is always a great time.
Yeah. Looking forward to— Yeah.
See where we go from here. Have a great week. Have a great weekend. We'll talk to you soon.
Cheers, Martin. Bye.
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