20VC: Andy Rachleff, Founder @ Benchmark & Wealthfront on What Makes The Best CEO & Board Member & Why Ivy League Endowments Are The Best Managed Capital In The World

From 1995 until 2004 Andy Rachleff was a co-founder and General Partner of Benchmark Capital, who have backed the likes of Twitter, Snapchat, Dropbox, Uber and Instagram. Upon his retirement from Benchmark, Andy joined the faculty of the Stanford Graduate School of Business to teach a variety of courses on entrepreneurship. In 2008 he co-founded Wealthfront Inc, the online financial advisor and investment management solution,  where he now serves as Executive Chairman. In just 3 years, Wealthfront now have over $2bn AUM.

  

1.) How Andy made his way into the world of VC and what was the origin story behind the founding of Benchmark?

2.) Andy took the opposite route to most having been a VC and then founding Wealthfront. So what does Andy make of doing VC first and then becoming an operator?

3.) Why does Andy believe Ivy League endowments are the best managed pools of capital? What do they do well and what separates the good from the great?

4.) Andy has worked with some of the world's best CEO's and board members, so what makes the best board member and what makes the best CEO?

5.) How has Andy seen the VC industry evolve and develop over the last 20 years? How has Andy seen his own investment decision making process and patter recognition alter over that time?

Items Mentioned In Today’s Episode: 

Andy’s Fave Book: The Innovator's Dilemma

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