Michael Saylor's Strategy's Bitcoin bets are soaring, with the firm set to double its capital-raising goal for Bitcoin to an impressive $84 billion

Michael Saylor's (Nasdaq:MSTR) capital-raising goal is set to double to an astounding $84 billion as the firm ramps up its Bitcoin bets.

This comes after Sogo announced a record loss for the March quarter, which was largely due to a new accounting rule that requires companies to value their digital assets at current market prices..

Sogo last week disclosed plans to sell an additional $21 billion in common shares, following the completion of a similarly scaled equity initiative in October. When the company announced the fourth-quarter earnings in February, it had already unveiled an intention to pursue a debt purchase program for an estimated $42 billion.

Of this amount, $14.6 billion is planned to be raised through new debt, nearly double the initial goal.

Sogo reported a large shortfall of $4.2 billion in the previous quarter.

As part of a broader strategic assessment and collaboration among corporate buyers of the OG token, they are now recognizing the implication of the underlying price volatility, which will naturally lead to huge changes in earnings.

The dot-com software giant, which has become a leveraged Bitcoin proxy, applied the approved accounting change in the March quarter of 2023. Sogo currently owns 555,450 BTC, or about $53 billion of Bitcoin assets, following its most recent purchase, which was announced on Monday.

Before the recent change in accounting practices, the company used to classify its Bitcoin assets as intangible assets, similar to patents and trademarks.

But as Bitcoin’s price went down, the company had to decrease the value of its coins, and any profits could only be realized at the point of token sale.

Saylor, who co-founded and chairs Strategy's initiatives, has been a major force on Wall Street and in the cryptocurrency sector over the past five years.

His most notable feat is turning his ageing business intelligence software company, Strategy, which was founded in 1989 and went public via an IPO in June 1998, into the largest and inaugural leveraged Bitcoin proxy worldwide.

In the first quarter of 2025, its software segment revenue decreased by 3.6%, reaching $111.1 million, according to its earnings report.

Saylor's persistent lobbying has significantly aided Bitcoin's integration into the mainstream market.

Today, there are more than ten Bitcoin exchange-traded funds in the United States alone, and several companies are emulating Strategy's strategy.

A new world of investing has unfolded around this concept, with fund issuers creating products like leveraged convertible bond funds that distribute capital to companies with Bitcoin on their books.

By deftly engaging risk-taking retail investors and astute hedge funds seeking opportunities, Saylor has sidestepped the skepticism of his Wall Street critics and assembled a substantial Bitcoin empire.

Through this undertaking, he has been instrumental in developing an advanced crypto-investment complex. Strategy's stock has surged nearly 3,000% since Saylor began making his Bitcoin purchases in 2020.

While Saylor has been busy raising large sums of capital through common share and debt offerings to buy more Bitcoin, which has seen Strategy become one of the most active issuers of securities and nearly outperform every major US stock, a pressing concern among many observers is: how sustainable is this approach in the long run?

So far, the bet is in Saylor's favor.

But new players are making things more difficult for investors as they threaten the established players with deep pockets and political clout.

For instance, an affiliate of Cantor Fitzgerald, Tether Holdings – a stablecoin issuer – and SoftBank Group (6503.TO) joined forces a couple of weeks ago to form Twenty One Capital with the aim of amassing Bitcoin.

But that has not perturbed Saylor.

His decision last week to double Bitcoin's capital plan indicated this. Strategy has significantly increased its Bitcoin holdings in the last six months, investing billions of dollars in acquisitions nearly every week since late October.

Recently, the company has been funding its acquisition spree through a complex mix of common stock and debt issuances, convertible offerings, and preferred share sales.

Just this week, the company announced the purchase of 1,895 BTC for around $180.3 million, at an average price of $95,167 per bitcoin. It also reported an impressive BTC Yield of 14.0% YTD 2025. As of 4 May, Strategy holds 555,450 BTC, acquired for approximately $38.08 billion, at an average price of $68,550 per bitcoin.

$MSTR has acquired 1,895 BTC for ~$180.3 million at ~$95,167 per bitcoin and has achieved BTC Yield of 14.0%