Michael Saylor

1965 · 1987: Air Force kid, MIT engineer. Born 4 February 1965 in Lincoln, Nebraska, grew up on US Air Force bases, studied at MIT on an Air Force ROTC scholarship (aeronautics and the history of science).

1989: Founds MicroStrategy. Co-founds MicroStrategy with MIT fraternity brother Sanju Bansal: business-intelligence software. IPO on Nasdaq in June 1998 at $12 a share.

20 Mar 2000: The dot-com crash, in one day. MicroStrategy restates two years of results; the stock, which had climbed as high as $333, falls 62% in a single day to about $120, one of the moments that marked the end of the dot-com bubble. Saylor's net worth drops by about $6 billion. In December 2000 he settles with the SEC without admitting wrongdoing ($350,000 penalty, $8.3 million disgorgement).

Dec 2013: “Bitcoin days are numbered”. The skeptic years: he tweets that Bitcoin will share the fate of online gambling. The post is still up and became his most-quoted mistake.

Aug 2020: The Bitcoin pivot. On 11 August 2020 MicroStrategy adopts bitcoin as its primary treasury reserve asset, after buying 21,454 BTC for $250 million. More buys follow, then convertible bonds and new shares sold to buy more.

2022 · 2025: Executive chairman, then “Strategy”. In August 2022 he hands the CEO job to Phong Le and becomes executive chairman to focus on the bitcoin strategy. On 5 February 2025 MicroStrategy starts doing business as Strategy, with an orange ₿ logo.

2026: The first sales. In June–August 2026 Strategy reports net bitcoin sales for the first time (32 BTC in late May to fund preferred-stock dividends, then larger amounts), before returning to net buying from late August. Saylor says he personally has never sold.

“#Bitcoin is a swarm of cyber hornets serving the goddess of wisdom, feeding on the fire of truth, exponentially growing ever smarter, faster, and stronger behind a wall of encrypted energy.” (2020-09-18)

“There is no second best. #Bitcoin” (2021-10-08)

“21st century investors lost trillions clinging to 20th century ideas. #Gold peaked in the 19th century. Buy #Bitcoin.” (2020-10-05)

“#Bitcoin is Digital Property.” (2022-01-05)

“Sell a kidney if you must, but keep the Bitcoin.” (2025-02-28)

“#Bitcoin days are numbered. It seems like just a matter of time before it suffers the same fate as online gambling.” (2013-12-19)

“Don’t wait to buy #bitcoin, buy #bitcoin and wait.” (2021-07-18)

“#Bitcoin is hope.” (2021-06-01)

Laser eyes (#LaserRayUntil100K, 2021): When the laser-eyes trend took over Bitcoin Twitter in February 2021, Saylor became its most famous face. On 1 April 2021 he wrote “If you don't understand laser eyes, then you don't understand #Bitcoin.”, and on 10 May 2021 he posted a laser-eyed profile picture with a three-sentence manifesto (“Laser eyes proclaim a technology to guarantee the human rights of life, liberty, & property…”). The deal was to keep the lasers until bitcoin hit $100,000, which happened on 5 December 2024.

“#Bitcoin is hope” (#Bitcoin is hope, 2021): Three words first posted on 1 June 2021 that became his closing line for years, with endless variations: hope for Argentina, for Turkey, for Japan, even “hope for Berkshire Hathaway”. In June 2026 he still listed it among his beliefs: “Bitcoin is hope and economic empowerment for everyone.”

The Sunday tracker post (Sunday ● ● ●, 2024–2026): Almost every Sunday Saylor posts the chart of Strategy's purchases (orange dots, one per buy) with a cryptic caption. For a long time a Sunday chart meant a Monday filing with a new purchase, so traders watch it like a weather forecast. In 2026 the link weakened: a July post (“We're gonna need another color”) came after four weeks without a buy. Today's caption, 11 October 2026: “There’s always room for more orange.” Whether Monday brings a buy is only known from the company's filing.

“I'm buying more” (buying the top forever, 2022–2026): Fans sum up his approach as “I'm buying more”. We did not find a post with exactly those words, so here are the real ones: “I'm going to be buying the top forever.” (3 July 2025) and “Thinking about buying more bitcoin.” (22 January 2026, 1.6 million views).

“Saylor never sells” (Never sell your Bitcoin, 2020–2026): The meme is half true. Saylor posts “Never sell your Bitcoin.” and says he personally has never sold a satoshi. His company is different: MicroStrategy sold 704 BTC in December 2022 for a tax loss (and bought back more), and in June–August 2026 Strategy reported its first net sales, the largest, 2,225 BTC, reported on 6 July. On 1 August 2026 Saylor wrote: “We have never had a ‘never sell’ policy.” Since late August Strategy is a net buyer again.