Perry Gladstone on his father - He Was Enough

Who We Remember

We ask each of our guests a simple yet profound question: "Whose life story from your own family would you most want to have documented on film?" and "How does your family's story shape your own personal and professional legacy?"
Today's guest: Perry Gladstone, Coach and Strategic Advisor at Perry Gladstone Consulting

Perry's pick: His father, Al Gladstone

Sound Bites

- "It wasn’t about the flea market. It wasn’t about buying and selling things. It was just a way for him to connect with people."

- "He spent the rest of his life making up for leaving me. What I would’ve wanted most is for him to know—he did enough."

- "Being who you are is enough. And it’s what the world really needs."

Summary
In this deeply personal episode of Who We Remember, Perry Gladstone opens the door to his father’s remarkable, complex life. Al Gladstone was a community builder, a cultural torchbearer, and the driving force behind a folk dance movement that swept across Canada in the 1960s and ‘70s. Through flea markets, garage sales, and global adventures, Perry’s father cultivated human connection as both craft and necessity.

Yet behind the joy and charisma lay a story shaped by intergenerational trauma and a lifelong search for safety. Perry reflects on how his father’s choices, passions, and fears shaped his own path—from action sports and film to his current calling as a thinking partner for extraordinary people in transition. What emerges is a meditation on legacy, identity, and the longing to tell someone, finally and fully: You did enough. This episode is a love letter, not just from a son to his father, but from one generation to the next.

About Perry
Perry Gladstone is a confidential advisor and thinking partner to exceptional leaders—entrepreneurs, athletes, artists, and changemakers—who are ready to reconnect with the core truth that has quietly powered them since childhood. Known for his clarity, courage, and refusal to be driven by applause or title, Perry helps his clients align their lives with who they truly are, not what the world expects of them.

Before becoming a trusted guide for others, Perry lived many lives of his own. He built Canada’s largest snowboard brand, produced radio, film, and television, saved lives in Costa Rica, and authored a book on creating a better life in business. He’s surfed, flown off mountains, and jumped up and down with a guitar in front of crowds—all in pursuit of experience, connection, and meaning.

His coaching practice, now over fifteen years strong, was born from a profound personal shift—one catalyzed by a near-death blackout while freediving 120 feet underwater. That moment changed everything, launching Perry into deeper work with people in transition: those seeking purpose, legacy, and freedom.

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Visit us at storykeep.com/podcast to learn more about how StoryKeep is preserving family histories. Subscribe on your favorite platform to catch new episodes released bi-weekly, available in both audio and video formats.

Join me, Jamie Yuenger, as we go on a journey of remembrance and discovery, celebrating the stories of those we cherish. Don’t miss our enriching journey—subscribe today and be part of "Who We Remember."
Credits
Produced by Jamie Yuenger and Piet Hurkmans. Our show’s musical intro and outro is taken from the track “Thursday” by the independent artist Nick Takénobu Ogawa. You can listen and support his music on bandcamp here