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Artwork for Reasonably Happy

Reasonably Happy with Paul Ollinger

Paul Ollinger
Happiness
Mental Health
Wealth
Comedy
New York City
Addiction
Social Media
Philanthropy
John O'leary
Innovation
Grief
Family
Narcissism
Rudolf Diesel
Democracy
Diesel Engine
Money
Gratitude
Family Dynamics
Poverty

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

PublishesWeeklyEpisodes325Founded7 years ago
Number of ListenersCategories
ComedySociety & Culture

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Artwork for Reasonably Happy

Latest Episodes

✍️ 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 still hit hard. A native of Birmingham, AL, Roy ... more

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✍️ 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 American Dream is dead. But my guest today calls this ho... more

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 works almost exclusively with ultra-high-net-worth i... more

“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 a staff-writer on The Late Show with Stephen Colber... more

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Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Roy Wood Jr.
American comedian, known for The Daily Show and stand-up specials; host of CNN Current Events Comedy Show Have I Got News for You; author of The Man of Many Fathers
CNN Have I Got News for You, The Daily Show
Episode: Money, Family & Comedy w/Roy Wood Jr.
Joseph Moore
Historian, entrepreneur, investor, author
Author of How to Get Rich in America, 300 Years of Financial Advice That Worked and Didn't
Episode: How to Get Rich in America
Michael Cruz Kayne
Comedian, actor, staff writer on The Late Show with Stephen Colbert
The Late Show with Stephen Colbert (writer)
Episode: Surviving the Loss of a Child
Chris Pavone
Bestselling author of The Expats, The Doorman, and other thrillers
Author
Episode: Millionaires v. Billionaires in NYC
Steve Chamberlain
Former Turner Broadcasting executive and music/film distribution strategist
Turner Broadcasting, EMI
Episode: The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain
Peter Doggett
Rock music writer and author
Rolling Stone, Mojo, Q (contributor)
Episode: Money, Fame, and Misery: Meet the Beatles
Nir Eyal
Author and researcher focused on beliefs, behavior, and technology
Author of Beyond Belief
Episode: Believe and You Will See! (w/ Nir Eyal )
Matt Kaplan
Science correspondent at The Economist, author of a new book on scientists who were ridiculed for their ideas.
The Economist
Episode: The Courage to Be Right w/ Matt Kaplan
Tom Hardin
Author of Wired on Wall Street, a former FBI informant involved in insider trading investigations.
Episode: Insider Trading w/Tom Hardin

Host

Paul Ollinger
Host of Reasonably Happy; comedian and interviewer focused on happiness, fulfillment, and meaningful living.

Reviews

4.9 out of 5 stars from 501 ratings
  • Grief with Nicole Avant

    I couldn’t have found this episode at a better time. My Mom died unexpectedly 2.5 weeks ago. Just an incredibly traumatic and most painful part of my life. Still and will forever grieve and just getting back to work with more pressure; I cry every day. But the strength that Michelle showed and how she remembers about how her mother would have wanted her to keep going is just so important for me to hear right now. All strength and blessings to her and her family losing such a powerful Mom and wom... more

    Apple Podcasts
    5
    MetalMet
    United States2 months ago
  • Outstanding Content, Highly Entertaining

    I love this podcast because it’s informative, entertaining and covers a wide range of topics that make me smarter and happier. It also helps to answer esoteric questions about life, yet makes me laugh, smile and think.

    Apple Podcasts
    5
    JayHowell69
    United States3 months ago
  • College applications

    Go to a school where you are a little above average. Rinse and repeat through life.

    Apple Podcasts
    3
    Interested bystander
    United States6 months ago
  • College applications

    Mostly naive discussion. What a mess.

    Apple Podcasts
    2
    Interested bystander
    United States6 months ago
  • Thoughtful and Interesting!

    Enjoy listening to Paul navigate through some entertaining conversations and topics. Thanks to Chris Hill for introducing this show to his audience. Highly recommend, cheers Paul!

    Apple Podcasts
    5
    Buzz Doyle
    United States6 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests are consistently high-caliber and the conversations feel both intelligent and approachable.
Audience tends to value practical takeaways and relatable storytelling from a diverse lineup of guests.
Listeners praise the host for being thoughtful, entertaining, and well-prepared.
Some reviews note the host's personal stories and interviewing style as a standout aspect of the experience.
The show blends humor with deep, reflective topics, and offers fresh perspectives on money, happiness, and life.

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Talking Points

Recent interactions between the hosts and their guests.

Surviving the Loss of a Child
Q: What did you say when your wife asked, how am I ever going to be happy again?
He recalls not saying much in that moment, believing silence was the right choice, recognizing the enormity of the question and choosing to stand with his wife rather than try to short-circuit the grief.
Surviving the Loss of a Child
Q: How did you survive?
Kayne describes leaning on love for his wife and the presence of their surviving son Truman, which pulled them into action and helped them keep moving forward, even as the grief remained constant and overwhelming.
Believe and You Will See! (w/ Nir Eyal )
Q: What do you do when you pray or engage in problem-solving through prayer?
Prayer is framed as internal problem-solving that focuses on attributes like patience, perseverance, and gratitude, rather than asking for external outcomes.
Believe and You Will See! (w/ Nir Eyal )
Q: So how do we promote agency on an individual and societal level?
The conversation emphasizes acknowledging nocebos, fostering internal locus of control, and adopting liberating beliefs to empower action, resilience, and growth.
Money, Fame, and Misery: Meet the Beatles
Q: Did writing the Beatles book change your view of the band or its members?
He says writing the book increased empathy for Paul and clarified how John's and others' choices, plus confrontations with fame, shaped the group's trajectory.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Reasonably Happy

What is Reasonably Happy about and what kind of topics does it cover?

The show features candid conversations with a diverse mix of guests—including scientists, authors, athletes, journalists, and thinkers—centered on happiness, meaning, and the practical realities of modern life. Episodes frequently explore how success, failure, relationships, and personal growth intersect with everyday fulfillment, often weaving in lessons from careers in media, science, finance, sports, and public service. Listeners can expect thoughtful storytelling, accessible ideas, and humor from a host who steers conversations toward tangible takeaways about living a more intentional, contented life. A notable strength is the breadth of guest backgrounds, which offers fresh perspectives on happiness that go beyond money or status, maki... more

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Which podcasts are similar to Reasonably Happy?

These podcasts share a similar audience with Reasonably Happy:

1. The Prof G Pod with Scott Galloway
2. Earn & Invest
3. The Long View
4. Two Sides of FI
5. Prof G Markets

How many episodes of Reasonably Happy are there?

Reasonably Happy launched 7 years ago and published 325 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Reasonably Happy?

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What guests have appeared on Reasonably Happy?

Recent guests on Reasonably Happy include:

1. Roy Wood Jr.
2. Joseph Moore
3. Michael Cruz Kayne
4. Chris Pavone
5. Steve Chamberlain
6. Peter Doggett
7. Nir Eyal
8. Matt Kaplan

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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