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 co-founder of Strategy (formerly MicroStrategy). Before founding Microstrategy, he was a rocket scientist and studied aeronautics and astronautics at MIT on an Air Force scholarship. He dubs Bitcoin 'Digital Gold'.   He made some early investments in Bitcoin as soon as he realized it was going to be the next big thing in shaping decentralized finance from traditional finance. His firm's Strategy has made Bitcoin its primary treasury reserve.   Quick Facts Full Name Michael J. Saylor Birth 04-02-1965 in Lincoln, Nebraska Education BSc from MIT Marital Status To be updated / Unmarried Nationality American Net Worth $8.4B (Feb. 20205, Refer for realtime)   As per Forbes, Saylor bought another 17,732 bitcoins for $175 million in October 2020. Forbes covered Michael Saylor on its front page and called him "The Bitcoin Alchemist" as the latter's Net Worth hit a whopping $7.6B in January 2025.   Michael Saylor – Career Timeline 1983–1987: Studied Aeronautics & Astronautics and Science, Technology & Society at Massachusetts Institute of Technology (MIT). 1989: Co-founded Micro Strategy (Strategy). 1998: Micro Strategy IPO – Took Micro Strategy public on the NASDAQ at $12 per share. 2000: Accounting Scandal & Crash – Micro Strategy's stock plunged 62% in a day due to an accounting misstatement, wiping out billions in valuation. 2004–2019: Micro Strategy Rebuilds – Worked towards cloud-based analytics and AI-driven business intelligence, regaining stability. 2020: Bitcoin Strategy & Investment – Led Micro Strategy's $425M Bitcoin investment. He made it the first publicly traded company to adopt Bitcoin. 2021: Bitcoin Evangelism – Became one of Bitcoin’s most vocal advocates, encouraging corporations and institutions to adopt BTC and blockchain. 2022: Stepped down as CEO – Transitioned to Executive Chairman to focus entirely on Bitcoin strategy.   With a major focus on blockchain network growth, Saylor is considered one of the architects in shaping the growth of decentralized finance.   Useful Links to connect with Michael Saylor Platform Link to connect Micro Strategy (Strategy) Official Website MicroStrategy Michael Saylor’s YouTube Channel https://www.youtube.com/c/MichaelSaylor Hope.com (Bitcoin Education by Saylor) Bitcoin is Hope     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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