You’re Underestimating How Much You Can Make

TL;DR

The video argues that humans systematically overestimate risk and underestimate opportunity, especially in technology entrepreneurship. Using Bessemer Venture Capital’s memo on Shopify (best-case exit $400M, actual $140B) and Bill Gurley’s “How to Miss by a Mile” analysis of Uber, it shows that experts constantly misjudge market size because new products create new use cases and expand total addre

Key insights

• Bessemer’s 2010 Shopify memo projected a best-case exit of $400M; Shopify is now worth ~$140B, and its GMV went from $132M to nearly $1T.
• Bessemer’s “anti-portfolio” (BVP.com/anti-portfolio) lists missed investments like Airbnb, Apple, eBay, Google – a humbling reminder that even top VCs miss the biggest opportunities.
• The professor who wrote a valuation teardown claiming Uber wasn’t worth $17B later admitted he had never used the product; this illustrates the danger of analysis without “skin in the game.”