Michael Saylor and David Bailey champion Bitcoin. Their strategies, however, differ dramatically. One relentlessly accumulates the asset. The other constructs an entire ecosystem. Both aim for institutional adoption. Their contrasting methods reshape corporate finance. This rivalry fuels Bitcoin’s march into mainstream portfolios.
Saylor’s Accumulation Machine
MicroStrategy, now called Strategy, started buying Bitcoin in 2020. It used spare corporate cash initially. Five years later, Strategy holds a staggering 580,250 Bitcoin. That equals roughly 2.7% of all Bitcoin ever mined. Its May 2025 purchase added 4,020 more BTC, for which Strategy spent approximately $427 million. It funded this through preferred stock issuance. This pattern defines Saylor’s approach. Raise capital, buy Bitcoin, repeat. He calls Bitcoin “perfected capital.” He also terms it “economic immortality.”
Saylor envisions a colossal future. He sees Bitcoin becoming a $200 trillion settlement network. Banks, governments, and corporations would use it. Even artificial intelligence might rely on it eventually. On the other hand, some investors treat Strategy stock like a Bitcoin ETF. Others view it as a high-beta play. When Bitcoin rises, strategy often climbs faster.
Saylor personifies “hodling.” This term means holding Bitcoin tightly despite volatility. It originated from a misspelled 2013 forum post. Hodling bets on Bitcoin’s long-term value. It ignores short-term market chaos. Studies support this strategy. Loss aversion often prompts panic selling. Hodling removes that emotional trigger. Remarkably, Glassnode data confirms this behaviour. Sixty-three percent of Bitcoin hasn’t moved in over a year.
Bailey Builds a Bitcoin Media
David Bailey leads BTC Inc. and Bitcoin Magazine. He spent a decade immersed in Bitcoin culture. Now, he’s building something much larger. His goal? A Bitcoin-native conglomerate. Think media, merchant banking, and holding company combined. It mirrors historic financial dynasties. Bailey executed a bold move in April 2025. His investment vehicle, Nakamoto Holdings, merged with KindlyMD. KindlyMD is a publicly listed company. This merger provided instant public market access. The new entity raised $710 million. Most funds will convert into a Bitcoin treasury. Therefore, Bailey secures significant Bitcoin exposure.
His strategy diverges sharply from Saylor’s. Bailey embraces flexibility. He might sell Bitcoin at market highs. Proceeds could fund share buybacks or acquisitions. Reallocations are possible too. Crucially, every action aims to increase Bitcoin per share long-term. Bailey plays Bitcoin’s Rothschild, assembling influence and capital. Saylor focuses solely on accumulation.
Corporate Bitcoin Treasuries
Corporate Bitcoin adoption isn’t niche anymore. It’s a powerful trend. Holdings skyrocketed over 580% since 2020. Companies now control more than 3.6% of circulating Bitcoin. GameStop joined the movement dramatically in May 2025. It disclosed buying 4,710 bitcoins. This position was worth about $513 million then.
Trump Media & Technology Group followed closely. It announced a massive $2.5 billion capital raise. The goal? Establishing its own Bitcoin Treasury. France’s The Blockchain Group also expanded its stash. It acquired 580 bitcoins recently. Its total holdings reached 620 BTC. Following this, its stock price jumped 225%. Block, Tesla, and Coinbase remain significant holders too.
Institutional Momentum
Major players constantly acquire Bitcoin. This significantly reduces available supply. Nakamoto Holdings and Strategy lead this charge. Spot Bitcoin ETFs amplify the effect. Giants like Fidelity and BlackRock manage these funds. Now, Bitcoin increasingly looks like a strategic reserve asset. Its role in corporate finance solidifies daily.
Saylor and Bailey pioneer different institutional paths. Saylor accumulates Bitcoin relentlessly using debt. Bailey constructs a diversified financial and media empire. Both strategies drive Bitcoin deeper into traditional finance. Corporate treasuries now hold billions in Bitcoin. This adoption wave shows no signs of slowing. The race to institutionalise Bitcoin accelerates.
Written By Fazal Ul Vahab C H
