The post Bitcoin News: Is Strategy Under Too Much Debt? $2B Bond Sale Raises Questions appeared first on Coinpedia Fintech News
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 J. Saylor is an enthusiastic blockchain influencer and a splendid leader. He is an entrepreneur and business executive who co-founded Microstrategy, he is chairman and CEO of the same Microstrategy. He is a vocal advocate of Bitcoin. He is highly skilled in enterprise software and also has a rich knowledge of numerous fields, including analytics, data warehouses, leadership, SaaS, management, cloud computing, startups, professional services, enterprise architecture, mobile devices, and many more.
Location: United States
Education :
He graduated from MIT in 1987 with a double major in aeronautics, science, technology, and society.
Experience:
He has been an Executive Chairman & Founder at MicroStrategy from Aug 2022 - Present
He was also Chairman, CEO & Founder of MicroStrategy from Oct 1989 to Aug 2022
Skills: Buisness Intelligence and Data warehousing
Net Worth: Saylor's net worth is about $4.6 billion, according to Forbes. He also held 2.4 million shares of MicroStrategy
Events Attended: Bitcoin 2024 Nashville and BTC prague
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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As of 2025, Strategy holds over 478,740 BTC, making it the largest corporate Bitcoin holder, with purchases funded by debt and equity.
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