Microsoft’s misunderstood era: Ben Gilbert of ‘Acquired’ on the tech giant’s most pivotal years

Microsoft’s misunderstood era: Ben Gilbert of ‘Acquired’ on the tech giant’s most pivotal years Todd Bishop

“Every time a product ships, it takes us one step closer to the vision: a computer on every desk and in every home,” reads the marker in this Microsoft courtyard, with plaques for many of its early products. Missing is the internal addendum “… running Microsoft software.” (GeekWire Photo / Todd Bishop)

This week on the GeekWire Podcast, our guest is entrepreneur and investor Ben Gilbert, co-founder and co-host of the hit podcast Acquired.

Ben and his colleague David Rosenthal have developed a huge following for their deep-dive, long-form podcasts telling the stories behind some of the most successful companies in the world. They recently released Microsoft Volume II, the second installment in their epic exploration of the Redmond-based tech giant. 

Ben Gilbert of Acquired.

These are the years 1995 to 2014, from Bill Gates to Steve Ballmer, from Windows XP to Windows Vista and beyond — including Microsoft’s move into enterprise computing and video-game consoles, plus antitrust scrutiny, failed attempts to expand into mobile, and eventually its foray into the cloud, setting the stage for the company’s resurgence.

On this episode, we talk about Microsoft’s misunderstood era, with help from some archival clips of my own interviews with Bill Gates over the years. It’s a timely topic given Microsoft’s 50th anniversary in 2025 and the company’s revival as one of the most valuable and relevant companies in the tech industry with the rise of AI. 

I still report regularly on Microsoft, but from 2002-2008, the company was my singular focus as a beat reporter for what was then one of Seattle’s two daily newspapers, the Seattle Post-Intelligencer, a.k.a. the Seattle P-I.

After hearing Acquired’s Microsoft Volume I episode, knowing they would be telling the story of this era next, I went back and found some of my old interviews with Gates and others, and shared them with Ben to help with his research. 

We listen back to a few highlights from those interviews on this episode.

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I also ask Ben to catch us up on all things Acquired. The podcast is the talk of Silicon Valley and Wall Street, as documented in a Wall Street Journal profile. Acquired just announced a live arena show coming up on Sept. 10 featuring Mark Zuckerberg at Chase Center in San Francisco, home of the Golden State Warriors.

Here is Ben’s big-picture takeaway from this era of Microsoft’s history.

Bill Gates was right. Technology moves so fast that the biggest risk if you are a major technology platform, inventing and creating the platform of the future, is that the next one’s right around the corner, and you’re not really any better positioned to capture it than any young upstart.

There’s always a Google, and there’s always a Facebook after that, and I don’t believe that the Big 5 tech companies today are forever the Big 5 tech companies. OpenAI is this great example. … The next generation of technology broke through everything and completely rearranged all the chairs.

I’m just fascinated by the free market and the relentless pace of technology innovation, constantly throwing a wrench into any business leader trying to build this impenetrable moat around their business. Nothing is impenetrable.

Be sure to check out Acquired’s Microsoft Volume I and Volume II.

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Audio editing and production by Curt Milton.

https://ift.tt/e7ojcSU July 27, 2024 at 03:26PM GeekWire