Building a New Insurance Company From Scratch: Clearcover CEO Kyle Nakatsuji (Part 2)

Sramana Mitra: What year does that bring us up to?

Kyle Nakatsuji: Now, it’s 2012. I’ve finished both of the degree programs and I’m looking for a job. I ended up getting a job as an attorney. I was working at a firm that exclusively did tech startup work. I didn’t think I was going to be a lawyer.

I fell into that through a contact who was great and brought me on even though he probably knew I wasn’t going to last long. I was practicing law for about a year and wasn’t enjoying it as much as I thought I should. I wasn’t all that good at it.

It was a very small law firm and when you work at a small law firm, it’s obvious that you’re losing money for the firm for quite a while. That’s not unique. The big firms have budgets to absorb that. Small firms’ money is coming right out of the founder’s pockets.

I had a moment where I was dealing with a lot of guilt. I knew I didn’t want to be there. I didn’t want him to have to pay me so I could look for another job and lose money for his firm. So I went to his office and I said, “Matt, I feel like I have to quit.”

Matt is awesome. He said, “Stop being so dramatic. Why don’t you hang out and work part-time while you look for something else.” I did. A couple of weeks later, he introduced me to Peter, who was, at the time, the Chief Investment Officer at American Family Insurance in Madison, Wisconsin.

Peter, said, “We’re looking to start a venture capital firm or a venture capital activity with an American family. A couple of my contacts tell me that you’re unusually interested in entrepreneurship and venture capital. How would you like to come and help us start that?”

I didn’t know anything about insurance at the time, but that sounded like a hell of a job offer. So I went and did the interview with Peter. He then hired me at the very end of 2012 or early 2013 to go and help co-found the venture capital group at American Family Insurance. That was after the year of being in law. That was my first real foray into venture capital.

Sramana Mitra: What year are we at now?

Kyle Nakatsuji: We’re in 2013. I had jumped in to help American Family start their venture activities. I was in a small team there. A gentleman named Dan Reed is the Managing Director there now. He and I were spending a lot of our time on this.

Peter deserves most of the credit because he was the one who had the foresight to say, “As an insurance company, one thing that we possess is a large pile of money. But we know that we’re going to have to make some bets and learn about how technology is going to affect our industry.” He had that foresight to see that insurance was going to be affected by technology in meaningful ways in the coming years.

So, why not partner with companies by investing in them because we have the capital? Then we can gain the expertise and maybe there’s some investment return embedded along the way. We went to work on building that group.

This segment is part 2 in the series : Building a New Insurance Company From Scratch: Clearcover CEO Kyle Nakatsuji
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