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Entrepreneur and investor Ben Gilbert, co-founder of the podcast Acquired, recently released Microsoft Volume II, which delves into the years 1995-2014 of the Redmond-based tech giant. The podcast covers the era from Bill Gates to Steve Ballmer, exploring Microsoft’s move into enterprise computing, video-game consoles, antitrust scrutiny, failed attempts in mobile, and their eventual foray into the cloud. This period sets the stage for Microsoft’s resurgence, making for a timely topic ahead of the company’s 50th anniversary in 2025 and its current relevance in the tech industry with the rise of AI.

The host shares archival clips from interviews with Bill Gates from his time as a beat reporter at the Seattle Post-Intelligencer, offering insights into Microsoft’s misunderstood era. Ben Gilbert points out the fast-moving nature of technology, highlighting the risk for major technology platforms of being surpassed by new upstarts. He reflects on the constant innovation and disruption in the tech industry, recognizing that the Big 5 tech companies today may not remain at the top forever as new players enter the market. OpenAI serves as an example of how technology breakthroughs can completely change the landscape.

Ben Gilbert provides a big-picture takeaway from Microsoft’s history, emphasizing the need for tech companies to constantly innovate and adapt to the ever-changing market. He discusses the challenge of building a sustainable business in the face of rapid technological advancements, noting that even the largest companies are not immune to disruption. Acquired’s Microsoft Volume I and Volume II offer listeners a deep dive into the inner workings and strategies of one of the world’s most successful companies, shedding light on the factors that contributed to Microsoft’s growth and resurgence over the years.

Acquired, as a podcast, has garnered attention and acclaim in Silicon Valley and on Wall Street, attracting a dedicated following eager to hear the stories behind some of the most successful companies in the world. The podcast’s live arena show featuring Mark Zuckerberg at Chase Center in San Francisco is a testament to its popularity and influence. The in-depth exploration of Microsoft’s history, as well as other companies covered by Acquired, provides valuable insights into the dynamics of the tech industry and the strategies that have helped shape the success of these companies.

The fast-paced nature of technology innovation constantly challenges business leaders to stay ahead of the curve and adapt to new trends and technologies. Ben Gilbert’s observations on the free market and the changing landscape of the tech industry highlight the importance of remaining agile and nimble in order to succeed in such a competitive environment. Acquired’s coverage of Microsoft’s history serves as a reminder of the company’s resilience and ability to evolve over time, adapting to new challenges and opportunities in order to remain relevant and successful in the ever-evolving tech landscape.

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