When InsurTech entrepreneurs like Assaf Wand, Max Simkoff and Dan Preston set out on the path of bringing groundbreaking ideas to life in the insurance industry, they heard a lot of negative talk about hurdles they couldn’t climb.

Executive Summary

Tuning out the naysayers, leaders of three InsurTechs with close to $1 billion valuations said that being able to learn from one another has been a key part of the recipe for climbing to unicorn status during a webinar hosted by InsurTech NY, an organization whose mission involves building a community for InsurTechs, as well as improving access to investment, infrastructure and talent.

But equipped with “positive naivety” in the words of Simkoff, and the help of a few people willing to take bets on them and their ideas, the founders of InsurTech startups said they also turn to each other to figure out the answers together.

During a recent InsurTech NY webinar titled “How to Become an InsurTech Unicorn,” these three chief executive officers of companies that have almost achieved the milestone $1 billion valuation status talked about how they got to where they are and the ways they have bonded to leap over obstacles that include regulation and reinsurance—and initially, just to combat any seeds of self-doubt that early naysayers tried to plant in their minds. (Editor’s Note: Wand’s Hippo has achieved a $1 billion valuation; Simkoff’s States Title and Preston’s Metromile have not yet.)

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