Americans had clipped coupons from the Sunday paper for generations. CoolSavings, based in Chicago, moved the coupon online. Members signed up, browsed offers from brands and stores by category, and printed coupons at home. Advertisers paid CoolSavings for each shopper who saw or used an offer. The company went public in May 2000, just after internet stocks had begun to fall from their peak.

Every Coupon Has a Name

CoolSavings bet that coupons would be a strong lure for online shoppers and a precise tool for advertisers. Members registered, so the company knew who was using each offer. Their profiles let it target offers by place and interest. That made it more valuable to brands than a scattered newspaper insert. The model depended on online advertising budgets, and those budgets shrank sharply after 2000.

Rescued, Renamed, Sold

CoolSavings priced its IPO at $7 a share in May 2000 and listed on Nasdaq. The dot-com crash cut its advertising revenue. Starting in 2001, loans and investment from the media firm Landmark Communications kept it afloat, and Landmark took control. The company moved into broader online marketing and renamed itself Q Interactive. In 2008 Landmark sold Q Interactive to Intrepid Investments, a merchant bank based in the U.S. Virgin Islands.

Cover: Icebound, John Henry Twachtman. Art Institute of Chicago, public domain. Chosen for ice and winter (cool).