car-insurance
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Roojai Put the Insurance Office in Your Pocket - Then Bought the Underwriter
Roojai began by making Thai car insurance easier to buy online. A decade later, it owns the underwriting stack, serves hundreds of thousands of customers and is testing whether a digital insurer can feel more human when the road gets messy.
No Gecko, No Jingle: The Second-Chance Car Insurer Run From a Chicago Suburb
Founded in 1959 and still run by the Parrillo family, Safeway Insurance built a business worth hundreds of millions on the drivers big-name carriers pass over - sold through local agents, priced to be affordable, and advertised almost not at all.
GEICO
The company that skipped the insurance agent, hired a British-accented lizard, and turned '15 minutes' into one of the most repeated sentences in American advertising.
Art Agrawal
Art Agrawal (full name Abhas 'Art' Agrawal) is a serial entrepreneur and Co-Founder & CEO of Jerry (jerry.ai), an AI-powered car ownership super app based in Palo Alto, California. A TechCrunch Disrupt 2012 winner with his prior startup YourMechanic, Art has spent over a decade attacking the friction-laden world of car ownership - from on-demand repairs to insurance comparison and auto loan refinancing. Jerry has raised $330M+, reached profitability in 2024, and serves over 4 million customers, saving them an average of $800/year on car insurance.