Saylor’s Conversion

In 2013, Michael Saylor tweeted: “Bitcoin’s days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.”

Seven years later, he was the most prominent corporate Bitcoin advocate in the world.

Saylor has described his conversion in detail across hundreds of hours of interviews. The turning point was the pandemic — specifically, watching the Federal Reserve commit to unlimited money printing in March 2020. He started doing the math on what that meant for MicroStrategy’s cash holdings.

He read the Bitcoin whitepaper. He read it again. He spent weeks going through the technical and economic arguments. He reached out to Bitcoin developers, economists, and long-term holders. He emerged with a conviction that he described as bordering on certainty: Bitcoin was the best monetary technology ever invented, and holding dollars was a guaranteed slow loss.

His willingness to share that reasoning publicly — in long-form interviews, in technical discussions, in conversations with skeptics — created an enormous body of accessible Bitcoin education. He didn’t just buy Bitcoin. He explained, at length, exactly why.

Love or loathe his conclusions, Saylor’s 180-degree turn is instructive. He was not a naive enthusiast. He was a successful CEO with a Harvard engineering degree who had spent decades building a real business. His conversion came from rigorous analysis, not FOMO.

The people most qualified to dismiss Bitcoin — those who understand both the technology and the monetary system deeply — keep arriving at the same conclusion.

Tomorrow: Tesla buys Bitcoin — and then sells it.

— The Daily Bit