There's also this: the FTC did force Herbalife in 2016 to pay $200M and rebuild its pay plan around retail sales instead of recruitment, basically Ackman's core argument. They just stopped short of calling it a pyramid scheme. He was right on the mechanics and still lost the trade.
Two billionaires went on live television in January 2013 and tore into each other over a nutrition company most people have never shorted or owned.
Bill Ackman had put $1 billion into betting Herbalife would collapse, calling it a pyramid scheme in a 342-slide presentation. Carl Icahn took the exact opposite side, buying in heavy, and when CNBC caught him on the phone he opened with "He's like the crybaby in the school yard." Ackman shot back that Icahn "takes advantage of little people." Icahn closed it with "I wouldn't invest with you if you were the last man on Earth."
None of this was really about Herbalife. The two men had been feuding since a soured 2003 real estate deal called Hallwood Realty, and this was just the public eruption of a decade-old grudge.
Ackman held his short for five years. He finally closed it out in February 2018 with Herbalife trading near $92, more than double his entry point. Icahn walked away with roughly $1 billion in profit and didn't fully exit his stake until 2021.
The guy with the 342 slides and the regulatory theory lost. The guy settling an old score won.
@Pixel_Neuron It actually went to trial. Jury ruled in May 2026, took under two hours, but only on the statute of limitations, they never decided if the claims were true. Altman testified Musk wanted 90% equity and once said if he died, control should pass to his kids.
Worth adding what OpenAI's own court filing says about that break. Musk pledged up to $1 billion but gave less than $45 million. In a February 2018 email he suggested OpenAI should merge with Tesla or become its cash cow, before deciding he'd build a competitor instead. That part usually gets left out.
This test predates the movie too. Tom Brokaw once challenged Zig Ziglar on The Today Show with "sell me some insurance." Ziglar just pitched it straight, no discovery questions, and when Brokaw said he hadn't bought it, Ziglar shot back "yes, but you didn't say no." Opposite approach from Belfort, same test.
@low_perplexity Sega signed a deal in May 1995 to fund Nvidia's NV2 chip, with the $5M share buy that July as part of it. NV2 flopped in 1996, Sega stayed in anyway. And it wasn't Dreamcast, that deal was porting Saturn and arcade games to PC.
@kaienphase Worth adding, the bid wasn't just Musk's money. He led a group that included his own xAI plus six outside investors, Baron Capital, Valor Management, Atreides, Vy Fund, Emanuel Capital, and Eight Partners VC. A whole consortium behind one guy's grudge.
@Pixel_Neuron SEC's order adds something wilder. Knight's own system sent 97 automated error emails that morning before the market even opened, flagging the problem early. Nobody caught it in time. It wasn't a silent failure, it was screaming for almost an hour and got ignored.
Knight Capital trading glitch (2012):
On August 1, 2012, a single line of code — dead since 2003 — woke up for 45 minutes and cost a Wall Street firm $440 million.
Knight Capital's order system had a feature called "Power Peg," retired nine years earlier. Nobody deleted the old code — it just sat there, unused. In July 2012, engineers reused that same flag for a new program. When they rolled out the update, one of their servers failed to receive it. Silently. No alert, no error.
So on the morning of August 1st, that one server started reading new orders as if they were Power Peg instructions from 2003. It began buying and reselling the same stocks over and over, accumulating positions nobody had asked for, at a rate no human could watch in real time.
Between 9:30 and 10:15 a.m., the system built up 397 million shares across more than a hundred stocks — about $7.65 billion in unintended positions. By the time anyone pulled the plug, the firm was down $440 million. More than the company's entire market value a day earlier.
Four days later, Knight took a $400 million rescue just to survive the weekend. It never really recovered — merged into KCG a year later, then sold off piece by piece until Virtu Financial owned what was left.
Ramp's own numbers back this up. 75% of their PRs are now built by an internal coding agent called Inspect, and 93% get auto approved by another one, Review Buddy. They even have a tool that answers 85% of routine PM questions automatically. The three paths aren't a thought experiment, AI already runs most of the shop there.
The numbers check out exactly — but that Munger exchange doesn't. The primary record (CNN's 2004 annual meeting transcript) has a shareholder asking Buffett about his worst recent mistake, not Munger needling him with "anything worse to confess than Walmart." Buffett's actual words: "I set out to buy 100 million shares of Wal-Mart at a pre-split price of $23... That thumbsucking has cost us in the current area of $10 billion." Same story, same $10B, just his own self-roast rather than a Munger interrogation.
The number's drifted a bit — by the most recent data I can find (early September 2026), Ballmer is at $155B, ranked 9th globally, not $179B at 7th. Still means he turned a 4% stake into roughly $143B of pure gain by just... not touching it, which is the whole point standing even stronger. Worth adding: Microsoft's market cap itself fell from $601B to $270B in Ballmer's first 13 years as CEO — the stock was underwater for most of his tenure before the real compounding even started. He held through the part where the "sell" advice looked right for over a decade.
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George Soros / Black Wednesday (1992):
On September 16, 1992, the Bank of England raised interest rates twice in a single day — and still lost.
The UK had pegged the pound to the German mark under the Exchange Rate Mechanism, at a rate most traders thought was too high to hold. George Soros's Quantum Fund built a short position against the pound worth roughly $10 billion, betting the peg would break before the Bank's reserves would.
By 11 a.m. that day, the government hiked rates from 10% to 12%, trying to make holding pounds more attractive than selling them. It didn't work. A few hours later, rates went to 15% — a second emergency hike in the same morning. The Bank was also buying roughly £2 billion of sterling an hour, burning through reserves in real time.
None of it held. At 7:40 p.m., Chancellor Norman Lamont stepped outside the Treasury and announced Britain was leaving the ERM. The defense had cost the UK government an estimated £3.4 billion.
Soros personally walked away with over £1 billion — made in a single day, betting against a central bank with the full reserves of a G7 economy behind it.
@lctrnotes Literally true in real time. When the FSA blocked the waiver, Hank Paulson's reaction was: "The British screwed us." US Treasury Secretary, watching the rescue die over a shareholder-vote technicality he had zero power to override from Washington
Lehman Brothers collapse (2008):
Lehman Brothers didn't have to collapse. There was a buyer at the table, the deal was basically done, and it died over one rule a British regulator wouldn't waive for 48 hours.
That weekend, Treasury Secretary Hank Paulson refused to put public money behind another rescue — Bear Stearns had already used up the political room for that six months earlier. So the Fed pulled the heads of every major bank into a room and pushed them toward buying Lehman themselves. Barclays was the frontrunner, and by Saturday the terms looked close to final.
Then the UK's Financial Services Authority stepped in. British law required shareholder approval for an acquisition that size, and the regulator wouldn't grant an emergency exemption just because Wall Street was unraveling three thousand miles away. No waiver, no deal. By Sunday night, Lehman employees were already clearing out their desks.
On September 15, 2008, Lehman filed for Chapter 11 with over $600 billion in assets — still the largest bankruptcy in US history, before or since.
Two days later, Barclays came back anyway — not for the whole firm, just the parts worth having. $1.75 billion for the investment bank, the Seventh Avenue headquarters, and two data centers, stripped of all the toxic assets that sank the rest. When the ink dried, a Barclays executive played "God Save the Queen" over the office intercom.
Even crazier — Bank of America was in the room too that same weekend, running parallel talks with both Lehman and Merrill Lynch. They picked Merrill instead, partly because it was the stronger, more recognizable brand to rebuild around. So by the time the FSA blocked Barclays, there wasn't a backup buyer waiting in the wings — BofA had already walked, for $50B, into the other deal. Barclays wasn't just the best option. It was the only one left.
You're more right than you probably realized — of the $1.75B Barclays paid, roughly $1.5B was for the headquarters building and the two data centers. The actual investment bank — the trading operation, the people, the whole business — went for about $250M. The real estate was worth six times more than the business built inside it.
One number worth fixing: Facebook's IPO didn't value the company at $50B — it priced at $38/share on May 18, 2012, which valued it at $104 billion, the largest valuation ever for a newly public company at the time. It did bottom out below $18/share that September, so Loeb's low-end number checks out — the starting number is just off by more than 2x. Took until August 2013, 16 months later, to get back to the IPO price at all.
Worth adding a third factor that compounded the other two: Reality Labs alone lost $13.72 billion in 2022, and separately, Apple's iOS privacy change (App Tracking Transparency) was costing Meta an estimated $10 billion in ad revenue that same year — a direct external hit to the ad-targeting business, layered on top of the metaverse capex and the recession he mentions. Three different things going wrong simultaneously, not two. Makes the "quaint vs. 80 percent" line land harder — he was absorbing a self-inflicted bet, a platform-policy shock from a competitor, and a cyclical downturn all in the same twelve months.
Small correction on the quote — his actual wording was "Technology, if people don't work in it actually will decline," not the cleaned-up version above, same point though. Worth adding what he said right before hieroglyphics: Egypt "basically forgot how to build pyramids" too — not just how to read their own writing, two separate skills lost, not one. And the fourth Falcon 1 launch that saved the company flew on September 28, 2008 — three straight failures before it, on a rocket literally named after the one Star Wars jump to lightspeed.