I had an interesting discussion a couple of years ago with an InsurTech entrepreneur about the nature of funding. His thoughts were that you can either look to major investment as the means to be the number one in a space (see Ebay, AirBnB, etc. to appreciate the importance of this), or can be more incremental in your approach if yours is a more disruptive play that might get undermined by incumbents if it threatens them...
“In less than three years, Lemonade has expanded across the US, given back to dozens of charities chosen by our community, and fundamentally changed how a new generation of consumers interacts with insurance,” said Daniel Schreiber, Chief Executive Officer and cofounder, Lemonade. “Looking forward, we aspire to create the 21st century incarnation of the successful insurance company: a loved global brand that can endure for generations; an organization built on a digital substrate, enabling ever faster and more efficient operations, and ever more delighted consumers.” This significant funding round comes off the back of an active year for InsurTech investment. Analysts at Deutsche Bank found recently that volumes had increased by more than 60% between 2017 and 2018.
https://www.reinsurancene.ws/insurtech-lemonade-secures-300-million-in-latest-funding-round/