20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable

In this episode of 20VC, Harry Stebbings interviews Tim Ferriss, delving into Ferriss's strategies for maintaining authenticity while navigating a public persona. They discuss the dangers of chasing sensationalism and vanity metrics, emphasizing the importance of focusing on key metrics aligned with core values. Ferriss shares personal experiences of feeling lost when prioritizing the wrong metrics, such as overemphasizing productivity and money, and how he course-corrects by engaging in activities detached from traditional productivity measures. The conversation explores Ferriss's early angel investing experiences, highlighting key lessons learned from successful investments like Uber and Shopify, as well as misses like One Password. They also touch on Ferriss's personal life, including his thoughts on relationships, the desire to become a father, and the importance of de-escalating conflict in partnerships. The episode concludes with a discussion about Ferriss's latest venture, a card game called Coyote, and his motivations for creating offline, human interaction.