Scott McKenna

Building the next-gen insurance brand

About

5 x Founder | Insurance, Venture Incubation, Brand + Digital, Retail, Talent Management, Partnerships I have been building brands and businesses for leading creators, entrepreneurs and founders for 10+ years. I love to bring ideas to life. Started my first company when I was 23. Started another 4 since.

Links

NY Times

Hypesight | Talent Management Agency

Badges

Tastemaker

Gone streaking

Maker History

careless™Instant, pay monthly cover for modern humans
May 2026

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Joined Product HuntMay 13th, 2026

Forums

p/careless

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2mo ago

Who has had a bad experience getting or claiming from Insurance?

We'd love to hear it. We are always trying to understand how we can build the best experience possible.

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2mo ago

careless™ - Instant, pay monthly cover for modern humans

The hassle-free, instant insurance app for modern humans and digital tribes. Pay monthly, cancel anytime. Insurance membership on your terms. You love it? We cover it, in minutes*.