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Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surroundi ...
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Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his start selling Bibles door-to-door then went on to develop and sell > $3 billion in resort real estate over the next few decades, including Hampton Island, GA whose residents include Ben Affleck / Jen…
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Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times best-selling author of several books, including 'For You When I Am Gone’ and 'The Beauty of What Remains,’ both of which pertain to death and dying. I had planned on speaking with Steve primarily about…
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Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, The Monk Who Sold His Ferrari, The Everyday Hero Manifesto, and Who Will Cry When You Die?, Robin has a new book out called The Wealth Money Can’t Buy in which he examines the ways we can all develop h…
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Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience through “the fascinating world of democracy, politics, and history.” In the process, she is proving that Americans—and other good people around the globe—are hungry for unbiased political co…
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Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his gift for mathematics landed him a spot at London School of Economics (alma mater of Mick Jagger, Margaret Thatcher, and George Soros) where he attended with the sons and daughters of the global …
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Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In this insight-rich conversation, Dr. Ramani explains the traits and behaviors of narcissistic individuals, how they hijack our well-being, and the motivations behind their attention-seeking b…
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Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues that YOU and I can improve the world by embracing our natural inclination toward generosity. He speaks not just of financial generosity, though that’s certainly a huge part of it, but also of creative g…
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This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip between San Francisco where Paul had just performed at Cobb’s Comedy Club and San Luis Obispo where he was heading to perform in the SLO Fest Comedy Festival. Among other things, Paul and Mike discuss: M…
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When John O’Leary was 9 years old, he played with fire and got burned. Like really, really burned, over 99% of his body. Doctors gave him less than 1% chance to live and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, survive he did. His journey back took years, requ…
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In this special “where has Paul been?” episode, Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Adventures in Affluence: Dry Cleaning - why Paul got freaked out when he starting thinking about how much he spends on dry cleaning every year…
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Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.” Coleman has a new book out this week called 'The End of Race Politics: Arguments for a Colorblind America,’ in which he confronts the "failed corporate diversity and inclusion efforts and poisonous race-b…
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Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of Boston College’s Center on Wealth and Philanthropy, Paul is the co-author of 'The Joys and Dilemmas of Wealth,' a 2010 report that is one of the most insightful studies of the ultra-affluent ever. We discuss…
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This is a special holiday encore of the 2nd episode of Crazy Money with Dr. Drew, which ran Jan 30, 2019. Dr. Drew offers candid insight into the ups and downs of a career in broadcasting and medicine. From Loveline to Celebrity Rehab, Dr. Drew has been a staple on radio and cable television for over 30 years, but that doesn’t mean he’s rich — he’s…
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Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like you…
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Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, directing, developing talent, and getting his family together for dinner. Judd has accomplished so much in his career that, in retros…
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Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you possess either an interest in finance or a robust / dark sense of humor, The Counting House will make you laugh and, at times, cry in …
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Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you find yourself at a crossroad? Today, I speak to innovation expert Merrick Furst about how seeing ourselves and the world more clearly can tell us how to move forward when the way isn’t clear. Merrick is a …
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In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Every Day Is Thanksgiving This One Question Will Help You Stop Comparing Yourself to Others Why the Jews? The holy roots of ant…
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✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ 🎤 See Paul’s upcoming comedy dates here and random thoughts on Instagram here. 🎤 Ed Begley Jr. has been acting professionally since 1967 when he appeared in an episode of My Three Sons. 56 years later, Ed has acted in hundreds of movies and TV shows, including An Officer and a G…
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✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ Jennifer Wallace is a journalist and author specializing in psychology, parenting, and health. Her new book 'Never Enough: When Achievement Culture Becomes Toxic—And What We Can Do About It' delves into our modern dilemma of busyness, achievement, credentialing, and status-seeki…
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Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the United States in the late 1970s and early’80s. Triumph was known for its BIG live shows featuring lights, pyrotechnics, and lots of spandex (as was appropriate for the era!). Along with Rik's bandmates Gil…
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When Daniel Carcillo played in the NHL, he was known as an enforcer so tough and volatile that he earned the nickname “Car Bomb.” In his 12 seasons in the NHL, Daniel was a member of two Stanley Cup-winning teams (2013 and 2015 Chicago Blackhawks), led the league in penalty minutes, and was fined or suspended by the NHL 12 times. He also suffered a…
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Over the past 30 years, Cal Fussman has interviewed a breathtaking array of the world’s most fascinating people, including Nelson Mandela, Clint Eastwood, Barbara Walters, Richard Branson, Muhammed Ali, Mikhail Gorbachev, Neil Young, Serena Williams, Tim Ferriss, Kobe Bryant, Al Pacino, Pelé, and hundreds more. He co-authored Larry King’s memoir an…
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Victor Haghani is the author of a new book called The Missing Billionaires: A Guide to Making Better Financial Decisions, which explores why family fortunes like the Vanderbilts' get destroyed in the hands of the heirs. Victor knows a lot about wild swings in wealth. As co-founding partner of the Long-Term Capital Management (LTCM), Victor saw the …
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Farnoosh Torabi is an Iranian American journalist and one of the country’s most trusted personal finance experts. In her new book, A Healthy State of Panic she examines the role fear can have in leading us toward the relationships, careers, and financial situations we are meant to have. For over two decades, Farnoosh has a strived to help people be…
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After 15 years of financial reporting, Ron Lieber reports that “No consumer decision inspires more confusion and emotion than the question of what to pay for college,” which is understandable since four years at many state schools now costs over $100k in tuition and four years of private school can run over $300k! The "Your Money" columnist for the…
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Kids who grow up in stable, two-parent homes are less likely to live in poverty, have behavioral problems, and get in trouble at school. They’re more likely to go to college, attain stable employment, achieve higher earnings, and to get married themselves. So reports Melissa Kearney in her new book The Two-Parent Privilege: How Americans Stopped Ge…
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Garrett Gunderson is a NYT best selling author and the funniest financial speaker you may or may not have heard of. The son of a Utah coal-miners, Garrett wants to teach others how to become financially independent and have a laugh along the way. He has written several money books, including Disrupting Sacred Cows, Killing Sacred Cows, and What Wou…
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In an automated world without constraints or time to think, our spending has been super-charged. Markets, apps, and e-commerce are all designed to separate us from our money as quickly and consistently as possible. So argues Julio Vincent Gambuto in his new book, Please Unsubscribe, Thanks!: How to Take Back Our Time, Attention, and Purpose in a Wo…
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“Parents Hire $4,000 Sorority Consultants to Help Daughters Dress and Impress During Rush” read the Wall Street Journal headline that nearly made my neck snap. As a middle-aged man whose kids aren’t quite college age, I was unaware of the #RushTok phenomenon on TikTok or the Bama Rush documentary that sparked a massive fascination with the sorority…
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The new Netflix series Painkiller is based on a book my guest, Barry Meier wrote over 20 years ago. In Pain Killer: An Empire of Deceit and the Origin of America's Opioid Epidemic, Meier explores how Purdue Pharma’s drug OxyContin catalyzed a plague of addiction and death that has destroyed families and whole communities across the country. Between…
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Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, including: Dare to Suck: What you can learn about improvement from acting coach Lesly Kahn and author Mark Manson The Secret to Being Very, Very Rich Nobody Needs a House with 8 Toilets 🔥Paul publishes these essays (about) every other Tuesday. You should subscri…
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If your new college grad son or daughter is unemployed, sleeping in their childhood bedroom, and watching All My Children every day, fear not - Laura Belgray has been there and she turned out okay. As Laura explains in her new, laugh-out-loud (LOL) funny memoir, Tough Titties: On Living Your Best Life When You’re the F-ing Worst, sometimes it’s goo…
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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 attorne…
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If you’re trying to hide assets from your spouse or soon to be ex-spouse, beware! Whether it’s Cayman Islands bank accounts, bearer bonds stashed in a safe deposit box, “hidden" real estate, or hundreds-of-thousands in Bitcoin, Nick Himonidis and his team at NGH Group will probably discover your secret stash. Nick is an attorney, Certified Fraud Ex…
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Having experienced divorce as the child of a wealthy family, Olivia Summerhill understands the massive impact parents fighting about money can have on their children’s lives. Today, Olivia provides financial consulting for ultra-high-net worth women going through divorce. Her typical client has a household net worth of $100mm or more, so she provid…
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Will Vogt is a photographer with a front row seat to the American upper class. Raised on Philadelphia’s Main Line, Will attended boarding school, and spent lots of time in the tony enclave of Watch Hill, Rhode Island where his family summered. His new collection of photography, These Americans, showcases decades of intimate snapshots of his social …
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Our higher education system is broken. But instead of trying to fix the underlying issues, the Biden administration is attempting to treat the symptoms with a massive giveaway to student loan debtors. In this encore episode (from August, 2022), I speak with Oren Cass. Executive Director of American Compass, whose article The Banality of Student Loa…
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If you find marriage to be hard, you are not alone. If you feel as if your spouse should fulfill every single physical, emotional, sexual, and financial need in your life, you probably should be alone. This week, I talk to Eli Finkel, author of the book, The All-or-Nothing Marriage in which he presents data and anecdote about how the best marriages…
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Turney Duff was making millions on Wall Street until cocaine addiction brought him to his knees. His book The Buy Side: A Wall Street Trader’s Tale of Spectacular Excess is a funny, horrifying, then hopeful read and a New York Times best-seller (you should buy it here). Paul and the esteemed author share a lot of laughs as they discuss what money m…
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For your summer listening while driving, walking, gardening, pleasure, Paul reads three of his latest pieces from Substack (Money and the Meaning of Life), including: How to Stay Hungry When Your Life is Full Money, Pain, and New Cars You Deserve It, i.e. reflections on what it means to “deserve” something Paul publishes these essays (about) every …
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Bruce Feiler is a seven-time New York Times best-selling author of books such as Life is in the Transitions, Walking the Bible, and The Council of Dads, Bruce's 2008 account of his battle with bone cancer and the contemplation that his then three-year-old twin daughters would grow up without a father. The book birthed a documentary hosted by Sanjay…
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Janny Scott is the descendant of railroad barons and financial tycoons. She grew up on an 800-acre estate on the Philadelphia Main Line. In her book The Beneficiary: Fortune, Misfortune, and the Story of My Father, she shares the details of both the opulence and the tragic complications of her family’s vast fortune. While things appeared perfect fr…
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Kevn Kinney is the lead singer of Drivin N Cryin, a rock band that achieved legendary status in the Southeast during the late 80s and 90s but never quite broke into the national big time. DNC’s popularity peaked when their album Fly Me Courageous was certified gold. During that time, the band toured with Neil Young and Soul Asylum, but even after s…
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Justin Richmond is the producer and co-host of Pushkin's music podcast Broken Record with writer Malcolm Gladwell and Def Jam co-founder Rick Rubin. He is also the host of a new podcast called Started from the Bottom on which he interviews mega-successful people who came from disadvantaged economic backgrounds and neighborhoods from which few resid…
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Annual private school tuition can run over $60,000 in big cities like New York or Los Angeles. But even in smaller markets like Atlanta, 14 years of private school (pre-k through 12th grade) will easily exceed half a million dollars. (And that doesn’t include the expected contributions to annual fund and capital campaigns!) This massive commitment …
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Oliver Burkeman is the author of 4,000 Weeks: Time Managment for Mortals, which Adam Grant calls “The most important book ever written about time management.” In it, Oliver argues that using your life (4,000 weeks = about 80 years) most meaningfully requires abandoning the illusion that we can—or should try to—get everything done. And that the atte…
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Chef Frankie Celenza started his culinary career with an illicit George Foreman grill in his prep school dorm room. Today, Frankie is the Emmy award-winning host of the Tastemade's hit show Struggle Meals. Frankie believes you don’t have to spend a lot of money to cook (and eat) well. He wants more people preparing their own food because he believe…
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Leah Rudick is an actor, writer, and comedian whose Wealthy Woman character videos have earned her almost one million followers on Instagram and TikTok. Thanks to her breakout social media success, Leah is now selling out comedy shows all over the country. In these videos, a clueless woman of wealth shares her point-of-view on everyday experiences …
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Morgan Housel is the author of the book, The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness. As the back cover of his new best-seller reads, “Doing well with money isn’t necessarily about what you know. It’s about how you behave. And behavior is hard to teach, even to really smart people." While the book is partially about in…
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