Reasonably Happy with Paul Ollinger

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 from the outside, alcoholism, suicide, divorce, and idleness derailed many of her relations. In this conversation, we discuss what it was like to grow up on property the size of Central Park and how the presence of so much wealth affects her attitudes about money today. We also cover the tragedies that befell many of her ancestors as they struggled to find purpose amidst massive affluence. Janny worked for 14 years as a reporter for the New York Times where she was a member of the team that won the 2000 Pulitzer Prize for national reporting. Prior to the NYT, she reported for the LA Times and The Record of Bergen County (NJ). Her first book, A Singular Woman: The Untold Story of Barack Obama’s Mother earned her a nomination for the PEN/Jacqueline Bogard Weld Award for Biography and was named to Time magazine’s top ten nonfiction books of 2011. A graduate of Harvard College, Janny spoke with me from her home in New York City. This episode was released in October, 2020. 👀 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?

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 future.” I had a great time talking to Kevn in my basement where we discussed: Why we both don’t love jam bands How the song Straight to Hell went from being a “dumb song at the end of the record” to one he now has to play at every show Why, unlike a lot of musicians, he loves actually appreciates Spotify and iTunes The good part about touring at 62 How artistic envy keeps artists down Some of the bands he has loved working with over the years, including: the Black Crowes, Collective Soul, Indigo Girls, REM, Edwin McCain, Blues Traveler, and many more The difference between Atlanta and Athens, GA Big thanks to Michaeline and Ed Roland for connecting me with Kevn.  🎸See Kevin and the band’s live dates here.🎸 🔥 Buy Kevn's new album, Think About It here. 🔥  👂Listen to Paul’s Drvin N Cryin / KK playlist on Spotify.👂 👀 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?

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, 2021 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?

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 Carano Are 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 Carano Are you really still reading? Click the icon below to listen.

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 Carano Are 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. 🤣 Click the icon below to listen.