Michael Saylor’s corporate Bitcoin pile — held by his company formerly known as MicroStrategy (now Strategy, Inc.) — has dipped below its average purchase priceMichael Saylor’s corporate Bitcoin pile — held by his company formerly known as MicroStrategy (now Strategy, Inc.) — has dipped below its average purchase price

Michael Saylor’s Bitcoin Hoard Is Underwater — But Not About to Press the Panic Button

However, underwater doesn’t mean forced to sell. Strategy’s stash isn’t pledged as collateral in any way that could trigger margin calls or fire sales. There’s no ticking clock or liquidation mechanic that says they have to dump coins just because the price dipped below their cost basis.

So what actually happens when you’re sitting on a loss like this? Two big impacts — and neither is a panic trigger:

  1. Fundraising gets harder: Historically, Strategy funded more Bitcoin buys by issuing new shares through at-the-market offerings (ATM). That only works well when the stock trades at a premium to the net asset value (NAV) of its BTC holdings. With Bitcoin down, Strategy’s share price now trades at a discount to NAV, meaning that selling stock dilutes shareholders more, making future capital raises less attractive.
  2. Buying slows, it doesn’t stop: With the stock trading lower relative to BTC value, the company’s ability to fund big Bitcoin purchases without diluting shareholders is constrained. This isn’t existential — it’s tactical. In 2022, when a similar discount persisted, Strategy added only about 10,000 Bitcoin over the whole year.

On the other side of the ledger: Strategy’s debt load — roughly $8.3B in convertible notes — looks scary at a glance, but that debt doesn’t force near-term Bitcoin sales either. They can roll maturities or convert debt into equity, and the first major notes aren’t due until late 2027.

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