RHS 096 – Kyle Nakatsuji Explains Why Clearcover is Positioned to Win

by | April 8, 2021



In this episode of The Ryan Hanley Show, Kyle Nakatsuji, Founder and CEO of Clearcover, joins the show to breakdown why he started Clearcover and why his unique perspective on the industry forced him to create an auto insurance carrier of the future. Kyle gets it, and you MUST listen to this episode…

Episode Highlights:

  • Kyle shares how he got started as a venture investor. (13:17) 
  • Kyle shares how the idea of curiosity plays a significant role in being successful. (18:46)
  • Kyle explains why he started a company in this particular area of insurance. (23:32)
  • Kyle shares two ways to improve retention as an insurance company. (28:42)
  • Kyle shares what to consider when building the infrastructure of the organization. (33:19)
  • Where does Kyle see the next generation of carriers? (36:29)
  • Kyle mentions a surprising statistic about personal auto carriers. (36:44)
  • Kyle shares what he’s most excited about. (37:09)
  • Has Kyle started to consider other products? (43:51)

Key Quotes:

  • “As a venture investor, you really get paid to do two things. You get paid to be intellectually curious, and you get paid to sell money, which is a weird thing to do. It’s a weird phrasing, but that’s kind of what you do. ost competitive deals, you’re selling, right?” So you get paid to learn and build ideas and theses, and then sell money.” – Kyle Nakatsuji
  • “When you start learning about something, you rapidly climb up and you think you know a ton about it. And, then the more time you actually spend with a topic, you kind of fall off this cliff of stupidity.” – Kyle Nakatsuji
  • “It’s not that these carriers don’t see the opportunity, or they don’t want to help…But, the opportunity has to be of a certain size to warrant the kind of investment, to turn a ship that big…And, with some with newer carriers like us, we’re just more free to experiment. There’s much lower overhead to do interesting and innovative things with our partners.” – Kyle Nakatsuji

Resources Mentioned:

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