Bitcoin News: Is Strategy Under Too Much Debt? $2B Bond Sale Raises Questions

Strategy is making headlines again with its aggressive Bitcoin strategy. The company is raising $2 billion through a private sale of convertible bonds, set to mature in 2030. These bonds won’t pay regular interest, but investors can choose to convert them into cash or Strategy’s Class A shares. The goal? To secure $1.9 billion – mostly to buy even more Bitcoin.

It’s an aggressive strategy, but so far, it’s working. Strategy’s stock has surged 372% over the past year, making it one of the best-performing stocks in the U.S. market.

Some investors are raising concerns, and one of them isn’t holding back.

Jason Calacanis Questions the Strategy

Angel investor Jason Calacanis is skeptical. He believes Strategy should be valued lower than its Bitcoin holdings because of its growing debt. He also raises concerns about asset security, pointing out that shareholders don’t actually control the company’s Bitcoin.

Another issue, he argues, is whether CEO Michael Saylor Michael Saylor   Michael Saylor is a US-based entrepreneur and Bitcoin Advocate. He is the founding member of MicroStrategy (now Strategy), a development company that focuses on cloud-based services. He urges investors to invest in Bitcoin and shares new updates on Bitcoin on his X account.   His firm, Strategy, now makes Bitcoin its primary reserve and stockpiles Bitcoin frequently. He has attended several events like the Bitcoin Conference 2025 to advocate for Bitcoin and its future growth.   Quick Facts   Full Name Michael J. Saylor Birth 04-02-1965 in Lincoln, Nebraska Nationality American Education BS from MIT Known for Bitcoin Advocacy   Michael Saylor – Career Timeline 1996: Named "Washington High-Tech Entrepreneur of the Year"   1998: MicroStrategy went public through an IPO   2021: Became a top Bitcoin advocate and urged its adoption.   msaylor@microstrategy.com EntrepreneurCrypto and Blockchain ExpertAuthor is overpaying for Bitcoin. According to Calacanis, every time Strategy buys more, it means someone else thinks their money is better used elsewhere.

Could Strategy’s Stock Still Surge?

Even with his doubts, Calacanis isn’t betting against Strategy. He admits the stock could keep rising in the short term. So far, the numbers support that view—Strategy’s stock climbed 1.6% on Thursday and has jumped 352% in the past year, far outpacing the S&P 500’s 23.5% gain.

Despite falling 30% from its November peak, the stock is still up over 700% in three years, showing strong investor confidence.

The Bigger Picture: A $21 Billion Goal

The $2 billion bond sale is just part of a much larger plan. Strategy ultimately aims to raise $21 billion over the next three years through stocks, bonds, and preferred shares. However, the success of this plan depends on market conditions. If things don’t go as expected, the company may need to adjust its approach.

To address investor concerns, Strategy recently held a webinar explaining its strategy, but key questions remain. Can the company keep buying Bitcoin at this pace without liquidity issues? Will its rising debt become a long-term problem?

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The numbers don’t lie, but neither does risk. Strategy’s bet is big, but so are the consequences.

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