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Saylor to step down as MicroStrategy CEO after 33 years

The vendor's co-founder will leave the role he's held since the company was founded to become executive chairman, with President Phong Le to take over as CEO.

After 33 years, Michael Saylor is stepping down from his role as CEO of MicroStrategy.

On Aug. 8, Saylor, who co-founded MicroStrategy in 1989 with Sanju Bansal, will assume the new role of executive chairman and continue to serve as chairman of the board of directors. Phong Le, who joined MicroStrategy in 2015 and has been the analytics vendor's president since July 2020, will succeed Saylor as CEO.

MicroStrategy, based in Tysons Corner, Va., has been a substantial investor in Bitcoin since making its first purchase of the cryptocurrency in August 2020.

Since then, the vendor has made an additional 20 purchases and now has acquired 129,699 bitcoin for nearly $4 billion.

In his new role as executive chairman, Saylor will continue to oversee MicroStrategy's Bitcoin acquisition strategy, while also focusing on product innovation and long-term corporate strategy, according to a release.

As president and CEO, Le will oversee the execution of the vendor's corporate strategies on a day-to-day basis and manage all business operations.

3 decades of leadership

While the move marks the first CEO change in MicroStrategy's lengthy history, it's not necessarily a surprise, according to Wayne Eckerson, founder and principal consultant at Eckerson Group.

Thirty-three years is a long time. So, I think that warrants a change of venues for Saylor. And … Phong Le has been very successful in operating the software business.
Wayne EckersonFounder and principal consultant, Eckerson Group

"Thirty-three years is a long time. So, I think that warrants a change of venues for Saylor," he said. "And … Phong Le has been very successful in operating the software business."

Likewise, Boris Evelson, analyst at Forrester Research, said MicroStrategy will be in good hands with Le as its new CEO.

He noted that, as more enterprise data migrates to public clouds like AWS, Google Cloud and Microsoft Azure, independent analytics vendors could face new challenges but added that Saylor and Le have levels of expertise that should enable MicroStrategy to remain competitive and continue to grow despite the changing climate.

"Forrester has worked for many years with both Michael and Phong, and we are confident that between the two of them -- regardless of the new roles -- they have the right expertise and experience to continue to improve MicroStrategy's position in the market," Evelson said.

Michael SaylorMichael Saylor

The news that Saylor is moving on from his position as CEO of MicroStrategy with Le assuming the role came on the same day the vendor reported its second quarter 2022 earnings.

Revenue of $122 million was down slightly from $125 million during the second quarter of 2021, and revenue of $241 million through the first six months of 2022 is similar to $248 million through the first half of 2021.

The vendor's Bitcoin holdings, meanwhile, have lost nearly half of their value, totaling $1.99 billion, with $917 million of that coming during the second quarter of this year.

Saylor still involved

Despite the essentially flat revenue growth and significant Bitcoin losses, Eckerson said there's no reason to believe Saylor is leaving his role as CEO due to external pressure.

Saylor owns about one-quarter of the company's shares, and through the years, he has made major investments on MicroStrategy's behalf that have both succeeded and failed. In addition, he will remain in a leadership position despite no longer being the CEO of MicroStrategy.

"Michael is a forward-thinking business technologist who isn't afraid to venture into a new or adjacent area before there is obvious market demand," Eckerson said. "Some of his bets paid off handsomely, like betting on [relational online analytical processing] but also mobile BI and web BI. Some didn't pan out."

MicroStrategy, meanwhile, is a reflection of Saylor, and given his stock ownership and continued leadership roles, that is unlikely to change, Eckerson continued.

"Michael is one of the most intelligent, knowledgeable and bullish people I've ever met," he said. "He has great vision for how markets will unfold and is unafraid to introduce [or] chase new technologies and opportunities. Always his own man and boss, he's kept an iron grip on his company and stock, maintaining … control in spite of criticism."

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