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Who is THE entrepreneur of the Internet Era? In this episode, we cover the round of 16 matchups as voted on by YOU. (Originally posted November 2021)
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In this special episode of the Tech Meme Ride Home, hosts Brian McCulloch and Chris Messina kick off a unique competition to determine the 'na plus ultra entrepreneur' of the last 30 years. Joined by Ben Gilbert and David Rosenthal from the Acquired podcast, the hosts will dissect and debate the profiles of various entrepreneurs presented in a bracket format, leading up to a final winner as voted by listeners.
The first round pits Evan Spiegel of Snapchat against Reed Hastings of Netflix. Hastings emerges as the clear winner. The hosts discuss Spiegel's innovative contributions to social media, particularly the creation of ephemeral messaging and the 'stories' format, contrasting the impact of both entrepreneurs’ approaches to their respective industries.
Next, Jack Ma of Alibaba faces off against Jeff Bezos of Amazon. Bezos wins decisively, but the hosts delve into the unique aspects of Alibaba's business model compared to Amazon's, particularly regarding B2B e-commerce. They highlight how both entrepreneurs shaped their national tech industries - Ma’s influence in China and Bezos's in the US.
The third round is an unexpected upset where Dorsey defeats Zuckerberg, leading to discussions about personal sentiment towards both entrepreneurs. The debate reveals stark contrasts in their business philosophies and public personas, with the hosts weighing in on what it means for Zuckerberg's legacy as an entrepreneur.
Katrina Lake, founder of Stitch Fix, faces off against Elon Musk. Despite a noble argument for Lake's achievements in building a capital-efficient business, Musk secures a strong victory based on his broader cultural impact and innovation across multiple high-profile companies like Tesla and SpaceX.
In a nail-biting matchup, Patrick Collison just barely beats Oprah Winfrey. The conversation touches on Oprah's transformative media influence and how she shaped the concept of an influencer. Collison's rising status as a notable entrepreneur highlights the transition towards tech-centric leadership.
Whitney Wolfe Herd of Bumble competes against Bill Gates of Microsoft. Gates wins convincingly, but the discussion brings to light Herd’s significant contributions to dating apps and her stance against established norms in tech, showcasing a modern entrepreneur's approach.
In a 'battle of the Larrys', Page and Brin dominate Ellison, with the hosts reflecting on the difference in their entrepreneurial paths. They discuss Ellison's business acumen and his contributions to both Oracle and the technology landscape as a whole.
In the final matchup of the episode, Steve Jobs decisively beats Mark Benioff. The hosts discuss Jobs's unparalleled influence on personal computing and design, as well as Benioff's role in shaping the SaaS industry. This leads to a broader discussion about the evolving definition of entrepreneurship.
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