Anti-Portfolio Exceeds Portfolio

In the world of entrepreneurship and investing, the opportunities you miss often far outweigh those you take advantage of, even for the most successful people. This reality of business is both humbling and instructive.

Key Points:

• Anti-Portfolio Concept

  • Bessemer Venture Partners has a section on their website called "anti-portfolio" that honors all the great companies they had the opportunity to invest in but passed on
  • Their anti-portfolio includes massive successes like Airbnb, Apple, eBay, and Google
  • This represents the opposite of showing off successful investment memos - it's about humbling yourself

• Reality of Business Success

  • "For anybody who's worth a damn in business, your anti-portfolio is gonna be much bigger than your portfolio" - Shaan Puri
  • This is true for anyone who's good and has been in the game for a decent amount of time
  • It's a "bizarre situation" but consistent across successful investors

• Examples of Missed Opportunities

  • Airbnb was initially seen as just "couch surfing" but became 10,000 times bigger
  • Uber was dismissed as just "black car limos" for rich people in San Francisco
  • Musically (likely referring to what became TikTok) was seen as just kids making lip sync videos

• Hits-Driven Business

  • In tech investing and entrepreneurship, you can be wrong 8 or 9 times out of 10 as long as you get one right in a big way
  • This differs from other fields like school, regular jobs, or even Warren Buffett's approach to investing

• Optimism vs. Cynicism

  • "In our business, the cynics get to be right and the optimists get to be rich" - Shaan Puri
  • Cynics might be right 8 out of 10 times, but optimists are the ones who get rich by catching the big opportunities