Here's a fun bit of financial history: Strategy Inc. (MSTR) co-founder Michael Saylor is now one of the most vocal Bitcoin evangelists on Wall Street. But rewind about 12 years, and you'd have easily mistaken him for one of crypto's harshest critics.

When Saylor Sounded Like a Bitcoin Skeptic

On December 19, 2013, Saylor posted something to Twitter (now X) that sounds like it came straight from the crypto-skeptic playbook: "Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling."

The comparison to gambling wasn't unique. Warren Buffett, the Oracle of Omaha himself, called Bitcoin (BTC) a "gambling token" with no intrinsic value in April 2023. Economist Nouriel Roubini, better known as "Dr. Doom," went even further in a 2019 op-ed, comparing cryptocurrency investing to gambling at an "unregulated casino."

So back in 2013, Saylor's take wasn't particularly original. He was just another voice in the chorus of Bitcoin doubters.

The Complete 180-Degree Turn

Then something changed. Actually, everything changed. Less than seven years after that fateful tweet, Saylor's company made Bitcoin its primary reserve asset, becoming the first publicly listed company to pursue this strategy.

Fast forward to today, and Strategy is the world's largest corporate owner of Bitcoin. According to bitcointreasuries.net, the company's stash is worth more than $59 billion. That's not a typo.

These days, Saylor rarely goes a day without promoting Bitcoin in public addresses or on social media. His commitment is so intense that he once joked, "Sell a kidney if you must but keep the Bitcoin." (Please don't actually do that.)

Owning the Mistake

When someone recently reminded Saylor of his 2013 doomsday prediction, he didn't try to deflect or explain it away. He simply acknowledged it as a "₿ig Mistake," complete with the Bitcoin symbol replacing the B.

It's a remarkable transformation from skeptic to true believer, one that's backed by billions of dollars in corporate treasury decisions.

Where Things Stand Now

At the time of writing, Bitcoin (BTC) was trading at $88,912.01, up 1.46% in the last 24 hours.

Strategy shares closed 0.53% higher at $158.71 on Wednesday. However, year-to-date, the stock has plunged 45.20%. The stock currently exhibits a very low Momentum score, which measures relative strength based on price movement patterns and volatility across multiple timeframes.

Whether Saylor's dramatic conversion proves prescient or becomes another cautionary tale remains to be seen. But one thing's certain: when it comes to changing your mind about Bitcoin, he's gone all in.