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 investment 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 Strategy has made Bitcoin their primary treasure reserve. He is a vocal advocate and Top Bitcoin Speaker who participates in various Bitcoin and Crypto events. Michael Saylor is highly skilled in and has a rich knowledge of numerous fields, including analytics, data warehouses, SaaS, management, cloud computing, enterprise architecture, mobile devices, and many more.   Personal Details: Born: Feb 4, 1965Location: United StatesGraduation: He graduated from MIT in 1987 with a double major in aeronautics, science, technology, and society.    Michael Saylor – Career Timeline 1983–1987: Studied Aeronautics & Astronautics and Science, Technology & Society at Massachusetts Institute of Technology (MIT). 1989: Co-founded MicroStrategy (Strategy). 1998: MicroStrategy IPO – Took MicroStrategy public on the NASDAQ at $12 per share. 2000: Accounting Scandal & Crash – MicroStrategy's stock plunged 62% in a day due to an accounting misstatement, wiping out billions in valuation. 2004–2019: MicroStrategy Rebuilds – Worked towards cloud-based analytics and AI-driven business intelligence, regaining stability. 2020: Bitcoin Strategy & Investment – Led MicroStrategy’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.     [email protected] 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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