Meet the Man Who Quietly Raised $710M to Bitcoinize Wall Street (Hint: Not Saylor)

Key Takeaways

• David Bailey, CEO of Bitcoin Magazine’s parent company and founder of Nakamoto Holdings, has quietly raised $710 million to build a Bitcoin-first treasury model for public companies.
• Unlike Strategy’s Michael Saylor, who made headlines by converting corporate reserves into Bitcoin, Bailey’s approach is structural.
• Bailey’s strategy involves merging with public companies, raising capital through equity and debt, and deploying that capital into Bitcoin.
• This marks a new phase of institutional Bitcoin adoption, one that could see Bitcoin embedded deeply in traditional corporate finance, not just held on balance sheets.
  

In the world of Bitcoin evangelists, Michael Saylor has long held the spotlight. His high-profile pivot from business intelligence to Bitcoin billions made him a fixture of financial media. But behind the scenes, another figure has been shaping a quieter, potentially more scalable revolution: David Bailey.

As the CEO of BTC Inc. (parent of Bitcoin Magazine), Bailey has spent years helping shape the intellectual and ideological foundations of the Bitcoin movement. But now, he’s stepping onto the financial battlefield with a radically different mission: to institutionalize Bitcoin at the deepest levels of public market infrastructure.

In 2025, Bailey executed one of the most significant crypto-related capital raises in history: $710 million. Not for a startup. Not for a protocol. But for a publicly traded Bitcoin treasury vehicle, one designed to scale, multiply, and embed Bitcoin into the DNA of Wall Street.

Let’s break down how it works and why it matters.

Bailey’s $710 Million Blueprint: Capital + Shell + Bitcoin

David Bailey’s strategy isn’t just about holding Bitcoin. It’s about designing a repeatable system that allows public companies to raise capital, convert that capital into BTC, and offer investors exposure to Bitcoin via traditional stock exchanges.

Here’s how the model works:

1. Find a public company: In this case, Bailey’s Nakamoto Holdings merged with KindlyMD , a small-cap healthcare company listed on the Nasdaq.
2. Raise institutional capital: A total of $510 million was raised via a Private Investment in Public Equity (PIPE), supplemented by $200 million in convertible notes.
3. Deploy capital into Bitcoin: The goal is to convert these funds into Bitcoin holdings, establishing a corporate treasury backed by BTC, but with the infrastructure and transparency of a listed company.
4. Repeat: The playbook isn’t designed to be one-of-a-kind. It’s designed to be modular, scalable, and replicable across industries.
   

This marks a major shift from the model pioneered by Michael Saylor, which was built on Strategy’s internal capital (initially) and bold CEO conviction. 

Bailey’s version? 

Think of it as a Bitcoin deployment pipeline for Wall Street.

Institutional Grade Meets Bitcoin Maximalism?

Bailey’s play has already attracted a wide spectrum of investors, from crypto veterans to traditional hedge funds. This mix signals a new level of confidence in Bitcoin’s place within the financial system.

But the uniqueness of the model isn’t just in the amount raised. It’s in how structured and repeatable it is:

• PIPEs (Private Investment in Public Equity)  are a familiar vehicle in public markets, often used by hedge funds and private equity.
• Convertible debt offers optionality, allowing investors to convert to equity down the line while giving companies immediate access to cash.
• Public shell mergers cut through the red tape of traditional IPOs, speeding up timelines and reducing costs.
  

By combining these elements, Bailey isn’t just betting on Bitcoin. He’s building the financial rails to bring Bitcoin into every boardroom.

Why Bailey’s Approach Matters More Than You Think

Bailey’s approach matters because:

• It lowers the barrier to entry: Not every company has the conviction or capital reserves of Strategy. Bailey’s system provides an off-the-shelf model for public firms to gain Bitcoin exposure without reinventing their business model.
• It brings Bitcoin to Wall Street’s front door: Most institutional investors still don’t hold Bitcoin directly. This strategy offers them a familiar vehicle, public equity, with the upside of Bitcoin exposure.
• It unlocks capital markets for crypto treasuries: This isn’t a proxy. These are real Bitcoin purchases, funded by real capital market tools. It’s the bridge between two financial universes that used to speak different languages.
• It could spark a new asset class: If this model takes off, we may soon see multiple companies designed purely as Bitcoin treasuries, just like real estate trusts or commodity ETFs. Think of them as Bitcoin Trust Enterprises.

Saylor vs. Bailey: Two Roads to Bitcoin Institutionalization

Here’s how Saylor and Bailey’s approaches differ:

Bailey isn’t trying to be the next Saylor. He’s perhaps building the infrastructure for future Bitcoin entrepreneurs.

Who Is David Bailey? A Quick Background

David Bailey is a key architect of Bitcoin’s institutional future, though he didn’t emerge from Wall Street or Silicon Valley. A graduate of the University of Alabama, he studied economics with a strong interest in Austrian theory and libertarian monetary principles, ideals that aligned naturally with Bitcoin.

Bailey entered the crypto space early, co-founding BTC Media in 2014. The company went on to acquire and grow Bitcoin Magazine, turning it into one of the industry’s most influential publications. He also launched the Bitcoin Conference, now the world’s largest Bitcoin-only event, attracting policymakers, developers, and global investors.

Over the years, Bailey became a behind-the-scenes strategist, advising startups and institutions on token models, capital formation, and crypto policy. He is also a general partner at UTXO Management, focused on institutional Bitcoin strategy.

His latest venture, Nakamoto Holdings, reflects a shift from advocacy to financial engineering. With a $710 million capital raise and a strategy to merge with public companies to build Bitcoin treasury vehicles, Bailey is helping design the infrastructure that could normalize Bitcoin on corporate balance sheets—quietly, efficiently, and at scale.

Bailey’s journey mirrors Bitcoin’s own evolution: from ideology to infrastructure.

What Could Bailey’s Move Mean for the Market?

Bailey’s success with Nakamoto Holdings may signal the emergence of a new type of financial instrument: publicly traded Bitcoin-native companies that offer asset exposure without relying on mining, exchanges, or wallets.

In this model:

• Investors access Bitcoin exposure through regulated public equities.
• Companies gain a framework to update their treasury strategies for the digital era.
• Wall Street finds a way to engage with Bitcoin without overhauling existing compliance or custody systems.
  

Over time, you could see these entities treated like Bitcoin holding trusts, with valuations driven not just by BTC price, but also treasury strategy, yield generation, and balance sheet management.

This could portray Bitcoin as a financial operating system, not just a store of value.

Conclusion

David Bailey’s work reflects a subtle yet meaningful step in Bitcoin’s ongoing development.
The focus is shifting from simply believing in BTC to building the infrastructure that enables institutions to securely hold, manage, and use it at scale.

While Michael Saylor demonstrated what a bold corporate adoption of Bitcoin can look like, Bailey is helping lay the groundwork for broader institutional involvement. His approach doesn’t just welcome Wall Street, it offers the tools and frameworks needed to integrate Bitcoin into existing financial systems.

Bitcoin’s next phase may not be driven by social media buzz or high-profile events. Instead, it will likely unfold through structured financial agreements, regulatory filings, and quiet entries on audited balance sheets.

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