What happens when the people you’ve spent years working alongside suddenly aren’t there anymore? For Kyle Olson—writer, podcaster, audio dramatist, and inveterate storyteller—grief arrived not as a single storm, but as a pair of Thursdays. This week, Kyle shares the sudden losses of two important figures in his life and reflects on what it means to grieve not just family, but work kin: the people who see us at our most capable, our most frustrated, our most ourselves.

Along the way, we dig into the odd rigidity of American funerals, the messy unpredictability of grief, and the surprising ways death has crept into Kyle’s creative work without him even noticing. From the origins of The Swashbuckling Ladies Debate Society to a poignant headstone he’s been quietly carrying in his pocket since he was 16, this episode explores the legacy we build not through accolades or architecture, but through the lives we touch—and the stories we keep telling.

There’s a moment in every western where a lone figure walks into a dusty town. They are anonymous—neither good nor evil, simply unknown. They solve a problem, provoke a conflict, heal a wound, and just as quickly, disappear.

What if legacy isn’t about how long you stay, but how fully you show up?

This week on Headstone, Pete Wright invites his long-time friend and co-host Seth Nelson into a very different kind of conversation—one not about legal advice or custody battles, but about the invisible residue we leave behind in the lives we touch.

Seth is a divorce attorney by trade, a poker player by instinct, and, perhaps most profoundly, a student of legacy by experience. His story meanders through the Cayman Islands, across card tables and courtrooms, through loss and love, always circling one question: How do we know we mattered?

We follow Seth from his teenage soccer match in Costa Rica to his mother’s groundbreaking civil rights career, to coffee service in bed—a ritual so small and ordinary that it becomes, in time, sacred. Along the way, we confront the false promises of performative legacy: buildings named, awards given, eulogies delivered. And in their place, we find something quieter, something harder to quantify: a client’s peace, a child’s smile, a son’s reflection.

Seth doesn’t stay in his clients’ lives. He isn’t supposed to. But he shows up when it counts. And then he leaves, leaving something behind.

Because maybe the measure of a legacy isn’t in what people remember. It’s in what they feel, long after they forget your name.

🪦 Links & Notes

• How to Split a Toaster – Pete and Seth’s other podcast
• Learn more about Headstone

In 1888, Alfred Nobel read his own obituary. A clerical error, yes—but also a mirror, a reckoning, a chance to see what his legacy might become. The Merchant of Death is Dead, the headline read. It haunted him. It changed him.

Most of us—thankfully—don’t get that kind of theatrical heads-up. But the question still lingers: How will we be remembered? And maybe more urgently, how do we live a life that’s worth remembering?

In this debut episode of Headstone, I'm sitting down with Carrie Fox—founder, CEO, strategic communicator, values-driven entrepreneur, mother, author, and accidental interior design intern at fourteen—to explore what it means to live a life that leaves an imprint. Not one carved in marble but etched into the people we love, the work we do, and the conversations we choose to have (even the awkward ones).

There’s a paradox at the heart of Carrie’s life: She’s a professional communicator who argues that what matters most… isn’t what you say. It’s what you do. More Than Words. It's a mantra. A methodology. A quiet rebellion against empty mission statements and the tyranny of the polished brand.

We trace a winding path—from sixth-grade dances and dollar-bribed rejections, to the legacy of difficult fathers, to the tender, often invisible labor of parenting with intention. There’s a surf lesson in Puerto Rico. A Mount Rushmore of unexpected mentors. A surprising origin story involving Cal Ripken Jr., a spontaneous freelance gig, and origination of the birthquake.

But beneath all of that—the stories, the jobs, the titles—there’s a deeper question humming: What does it mean to live in a way that your children will recognize later? That your colleagues will remember? Carrie’s life isn’t a monument. It’s a mosaic. And maybe that’s the point. Because legacy isn’t so much about what we leave behind. It’s how we show up while we’re still here.

Links Mentioned:

• Learn more about Carrie Fox and Mission Partners
• Carrie’s weekly series: Finding The Words
• Subscribe to Mission Forward with Carrie Fox

Before the granite. Before the eulogy. Before someone says your name for the last time.

Headstone is a podcast about legacy—not just the kind carved into stone, but the kind we leave in the lives we touch, the stories we tell, and the memories others carry forward. In this trailer, host Pete Wright shares the haunting idea that inspired the show: the three deaths we all experience, and why the final one is the most human of all. Each episode, Pete invites a guest to explore what it means to live a meaningful life—and, eventually, to answer one deceptively simple question: What do you want on your headstone?

Subscribe now and join the conversation. Because a well-lived life deserves a great last line.