
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.
Latest episodes

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

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

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_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

May 14, 2025 • 56min
From Chaos to Cambridge - Rob Henderson
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 groundbreaking concept of “luxury beliefs”—status-signaling values held by the privileged that often harm the poor. This conversation is raw, eye-opening, and packed with insights about resilience, class, and what truly shapes success.
Check out Rob's Substack: https://www.robkhenderson.com/
Read Paul's Subtack: http://words.paulollinger.com
Follow Paul on Instagram: https://www.instagram.com/paul_ollinger

May 7, 2025 • 58min
Mike Reiss: How The Simpsons Changed TV | Reasonably Happy with Paul Ollinger
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’ room was like a "kibbutz but more Jewish." It’s a deep dive into comedy, creativity, and the wild ride of creating a global phenomenon.
Follow Mike's Substack: https://substack.com/@mikereiss
Get Paul's Book: https://www.paulollinger.com/the-book

Apr 30, 2025 • 45min
Laurie Woolever- Dark Side of Celebrity Chefs
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 telling personal stories—alongside hot takes on The Bear, Lucky Charms, and how Batali allegedly didn't pay staff. This is a must-watch for anyone fascinated by the dark underbelly of fame, food, and finding your voice after chaos.
Check out Laurie's podcast: https://www.instagram.com/carbfacepod/
Get a copy of Paul's book: https://www.paulollinger.com/the-book

Apr 23, 2025 • 48min
E.A. Hanks - Famous Father, Troubled Mother
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 distance, the collapse of her mother’s mental health, and how writing became both her refuge and rebellion. If you're into celebrity legacies, healing childhood wounds, or the grind of making it as a writer in L.A., this episode hits every note.

Apr 16, 2025 • 1h 11min
Jim Lampley- Boxing, Fame & Fallout | Reasonably Happy with Paul Ollinger
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 George Mira to being thrust into the spotlight by Roone Arledge, Jim discusses ego, failure, reinvention, and finding happiness through storytelling. His new memoir It Happened: A Uniquely Lucky Life in Sports is a masterclass in perseverance and passion—this conversation is a must-watch for sports fans, storytellers, and anyone chasing purpose.
Get Jim's Book: https://www.simonandschuster.com/books/It-Happened!/Art-Chansky/9781637746431
Get Paul's Book: https://www.paulollinger.com/the-book

Apr 9, 2025 • 52min
Jane Borden- Cults Like Us | Reasonably Happy
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 far right and far left are vulnerable to cultish thinking. With dark humor, candid insights, and a deep dive into American history, this episode is a must-watch for anyone curious about religion, politics, and the future of democracy.
Check out Janes book: https://www.simonandschuster.com/books/Cults-Like-Us/Jane-Borden/9781668007808
Get Pauls Book: https://www.paulollinger.com/the-book

Apr 2, 2025 • 52min
Life at Fox News w/ Jessica Tarlov | Reasonably Happy with Paul Ollinger
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, anti-Semitism on the left, and what’s really holding back immigration reform. It’s an honest, thoughtful, and funny episode that blends politics with real life.
Get Pauls book: https://www.paulollinger.com/the-book