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The Steve Ballmer Interview

June 1, 2025

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5 min read

The Steve Ballmer Interview

Steve Ballmer walked into the interview with a PowerPoint deck he'd prepared the night before. He sent it at 10 PM. "I figured, eh, I'll send them to you," he said. "And they're PowerPoint." This is the man who, since leaving Microsoft as CEO in 2014, has seen his net worth grow from $20 billion to $130 billion—almost entirely by doing nothing except holding his Microsoft stock. He is arguably the best investor of the last 20 years, and he did it by not selling.

The IBM Relationship and the Birth of Microsoft's Enterprise Business

When Ballmer joined Microsoft in 1980, IBM was "the sun, the moon, and the stars." The computing world had IBM and "the bunch"—Burroughs, Univac, NCR, Control Data, and Honeywell. IBM did everything: mainframes, software, services. When IBM approached Microsoft about building a PC, they wanted an operating system. Microsoft didn't have one. They licensed a CP/M clone from a Seattle company called Seattle Computer Products for about $45,000, then sold it to IBM. The key structural detail: Microsoft negotiated a non-exclusive deal. IBM, experimenting with industry-standard parts instead of building everything custom, accepted this. The BIOS—the lowest layer of firmware—was IBM's proprietary protection. But the clone market eventually cracked that too.

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What you'll learn

  • 1 (00:58) **Steve Ballmer: The Best Investor of the Last 20 Years** - Ben and David frame Ballmer's staggering net worth growth from $20B to $130B since leaving Microsoft, all from holding his stock.
  • 2 (03:44) **The Enterprise Muscle vs. Consumer Muscle** - Ballmer reflects on building Microsoft's enterprise business and his regret over losing the consumer muscle.
  • 3 (07:30) **Riding the Bear: Microsoft's Relationship with IBM** - The story of IBM's dominance in the 1980s and the deal that launched Microsoft.
  • 4 (21:00) **The OS/2 Divorce and the Birth of the Enterprise** - IBM kicks Microsoft out of their joint OS/2 project, forcing Microsoft to go all-in on Windows and the enterprise.
  • 5 (29:02) **The Enterprise Agreement and the "Holy Trinity"** - Ballmer explains the invention of the enterprise agreement and the integrated suite that became Microsoft's enterprise moat.
  • 6 (49:10) **"Developers, Developers, Developers" and the Platform Trap** - Ballmer sets the context for his iconic speech and warns against the "we're just a platform company" mindset.
  • 7 (61:45) **The Windows Everywhere Trap and the Miss on Mobile** - Ballmer diagnoses why Microsoft failed in mobile and search: trying to extend Windows into places it didn't belong.

+ Full timestamped outline available in the app

Guests on this episode

Steve Ballmer

Show Notes

We sit down with Steve Ballmer, the legendary former Microsoft CEO and owner of the LA Clippers, for an epic conversation covering his 34 years at Microsoft. Steve listened to our Microsoft episodes and had some thoughts to share — and boy, did he deliver. Steve takes us point-by-point through the original IBM DOS deal that started everything, how he built Microsoft's enterprise business from scratch, and offers his candid reflections on missing mobile and search. We also cover the story behind “developers, developers, developers”, the complexities of his relationship with Bill Gates (including a year where they didn't speak), and why he ultimately decided to step down as CEO. Plus, we learn why Steve has held onto his Microsoft stock through it all — giving him arguably the best investment track record in the world over the last 10 years with his net worth growing from $20B to $130B since leaving. And of course, we couldn't resist also talking about his other passion: the Clippers and Intuit Dome. Hit play and get ready to experience the patented Steve Ballmer energy and fun on full display!

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‍Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.

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