“They said, ‘We get 1000s of applicants every year, [but] you’re the only person that’s ever called us.’ And I knew that I was onto something.”
Stern returned to law school energized with experience doing legal research and reviewing contracts for a high-profile sports team, sure he wanted to continue that path and work for a sports organization after graduation.
After doing another summer with the Raiders and then articling at a labor and employment boutique in Ottawa, Stern rejected the traditional advice to gain a few years of experience as an associate before going in-house. Instead, he made another fateful cold call.
This time, his call was to the general counsel of Maple Leaf Sports & Entertainment, Robin Brudner. Brudner told him he would have to get several years’ experience at a Bay Street law firm to join her team. But she also gave him some unconventional advice.
“You’re obviously very good at sales, and you love sports,” Stern recalls Brudner saying. “Why don’t you work in sports, forget sports law for a second, [and] take a chance [by learning] the industry from the inside.”