Original Title: Trump’s Crypto Adviser’s Quixotic Quest To Build A Leading Bitcoin Bank
Author: Nina Bambysheva, Forbes
Original Compilation: Luffy, Foresight News
In David Bailey’s words, the past six months have been nothing short of a “Saving Private Ryan-style brutal battle.” The 35-year-old CEO of Nakamoto Holdings—a digital treasury company he founded to manage corporate bitcoin reserves—has witnessed his boldest gamble yet: the merger with KindlyMD, a small publicly traded healthcare company in Utah, evolve from an initial victory into a current trial.
“I’ve been busy taking a beating in the stock market,” he said. The company’s share price has plummeted from $25 to 92 cents within six months.
Bailey is not your typical Nasdaq-listed company executive. He is better known as the CEO of Bitcoin Magazine, the organizer of the world’s largest Bitcoin conference, and the key figure who influenced Donald Trump’s shift in attitude towards cryptocurrencies. “Our goal,” he stated, “is to become the number one Bitcoin company globally.”
In May this year, KindlyMD, a Utah-based listed medical clinic operator with annual revenues of $2.7 million providing both conventional and alternative therapies, 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 symbol NAKA and currently holds approximately $653 million worth of Bitcoin.
Wall Street is not optimistic about Bailey’s plan. After peaking at nearly $35 per share in May, the stock spent most of October trading below $1, representing a 98% discount to the net value of the 5,765 Bitcoins held on its balance sheet.
It turns out that Nakamoto Holdings fell victim to its own financing strategy. To raise capital for cryptocurrency purchases, the company executed a series of private investment in public equity (PIPE) deals totaling approximately $563 million. These transactions issued hundreds of millions of new shares to private investors at steep discounts, significantly diluting existing shareholders’ equity. In September, a large volume of PIPE shares became unrestricted and flooded the market, prompting investors to rush for profits, which triggered a collapse in the stock price. Bailey’s letter to shareholders urging short-term speculators to exit the stock further exacerbated the situation.
“Those investors who come only for trading are, in fact, an extremely costly source of capital for us,” Bailey said. “I know some people disagree with this view, but what we need are long-term partners whose interests are aligned with ours. For us, this is an all-or-nothing gamble.”
In fact, Bailey stated that he would soon merge his other businesses— including BTC Inc., the parent company of Bitcoin Magazine, Bitcoin conferences, and consulting services, as well as UTXO Management, which owns the hedge fund 210k Capital and venture capital firm 2140—into KindlyMD. Forbes estimates that these entities could add up to $200 million in value to this Bitcoin treasury company while increasing Bailey’s ownership stake (currently at 3%).
Bailey did not comment on Forbes’ figures, but said that the cash generated from these profitable businesses would help KindlyMD purchase more Bitcoin. According to sources familiar with the matter, the assets under management of 210k Capital alone have quietly grown from about $100 million in January this year to $400 million, representing a fourfold increase.
The logic of this up-and-coming financier is simple: Michael Saylor holds more than 600,000 Bitcoins and does not need or rely on significant operational businesses. Other players must adopt differentiated strategies to justify their existence.
“We need to do things that create value,” Bailey said. “Running operational businesses is one way to achieve that.”
Although KindlyMD’s headquarters is located 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. The artwork, titled “Burning Banks,” was created by crypto artist Cypherpunk Now and is one of hundreds of pieces in Bailey’s collection.
“Every time I meet with bankers, I make sure this painting appears in the background,” he said with a smile. For someone looking 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. From an early age, he developed a strong interest in money and markets. In 2009, he entered the University of Alabama to study economics, finance, and mathematics, aspiring to become an investment banker.
“I used to be a huge fan of Warren Buffett and attended every Berkshire Hathaway annual meeting during my college years. I never imagined that I would buy Bitcoin—it was completely out of character for me at the time,” he recalled.
In 2012, a friend sent him an article about Bitcoin, and everything began to change. Initially skeptical of Bitcoin as a scam, Bailey could not substantiate this claim. In November of the same year, when Bitcoin’s price was fluctuating 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 emerging cryptocurrency, co-founded by Vitalik Buterin, who later established Ethereum. Soon after, Bailey and his college friend Tyler Evans acquired the magazine through their jointly founded BTC Inc.
To expand the brand’s influence, the two launched the Bitcoin Conference in 2019. This festival-like event has now become the “Coachella of the crypto world,” also making Bailey one of the most influential advocates for Bitcoin. Last year’s conference in Nashville attracted 35,000 believers, investors, and politicians, including then-presidential candidate Donald Trump.
Bailey stated that his interaction with Trump began with a conversation in Puerto Rico in 2024: how to get the president interested in Bitcoin. “Paul Manafort was the initial gatekeeper who helped us enter his circle,” he said. Soon, Bailey’s team was granted a presentation opportunity at Trump Tower. The core message was simple: Bitcoin voters would play a key role in the presidential election. Always a dealmaker, Trump decided to meet, and if Bailey and his associates could deliver votes and support, the cryptocurrency industry would gain a voice.
“Trump turns everything into an episode of ‘The Apprentice’; you’re always auditioning,” he added. “‘Okay, you want to be the Bitcoin advisor? I’ll bring in three more people to compete for the position.'” Bailey ultimately prevailed, uniting industry leaders to raise over $100 million for Trump’s campaign, with the Nashville conference alone contributing $21 million. At that event, Trump’s famous pledge—to make the United States the global capital of cryptocurrency—gained widespread recognition.
“He was initially very uncertain, but the cheers from the live audience changed his attitude. As he left, he said, ‘These Bitcoin enthusiasts like me; they’re my people,'” Bailey recalled. Today, he serves as an informal advisor to the president. In his view, Trump simply recognized that cryptocurrencies were treated differently from all other asset classes (since the election, Trump has profited hundreds of millions from the crypto sector). The goal now, he believes, is to create a level playing field, with the broader vision of making the U.S. the most Bitcoin-friendly country for businesses globally.
Bailey claims that over the course of his 13-year career, he has invested in more than 100 Bitcoin-related companies, with the top performers, Metaplanet and Smarter Web, turning millions of dollars into returns exceeding 100 times the original investment. He noted that the returns were not only financial; good ideas tend to be replicated. “If thousands of Bitcoin companies thrive, we win.”
This long-term perspective, inspired by Buffett, is now driving KindlyMD’s development. Bailey envisions it as a large holding company with profitable and independently operated subsidiaries. For him, this is not only an investment strategy but also a reenactment of monetary history. His concept of a “Bitcoin Standard” echoes the evolution of gold: gold and silver traders evolved into gold and silver banks, which then developed into central and investment banks. He believes that today’s Bitcoin treasury companies are the digital-age equivalents of gold and silver traders, evolving toward a new form of banking.
KindlyMD is facilitating this transformation. The company has invested in other Bitcoin holding companies, such as Japan’s Metaplanet and the Netherlands’ Treasury B.V. “Imagine nurturing an ETF,” Bailey explained, “What we’re doing is exactly that—cultivating actively managed ETFs globally in the form of corporate stocks.” Of course, like other newly established crypto treasury firms, Bailey’s entry into the public market sidesteps the SEC’s scrutiny of ETFs and IPOs.
Despite KindlyMD’s disappointing Wall Street debut, Bailey isn’t too concerned. “The best thing about Bitcoin is its forgiveness—you can make mistakes in your career and start over,” Bailey said.
