

Reasonably Happy with Paul Ollinger
Paul Ollinger
Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection. words.paulollinger.com
Episodes
Mentioned books

Jul 6, 2025 • 1h 17min
Weapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger
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". This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Jul 2, 2025 • 50min
How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman)
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.comLearn more about Scott’s academic on his website and his magic and mind-reading on https://www.theamazingdrscott.show/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Jun 30, 2025 • 45min
Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger
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/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Jun 18, 2025 • 59min
Jeffery Toobin on Presidential Power | Reasonably Happy Podcast
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=enCheck out Jeffery's book: https://www.simonandschuster.com/books/The-Pardon/Jeffrey-Toobin/9781668084946 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Jun 11, 2025 • 51min
A Poet’s Wild Past w/ Edward Hirsch
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=enCheck 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Jun 5, 2025 • 53min
Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger
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 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

May 30, 2025 • 45min
Facing Down Trump with Jocelyn Benson
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 is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

May 23, 2025 • 27min
Paul Wants $$ From Qatar (and other hilarious Substack posts)
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_ollinger00:00 Introduction to the Podcast and Substack02:48 Exploring Qatar's Influence and Ethics06:02 Proposal for a Qatari Comedy Club08:57 Corporate Life Lessons from Dogs12:00 Navigating Career Changes and Authenticity18:11 The Impact of Social Media on Identity23:10 A Humorous Obituary for the Future This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

May 14, 2025 • 56min
From Chaos to Cambridge
Rob Henderson’s dad walked out when Rob was an infant. Not long after, Rob’s drug-addicted mother placed him into the foster care system and a near-constant cycle of neglect and displacement. According to his 2024 book, 'Troubled', Rob lived in nine different foster homes before his 8th birthday. This takes a toll on a kid, as Rob’s memoir reveals. “By the time I was four or five, my emotions had gone underground,” he writes about the self-preservation defense that kicked in amidst the chaos. So, it probably wouldn’t surprise you that Rob was drinking before he was six years old, doing drugs at twelve, getting into fights, committing vandalism, and harboring little hope for a future beyond high school. What will surprise you is that, despite all the trauma, Rob eventually graduated from Yale and earned a PhD from University of Cambridge. Yes, that Cambridge—the one in England.Subscribe to Paul's Substack here: http://words.paulollinger.comFollow Rob Henderson on Substack here: https://substack.com/@robkhenderson/likes This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

18 snips
May 14, 2025 • 56min
From Chaos to Cambridge - Rob Henderson
Rob Henderson, author of 'Troubled: A Memoir of Foster Care, Family, and Social Class', shares his remarkable journey from a turbulent childhood in foster care to earning a PhD at Cambridge. He discusses the impact of instability on his education and emotional health, reflecting on military discipline as a transformative force. The conversation explores his concept of 'luxury beliefs' and how elite values can disadvantage the less privileged. Rob also delves into the importance of belonging, love, and the lessons learned from his past.


