“My deepest insecurity is that I have these intuitions about things that I cannot explain to anyone,” Kushner told Rubin as they sat in his garden overlooking the ocean. “Sometimes I see or experience something and it makes sense to me, I fall in love, but I cannot explain why. Like when Thrive invested in Instagram or Spotify or OpenAI. I could... See more

The more you see, the more skeptical you become. Optimize for skepticism and curiosity. Having been a VC and invested as an angel in well over 100 companies, my inbox flows with ideas of all kinds from aspiring and repeat entrepreneurs. In the earlier days, I’d get excited by ideas especially the first time I saw them. But over time, I soon... See more