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PODCAST

Reasonably Happy with Paul Ollinger

Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.

business philosophy

All Episodes

50:45

A Poet’s Wild Past w/ Edward Hirsch

Reasonably Happy with Paul Ollinger ·

2025/06/11

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

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53:12

Affirmative Action FAILED? | Richard Kahlenberg &...

Reasonably Happy with Paul Ollinger ·

2025/06/05

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

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45:15

Facing Down Trump with Jocelyn Benson

Reasonably Happy with Paul Ollinger ·

2025/05/29

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

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26:54

Paul Wants $$ From Qatar (and other hilarious...

Reasonably Happy with Paul Ollinger ·

2025/05/23

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

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55:31

From Chaos to Cambridge - Rob Henderson

Reasonably Happy with Paul Ollinger ·

2025/05/14

He was drinking by age five, shuffled through ten foster homes, and emotionally shut down by the time most kids are starting kindergarten — yet Rob Henderson clawed his way from chaos to Cambridge.In this powerful episode, Rob, author of Troubled: A Memoir of Foster Care, Family, and Social Class, shares his incredible journey from trauma and addiction to earning a PhD from Cambridge University. He opens up about childhood instability, military discipline, elite university culture, and his

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57:39

Mike Reiss: How The Simpsons Changed TV | Reasonably...

Reasonably Happy with Paul Ollinger ·

2025/05/07

The Simpsons writer and showrunner Mike Reiss shares behind-the-scenes secrets from 36+ years on the iconic animated series. From working with comedy legends like Sam Simon, Al Jean, and Conan O'Brien to writing for Johnny Carson and witnessing the wild beginnings of FOX, Mike recounts hilarious Hollywood stories and life lessons from his travels to 147 countries. He reveals the origin of the Simpsons, why Harvard wasn’t funny, how VCRs and fan feedback helped shape the show, and why the writers’

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45:07

Laurie Woolever- Dark Side of Celebrity Chefs

Reasonably Happy with Paul Ollinger ·

2025/04/30

Former personal assistant to both Anthony Bourdain and Mario Batali, Laurie Woolever, opens up about the untold truths behind celebrity kitchens, toxic food culture, addiction, and what ultimately drove Bourdain to suicide. From Mario Batali’s manipulative power plays to Bourdain’s romantic obsessions and lifelong depression, Woolever shares the unfiltered story behind her new memoir Care and Feeding. The conversation also explores alcoholism in fine dining, working through shame, and the ethics of

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47:48

E.A. Hanks - Famous Father, Troubled Mother

Reasonably Happy with Paul Ollinger ·

2025/04/23

In this raw and revealing episode of Reasonably Happy, author and screenwriter E.A. Hanks opens up about growing up as the daughter of Tom Hanks, surviving a chaotic childhood with an abusive, mentally ill mother, and forging her own path in Hollywood. From hidden trauma and therapy breakthroughs to the price of fame and writing a memoir about family, identity, and the open road, Hanks shares powerful stories behind her new book The Ten. She discusses how her father’s fame created emotional

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71:20

Jim Lampley- Boxing, Fame & Fallout | Reasonably...

Reasonably Happy with Paul Ollinger ·

2025/04/16

Legendary sportscaster Jim Lampley joins Paul Ollinger on "Reasonably Happy" to share unforgettable stories from his 40+ year broadcasting career, covering everything from Olympic Games and Super Bowls to boxing icons like Muhammad Ali and Mike Tyson. Lampley reveals the behind-the-scenes drama of his rise at ABC Sports, recounts his emotional connection to the Miracle on Ice, and reflects on the values learned from greats like Billie Jean King, Arthur Ashe, and Howard Cosell. From interviewing

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51:59

Jane Borden- Cults Like Us | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2025/04/09

In this thought-provoking episode of Reasonably Happy, Paul Ollinger sits down with journalist and author Jane Borden to unpack her explosive new book Cults Like Us: Why Doomsday Thinking Drives America. Together, they explore how apocalyptic beliefs, religious extremism, and cult-like behaviors have shaped American identity—from Puritan roots to modern political movements like MAGA. Jane reveals how tribal psychology, anti-intellectualism, and the prosperity gospel fuel division, and why both the

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52:16

Life at Fox News w/ Jessica Tarlov | Reasonably...

Reasonably Happy with Paul Ollinger ·

2025/04/02

In this episode of Reasonably Happy, Paul Ollinger sits down with Fox News contributor and Raging Moderates co-host Jessica Tarlov for a wide-ranging conversation on politics, media bias, Israel, parenting, and the chaos of air travel. Jessica opens up about raising two young kids, finding peace in Jamaica, and holding her own as the lone Democrat on The Five. They dive into the latest national security scandal involving leaked attack plans, the challenge of moderate voices in polarized media,

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61:04

Too Woke to Joke | Reasonably Happy Podcast

Reasonably Happy with Paul Ollinger ·

2025/03/26

In this episode of Reasonably Happy, comedian and writer Paul Ollinger sits down with former Last Week Tonight writer Jeff Maurer for a razor-sharp, no-holds-barred conversation on comedy, politics, and the state of liberal discourse. Maurer, now the voice behind the acclaimed Substack I Might Be Wrong, unpacks his journey from speechwriter to Emmy-winning TV writer, and why he left Hollywood to pursue independent commentary. They dive deep into the culture wars, media bias, the Biden dilemma, and

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69:47

From $0 to $100,000,000: How Anne Mahlum Built a...

Reasonably Happy with Paul Ollinger ·

2025/03/19

In this episode of Reasonably Happy, host Paul Ollinger sits down with Anne Mahlum, entrepreneur, philanthropist, and founder of Solidcore, the Pilates chain she sold for $100 million. Anne shares her incredible journey from starting a nonprofit running club for the homeless to building a fitness empire with over 100 locations. She dives into overcoming personal and business challenges, navigating the pandemic, redefining success, and the importance of pushing past comfort zones to embrace growth

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50:22

Bruce Vilanch: Hollywood Stories | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2025/03/12

🎭 Hollywood stories, comedy legends, and the pursuit of happiness! 🎭In this episode of Reasonably Happy, host Paul Ollinger sits down with the legendary Bruce Vilanch—Emmy-winning writer, comedian, and one of the funniest minds behind Hollywood’s biggest events. Bruce spills the tea on outrageous celebrity encounters, wild award show moments, working with Joan Rivers, and the unpredictability of writing for some of the craziest actors in showbiz. From behind-the-scenes gossip to his personal

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58:33

Gretchen Rubin: Happiness Hacks | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2025/03/03

Bestselling author Gretchen Rubin joins Reasonably Happy with host Paul Ollinger for a deep dive into happiness, self-improvement, and personal growth. They explore habit formation, the psychology of motivation, the power of self-awareness, and why enjoying the process matters more than the outcome. Gretchen shares insights from The Happiness Project, her Four Tendencies personality framework, and her experiment with learning to love the New York Knicks. They also discuss money and happiness,

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54:17

Fire Up Your Marriage with Carolyn Sharp | Reasonably...

Reasonably Happy with Paul Ollinger ·

2025/02/12

"Love isn't enough." So says marriage expert Carolyn Sharp in her new book 'Fired Up: Four Secrets to Reigniting Intimacy and Joy in Your Relationship.' Paul talked with Carolyn (a college friend) this week and dove deep into the challenges of modern relationships, the importance of emotional connection, communication, and radical acceptance, and why love alone isn’t enough to sustain a lasting partnership. Carolyn shares insights on attachment styles, overcoming relationship roadblocks, and how to

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35:16

Anthony Scaramucci: Success, Failure & the Paradox of...

Reasonably Happy with Paul Ollinger ·

2025/02/05

In this candid and insightful episode of Reasonably Happy, host Paul Ollinger sits down with Anthony Scaramucci—founder of SkyBridge Capital, former White House Communications Director, and author of From Wall Street to the White House and Back. Scaramucci shares unfiltered lessons on entrepreneurship, resilience, wealth, and personal growth, reflecting on his meteoric rise in finance, public failures, and what truly makes a fulfilling life. He dives into the paradox of money and happiness, the

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56:53

Matt Ruby | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2025/01/15

Join Paul as he sits with the very funny Matt Ruby and discuss performing on psychedelic mushrooms, being raised by a bohemian mom who ran around New York City with Alan Ginsberg and more!Links to all things Matt Ruby including his newsletter, specials and more: https://www.mattrubycomedy.com/ Get Paul Ollinger's book Here: "Reasonably Happy: Essays on Money, Work and Other Things that Piss Me Off" https://www.amazon.com/Reasonably-Hap... Read Paul's Substack:

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57:09

Nathan Macintosh | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2025/01/01

Join hilarious comedian and hater of all things technology Nathan Macintosh as he sits with host Paul Ollinger and discusses his love hate for tech, the overabundance of screens in socoiety and the fear of what AI will do to the world. Watch Nathan's latest 2 specials here: "Money Never Wakes" https://www.youtube.com/watch?v=sQd7kHYiNsQ&t=20s&authuser=1 "Down with Tech" https://www.youtube.com/watch?v=gApnofHJLoo&authuser=1 Get Paul Ollinger's book Here: "Reasonably Happy: Essays on Money, Work

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62:43

Paul Shaffer | Reasonably Happy

Reasonably Happy with Paul Ollinger ·

2024/12/18

Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from his childhood in Thunder Bay to iconic roles on Saturday Night Live and The Blues Brothers. Shaffer sits with host Paul Ollinger and reflects on his early love for music, working alongside comedy greats like Martin Short and Bill Murray, and how rock and roll’s raw simplicity shaped his passion. Packed with nostalgic Hollywood and Broadway stories, this

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307 results

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