Podcast
Reasonably Happy with Paul Ollinger
Hosted by Paul Ollinger · EN
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.
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Episodes
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5 Questions with Andy Borowitz
3d ago00:31:13Tap to summarizeOn 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, FLThat is all - have a wonderful day! Get full access to Reasonably Happy at words.paulollinger.com/subscribe
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A Political Family Black Sheep Tells All (with Rosebud Baker)
1w ago00:50:23Tap to summarizeMy 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
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5 Questions with A.J. Jacobs
1w ago00:32:17Tap to summarize✍️ 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 moviesSubscribe to A.J.’s Substack, A.J. Jacobs Get full access to Reasonably Happy at words.paulollinger.com/subscribe
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I Read My Essays to You
2w ago00:35:59Tap to summarize✍️ 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
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5 Questions with Dave Barry
3w ago00:30:52Tap to summarize✍️ 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 interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy. Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published dozens of books on myriad topics that sold millions of copies—of books, not topics—in 22 languages. The New York Times called him “the funniest man in America.” (And when has the NYT ever been wrong?) In other words, he’s accomplished an incredible amount in the funny game, and I'm thrilled I got to talk to him. In this fast-moving 30 minute conversation, we talk about:• What he’s looking for in a nursing home.• Advice for me on shepherding my kids through the college search process (even though it doesn’t matter where they end up)• The rock band he plays in with Stephen King, Amy Tan, Roy Blount, Jr., Scott Turow, and many other• Which other authors make him laugh• What Baby Boomers could learn from Gen Z (and vice versa)Listen now and share with all your friends! Also, come see me tell jokes (or give a talk), in person:* June 4 - Atlanta Athletic Club* June 5 and 6 - Laughing Skull Lounge, Atlanta* June 12 - Wade Hampton Country Club, Cashiers, NC (Talk)* 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
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Gretchen Rubin Will Teach You to be Happy
3w ago00:58:34Tap to summarize✍️ 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 discover elements of the conversation I didn’t recall. Upon revisiting this 2025 conversation with best-selling author Gretchen Rubin, I of course remembered that she is a warrior for happiness and the practices that help her huge readership attain it. But listening again, I was struck by how cool Gretchen is. Not “cool” in a biker-jacket / beat poetry / clove cigarette way, but in the “I know who I am, what I’m committed to, and how I can add value to the world” way. I don’t claim to know Gretchen, but it seems logical to me that this self-awareness is a by-product of the kind of work she evangelizes. And it is work. As Aeschylus advised in the quote above, happiness is always there if we choose it, but only if—in the hard times—we are willing to get off the couch or smile through the pain. In times like these, Gretchen’s writing can help us find a path through the noise and, as she describes it, “identify ways we can take happiness from the transcendent to the concrete.” A great way to start that process is to listen (or re-listen) to this episode and take her happiness quiz here. You can also find many more applicable insights on Gretchen’s Substack, Secrets of Adulthood. Remember, happiness is growth—keep growing!---Come see me (Paul) tell jokes (or give a talk), in person:* June 4 - Atlanta Athletic Club* June 5 and 6 - Laughing Skull Lounge, Atlanta*June 12 - Wade Hampton Golf Club, Cashiers, NC * 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
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Money, Family & Comedy w/Roy Wood Jr.
May 1400:56:44Tap to summarize✍️ 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 has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little hypocrisies we all live with. In addition to The Daily Show, Roy has performed on The Tonight Show, The Late Show with David Letterman, BET’s Comic View, Conan, and many other top TV programs. He is now the host of the CNN current events-comedy show, Have I Got News for You. His 2025 memoir, The Man of Many Fathers explores—among other things—Roy’s complicated relationship with his father, Roy Wood, Sr., a civil rights journalist and African American radio pioneer.Today, Roy and I talk about money, family, fatherhood, and we go deep on the craft of comedy.Speaking of comedy, see my upcoming shows below. Save the date / buy your tickets!COMEDY NEAR YOU - GET YOUR TICKETS!* May 16: QED, Astoria Queens, 9:30* May 20: Dunwoody Country Club (members only)* May 21: Atlanta Punchline - ON SALE* May 22-23: DC Comedy Loft ON SALE* 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
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How to Get Rich in America
May 701:06:04Tap to summarize✍️ 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 hogwash, baloney, and complete malarkey. Joseph Moore is a historian, entrepreneur, investor, and the author of a new book called How to Get Rich In American History: 300 Years of Financial Advice that Worked (And didn’t) in which he explores how ambition, risk, and reinvention have shaped America from the very beginning. He also reveals the money myths, sacred cows, side hustles, and NAYsayers that have always been a part of our society. What if so-called timeless beliefs about money like “invest for the long run,” “compound interest builds wealth,” and “real estate always goes up” weren’t always true…and play out less often than you think they do. Joseph’s book is part history, part playbook, and part reality check. He brings lessons to life with rigor that is deeper than an oil well and a wit that is dryer than the Texas plains. And in so doing he demystifies the past in order to clarify the present for anyone thinking about money, success, and what it really means to “make it” in America.📕 Follow Joseph here. 📗 Get full access to Reasonably Happy at words.paulollinger.com/subscribe
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The Fragile Power of Wealth
Apr 3000:47:24Tap to summarizeIf 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 individuals—the kind of people most of us assume have life completely figured out. Spoiler alert: they don’t. Dr. Hokemeyer is the author of Fragile Power, a fascinating look at the emotional and psychological challenges that come with extreme wealth, fame, status, and success. In his work, he’s seen firsthand how money can insulate people from consequences, distort relationships, and quietly fuel addiction, anxiety, and isolation. In other words, he has a front-row seat to the uncomfortable truth behind the fantasy. Today, we talk about why power is more fragile than it looks, how wealth can complicate identity and purpose, and what it actually takes—whether you’re worth $10,000 or $10 billion—to build a life that feels meaningful.✍️ Subscribe to Paul’s Substack here. ✍️📈Rate Reasonably Happy here.📈👀 Learn More about Dr. Paul here. 👀 Get full access to Reasonably Happy at words.paulollinger.com/subscribe
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Surviving the Loss of a Child
Apr 1601:04:01Tap to summarize“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 Colbert, where his work has earned him a Peabody Award, a WGA Award, and two Emmy nominations. He made his off-Broadway debut in Sorry For Your Loss, a raw, comedic, and deeply vulnerable one-man show about coping with a parent’s worst fear, the loss of a child. This is a sad but inspiring conversation. I found Michael’s attempt to make sense out of his grief and to honor Fisher’s brief life to be an uplifting act of service. You can watch the show starting March 27 on the Dropout network.✍️ Subscribe to Paul’s Substack here. ✍️📈Rate Reasonably Happy here.📈👀 Watch Sorry for Your Loss here. 👀 Get full access to Reasonably Happy at words.paulollinger.com/subscribe
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