Craig’s List is classified ads on the Internet. Their strategy includes crisp decisions like valuing consistent user experience more than great design (the website looks like it’s from 1995, because it is), and user-accessibility over monetization (“Craigslist president Jim Buckmaster has stated that creating a superior user experience is more important to the company than making money [ source]”). The strategy is clear and differentiated, which should be seen as a strength, but it has bothered pundits for twenty-five years, who have therefore predicted its demise: “The main obstacle to sustainability and growth at Craigslist is likely the company’s and its founder’s strong principles valuing customer-offering over monetization, trusting consistency over innovation. Although admirable in many ways, the issue is that without innovation, the company’s customer-offering will soon no longer be strong enough to stay relevant, undermining its very well-intended purpose.”⁠— HBS. But crisp decisions make for a great strategy, even if controversial. Despite that well-reasoned death-sentence from HBS, despite others pointing out that dozens of successful companies have made sections of Craig’s List theoretically obsolete, despite data that predicts Craig’s List “demise”, despite protestations that Craig’s List could be a “gold mine of revenue, if only it would abandon its communist manifesto,” (i.e. if only it would abandon its strategy), it continues to be one of the most-visited sites in America, with revenues of $1,000,000,000 in 2020 with a staff of just fifty people, even after twenty-five years of Internet evolution.

Jason Cohen • A Smart Bear » What makes a strategy great