Back when DailyCandy was a profitable newsletter business spewing daily beauty tips and entertainment news to young urban women, a pair of new University of Pennsylvania grads decided to start a DailyCandy for dudes. They called it Thrillist. Launched in 2005, the city guide built its following on irreverent twentysomethings who played and shopped much like its founders, Ben Lerer and Adam Rich.
Today, DailyCandy is dead. In late March parent company NBCUniversal announced plans to close it because it couldn’t attract enough of an audience to be profitable. In contrast, Thrillist has grown into a mini-media empire, spawning two additional websites and an e-commerce company that together saw revenues jump 53% last year, to $85 million. Advisers are urging the pair, now 32 and 34, to consider taking it public — a show of confidence in their decision to sell things rather than rely heavily on advertising.
As the company’s cub-faced and charismatic CEO, Lerer believes that Thrillist offers a model for a new type of hybrid media company. The son of Huffington Post co-founder Ken Lerer, he has had a deep look at the art of digital-media business models. In 2010 the pair founded Lerer Ventures, which makes seed investments in companies such as BuzzFeed, NowThisNews, and PandoDaily. The fund has shaped his perspective on the strengths and limitations of media titles that depend on advertising. “How do you build a billion-dollar media company?” he asks, pacing through Thrillist’s lofty New York offices. “You need to own your biggest advertiser.”
For a media company, Thrillist’s audience isn’t huge. Roughly 9 million people visit its sites monthly; two-thirds of them subscribe to a newsletter about food, drink, and events in one of 25 cities. But in 2010, Thrillist acquired JackThreads, a tiny men’s fashion e-commerce company that it soon integrated with its other media properties, adding a “Shop” tab on Thrillist.com and its brother site, Supercompressor. Thrillist now pulls in 20% of its revenue from digital advertising; the rest comes from e-commerce.
In 2012, JackThreads began designing clothes in-house. Its six private-label brands include Goodale, a casual brand that resembles a tech startup uniform (jeans, T‑shirts), Hillsboro shoes (the “Lerer” is a suede wingtip sneaker), and Crosby & Ross suiting. Thrillist relies on data it collects from readers to evaluate products. It then markets those products to readers through advertiser-created content embedded in its newsletters. “We’ve gotten really good at making a reader into a shopper and a shopper into a reader,” Lerer says.
In recent years, several e-commerce companies have sought to use original content to attract new customers, with mixed results. Thrillist succeeds because the content drives the commerce, Altimeter analyst Rebecca Lieb says. Or as Lerer would say, it’s a media company first.
This story is from the April 28, 2014 issue of Fortune.