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

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.

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.

In this premiere episode of Headstone, I sit down with Derek Brandow, an instructor at University of Oregon’s School of Journalism and Communication, to explore the delicate balance between performance and authenticity. 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