Back when Carrier Management first interviewed InsurTech Founder Scott Walchek about his company Trōv, the serial entrepreneur was involved in the second iteration of Trov’s business model—as a provider of on-demand microduration insurance policies.

For a lot of reasons, that business never took off as anticipated.

These days, Trov’s insurance technology—think APIs and software—is dedicated to the B2B2C world of embedded insurance (invisible insurance, software-as-a-service. Take your pick on the name you like).

In a captivating interview with CM Editor Mark Hollmer recently, Walchek candidly explained how his company went from here to there. “All of these pivots I talk about now are obvious, in hindsight,” Walchek says early in the interview.

Our take: There’s nothing obvious at all here, but a lot of great takeaways for tech startups in the insurance space—many about the people who join the building effort along the way.

Here are some of our favorites takeaways (with minute markers to guide your viewing of the video at the top of this article):

[13.55] “We started to hire a lot of insurance people. It was counter-cultural for us because we thought we were doing a great job just asking, ‘Why? Why? Why?’….That’s something we should have done sooner [to discover] what were the real things we should be measuring.”

[15.30] “Never judge success by the number of people [employed]. If I could be radically profitable and growing, and I have three people instead or 300, wouldn’t that be a better success?”

[21.55] To make embedded insurance work, “there’s a bridge that’s required. Many capacity providers don’t have the ability to connect in the ways that digital consumer brands are looking for….We’re that technology bridge that encodes their products and then delivers them to the digital consumer brands.

[23.20] “Consumer brands, neo banks are starving for ways to offer new digital products with high-margin recurring revenue to their customers. Insurance is the perfect way to do that.”

[23.45]”Literally, you have to take the structure down to its studs. You’ve got to rebuild the company.”

[25.30] “From 2018-2021, there were a lot of decisions we had to make. Difficult ones…You grow a company around a certain proposition. You grab a bunch of people who are inspired by it, motivated by it, and then you change. By default, you’re going to lose a bunch of those folks. We had to go through that.”

Hollmer’s related article, “Trov’s Evolution: From Barbra Streisand to Embedded Insurance,” provides more depth about the Trov’s journey from cataloguer of treasures to B2C on-demand insurer of single items to the B2B2C world of embedded insurance. (Barbra Streisand ????)