Early Uber Investor Slams Saylor’s Strategy: ‘I Would Never Touch It’

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In a recent social media outburst that had all the subtlety of a jackhammer, prominent venture capitalist Jason Calacanis made it crystal clear: he would rather wrestle a bear than touch Michael Saylor’s strategy-even if the stock plummeted like a rock from the sky. 🤦‍♂️

Calacanis didn’t stop there. Oh no, he also insisted that if the company goes belly-up, there should be no Bitcoin bailouts. Because, why not throw in a little more drama to the mix? 🎭

The early Uber investor’s vitriol comes hot on the heels of a Wall Street Journal report that digital asset treasury companies are… well, “crumbling.” Yes, that’s right-just another day in the rollercoaster world of crypto, where the only thing more unpredictable than the market is the next wild opinion. 🚀📉

Earlier, Calacanis had urged investors to steer clear of Saylor’s convoluted approach and simply buy Bitcoin directly. Back then, he was so confident that he was 95% sure he’d be right-because, of course, 5% of doubt is just for amateurs. 😏

But now, his latest rant took a more cautious tone. While he’s stopped short of calling Saylor’s strategy a Ponzi scheme (because, apparently, even he has limits), he did warn, “Whenever you see a company using creative new metrics or innovative capital structures, consider that worthy of deeper investigation. Could be genius, could be a dumpster fire.” 🔥🛢️

And as it stands, there’s only a 3% chance of Strategy being forced to liquidate its holdings-so at least it’s not completely doomed. But, given the way things are going, let’s just say the odds aren’t looking great for Saylor’s little gamble. 🤷‍♂️

Will Strategy Bounce Back? 🧐

Now, the plot thickens. Jim Chanos, the founder of Kynikos Associates, recently announced that his firm had wrapped up its anti-MSTR trade after pocketing some nice, hefty returns. A 45% crash in the stock of Saylor’s Bitcoin-heavy treasury firm will do that for you, apparently. 👀

But wait-there’s more! In late October, Strategy was forced to increase the yield on its preferred shares to attract the kind of demand that, until then, had been as elusive as a unicorn in a haystack. 🦄

Some crypto optimists think Chanos’ move is a sign that cryptocurrency treasury companies could finally see a bullish reversal. But, you know, don’t hold your breath-these companies are under pressure, and the ones with crypto holdings in the red are going to find it hard to sell more shares anytime soon. 🏦

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2025-11-09 21:41