Steve Ballmer nearly dumped his Microsoft stock after leaving — here’s why he decided to hold on

Former Microsoft CEO Steve Ballmer came close to selling his entire stake in the company around 2015 or 2016, after his departure, before two people on his team made the case to keep his stock.

In hindsight, dumping his shares might have cost him tens of billions of dollars over the long run. But he seriously considered selling, out of a desire to emotionally detach from the company after he left Microsoft in 2014, Ballmer says in a new interview on the Acquired podcast. 

“I went to one shareholder meeting, and I was kind of a dick, in my opinion,” he said, alluding to a 2015 meeting where Bloomberg News reported on his running commentary criticizing Microsoft’s cloud disclosures and mobile strategy.

“I was too emotionally attached,” Ballmer told Acquired hosts Ben Gilbert and David Rosenthal. “Took me about a year to say, I just have to emotionally detach.”

But two members of his Ballmer Group philanthropy, both former Microsoft employees, helped to convince him to keep his stock, given its potential to increase in value.

“You can’t sell. This is going to be worth a lot more,” he recalled one of them saying.

Ultimately, he opted not to worry about the upside or downside. 

“I’m just going to be loyal,” he decided.

It was a wise decision, financially. Microsoft’s stock soared over the following decade. Today, Ballmer is the company’s largest individual shareholder, with his stake in Microsoft making up the bulk of his estimated $130 billion net worth. 

Ballmer remembered an event where Charlie Munger, the late longtime business partner of Warren Buffett, commented about his decision to hold his Microsoft shares while co-founders Bill Gates and Paul Allen had sold big portions of theirs.

“I know you’re not that smart,” Munger told Ballmer.

Ballmer’s response: “No, Charlie, but I’m loyal.”

The nearly three-hour episode of the hit podcast — a follow-up to Acquired‘s two–part Microsoft series last year — covers topics such as Ballmer’s missteps in mobile and search, his regrets about losing Microsoft’s “consumer muscle,” and his strategic disagreements with the board and Gates that ultimately contributed to his decision to leave the company.

But the episode also details Ballmer’s role in establishing the company’s enterprise business, and fueling its move into the cloud — which, in turn, combined with the Bing search engine to provide the foundation for Microsoft’s current push into artificial intelligence.

Watch the full episode via YouTube or Acquired.fm.