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Kyle Nakatsuji: “Courage isn’t the lack of fear”

You must have the courage to keep moving forward when things are hard, and you have to be resourceful to find a path when it’s hidden. Courage isn’t the lack of fear. It’s the choice to override the fear. Couple that with the unflappable persistence to find a solution and that’s resilience made tangible. I […]

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You must have the courage to keep moving forward when things are hard, and you have to be resourceful to find a path when it’s hidden. Courage isn’t the lack of fear. It’s the choice to override the fear. Couple that with the unflappable persistence to find a solution and that’s resilience made tangible.


I had the pleasure of interviewing Kyle Nakatsuji, Co-founder and CEO of Clearcover.

Kyle is the co-founder and CEO of Clearcover, the smarter car insurance company. Under Kyle’s leadership, Clearcover has raised more than 104 million dollars to date and has launched in multiple markets — California, Illinois, Arizona, Ohio, Utah, Texas, Wisconsin, Louisiana with more on the way. Before founding Clearcover, Kyle was a founding member of American Family Ventures where he was responsible for sourcing, evaluating and structuring over 50 equity and debt venture capital investments in nationally-based tech startups. Prior to this role, Kyle was a corporate attorney focused on emerging company business matters at AlphaTech Counsel. Kyle has a law degree and an MBA from the University of Wisconsin.


Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

Like many entrepreneurs, I was unsure of my exact future after getting my BA in Political Science at University of Wisconsin-Oshkosh. I had grown up in Milwaukee and I was lucky to have the support to explore my options while majoring in Political Science. I “tried out” law school post-graduation but quickly realized that wasn’t the right fit. After looking around for ways to increase my career options (and apparently, not very hard), the business school just across the street caught my attention.

So, I went across the street and 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.”

So they said very nicely as Midwesterners do, “Well, why don’t you go away?.”

But I kept coming back week after week to a kind woman there, Erin Nickelsberg, 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 me because I was finally accepted. From there, I spent a bunch of time trying to get real-world business start-up experience. Primarily, through clinical programs at the university where I could work hand-in-hand with local startups and learn the ropes in real-time. Which is a great segue into your next question…

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful to who helped get you to where you are? Can you share a story?

My success so far has been dependent on many people…Erin Nickelsberg mentioned above — she took a chance on me. Peter Gunder who hired me to help start the VC fund at American Family. I had very little experience but he believed in me, and that really started everything. He eventually became Clearcover’s first Board Member and Investor. I’m grateful to my co-founder, Derek Brigham who took a very big chance on helping me start the company and lending his 30+ years of insurance experience. I’m also grateful to Clearcover’s first employee (our “first follower”), Clearcover’s first customer — actually every customer ever — these are the people that brought Clearcover into existence.

However, I can’t answer this question without acknowledging my mom. She raised me in challenging circumstances while also working as an administrative leader in the local school district. She helped improve schooling in our town while also balancing the demands of being a great mom. She provided the right amount of structure and freedom to teach me the value of pursuing hard goals. There’s absolutely no way I’d be who I am today without her as a role model.

What do you think makes your company stand out? Can you share a story?

If we aren’t making our customers’ lives easier than we aren’t standing out in the way that matters. We founded Clearcover with the mission to help digitally-native consumers have a fully digital insurance company that understood their needs (which includes paying less for great coverage.)

Given our age, we’ve had the benefit of access to the latest technologies like the cloud and AI to build a convenient, personalized, and mobile-first experience. You can do everything you need to do with your car insurance policy (make payments, file a claim, chat with our Customer Advocates, etc.) on your phone. We measure our success by the efficiency of our processes so our customers can enjoy quality, convenience, and cost-savings. For example, close to 85% of our policy sales occur unassisted online. We’ve also adjusted 96% of our PD claims virtually — helping most customers to be repaid in 2 business days. Our customer satisfaction score hovers around a 95% so we feel good about what we’ve built so far but we have so much more to do.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Great question. It’s a trait that’s been important throughout all of history. From my perspective, it’s the ability to keep going when the majority of other people would quit. This ability consists of two characteristics; courage and resourcefulness. You must have the courage to keep moving forward when things are hard, and you have to be resourceful to find a path when it’s hidden. Courage isn’t the lack of fear. It’s the choice to override the fear. Couple that with the unflappable persistence to find a solution and that’s resilience made tangible.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

It’s never just one person, it’s so many people. It’s the unsung, silent heroes out there who work multiple jobs, get up early, go to bed late, and do hard things to keep others healthy and safe. This could be the single parent, the frontline nurse, or our sanitation workers. People in tech tend to get credit for doing hard things and being resilient, but I think there are millions of resilient people doing amazing things every day that deserve that attention too.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

There’s been a few times but the one that’s most relevant to Clearcover happened in 2016. After spending months ruminating, I took a risk to pitch the idea to my boss at American Family. I’ll never forget his face as he responded with obvious hesitation, “So you want to start a competitor in a market where the top four leaders spend a combined 6B dollars on advertising every year? And you want to spend barely any money on advertising to instead focus on experience?”

From there, I’ve heard ‘You’re crazy’ at least over 100 times. Between car insurance being dominated by massive competitors, a tough regulatory market, and predictions (now outdated) that autonomous cars will eliminate the need for car insurance, the odds were not in my favor. But that’s generally how the biggest opportunities work, right?

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

I can share a setback from two years ago…I don’t know if it caused me to bounce back stronger per se but it certainly made me more resilient.

Clearcover first launched insurance in California. With most products, including insurance, it takes a bit of time to understand if it’s going well — is pricing correct? Is market demand there? In less than 90 days, we had over 1500 new customers and we felt great. But we were growing too fast and in danger of running out of funding. We needed to raise a Series B..and fast.

Tomasz Tunguz at Redpoint VC once said a Series B funding is the most challenging round for a startup company and it’s very true. It’s a delicate balance of having enough proof to show the company is worth funding but not so much ‘proof’ that you’re about to grow yourself into bankruptcy.

After about 15 ‘no’s’ in a row, I had to admit to myself (and my board) that I wasn’t going to be able to raise the round in time. That was a tough conversation. American Family stepped up to help us close the new round of funding with the addition of two new investors — Cox and Hyde Park Angels.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

Hmm, I have many experiences from growing up and learning from my parents. One that stands out for me happened during my senior year of high school.

During the first play of the first football game of my senior year, I tore my ACL. It was the second time in two years I tore the ACL in that knee, and it was clear that I should take the season off to heal. But football was my life at the time — I had spent most of the last six years preparing for this season and how it could launch my college career. And more importantly, our team had worked hard to prepare for the season and were relying on me to be there. I didn’t want to let them down.

So, my parents and doctors put the power to make the decision in my hands — keep playing through the pain or take a break. That was a moment where my resilience was tested — was I willing to do the nearly impossible for an accomplishment that I wanted more than anything? I decided to play the remainder of the season on a torn ACL — trying to make it through each game and help the team as much as possible.

At the end of the day, I don’t know if this was a great choice. But I don’t regret it. And having the choice itself demonstrates how my parents created a place for me to learn that life doesn’t hand you anything. You have to work for it. That’s a mindset I bring to Clearcover every day.

Resilience is like a muscle that can be strengthened. In your opinion, what are the 5 steps that someone can take to become more resilient? Please share a story or an example for each.

Just 5 clear steps would be ideal but life is a bit messier than that. Everyone has to create their own steps to becoming more resilient because each individual is faced with unique challenges. Overall, my advice would be to keep choosing to do things that scare you and do it often. The more confidence you can build in your ability to actually ‘do the thing’, your own efficacy will grow and you’ll inherently become stronger.

As a start-up, Clearcover has faced many challenges in our last four years including a few catastrophic ones. None have been as challenging as maintaining our business through COVID-19 though. And one of the major reasons that we were able to survive as a business (in addition to good fortune and a supportive board) is that our team had already been tested time and time again. We’ve faced our fear before; resilience is coded into our culture. We’re still working to survive the impact of the pandemic but I’m confident in my team because they’re confident in themselves.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

How do I choose just one? It’s a long list…Warren Buffett, Mary Barra, Jeff Bezos, Serena Williams, Tricia Griffith, Jay-Z…if I had to choose, it’d likely be Jay-Z. I’ve always admired his work, both in music and business. He says it better than I…“Only two things can get you through this: that’s patience and persistence.”

How can our readers follow you on social media?

@clearcover

@Kylenakatsuji

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