From Skeptic to Bitcoin Believer (2013–2020): 

Michael Saylor, co-founder of MicroStrategy, wasn’t always a Bitcoin believer. In fact, back in December 2013 he famously tweeted that Bitcoin’s days were numbered, likening it to a passing fad. He largely forgot about that tweet until seven years later, when circumstances prompted a drastic change of heart. By 2020, with global money-printing in overdrive and interest rates near zero, Saylor began to worry that MicroStrategy’s $500 million cash reserve was a “melting ice cube” losing value to inflation. Seeing fiat currency debased, he started to view Bitcoin as a solution – a digital gold that could preserve value. That year, Saylor declared that Bitcoin was actually less risky than holding cash or gold, signaling a complete 180° in his perspective. This pivotal shift set the stage for one of the boldest corporate investment strategies ever seen.

Embracing Bitcoin as a Treasury Reserve (2020): 

In August 2020, Saylor made headlines when MicroStrategy purchased 21,454 BTC (around $250 million worth) as its primary treasury reserve asset. It was a radical departure for a business intelligence software firm, but Saylor was convinced it was a prudent move to protect shareholder value amid currency inflation. He didn’t stop there. By mid-September 2020, MicroStrategy had upped its holdings to 38,250 BTC, and the company signaled plans to keep allocating excess cash into Bitcoin. Saylor’s bold bet quickly paid early dividends: MicroStrategy’s stock (MSTR) surged as investors began to treat it as a proxy for Bitcoin’s price movements. What began as a one-off hedge had evolved into a core business strategy – Bitcoin became the centerpiece of MicroStrategy’s balance sheet.

Relentless Accumulation to 600,000 BTC: 

Once Saylor was convinced of Bitcoin’s long-term value, MicroStrategy embarked on an accumulation spree over the next several years. By the end of 2021, the company held well over 120,000 BTC, and Saylor continued to buy during market dips and rallies alike. MicroStrategy even issued convertible notes and new equity to raise capital for more Bitcoin purchases. Despite some market volatility (and even a rare small sale in 2022 for tax purposes), Saylor’s conviction never wavered. The result: MicroStrategy’s holdings grew methodically through 2022–2023 and then accelerated dramatically in 2024 as Bitcoin’s price began rising again. In late 2024 and the first half of 2025, Saylor doubled down – raising capital and buying tens of thousands of BTC in steady weekly chunks. By June 2025, MicroStrategy’s stash had swelled to about 582,000 BTC. Just a month later, after a few additional large purchases, MicroStrategy blew past the historic 600,000 BTC milestone in July 2025. This astonishing cache made MicroStrategy by far the largest corporate holder of Bitcoin, cementing Saylor’s reputation for unflinching Bitcoin maximalism.

By the Numbers – A $42 Billion Bet Paying Off: 

The scale of Saylor’s Bitcoin bet is almost difficult to fathom. As of mid-2025, MicroStrategy holds approximately 601,550 BTC acquired at a total cost basis of about $42.87 billion. The company’s average purchase price stands around $71,000 per coin. With Bitcoin hitting new all-time highs in 2025, the market value of this hoard has climbed to roughly $71–72 billion, yielding an unrealised gain north of $28.5 billion (about +66% over cost). In simpler terms, Saylor’s high-conviction bet appears vindicated – the Bitcoin strategy has added tremendous paper profits. Investors have noticed: MicroStrategy’s stock price has skyrocketed in tandem with its Bitcoin holdings. By July 2025, the company’s market capitalisation surged to over $118 billion (a more than hundredfold increase from its pre-Bitcoin days), and MSTR shares were up over 3,300% since the first BTC purchase in 2020. MicroStrategy even earned a spot in the Nasdaq-100 index by late 2024 as its valuation ballooned. Essentially, Wall Street began valuing MicroStrategy primarily as a Bitcoin holding company, and Saylor’s audacious strategy turned his midsize firm into a de facto Bitcoin ETF.

Sparking a Corporate Bitcoin Movement: 

Beyond the numbers, Michael Saylor’s advocacy has had a ripple effect on the broader corporate world. In late 2020, Saylor publicly urged other CEOs to consider Bitcoin, even tweeting at Tesla’s Elon Musk about converting Tesla’s balance sheet. His evangelism bore fruit: in early 2021, Tesla bought $1.5 billion of Bitcoin (ultimately accumulating 11,000+ BTC) after Saylor’s encouragement. Saylor also hosted online seminars (the “Bitcoin for Corporations” series) to share his playbook with other firms. A number of companies followed MicroStrategy’s example on a smaller scale – from fintech firm Square (now Block) putting Bitcoin in its treasury, to lesser-known firms like MetaPlanet and Semler Scientific using corporate funds to buy BTC. Saylor’s bold example legitimised Bitcoin as a treasury asset in boardrooms, helping transform the narrative of Bitcoin from a speculative toy to a strategic reserve asset. Even institutional investors who wouldn’t hold crypto directly found ways to gain exposure – for instance, investment giant Vanguard (once a Bitcoin skeptic itself) became one of MicroStrategy’s largest shareholders, indirectly riding the Bitcoin wave. Saylor’s outspoken persona – from proclaiming Bitcoin “the apex property of the human race” to quipping that one should “sell a kidney, keep the Bitcoin” – further amplified his message. Love him or hate him, he has undeniably become a leading ambassador for corporate Bitcoin adoption.

Conclusion – Legacy of a Bitcoin Visionary: 

In just five years, Michael Saylor went from dismissing Bitcoin to architecting one of the most consequential bets in corporate finance history. Under his leadership, MicroStrategy transformed into a Bitcoin powerhouse, proving that a determined company can hodl hundreds of thousands of bitcoins. The move has dramatically boosted MicroStrategy’s fortunes, and it paved the way (and set a blueprint) for other corporations contemplating Bitcoin as part of their strategy. Saylor’s journey underscores a broader point: conviction and vision, backed by strategic execution, can redefine a company’s future – and perhaps even kickstart a paradigm shift in how businesses think about money and reserves. From skeptic to true believer, Michael Saylor has not only altered his own company’s trajectory but also left an indelible mark on the story of Bitcoin’s mainstream adoption.