Reasonably Happy with Paul Ollinger

Paul Ollinger

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. 1D AGO

    Insider Trading w/Tom Hardin

    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 Fraud, which are felonies. In 2008, during the beginning of the great finanical crisis, Tom desperately needed to put some points on the board at his fund. And since everybody else in the industry seemed to be doing it, Tom allowed himself to trade equities on material, non-public information—something he knew was illegal. After being stopped by the FBI on the streets of Manhattan, Tom agreed to become an informant and wore a wire over 40 times to aid the agency in its investigation of big fish like Steve Cohen of SAC who paid a $1.8 billion fine and Rajaratnam of of Galleon Group who went to jail for 7.5 years. I spoke to Tom this week about his new book, Wired on Wall Street: The Rise and Fall of Tipper X, One of the FBI’s Most Prolific Informants. A scrappy, middle-class kid from suburban Atlanta (Go Braves!), Tom willed himself into the University of Pennsylvania’s famed Wharton School of Business, which launched him into the finance industry. He eventually earned a seat at a prestigious hedge fund and was on his way until the intense pressure of the gig led him to make a terrible decision that earned him only $46,000 but ended his career. Today, Tom works with Fortune 500 companies, financial institutions, law firms, business schools, and leadership teams, delivering keynotes and advisory engagements on behavioral ethics, culture risk, and organizational conduct. NOTE: The actor in 'Traffic’ actor whose name I was trying to remember is Benicio Del Toro, not Guillermo Del Toro. Please forgive me. Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!)    Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE  Pre-order Tom’s book HERE.

    1h 15m

  2. FEB 12

    Surviving Middle Age w/ Ben Markovits

    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 was short-listed for the Booker Prize, focuses on a 55-year-old law professor’s midlife crisis and transformative road trip after his children leave home. You might say it examines the sources of happiness in our lives as we age. Ben’s writing has appeared in The New York Times, The New Yorker, and The Guardian. He spoke with me from his home in England. Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠⁠ (DO IT!)    Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠   Read Ben's book ⁠NYT essay

    51 min

  3. FEB 5

    Marriage, Infidelity, and Millennial Disillusionment with Erin Somers

    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 mocking examination of young middle age.” I wanted to speak with Erin because her characters reflect a sense of grown-up melancholy arising when goals like home ownership, careers, and parenthood don’t provide the fulfillment that was expected of them. So what do we do, she asks implicitly, when we find ourselves in a life designed to have meaning but does not deliver on that promise? Her characters also embody the impossible and contradictory messages society has imposed on gender roles for her generation. For men: be sensitive, inclusive, do half the housework, but still make a lot of money. For women: go conquer the corporate world while simultaneously being a present, nurturing mother and a sensual, doting wife. To me, this issue—even more than the deliciously provocative infidelity—is what has me continuing to think about the book, weeks after I finished it. Erin's writing and reportage has appeared in The New York Times Magazine, The New Yorker, The Paris Review, Esquire, GQ, The Nation, The New Republic, and elsewhere. Vogue named her first novel, Stay Up With Hugo Best, to their list of the Best Books of the Year for 2019. ✍️Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠⁠ (DO IT!) ✍️ https://ratethispodcast.com/paulopod 📈Subscribe to ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠.📈 https://words.paulollinger.com/ 📔Get Erin's book ⁠here⁠. 📔 https://www.erinsomers.com/

    45 min

  4. JAN 28

    A.I. Facts, Fears and Fiction (w/ Bryan Reimer)

    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 he explores AI’s power and potential to change the world. He and I sat down this week to discuss the facts, fears, and fiction around what might be the most transformational innovation of our lifetimes. Brian offers a grounded, human-centered perspective on how AI is evolving—and why most of the extreme hype and trepidation miss the point. Rather than a doomsday takeover, he frames AI as a long-term productivity tool that works best in collaboration with humans, not instead of them. Along the way, we discuss energy demands, competition between the U.S., China, and Europe, deepfakes, “oh sh*t moments,” and how everyday people can start using tools like ChatGPT right now to improve their work and lives. Bryan is a research scientist at MIT’s Center for Transportation & Logistics and the MIT AgeLab. With over two decades of experience in human-centered technology research, he has become a leading voice in the future of mobility and making AI systems more practical, accessible, and beneficial for everyday use.   ✍️Please rate and review ⁠⁠Reasonably Happy⁠⁠ (DO IT!) ✍️ 📈Subscribe to Paul’s ⁠⁠Substack newsletter⁠⁠.📈 📔Get Bryan’s book here. 📔

    44 min

  5. JAN 15

    From Apartheid to Atlanta w/ Robyn Curnow

    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 as the network’s Africa correspondent out of Johannesburg and covered Europe out of CNN’s London Bureau. If you don’t recognize her name, I bet you’ll recognize her distinctive voice because you likely saw her interviews with some of the most prominent people of our lifetimes, including Nelson Mandela, Jimmy Carter, Bill Clinton, George W. Bush, Michelle Obama, Oprah Winfrey, and Archbishop Desmond Tutu. Robyn has covered news stories as diverse and dynamic as Africa’s HIV/AIDS epidemic, the rise of Boko Haram, the 2010 World Cup, and the murder of Jammal Khashoggi. This work earned her and her colleagues multiple Emmy nominations, the Royal Television Society Award, and the duPont-Columbia Award. On her new podcast, Searching for America—which I love—Robyn explores our society and culture through the eyes of a new-comer. Like a modern-day de Tocqueville, she offers a sincerely interested outsider’s perspective on the quirks of American life, including the Halloween Industrial complex, the obsession with high school graduation and college acceptance, turducken, and—most importantly—our collective love of Dolly Parton. She lives in Atlanta where she and I serve on a school board together. Rate and Review Reasonably Happy: https://ratethispodcast.com/paulopod Read Paul’s Substack essays here: https://words.paulollinger.com/ Listen to Searching for America here: https://open.spotify.com/show/3j83wBMdUQnOcQTfK2pg9I

    1h 2m

  6. JAN 7

    Rewrite Mental Illness w/Laura Delano

    Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which was not something openly discussed at the time in her wealthy hometown of Greenwich, CT. Over the next 14 years, Laura was diagnosed with bipolar disorder, depression, social anxiety disorder, eating disorder, poly-substance dependence, and borderline personality disorder. These conditions earned her prescriptions for Seroquel, Abilify, Klonopin, Ativan, Ambien, Prozac, Effexor, Celexa, Cymbalta, Wellbutrin, Lexapro, lithium, and many more. During this time, she engaged in self-harm, spent time in psychiatric hospitals, and attempted to take her own life. In 2010, Laura decided she had had enough with all the diagnoses and the drugs. Her book tells the story of how she weaned herself from this medical regimen and found a stable life free of prescriptions. You’ve gotta listen to this conversation. Laura and I talk about mental health, the pharmaceutical industry, how her behavior affected those around her, how her family dealt with their difficult sister and daughter, and how that love finally helped to see her through.Btw, the ‘80s punk band whose name I couldn’t remember around the 10-minute mark is Suicidal Tendencies. Thanks to my pal, “Nashville Ben” for recommending Laura’s book for me. Please rate and review ⁠⁠Reasonably Happy⁠⁠ (DO IT!)  Subscribe to Paul’s ⁠⁠Substack newsletter⁠⁠. Check out Laura’s website here.  NOTHING IN THIS EPISODE SHOULD BE REGARDED AS MEDICAL ADVICE. IF YOU ARE EXPERIENCING PHYSICAL OR MENTAL DISTRESS, PLEASE SEEK THE HELP OF A MEDICAL PROFESSIONAL. ALSO, DO NOT CHANGE YOUR PRESCRIPTION REGIMEN W/O CONSULTING YOUR DOCTOR.

    1h 14m

  7. 12/18/2025

    Find your Essential Intent w/ Greg McKeown

    Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions for 2026, Greg’s insights will be a great way to think through WHAT REALLY MATTERS to you. To demonstrate how challenging this seemingly obvious exercise can be, I asked Greg how to help me focus my sincere but varied slate of professional ambitions. It gets a little uncomfortable, but that’s the point! And if you get one thing out of this episode, I hope it’s the 7 words Greg shares that will help you be a better spouse, parent, friend and co-worker. Thank you to my friend, the painter and 1985 high school soccer phenom, Brendan O’Connell for bringing Greg’s work to my attention. Please rate and review ⁠Reasonably Happy⁠ (Seriously, DO IT!)  Subscribe to Paul’s ⁠Substack newsletter⁠      Start your Essentialism journey ⁠here⁠    Okay, here’s Greg’s BIO: Greg McKeown has written two New York Times bestsellers: “Essentialism: The Disciplined Pursuit of Less,” which Goodreads users voted “The #1 Leadership and Success Book to Read in a Lifetime,” and “Effortless: Make It Easier to Do What Matters Most.” Together, they have been published in 37 languages. Greg is a highly sought-after public speakers globally and has spoken to over 500 companies while traveling to more than 40 countries. His clients include Apple, Google, Microsoft, and Nike. (Perhaps you’ve heard of these companies. Hmm?)  Greg hosts the cleverly named "The Greg McKeown Podcast,” which is ranked in the Top 5 of all self-improvement podcasts, and has hosted luminaries like Arthur Brooks, Matthew McConaughey, and Maria Shriver. His work has been covered in The New Yorker, The New York Times, Time, Fast Company, and Harvard Business Review…among others.

    1h 26m

  8. 12/03/2025

    High Net Worth Divorce with Laura Wasser

    People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like Angelina Jolie, Kim Kardashian, Johnny Depp, Ryan Reynolds, Dr. Dre, Kevin Costner, Maria Shriver, and Jimmy Iovine, among many others. And while “celebrity divorce attorney” might conjure up images of a rapacious shark in Prada boots squeezing every dollar out of her clients’ exes, Laura preaches the gospel of divorce with dignity. Her book, It Doesn’t Have to Be That Way: How to Divorce Without Destroying Your Family or Bankrupting Yourself is a jungle guide for ending a marriage while preserving decency, values, and a couple’s wealth. As she writes, “…the more acrimony, argument, and angst, the more money your attorney makes. We profit from your inability to resolve issues.” In other words, don’t pay your lawyer $1,000/hr to determine—as famously captured in When Harry Met Sally—who gets the “stupid, wagon wheel, Roy Rogers, garage sale coffee table.” Her book is a plea to all those going through one of the most stressful human experiences possible to summon your best self and think about who you want to be when the dust settles. Laura and I talk about the fundamental language of divorce, including spousal support, child support, no-fault divorce, community property, and also the more philosophical dimensions of the process, like the concept of “fairness” and how one defines “winning.” Sincere thanks to my former Facebook colleague, Matt Jacobson for making the connection to Laura. I appreciate, Jake! (encore presentation) Follow Laura on ⁠on Instagram⁠ and learn more about her practice ⁠here⁠.   ✍️Subscribe to Paul’s Substack ⁠here⁠ ✍️

    41 min
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Trailer

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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 - 2026
  • Episodes
    314
  • Rating
    Explicit
  • Copyright
    Copyright © 2019-2024 Absolutely Huge Company, LLC. All rights reserved.
  • Show Website
    Reasonably Happy with Paul Ollinger

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