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