Reasonably Happy with Paul Ollinger

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

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.😁

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.

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!

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/

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.

What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New York Times bestselling author? In this unforgettable episode, Paul sits down with Lara Love Hardin, author of The Many Lives of Mama Love, a mind-blowing memoir of crippling dependence, incarceration, and survival. Oprah, who picked ‘Mama Love’ for her official book club, described it as "a powerful exploration of redemption, joy, and the human capacity for change.” With unflinching honesty and unexpected humor, Lara shares her journey from PTA meetings to jailhouse shot-caller. In just a few years, she went from stealing from her neighbors to support her narcotic habit to ghostwriting best-sellers for global heroes like Bishop Desmond Tutu. Her story isn’t just about addiction or recovery—it’s about resilience, forgiveness, and how second chances can rewrite a life. If you’ve ever wondered whether transformation is truly possible, this conversation will make you believe in the messy, complicated, and inspiring fight to begin again. Learn more about the work Lara does to help women newly-released from prison get back on their feet: The Gemma Project https://www.thegemmaproject.org/ Subscribe to Paul’s Substack here: https://words.paulollinger.com/

📬 Subscribe to Paul’s Substack: https://words.paulollinger.com/ 📖 Learn more about Jonathan Rauch: https://jonathanrauch.typepad.com/ What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan Rauch returns to the podcast to talk about his new book 'Cross-Purposes: Christianity’s Broken Bargain with Democracy'. Jonathan explains why the decline of organized religion has left a dangerous void in civic life—one now filled by hyper-partisan politics and fear-driven culture wars—and why he believes America needs a renewal of non-political Christianity rooted in courage, forgiveness, and love. We dive into his evolving relationship with faith, his hope for a less fearful, more compassionate citizenry, and the surprising ways music has shaped his worldview—including the life-changing moment he first heard Sgt. Pepper’s Lonely Hearts Club Band in third grade. Jonathan is a Yale grad, senior fellow at the Brookings Institution, award-winning author, and one of the most thoughtful public intellectuals of our time.

Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism comes from, how it is tearing us apart, and how we might fix it. With wit, warmth, and some surprisingly deep evolutionary psychology, Andrew explains how our ancient brains are wired to seek belonging—even if that means choosing teams over Truth. They cover everything from Dunbar’s number to the loneliness epidemic, from the comedy club to Capitol Hilll, and why political identity has become a poor substitute for real community. Whether you're center-left, center-right, or just tired of the noise, this conversation offers a refreshing dose of nuance, laughs, and insight into how we got here and where we could go. If you've ever felt politically homeless—or curious why shouting on Twitter feels like the new religion, this conversation is for you! Don’t miss the part where Andrew suggests that Paul change the name of his podcast to “Drinking Liberal Tears with Paul.” (It’s not going to happen, but just think of how popular it would be if we did!) Subscribe to Paul’s Substack: http://words.paulollinger.com Follow Andrew at https://mightyheaton.com/ 

This week, Paul sits down with Sarah Personette, CEO of Puck, the fast-growing news outlet the New York Times described as “Vanity Fair for the Substack era.” From her ambition to become a CEO at age seven to her senior roles at Facebook, Universal-McCann, and Twitter – which ended after Elon Musk bought the company, Sarah unpacks what it takes to lead teams through uncertainty, disruption, and reinvention. She explains Puck’s blend of high-caliber journalism with modern distribution, and how to survive the oncoming AI onslaught. Sarah speaks candidly about navigating career transitions, modeling work-life balance, leading global teams, and raising children with intention while running billion-dollar operations. Whether you're a founder, a parent, or just starting out, her mantra—“Stay calm, stay focused, stay classy”—is a playbook for thriving in today’s chaotic world. It’s a raw, funny, deeply human look at the future of media, work, and purpose-driven leadership. Also, don’t miss Paul gushing with ‘80s nostalgia about the movie About Last Night starring Demi Moore and Rob Lowe. (Don’t worry - it’s relevant) Learn more about Puck here: https://puck.news/ Subscribe to Paul’s Substack here: http://words.paulollinger.com Watch About Last Night: https://www.amazon.com/About-Last-Night-Rob-Lowe/dp/B000I8HIM2