Quotesmith was comparing insurance prices years before the web arrived. Shopping for life or health insurance once meant meeting an agent who showed you a few policies of the agent's choosing. Quotesmith.com let people compare prices from many insurers on their own, then buy. When it filed to go public in the summer of 1999, insurance looked ripe for the price comparison already reshaping travel and books.

A 1984 Idea, Online

Robert Bland founded the company in 1984 as an insurance price comparison service. The internet brought a new bet: consumers would buy insurance directly once they could see the market for themselves. Consumers were only starting to research big purchases online, so Quotesmith was early. It showed quotes from many insurers. It earned commissions as a licensed broker, and its own staff completed each sale.

Insure.com, Then Life Quotes

Quotesmith priced at $11 a share in August 1999. Its shares fell fast as investors soured on internet companies, and growth came slower than hoped. It bought the Insure.com website in 2001 and later renamed itself after it. In 2009 the company sold the Insure.com and Quotesmith names and became Life Quotes, Inc. Bland led the company through every stage. It went private in 2010.

Cover: The Blacksmith, Eugène Delacroix. Art Institute of Chicago, public domain. Chosen for a blacksmith at the anvil (Quotesmith).