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 garnered a huge following for their deep-dive, long-form podcasts that chronicle 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.
These are the years 1995 to 2014, spanning from Bill Gates to Steve Ballmer, from Windows XP to Windows Vista and beyond — including Microsoft’s ventures into enterprise computing and video-game consoles, antitrust scrutiny, failed attempts to expand into mobile, and eventually its foray into the cloud, setting the stage for the company’s resurgence.
In this episode, we delve into Microsoft’s misunderstood era, with the aid of some archival clips from my own interviews with Bill Gates over the years. It’s a timely discussion given Microsoft’s 50th anniversary in 2025 and its revival as one of the most valuable and relevant companies in tech with the rise of AI.
I continue to report on Microsoft regularly, but from 2002-2008, the company was my exclusive focus as a beat reporter for what was then one of Seattle’s two daily newspapers, the Seattle Post-Intelligencer, also known as the Seattle P-I.
After listening to Acquired’s Microsoft Volume I episode, knowing they would be narrating the story of this era next, I went back to find some of my old interviews with Gates and others, and shared them with Ben to assist in his research.
We revisit a few highlights from those interviews on this episode.
I also ask Ben to update us on all things Acquired. The podcast is the talk of Silicon Valley and Wall Street, as documented in a Wall Street Journal profile. Acquired recently announced a live arena show slated for Sept. 10 featuring Mark Zuckerberg at the Chase Center in San Francisco, home of the Golden State Warriors.
Here is Ben’s overarching 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 a prime 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.
