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Former Microsoft CEO Steve Ballmer at Town Hall Seattle during GeekWire’s Microsoft@50 special event on March 20, 2025. (GeekWire Photo / Kevin Lisota)
On this special episode of the GeekWire Podcast — part of our Microsoft@50 series — former Microsoft CEO Steve Ballmer reflects on his remarkable tenure at the company he helped shape for nearly 34 years.
Ballmer talks about his early days working alongside Bill Gates and Paul Allen — describing Gates as “the smartest guy I’ve ever known,” and crediting Allen for his instrumental role in building the company.
“Without Paul’s genius, without Paul’s push, without Paul’s insight, there’s no Microsoft. Just not a chance,” he says.
He identifies his most consequential decision as Microsoft CEO, shares his thoughts on the biggest mistake during his tenure, and offers his perspective on the company today as its largest individual shareholder.
“Cultures don’t change totally. And the notion of being hardcore and pushing forward and driving — I know that’s part of Microsoft,” he said. “Do I love the company? Do I even know the company? And the answer is, only sort of. But I love what the company does.”
He also opens up about his post-Microsoft pursuits — from his data-driven mission with USAFacts to transforming the NBA fan experience with the L.A. Clippers.
And we hear his emotional message to his former Microsoft colleagues, including many key figures in attendance for the conversation at GeekWire’s Microsoft@50 event at Town Hall Seattle last week.
“I just have such wonderful memories. And there were good times, bad times, tough things, easy things,” he said. “But it’s a reminder to me of just how cool it was to work together, and I thank you for that.”
Listen above, and continue reading for highlights.
On the tensions that came with his transition to CEO: “I knew how to work for Bill … but Bill didn’t know how for me to be his boss, or for Bill to work for me. And it took us a while, really, to get that down.”
Competing with open-source software: “There’s not a lot of businesses that have to compete with free things. We survived.”
The most impactful decision of his tenure: “It’s got to be the move to the cloud … Without that building block, it just doesn’t happen.” (This set the stage for Microsoft Azure, Office 365, and the company’s AI infrastructure.)
Former Microsoft CEO Steve Ballmer with GeekWire co-founder Todd Bishop at Town Hall Seattle. (GeekWire Photo / Kevin Lisota)
His biggest mistake: “I would have stopped the project that was Cairo (which became Windows Vista) three or four years earlier. … We had basically a team of thousands tied up for eight years to put together a release that wasn’t as good as the one that preceded it. It doesn’t sound very good.”
The failed attempt to acquire Yahoo during his tenure: “If we bought it, we would have made a lot of money, and if we didn’t buy it, we saved a lot of money.”
Microsoft’s current capital expenditures: “If they need $80 billion, they should spend $80 billion. I don’t care. I’m a long term shareholder. … I’m about the only shareholder who tells them, Hey, why aren’t you spending more?”
His philosophy as an investor: “Most portfolios should probably have three things in it. Number one is something that’s completely safe… Secondly, if there’s something you really care about and you really think you know, sure, invest in it. … And then you can have something that you’re kind of screwing around with.”
Former Microsoft CEO Steve Ballmer still has his trademark energy. (GeekWire Photo / Kevin Lisota)
Working on the Intuit Dome for the L.A. Clippers: “I knew more about what I wanted in that arena than in any other product I was ever involved with.”
The importance of transparency in government data: “Numbers are the least partisan thing you can have, in the sense that adjectives can make things sound big and small — they can get partisan. Numbers are just what they are.”
On Microsoft finding its way in AI under Satya Nadella: “Somebody asked me, why weren’t you guys the first guys to do LLMs?… But guess what — they pivoted. They got it right. … You just have to give Satya all the credit in the world.”
Listen to the conversation above, or subscribe to GeekWire in Apple Podcasts, Spotify, or wherever you listen.
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