Chris Schembra: The Strange Mercy of a Good Middle

May 23, 2026

Gratitude entrepreneur Chris Schembra built a movement on a single dinner-table question, but before the pasta and the big stages there was a kid in an isolation room, four tattoos marking four hard years, and a long road through recovery. In the season one finale of Headstone, Chris turns his famous question back on Pete, and the conversation becomes a meditation on connection, mortality, and what it means to give people permission to be themselves.

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This is a show about legacy, memory, and the stories we hope will outlive us.
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A well-lived life deserves a great last line.

Headstone is a podcast about legacy—not the kind etched in marble, but the kind we carry in memory, in laughter, in the stories we tell long after someone’s gone.

 

Hosted by Pete Wright, Headstone begins with one deceptively simple question: What do you want on your headstone? From there, we explore the lives behind our legacies.

 

In each episode, we reflect on meaning, mortality, creativity, failure, grief, and joy—finding humor and humanity in the messy middle of it all. It’s not a show about death. It’s a show about life—and the words we hope will outlast us. Because sometimes, the story that survives you… is the best one you ever told.

Pete Wright

Portland, OR
Pete Wright is a veteran broadcaster and media consultant with a 30-year career spanning journalism, brand storytelling, and podcasting. He is a co-founder of TruStory FM, where he hosts and produces podcasts that blend education, entertainment, and human-centered communication.

Chris Schembra: The Strange Mercy of a Good Middle

May 23, 2026

Gratitude entrepreneur Chris Schembra built a movement on a single dinner-table question, but before the pasta and the big stages there was a kid in an isolation room, four tattoos marking four hard years, and a long road through recovery. In the season one finale of Headstone, Chris turns his famous question back on Pete, and the conversation becomes a meditation on connection, mortality, and what it means to give people permission to be themselves.

Listen Now »

Dr. Nachi Felt: Always Becoming

November 29, 2025

A psychologist who once went by Michael reclaims his true name — and with it, the story of who he’s becoming. In this conversation, Dr. Nachi Felt opens up about identity, faith, mortality, and the lifelong practice of learning to love the person you evolve into.

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James Ochoa: The Storm Chaser

November 1, 2025

James Ochoa has spent a lifetime steering into the storms most of us would avoid. In this conversation, he and Pete explore how a life built around helping others survive chaos can become its own quiet form of grace.

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The Generous Goodbye with Aliza Kline

October 11, 2025

Aliza Kline has spent her life building communities that help people find belonging—from the living waters of ritual to the warmth of a Friday night table. But when the work no longer needs her, she discovers that legacy isn’t what you leave behind—it’s what you let keep growing without you.

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A Large Collection of Tiny Brief Encounters with Seth Nelson, Esq

August 2, 2025

When divorce attorney Seth Nelson steps out of the courtroom and into a conversation about legacy, what emerges is a moving portrait of a life measured not by victories, but by presence. In this episode, Seth and Pete explore the quiet weight we leave behind in the lives we pass through—and why that might be the most enduring legacy of all.

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