Motivation and Growth in Entrepreneurship

My guest today is 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. Thrive has gone from strength to strength since then and now manages $15 billion with a small team of 9 investors. 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. Josh rarely speaks in public about the firm and their philosophy so it was a blast to do this with him. 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

(00:03:14) - (First question) - Why do this podcast

(00:06:14) - The development of taste and quality 

(00:10:20) - CS Lewis tweet; The Inner Ring

(00:11:53) - Founders being heroes and motivating quietly from the background

(00:16:14) - Overview the founding story of Oscar Health

(00:21:30) - Is a big business different from a small one

(00:23:18) - Learning to identify good problems and creating a business to solve it 

(00:25:43) - The birth story of Thrive Capital 

(00:30:14) - Lessons learned from creating the first three Thrive funds

(00:33:35) - Industry wide competition today and models for building a firm in general 

(00:37:44) - Talent, recruiting and seeing potential in younger generations of people

(00:45:40) - Investments he made during the early foundation of Thrive that had significant impact 

(00:49:12) - His analogy for investing in early versus late stage

(00:54:22) - The current macro environment

(00:57:52) - Giving AI companies computing power instead of money

(00:58:57) - Why he sold small stakes of Thrive 

(01:03:10) - His philosophy on what makes a good product

(01:05:20) - What he thinks about the models like Mobile and Cloud 

(01:08:10) - His absence from crypto and why he refrained during the boom in 2021

(01:10:33) - Thoughts about the opportunity set in FinTech today writ large

(01:12:04) - Other potential opportunity sets beyond what’s already been discussed

(01:13:39) - Lessons learned from his time spent with Marc Andreessen, Stan Druckenmiller, Henry Kravis, and David Geffen

(01:21:59) - Balancing magnitudes of capital between investment funds 

(01:23:32) - Why founders choose Thrive

(01:29:15) - Vision as a key ingredient for founders

(01:32:19) - His view of the investment industry in the world today writ large 

(01:40:19) - Other investment firms he would invest in

(01:42:48) - The kindest thing anyone has ever done for him