Trump advisor’s Bitcoin-focused company faces massive losses and strategic shift

David Bailey, a former Trump advisor, founded Nakamoto Holdings as a Bitcoin treasury firm modeled after MicroStrategy. The company was formed through the merger with KindlyMD and backed by $510 million in private investment and $200 million in convertible notes. However, its stock has plummeted nearly 99% from its peak in early 2025. According to an SEC filing, Nakamoto reported a net loss of $371.8 million for the first half of 2026 and is now holding around 4,467 Bitcoin worth approximately $261.5 million against total debt of $164.7 million. To stay listed on Nasdaq, it executed a 1-for-40 reverse stock split in May 2026. Bailey has shifted strategy from issuing equity to acquire more Bitcoin toward seeking acquisitions that can improve cash flow and income while supporting the company’s broader cryptocurrency goals. Nakamoto recently sold about 600 Bitcoin for $48 million, using most of it to repay debt.

By Bibhu Pattnaik · TheStreet ·

Trump advisor’s Bitcoin-focused company faces massive losses and strategic shift

Tickers: $NAKA

Topics: Bitcoin company strategy shift reverse_split SEC filings

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