Snowboard Brand Owner to Elite Coach: Why High Performers Don't Know Who They Are Without the Title! Trapped in the Transition, Losing Your Edge, Defined by What You've Done? Break the Identity Trap & Build Your Next Version - Perry Gladstone | EP276

Episode Notes

In this episode, I sit down with Perry Gladstone, a serial entrepreneur who built one of Canada's largest snowboard brands, became friends with Tony Hawk through skateboarding, launched a television network in Israel, competed as a national-record-holding free diver, and now coaches elite performers and business leaders through identity transitions. We talk about the belief that's carried him through every reinvention - "I will figure it out when I get there" - and what happens when that belief meets its limits: a paragliding accident that nearly killed him in front of his pregnant wife, a free diving blackout that ended his competitive career, and the collapse of his identity when a scandal ended his skateboarding business overnight. Perry shares his framework for navigating the "transition trap," why every major decision ultimately comes down to identity, and the powerful question he wishes more people asked themselves.

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Video Chapters

00:00 - Introduction

00:05 - Where in the world: Toronto

01:17 - Curiosity from a young age, and the school play story

03:22 - Being a "quick start," not a planner

04:07 - His foundational belief: "I will figure it out when I get there"

04:56 - The origin story: his parents' three different versions of the same event

07:50 - When has "I'll figure it out" not worked?