In early April, what’s left of the magazine industry gathered at Terminal 5 to see who would win this year’s National Magazine Awards—the ASMEs. Throughout the evening, the usual suspects stepped up to accept their Alexander Calder brass elephants—the ‘Ellies’—on behalf of their teams at The Atlantic, New York Mag, the New York Times Magazine. 

Then came the award for General Excellence, Service and Lifestyle—a category that covers every food, fashion, and fitness magazine in the business. And the Ellie went to… content juggernaut Highsnobiety—a sneaker blog turned cool kid media amalgam that encompasses a twice-annual $20-per-issue print magazine, plus a flood of social media, a website that is also an e-commerce platform, and a creative agency that does 360-degree marketing and storytelling for brands.

Before the crowd could start scratching their graying heads, a Billie Eilish lookalike in a gray Thom Brown skirt-and-pant suit took the dais. There were plenty of people in that room who had never given Highsnobiety much, if any, thought. 

But in that moment, this woman, Willa Bennett, Highsnobiety’s thirty-year-old editor-in-chief, had officially become a force to be reckoned with. Not only that, but HighSnobiety’s business model, which bends rules that had long been sacrosanct in magazine journalism, suddenly appeared to have won the seal of approval from the oldest of the old guard.  

The post at Highsnobiety was a major leap for Willa. Just two years ago, she was the social media manager at GQ. Our friends who worked with her there tell us they thought of her as “the industry’s little sister”—hungry, passionate, and looking to translate the magic of magazines to a new generation. 

They said that even though she’s disrupting the magazine as we once knew it, at heart Bennet is a “a magazine junkie who really venerates [revels in? rellishes?] the old ways.” 

And now the surprise win has put her in the spotlight of the establishment media, with the New York Times Styles running a portrait of Bennett in her signature suit and tie look on its cover. 

The win inspired a segment on the Slate Culture Gabfest in which the hosts pondered, “What Is a Magazine Now?” Over in Spreadlandia, we thought, why not turn that question directly to Willa Bennett herself? 

In the end, this conversation left us feeling more optimistic than usual about the future of media. It also made us feel old as shit. We hope you enjoy it as much as we did.