Overall, it has spent $3.97 billion on building a crypto war chest of 130,000 BTC, but at the time of writing, it's worth $2.45 billion.
MicroStrategy has snapped up another 301 BTC for $6 million, new filings to the U.S. Securities and Exchange Commission reveal.
The purchases were made between Aug. 2 and Sept. 19, for an average price of $19,851 per coin.
This means that the Bitcoin investment is already underwater by $300,000. At the time of writing, CoinMarketCap data shows BTC is trading at $18,864.
MicroStrategy is continuing to bet big on Bitcoin — even after Michael Saylor took a step back as CEO to become executive chairman.
The business intelligence firm now owns 130,000 BTC — with each coin costing an average of $30,639.
Overall, it has spent $3.97 billion on building this crypto war chest, but at the time of writing, it's worth $2.45 billion.
Back in November, when Bitcoin hit an all-time high of $68,700, MicroStrategy was sitting on a profit of $4 billion.
Saylor was asked this reversal of fortunes bothered him during CoinMarketCap's The Capital conference, but he said:
"If you'd asked the same question to Jeff Bezos in 2003 and said, you know, like you just had an 80% loss in Amazon, do you ever wish you sold Amazon in the year 2001? You know, Jeff Bezos could have sold Amazon in the year 2000 and avoided a 95% loss."
He described such a mentality as "foolish" — and said, if Jeff Bezos or Mark Zuckerberg had offloaded their stock and tried to time the market over the years, they would not be billionaires.
"If you look at all the richest people in the world, they're not traders. I mean, Bill Gates, Jeff Bezos, Elon Musk, Mark Zuckerberg, Larry Page… name the person who traded their way to that situation. You can't really do it. Trying to time the market is ridiculous."
Many of MicroStrategy's acquisitions have been fueled by debt, with the company issuing bonds and selling stock to fund its spending spree.
Earlier this month, the company revealed that it was planning to sell up to $500 million in Class A shares, and part of the proceeds could be used to snap up more crypto.
MicroStrategy's stock price closed down 4.6% on Tuesday.