Lemonade Exposed. Eight Months In.

We’ve learned so much in the eight months since our launch. We got some stuff wrong, iterated and improved, and hopefully we got some things right as well. Since then, things have gone a little nuts.


California, We’re Here.

For a tech company, launching in the tech capital of the world is a huge thing. For an insurance company, launching the two largest economies in the US within a matter of months, is unheard of.

(605) 237-9165
(281) 609-8249

Illinois, Forget Everything You Know About Insurance!

“When I saw what Lemonade had to offer – no paperwork, immediate claim payment, and far cheaper premiums – the more convinced I am it can transform the entire industry.”

(209) 650-9668


Maybe the simplest productivity trick is to think about our productive hours. Most people are productive between 9-11 AM. That’s it.

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585-866-8795 #life-hacks


It’s not easy being a chatbot. People think I’m not real, and it pains me sometimes to admit my AI has an alter-ego: me! Real Jim steps in on those claims that can’t be instantly paid.

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The Cost Of Our Dishonesty

Trust is a public good- as long as we all contribute to it- we all benefit. But once we stop contributing, the system collapses. Fraud wins.

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#behavioral-econ #life-hacks

Why I Tied My Hands

Knowing you’re not in conflict with your insurer, and that you embellish claims at the expense of a cause you believe in, may change your behavior too, setting off a virtuous cycle.

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#behavioral-econ 5204980452

Saving 80% In 90 Seconds?

Incumbents find the idea of a 560% price gap unsettling. Understandably. I get it. That’s why I’m writing this post.

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