insurance-comparison
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Progressive Insurance
Progressive became an insurance giant by doing something that sounds commercially reckless: making prices easier to compare. Behind Flo and the blue lettering sits a disciplined machine for pricing risk, distributing through both screens and independent agents, and turning insurance from a mystery into a shopping decision.
Catch
Catch is a benefits platform built for the more than 50 million Americans who work for themselves and have no employer to hand them a health plan. It helps freelancers, contractors, gig workers and solopreneurs find, compare and enroll in health, dental and vision insurance, applying tax credits instantly so coverage costs less. The service is free to users. Founded in 2019 as a Y Combinator startup, Catch raised about $20M, was wound down by its original founders in early 2023, then bought and relaunched the same year by two operators who personally believed independent workers deserved a real safety net.