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

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What started successful 2020 arsenic a bold determination to enactment immoderate spare currency into Bitcoin has, 5 years later, turned MicroStrategy (now rebranded arsenic Strategy) into 1 of the largest holders of BTC connected the planet. 

As of precocious May 2025, the institution holds 580,250 Bitcoin (BTC) (about 2.7% of the full supply). Just successful May, Strategy picked up different 4,020 BTC for astir $427 million, funded the mode Michael Saylor likes it: done much preferred stock.

This has been the signifier for years now: raise capital, bargain much Bitcoin, repeat. Saylor’s not shy astir that, either. He’s called Bitcoin “perfected capital” and “economic immortality.” 

At the Bitcoin Atlantis league backmost successful March, helium laid retired a imaginativeness wherever Bitcoin becomes a $200-trillion planetary colony web — for banks, governments, corporations and, eventually, AI.

As a effect of each of this, immoderate investors dainty Strategy banal similar a Bitcoin exchange-traded money (ETF). Others spot it arsenic a high-beta Bitcoin play: When BTC goes up, Strategy goes up faster.

Michael Saylor successful  1992

Did you know? In 1992, MicroStrategy, co-founded by Michael Saylor, secured a pivotal $10-million declaration with McDonald’s to make bundle analyzing the ratio of its promotions.

Saylor’s hodl done volatility attack

It’s nary astonishment that Michael Saylor is often held up arsenic the poster kid for hodling. 

Hodling, a now-legendary typo from a 2013 Bitcointalk post, present colloquially stands for “hold connected for beloved life,” and that’s precisely the point: Buy Bitcoin and support it, nary substance however chaotic the marketplace gets.

Unlike trading, which relies connected timing tops and bottoms, hodling is simply a stake that Bitcoin, implicit the agelong arc of time, volition outperform accepted assets, ostentation and authorities currencies. 

This strategy gained superior traction aft years of marketplace cycles proved 1 happening again and again: Most short-term traders suffer money. Hodlers, connected the different hand, thin to travel retired up — if they tin tummy the volatility. 

How does it consciousness   similar  to HODL

Behavioral concern backs this up: Studies amusement that nonaccomplishment aversion makes radical much apt to merchantability during downturns and miss retired connected recoveries. Hodling flips that publication by removing the panic fastener entirely.

Aside from Strategy, Fidelity, BlackRock and ARK Invest each tally Bitcoin spot ETFs that don’t commercialized successful and out. In fact, onchain information from Glassnode reveals that 63% of Bitcoin’s circulating proviso has remained untouched for astatine slightest 1 year.

Not conscionable different Saylor: How David Bailey is gathering a Bitcoin dynasty

As CEO of BTC Inc and Bitcoin Magazine, David Bailey has spent the past decennary astatine the halfway of Bitcoin media and culture. Now, he’s going overmuch bigger, bringing superior markets, advisory firms and nationalist companies into the premix nether 1 coordinated umbrella.

In April 2025, David Bailey’s concern vehicle, Nakamoto Holdings, merged with KindlyMD, a publically listed company, successful a woody that instantly gave his radical a way to nationalist markets. The recently combined entity raised $710 million, astir of which is being converted into BTC to signifier its ain Bitcoin treasury. 

Bailey’s extremity present is to make a Bitcoin-native conglomerate that mirrors the dynastic concern houses of the past — portion media, portion merchant bank, portion holding company.

But dissimilar Strategy, Bailey’s taking a much dynamic approach. He’s unfastened astir perchance selling BTC astatine marketplace highs to bargain backmost shares, money acquisitions, oregon reallocate erstwhile it makes consciousness (as agelong arsenic it increases BTC per stock successful the agelong run).

Where Saylor leans maximalist and monolithic, Bailey is playing the relation of Bitcoin’s Rothschild, assembling influence, entree and superior into a generational machine.

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

The emergence of crypto fiscal dynasties

In bequest finance, dynasties person historically been defined by much than conscionable their wealth. Families similar the Rothschilds, Rockefellers and Morgans built enduring power done power implicit fiscal infrastructure, governmental entree and cross-generational plus management.

In the crypto space, a comparable signifier is opening to instrumentality shape. Saylor and Bailey, done precise antithetic strategies, are some gathering organizations designed to institutionalize Bitcoin alternatively of simply holding it. 

Both Strategy and Nakamoto Holdings are processing structured, Bitcoin-centric entities with semipermanent superior strategies, treasury frameworks and nationalist marketplace participation. 

While Saylor’s exemplary focuses connected large-scale accumulation and holding, Bailey is taking a more diversified route, integrating Bitcoin media, advisory services and public-facing companies nether a azygous firm structure.

As much superior flows into these long-horizon strategies, Bitcoin’s relation successful semipermanent plus allocation and firm concern is apt to expand, with entities similar Strategy and Nakamoto astatine the forefront.

The broader interaction of a palmy Bitcoin holding strategy

What began with aboriginal movers has turned into a broader inclination arsenic much companies integrate Bitcoin into their treasury strategies.

According to information published successful aboriginal 2025, firm Bitcoin holdings person accrued implicit 580% since 2020, present accounting for much than 3.6% of the full circulating supply.

BTC holdings by category

Notably, successful May 2025, GameStop disclosed the acquisition of 4,710 BTC (a presumption valued astatine astir $513 cardinal astatine the time), marking its introduction into the integer plus space. 

Around the aforesaid time, Trump Media & Technology Group announced a $2.5-billion superior rise to found a Bitcoin treasury, positioning the institution among the larger firm holders successful the market.

Other examples see The Blockchain Group successful France, which acquired 580 BTC to bring its full holdings to 620 BTC. Since announcing its Bitcoin strategy, the institution reported a 225% summation successful its banal price. 

These developments travel akin moves by publically listed firms specified arsenic Block (formerly Square), Tesla and Coinbase, each of which proceed to study Bitcoin holdings successful quarterly disclosures.

With ample firm players acquiring and holding important volumes of BTC, the disposable proviso continues to tighten. That supply constraint, combined with increasing organization involvement via spot ETFs, is contributing to the cognition of Bitcoin arsenic a semipermanent strategical reserve.

As much nationalist and backstage firms follow akin approaches, Bitcoin’s relation successful firm concern appears to beryllium solidifying.

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