Reasonably Happy with Paul Ollinger

Paul Ollinger
  • 4.9 (442)
  • Comedy
  • Updated Weekly

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

  1. 2d ago

    The Richest Family You've Never Heard Of

    Investment management firm Fidelity is a private company that administers over $18 trillion in assets—that’s greater than the GDPs of Germany, Japan, the United Kingdom, and France combined. (Or, it’s18 Elon Musks.) Last year, the company earned almost $13 billion in profit, half of which goes to the family who started it. To be more precise, it goes to the founder's grandchildren, a few of whom have taken major roles inside the still-burgeoning business. My guest this week is Justin Baer, award-winning journalist at the Wall Street Journal and author of the new book House of Fidelity: The Rise of the Johnson Dynasty and the Company that Changed American Investing. In this conversation, Justin and I discuss: * How this financial family dynasty was built * Succession planning for a complex and massive family business * The rise of Abigail “Abby” Johnson, Fidelity’s Chairman CEO and founder’s granddaughter, with estimated net worth of $35 billion. Get Justin’s book here. Subscribe to Paul's Substack here. See Paul (aka, Me) Tell Jokes Live Near You! * Los Angeles: The Venice West, 7/21 * New York: QED Astoria, 7/31 * San Francisco: Cobbs Comedy Club, 7/23 * Southampton, NY: Sticks and Stones Comedy Club, 8/1 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    52 min

  2. Jul 2

    TRIGGERnometry's Francis Foster on Teaching, Comedy, and Why the U.K. is F****d

    Francis Foster is the co-host of the massively popular TRIGGERnometry podcast and author of the new book (Un)Educated: My Life as a Teacher, and Why You Should Never Become One (which you should buy here). In this honest, fun, and sometimes stark conversation, Francis and I discuss: * Why teaching is a terrible job. * What he loves about TRIGGERnometry * His love for Buc-ees* (which are closer to 50,000 square feet than the 8,000 I mentioned) * How the United Kingdom is “f****d” * Why the Stone Roses won’t help incoming PM, Andy Burnham Get his book, and watch the Francis Foster Show on YouTube. Follow Paul on Substack here. See Paul tell jokes live in July: * Philadelphia: Next In Line Comedy, 7/3 * Los Angeles: The Venice West, 7/21 * New York: QED Astoria, 7/31 * San Francisco: Cobbs Comedy Club, 7/23 * Southampton, NY: Sticks and Stones Comedy Club, 8/1 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    31 min

  3. Jun 24

    W. Kamau Bell on Cosby, Comedy, and Father's Day

    I was most pleased to speak this afternoon with W. Kamau Bell, a Peabody Award and 4-time Emmy-winning comedian, filmmaker, and television host who is also a Celebrity Jeopardy champion! He is best known as the creator and host of CNN’s United Shades of America on which he spent seven seasons traveling the country exploring communities, subcultures, and perspectives that often go overlooked. The show demonstrated his unique skill of helping people conduct difficult conversations without losing their sense of humor. Not that he’s afraid to mix things up. Kamau’s 2022 HBO docu-series, We Need to Talk About Cosby dove deep into numerous allegations of sexual assault against legendary comedian and television icon, Bill Cosby, a comedian whose work Kamau deeply admired. Kamau has a new podcast called Who’s With Me? on which he has already talked to Ted Danson, Delroy Lindo, Daveed Diggs, and Kristen Kish. He spoke to me from his home in Oakland, CA where he lives with his wife and their three daughters. In this occasionally-serious, but most enjoyable conversation, we discuss: * The difference between craft and character * His love of podcasting * Comedy nerd-ship * The best part about Father’s Day * And—most importantly— Dave Barry Leave comments below. And follow / subscribe to this podcast. Also subscribe to Kamau’s ‘Who’s With Me?’ Substack here and to Paul’s ‘Reasonably Happy’ Substack here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    28 min
  4. 5 Questions with Bruce Feiler

    Jun 18

    5 Questions with Bruce Feiler

    Thanks very much to Bruce Feiler for joining me on the 5 Questions livestream to discuss his new book A Time to Gather: How Ritual Created the World—and How it Can Save Us. In this upbeat and positive conversation, Bruce and I discuss: • What came first, ritual or religion? • Why SEC football tailgating fits the definition of ritual • How Balinese tooth-filing ritual has much in common with modern Western dental customs • Why so many New Yorkers are jumping on the Knicks bandwagon (including someone’s wife who shall remain nameless) Subscribe to Bruce’s ‘The Nonlinear Life Substack and to Paul’s Reasonably Happy Substack. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    37 min
  5. 5 Questions with Andy Borowitz

    Jun 15

    5 Questions with Andy Borowitz

    On this third episode of 5 Questions, I speak with Andy Borowitz, whose massively popular newsletter The Borowitz Report tops out around 200 words per post. So this intro is going to be brief! Even if you belong to Andy’s army of loyal readers, you might not know that he is also the co-creator of The Fresh Prince of Bel-Air and wrote on classic 80’s TV shows, The Facts of Life and Square Pegs, which helped to launch Sarah Jessica Parker’s career. In this fast-paced conversation, Andy and I discuss: * His career in and out of Hollywood * How to write succinctly * His grammatical pet peeve(s) * Whether AI will ever be able to write comedy * The best advice he got from Susie Essman (aka, the secret to a happy life) Subscribe to The Borowitz Report here. Subscribe to Paul Ollinger's Reasonably Happy here. See Paul tell jokes near you: • June 19 and 20 - The Comedy Catch, Chattanooga • June 25 - ❤️Happy Couples Show❤️ West Side Comedy Club, NYC • July 21 - The Venice West, Los Angeles • July 23 - Cobbs Comedy Club, San Francisco • Aug 1 - Sticks and Stones Comedy Club, Southampton, NY • Aug 8 - Atlanta Country Club (private show) • Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL That is all - have a wonderful day! Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    31 min

  6. Jun 12

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

    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 Night Live, Inside Amy Schumer, and That Damn Michael Che. In her new autobiography, Fully Baked: A Messy Memoir, Rosebud shares the story of being the grand-daughter of James Baker, the former Secretary of State and Secretary of the Treasury who also served as White House Chief of Staff for Presidents Reagan and George H.W. Bush. She also relates unfiltered observations on her parents’ divorce, her addiction to drugs and alcohol, her multiple miscarriages, and the death of her younger sister, Graeme. Her latest Netflix special is called The Mother Lode. She filmed half of it while eight months pregnant and the other half after giving birth. It was named one of the best comedy specials of 2025. See Rosebud’s upcoming dates and get the book here. ✍️ Follow Paul Ollinger on Substack by clicking here ✍️ See Paul tell jokes live near you: • June 19 and 20 - The Comedy Catch, Chattanooga • June 25 - Happy Couples Show, West Side Comedy Club, NYC • July 21 - The Venice West, Los Angeles (on sale soon) • July 23 - Cobbs Comedy Club, San Francisco • Aug 1 - Sticks and Stones Comedy Club, Southampton, NY • Aug 8 - Atlanta Country Club • Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    50 min
  7. 5 Questions with A.J. Jacobs

    Jun 10

    5 Questions with A.J. Jacobs

    ✍️ 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 great choice to be my second guest on my 5 Questions series of Substack livestreams. Over the past two decades, A.J. has built a remarkable career by asking questions most of us would never think to ask—and then answering them by turning himself into the experiment. He’s read the entire Encyclopedia Britannica, lived according to the Bible as literally as possible, pursued bodily perfection, traced his family tree to millions of relatives, thanked every person involved in making his morning cup of coffee, explored the world of puzzles, and most recently spent a year trying to live according to the original meaning of the U.S. Constitution. The result has been a string of New York Times bestsellers, including The Know-It-All, The Year of Living Biblically, Drop Dead Healthy, Thanks a Thousand, The Puzzler, and The Year of Living Constitutionally. Along the way, he’s become one of America’s most entertaining guides to the intersection of happiness, curiosity, gratitude, self-improvement, and human connection. What I love about A.J.’s work is that beneath all the humor and outrageous experiments is a serious question: How should we live? And instead of lecturing, he goes out and tests ideas on himself—often with hilarious consequences. We talk about: * The United States’ 250th Birthday * Geeking out on compound anniversary words like “semiquincentennial” * What I should keep in mind while I help my kids search for colleges * Summer blockbuster movies Subscribe to A.J.’s Substack, A.J. Jacobs Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    32 min

  8. Jun 3

    I Read My Essays to You

    ✍️ 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 Manosphere, schadenfreude, career trajectories, and more. I understand that you don’t always have time to read everything I crank out—you’re on the move, working out, or re-arranging your sock drawer. And that’s okay. So today—as I do occasionally—I’m sending you this podcast version of me reading TO YOU. And now you don’t have any excuses to not enjoy my wonderful writing. You’re right - it’s quite generous of me, but I enjoy it. You can read all my stuff and catch some upcoming live streams here! COME SEE ME PERFORM COMEDY NEAR YOU (in Atlanta, Chattanooga, NYC, L.A., SF, Southampton, Sarasota)... * June 4: Atlanta Athletic Club (members only) * June 19-20: Comedy Catch, Chattanooga ON SALE * June 25: Couples Therapy Comedy at West Side Comedy Club, NYC * July 21: The Venice West, Los Angeles - On Sale soon * July 23: Cobbs Comedy Club, San Francisco - ON SALE * Aug 1: Sticks and Stones Comedy Club, Southampton, NY - * Aug 8: Atlanta Country Club (members only) * Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE * October 15: Capital City Country Club (members only) Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    36 min
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4.9
out of 5
442 Ratings

About

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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