LookSmart was started by a husband-and-wife pair of McKinsey consultants in Melbourne, with money from Reader's Digest. Evan Thornley and Tracey Ellery built a web directory where human editors sorted sites into neat categories, so people could browse to an answer. The San Francisco company licensed its directory to portals, most importantly Microsoft's MSN. When it listed on Nasdaq in August 1999, search engines still returned messy results, and a hand-built map of the web looked like a lasting advantage.

Reader's Digest for the Web

Thornley and Ellery began the business in Melbourne as Homebase, with Reader's Digest as the majority owner. When Reader's Digest wanted to shut it down, the founders arranged a cheaper buyout, and Reader's Digest kept a small stake. LookSmart's editors reviewed sites and filed them under topics. The company earned money from ads and from licensing the directory to other sites. Its deal with MSN put LookSmart results in front of millions of people.

Losing Microsoft

LookSmart priced its IPO at $12 a share in August 1999 and raised $92.4 million. The stock climbed above $70 in early 2000. Then the crash hit, and Google's automated search made hand-built directories look slow. Thornley stepped down as chief executive in 2002 and later entered politics in Australia. Microsoft ended its MSN contract in 2003, and LookSmart lost much of its revenue. It left Nasdaq in 2015 and stopped filing with the SEC in 2017.

Cover: Looking out of Bass Cove, No. 238, Henry Hamilton Bennett. Art Institute of Chicago, public domain. Chosen for looking out over a cove (Look).