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

🎭 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 philosophy on finding joy in a world of chaos, Bruce brings his signature wit, wisdom, and unfiltered Hollywood insider knowledge. Check out Bruce's new book: https://www.amazon.com/Seemed-Like-Bad-Idea-Time/dp/0914091921 Buy 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. 🎙️💡 Buy Paul's Book: https://www.paulollinger.com/the-book Buy Carolyn's Book: https://www.secureconnectionsretreats.com/thebook #RelationshipAdvice #LoveAndIntimacy #MarriageTips #Podcast #CouplesTherapy #EmotionalConnection #HealthyRelationships

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/ Click the icon below to listen.

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. 🎵🎭 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/ Click the icon below to listen.