Entrepreneur and investor Ben Gilbert, co-host of the podcast Acquired, discusses Microsoft’s history on the GeekWire Podcast. The focus is on the years 1995 to 2014, covering the period from Bill Gates to Steve Ballmer, Windows XP to Windows Vista, and beyond. This includes Microsoft’s expansion into enterprise computing and video-game consoles, as well as its struggles with antitrust scrutiny and failed attempts in the mobile market before eventually finding success in the cloud. The podcast delves into Microsoft’s misunderstood era, timed with the company’s 50th anniversary in 2025 and its resurgence in the tech industry with the rise of AI.
The podcast features archival clips from interviews with Bill Gates, shedding light on Microsoft’s journey during that time. The host, who was a beat reporter for the Seattle Post-Intelligencer focusing on Microsoft from 2002-2008, shares insights from his interviews with Gates and others with Ben, aiding in the podcast’s research. The discussion also includes highlights from those interviews, providing a unique perspective on Microsoft during that era and showcasing the company’s challenges and successes.
Ben Gilbert shares his big-picture takeaway from Microsoft’s history, emphasizing the rapid pace of technology innovation and the constant threat of new competitors disrupting established tech giants. He points out that major technology platforms are always at risk of being overtaken by new upstarts, highlighting the need for companies to continuously innovate and adapt to remain competitive in the ever-evolving tech landscape. He mentions OpenAI as an example of how the next generation of technology can redefine the industry and reshape the competitive landscape.
Acquired, the podcast co-hosted by Ben Gilbert, is well-regarded in Silicon Valley and on Wall Street, with a forthcoming live arena show featuring Mark Zuckerberg. The podcast’s in-depth exploration of successful companies, including Microsoft, has garnered a large following and critical acclaim. Ben’s insights into Microsoft’s history and the broader tech industry offer valuable lessons for business leaders and entrepreneurs looking to navigate the challenges of an increasingly competitive and fast-paced market.
The podcast episode on Microsoft’s history provides a comprehensive overview of the tech giant’s evolution during the years covered, from its leadership changes to its product developments and strategic shifts. The discussion includes Microsoft’s successes, such as its foray into the cloud, as well as its failures and missed opportunities in areas like mobile technology. The podcast serves as a reminder of the importance of staying nimble and adaptive in the face of rapid technological advancements and evolving market trends.
In conclusion, Ben Gilbert’s reflections on Microsoft’s history underscore the relentless pace of technology innovation and the need for companies to continually reinvent themselves to stay relevant and competitive. The podcast episode offers a valuable retrospective on Microsoft’s journey during a pivotal period in its history, highlighting the challenges, successes, and lessons learned along the way. As technology continues to evolve and disrupt established industries, the story of Microsoft serves as a reminder of the ever-changing nature of the tech landscape and the importance of innovation and adaptation for long-term success.
