Reasonably Happy with Paul Ollinger

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.👀 Follow Paul on Instagram here  👀🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤About Crazy Money:Unlike traditional personal finance or investing shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

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. 🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤About Crazy Money:Unlike traditional personal finance or investing shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

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. 🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤This episode was originally posted in August, 2021About Crazy Money:Unlike traditional personal finance or investing shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano Are you really still reading?

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 ! 🍲🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤About Crazy Money:Unlike traditional personal finance or investing shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society. Status.Crazy Money is edited by Mike CaranoAre you really still reading?

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 Commuters.👩‍🦰Follow Leah on Instagram👩‍🦰🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤About Crazy Money:Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Money is not about how to make a million bucks, how to beat the market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society. Status.Crazy Money is edited by Mike CaranoAre you really still reading?

Author Morgan Housel shares insights on the psychology of money, including managing expectations, prioritizing personal fulfillment, and the significance of soft skills in investing. The podcast also discusses the Collaborative Fund's focus on doing good, the influence of personal goals on financial decisions, and the importance of choosing one's own financial game. Additionally, it explores the role of financial advisors as financial psychologists and the impact of income inequality on the American economy.

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.🔥 Read Paul’s Substack here 🔥🎤 See Paul’s upcoming shows here 🎤🔗Connect with Rob Searle on LinkedIn 🔗🚗 Summary of the study can be found here 🚗About Crazy Money:Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Money is not about how to make a million bucks, how to beat the market, or how to save money by switching cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society. Status.Crazy Money is edited by Mike CaranoAre you really still reading?-- Read my newsletter Money and the Meaning of Life here.

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).✍🏻 Subscribe free to Paul’s Substack here. ✍🏻📷 Follow Paul on Facebook here. 📷🤣 See Paul’s world-changing comedy on Instagram here. 🤣

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 her throughout marriage and its sad conclusion. Julie is now Chief Revenue Officer for a large digital media company. She and her two beautiful daughters live in Atlanta. I want to thank Julie for trusting me with this conversation. This episode was originally released in June, 2020. ✍🏽 Read Paul’s Substack here. ✍🏽🎤 See Paul’s upcoming comedy shows in Charlotte, Chattanooga and more here. 🎤🩺 Get screened for colorectal cancer. 🩺

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 defines success now that he has “enough.” ✍🏽 Read Paul’s Substack here. ✍🏽🎤 See Paul’s upcoming comedy shows here. 🎤🍩Visit Mass Hole Donuts website here. 🍩🍪 See Mass Hole’s Instagram here. 🍪