When Will Strategy Buy the Bitcoin Dip?

Michael Saylor’s Bitcoin-buying behemoth has yet to buy the latest dip, possibly signaling Strategy’s approach to acquiring the asset is shifting alongside market headwinds.

Tysons, Virginia-based Strategy, which pivoted from a software focus to become a Bitcoin Treasury, said that it bought Bitcoin 18 times last year, according to Saylor Tracker. Nearly half those announcements followed U.S. President Donald Trump’s reelection in November, as crypto prices boomed.

So far, Strategy has disclosed six Bitcoin purchases this year. However, its holdings have remained unchanged at 499,096 Bitcoin since Feb. 24. At the time, the company said that it had purchased Bitcoin for an average price of $97,500 per Bitcoin.

The pause comes amid Trump’s on-again, off-again tariffs, which have battered stocks and crypto, while prompting outflows from spot Bitcoin ETFs. Leading up to Bitcoin’s latest drift below $80,000 on Thursday, spot Bitcoin ETFs had bled $649 million since Monday, per CoinGlass.

Spot Bitcoin ETFs had a historic U.S. debut last year, and along with Strategy’s insatiable demand for Bitcoin, the two market forces helped buoy Bitcoin’s price to new heights. 

Prediction market traders on MYRIAD doubt that Strategy will confirm a new Bitcoin purchase on Monday, penciling in a 60% chance that the firm’s holdings remain unchanged for a third consecutive week. (Disclosure: MYRIAD is owned by Decrypt‘s parent company, DASTAN.)

Strategy’s stock price has fallen 18% over the past month to $265, according to Yahoo Finance. Despite the recent drop, its shares are still valued 50% up from a year ago.

Strategy’s Strategy

Strategy raises capital to buy Bitcoin by selling shares or bonds. And its ability to raise capital cheaply is influenced by the volatility of its stock price and Bitcoin’s momentum, according to Compass Point Research & Trading analysts Ed Engel and Joe Flynn

“MSTR’s cost of capital increases during market corrections, which makes it harder for Strategy to buy BTC when prices dip,” Engel and Flynn wrote in a research note this month.

Within the past few years, Strategy has embraced so-called convertible senior notes as a way to buy Bitcoin. As a form of company debt, investors can convert these notes for shares.

Strategy said that it had sold $3 billion worth of convertible senior notes at a 55% conversion premium relative to its stock price in November. Investors later paid a 35% conversion premium on $2 billion worth of convertible senior shares in February, indicating its offering had become less lucrative.

At the same time, Strategy unveiled “STRK” in January. As perpetual strike preferred stock, the Nasdaq-listed product pays a fixed dividend indefinitely, unless Strategy decides to redeem it.

Strategy raised $563 million through the STRK offering in January, and on Monday, the company said it would offer another $21 billion in STRK “over an extended period.”

Mark Palmer, a senior equity research analyst at Benchmark, told Decrypt that Strategy’s recent pause likely stems from a focus on arranging the new offering.

“There is no reason to believe that Strategy’s appetite for buying bitcoin has abated,” he said, describing Monday’s announcement as “an emphatic statement about its commitment to its bitcoin acquisition strategy.”

As market participants waited to see whether that offering would translate into immediate buys, Saylor, Strategy’s ever bullish co-founder and executive referenced the product on Thursday.

In a post on X (formerly known as Twitter), he said, “$STRK while the iron is hot.”

Strategy did not immediately respond to a request for comment from Decrypt.

Edited by James Rubin