Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger

Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger

Author: Paul Ollinger June 30, 2025 Duration: 45:09
Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blackstone founder Stephen A. Schwarzman. Zibby shares how grief, motherhood, October 7th, and why it’s okay–great even–to marry the tennis pro! She shares how resilience shaped her path, from launching a award-winning podcast and starting her own publishing house to writing memoirs and novels. She reflects on growing up in privilege, breaking free from societal expectations, and using her platform to speak out about antisemitism in a world that is increasingly dangerous for Jews. Zibby’s story is a masterclass in reinvention, purpose, and creative freedom.

Read Paul’s Substack: https://words.paulollinger.com/
Learn more about Zibby here - https://www.zibbyowens.com/

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
Stoic Street Smarts w/ Ed Latimore [not-audio_url] [/not-audio_url]

Duration: 1:08:48
Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed…
Soul on Fire w/ John O’Leary (Encore episode) [not-audio_url] [/not-audio_url]

Duration: 52:07
John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really, really burned, over 10…
Why You Will Never Feel Rich w/ Daniel Crosby [not-audio_url] [/not-audio_url]

Duration: 56:27
Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the fun, non-obvious asp…
Why Two Parents Are Better Than One w/ Melissa Kearney (Encore) [not-audio_url] [/not-audio_url]

Duration: 40:55
Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised in two-parent homes…
Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark [not-audio_url] [/not-audio_url]

Duration: 41:15
If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most u…
Laughing at Death w/ John Kenney [not-audio_url] [/not-audio_url]

Duration: 53:15
What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In this episode, I (i.e., me–Paul–the host) sit down with John K…
Rise of Populism w/ Brad Todd [not-audio_url] [/not-audio_url]

Duration: 48:56
Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in American politics. From growing up in East Tennessee to advising s…
From Prison to Oprah [not-audio_url] [/not-audio_url]

Duration: 56:52
What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New York Times bestselling author? In this unforgettable episode,…
Vote for Jesus! w/ Jonathan Rauch [not-audio_url] [/not-audio_url]

Duration: 45:20
What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan Rauch returns to the podcast to talk about his new book 'Cross-P…
Tribalism is Dumb (w/Andrew Heaton) [not-audio_url] [/not-audio_url]

Duration: 1:06:10
Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism comes from, how it is tearing us apart, and how we might fix…