drugstore.com wanted to move the corner pharmacy online, from vitamins and shampoo to prescriptions, all delivered to the door. Famous investors backed it, including Amazon. Former Microsoft executive Peter Neupert ran it. When it filed to go public in the summer of 1999, online retail was the market's favorite story. Drugstore goods seemed perfect for the web, because people buy them again and again.

Rite Aid and Repeat Buyers

drugstore.com bet that the drugstore, with its frequent, routine purchases, would move online once ordering got easy. Customers would save trips and gain privacy. drugstore.com would win loyal repeat buyers. It formed a partnership with Rite Aid to handle prescriptions. It spent heavily on marketing to build its brand fast. Amazon, an early investor, was a close partner in its first years.

Walgreens Buys, Then Closes

drugstore.com priced at $18 a share in July 1999. It lost large sums for years, because shipping low-priced goods cost so much. Over time it focused on beauty and health products, bought Beauty.com, and reached hundreds of millions of dollars in yearly sales. In 2011 Walgreens bought the company for about $409 million. Five years later, in 2016, Walgreens shut the site down.

Cover: S. P. Peck Apothecary, Unknown. Art Institute of Chicago, public domain. Chosen for an old apothecary storefront.