Josh Kushner talks entrepreneurship at SXSW

SXSW SPOTLIGHT — CNN’s Laurie Segall interviewed Josh Kushner, founder of Thrive Capital and health insurance startup Oscar (named for Josh’s great-grandfather) that was recently valued at $2.7 billion. Some highlights…

Segall: “You come from a real estate family, what was it about the startup community that really appealed to you?”

 “My co-founder Mario and I started something while in college and it grew to be really large with a few bumps along the way… The honest answer is luck. Once you have this feeling where you reach tens of millions of people and the decisions you make from a product perspective are impacting their lives and making their days different it’s just so intoxicating you never want anything else again and when you lose it you want to do everything you can to get it back. Luck in the beginning but I just can’t imagine doing anything else.”

Segall: “Your whole career has kinda been defined by the David vs. Goliath mentality. You came from a family where there’s always the public eye, doing a lot, you could have gone a certain way, and it would have been pretty easy, but you’ve always had that for some reason. Why do you think that is?”

 “Perception is not always reality. I’m second generation but I kinda grew up in an immigrant-like home. Since I’ve been growing up I’ve been taught that this is the greatest country in the world and based on where my grandparents came from, they didn’t have the opportunities that we have, so like do everything you can to make the most of it. But again been very lucky.”

Segall: “You have a company worth $2B, invested in all these winning startups, make us all feel better and talk about failing. Have you ever just failed? You really seem to be crushing it and I truly don’t believe that you have the highs without the lows. Let’s have a little therapy session (laughter) so take me to one of those lows, when was it? How did it go down?”

“I was joking with someone at the office the other day. I feel like entrepreneurship is like the volatile experience of feeling completely overwhelmed by the fact that you don’t know how you’re going to deal with the problems you’re facing vs when things are ok feeling completely insecure that you don’t have enough going on, which is totally irrational. Mario and I started a company that was very large and isn’t anymore. That was a painful experience to have but, I think in reality, every day there’s failure, everyday something is broken and you have to fix it and be ok with not being right all the time and just adapting.”

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