In 2020, the world shut down. Michael Saylor opened his mind. What followed was one of the boldest corporate bets in financial history. As governments printed trillions, and cash lost meaning, Saylor turned to Bitcoin—and rewrote the rules of treasury management. His move was radical, but his logic was brutally clear.
Confident Investing Starts Here:
- Easily unpack a company's performance with TipRanks' new KPI Data for smart investment decisions
- Receive undervalued, market resilient stocks right to your inbox with TipRanks' Smart Value Newsletter
Watching Cash Rot Drove Saylor to Hard Assets
In an interview with Jordan B. Peterson that aired on Monday, Saylor described the COVID lockdowns as a “war on currency,” not just on health. With $500 million in Strategy’s (MSTR) reserves earning nothing, he faced a simple but devastating choice: let inflation bleed it dry—or act. He chose Bitcoin, explaining, “I had an asset that was now non-performing […] so I have a choice between a fast death or a slow death.”
It was never about gambling on crypto. It was about protecting economic energy.
The System Was Broken, Bitcoin Was a Lifeboat
While Main Street was shut down, Wall Street boomed. Markets rebounded shockingly fast, not from growth—but from printed money. “COVID lockdown takes place and there is a massive panic,” Saylor said. But what disturbed him most was the market recovery “by the summer of 2020” fueled not by fundamentals but by stimulus.
This divergence told him one thing: the rules had changed. And cash would no longer be king.
Bitcoin Wasn’t a ‘Scam Coin’
Saylor admitted he initially thought Bitcoin was a joke. But with nowhere else to go—no undervalued real estate, no safe bonds, no accessible fine art—he began asking better questions. He turned to podcasts, books, and conversations. He wanted a liquid, portable, non-sovereign store of value.
That led him to Bitcoin.
Strategy’s $250M Bet Changed Corporate Finance Forever
In August 2020, Strategy bought 21,454 BTC for $250 million. That wasn’t a moonshot. It was a lifeboat purchase. Since then, the company has grown its position to 582,000 BTC—worth over $63 billion. And while markets debate the future of crypto, Saylor’s actions have permanently changed how corporations think about balance sheet risk.
He wasn’t chasing hype. He was dodging slow death.
It was about timing history. In a world of manipulated interest rates and vanishing yields, he chose something that couldn’t be printed. That mindset (looking for asymmetric bets when the world panics) is what turned a conservative CEO into a digital asset legend.
Is MicroStrategy a Buy Right Now?
MicroStrategy, now rebranded as Strategy, has drawn strong support from Wall Street analysts. According to TipRanks, the stock holds a Strong Buy rating. 12 out of 13 analysts currently call it a Buy, with just one lone Sell and zero Hold ratings. The average 12-month MSTR price target sits at $524.92—implying a 35.6% upside from the recent close.


Looking for a trading platform? Check out TipRanks' Best Online Brokers guide, and find the ideal broker for your trades.
Report an Issue