Kyle Nakatsuji of Clearcover

An exclusive Tech Tribune Q&A with Kyle Nakatsuji (co-founder and CEO) of Clearcover, which was honored in our:
Tell us the origin story of Clearcover – what problem were you trying to solve and why?

Clearcover was founded in 2016 as entrepreneurial eyes turned towards insurtech and the next wave of fintech. My co-founder and COO, Derek Brigham, and I started thinking about how to establish a next generation insurance carrier, one that would focus on digital-first customers and stand alongside legacy carriers. It was clear to us that you can’t win this game in two or three years. We came up with ideas that we didn’t see being done in the insurance market and got right to work. We believed that creating a leading generational insurance company meant starting from the ground up and focusing on technology, as well as remaining steadfast in our commitment to customer centricity.

What was the biggest hurdle you encountered in your journey?

Clearcover was entering an industry with four major players spending a combined $6 billion on advertising every year. We wanted to focus on the customer experience and not spend on high-cost advertising. That strategy has worked. Clearcover now serves customers in 20 states across the U.S. and has raised more than $300 million in funding. We had to embrace the idea of being an underdog and still do today – it’s one of our core values.

My underdog mindset came from hurdles I faced earlier on in life. I played football throughout my time in school, and I loved the game and my team. So much so that when I tore my ACL my sophomore year of high school, I kept playing after my recovery. I ended up tearing my ACL again in my senior year, but stuck out the season, going on to play five more years in college. I learned what it feels like to try your hardest and fail – one of the most important lessons from my time playing college sports.

I carried that same perseverance with me to a “make or break” hurdle in my entrepreneurial journey. I started law school at UW–Madison, but soon realized it wasn’t for me and sought out a spot in its full-time MBA program. I soon ran into another hurdle. I had no business background, no GMAT, and not much of a resume due to football commitments. They told me “no” at the front desk. So I kept going back, week after week, until I got a yes.

What does the future hold for Clearcover?

Clearcover is consistently challenging the status quo with hassle-free insurance that redefines what it means to put the customer first. Our most recent addition of Car Care, the first offering of a new customer benefit called Clearcover Advantage™, is a great example of how we continue to find new ways to help support our customers to lower driving-related costs. On the company side, we are always looking to expand our services into new states and continue to hire and work with strong talent.

What are your thoughts on the local tech startup scene in Chicago?

Chicago has long been known as a hub for innovation and we are proud to have our roots here. The city continues to welcome new talent and be at the forefront of technological innovation. Not only does the city provide great talent, but it has an abundance of great companies to partner with and help expand our capabilities to more customers. The city has carved out an expanding niche in technology services that are attracting outside investment across multiple sectors, and we’re proud to call Chicago our home.

What’s your best advice for aspiring entrepreneurs?

My best advice is that it’s going to be the most difficult thing you’ll ever do in your life, but it will be one of the most rewarding. There will be times when people tell you no, but that’s when you have to keep moving forward and keep pursuing opportunities until someone says yes. If I didn’t keep pursuing an admission to the MBA program, I might not be where I am today. Don’t get into business for a quick win. Be ready and prepared for the long game.


For more exclusive interviews, see our full Profile of a Founder series