Why Dave Portnoy Is Begging Michael Saylor to Buy More Bitcoin

Barstool Sports founder Dave Portnoy called on Michael Saylor, the head of the largest Bitcoin treasury company, MicroStrategy, to increase the scale of the company’s Bitcoin purchases, posting the meme “MORE!” as a reaction to the official announcement that MicroStrategy had acquired 1,550 $BTC more over the past week.

Portnoy’s post coincided with his own admission last week that he lacked free cash to continue supporting his portfolio on his own amid the prolonged market decline.

For Dave Portnoy, who compared the current situation on exchanges to chaos at a racetrack, large institutional deals remain the main factor behind a possible recovery of his positions.

His relationship with crypto, which the businessman himself described as an attempt to mix water with oil, has led to his capital being locked in losing positions, while his net losses, including positions in Bitcoin and $XRP, already amount to millions of dollars.

Dave Portnoy is down millions on $XRP, $BTC, and MSTR

On the spot market, Portnoy’s large Bitcoin position remains under strong pressure as the price fluctuates around $63,000. The situation is worsened by his $XRP purchase, made in late January near the local peak of about $1.70, while the asset is currently trading around $1.17.

Moreover, his attempt to diversify the portfolio by buying MSTR shares a week ago led to that position falling by another 20%, according to the businessman himself. Portnoy thus confirmed that he had fully exhausted his free liquidity during the intermediate stages of the market decline and had lost the ability to defend his assets.

MicroStrategy’s purchase of 1,550 $BTC was made at an average price of $65,332 amid the broader market decline. This move became an important signal for industry participants, as one week earlier the company, which holds more than 800,000 $BTC, broke its “never sell” rule for the first time in three years.

Yes, the earlier sale of 32 $BTC to pay dividends triggered a wave of panic and accelerated the decline in prices, but the new purchase exceeded the size of that sale by almost 50 times. Interestingly, despite the general pessimism, Dave Portnoy also announced at the time that he intended to hold his positions without realizing losses.

The main psychological reference point for Portnoy, according to him, remains the long-standing personal promise of former Twitter CEO Jack Dorsey that Bitcoin will inevitably reach $1 million.