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Jack Dorsey is trying to avoid making a Bill Gates mistake

November 30, 2021, 6:27 PM UTC

Jack Dorsey stepped down as CEO of Twitter Monday morning, paving the way for his successor and former CTO Parag Agrawal to take over. On his way out, Dorsey emphasized the importance of his full removal from company leadership.  

“Why not stay or become chair?” Dorsey wrote in an email he sent to the company, and later tweeted. “I believe it’s really important to give Parag the space he needs to lead…I believe it’s critical a company can stand on its own, free of its founder’s influence or direction.”

Dorsey said he will serve on Twitter’s board until spring to help with the transition, and then leave the board entirely. And his decision to leave the company cold turkey is in stark contrast to another famous founder: Bill Gates. 

After dropping out of Harvard to found Microsoft in 1975, Gates was heavily involved in every aspect of his business—from developing the first computer operating system that became known as Microsoft, to taking the company public. Gates stepped down as CEO in 2000. 

Enter Steve Ballmer. Gates brought on his Harvard classmate as Microsoft’s 30th employee in 1980, and Ballmer steadily rose in rank from a manager to company president by the late 1990s. When Ballmer was chosen as the new CEO, Gates decided to stay on as chairman and “chief software architect.” And while the pair had developed a close friendship over the past 33 years of working together, Gates’ constant presence within the company created an infamous strain on their relationship and a difficult working environment for Ballmer. 

“Bill and I had to go through a rough patch to figure out what it really meant that he had asked me to become CEO, but he wanted to stay around sort of working for me as ‘chief software architect.’ We got through what I’ve called the bumpiest period in about a year and a half, two years, but it was bumpy,” Ballmer told Business Insider in 2017. “I don’t think I felt really like CEO in full until Bill chose to leave the company in a full-time sense in 2008.”

The two butted heads frequently about the direction of the company. Ballmer says he wanted to focus on hardware, while Gates kept pushing him to invest in tablets and smartphones. When Microsoft finally acquired Nokia’s phone business in 2013, the company wrote down $8.4 billion a couple of years later, its largest-ever quarterly net loss, which analysts mostly attributed to the Nokia purchase. Gates has publicly stated that not involving Microsoft in the smartphone industry sooner is one of his “greatest mistakes.”  

Ballmer officially retired as CEO and from Microsoft in 2014, and he said in an interview that he and Gates have since “drifted apart.” 

In March 2020, Gates officially stepped down from Microsoft’s board and now has no formal role there, but he said that the decision “in no way means stepping away from the company.”

This week, Dorsey has made it clear that not only is he choosing to step away from Twitter, but he also believes it’s the move the company needs to thrive, and also for Agrawal to succeed.

“He leads with heart and soul, and is someone I learn from daily,” Dorsey said of his successor. “My trust in him as CEO is bone deep.”

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