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For most of the past 25 years, Michael Saylor was a relatively low-profile tech executive running a boring software firm in Tysons. During the pandemic, however, his career took an unexpected turn when he made a nearly $500-million bet on a notoriously unpredictable cryptocurrency. The transformation began last March, when Saylors company, MicroStrategy, was looking for a place to park a half billion dollars in reserve funds. In August, he began buying up hundreds of millions of dollars in Bitcoin, the trendy currency that has fascinated digital risk-takers since it was introduced in 2009. Its the best money created in the history of the world, Saylor says. Then, in December, MicroStrategy went even further, announcing it was taking on $650 million in debt in order to, yes, buy more Bitcoin.

Bitcoins volatility is one of its defining features; its value plunged from $19,000 per unit in 2017 to less than $4,000 the following year. By early 2021, a Bitcoin was worth more than $40,000. Saylor sees the cryptocurrency as a great way to protect his companys money from inflation, which he thinks will skyrocket.

Will that huge bet pay off? Well have to wait on that one, because Saylor claims he wont sell his Bitcoin trove for at least 100 years. But in the meantime, Saylor has himself become something of a celebrityone of the most prominent cryptocurrency evangelists. His Twitter following has surged to more than 300,000, and he now fields interview requests from the kind of national business publications that werent terribly interested in MicroStrategy before. Of course, by prominently advocating for Bitcoin, he helps protect the value of his own investment.

Born in Nebraska and raised mostly in Ohio, Saylor is an MIT alum who moved his six-year-old company from Delaware to the Washington area in 1995, and his net worth was at one point estimated to be in the billions. Hes also had his share of controversy: In 2000, he settled with the SEC over charges of financial impropriety (without admitting guilt). More recently, he has been an opponent of some Covid safety measures.

Saylors Bitcoin gamble has so far looked prescient. Its price has exploded by a factor of seven since March 2020, and MicroStrategys stock price has surged fivefold. Even so, in December, Citigroup analysts recommended that investors start selling MicroStrategy shares, citing concerns about overvaluation as well as Saylors disproportionate focus on Bitcoin vs. running the business.

Saylor waves away such criticism. Bitcoin is a radical new thing, he says, so if you are in the old paradigm, your view would be this is just scary and risky. Plus, his crypto fame is paying off in other ways: I think probably it would cost us $100 million a year to buy the kind of publicity that we now get for free.

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Michael Saylor Explains Why He's Investing More Than $1 Billion in Bitcoin - Washingtonian