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Meeting Tim Ferriss, Real Estate & SaaS ideas (#395)

From My First Million · Published Jul 5, 2023 · Watch on YouTube

TL;DR

The episode covers three main topics: insights from an interview with Tim Ferriss about his philosophy on investing (selling too early, having an exit plan), project selection (picking projects where the process itself is a win), and interview tactics; a real estate billionaire who built a $1B portfolio in 7 years by focusing on retail categories still expanding (DIY, black/Latino communities, dol

Key insights

  • Tim Ferriss's biggest investing mistakes were selling winning assets too early (e.g., Shopify, Twitter, Facebook pre-IPO shares sold right after lockup); he now only buys if he knows the conditions un
  • Ferriss selects projects by asking: "How do I win even if this fails?" – ensuring the creative process, the people met, and the skills developed are themselves valuable.
  • Ferriss’s approach to interviewing Sam Bankman-Fried would involve: talking to old friends/coworkers to get heartfelt questions, using their names to soften the interviewee, and directly asking what p

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