MAILCHAMP
IT’S A BEAUTIFUL DAY IN HIS NEIGHBORHOOD, AND BEN CHESTNUT IS THINKING ABOUT PAIN. LATE-AFTERNOON SUN IS SHINING on Atlanta’s BeltLine, an abandoned train track converted into a green pedestrian path. Children cluster at a cart selling small-batch raspberry-lime Popsicles. Commuters swarm past on bikes and boards and feet, the city’s gleaming towers at a picturesque remove. And Chestnut, a slim and sober presence in near-monochrome navy beneath his mop of black hair, is contemplating a bicycle.
“You start a company, and then you wake up one day and realize you don’t remember what any of your hobbies are,” says Chestnut, 43, the co-founder and CEO of MailChimp. “It gets scary when you don’t really understand what it is that you like.”
He’s had some time to figure that out recently. MailChimp, which spent the first half of its life figuring out what exactly it could do well—which turned out to be handling companies’ email marketing—today is one of the most successful small businesses in America. Except it hasn’t been small for a while, not with more than 700 employees and 16 million customers and 14,000 more signing up every single day.
Chestnut, who’s watched his company grow “from startup to grownup” with a parent’s mixed emotions, has some free time now that he’s no longer always worrying about survival. His father recently reminded him he was once a good cyclist, so now Chestnut has a group of mountain biking friends, a Peloton at home, and a Strava addiction. He has a couple of weekend racecars, too, to go with the Tesla he drives to work.
Tonight, he’s riding a cheap, lightweight company bike that someone at MailChimp, in-house quirk firmly in place, has named the Batmobile. It’s somewhat apt: Take away his quick and slightly goofy grin, his ready embrace of the absurd, and what one employee calls “the Mister Rogers look,” and Chestnut sometimes seems like he could outbrood Bruce Wayne.
“People will ask me, ‘Your business is doing so well. Aren’t you happy?’ No. I’m in pain,” he says. “But that’s how you know you’re growing.”
IT’S AN EXCELLENT PROBLEM to have, of course—one Chestnut and his co-founder, chief customer officer Dan Kurzius, have learned to embrace over the almost 18 years that they’ve devoted