My First Million 5 Startups That Looked Dumb—Until They Were Worth Billions
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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.
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.
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.