Reasonably Happy with Paul Ollinger

Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at Stanford University, where she went on to win both individual and team national championships and became Nike Golf’’s very first NIL sponsored athlete. But when the time came to turn pro, Rachel decided that a life on the road and in the spotlight wasn’t for her. Instead, she earned and accepted her commission as an officer in the U.S. Air Force Reserve. I was very pleased to speak with Rachel, not just because she is a young woman of exceptional talent and character, but because she is also the daughter of my Rhodes College friends, Stacy and Robert Heck. She and I discuss her journey (so far), particular: -Struggling with perfection -The true definition of success -The importance of motherhood -How her dad “Pavlov’ed” her and her sisters into loving golf -The importance of role models, including: Condolleezza Rice (her academic advisor), Annika Sörrenstam, and Stanford Coach Anne Walker -Her favorite (and second favorite) golf course! ✍️Please rate and review Reasonably Happy (⁠https://ratethispodcast.com/paulopod⁠) ✍️ 👊Get Paul’s Substack newsletter (⁠http://words.paulollinger.com⁠) 👊

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) 👊

Ed Latimore, a former professional boxer with a degree in Physics, shares gripping stories from his memoir, exploring themes of discipline, self-mastery, and emotional control. He discusses how his challenging upbringing shaped him and the importance of providing a loving environment for his son. Ed emphasizes the significance of sobriety in nurturing his relationships and advocates for forgiveness as a powerful means of personal freedom. With a mission to inspire youth, he reflects on the lessons learned from his life and boxing journey.

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/