My First Million

5 Startups That Looked Dumb—Until They Were Worth Billions

794 snips
May 23, 2025
Dive into the world of underestimated startups that eventually skyrocketed to success. Discover how Shopify's rise illustrates the pitfalls of investment misjudgment. Learn about the importance of a visionary mindset and the surprising potential of niche markets. The discussion reflects on missed opportunities and the necessity of balancing conviction with caution in high-stakes investments. Explore how innovation in AI and ride-sharing is reshaping industries, challenging perceptions, and driving consumer behavior.
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Bessemer's Shopify Underestimation

  • Bessemer invested in Shopify with a best case exit of $400M, yet it's now valued at $140B.
  • Even top VCs vastly underestimated Shopify's market size and opportunity.
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Sam's Market Misjudgments

  • Sam Parr admits he underestimated success of meditation apps, Snapchat and Airbnb.
  • He thought these markets were niche but they became billion-dollar industries.
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Anti-Portfolio of Venture Capitalists

  • Every successful VC or entrepreneur has a long list of missed opportunities, the "anti-portfolio."
  • Missing big bets is an inevitable part of the game to achieving outsized returns.
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