The Forbes Cover Curse Strikes Again: Michael Saylor’s MicroStrategy Takes a Dive
Staff Writer • 2025-02-26
The Rise of Michael Saylor and His Bitcoin Empire In the high-stakes world of finance, landing on the cover of Forbes is supposed to be a crowning achievement. It signals that you’ve made it, that you’ve reached the upper echelon of business and innovation. But if history has shown us anything, it’s that a Forbes cover story can also be the beginning of the end. Michael Saylor, the executive chairman of MicroStrategy, is the latest high-profile figure to experience what some are calling the “Forbes Cover Curse.” For years, Saylor has been one of Bitcoin’s loudest evangelists, transforming MicroStrategy from a business analytics company into a corporate Bitcoin whale. His strategy was bold—leveraging company funds and taking on billions in debt to accumulate a massive Bitcoin treasury. It was a move that paid off handsomely as Bitcoin soared in value, turning MicroStrategy’s stock into a high-volatility crypto proxy and making Saylor a billionaire many times over. In January 2025, he appeared on the cover of Forbes, hailed as “The Bitcoin Alchemist.” The article painted him as a visionary, a financial pioneer who had cracked the code of modern corporate finance by treating Bitcoin as a corporate treasury asset. The Market Turns: Bitcoin Falls, MicroStrategy Takes a Hit And then, almost on cue, the market had other plans. Within days of Saylor’s Forbes cover debut, Bitcoin took a sharp dive, dropping below $90,000. The ripple effect was immediate—MicroStrategy’s stock plummeted by nearly 11% in a single day, with a three-day loss totaling around 22%. It was an abrupt reminder that in crypto, fortunes can turn overnight. While the stock had been riding high on Bitcoin’s rally, any sign of weakness in the market meant MicroStrategy was destined to feel the pain tenfold. The Curse of the Forbes Cover: A Troubling Pattern This kind of spectacular reversal has played out before, and Saylor’s Forbes moment only adds to the eerie pattern. The Forbes Cover Curse has long been whispered about in financial circles. The theory goes that when someone graces the cover of Forbes, they’ve often hit the peak of their success—meaning there’s only one direction left to go. There’s no shortage of examples. Elizabeth Holmes was once celebrated as the youngest self-made female billionaire when Theranos was on top of the world. Then the fraud unraveled, and she went from the cover of Forbes to a prison cell. Sam Bankman-Fried, the supposed crypto genius behind FTX, was anointed as “The Next Warren Buffett” on the cover of Forbes, only for his empire to implode in one of the biggest financial scandals in history. Adam Neumann of WeWork was painted as a revolutionary who would change the way people worked, right before the company’s catastrophic failed IPO and his eventual ouster. Even outside the tech world, figures like Richard Branson, Martha Stewart, and Bill Gross all had their time on Forbes’ front page—right before hitting major setbacks. Saylor’s History of Boom and Bust For Saylor, this isn’t his first ride on the boom-and-bust rollercoaster. Back in 2000, during the dot-com bubble, MicroStrategy’s stock price soared to $313 per share, making Saylor one of the richest men on the planet. Then, the company was forced to restate its earnings following an SEC probe, and MicroStrategy’s stock crashed to $72 almost overnight, eventually falling below $1 over the next two years. Saylor’s $13 billion net worth evaporated, and he was left with a battered reputation and a company on the brink. It took two decades and a Bitcoin bet of unprecedented scale to bring him back into the spotlight. Can MicroStrategy Survive Another Crash? The big question now is whether history is about to repeat itself. MicroStrategy’s entire corporate strategy is tethered to Bitcoin, and while it has benefited from the crypto boom, the risks are just as extreme. The company is highly leveraged, having borrowed billions to buy Bitcoin at an average price of around $35,000 per BTC. Right now, that bet is still in the green, but Bitcoin’s notorious volatility means that a steep downturn could quickly lead to margin calls and liquidity problems. Saylor, of course, remains unfazed. He’s never wavered in his Bitcoin maximalism, insisting that holding Bitcoin for the long term will prove to be MicroStrategy’s greatest strength, not its Achilles’ heel. He believes the company is positioned to thrive in a world where Bitcoin eventually replaces fiat currencies. Is the Curse Real or Just Coincidence? There’s no escaping the bad timing of his Forbes cover debut and the market’s immediate reaction. Whether or not the Forbes Cover Curse is real, the pattern is undeniable: reach the peak, land on the cover, and watch the fall begin. If history has anything to say about it, the next few months for Michael Saylor and MicroStrategy will be a wild ride.
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