5 Startups That Looked Dumb—Until They Were Worth Billions
About This Episode
Sam and Shaan explore why professional investors and entrepreneurs consistently underestimate the potential size of massive markets, using historical examples like Uber, Shopify, and Airbnb. They discuss the psychological biases that lead people to overestimate risk and analyze how AI is poised to disrupt the global labor market by expanding total addressable markets in ways similar to the transition from software to cloud.
Episode Description
Show Notes
Links
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Key Takeaways
Compensate for the human bias to underestimate opportunity by looking at how new technology creates entirely new use cases and price points rather than just replacing old ones.
Adopt a 'Park Avenue' investment strategy by prioritizing 'digital Manhattan' assets (like Bitcoin or foundational AI models) that are likely to outperform the market regardless of high initial valuations.
Manage information overload by using an 'intermittent fasting' approach to learning—focusing on research only when solving a specific personal problem or during dedicated, deep-dive 'think weeks' rather than reacting to daily news cycles.