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

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, and they recently released Microsoft Volume II, the second installment in their epic exploration of the Redmond-based technology giant. 

We talk about Microsoft's misunderstood era, with help from some archival highlights from GeekWire co-founder Todd Bishop's interviews with Bill Gates over the years. It’s a timely topic given Microsoft’s 50th anniversary in 2025 and the company's resurgence as one of the most valuable and relevant companies in the tech industry with the rise of AI. 

Before we jump in, we 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, the home of the Golden State Warriors. 

Edited and produced by Curt Milton.

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