In August 2020, Michael Saylor transformed from a technology executive into a symbol of corporate crypto adoption.
Saylor, long known as the co-founder and head of enterprise-software firm Strategy (previously MicroStrategy), made his first bold move into cryptocurrencies by allocating $250 million of the company’s cash to purchase Bitcoin
BTC$115,140.
He cited a weakening dollar and long-term inflation risks as the underlying reasons behind this strategic move. Incidentally, it marked the largest acquisition of Bitcoin by a publicly traded company at that time and set a new precedent.
Within months, Strategy expanded its holdings: $175 million more in September, $50 million in December and a $650-million convertible-note issuance, bringing Bitcoin holdings over $1 billion.
He recognized Bitcoin as “capital preservation,” comparing it to “Manhattan in cyberspace,” a scarce, indestructible asset.
The move drew both praise and criticism. Skeptics called it reckless, while supporters saw it as a bold innovation at a time when few dared to put Bitcoin on a company’s balance sheet. For Saylor, though, it wasn’t a gamble. It was a calculated hedge against monetary uncertainty and a signal that digital assets would reshape capital strategy.
Did you know? In 2013, Saylor tweeted that Bitcoin’s days were numbered, predicting it would “go the way of online gambling.” That post resurfaced in 2020, right as he pivoted Strategy into the biggest Bitcoin holder among public companies. He has since referred to it as the “most costly tweet in history.”
From that initial entry point, Saylor doubled and tripled down on his belief in Bitcoin. He applied structured finance tools to scale holdings and shape Strategy into a “Bitcoin treasury company.”
It all started during the July 2020 earnings calls when Saylor announced his plan to explore alternative assets, such as Bitcoin and gold, instead of holding cash. He put the plan into motion with quarterly Bitcoin buys that rapidly scaled holdings to tens of thousands of coins at a favorable cost basis.
By early 2021, Saylor had borrowed over $2 billion to expand his Bitcoin position, an aggressive posture powered by conviction, not speculation. He articulated a vision of long-term ownership by saying that Strategy will hold its Bitcoin investment for at least 100 years.
Despite Bitcoin’s extreme volatility, soaring to $64,000 from $11,000 in 2021 and then plunging to near $16,000 by the end of 2022, Saylor remained unwavering. In support of the claim that Bitcoin is the apex of monetary structure, his team used dollar-cost averaging to take advantage of price dips to increase holdings.
Saylor’s strategy worked: His company’s stock surged, often outperforming Bitcoin itself. By late 2024, Strategy’s stock had gained multiples of S&P 500 returns, and the business became viewed less as a software firm and more as a leveraged crypto proxy.
Saylor’s obsession evolved from a bold entry to dominating corporate
