Link copied
By David Pan
(Bloomberg) -- Michael Saylor’s Bitcoin accumulation firm Strategy Inc. has survived yet another crypto market meltdown with some fresh financial engineering.
Most Read from Bloomberg
US Has Opened a Passage Through Hormuz, Central Command Says
Anthropic Unveils AI Agents to Field Financial Services Tasks
The outlook could hardly have looked more dire. Back on Feb. 5, the cryptocurrency had lost half its value and Strategy’s common shares used to fund most of its token purchases had tumbled by an even greater amount. That was all before the firm disclosed a $12.4 billion loss later that afternoon.
Exactly three months later, Strategy reported a $12.5 billion loss for the first quarter to write down the value of its roughly $67 billion horde. But few investors seem to care. Bitcoin has clawed its way up from its recent lows to $80,000 and the shares have jumped. Saylor is once again the talk of the digital-asset market and beyond; however, the underlying risks remain the same.
The recovery is largely thanks to hybrid securities known as perpetual preferred shares that Strategy began selling last year. The dividend-paying shares have been used to finance the current Bitcoin buying spree by Saylor, the co-founder and executive chairman of the one-time enterprise-software maker formerly known as MicroStrategy. Market observers have credited Strategy — which bought more than $4 billion of Bitcoin in April — as underpinning demand for the coin amid the general market uncertainty caused by the military conflict in the Middle East.
The niche securities have been used by banks, utility companies and real estate firms to meet regulatory capital requirements and were typically sold to institutional investors. Strategy has been marketing what they call Stretch preferred to retail buyers over platforms including Robinhood and Charles Schwab, touting the junk-bond-level yielding securities as an alternative to money market funds.
“They have found an audience,” said Michael Youngworth, head of global convertibles and preferred strategy at Bank of America. “It’s people who trust ‘Bank of MicroStrategy’ here. You have to be comfortable with the risk, but if you are, then I understand the appeal for a retail investor. That’s probably why he can keep selling.”
Prior to last year’s almost 50% collapse in Strategy’s common stock, Saylor had been able to leverage the premium between the share price and Bitcoin to raise capital from equity sales without much dilution during crypto bull markets. As that gap nearly evaporated, skeptics such as the well-known short seller Jim Chanos shorted the shares, saying the strategy was unsustainable.
The Bitcoin accumulation strategy is predicated on the notion that the price of the cryptocurrency will continue to go up, luring in even more investors fearful of missing out on the gains. If demand falls, Strategy risks being unable to fund additional purchases, undermining the flywheel aspect of the strategy.
“At the end of the day, the reason we can create that is because we’re not funding that with operating cash flows of an operating business,” Saylor said during an interview at the Bitcoin 2026 convention in Las Vegas last week. “We’re doing it with a capital investment. And the question really is, are you going to collect 11.5% in the capital investment over time?”
While the company remains a hardline holder of the digital currency, it has listed Bitcoin sales as part of its future trading strategy.
“Our ability to sell Bitcoin either to buy US dollars or sell Bitcoin to buy debt if it’s accretive to Bitcoin per share, right, is something that we would consider going forward,” Strategy Chief Executive Officer Phong Le said on the earnings call on Tuesday. “We’re not going to sit back and just say we’ll never sell the Bitcoin. We want to be net aggregators of Bitcoin increasing our total Bitcoin.”
The company sold some of its Bitcoin holdings in 2022, in part to generate tax benefits for its gains from Bitcoin purchases. Shares of the company were down 4.3% post market at 7:55 p.m. in New York.
--With assistance from Isabelle Lee.
(Adds comments on potential Bitcoin sales from 10th paragraph.)
Most Read from Bloomberg Businessweek