Beginning their third article in a series examining the statutory financial results of InsurTech carriers Lemonade, Root and Metromile, authors Matteo Carbone and Adrian Jones make reference to the “Cliffs of Insanity.”

Titled “He’s gaining on us? Inconceivable! The Second Quarter in InsurTech Startup Financials,” the phrasing is a nod to a scene from the movie “The Princess Bride,” in which a masked man in black follows Vizzini and his accomplices across the sea and up the Cliffs of Insanity.

After the mighty giant Fezzik embarks on the climb with Vizzini, Inigo Montoya and a kidnapped princess hanging from him, the masked man catches up to the group and starts climbing the same rope beneath them.

“He’s gaining on us,” says Montoya, watching the masked man climb the rope. “Inconceivable,” says Vizzini, angrily rebuking the giant for failing to live up to his legendary reputation.

“You keep using that word. I don’t think you know what it means,” says Montoya.

Carbone and Jones draw a parallel to battle between the lumbering incumbents in the insurance industry—powerful giants who started their climb ahead of their antagonists but who are slowed by their sheer size.

Carrier Management republished a version of the LinkedIn article on its website in several parts:

  • ‘He’s Gaining on Us?’ An ‘Inconceivable’ Quarter of InsurTech Carrier Financials (
  • Congratulations! You’re Innovating in a Highly Regulated Industry (
  • Second-Quarter 2018 Financial Details for Lemonade, Root and Metromile (

Earlier in the year, Carrier Management also republished versions of articles the two have written about 2017 and first-quarter 2018 financials for the three venture-backed InsurTechs:

Topics Carriers InsurTech Tech