142: Building Canada's Largest Snowboarding Brand at 24 with Perry Gladstone

“I want to know what I'm capable of… but I'm not an adrenaline junkie. I just want to know how far I can take it—because I want to know what my greatest potential is.” – Perry Gladstone At 8, Perry was selling comic books at flea markets. At 15, he opened a skateboard shop that pulled in $100K that summer. By 24, he launched a snowboard company in his kitchen that became Canada’s biggest—& sold it before he turned 30. But it was never about the money. For Perry, business has always been about access—to adventure, freedom, & experiences no one else would hand him. If he wanted to do something, he built a way to do it. That’s how he became a record-setting free diver, a coach to high-powered CEOs, a musician, & a master at intentional reinvention. The common thread? Radical self-awareness. He knows exactly what drives him—& he helps others find the emotional through-line that connects everything they’ve ever done. What Perry builds isn’t just business. It’s identity. It’s legacy. To learn more, find him at PerryGladstone.com. Poet Rainer Maria Rilke said, “The only journey is the one within.” Perry’s been on that journey all along.