Strategy Boosts Bitcoin Holdings While Nakamoto Holdings Enters the Market

Strategy Boosts Bitcoin Holdings While Nakamoto Holdings Enters the Market Bitcoin continues to gain traction among institutional players, as two significant developments this week highlighted the asset’s growing role on corporate balance sheets. Michael Saylor’s Strategy announced the purchase of an additional $1.34 billion in Bitcoin, raising its total holdings to 568,840 BTC. At the same time, healthcare company KindlyMD completed a merger with newly formed Nakamoto Holdings — led by Trump crypto adviser David Bailey — to create a Bitcoin-native treasury firm supported by $710 million in financing. Michael Saylor’s Strategy Buys $1.34B in Bitcoin as BTC Surges Past $100K, Hitting 568,840 BTC in Holdings Bitcoin advocate and Strategy co-founder Michael Saylor has doubled down on his Bitcoin conviction yet again. Between May 5 and May 11, Saylor’s firm, Strategy, purchased an additional 13,390 BTC for approximately $1.34 billion as Bitcoin’s price broke above the $100,000 threshold for the first time in history. The details of the acquisition were revealed in a Form 8-K filing with the US Securities and Exchange Commission (SEC) on May 12. The average purchase price for the latest Bitcoin haul stood at $99,856 per coin, just under the newly reclaimed psychological mark of $100,000, which BTC surpassed on May 8. Following the latest purchase, Strategy’s total Bitcoin holdings now amount to 568,840 BTC, acquired at a total cost of approximately $39.4 billion. The firm’s average acquisition price sits at $69,287 per coin. Strategy's holdings are now valued at more than $58.29 billion — representing a gain of over $18.8 billion on paper. Strategy Bitcoin buyers over time (Source: SaylorTracker ) This 2.4% increase in Strategy's Bitcoin holdings further cements its position as the largest corporate holder of Bitcoin globally, far ahead of public and private companies alike. Strategy Hits 2025 Bitcoin Yield Target Ahead of Schedule Michael Saylor took to X on May 12 to announce that the company had successfully reached its previously stated Bitcoin yield target for 2025. The Bitcoin yield — a proprietary metric used by Strategy to reflect the performance of BTC holdings relative to the company’s diluted share count — climbed to 15.5% following the latest acquisition. The firm had set a 15% BTC yield target for 2025 after posting a staggering 74% yield in 2024. With that milestone now met in early May, Strategy has raised its full-year yield target to an ambitious 25%. Despite Strategy's bullish performance and confidence in Bitcoin as a treasury asset, the move has drawn fresh criticism from long-time Bitcoin skeptic and gold advocate Peter Schiff. Responding to Saylor’s announcement on X, Schiff warned that the rising average purchase price could backfire if Bitcoin undergoes a sharp correction. “Your next buy will likely push your average cost above $70,000,” he wrote, adding that a drop in BTC’s market price could push it below Strategy’s breakeven level. “Not good considering how much you borrowed to buy the Bitcoin,” Schiff warned. “When you sell, small paper losses will become huge real losses.” His remarks refer to Strategy’s leveraged approach to accumulating Bitcoin. Earlier this month, the company disclosed plans to raise up to $42 billion in equity and an additional $42 billion in fixed-income offerings — essentially doubling its capital raise target from previous rounds — to continue funding Bitcoin purchases. Coinbase Steers Clear of Saylor’s Aggressive Model While Schiff’s critiques are often seen as alarmist within the crypto community, even some crypto-native firms appear to be exercising caution. A recent report by Bloomberg revealed that Coinbase, one of the world’s largest cryptocurrency exchanges, has internally discussed adopting a Bitcoin treasury strategy similar to Strategy’s — but opted against it multiple times. The reason? Risk concentration. As Coinbase executives reportedly concluded, overly aggressive Bitcoin buying introduces significant balance sheet exposure that could backfire in a bear market, especially when leverage is involved. Strategy’s latest purchase sheds light on a growing divide in how institutions view Bitcoin as a treasury reserve asset. For some, like Saylor, it is the ultimate store of value — a scarce, deflationary hedge against fiat currency devaluation. For others, it remains too volatile and speculative to serve as a reliable corporate asset. Nevertheless, the results so far have been difficult to ignore. With BTC above $100,000 and Strategy’s BTC holdings deeply in profit, the company’s bold strategy has, at least for now, validated its conviction in Bitcoin’s long-term potential. KindlyMD Merges with Nakamoto Holdings to Create Bitcoin Treasury Powerhouse with $710M in Backing Meanwhile, in a landmark move that shows the growing convergence of healthcare and crypto finance, healthcare services provider KindlyMD has announced its merger with Nakamoto Holdings, a Bitcoin-native holding company spearheaded by David Bailey — a prominent crypto adviser to US President Donald Trump. The merger, revealed on May 12 , marks the birth of a new kind of company: a publicly listed Bitcoin treasury vehicle with ambitions to build a global ecosystem of BTC-native firms. The combined entity aims to become a leader in Bitcoin-centric capital markets, integrating BTC into a wide variety of financial instruments, including equity, debt, and preferred shares. The website of the new Nakamoto company (Source: Nakamoto ) A Bold Mission to Bitcoinize Global Balance Sheets According to Bailey, Nakamoto Holdings’ broader vision is to create a worldwide network of Bitcoin treasury companies that offer compliant, transparent market exposure to BTC. The firm seeks to replicate and build upon the model pioneered by Michael Saylor’s Strategy, formerly known as MicroStrategy. Long-term, the firm aims to extend beyond Bitcoin accumulation and into media, advisory, and financial services to catalyze Bitcoin utility and mass adoption. The merger places Bitcoin at the heart of the company’s financial structure, with plans to grow BTC held per share — a metric closely monitored by Bitcoin-forward companies like Strategy. Shares of KindlyMD will continue to trade on Nasdaq under the ticker “KDLY” until the deal is finalized. Following the completion of the merger, the newly combined company will be renamed and begin trading under a new ticker that reflects its Bitcoin -first identity. The boards of both Nakamoto Holdings and KindlyMD have unanimously approved the transaction. However, the deal still requires shareholder approval from KindlyMD to proceed. Upon closing, the new firm will inherit all prior business relationships and obligations of Nakamoto Holdings — including its marketing partnership with BTC Inc., the publisher of Bitcoin Magazine and organizer of the annual Bitcoin Conference. Massive $710M Financing Package to Accelerate BTC Strategy In a clear signal of institutional support, the deal includes $710 million in financing, divided into two main components: $510 million in gross proceeds from a private placement in public equity (PIPE), priced at $1.12 per share. The placement includes a mix of common stock and pre-funded warrants issued by KindlyMD. $200 million in gross proceeds from the sale of senior secured convertible notes, maturing in 2028. The capital raised will be used to aggressively accumulate Bitcoin and fund the development of new BTC-native financial instruments. The financing is expected to close in tandem with the merger itself. David Bailey has made no secret of his admiration for Michael Saylor’s approach to building a Bitcoin treasury. Like Saylor’s Strategy, the new company will use equity and debt offerings to finance Bitcoin purchases — but with a greater emphasis on integrating BTC into global capital markets through diverse, exchange-listed products. By merging the healthcare-focused infrastructure of KindlyMD with Nakamoto Holdings’ crypto-first strategy, the new entity represents a novel fusion of traditional industry and digital asset finance. Bitcoin’s Institutional March Continues This merger adds momentum to a broader institutional trend that has seen Bitcoin increasingly embraced as a core balance sheet asset. While MicroStrategy continues to set the benchmark with over 568,000 BTC in holdings, newcomers like Nakamoto Holdings are entering the market with ambitious capital-raising and acquisition plans. Bailey’s close ties to the Trump administration also raise the possibility that this merger could serve as a template for other publicly listed companies to pivot toward BTC-based treasury strategies — particularly if a second Trump term fosters more favorable crypto regulation. If shareholder approval is secured and the merger finalizes, the new company will become one of the few publicly listed firms with a Bitcoin-first mandate, supported by significant institutional capital and strategic relationships across the crypto industry. With $710 million ready to deploy, a growing Bitcoin price above $100,000, and political winds increasingly blowing in Bitcoin’s favor, KindlyMD and Nakamoto Holdings may be positioned to become a central player in Bitcoin’s institutional expansion. ENRICH your inbox with our best stories