The character arc of Michael Saylor
A life drawn by Character Arc from the public record
Born on 4 February 1965 in Lincoln, Nebraska, on Air Force bases around the world. Between then and now sit MIT on a scholarship in 1983, DuPont in 1988, a McDonald's contract in 1992, an entrepreneur of the year award in 1996, the MicroStrategy listing in June 1998, the restatement of 20 March 2000, the Saylor Foundation in 1999, The Mobile Wave in 2012 and the move to executive chairman in August 2022. The line below draws the story so far, in order.
Tap the line to pluck it. Hover or tap any mark for its card. Drawn from the public record of his life; the sources are at the foot of the page.
Who is Michael Saylor?
He lost most of it in a day.
He was born in Lincoln, Nebraska in 1965 and spent his early years on Air Force bases around the world, his father an Air Force chief master sergeant. In 1983 he went to the Massachusetts Institute of Technology on an Air Force Reserve Officers Training Corps full scholarship, and in 1988 became an internal consultant at DuPont, building computer models to help the company anticipate change in its markets. The models predicted a recession in many of those markets in 1990.
Out of that came MicroStrategy. In 1992 it won a ten million dollar contract with McDonald's to analyse the efficiency of its promotions. He was named a KPMG entrepreneur of the year in 1996 and an Ernst and Young software entrepreneur of the year in 1997, and he took the company public in June 1998 with an offering of four million shares at twelve dollars each. By early 2000 his own net worth had reached seven billion dollars.
On 20 March 2000 MicroStrategy announced it would restate its financial results for the previous two years. Class action suits followed, and the fortune went with them. He did not leave. He was still running the company more than twenty years later, published The Mobile Wave in June 2012, which reached the New York Times bestseller list, announced in July 2020 that the company would look at holding bitcoin instead of cash, and became executive chairman on 8 August 2022. The company was renamed Strategy in February 2025. He founded the Saylor Foundation in 1999, whose free education initiative launched as Saylor.org in 2008.
The moments
Michael Saylor's timeline.
The 1980s
MIT, on a scholarship
Milestone, and it changed his direction. A full scholarship, from a childhood spent on Air Force bases.
Computer simulation modelling
Milestone. Simulation, which turns out to be the whole of the next company.
A consultant at DuPont
Milestone, and it changed his direction. Models that called a recession before it arrived.
The 1990s
The McDonald's contract
Milestone, and it changed everything. Ten million dollars, from a company that sells hamburgers.
Entrepreneur of the year
Milestone. Two awards in two years, before the company was public.
MicroStrategy goes public
Milestone, and it changed everything. Four million shares at twelve dollars, and by early 2000 he was worth seven billion.
The Saylor Foundation
Milestone, and it changed his direction. Free courses, set up the year before everything went wrong.
The 2000s
The restatement
Setback, and it changed everything. One announcement, and most of seven billion dollars was gone.
Stay, after the restatement
Crossroads, decided.
The paths laid out: stay and rebuild, taken, or step away. He was still leading the company in July 2020 and became its executive chairman on 8 August 2022.
The 2010s
The Mobile Wave
Milestone, and it changed his direction. A bestseller, twelve years after the worst day.
The 2020s
A different balance sheet
Milestone, and it changed everything. A software company deciding to hold something other than dollars.
Executive chairman
Milestone, and it changed his direction. Thirty years after the McDonald's contract, he handed over the chair.
MicroStrategy becomes Strategy
Milestone. A new name, on a company he had run since before the internet was a business.
The line reaches today still adding to itself, which is why it is drawn now rather than at the end. What it has set moving is the part most lines leave out: the worst day is on the chart, in the middle, with twenty six more years drawn after it.
What he wrote
Books by Michael Saylor
- 2012
The Mobile Wave
How mobile intelligence will change everything, published by Perseus Books. It reached seventh on the New York Times hardcover non-fiction list in August 2012, twelve years after the worst day of his career.
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Sources
- Michael J. Saylor, English Wikipedia biography, filed under living people.
- MicroStrategy announcement of 20 March 2000 and the class action filings in the Eastern District of Virginia.
- New York Times bestseller list, hardcover non-fiction, August 2012.