When Bitcoin fell 16% last month, Strategy shareholders lost twice that amount. This is what Michael Saylor's aggressive Bitcoin strategy was designed to do, for better or for worse.

This drop stems primarily from the family’s holdings in the crypto, with a Trump-branded meme coin, Eric Trump’s Bitcoin mining efforts through American Bitcoin and Truth Social — which is largely tied up in Bitcoin — all experiencing substantial financial setbacks.

ALT5 Sigma, which holds WLFI in its treasury, dropped over 80%. Trump Media & Technology Group, the operator of Truth Social, also fell sharply after its $2 billion Bitcoin and crypto holdings lost roughly 25% of value.

American Bitcoin's stock price steadied, recovering partially from the end of a lockup period that sent its shares tumbling earlier this week.

Strategy Inc (NASDAQ:MSTR) shares are trading higher on Wednesday alongside other crypto-linked stocks after Bitcoin

Strive Asset Management, LLC is rated Strong Sell due to extreme losses, speculative business model & lack of earnings. Read more on ASST stock here.

So far, Strategy is winning because the price of Bitcoin and its stock price keep going up. This allows it to access enough capital to buy more Bitcoin while still satisfying all of its obligations. But in a bear market, things become more difficult. And the company clearly believes a bear market is coming.

Stock futures pointed slightly higher Wednesday, a day after major indexes resumed their winning ways with technology and cryptocurrency-tied stocks leading the charge.