Wisdom in Listening and the Pitfalls of Social Chasing

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. This is a rare opportunity to hear from one of the best investors of the past decade—Josh Kushner, founder and managing partner of venture firm, Thrive Capital.

Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Please enjoy my great conversation with Josh Kushner.

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For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Show Notes

(00:00:00) Welcome to Invest Like the Best

(00:05:14) Why do this podcast

(00:08:14) The development of taste and quality 

(00:12:20) CS Lewis tweet; The Inner Ring

(00:18:14) Overview the founding story of Oscar Health

(00:25:18) Learning to identify good problems and creating a business to solve it

(00:27:43) The birth story of Thrive Capital

(00:32:14) Lessons learned from creating the first three Thrive funds

(00:39:44) Talent, recruiting and seeing potential in younger generations of people

(00:47:40) Investments he made during the early foundation of Thrive that had significant impact

(00:51:12) His analogy for investing in early versus late stage and styles of real estate investing

(00:56:22) The current macro environment

(01:00:57) Why he sold small stakes of Thrive

(01:05:10) His philosophy on what makes a good product

(01:10:10) His absence from crypto and why he refrained during the boom in 2021

(01:12:33) Thoughts about the opportunity set in FinTech today writ large

(01:15:39) Lessons learned from his time spent with Marc Andreessen

(01:17:43) Lessons learned from Stan Druckenmiller, Henry Kravis, and David Geffen

(01:22:09) Firm values he thinks are very important

(01:31:15) Vision as a key ingredient for founders

(01:34:19) His view of the investment industry in the world today writ large 

(01:44:48) The kindest thing anyone has ever done for him