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Trump adviser lost 99% on his Bitcoin investment and is now struggling to rebuild

2026-09-04 00:37:45
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David Bailey builds Nakamoto Holdings: From Bitcoin Treasury Model to Strategic Transformation

David Bailey founded Nakamoto Holdings with the aim of building a Bitcoin Treasury Company that mimics the Strategy model. The core logic is to raise funds through the equity market to buy and hold Bitcoin. The company was formed by the merger of Bailey's Nakamoto Holdings and healthcare company KindlyMD, backed by $510 million in private equity investment and $200 million in convertible notes.

According to Bloomberg, Nakamoto's share price has plunged about 99% since peaking in 2025. According to its latest filing with the U.S. Securities and Exchange Commission (SEC), the company reported a net loss of $371.8 million in the first half of 2026. As of the end of June, the company held approximately 4,467 bitcoins worth approximately $261.5 million, and $19.1 million in cash, while total debt was $164.7 million.

Reverse split to maintain listing status

The collapse of Nakamoto's share price forced the company to conduct a 1 - 40 reverse split in May 2026 to regain compliance with Nasdaq's minimum $1 bid requirement. According to an SEC filing in May, the split reduced the number of shares outstanding from approximately 696.1 million shares to approximately 17.4 million shares.

Bailey told Bloomberg that the company is now seeking acquisition opportunities that can improve revenue and cash flow while supporting its broader Bitcoin strategy. This marks a significant departure from the company's previous model of relying on issuing shares to accumulate Bitcoin.

"We are looking for companies that can help us increase our company's revenue and cash flow. We are also looking for businesses that have strategic value to Bitcoin as a whole,"Bailey said.

As the stock price is lower than the value of the Bitcoin it holds, the strategy of issuing new shares to fund additional cryptocurrency purchases is no longer economically feasible.

Strategic adjustments and balance sheet pressures

Balance sheet pressures have forced companies to take concrete actions. Nakamoto sold about 600 positions in Bitcoin and related derivatives, earning a net gain of about US$48 million, most of which was used to repay US$45 million in Bitcoin mortgage debt.

The board of directors approved a share repurchase plan of up to $25 million in June. In addition, according to the company's announcement, the company also reduced debt and extended the maturity date of approximately USDT principal of approximately 105 million to June 2027.

A separate statement stated that the company completed a review of BTC Inc. in February. and UTXO Management, issued approximately $81.6 million worth of shares, bringing Bailey's own media and investment businesses into Nakamoto's portfolio.

Widespread reversal of Bitcoin Treasury stocks

Nakamoto's dilemma is part of a broader reversal of Bitcoin Treasury stocks. According to the Financial Times, the market value of companies built around holding Bitcoin has evaporated by more than $80 billion since mid-2025, as the premium relative to their cryptocurrency holdings has disappeared.

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