American businessman and social media personality Dave Portnoy is well-known for his honest takes on the crypto market and he doesn’t hesitate to share his views even when he is sitting on a multimillion-dollar loss.
The Barstool Sports founder posted a confessional video on X on June 4 in which he admitted that as far as crypto is concerned, nobody has ever had as bad timing as him.
Related: Jim Cramer has blunt response to Bitcoin ‘murder’
Calling the past week a “freaking disaster” for crypto, Portnoy said he was panicking like everyone else. He revealed that he holds Bitcoin (BTC) and XRP, which were trading at roughly $63,000 and $1.17, respectively, when he recorded the video. The decline, he said, has left him down millions of dollars.
Portnoy also said he bought the shares of Strategy (Nasdaq: MSTR) a week ago while it was already crashing.
Strategy, the world’s largest Bitcoin treasury company, announced on Monday, June 1, that it had sold 32 BTC the previous week, marking its first Bitcoin sale in years.
As Strategy’s first Bitcoin sale since 2022, the announcement sparked a sharp market reaction. The move surprised some investors because co-founder Michael Saylor has long been a vocal advocate of holding Bitcoin, despite hinting the possibility of a sale last month.
Bitcoin has declined from approximately $73,800 to below $63,900 since Strategy announced selling BTC.
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Portnoy refuses to sell despite getting ‘whacked’ in crypto
Portnoy compared his relationship with crypto to oil and water, saying the two simply don’t mix.
“I have not made a cent in crypto, I have gotten whacked in crypto.”
Despite the losses, Portnoy said he has no plans to sell his holdings and intends to keep holding. During the video, he also recalled a conversation with X (previously called Twitter) co-founder Jack Dorsey, who he said remains convinced that Bitcoin will eventually reach $1 million.
Portnoy argued it’s time to buy when there is “blood on the streets.” He admitted to not holding more “free cash” to buy more crypto assets but said for those with deeper pockets, the cryptocurrency is “on sale.”
Bitcoin was trading at $63,893 at press time, as per Decibel. Whereas XRP was trading at $1.17 at press time.
MSTR/USD, Yahoo Finance
The MSTR stock was trading at $130.15 at press time, around 20% lower than the weekend closing price of $159.09 on May 29.
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This story was originally published by TheStreet on Jun 4, 2026, where it first appeared in the MARKETS section. Add TheStreet as a Preferred Source by clicking here.