Building a New Insurance Company From Scratch: Clearcover CEO Kyle Nakatsuji (Part 1)

The insurance industry is archaic and offers much room for re-engineering. Kyle discusses how he is going about it.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Kyle Nakatsuji: I was born in Milwaukee, Wisconsin. I was born and raised in the Midwest. I went to undergrad at a college in Wisconsin and then got a law degree and an MBA at the University of Wisconsin-Madison.

Sramana Mitra: What timeframe did you come out of college in? What year are we talking?

Kyle Nakatsuji: I finished my undergraduate degree in 2008. Then I did a dual law degree/MBA program that lasted for four years. So I finished my MBA in 2011 and my law degree in 2012.

Sramana Mitra: What happens next?

Kyle Nakatsuji: That’s the abridged version of the story. I was a political science major in undergrad. I didn’t spend all that much time in class. Actually, I was a football player and I was more concerned with that than going to school. Since a significant percentage of political science majors don’t know what to do next, I went to law school because that meant I didn’t have to go get a real job.

I went to law school and didn’t know much about what it meant to be an attorney. About three or four weeks in, I realized I wasn’t sure that’s what I wanted to do. I started looking around for ways to increase my career options.

The business school was across the street. So, I went across the street over to the business school, and I said, “I’m a law student. I’d like to get an MBA as well.” They said, “Great. So, tell me how many years of work experience have you had?” I said “Well, none.” They said, “Okay. Tell me about how many business courses you’ve taken and what you’ve learned.” I said, “I actually haven’t taken any business courses.” They said, “Well, why don’t you go away.”

I kept coming back week after week to a very nice woman there who listened to me week after week with a new plan as to how I could convince them to let me in the business school. Finally, either I came up with the right plan or she got sufficiently sick of hearing from me. They ended up letting me in.

I started my MBA the next year, which was fantastic except I hadn’t thought much further ahead than getting into the college. I hadn’t really thought much about what happens after that. What do I actually want to study? What do I want to be? Why am I here? So I started looking around for my reason for being there after I was accepted.

In my exploration, I landed on entrepreneurship and venture capital. I had one of these moments that people occasionally have where I said, “I can’t believe this is a job.” This sounds amazing. People get paid to do this, which is great. I would like to get paid to do this too. Unfortunately, what that meant is that all of the things I really wanted to learn weren’t being taught in a ton of the classes I was taking.

I was looking around in my constitutional law course and I didn’t see a ton of startups or other entrepreneurs. After all of that work, I ended up not spending much time in class. I was admittedly an absentee student at that point, but I had at least found what I really wanted to learn.

I spent a bunch of time learning in whichever way I could. Primarily, through clinical programs at the university where I could work hand-in-hand with local startups and learn the ropes in real-time. So, the short version of the story is, I got a law degree and an MBA.

The longer version of the story is that it was a bit of a meandering path which didn’t involve a lot of showing up in class, but did involve a lot of learning the things that I thought were important.

This segment is part 1 in the series : Building a New Insurance Company From Scratch: Clearcover CEO Kyle Nakatsuji
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