Crazy Money With Paul Ollinger

Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed about his new memoir, Hard Lessons From the Hurt Business: Boxing and the Art of Life in which he shares stories about discipline, sobriety, and self-mastery. Ed and I talk bout how emotional control can outpower ego, how true masculinity is rooted in accountability, and why forgiveness is the ultimate form of strength. He also discloses that he (loves and) likes his wife! Thanks to Rob Henderson for bringing Ed to my attention. ✍️Please leave us a rating : https://ratethispodcast.com/crazymoney ✍️

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 f

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, S

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

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 endeavo

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, s

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 ab

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 wil

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 Tea

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 nos

Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who discovered himself after years of addiction and psychedelics only to emerge on the other side as one of the funniest comedians working today and starring in the hit Off Broadway Steven Soderbergh show "The Fears".

Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize Your Full Potential. Scott’s writing dives deep into the psychology of the victim mindset, narcissism, and the impact of performative vulnerability on social media. Having overcome childhood misdiagnoses that placed him in special ed classes and bullying peers, Scott went on to earn a PhD from Yale. He shares this deeply personal story of as a teachable moment to discuss mental health, cancel culture, psychological flexibility, and what truly helps us grow as humans. Thought-provoking, funny, and brutally honest—this is a must-watch for anyone navigating identity, trauma, or the modern self-help world. Scott’s other books include Transcend: The New Science of Self-Actualization and Choose Growth: A Workbook for Transcending Trauma, Fear, and Self-Doubt. Read Paul’s Substack here: http://words.PaulOllinger.com Learn more about Scott’s academic on his website an

Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blackstone founder Stephen A. Schwarzman. Zibby shares how grief, motherhood, October 7th, and why it’s okay–great even–to marry the tennis pro! She shares how resilience shaped her path, from launching a award-winning podcast and starting her own publishing house to writing memoirs and novels. She reflects on growing up in privilege, breaking free from societal expectations, and using her platform to speak out about antisemitism in a world that is increasingly dangerous for Jews. Zibby’s story is a masterclass in reinvention, purpose, and creative freedom. Read Paul’s Substack: https://words.paulollinger.com/ Learn more about Zibby here - https://www.zibbyowens.com/

CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of American presidents. From Trump’s transactional pardons to the controversial case of Hunter Biden, Toobin offers sharp analysis, historical insight, and headline-worthy commentary. He discusses why Gerald Ford’s Nixon pardon was unnecessary, how the January 6th pardons expose Trump’s political strategy, and why public cynicism is fueled by elite immunity. Plus, Toobin opens up about his career, love for golf, admiration for Jim Gaffigan, and his obsession with Evel Knievel’s wardrobe. This episode delivers sharp wit, surprising revelations, and crucial context for anyone interested in politics, justice, or power. Follow Paul: https://www.instagram.com/paul_ollinger/?hl=en Check out Jeffery's book: https://www.simonandschuster.com/books/The-Pardon/Jeffrey-Toobin/9781668084946

Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A Stand-Up Comedy and a Skokie Elegy. Hirsch reflects on his chaotic upbringing in 1950s Jewish Chicago, his complicated relationships with his parents, and the wild characters who shaped his life. He opens up about the tragic loss of his son Gabriel, how grief became poetry, and why humor and heartbreak often walk hand in hand. From poetic craft and emotional truth to the role of art in a distracted world, this is a raw, funny, and deeply moving conversation about identity, creativity, and resilience. Follow Paul on Instagram: https://www.instagram.com/paul_ollinger/?hl=en Check out "My Childhood" in Pieces: https://edwardhirsch.com/ Audio excerpted with permission of Penguin Random House Audio from MY CHILDHOOD IN PIECES by Edward Hirsch, read by the author. © Edward Hirsch ℗ 2025 Penguin Random House, LLC. All rights reserved.

Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing policy scholar—explains why race-based affirmative action has failed America's working class and what can be done to fix it. A self-described “liberal maverick,” Kahlenberg dives into his controversial role in the Supreme Court case against Harvard, arguing that socioeconomic-based admissions would promote both racial equity and fairness without alienating the working-class voters Democrats are rapidly losing. From Harvard's legacy advantages and billionaire endowments to MLK’s and RFK’s forgotten views on class over race, this episode challenges elite institutions, political orthodoxy, and the future of education in America. Check out al of Richard's books and appearances: https://www.richardkahlenberg.org/ Get Paul's book: https://www.paulollinger.com/the-book

In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this week's Reasonably Happy podcast, Benson--who is now running for governor--joins Paul Ollinger to discuss how she modernized the DMV, what it feels like to be targeted by the President of the United States, and why the Democrats' murky future. Paul pushes her to take a stand against a party that keeps falling on the sword of cultural issues with which most of America disagrees, opening the door for the very President who tried to intimidate her. Unfortunately, Benson waffles on subjects like biological males in girls' sports and the fact that most college campuses have been captured by progressive ideology. Still, it's an interesting conversation with a rising politica

This week, Paul reads his three most recent Substack posts, including: A very funny take on Qatar's bribery of pretty much every institution in America, How his dog's feel about castration, and Why many of us will have our TikTok handles on our tombstones. Please join Paul's Substack family by following here: http://words.paulollinger.com . And, if you're so inclined, follow him on Instagram: https://www.instagram.com/paul_ollinger 00:00 Introduction to the Podcast and Substack 02:48 Exploring Qatar's Influence and Ethics 06:02 Proposal for a Qatari Comedy Club 08:57 Corporate Life Lessons from Dogs 12:00 Navigating Career Changes and Authenticity 18:11 The Impact of Social Media on Identity 23:10 A Humorous Obituary for the Future

He was drinking by age five, shuffled through ten foster homes, and emotionally shut down by the time most kids are starting kindergarten — yet Rob Henderson clawed his way from chaos to Cambridge. In this powerful episode, Rob, author of Troubled: A Memoir of Foster Care, Family, and Social Class, shares his incredible journey from trauma and addiction to earning a PhD from Cambridge University. He opens up about childhood instability, military discipline, elite university culture, and his groundbreaking concept of “luxury beliefs”—status-signaling values held by the privileged that often harm the poor. This conversation is raw, eye-opening, and packed with insights about resilience, class, and what truly shapes success. Check out Rob's Substack: https://www.robkhenderson.com/ Read Paul's Subtack: http://words.paulollinger.com Follow Paul on Instagram: https://www.instagram.com/paul_ollinger