Reasonably Happy with Paul Ollinger

Paul Ollinger
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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.

  1. 3D AGO

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

    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 and Harvard Law grad, Raj was the co-founder of Bodhala, a legal spend analytics and management platform which he and team sold to Onit. As the leader of Phone Free New York, Raj led a bi-partisan effort to get phones out of the classroom across New York state. And now he wants to take his immense talent and experience to Albany for the most important position (Comptroller!) you’ve never thought about. As you’ll hear, there’s plenty that Raj and I disagree about. But he’s the kind of person we need more of in government: a smart, driven leader who wants to make government work for citizens. Among lots of other things, Raj and I discuss: -Zohran Mamdani, the NYC mayoral candidate whom Raj supports and I DO NOT -What a comptroller does -Money, happiness, and public service -What it was like for his parents–both doctors–to emigrate to the U.S. -How Jimmy Carter helped shaped his belief in ethical capitalism and an accountable government AI’s impact on the economy and what we can do about it ✍️Please rate my podcast (https://ratethispodcast.com/paulopod) ✍️ 🗳️Learn more about Raj (https://rajgoyle.com/) 🗳️ 👊Get Paul’s Substack newsletter (http://words.paulollinger.com) 👊

    53 min

  2. OCT 15

    Stoic Street Smarts w/ Ed Latimore

    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 Physics. I spoke to Ed about his new memoir, Hard Lessons From the Hurt Business: Boxing and the Art of Life in which he shares stories about discipline, sobriety, and self-mastery. Ed and I talk bout how emotional control can outpower ego, how true masculinity is rooted in accountability, and why forgiveness is the ultimate form of strength. He also discloses that he (loves and) likes his wife! Thanks to Rob Henderson for bringing Ed to my attention. ✍️Please leave us a rating here ✍️ 🥊Learn more about Ed here 🥊 👊Get Paul’s Substack newsletter here 👊

    1h 10m

  3. OCT 8

    Soul on Fire w/ John O’Leary

    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, really burned, over 100% of his body, 87% of which were third-degree burns. Doctors gave him less than 1% chance of living and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, he got through it. His journey back took years, required dozens of surgeries, and cost him all of his fingers. Today, John is a world-renowned inspirational speaker who addresses large audiences around the globe. John is also the author of the best-seller On Fire!: 7 Choices to Ignite a Radically Inspired Life and In Awe: Rediscover Your Childlike Wonder Unleash Inspiration, Meaning, and Joy. He hosts the Live Inspired podcast. John and I have a lot in common. We were both one of six kids in a big, Catholic family and raised by amazing parents who were married for over 50 years and whose humility and grace inspire us to this day. We’re both husbands and dads, and both want our audiences to be radically aware of the value of their lives and the opportunity to make every day count. In this conversation, we discuss the importance of: Living in the moment Gratitude Family Courage Friends who will fight for you Finding your Talents “Saying Yes to being used for good.” ✍🏾Please leave us a rating: https://ratethispodcast.com/crazymoney. ✍🏾 👊Get Paul’s Substack newsletter: https://substack.com/@paulollinger 👊 Watch the trailer for Soul On Fire: https://www.youtube.com/watch?v=CslVGLETWps

    53 min

  4. OCT 1

    Why You Will Never Feel Rich w/ Daniel Crosby

    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 fun, non-obvious aspects of money and emotions, such as how comparison drives us crazy and why our bias toward action —doing something when things are going wrong — often leads to worse investment results. He offers small tips (like giving your savings account a name) that will help you save more and spend less. Daniel shares lessons from his (Mormon) mission to the Philippines, and we both reflect on how our frugal parents informed who we are today, in almost entirely (but not 100%) good ways. From the dangers of debt and overconfidence to escaping the toxic loop of “I’ll be happy when…,” we cover a lot of ground and have lots of laughs along the way. Listening to these two money-talkers with great hair will improve your life! Read Paul’s Substack: https://words.paulollinger.com/ Listen to Daniel’s podcast, Standard Deviations: https://www.standarddeviationspod.com/episodes *don’t forget the “PhD” part or he gets very mad.😁

    58 min

  5. SEP 24

    Why Two Parents Are Better Than One w/ Melissa Kearney

    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 in two-parent homes have better personal and professional outcomes (ON AVERAGE) than those raised in single-parent homes. Specifically, two-parent homes produce children who are more likely to graduate from high school and college, more likely to stay out of jail, to achieve stable employment, high earnings, and eventually to get married themselves, thus replicating the same advantages they had for their children. For pointing this out, Kearney was excoriated by academic colleagues who accused her of having a right-wing political agenda, which is preposterous considering that she had spent the 20 years prior to writing her book researching social policy, poverty, and inequality. Melissa is the Gilbert F. Schaefer Professor of Economics at the Unversity of NotreDame. She holds a BA in Economics from Princeton and a PhD in Economics from MIT. This is an encore episode from 2023. Follow Paul and read his work here. Learn more about Melissa Kearney here.

    43 min

  6. SEP 17

    Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark

    If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most urgent challenges. In this week’s episode, Craig and I discuss the early days of Craigslist, its radical “revenue-minimization” strategy, and how its simple tools changed the classified ads game in the late ’90s. He told me how Sunday school values shaped his approach to business, why he demoted himself to customer service rep, and what he learned by hiring a CEO to run the company he built. Our conversation explores the art of giving money away strategically: from supporting veterans and military families to investing in cybersecurity and protecting democracy. We also get personal - talking favorite TV shows, the pros and cons of AI, and the big question: how much is enough? Listen now. Read Paul’s Substack here⁠: https://words.paulollinger.com/ Learn more about Craig’s philanthropic endeavors ⁠here⁠: https://craignewmarkphilanthropies.org/ Please rate, review, and share this great episode!

    43 min

  7. SEP 10

    Laughing at Death

    What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In this episode, I (i.e., me–Paul–the host) sit down with John Kenney—award-winning author and longtime New Yorker contributor—for a candid and sometimes very funny conversation about writing, death, and living imperfectly, a topic we all know something about. I first learned of John 20 years ago when someone gave me a copy of his book Truth in Advertising and said, “this author is smart, wicked funny, and a little dark - you’ll love it.” I did. So I was thrilled to get the chance to talk to him about the new book and to hear a first-hand account of his journey from Ogilvy & Mather copywriter to getting published in the New Yorker and eventually becoming an award-winning novelist. One of six boys in a big Irish family, John dedicates the book to his late brother, a firefighter who died of pancreatic cancer, potentially related to his work at Ground Zero, starting the afternoon of 9/11/01. I just re-listened to this conversation, and I am grateful to John for being so open about his career, his family, and his admiration for the father who became a widower far too soon. I hope you enjoy it as much as i did. . Learn more about John: https://www.instagram.com/johnkenneywriter/?hl=enFollow Paul: https://words.paulollinger.com/

    55 min

  8. SEP 3

    Rise of Populism

    Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in American politics. From growing up in East Tennessee to advising senators, governors, and big-time campaigns, Brad’s been in the trenches for decades — and he’s got the stories to prove it. Paul and Brad dig into the rise of populism, how the Republican Party has changed, and the real challenges facing Democrats in 2025. Brad gives unfiltered takes on Donald Trump’s second term, what a post-Trump GOP might look like, and why primaries and caucuses shape the country’s future. You’ll also hear what Supreme Court Justice Amy Coney Barrett was like at Rhodes College (where both Paul and Brad went to school), some high-stakes dog track bets, and why politics is still a young person’s game. It’s part insider scoop, part history lesson, part comedy — the kind of conversation that’ll make you think, laugh, and maybe even yell at your screen. If you want the truth about U.S. politics without the cable news noise, this is it.

    51 min
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About

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.

Information

  • Creator
    Paul Ollinger
  • Years Active
    2019 - 2025
  • Episodes
    302
  • Rating
    Explicit
  • Copyright
    Copyright © 2019-2024 Absolutely Huge Company, LLC. All rights reserved.
  • Show Website
    Reasonably Happy with Paul Ollinger

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