Reasonably Happy with Paul Ollinger

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 it. With wit, warmth, and some surprisingly deep evolutionary psychology, Andrew explains how our ancient brains are wired to seek belonging—even if that means choosing teams over Truth. They cover everything from Dunbar’s number to the loneliness epidemic, from the comedy club to Capitol Hilll, and why political identity has become a poor substitute for real community. Whether you're center-left, center-right, or just tired of the noise, this conversation offers a refreshing dose of nuance, laughs, and insight into how we got here and where we could go. If you've ever felt politically homeless—or curious why shouting on Twitter feels like the new religion, this conversation is for you! Don’t miss the part where Andrew suggests that Paul change the name of his podcast to “Drinking Liberal Tears with Paul.” (It’s not going to happen, but just think of how popular it would be if we did!) Subscribe to Paul’s Substack: http://words.paulollinger.com Follow Andrew at https://mightyheaton.com/  Click the icon below to listen.

This week, Paul sits down with Sarah Personette, CEO of Puck, the fast-growing news outlet the New York Times described as “Vanity Fair for the Substack era.” From her ambition to become a CEO at age seven to her senior roles at Facebook, Universal-McCann, and Twitter – which ended after Elon Musk bought the company, Sarah unpacks what it takes to lead teams through uncertainty, disruption, and reinvention. She explains Puck’s blend of high-caliber journalism with modern distribution, and how to survive the oncoming AI onslaught. Sarah speaks candidly about navigating career transitions, modeling work-life balance, leading global teams, and raising children with intention while running billion-dollar operations. Whether you're a founder, a parent, or just starting out, her mantra—“Stay calm, stay focused, stay classy”—is a playbook for thriving in today’s chaotic world. It’s a raw, funny, deeply human look at the future of media, work, and purpose-driven leadership. Also, don’t miss Paul gushing with ‘80s nostalgia about the movie About Last Night starring Demi Moore and Rob Lowe. (Don’t worry - it’s relevant) Learn more about Puck here: https://puck.news/ Subscribe to Paul’s Substack here: http://words.paulollinger.com Watch About Last Night: https://www.amazon.com/About-Last-Night-Rob-Lowe/dp/B000I8HIM2

Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who discovered himself after years of addiction and psychedelics only to emerge on the other side as one of the funniest comedians working today and starring in the hit Off Broadway Steven Soderbergh show "The Fears".

Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize Your Full Potential. Scott’s writing dives deep into the psychology of the victim mindset, narcissism, and the impact of performative vulnerability on social media. Having overcome childhood misdiagnoses that placed him in special ed classes and bullying peers, Scott went on to earn a PhD from Yale. He shares this deeply personal story of as a teachable moment to discuss mental health, cancel culture, psychological flexibility, and what truly helps us grow as humans. Thought-provoking, funny, and brutally honest—this is a must-watch for anyone navigating identity, trauma, or the modern self-help world. Scott’s other books include Transcend: The New Science of Self-Actualization and Choose Growth: A Workbook for Transcending Trauma, Fear, and Self-Doubt. Read Paul’s Substack here: http://words.PaulOllinger.com Learn more about Scott’s academic on his website and his magic and mind-reading on https://www.theamazingdrscott.show/

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/

CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of American presidents. From Trump’s transactional pardons to the controversial case of Hunter Biden, Toobin offers sharp analysis, historical insight, and headline-worthy commentary. He discusses why Gerald Ford’s Nixon pardon was unnecessary, how the January 6th pardons expose Trump’s political strategy, and why public cynicism is fueled by elite immunity. Plus, Toobin opens up about his career, love for golf, admiration for Jim Gaffigan, and his obsession with Evel Knievel’s wardrobe. This episode delivers sharp wit, surprising revelations, and crucial context for anyone interested in politics, justice, or power. Follow Paul: https://www.instagram.com/paul_ollinger/?hl=en Check out Jeffery's book: https://www.simonandschuster.com/books/The-Pardon/Jeffrey-Toobin/9781668084946

Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A Stand-Up Comedy and a Skokie Elegy. Hirsch reflects on his chaotic upbringing in 1950s Jewish Chicago, his complicated relationships with his parents, and the wild characters who shaped his life. He opens up about the tragic loss of his son Gabriel, how grief became poetry, and why humor and heartbreak often walk hand in hand. From poetic craft and emotional truth to the role of art in a distracted world, this is a raw, funny, and deeply moving conversation about identity, creativity, and resilience. Follow Paul on Instagram: https://www.instagram.com/paul_ollinger/?hl=en Check out "My Childhood" in Pieces: https://edwardhirsch.com/ Audio excerpted with permission of Penguin Random House Audio from MY CHILDHOOD IN PIECES by Edward Hirsch, read by the author. © Edward Hirsch ℗ 2025 Penguin Random House, LLC. All rights reserved.

Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing policy scholar—explains why race-based affirmative action has failed America's working class and what can be done to fix it. A self-described “liberal maverick,” Kahlenberg dives into his controversial role in the Supreme Court case against Harvard, arguing that socioeconomic-based admissions would promote both racial equity and fairness without alienating the working-class voters Democrats are rapidly losing. From Harvard's legacy advantages and billionaire endowments to MLK’s and RFK’s forgotten views on class over race, this episode challenges elite institutions, political orthodoxy, and the future of education in America. Check out al of Richard's books and appearances: https://www.richardkahlenberg.org/ Get Paul's book: https://www.paulollinger.com/the-book

In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this week's Reasonably Happy podcast, Benson--who is now running for governor--joins Paul Ollinger to discuss how she modernized the DMV, what it feels like to be targeted by the President of the United States, and why the Democrats' murky future. Paul pushes her to take a stand against a party that keeps falling on the sword of cultural issues with which most of America disagrees, opening the door for the very President who tried to intimidate her. Unfortunately, Benson waffles on subjects like biological males in girls' sports and the fact that most college campuses have been captured by progressive ideology. Still, it's an interesting conversation with a rising political star who, if she can stand up to her party the way she stood up to Trump, could be a solid mainstream candidate someday.Read Paul's Substack here: Http://words.paulollinger.com

This week, Paul reads his three most recent Substack posts, including: A very funny take on Qatar's bribery of pretty much every institution in America, How his dog's feel about castration, and Why many of us will have our TikTok handles on our tombstones. Please join Paul's Substack family by following here: http://words.paulollinger.com . And, if you're so inclined, follow him on Instagram: https://www.instagram.com/paul_ollinger 00:00 Introduction to the Podcast and Substack 02:48 Exploring Qatar's Influence and Ethics 06:02 Proposal for a Qatari Comedy Club 08:57 Corporate Life Lessons from Dogs 12:00 Navigating Career Changes and Authenticity 18:11 The Impact of Social Media on Identity 23:10 A Humorous Obituary for the Future