A note before we begin: this is not a new conversation. It's the first one.

Before Headstone had a single episode in the feed, I needed to know whether the question at the center of this show—what do you want on your headstone?—could actually carry a conversation. So Derek Brandow, an instructor at the University of Oregon's School of Journalism and Communication, offered the most generous thing a guest can offer: himself, live, in front of his own class, with a room full of students watching the machine work. No safety net, no prior interviews to learn from, no idea yet what this show would become. This was the test. Everything since was built on it.

Now, with a new group of interviews on the way, it felt right to bring this one back as a warm-up—a reminder of where the show started, and a chance to hear the question asked for the very first time.

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We often think of confidence as a gift—something innate, something you either have or you don't. But what if it's not? What if confidence is, instead, a performance? A mask we wear to navigate the world, to protect ourselves from the fear of rejection, to shield us from a deeper truth: that we're terrified of not belonging.

Derek's journey is a case study in transformation. Raised in an atmosphere of insecurity and shame, he spent years performing his way through life—loud, funny, athletic—all to hide deeper vulnerabilities. But then, thanks to an unexpected catalyst, he reframed his understanding of vulnerability and connection.

Derek's story is about how we, as humans, crave belonging and how that craving shapes the way we present ourselves to the world. Whether it's his work teaching "confidence" to students navigating an increasingly digital and divided world or his reflections on what it means to be truly seen, Derek reveals that the key to connection—and legacy—lies not in what we perform, but in how we listen, how we see others, and how we allow ourselves to be seen.

So join us as we unpack the subtle forces that shape our interactions and discover what it means to leave a legacy not in words but in the courage we inspire in others.

Links & Notes

• Brené Brown's TED Talk, The Power of Vulnerability: Watch it here
• Brené Brown's book, Braving the Wilderness: Find it here

This is the last conversation of my first season, and I almost didn’t finish it.

Chris Schembra came to me the way the best guests do, as a name pressed into my hand by someone I trust. Aliza Kline told me I needed to talk to him, and Aliza is rarely wrong about people. What I didn’t expect was how quickly the conversation would stop being about him.

On paper, Chris is the gratitude guy: the 7:47 dinners, the pasta, the rooms full of leaders he teaches to thank the people they have forgotten to thank. I’m fascinated by the keynote version. And I wanted to talk to the kid underneath it, the one who couldn’t hold onto his own memories, who got marched into the isolation room, who learned early that loss arrives whether or not anyone gives you permission to grieve it. We went there together, and Chris went willingly, all the way down to the tattoos and the rehabs and the version of himself he is still learning to forgive.

And then, somewhere near the end, he did the thing he does to everyone else. He turned the question on me. He asked what was coming up, and I told him about a lost friend, and from there the conversation belonged to both of us.

I sat on this recording for months because I was afraid of that stretch. I am not afraid of it anymore. If you have ever wondered what gratitude actually costs, and what it gives back, this is the one. It lands on a single word, the one Chris wants on his headstone. It’s a good one, and a reminder of what a blessing it is to be alive.

This is the season one finale, finally. I’ll see you back here for more soon.

Links & Notes

• Chris Schembra
• The 7:47 Gratitude Experience / 7:47 Club
• Podcast, Gratitude Through Hard Times
• Books: Gratitude Through Hard Times and Gratitude and Pasta
• The Anatomy of Peace, The Arbinger Institute
• Johann Hari TED talk, “Everything You Think You Know About Addiction Is Wrong”
• Tony Lo Bianco and his one-man Fiorello LaGuardia play, “The Little Flower”
• “Just a Common Soldier (A Soldier Died Today),” poem by A. Lawrence Vaincourt (basis for the Memorial Day 2015 veterans video Chris produced with Lo Bianco)
• Dr. Edward “Ned” Hallowell, ADHD author
• Curb Your Enthusiasm, “Bad Middling”

Sometimes at fifteen, sometimes much later, we finally stop running from ourselves. We sit down and ask the quiet but impossible question: Who do I want to be?

This conversation begins with a name. I first knew him as Michael — the professional veneer that felt safe, pronounceable, uncontroversial. But today he is Nachi, reclaiming the Hebrew name that always held the truer story of identity. That shift, simple on the surface, opens a portal into something tender and universal: how identity is shaped not by the roles we play, but by the courage to show who we really are.

Faith plays a profound role in that evolution. Nachi talks about Judaism not as dogma, but as structure, clarity, and purpose — a lens that helps him understand endings without fear and see value in existence itself. He points out that death, in his tradition, gives life its shape, its urgency, its meaning. Mortality becomes not the enemy but the clarifier.

We talk about rage, comfort, goodness, the pursuit of happiness versus the pursuit of pleasure, and the strange wisdom of a terminally ill teenager named Jonathan who taught Nachi how to be happy. We explore the liminal space between clarity and acceptance — how seeing ourselves honestly requires surrender to the things we cannot control, and gentleness toward the things we can.

This episode is about identity, yes. It’s about faith and behavior and clarity and death. But more than anything, it’s about permission: the permission to evolve, to reclaim ourselves, to choose again and again and again who we are becoming.

This is Headstone with Dr. Nachi Felt.

Some people study chaos because they have to. Others because they can’t look away.

James Ochoa has spent his life inside both camps—born into a noisy, loving, impossibly crowded family, raised amid the unpredictable rhythms of mental illness and grace, and shaped by a series of accidents and near misses that could have ended him. Instead, they gave him a reason to begin again.

For more than three decades, James has been a counselor, teacher, and writer—founder of The Life Empowerment Center in Austin, Texas—helping adults with ADHD navigate the emotional turbulence of their minds. His first book, Focused Forward: Navigating the Storms of Adult ADHD, reframed ADHD as more than a matter of focus and distraction. It was, he argued, a lifelong relationship with uncertainty—an emotional weather system that required compassion as much as strategy.

Now, as he works on his forthcoming book, When the Shiny Wears Off: Navigating the Lifetime Storms of Adult ADHD, James has turned his attention to what comes after the breakthrough. How do you sustain meaning once the novelty of self-discovery fades? What does peace look like for a person whose entire life has been about motion?

Our conversation isn’t about diagnoses or treatments. It’s about the quiet courage of someone who’s spent a lifetime learning not just how to endure the storms of life, but how to find wonder inside them. From the bathtub sanctuary of his childhood to the long, slow work of recovery, James’s story is one of transformation through reflection—proof that even the noisiest lives can contain a deep stillness at their core.

When he talks about mortality, it isn’t abstract. He remembers the hospital bed at four years old, the blue light above him, and the promise he made then: I’m here for a reason. Decades later, he’s still living out that reason—helping others hold on through their own tempests long enough to find meaning in the calm that follows.

Aliza Kline has built her life around connection—the kind that happens when people gather around a table, or descend beneath the surface of the water, or find themselves saying “yes” to something unexpected. For over two decades, she’s created institutions that made those moments possible: Mayyim Hayyim, the reimagined mikveh in Boston, and OneTable, the social platform that’s helped more than a million people share Shabbat dinner. Her work has changed how Jewish ritual lives in the modern world—and how people connect to each other through it.

And now, she’s walked away.

In this conversation, Aliza joins me to explore what it means to build something that doesn’t need you anymore. What does it take to step back when your fingerprints are still visible on the work? How do you trust that the thing you’ve nurtured can keep living without you? We talk about the power of generosity, the practice of grace, and the paradox of legacy: that the things we make to last often outgrow us—and that maybe that’s the point.

From her childhood in Colorado Springs to her leadership in New York, from the living waters of the mikveh to the glow of a Friday night table, Aliza has spent her life creating spaces for people to rediscover belonging. But her real lesson is quieter: that legacy isn’t measured in names or titles, but in the courage to release control—and the faith that meaning will keep flowing, even after you’ve stepped aside.

Links & Notes

• Mayyim Hayyim Living Waters Community Mikveh – The inclusive ritual bath and community center Aliza helped found in Boston.
• OneTable – The social dining platform connecting people through Shabbat dinners.
• Anita Diamant, The Red Tent – The novel and author whose essay inspired the founding of Mayyim Hayyim.
• Mikveh and Jewish Ritual Immersion – Background on the tradition reimagined by Aliza’s work.
• Julianne Holt-Lunstad’s Research on Social Connection – The Brigham Young University psychologist whose work on loneliness shaped OneTable’s impact studies.
• Melissa Kirsch, “Offer Accepted – The New York Times – The essay that connected Aliza’s idea of “on offer” to a wider audience.

Step into Rob Kubasko’s office and you’ll find a reliquary of light and story: Iron Man’s helmet, a model of the USS Enterprise, a Phantom of the Opera music box. To the untrained eye, it’s a collection of toys. To Rob, it’s a theory about how humans work: that play isn’t the opposite of seriousness, it’s the method for reaching it.

This week, Rob opens up about the moments that shaped that worldview—growing up with humor as both a defense and a bridge, standing at the wake of a childhood bully and discovering that even pain can carry the seeds of connection, and navigating a career that carried him from the early days of digital design into the heart of national politics. What emerges is a picture of someone who has spent his life asking: how do we connect? What do we build together? And how do we keep joy alive, even in dark seasons?

Rob talks candidly about the seductions and disillusionments of political life, about what it means to contribute to community now, and about the legacy he hopes to leave in the simple mantra he first taught his daughter on the walk to kindergarten. Turns out, that’s the same inscription he imagines on his headstone, a legacy not of permanence but of presence—an invitation to live joyfully, curiously, and in service to others.

History is often written in bold type. We remember the wars, the inventions, the big cultural shifts that announce themselves with headlines. But Glenn Fleishman has been spending his time reminding us that the things history forgets—scraps of type, obsolete tools, obscure printing processes—are often the very things that shape us the most. They make up the invisible machinery of culture.

Glenn’s career has been built on chasing down these overlooked artifacts and giving them back their dignity. He’s written for the New York Times and The Economist, produced deeply researched books like How Comics Were Madeand Six Centuries of Type and Printing, and helped shepherd ambitious publication projects like Shift Happens, a 700-page cultural history of keyboards. Along the way, he’s become something unusual in the digital age: a historian of tactility, a man who believes that physical impressions—whether pressed into paper or cast in memory—endure in a way pixels never quite can.

In our conversation, Glenn talks about his childhood hours with microfilm readers, his fascination with forgotten crafts, and his frustration at watching knowledge slip away. But what emerges most powerfully is the joy he takes in sharing. Glenn doesn’t guard his discoveries like relics; he builds communities around them, from Kickstarter campaigns to type museums small enough to fit in a breadbox. His chosen epitaph—which you’ll hear—is both pun and philosophy. Our legacies aren’t measured by what we keep, but by what we don’t let ourselves forget to pass on.

Links & Notes

• Six Colors – ‘Help Me, Glenn!’ where Glenn writes regularly about Apple and technology.
• Take Control Books – Glenn has authored many. I don’t know how he stays so far ahead of this stuff.
• How Comics Were Made – (Kickstarter project, now a bookstore edition from Andrews McMeel Publishing under the title How Comics Are Made).
• Six Centuries of Type and Printing – (Kickstarter book).
• Shift Happens – by Marcin Wichary, which Glenn helped bring to life. I haven’t finished because it is… in a word… extraordinarily comprehensive.
• Tiny Type Museum & Time Capsule – Glenn’s Kickstarter project creating a cabinet of printing artifacts.
• Blog (Glog) – Glenn Fleishman interrogates the past — a richly written blog where he explores the history of printing, comics, technology, crowdfunding, and forgotten tools.
• Bluesky
• Mastodon

When Srdjan Injac was a kid, he was small. Picked last for dodgeball small. Picked on. Smacked around. Defended by others on the playground small. He carried a condition called pectus excavatum that made his chest cave inward, and for years he hid it under shirts, and shame, and silence.

Then war broke out in Sarajevo.

What follows is not a tale of overnight triumph, but something far more compelling: a young man who survives four years of war, moves to a country where he barely speaks the language, discovers his own strength—not just physical, but moral—and builds a life centered around helping others feel at home in their own bodies.

In this episode, Srdjan talks about growing up during the Bosnian War, finding strength in the face of disfigurement and displacement, and how the body became his way of healing the mind. He shares how his transformation from bullied to bodybuilder gave way to something even more meaningful: a career built on empathy, discipline, and showing others that strength isn’t just about muscle—it’s about the courage to keep going when everything tells you to stop.

If legacy is what we leave behind, then Srdjan’s is written on every life he’s helped reshape—one rep, one conversation, one small act of belief at a time.

Links & Notes

• Elev8fitness