Driven to Fail Podcast #6: From The Onion to Road & Track

If a dream job ends too early, is it still a dream? How would you feel if you had to rebuild your life from one of those ends . . . twice?

Earlier this year, Hagerty launched a new podcast, Driven to Fail. The show is about what happens when things go wrong—what we do when life falls apart, and what we learn by trying to put it back together. Each episode is an hour, give or take, a candid conversation with a single guest.

I’m Sam Smith, the host. You can read more about the show here.

Episode 6 begins streaming today. Our guest is John Krewson—a founding editor at comedy landmark The Onion and a former senior editor at Road & Track.

Krewson was on staff at The Onion from 1991 to 2012. In that span, he and a passel of friends grew the brand from a weekly small-town newspaper to an internationally beloved website and one of the most important voices in comedy.

A book Krewson coauthored, Our Dumb Century, was a number-one New York Times bestseller, winning the James Thurber prize for American Humor. Chris Farley crashed his wedding. Aziz Ansari and Ellie Kemper were office interns. An Emmy-winning writer for Rick and Morty and Community called John “probably the most talented writer I’ve ever worked with.”

Then, after 20 years, he left it all to work at a car magazine.

Krewson left The Onion by choice, part of a mass and reluctant staff exodus in the wake of short-sighted management decisions. An office full of people raised money and fought like hell to preserve an institution they loved, but in the end, they lost, so they left, and the brand’s cultural influence shrank to a fraction of what it had been.

Still, John stayed optimistic. He landed at Jalopnik, then Road & Track, helping reboot and reimagine the latter in a period of award-winning change. Later, in a heartbreaking series of events, he lost his father, his long-time girlfriend, and his job in a matter of months. The years that followed—beset with depression, more loss, and more struggle—were anything but easy.

Almost a decade later, John has started over again, and he’s in a much better place. He’s now a sought-after freelance editor and writer, helping shape TV shows and the journalism of places like Cycle World. He’s in demand in no small part because of what he learned when it seemed like nothing would ever work out.

Driven to Fail can be downloaded or streamed wherever you get your podcasts. This link will take you to the show’s Apple page. Its home on Spotify is here.

If faces are more your thing, a video of each episode lives on the Driven to Fail YouTube channel.

If you try our show and like it, please tell your friends. Even better, share a link or leave a positive review. A warm response will help make a second season happen, so hearing from you matters.

Barring all that, drop a line directly: spsmith@hagerty.com. I’d love your thoughts.

Thanks for listening!

Note: This episode was taped last year. The audio introduction describes Krewson as a full-time employee of Cycle World; he has since left that position to focus on TV and writing projects.