How to launch an insurance company - 2018 in review

By Kyle Nakatsuji  3 minute read

By Kyle Nakatsuji

3 minute read

2018 was the year Clearcover went from concept to reality. After months of research and preparation—and a frantic push to get our product out the door—Clearcover car insurance went live in February. It was an unforgettable moment. Now, eleven months later, we’ve sold thousands of policies, put in many late nights, and learned a lot about how to run an insurance company.

Here are some of the biggest milestones we achieved this year.

We sold our first policy.

We started Clearcover with a simple hypothesis: if you can offer high-quality insurance products at an attractive price, you’ll find customers—even if you don’t spend a billion dollars on advertising or have a 100-year-old brand. We’d seen the market need for a new kind of insurance company—one built on a completely different operational and technical foundation than the current industry players—and we felt, instinctively, that the Clearcover model would work.

By the beginning of 2018, we’d been working on our concept for over a year, formalizing strategic partnerships, growing our team, and building a robust tech platform and API suite that would allow us to sell insurance more efficiently so we could pass the savings on to customers.

Still, we weren’t an insurance company yet. Our policy count was zero. Therefore, on January 1st, our biggest questions were simple: Can we just sell one policy? Can we get this product out the door? Will anyone buy it?

So it was a big moment when, on February 7th, the Clearcover team gathered to watch the sale of our first auto insurance policy.


It was a major accomplishment. In one day, we’d become a real insurance company.

Now, we just had to figure out how to be a good one.

We learned a lot and solved a variety of problems in a very short amount of time. And it paid off: we’ve now underwritten tens of thousands of policies and we’re projected to grow even faster in 2019.

We learned how to be an insurance company.

The first 60 days in business proved two things: first, it was clear that our business model worked. We sold thousands of policies in the first two months, a dramatic growth rate that even we hadn’t anticipated. Obviously, the market liked our product.

However, it also became clear that we had a lot to learn about being an insurance company. Before launch, we’d prepared ourselves as much as we could for the everyday logistics of managing an insurance product, but, of course, we didn’t know what we didn’t know. And, soon after our insurance product went live, we realized pretty quickly that we had some big challenges to solve: we needed to provide a great claims experience for our customers, we had to grow in a way that appropriately balanced our short-term and long-term objectives, and we needed to make sure that we had cash available to do all of this well.

Addressing all of these challenges and learning how to scale our business took massive, coordinated effort from the Clearcover team. We learned a lot and solved a variety of problems in a very short amount of time. And it paid off: we’ve now underwritten tens of thousands of policies and we’re projected to grow even faster in 2019.

More importantly, we’re no longer a tech company that sells insurance—we’re a technology-based insurance company. This is a big milestone for us and one that I’m personally very proud of.

We’ve grown as a team.

It has been an amazing experience to work with the Clearcover team. Many of the people who work here do not come from an insurance background, and this was intentional. When first assembling the team, we knew that we would need the right blend of industry experience and fresh ideas to be successful. We needed people who could look at insurance from first principles, who could challenge assumptions about how insurance worked and what it could be.

2018 has proved that we found those people. It’s been amazing to watch the team grow, both in terms of skill sets and in the ability to apply those skill sets to an industry that hasn’t changed in decades. We’ve certainly been challenged, but we’re better for it. I’m very proud of the team we’ve built.

I’ve also enjoyed watching our cultural fabric grow and evolve. Anyone in startup culture knows the catchphrases—nearly every startup claims to value ingenuity, reward courage, and provide a flexible work environment. Frankly, we say many of the same things. But I’m proud to say that we’ve put in the work to ensure we’re following through on our promises.

We’re still developing as a team, of course, but I see the proof points of success when I watch Clearcover employees interact. We’re moving in a great direction, and I’m looking forward to seeing our culture evolve in 2019.

The media noticed.

As Clearcover grew, we were featured in both industry journals and major national press outlets. Digital Insurance listed us as one of 26 digital insurance innovators to watch. A top tech consumer reporter, Rich Demuro, featured us in a television spot on KTLA. Then, in October, Clearcover made CNBC’s Upstart 100, a yearly list of promising start-ups (“CNBC unveils its annual list of 100 promising start-ups to watch”). Recently, VentureBeat listed us as a trend-maker in “5 startup trends that shaped the Midwest in 2018”.

Seeing Clearcover get national press has been fun, but we also know press mentions don’t equal success. While it’s rewarding to see the hard work of our team get media attention, there are an abundance of challenges left. We’re building something pretty amazing, and I see our growing presence in the press as validation of the important work we have ahead of us.

I owe my team a lot, and we owe the people who have supported us this year even more.

On to 2019.

2018 has been both exciting and educational. Above all, it’s been the start of a much longer journey. The end of the year is a great time to reflect on what we’ve accomplished, but to also look to the future. I owe my team a lot, and we owe the people who have supported us this year even more. The best way I know to honor all of the help and opportunities we’ve been given is to take this moment to be thankful—then get back to work and make 2019 an even bigger year.

So, to the Clearcover team, to our friends and partners, to all the customers who took a chance on us, and to everyone else that helped make Clearcover happen in 2018, thank you. Here’s to an incredible new year.