on an interesting side-project on behalf of American Family Ventures . “ I heard that Derek was working on a project that they were calling insurance as a service ,” Nakatsuji told the Let ’ s Grab Coffee podcast in 2021 . “ It was basically an idea around our initial thesis on distribution , which is that you can integrate insurance into some other product or experience and it will be more convenient for the customer and cheaper to distribute . “ I went to my boss and asked if I could spend 20 % of my time hanging out with Derek and his crew , and seeing what they ’ re up to , because we were investing a lot along those lines . I just started showing up to Derek ’ s meetings . I only realised around a year ago that I never asked Derek for permission – I just started going to his meetings !”
The pair worked on the idea for a few weeks before recognising that they needed to create a new company . After some initial scepticism from seasoned investors at American Family Ventures , they eventually persuaded the firm to back their new startup . It was the first vote of confidence in a company which , under Nakatsuji ’ s leadership , has smashed through four separate funding rounds and raised more than US $ 300mn in backing along the way .
The most recent , a US $ 200mn Series D raise in April 2021 , left Clearcover with a valuation of US $ 1bn . For his part , Nakatsuji has been named a Top CEO by Comparably and featured in publications like Forbes and WSJ . In his free time , he enjoys playing golf and spending time with his wife , daughter , and dog Otis .
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