Lessons

• Capital is commoditized. Investors need to compete on other aspects in order to win deals.

• Venture capital is becoming a race to form relationships with entrepreneurs earlier and earlier in their life cycle. How can you add value to a founder before it comes time to invest in them?

• Generational transition is an issue within any fund. Nobody wants to think about succession until it’s too late.

• Look for application-oriented use cases for any investment. There are too many investors chasing deals because of FOMO.

• Over-indexing on a presentation is the wrong way to evaluate opportunities. You have to meet with founders in order to get their perspectives and learn about their unique insights.

• Track record > media presence. Andrew has no audience. He’s also invested in multiple unicorns. 

• Storytelling should be your greatest strength as a founder or fundraiser. The better you are at crafting the story, the more luck you produce.

• Develop a chip on your shoulder early in your career. Too many people reach an arbitrary title and coast. This leads to stagnation and later regret.

• Universities are the starting point for startup ecosystems. Students must become comfortable with taking risks before being steered to safe jobs.

• You have to be willing to fail and test your emotions on things in order to move forward and improve. Thick skin is a superpower.

• Some of the best founders are those that are design-obsessed. Airbnb is probably the most famous example of this.

• You have to be an optimist in startup world. Investing in illiquid assets is irrational. You have to believe the future looks much brighter than the future.

• Make a pitch as engaging as possible so you create opportunities for shared dialogue and questions. People like being talked with more than they like being talked at.

• Being a contrarian has its downsides. If you bet on the wrong market, you have no chance to be right.