The first section, titled Then & Now, will highlight the extra challenging year that has been 2023, starting with inactive startups—some as old and unnoticed as ChimpQuote, and others as fresh and irritating as Health IQ and Assurance IQ—both of which tried and failed to offer auto insurance at scale and at a profit. But startups aren’t the only ones to struggle—page 13 looks at Say, Spire, and Verti, which were once backed by incumbents. 

The report moves on to cover noteworthy exits such as those of Metromile, Compare, and Gabi. Most interestingly, Root’s current stock price is closer to what Lemonade’s stock price was in 2021, yet Lemonade’s stock is nowhere near that figure (above $60 per share). Additionally, we’ve gathered exclusive views on the Insurify and MassMutual deal, ending with a highlight of Boost by Experian. 

The second section of the report, titled Money Moves, highlights insurance funding and how 2021 was a golden year for some. However, the harsh reality is that investments have flowed towards Root, Lemonade, Clearcover, Polly, Insurify, and Jerry. It lists insurer-backed car companies. 

The third section, Market Overview, shares trends on car sales, premiums, and more. The good news is that 92% of U.S. households own a car. The bad news is that only a third are easily addressable by insurtechs. All in all, Liberty Mutual, Nationwide, and Lemonade are in the same boat as carriers who didn’t see their car insurance premiums grow in 2023. 

The fourth section, titled The Kayaks of Insurance, is divided into two subsections to differentiate between insurance sold anywhere versus at the point of sale. The section begins with 5Mi and ends with Select highlights, including Credit Karma’s new mission, EverQuote’s milestone, and Jerry’s struggles. 

Finally, we present the 2022 and 2023 DPW of Branch, Clearcover, HiRoad, Just Auto, Lemonade, Loop, Root, Sigo, Tesla, and Toggle, before wrapping up.