At his old gig, Jordan Roschwalb wore one pin every day. Working in operations for Mercedes-Benz, he slipped an official brand pin though the lapel of his suit each morning. It was a good one, from Tiffany, but it was more a signifier of stagnation than a beloved item. “After a while, it was like, ‘Why can’t I wear this vintage Mercedes car pin instead?’” he asks. “‘Why am I being sucked into this hole of having to do the same thing over and over again?’”

Now, things are different. In April 2014, after parting ways with Mercedes, Roschwalb founded Pintrill along with his girlfriend Doni and friend Andrew. He’s making his own pins, and wearing whichever ones he wants, whenever he wants. A step forward, no doubt, but the shift from autos to accessories wasn’t exactly smooth sailing at first.

“I always wanted to work for myself,” Roschwalb explains in his Brooklyn office space. “But I needed an exit strategy, and I had no idea what that was.” Looking around the room at the two thousand or so new and vintage pins strewn across the table, tacked into cork boards, and filling storage containers, it’s clear he’s found it. But it took a few months, a couple of false starts, and one fateful trip from his native NYC to Los Angeles to make it happen.

“I packed a bag, went to LA, and met with a friend who has an accessories company,” says Roschwalb. “We went to lunch, and he showed up with Scott Disick. It was just like, ‘OK, this is so weird.’” It was also illuminating. “It made me realize that sort of thing isn’t impossible.” Feeling emboldened by the encounter and the prospect of limitless possibilities, Roschwalb told his buddy he should introduce pins to his accessories line.