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