STAY HUMBLE. STACK SATS

In the summer of 2020, as the world grappled with the economic fallout of a global pandemic, an obscure software firm made a decision that would ripple through boardrooms and balance sheets for years to come. MicroStrategy, under the vision of its maverick co-founder and executive chairman Michael Saylor, decided to buy bitcoin.

And not just a little bitcoin to test the waters, but a whole bunch. Specifically, Saylor announced that his company – that up until this point had no exposure to digital assets or blockchain – had purchased 21,454 bitcoins for approximately $250 million.

This was no speculative side bet: it was a calculated pivot to position Bitcoin as the cornerstone of the company’s treasury strategy. At an average price of around $11,650 per BTC, Saylor saw not just an asset, but a bulwark against the melting ice cube of fiat currency devaluation.

Most execs paid the gambit little attention, and the few who were did derided it as a risky strategy at best and corporate suicide at worst. Saylor was betting his reputation and company’s fortune on an asset he had no control over and that was prone to high volatility. Just months earlier, BTC had plunged to under $4,000 as the COVID pandemic hit and the world grappled with the systemic shock.

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Michael Saylor wasn’t simply hedging his bets by allocating a portion of his company’s treasury to Bitcoin: he was effectively going all in on Bitcoin, and it was clear that Microstrategy would sink or swim based on BTC’s performance.

The initial buy was funded through a convertible note offering, a low-cost debt vehicle that allowed MicroStrategy to leverage its balance sheet without diluting equity immediately. This move wasn’t entirely impulsive, it should be noted; Saylor had been evangelising Bitcoin’s monetary properties since 2013, but the pandemic’s inflationary pressures crystallised his thesis.

By September 2020, MicroStrategy had amassed 38,250 BTC, and by year-end, 70,470 BTC – valued at over $1.1 billion at the time. The market’s reaction was swift: MicroStrategy’s stock surged 400% in the ensuing months, decoupling from its stagnant enterprise analytics business and trading as a de facto Bitcoin proxy.

This was a masterstroke of asymmetric risk. Saylor bet on Bitcoin's long-term appreciation outweighing short-term volatility, using debt at near-zero rates to acquire an asset with a fixed supply of 21 million coins. Critics decried it as reckless – after all, Bitcoin had crashed 80% in 2018 – but Saylor’s conviction stemmed from first principles: in a world of infinite fiat, scarcity wins. More than mere speculation, this was a philosophical rejection of central banking orthodoxy.

History has vindicated Saylor and elevated his enterprise, now simply known as Strategy, into the world’s largest publicly traded Bitcoin company. But it wasn’t all plain sailing: the years that followed the company’s first foray tested Saylor’s resolve amid Bitcoin’s infamous drawdowns, but Strategy continued doggedly stacking sats.

Saylor didn’t just buy bitcoin either: he also sold the vision, using podcasts, conferences, and social media to demystify digital assets for C-suites. In the process, he convinced other bold enterprises to drink the Kool-Aid, resulting in the normalization of DATs – Digital Asset Treasuries holding hundreds of billions of dollars of corporate funds. A growing cohort of public companies – some operators, some effectively structured as DATs – now disclose material BTC reserves.

Today, valued in the tens of billions of dollars, Strategy’s holdings eclipse the company’s core revenue streams and have been responsible for transforming it from a boring software firm into a “Bitcoin development company.” Saylor shifted the Overton window of corporate balance-sheet design, elevating Bitcoin into an institutional asset. No one’s laughing at him now.