Michael Saylor vs. David Bailey: Different paths toward institutional Bitcoin adoption

What started in 2020 as a bold move to put some spare cash into Bitcoin has, five years later, turned MicroStrategy (now rebranded as Strategy) into one of the largest holders of BTC on the planet. 

As of late May 2025, the company holds 580,250 Bitcoin (about 2.7% of the total supply). Just in May, Strategy picked up another 4,020 BTC for around $427 million, funded the way Michael Saylor likes it: through more preferred stock.

This has been the pattern for years now: raise capital, buy more Bitcoin, repeat. Saylor’s not shy about that, either. He’s called Bitcoin “perfected capital” and “economic immortality.” 

At the Bitcoin Atlantis conference back in March, he laid out a vision where Bitcoin becomes a $200-trillion global settlement network — for banks, governments, corporations and, eventually, AI.

As a result of all of this, some investors treat Strategy stock like a Bitcoin exchange-traded fund (ETF). Others see it as a high-beta Bitcoin play: When BTC goes up, Strategy goes up faster.

Did you know? In 1992, MicroStrategy, co-founded by Michael Saylor, secured a pivotal $10-million contract with McDonald’s to develop software analyzing the efficiency of its promotions.

Saylor’s hodl through volatility approach

It’s no surprise that Michael Saylor is often held up as the poster child for hodling. 

Hodling, a now-legendary typo from a 2013 Bitcointalk post, now colloquially stands for “hold on for dear life,” and that’s exactly the point: Buy Bitcoin and keep it, no matter how wild the market gets.

Unlike trading, which relies on timing tops and bottoms, hodling is a bet that Bitcoin, over the long arc of time, will outperform traditional assets, inflation and government currencies. 

This strategy gained serious traction after years of market cycles proved one thing again and again: Most short-term traders lose money. Hodlers, on the other hand, tend to come out ahead — if they can stomach the volatility. 

Behavioral finance backs this up: Studies show that loss aversion makes people more likely to sell during downturns and miss out on recoveries. Hodling flips that script by removing the panic button entirely.

Aside from Strategy, Fidelity, BlackRock and ARK Invest all run Bitcoin spot ETFs that don’t trade in and out. In fact, onchain data from Glassnode reveals that 63% of Bitcoin’s circulating supply has remained untouched for at least one year.

Not just another Saylor: How David Bailey is building a Bitcoin dynasty

As CEO of BTC Inc and Bitcoin Magazine, David Bailey has spent the past decade at the center of Bitcoin media and culture. Now, he’s going much bigger, bringing capital markets, advisory firms and public companies into the mix under one coordinated umbrella.

In April 2025, David Bailey’s investment vehicle, Nakamoto Holdings, merged with KindlyMD, a publicly listed company, in a deal that instantly gave his group a path to public markets. The newly combined entity raised $710 million, most of which is being converted into BTC to form its own Bitcoin treasury. 

Bailey’s goal here is to create a Bitcoin-native conglomerate that mirrors the dynastic finance houses of the past — part media, part merchant bank, part holding company.

But unlike Strategy, Bailey’s taking a more dynamic approach. He’s open about potentially selling BTC at market highs to buy back shares, fund acquisitions, or reallocate when it makes sense (as long as it increases BTC per share in the long run).

Where Saylor leans maximalist and monolithic, Bailey is playing the role of Bitcoin’s Rothschild, assembling influence, access and capital into a generational machine.

Did you know? Bitcoin Magazine, co-founded by Vitalik Buterin in 2012, is the oldest publication dedicated to Bitcoin. In 2015, it was acquired by BTC Inc, led by David Bailey, who has since expanded it into a global media and events platform, including the annual Bitcoin Conference.

The rise of crypto financial dynasties

In legacy finance, dynasties have historically been defined by more than just their wealth. Families like the Rothschilds, Rockefellers and Morgans built enduring influence through control over financial infrastructure, political access and cross-generational asset management.

In the crypto space, a comparable pattern is beginning to take shape. Saylor and Bailey, through very different strategies, are both building organizations designed to institutionalize Bitcoin instead of simply holding it. 

Both Strategy and Nakamoto Holdings are developing structured, Bitcoin-centric entities with long-term capital strategies, treasury frameworks and public market participation. 

While Saylor’s model focuses on large-scale accumulation and holding, Bailey is taking a more diversified route, integrating Bitcoin media, advisory services and public-facing companies under a single corporate structure.

As more capital flows into these long-horizon strategies, Bitcoin’s role in long-term asset allocation and corporate finance is likely to expand, with entities like Strategy and Nakamoto at the forefront.

The broader impact of a successful Bitcoin holding strategy

What began with early movers has turned into a broader trend as more companies integrate Bitcoin into their treasury strategies.

According to data published in early 2025, corporate Bitcoin holdings have increased over 580% since 2020, now accounting for more than 3.6% of the total circulating supply.

Notably, in May 2025, GameStop disclosed the purchase of 4,710 BTC (a position valued at roughly $513 million at the time), marking its entry into the digital asset space. 

Around the same time, Trump Media & Technology Group announced a $2.5-billion capital raise to establish a Bitcoin treasury, positioning the company among the larger corporate holders in the market.

Other examples include The Blockchain Group in France, which acquired 580 BTC to bring its total holdings to 620 BTC. Since announcing its Bitcoin strategy, the company reported a 225% increase in its stock price. 

These developments follow similar moves by publicly listed firms such as Block (formerly Square), Tesla and Coinbase, all of which continue to report Bitcoin holdings in quarterly disclosures.

With large corporate players acquiring and holding significant volumes of BTC, the available supply continues to tighten. That supply constraint, combined with growing institutional interest via spot ETFs, is contributing to the perception of Bitcoin as a long-term strategic reserve.

As more public and private firms adopt similar approaches, Bitcoin’s role in corporate finance appears to be solidifying.