Michael Saylor’s Bitcoin obsession: How it all started

2025-09-21 13:41:23 Primitive Reading

Key takeaways:

Michael Saylor transformed MicroStrategy from a business intelligence firm into the world’s largest corporate Bitcoin holder.
Saylor’s conviction redefined corporate strategy, turning volatility into opportunity through long-term, dollar-cost averaging purchases.
His approach set the standard for institutional Bitcoin adoption despite concerns over dilution and debt.
Saylor’s playbook highlights research, perseverance, risk control and long-term thinking in Bitcoin investing.

Saylor’s Bitcoin awakening

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.”

Saylor’s Bitcoin expansion

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