

Reasonably Happy with Paul Ollinger
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.
Episodes
Mentioned books

Mar 3, 2025 • 59min
Gretchen Rubin: Happiness Hacks | Reasonably Happy
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

Feb 12, 2025 • 54min
Fire Up Your Marriage with Carolyn Sharp | Reasonably Happy
"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

Feb 5, 2025 • 35min
Anthony Scaramucci: Success, Failure & the Paradox of Wealth | Reasonably Happy Podcast
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

Jan 15, 2025 • 57min
Comedian Matt Ruby | Reasonably Happy
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/

Jan 1, 2025 • 57min
Nathan Macintosh | Reasonably Happy
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.

Dec 18, 2024 • 1h 3min
Paul Shaffer | Reasonably Happy
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.

Dec 11, 2024 • 53min
Deepak Chopra & Dr. John Kaag | Reasonably Happy
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/
Click the icon below to listen.

Dec 4, 2024 • 49min
Rickey Smiley: Living with Loss | Reasonably Happy with Paul OIlinger
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...
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Nov 27, 2024 • 56min
Is music meaningless? | Reasonably Happy with Paul Ollinger
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
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Nov 20, 2024 • 56min
Comedian Mandal was theWorst Student Council President | Reasonably Happy with 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
Click the icon below to listen.