Michael Saylor and Other Crypto Leaders Suffer Major Losses After October Market Crash

In October 2025, key figures in the cryptocurrency industry experienced a significant decline in their personal wealth due to a sudden market downturn, erasing earlier gains made throughout the year.

Key Takeaways:

An October market crash caused billions in losses for prominent crypto executives following earlier gains.
Michael Saylor, CZ, and the Winklevoss twins faced substantial reductions in their wealth as Bitcoin and related assets plummeted.
Despite this volatility, the adoption of Bitcoin by corporations is still on the rise, with 192 public companies now holding Bitcoin.

According to the Bloomberg Billionaires Index released this past Wednesday, Michael Saylor, the executive chairman of Strategy, saw a $2.6 billion drop in his wealth over the last year, leaving him with a net worth of $3.8 billion.

These staggering losses were triggered by an October flash crash that significantly dropped Bitcoin and shares related to cryptocurrency after several months of strong performance.

Michael Saylor, Crypto Titans Lost Billions After October Market Crash

Market Downturn Negates Gains from Strategy’s Bitcoin Investments

Bloomberg highlighted that Strategy’s assertive Bitcoin treasury strategy initially reaped considerable benefits until early October when Bitcoin reached new all-time highs. However, this positive trend quickly reversed as Bitcoin prices fell sharply, leading to a more than 50% decline in Strategy’s stock price and nearly a $6 billion reduction in Saylor's assets from the peak.

Other notable figures in the crypto space also faced losses. Changpeng Zhao, or CZ, experienced around a 5% drop in his wealth since the beginning of the year, bringing his estimated net worth down to $50.9 billion, as reported by Bloomberg.

The Winklevoss twins, Cameron and Tyler, were similarly affected, losing approximately 59% of their combined wealth as the prices of cryptocurrencies decreased and trading volumes slowed down.

In a broader context, these losses starkly contrasted with trends in billionaire wealth, as Bloomberg noted that only eight individuals represented about 25% of the $2.2 trillion in total gains among billionaires in 2025, illustrating a divided landscape across industries.

Not Every Crypto Executive Suffered

Not all leaders in the cryptocurrency sector faced downturns. Jeremy Allaire, the CEO of stablecoin issuer Circle, increased his net worth by 149% since June, supported by rising interest in dollar-backed stablecoins and the recent passage of the US GENIUS Act, which established a regulatory framework for payment stablecoins.

Even amidst the current market fluctuations, corporate interest in digital asset treasuries continues to gain traction. Data from Bitcointreasuries.net indicates that 192 public companies now include Bitcoin in their balance sheets, marking a sharp increase from the previous year.

However, Bitcoin itself is facing challenges. The cryptocurrency has declined approximately 7% since the beginning of 2025, following a peak above $126,000 in October, dropping to around $80,000 by late November.

Optimism Surrounds Bitcoin’s Future in 2026

Bitwise Chief Investment Officer Matt Hougan has dismissed the notion that the political landscape in the US will catalyze a significant price surge. Although Bitcoin experienced a rally to new highs earlier in 2025 after Donald Trump’s inauguration, Hougan believes that the current administration is unlikely to generate substantial upside in the market.

Looking towards 2026, opinions in the industry are mixed. Fidelity’s director of global macro research, Jurrien Timmer, suggests that 2026 might serve as a pause year, potentially seeing prices decline to around $65,000.

Conversely, some remain optimistic. Strategy CEO Phong Le argues that Bitcoin's fundamental values have held strong throughout 2025, despite face value price drops. Meanwhile, Bitwise's Matt Hougan has previously stated that he expects 2026 to be a positive year for Bitcoin.

According to Linh Tran, a market analyst at XS.com, Bitcoin's recent price movements reflect the market's response to expectations around monetary policies rather than general economic indicators.