Trump's Crypto Insider Just Turned $1 Million Into $100 Million -- And He's Not Done Yet

David Bailey the crypto insider who helped flip Donald Trump into a Bitcoin (BTC-USD) backer just pulled off one of the most aggressive plays in crypto investing. His hedge fund, 210k Capital, notched a 640% return over the past 12 months by backing small public companies that pivoted into Bitcoin holdings. Instead of chasing Bitcoin (or ETFs) directly, Bailey and his team have turned companies in sectors as far-flung as hospitality and web design into Bitcoin treasury vehicles. One example: UK-based Smarter Web, whose stock jumped roughly 14,000% after the shift. 210k Capital now manages $433 million, up from $44 million before the strategy caught fire and it's still scaling.

The biggest winners so far? Metaplanet and Smarter Web. The fund invested early in both putting 780,000 into Smarter Web's pre-IPO round and $1 million into Metaplanet warrants just as each company pivoted to accumulate Bitcoin. Today, those positions are worth about 110 million and $106 million, respectively. Metaplanet's stock has surged over 9,000% since April 2024. Bailey is now on Metaplanet's advisory board, and Trump's son Eric is part of its strategic team. The Trump-Bailey orbit is tight Trump even gave Bailey a public shout-out during a major Bitcoin event last year. Since then, crypto-friendly sentiment has grown louder, and Bailey has been among the most aggressive at monetizing it through public markets.

Looking ahead, 210k Capital isn't slowing down. Managing Partner Tyler Evans says the firm is actively pursuing 30 more Bitcoin proxy deals not just in the U.S. and Europe, but also in markets like India, South Korea, and Southeast Asia, where Bitcoin ETFs haven't launched yet. The goal? Embed with management, engineer the treasury pivot, and ride the wave. It's risky these stocks can be volatile, as seen when Smarter Web dropped 55% from its June peak but if early returns are any sign, this playbook could be one of the most profitable (and unconventional) in crypto's next chapter.