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Andy Rachleff (@arachleff), president and CEO of Wealthfront, joins Anne Dwane and Lucas Bagno to discuss:

- What Andy learned from endowment investing and his quest to democratize excellent investing advice at Wealthfront.

- Why you shouldn’t try to time the market and why in his opinion all-time highs are “absolutely irrelevant.”

- Andy’s lessons from witnessing four day-trading frenzies in his career and why you should think about absolute return rather than relative returns.

- How his position on crypto has evolved over time and why he’s optimistic about its ability to revolutionize commerce but skeptical about its place in an investment portfolio.

- His learnings on product market fit from Don Valentine, and why Don said that if a startup can screw something up, it will. He also said that to succeed, it needs the market to pull the product out of the startup’s hands.

- Why operating investors often make better investment decisions because operating experience is a proxy for network rather than because of the operating experience itself.

- His top book recommendations.

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