Crazy Money With Paul Ollinger

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 selling over 500,000 copies, they never recouped the expenses that went into the recording and production of music videos they weren’t really all that into in the first place. Despite the ups-and-downs, Kevn told me he has never been happier than he is now because he does what he does for himself and doesn’t worry too much whether other people like it. Kevn remains a prolific and respected songwriter and tours constantly. Over 38 years playing together, the band has “survived the pressures of fame, a shifting musical landscape, multiple lineup changes, and miles of backroads and highways” to arrive where they are “comfortable with their past and confident in their fu

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 residents go to college and the professional world. Before hooking up with Gladwell and Pushkin, Justin was a producer for NPR’s flagship news program Morning Edition then became an arts reporter for the network. He began his career as an intern for The Tavis Smiley Show and Smiley & West. Despite not graduating from high school, Justin earned a B.A. in philosophy from the University of California, Berkeley, and a master’s degree from the Berkeley Graduate School of Journalism.

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 begs the question, “just what are you buying for your private school dollar?” On this week’s episode, Paul talks to three good friends and fellow parents to discuss how they think about the private v. public school decision. Each of them has experience parenting in both public and independent schools in Dallas, Los Angeles, and Atlanta respectively. Thank you to P.J. Brady, Charlene Fitzgibbon, and Abigail Land for their time, candor and good humor. 

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 attempt to do so just leaves us miserable and isolated. Soone of the keys to productivity is deciding what to ignore. Further, Oliver reckons, when you put your existence into the context of the enormity of the universe, you realize that many of our “plans” are just distractions from the knowledge that we will all eventually be dead and won’t be remembered for terribly long. So why shouldn’t we just spend our days taking hikes and cooking for our children? Hey, that’s not a bad question. Sign up for Oliver’s newsletter here. Listen to Monty Python’s The Galaxy Song here. 

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 it is a fundamental way to take control of their health, well-being, and finances. Not only that, but cooking is a social and enjoyable act of service and love, and one of the things that make humans unique. In this conversation, Frankie and I discuss:  The benefits of attending boarding school What it was like to work with Mario Batali  His thoughts on Netflix’s The Menu and Hulu’s The Bear  His favorite books on food and cooking The essential basics to outfit a kitchen Whether organic food is worth it Check out the new season of Struggle Meals here ! 

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 like going to Cracker Barrel, flying Southwest Airlines, renting a car, or taking the bus. I (Paul Ollinger, hoster of show / writer of episode notes) find her videos hilarious. Leah was in Atlanta last week for a sold-out show at City Winer. She was kind enough to come by the house to chat money, success, and the very odd jobs that helped her pay the bills as a struggling actress. A native of Cincinnati, Leah began performing improv in New York City after graduating from Sarah Lawrence College. Her work has taken her to the Edinburgh Fringe Festival. New York Sketchfest, and the Los Angeles Comedy Festival. She has appeared on HBO’s hit High Maintenance and IFC’s C

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 investing, it’s really about how knowing what you want from life will help you make better decisions about money. I really enjoy Morgan’s writing and found the book to be an elegant summation of many of the things I want to discuss on this show. This episode was originally posted in October, 2020. 

Do women find men in expensive cars more attractive than men in less expensive cars? Some people believe that the answer to this question is so patently self-evident as to not require any thought. But my guest today conducted actual scientific research into this age-old stereotype. Rob Searle is a Welsh psychologist who co-authored a paper evaluating the status-enhancing effects of luxury vehicles on the attractiveness of both men and women to heterosexual members of the opposite sex. He asked participants to rate the attractiveness of an average looking man, first in a Bentley Continental GT, then in a much more modest Ford Fiesta. The findings were published in the British Journal of Psychology. And he discusses them in this episode of Crazy Money. The results build on the work of David Buss and others who found that perceived affluence does influence mating patterns.

This week, Paul reads some of the recent essays from his Substack. In "Why Talking About Money and Happiness Matters” he reflects on the reasons Bono, Jonah Hill, and Brian Cox have all, in the past few months, engaged in public discussion on the nature of success and what it can and can’t do for us. In "Lessons from a Freshman Pimple,” Paul recalls the devastating experience of an early high school face blemish and why seeking others’ approval can lead us to bad decisions. In "The Real Reason They Call it F-You Money,” he describes the mind games new money plays on its owner and why we must understand how money can help us get what we want from life (and not the other way around). ✍

Julie Saxon is the mother of two and a senior media executive. In 2013, her life was upended when her husband, Joel, was diagnosed with stage IV colorectal cancer. Thus began journey during which she had to keep the train on the tracks at work and at home while helping Joel fight for his life. But after 6 valiant years, 87 rounds of chemo, ten rounds of radiation, seven surgeries, and two clinical trials, he lost that battle. Joel lived longer than 99% of patients with his diagnosis, and—as I was listening to Julie tell the story— I couldn’t help but think how much her strength, support, and raw will had to do with his relative longevity. Julie and I met when we both worked in advertising sales at Yahoo! in the early 2000’s. Her story reminded me of how lucky we both were to work at a company staffed by so many incredible human beings. To this day, her Atlanta co-workers remain some of her closest friends. Not only did one of those colleagues introduce her to Joel, but he and the others were there to support

This episode is about working for fun, love, and legacy. Peter Gladstone is the Co-founder of Mass Hole Donuts, bakers of gourmet donut holes that celebrate the people, traditions, and spirit of Boston and Massachusetts. After 20 years in consumer marketing with companies like Gillette, P&G, and the Boston Beer Company (aka, Sam Adams), Peter retired and is now building Mass Holes because, he says, it’s fun, and he wants to contribute to the culture of his hometown. When he’s not establishing his Boston institutions, he is a Senior Advisor at the Harvard Innovation Labs where he advises consumer-facing ventures. Peter and I (Paul, host of show and writer of notes) were classmates at Dartmouth’s Tuck School of Business. That is where I developed my appreciation for his creative mind and wacky and wicked good sense of humor. We talk about the difference between working to pay your bills and working on a passion project, the role of humor in the corporate world, how he and his team survived pandemic, and how he

Nicole Lapin is the New York Times best-selling author of Rich Bitch, Boss Bitch, Miss Independent, and Becoming Super Woman. A summa cum laude graduate of Northwestern University’s journalism school, she became one of the youngest anchors in CNN’s history at age 21. In this episode, we discuss her parents’ rancorous divorce, her dad’s death by overdose, and the resulting financial turmoil that set her on a mission to help women have more financial literacy and empowerment in their lives and relationships. LINKS 

Larry Thompson is an entertainment manger in Beverly Hills, CA. In his 50+ years in Hollywood, Larry has guided the careers of over 200 stars, including Drew Barrymore, William Shatner, Cicely Tyson, Joan Rivers, Sonny & Cher, David Hasselhoff, Barry White, and Cindy Crawford. Larry grew up in Clarksdale, MS, graduated from Ole Miss law school then drove across country to chase his dream in Hollywood. As a young lawyer at Capitol Records, he helped negotiate the break-up of the Beatles then proceeded to sign each of the Fab 4 to their own solo contracts. This is just one of many incredible stories Larry shares about the talent he’s worked with, including George Harrison, Barry White, Elton John, Farrah Fawcett, and Lee Majors. We also discuss how Larry helps talent see their own potential, avoid pitfalls, and how Larry got his own act together when success and ego distracted him from what was important in life. Larry is the recipient of the Heller Award for Lifetime Achievement from the Talent Managers Associ

A year ago, Katherine Blanford was working as a nanny by day and doing comedy at night. Last summer, she made her network television debut on The Tonight Show with Jimmy Fallon and is now headlining around the country and opening for David Spade. She and I discuss the experience of having "heat" and cash in her pocket for the first time. We talk about artistic envy, the work ethic needed to succeed in comedy, what she learned about wealth and careers while working as a nanny, and of course, how much she loves the Ollinger family basement. 

Hey everybody. Happy 2023! This is a short, lightly edited greeting from Paul /me about where the podcast has been in 2022 and where we're going to take it in the year to come. I am grateful for your continued support and interest. I wish you and your family a safe, prosperous, and fulfilled year. Carpe Diem! ✍️ Subscribe to Paul's Substack newsletter here.✍️

The philosophical martial artist and actor, Bruce Lee is supposed to have said, “So you think, so shall you become.” On this week’s episode, we explore the power of positive expectations with David Robson, an award-winning science writer and author of the new book The Expectation Effect: How Your Mindset Can Change Your World. As you’ll hear, David makes a strong argument supporting Bruce Lee’s message: that positive expectations can meaningfully improve our lives. To be clear, this is not about the Law of Attraction. Robson bases the book on data gleaned from the scientific method. These studies provide ample evidence that our expectations can make us healthier, smarter, and significantly improve our aging prospects. (For better or worse–well, worse–the opposite is also true.) It’s important to note, as Robson and I discuss, that your expectations don’t just change your world. They also change the lives of others because our expectations of them–and theirs of us–have an impact on our respective lives. So we

Kristin Keffeler is the author of a new book called The Myth of the Silver Spoon: navigating family wealth and creating an impactful life. Kristin is also the founder of Illumination360 where she works with ultra high net worth families, including many worth billions of dollars. Her specialty is helping the rising generations create their own identities having grown up with extreme family wealth. In this conversation, Kristin and I talked about how her own family's affluence led her into this field; the specific doubts and fears that teen and adult inheritors of generational wealth have to deal with. We talked about the negative messages that society sends to wealthy children, about the balance rising generation members must strike owning their family name, but creating their own. We talked about how all parents—especially wealthier ones—can model financial behavior for their kids. And lastly, we discuss what the NFL Hall of Fame can teach us about the likelihood of measuring up to our wildly successful paren

Richard Reeves is a senior fellow at the Brookings Institution and the author of a new book called Of Boys and Men: Why the Modern Male Is Struggling, Why It Matters, and What to Do about It. You might ask, “Why is this topic relevant to Crazy Money, a podcast about money and happiness, work and meaning?” Because the connection between education, gainful employment and life satisfaction is massive. And on these metrics, the modern male is not doing well. Consider some of these data points: Boys are 50% more likely to fail classes in math, reading and science than girls. By High School, 2/3 of the students in the top 10% of the class ranked by GPA are girls, while about 2/3 of the students in the lowest 1/5 of the class are boys. And education matters. One in three American men with only a high school diploma (10 million men!) are now out of the labor force. They're not unemployed–they're out of the labor force. They're not even counted in the unemployment numbers. And this matters because men without educatio

We don't think about it all the time, but BELONGINGNESS is the third most fundamental desire on Maslow’s Hierarchy of Needs. Just above safety and physiological requirements, is our need to feel safe as part of a tribe. My guest this week is Geoffrey L. Cohen, the author of Belonging: the Science of Creating Connection and Bridging Divides. Geoff is a professor of Psychology and Organizational studies at Stanford University in Palo Alto, California. In this conversation, he and I talk about what it means to belong to a place, an organization, a family or a movement; We explore how belongingness and identity are intermixed, and what implications that has for discussing politics and other beliefs with people who have differing points of view. We talk about how to design diversity training so it doesn't alienate half the room (maybe we should call it “Belongingness Training”). We also talk about what groups you'd rather not belong to, because while belongingness is important, some tribes are better than others!

Former hedge fund manager Hugh Hendry grew up working class in Glasgow, Scotland. His anxiety, detachment from money, and passionate observations of life led him to hypotheses and market positions others couldn’t see. In 2008, when the rest of the world was melting down, Hugh’s Eclectica Asset Management returned over 30%. As great as the money was, he says what drives him is a profound need to be loved. Today, Hugh develops property in St. Barths where he lives full time. In this conversation, Hugh shares anecdotes of Scottish thrift that will make you laugh, an honest description of how it feels to lose millions of other people's dollars, why closing his hedge fund felt “as if you've died in Mortal Kombat,” and why we should all be mindful of “the profound wrongness of today.” We spoke at the Stansberry Research conference in Boston in October.