Crazy Money 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

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

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.

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

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

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

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 what today's Democratic Party can learn from the Obama era. With sharp wit and refreshing honesty, Maurer discusses the left’s loss of self-awareness, the problem with orthodoxy, and how free speech is under siege from all sides. If you're tired of political echo chambers and crave a blend of humor and intellect, this one's for you. Get Pauls book! https://www.paulollinger.com/the-book Check out Jeffs Substack: https://substack.com/@imightbewrong

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. They also discuss financial mindset shifts, leadership, and maintaining purpose beyond wealth. If you're looking for motivation, business insights, and a fresh perspective on personal growth, this is a must-watch! Find Anne online: https://www.annemahlum.com/ Check out Pauls book: https://www.paulollinger.com/the-book

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, goal-setting, and how small daily changes can transform your life. Plus, find out Gretchen’s #1 tip for taking control of your phone addiction! Don’t miss this inspiring and thought-provoking conversation! #happy #happiness #author Take the quiz: https://gretchenrubin.com/quiz Buy Paul's book: https://www.paulollinger.com/the-book

"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 create a safe, thriving partnership—whether you’re married, dating, or navigating polyamory. Plus, Paul’s wife Stacey joined for an impromptu session on marriage dynamics! Don't miss this eye-opening conversation packed with relationship advice, practical tips, and humor.

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 lessons he learned from working in the Trump White House, and why failure is essential for success. Plus, hear his thoughts on crypto, navigating controversy, and the surprising place he finds true happiness. Don't miss this raw, thought-provoking conversation packed with insights on business, politics, and personal reinvention! Buy Pauls Book: https://www.paulollinger.com/the-book

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: https://words.paulollinger.com/

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 and Other Things that Piss Me Off" https://www.amazon.com/Reasonably-Hap... Read Paul's Substack: https://words.paulollinger.com/

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 conversation is a must-watch for music and comedy fans alike.

Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside award winning author, professor, writer and speaker Dr, John Kaag. Visit Rebind at https://s.rebind.ai/0PmPOV and use the promo code reasonablyhappy to get 15% off your first Rebind book experience Get Paul's book Here: "Reasonably Happy: Essays on Money, Work and Other Things that Piss Me Off" https://www.amazon.com/Reasonably-Happy-Essays-Money-Things/dp/0997270659 Read Paul's Substack: https://words.paulollinger.com/

Paul sits down with comedian and syndicated radio legend Rickey Smiley and talk about happiness in the face of grief after losing a son to opioid addiction, surviving being shot at point blank range and continuing a life in comedy in the face of tragedy. Check out Rickeys book: "Sideshow: Living with Loss and Moving Forward with Faith" https://www.amazon.com/Sideshow-Livin...

Paul is joined by SNL music director Eli Brueggemann to discuss everything from what landing a gig like Saturday Night Live does for a musician to how quickly a masters level university degree can become outdated because of simple technology. Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

Paul sits down with the insanely funny comedian Mandal to discuss his rise, fall and rise again that lead him to be a go to opener for John Mulaney and performing at the world famous Hollywood Bowl. Paul and Mandel dive into the world of stand up comedy and how Mandel finds purpose and happiness and why it is the driving force in all of his artistic endeavors. Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger

Paul sits down with lawyer turned comedian Liz Glazer to discuss how a successful lawyer and law professor can find happiness by saying goodbye to a tenured career by pursuing a life in the arts. Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger