Reasonably Happy with Paul Ollinger

Reasonably Happy with Paul Ollinger

Paul Ollinger

Episodes 317
Avg. Duration 54m
Activity Highly Active
Apple Rating 4.9 (442)
Since Jan 2019
Latest Episode Mar 2026

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Schedule
Weekly
Format
Episodic
Consistency
67%
Hosting
feeds.megaphone.fm

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About This Podcast

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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Recent Episodes

Believe and You Will See! (w/ Nir Eyal )

Mar 12, 2026 58m

My guest this week is Nir Eyal, whose two books ('Hooked’ and ‘Indistractable’) have sold over 1 million copies in over 30 languages. This week he published his latest - Beyond Belief: The…

Gina Gershon on Fame, Desire, and Boobs

Mar 05, 2026 1h 1m

Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing disruptor of polite expectations. You know Gina from…

The Courage to Be Right w/ Matt Kaplan

Feb 26, 2026 59m

Matt Kaplan is a science correspondent at the Economist and author of the new book I Told You So!: Scientists Who Were Ridiculed, Exiled, and Imprisoned for Being Right in which he shares the stories…

Insider Trading w/Tom Hardin

Feb 19, 2026 1h 14m

How do you handle it when you screw up badly? (Like really badly.) Former hedge fund trader and Wharton graduate Tom Hardin was convicted of Securities Fraud and Conspiracy to Commit Securities…

Surviving Middle Age w/ Ben Markovits

Feb 12, 2026 50m

Ben Markovits is the author of several acclaimed novels, including his most recent release The Rest of Our Lives, which explores marriage, infidelity, empty nesting, and mortality. The book, which…

Marriage, Infidelity, and Millennial Disillusionment with Erin Somers

Feb 05, 2026 44m

Erin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicating” and W praised the book for its “sometimes…

A.I. Facts, Fears and Fiction (w/ Bryan Reimer)

Jan 28, 2026 44m

AI will have at least as big an effect on society as the invention of electricity. That’s the prediction of MIT’s Bryan Reimer. Bryan is the co-author of the new book ‘How to Make AI Useful’ in which…

From Apartheid to Atlanta w/ Robyn Curnow

Jan 15, 2026 1h 2m

My guest is Robyn Curnow, a native South African who spent over two decades at CNN, where she hosted CNN’s Newsroom, and anchored The International Desk with Robyn Curnow. Prior to that, she served…

Rewrite Mental Illness w/Laura Delano

Jan 07, 2026 1h 14m

Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which was not something openly discussed at the…

Find your Essential Intent w/ Greg McKeown

Dec 18, 2025 1h 26m

Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions for 2026, Greg’s insights will be a…

High Net Worth Divorce with Laura Wasser

Dec 03, 2025 40m

People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like Angelina Jolie, Kim…

Surviving the College Application Process w/ Jeffrey Selingo

Nov 19, 2025 57m

As the father of two prep school students, I was very eager to meet this week’s guest. Jeffrey Selingo has written about college admissions for more than 25 years and is a New York Times bestselling…

Paul’s Insights into NYC, Email, and Estate Planning

Nov 12, 2025 44m

Hello friends. On this week’s episode, I read to you—like a daddy rocking his baby to sleep—the most recent posts from my Substack newsletter, which you can find here. (You can subscribe for free or…

Confronting Mortality with Thad Reichley

Nov 05, 2025 1h 4m

Imagine being told you have a terminal illness. Would it change the way you approach each day? Two years ago, Thad Reichley went to the doctor because he had the flu. When initial attempts to address…

Walking Away from Fame and Money with Rachel Heck

Oct 29, 2025 58m

Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at Stanford University, where she went on to win…

Family, Politics & The American Dream with Raj Goyle | Reasonably Happy

Oct 22, 2025 53m

Raj Goyle is running for Comptroller of New York state, and he wants your support. He’s got mine because I think Raj is what America is all about. A first-generation Indian-American, Duke undergrad…

Stoic Street Smarts w/ Ed Latimore

Oct 15, 2025 1h 10m

Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in…

Soul on Fire w/ John O’Leary (Encore episode)

Oct 08, 2025 53m

John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really,…

Why You Will Never Feel Rich w/ Daniel Crosby

Oct 01, 2025 58m

Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the…

Why Two Parents Are Better Than One w/ Melissa Kearney (Encore)

Sep 24, 2025 42m

Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised…

Frequently Asked Questions

How many episodes does Reasonably Happy with Paul Ollinger have?

Reasonably Happy with Paul Ollinger has published 317 episodes since January 2019, covering topics in Business, Philosophy.

Is Reasonably Happy with Paul Ollinger still active?

Reasonably Happy with Paul Ollinger is currently highly active with new episodes weekly. Average episode length is 54m.

How do I contact Reasonably Happy with Paul Ollinger for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Reasonably Happy with Paul Ollinger, including email and social media links.

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