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Dec 15, 2023

This week, Rob and Lee welcome back Kyle Nakatsuji, the insightful CEO and Co-founder of Clearcover Insurance. Kicking off with some football banter, Kyle shares some great life lessons drawn from his playing days. Exploring more of the “why” behind Clearcover's approach, Kyle discusses the notable changes the company has undergone in recent years. He provides a deeper understanding of the market dynamics and the significance of maintaining boldness and courage, detailing how calculated risks contribute to building something extraordinary in a challenging environment. Then, before the episode comes to a close, there’s a little bit more football talk, of course! 


Learn More:


Kyle: LinkedIn 

Episode 210 with Kyle 

The Farmer from Merna 

Insurance on the Side blog piece 


What You’ll Hear In This Episode:

[7:30] What will it take for Rob and Lee’s wives to listen to this show?

[9:01] Kyle’s backstory playing football in high school and college.

[11:48] Kyle kept on playing football despite a torn ACL, even having surgery after the season.

[14:25] Some of the lessons Kyle learned from his up-and-down journey in football.

[18:58] How the last 18 months have been challenging for entrepreneurs, particularly in the insurance industry.

[20:26] How has Clearcover felt this impact?

[24:18] Taking bold risks in a challenging market and making adjustments to adapt to changing market conditions.

[25:02] Balancing risk and caution.

[27:39] Some of the cool things coming out of this time for Kyle and Clearcover, include a partnership with Experian.

[29:30] What we can learn from a story about Jeff Bezos requesting the light bulbs get taken out of vending machines.

[30:48] Kyle goes more in-depth about his belief that embedded is not a channel, but a strategy.

[41:54] AI’s impact on how the industry will change, will still be driven by the behavioral needs of buyers.

[45:13] Clearcover’s approach to claims from a customer and cost perspective.

[49:11] Why bundling is important.

[51:19] Finding the right combination of convenience, value, and affordability in insurance, particularly in a tricky market like California.

[54:29] Kyle dishes on Aaron Rodgers!