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?
08:16 - The paragliding accident that nearly killed him
09:43 - Failing big, more than once
10:29 - Every decision eventually comes down to identity
13:13 - Building the muscle of survival through failure
13:52 - Teenage obsessions: skateboards and the surf culture ideal
16:23 - Becoming friends with Tony Hawk through hardware sales
18:51 - Waking up surrounded by skateboarding legends
19:43 - The transition into snowboarding
21:13 - Sneaking onto mountains before snowboarding was allowed
21:24 - Stacy Peralta's mentorship and life-changing advice
25:00 - Starting Limited Snowboards from nothing
25:51 - Selling the business, losing his marriage, and identity collapse
26:32 - The pro rider scandal that ended his skateboard career
28:45 - "So I guess you're out of the industry" - the comment that cut deep
30:42 - Does he believe in luck?
32:00 - Who are you when the thing that defines you is gone?
33:15 - Disruption and leveraging existing infrastructure
34:15 - Will's "mastery spiral" concept
36:32 - The trap of everyone around you still expecting the old identity
37:11 - The shift into music, guitar, and a record deal
38:02 - Making skateboard videos and shaping "reality" through editing
39:30 - Selling the snowboard company and starting a film company
41:21 - The Israel Global Television Network story
44:22 - An "embarrassment of riches" - doors opening everywhere
45:43 - North Star thinking and the value of the journey
46:24 - Wanting to know what's possible, and how far he can take something
47:01 - What is free diving?
47:54 - Competing in depth, time, and distance
48:15 - His national record: 6 minutes, 1 second
48:41 - The training accident that ended his free diving career
51:18 - Chasing flow state through extreme sports
53:20 - Where he finds flow state now, as a father
55:23 - The identity work he does with elite performers and leaders
58:35 - The real question leaders need to ask themselves
1:00:08 - The "transition trap" explained
1:02:47 - What comes first: knowing the next chapter, or knowing who you are?
1:03:17 - His book: Fast and Hot
1:03:49 - How to connect with Perry
1:04:17 - Who are you now?
1:05:09 - Now working with people who can change history
1:05:49 - Knowing when a risk has gone too far
1:08:00 - Who is he becoming over the next 3-5 years?
1:09:31 - Final reflection: the one question he wishes people asked
1:11:04 - Closing remarks
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Relevant Links For the Viewer and Citations
Website - https://www.willpolston.com
Instagram - https://instagram.com/willpolston
Facebook - https://www.facebook.com/willpolstonmih
LinkedIn - https://www.linkedin.com/in/willpolston/
Twitter / X - https://x.com/willpolston
TikTok - https://www.tiktok.com/@willpolston
Check out Perry's website: https://perrygladstone.com
Get Perry's book, "Fast and Hot: How to Open Hearts, Win Minds, and Create a Better Business and a Better Life"
About Me: I am dedicated to helping individuals and businesses unlock their true potential through expert coaching and training programs. I'm passionate about empowering others to achieve their dreams and live a life they love. Subscribe for more insights and tips on personal development, productivity, and achieving your goals. Let's embark on this journey together!
