Founded in April 2009 by David Cho and former Gawker editors Choire Sicha and Alex Balk out of Sicha's East Village apartment after being laid off by the pop culture magazine Radar, the trio decided to launch their own blog, completely "out of pocket with a bare-bones site." The site's name was coined by contributor Tom Scocca, after the small pointed tool used for piercing holes. "He’d always wanted to have a newspaper named The Awl. So we semi bought it from him in a friendly arrangement," Sicha told Vanity Fair.
On the site's launch, The Awl's About us page asked readers, “What if there were a website that zippily surveyed a wealth of resonant, weird, important, frightening, amusing bits of news and ideas? And what if it weren’t totally clogged with reality show linkbait?” The first posts on the site were an infographic by Emily Gould of Gawker’s office seating chart, "a video of a Miss USA contestant responding to a gay marriage question from Perez Hilton, and an item linking to a Reuters article about physicist Stephen Hawking being taken to the hospital." Initial expectations by media observers were for the site to be a carbon copy of Gawker, but "instead it was something smaller and focused on the writing, where people can write about the stuff they’re passionate or super nerdy about," says Nieman Journalism Lab’s Justin Ellis.
The Awl Network currently employs 13 people, as well as many freelance contributors. The current editors are Matt Buchanan and John Herrman. It was published by John Shankman from 2011 until May 2014 and is now published by Michael Macher. In 2011, David Cho left the Awl to join ESPN-affiliated sports site Grantland. The Awl has four sister sites: Splitsider, a comedy website; The Hairpin, a site geared toward women; The Wirecutter, a consumer electronics blog; The Sweethome, a home furnishings review site; and The Billfold, a blog with a focus on personal finances; Laura Olin edits The Awl's newsletter entitled Everything Changes. Buchanan and Herrman also launched a podcast for the site. The site also launched an app on the Apple Store called The Awl: Weekend Companion.