Andy Rachleff (@arachleff) is the co-founder and Executive Chairman (prev CEO) of Wealthfront, an automated investment service startup to provide wealth advisor-like management to everyday folks. Andy co-founded Benchmark Capital in 1995 (one of the most successful venture capital firms of all time) and was a general partner until 2004. Prior to Benchmark, he was a GP with Merrill, Pickard, Anderson & Eyre. He has frequently been named to Forbes’ Midas List as a top tech venture investor.He teaches courses on technology entrepreneurship at Stanford Graduate School of Business and is a trustee of the University of Pennsylvania, chairman of the board of overseers for its School of Engineering and Applied Science and vice chairman of its endowment investment committee.He is also a board member of the Damon Runyon Cancer Research Foundation. In today’s episode we discuss: How to win at investing despite all the contradictory advice What makes for an investible landmark business Why Matt uses Wealthfront to manage his finances Where automation is headed in regards to jobs How the finance industry screws you sideways and rigs the game The problem with science and biotech research and how Andy’s solving it Why data and AI is the biggest thing happening today How the venture capital landscape is changing with the rise of SoftBank What does the future of blockchain look like Why Andy thinks going public is the way to go Thoughts on regulating tech monopolies and industries cycles What index investing does for average consumers