People who bought their own health insurance had few easy ways to compare plans until eHealth put them side by side. Its site, eHealthInsurance.com, showed plans from many insurers, so individuals, families and small businesses could weigh prices and coverage before buying. Insurers paid eHealth commissions on each sale. When it went public in 2006, most Americans still got their insurance through work.

A Broker in Every State

eHealth started in 1997 with a bet that buying health insurance, a confusing and paper-heavy process, could work like other online shopping. It became a licensed broker in every state and built tools to quote and apply for plans online. Most of its customers bought insurance for themselves, such as the self-employed. Insurers paid it commissions for each policy, the same way they paid traditional agents.

The Medicare Turn

eHealth priced its IPO at $14 a share in October 2006 on the Nasdaq. The Affordable Care Act and its public exchanges later changed the individual market. eHealth turned toward Medicare plans for older Americans. That business grew quickly as baby boomers aged into the program, and it became most of eHealth's revenue. Rising marketing costs and changing commissions made profits uneven. eHealth remains publicly traded.

Cover: Lovers Beneath an Umbrella in the Snow, Suzuki Harunobu. Art Institute of Chicago, public domain. Chosen for lovers under an umbrella (coverage and protection).