Dave Portnoy is staring at million-dollar losses on his crypto bets, but that isn't stopping him from telling Michael Saylor to keep buying Bitcoin. The Barstool Sports founder took to social media to urge Saylor and MicroStrategy to continue their Bitcoin purchasing spree, a striking message from someone whose own portfolio is bleeding. Portnoy holds XRP and MSTR stock alongside his Bitcoin position, and the paper losses are substantial — though he didn't specify an exact figure.
What Portnoy holds — and what it's costing him
Portnoy's crypto bag includes XRP, a token that's been volatile for years, and shares of MicroStrategy, the company Saylor built into a Bitcoin proxy. With both assets taking a hit in recent weeks, his losses climbed past seven figures. He didn't say whether he's sold anything or is just sitting on the red ink. But the fact that he's still publicly cheering on Saylor suggests he's not running for the exits.
A public plea to double down
Portnoy directly called on Saylor to keep the buying going. He didn't offer a specific price target or timeline, just a clear message: don't stop. MicroStrategy has been the most aggressive corporate Bitcoin buyer on the planet, and Portnoy wants that to continue. Whether Saylor responds or adjusts strategy isn't known — but Portnoy's endorsement carries weight among the retail crowd that follows his every trade.
Between a loss and a long-term bet
The timing isn't great for Portnoy. Watching your portfolio drop by seven figures while telling the biggest whale to buy more takes nerve. It's either conviction or stubbornness — maybe both. Portnoy has always been loud about his crypto plays, and he's not going quiet now. For now, he's betting that Saylor's appetite for Bitcoin outlasts his own pain.
