Trump's crypto mentor's $653 million Bitcoin bet—why Wall Street isn't buying in?
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Trump's crypto mentor's $653 million Bitcoin bet—why Wall Street isn't buying in?
The stock price of this Bitcoin treasury company plummeted from $25 to 92 cents within six months.
Navigating Web3 tides with focused insightsBy Nina Bambysheva, Forbes
Translated by Luffy, Foresight News
In David Bailey’s words, the past six months have been “a Saving Private Ryan-level battle.” The 35-year-old CEO of Nakamoto Holdings—the digital treasury firm he founded to manage corporate Bitcoin reserves—has watched his boldest bet, a merger with Utah-based publicly traded healthcare company KindlyMD, evolve from an initial victory into today’s trial.
“I’ve been busy getting beaten up in the stock market,” he said. The company’s share price has plummeted from $25 to 92 cents over six months.
Bailey is not your typical Nasdaq-listed executive. He is better known as CEO of Bitcoin Magazine, organizer of the world’s largest Bitcoin conference, and a key figure behind Donald Trump’s shift in stance on cryptocurrency. “Our goal,” he says, “is to become the number one Bitcoin company in the world.”
In May this year, Utah-based KindlyMD—a publicly listed operator of medical clinics offering conventional and alternative therapies with $2.7 million in annual revenue—announced a reverse merger with Bailey’s Nakamoto Holdings, aiming to transform into a Bitcoin holding company. The merged entity is listed on Nasdaq under the ticker NAKA and currently holds approximately $653 million worth of Bitcoin.
Wall Street has shown little faith in Bailey’s plan. After peaking near $35 in May, the stock spent most of October trading below $1, representing a 98% discount to the net asset value implied by its holdings of 5,765 Bitcoins.
Nakamoto Holdings has become a victim of its own fundraising strategy. To raise capital for cryptocurrency purchases, the company completed a series of private investments in public equity (PIPE) deals totaling around $563 million. These transactions issued hundreds of millions of new shares at steep discounts to private investors, significantly diluting existing shareholders. In September, when a large volume of PIPE shares became freely tradable, investors rushed to cash out profits, triggering a collapse in the stock price. Bailey’s letter urging short-term speculators to exit the stock only poured fuel on the fire.
“Investors who are here purely for trading represent an extremely costly source of capital for us,” Bailey said. “I know some people disagree with that view, but we need long-term aligned partners. This is an all-in gamble for us.”
In fact, Bailey says he will soon merge his other businesses—including BTC Inc., the parent company of Bitcoin Magazine, the Bitcoin Conference, and consulting operations, as well as UTXO Management, which owns hedge fund 210k Capital and venture firm 2140—into KindlyMD. Forbes estimates these entities could add up to $200 million in value to the Bitcoin treasury firm while increasing Bailey’s ownership stake (currently 3%).
Bailey declined to comment on Forbes’ valuation figures but said cash flows from these profitable businesses will help KindlyMD purchase more Bitcoin. According to sources familiar with the matter, 210k Capital’s assets under management have quietly grown fourfold from about $100 million in January to $400 million this year.
The emerging financier’s logic is simple: Michael Saylor holds over 600,000 Bitcoins and doesn’t have or need many operating businesses. Other players must pursue differentiated strategies to justify their existence.
“We need to do things that create value,” Bailey said. “Operating real companies is one way to do that.”
Although KindlyMD is headquartered in Salt Lake City, Utah, Bailey primarily works from his home in Guaynabo, Puerto Rico. During video calls, he often sits in front of a large painting depicting a bank engulfed in flames. Created by crypto artist Cypherpunk Now, the piece—titled *Burning Bank*—is one of hundreds in Bailey’s collection.
“Every time I meet with bankers, I make sure that painting is visible in the background,” he jokes. For someone trying to build his own bank, the scene couldn’t be more fitting.
Bailey grew up on a farm in Fayetteville, Tennessee, about an hour’s drive south of Nashville. He developed an early fascination with money and markets. In 2009, he enrolled at the University of Alabama to study economics, finance, and mathematics, aspiring to become an investment banker.
“I was a huge Warren Buffett fan—I attended every single Berkshire Hathaway shareholder meeting in college. I never imagined I’d end up buying Bitcoin; it was completely alien to who I was back then,” he recalled.
In 2012, a friend sent him an article about Bitcoin, and everything began to change. Bailey initially thought Bitcoin was a scam—but couldn’t prove it. In November that year, when Bitcoin fluctuated between $10 and $12, he made his first investment.
In 2014, one year after graduation, Bailey joined *Bitcoin Magazine*, an early publication focused on the nascent cryptocurrency, co-founded by Vitalik Buterin, who later created Ethereum. Soon after, Bailey and his college friend Taylor Evans acquired the magazine through their jointly founded company, BTC Inc.
To expand the brand’s reach, the duo launched the Bitcoin Conference in 2019. What began as a festival-like gathering has since become the “Coachella of crypto” and established Bailey as one of Bitcoin’s most influential evangelists. Last year’s event in Nashville drew 35,000 attendees—devotees, investors, and politicians—including presidential candidate Donald Trump.
Bailey says his connection with Trump began with a conversation in Puerto Rico in 2024: how to get the president interested in Bitcoin. “Paul Manafort was the original gatekeeper who helped us enter his circle,” he said. Soon, Bailey’s team was granted permission to pitch at Trump Tower. The core message was simple: Bitcoin voters would play a decisive role in the presidential election. Ever the dealmaker, Trump agreed to meet—if Bailey and his allies could deliver votes and grassroots support, the crypto industry would earn a voice.
“Trump turns everything into a season of *The Apprentice*; you’re always auditioning,” he added. “‘Okay, you want to be the Bitcoin advisor? I’ll bring in three other people to compete for the spot.’” Bailey ultimately won. He united industry leaders to raise over $100 million for Trump’s campaign, including $21 million raised at the Nashville conference alone. It was there that Trump famously pledged to make America the global capital of cryptocurrency.
“He was very skeptical at first, but the crowd’s cheers changed his mind. As he left, he said, ‘These Bitcoin guys love me—they’re my people,’” Bailey recalled. Today, he serves as an informal adviser to the president. In his view, Trump simply realized that cryptocurrency had been treated differently from every other asset class (after the election, Trump reportedly earned hundreds of millions from crypto). He believes the current goal is to level the playing field, with the broader vision of making America the most Bitcoin-friendly nation globally.
Bailey claims that over his 13-year career, he has invested in over 100 Bitcoin-related companies, with top performers like Metaplanet and Smarter Web turning millions in investments into hundredfold returns. He says the rewards go beyond finance—good ideas get replicated. “If tens of thousands of Bitcoin companies thrive, we win.”
This Buffett-inspired long-term vision now drives KindlyMD. Bailey envisions building a large holding company with profitable, independently operated subsidiaries. For him, this isn’t just an investment strategy—it’s a replay of monetary history. His concept of a “Bitcoin standard” echoes the evolution of gold: silver and gold traders evolved into banks, then central and investment banks. He sees today’s Bitcoin treasury firms as the digital-age equivalent of those early bullion traders, evolving toward a new kind of banking.
KindlyMD is advancing this transformation. The company has invested in other Bitcoin holding firms, including Japan’s Metaplanet and Treasury B.V. in the Netherlands. “Imagine nurturing an ETF,” Bailey explains. “That’s exactly what we’re doing—cultivating these actively managed ETFs across the globe, in the form of corporate equities.” Of course, like other newly formed crypto treasury firms, Bailey’s entry into public markets sidesteps SEC scrutiny over ETFs and IPOs.
Despite KindlyMD’s disastrous debut on Wall Street, Bailey remains unfazed. “One of the best things about Bitcoin is that it’s incredibly forgiving—you can make mistakes in your career and start over,” Bailey said.
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