Reasonably Happy with Paul Ollinger

Updated: 26 Mar 2025 • 275 episodes
paulollinger.com

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.

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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 jou

61 min
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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 l

69 min
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🎭 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 encounter

50 min
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Paul Ollinger & Gretchen Rubin 03 Mar 2025 • EN

Gretchen Rubin

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 ins

58 min
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12 Feb 2025 • EN

Carolyn Sharp

"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,

54 min
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Paul Ollinger & Anthony Scaramucci 05 Feb 2025 • EN

Anthony Scaramucci

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, weal

35 min
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