MicroStrategy, the enterprise software maker that’s bet big on bitcoin over the past two years, is now underwater on its holdings of the world’s largest cryptocurrency due to the market tumble.

Bitcoin traded around $28,000 apiece on Thursday morning, recovering somewhat from earlier losses that brought the digital token below $27,000. Just last week, it touched a recent high around $40,000. Its all-time high, just below $69,000, was reached in November.

MicroStrategy’s cost basis was roughly $30,700 per bitcoin, as of March 31, according to its first-quarter earnings report. As of the same date, the company owned roughly 129,218 bitcoins, spending a total of $3.967 billion to acquire them.

MicroStrategy’s stock, while volatile, enjoyed success alongside bitcoin in late 2020 and into last year. Now, it reflects the tumult facing bitcoin and the crypto market more generally, which has been rocked in recent days as investors flee risky assets, and as an experimental stablecoin project is under duress.

At their lows, MicroStrategy shares were down more than 13% Thursday to about $145, after plummeting 25.4% Wednesday. The stock pared some those losses later Thursday to trade down about 2%.

Based on Wednesday’s close, MicroStrategy shares are down about 87% from their bitcoin-era highs of $1,315 on Feb. 9, 2021. That came just one day after Tesla announced it bought $1.5 billion worth of bitcoin, a move that may have been inspired by MicroStrategy’s buying and the evangelizing of its chairman and CEO, Michael Saylor.

Since MicroStrategy disclosed its maiden bitcoin purchase, in August 2020, Saylor has become one of the most well-known bitcoin boosters in Corporate America, amassing a large following on Twitter and speaking at various crypto conferences.

He’s made a number of bold predictions and claims about bitcoin, suggesting to CNBC last year it could have a total market cap of $100 trillion eventually and become ”a stabilizing influence in the entire financial system of the 21st century.” As of Thursday, bitcoin’s market value was below $600 billion.

MicroStrategy, which generated $510.8 million in revenue in 2021, has made increasingly risky bets on bitcoin. Its initial tranche nearly two years ago was bought using cash on hand, spending about $250 million, including fees and expenses, at a time when bitcoin traded below $12,000 per token.

MicroStrategy then began to tap the debt market to fund additional purchases, issuing $650 million of convertible notes in December 2020 and $500 million of bonds in June 2021. Proceeds from both were used to buy still more bitcoin.

Most recently, on March 29, a subsidiary of MicroStrategy closed a $205 million loan — collateralized by bitcoin — with the purpose of acquiring even more bitcoin. On April 5, Saylor announced MicroStrategy bought 4,167 bitcoins at an average price of $45,714 each.

The March 29 loan, issued by Silvergate Bank, is now the subject of attention as bitcoin slides. On MicroStrategy’s earnings call last week, CFO Phong Le said if bitcoin fell below $21,000 per token, the company could face a margin call, based on the terms of the loan-to-value (LTV) ratio from Silvergate.

“We took out the loan at 25% LTV. The margin call occurs at 50% LTV. So essentially, bitcoin needs to cut in half, or around $21,000, before we’d have a margin call,” Le explained on the May 3 earnings call. “That said, before it gets to 50%, we could contribute more bitcoin to the collateral package so it never gets there, so we don’t ever get into a situation of a margin call.”