Founded in 2009, The Awl — whose name refers to a pointed tool used for punching small holes — has been independently owned and operated and did not receive venture capital backing or any outside investment, according to its website. Ownership of each property is distributed among the editors, Mr. Macher said. Historically, he said, each site in the network had only one or two editors.
Silvia Killingsworth, who in 2016 became the editor of The Awl and The Hairpin — a website geared toward women — said that her main job was to discover talented new writers and encourage them to fully embrace their voice and style while writing about a topic that piqued their interest, no matter how obscure it might be.
Over the years, there were viral stories about how to cook a steak and David Foster Wallace’s private self-help library, as well as popular essays providing pointed advice to young people and exploring a writer’s evolving relationship with death.
Many of the writers went on to distinguish themselves. Some, like Vinson Cunningham and Heather Havrilesky, now write for The New Yorker and New York magazine’s website The Cut. One of The Awl’s founders, Choire Sicha, is now the editor of the New York Times Styles section.
“The common thread of all great Awl pieces is that the writing is so indicative of who the writer is and what their interests are,” Ms. Killingsworth said in a telephone interview on Tuesday night. “It’s a place for the writers to just be themselves.”
It helped that many of the website’s loyal readers were themselves powerful media figures who were able to give talented writers their big break. In a lengthy 2015 article about The Awl, The Verge noted that The Awl was profitable, “though with a very thin cushion.”
“The Awl,” Josh Dzieza wrote, “has found a way to make being small work in an industry that favors scale and mass appeal.”
But he went on to add, in a passage that would prove prescient, “The company is subject to the same forces they’ve been warning about, and the people who built it are thinking about how to navigate the weird new internet taking shape.”