Trump advisor lost 99% on his Bitcoin bet, now he’s fighting to rebuild

David Bailey built Nakamoto Holdings as a Bitcoin treasury company modelled on Strategy's playbook, raise capital through equity markets, buy Bitcoin, hold it.

The company was created through the merger of Bailey's Nakamoto Holdings with healthcare company KindlyMD, backed by a $510 million private investment and $200 million in convertible notes.

As reported by Bloomberg, Nakamoto's stock has since collapsed approximately 99% from its 2025 peak.

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The company reported a net loss of $371.8 million for the first six months of 2026, according to its latest SEC filing. By the end of June it held approximately 4,467 Bitcoin worth roughly $261.5 million, and $19.1 million in cash against $164.7 million in total debt.

The reverse split that kept it alive

The collapse in Nakamoto's stock forced the company to carry out a 1-for-40 reverse split in May 2026 to regain compliance with Nasdaq's $1 minimum bid-price requirement, reducing outstanding shares from approximately 696.1 million to roughly 17.4 million, according to the SEC filing in May.

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