Reasonably Happy with Paul Ollinger

Reasonably Happy with Paul Ollinger

Paul Ollinger

Episodes 330
Avg. Duration 53m
Activity Highly Active
Apple Rating 4.9 (442)
Since Jan 2019
Latest Episode Jun 2026

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Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
72%
Hosting
api.substack.com

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About This Podcast

Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection.

words.paulollinger.com

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Recent Episodes

A Political Family Black Sheep Tells All (with Rosebud Baker)

Jun 12, 2026 50m

My guest today is Rosebud Baker. Rosebud is one of the sharpest and most honest voices in comedy today. She’s an Emmy-nominated and Writers Guild Award-winning writer whose credits include Saturday…

5 Questions with A.J. Jacobs

Jun 10, 2026 32m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a…

I Read My Essays to You

Jun 03, 2026 35m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack over the past six months. They cover the…

5 Questions with Dave Barry

May 28, 2026 30m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack…

Gretchen Rubin Will Teach You to be Happy

May 26, 2026 58m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Happiness is a choice that requires effort at times.” -Aeschylus Whenever I go back and re-listen to one of my podcast interviews, I always…

Money, Family & Comedy w/Roy Wood Jr.

May 14, 2026 56m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can…

How to Get Rich in America

May 07, 2026 1h 6m

✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the…

The Fragile Power of Wealth

Apr 30, 2026 47m

If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who…

Surviving the Loss of a Child

Apr 16, 2026 1h 4m

“How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and…

Millionaires v. Billionaires in NYC

Apr 02, 2026 1h 6m

Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a glamorous Manhattan apartment building where the…

The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain

Mar 26, 2026 1h 1m

This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with some of the biggest brands and celebrities in…

Money, Fame, and Misery: Meet the Beatles

Mar 19, 2026 58m

Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett )In the late ‘60s, The Beatles had it all: worldwide fame, critical admiration, and more money than they ever could have imagined. So why…

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

Mar 12, 2026 57m

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

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 58m

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 13m

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 47m

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 41m

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 43m

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 59m

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…

Frequently Asked Questions

How many episodes does Reasonably Happy with Paul Ollinger have?

Reasonably Happy with Paul Ollinger has published 330 episodes since January 2019, covering topics in Comedy, Society & Culture.

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 53m.

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

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