Reasonably Happy with Paul Ollinger

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 work and what we can learn from them. We discuss the evolution of marriage over the centuries, when and why love became part of the equation, how helping your spouse grow benefits you, the role of money in marriage, and why consensual non-monogamy will 99.999999999% for sure never happen in the Ollinger household. A survey of Eli's peers identified him as the most influential relationship scientist in the 21st century and the Economist declared him “one of the leading lights in the realm of relationship psychology.” On the other hand, his wife thinks it’s hilarious that he is a “marriage expert.” Learn more about Eli and his book 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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 meant to Turney as he got rich, got lost, got sober, then got published. This darn funny conversation covers everything Turney's middle school science fair fiasco to insider trading. Also, prostitutes. Find out more about Turney and hear the Galleon rap here. 

🔥 Follow Turney on Twitter 🔥 
 ✍️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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 other Tuesday.You should subscribe here. 🔥 Please feel no pressure to pay for a subscription, but do feel pressure to share his writing and this podcast with ALL of your friends. Also, you can also see where Paul (i.e. me) will be performing comedy here. 🎤 Shows coming up in Chattanooga, Charlotte, and Atlanta.

About Paul:
Paul Ollinger spent 15 years in sales leadership positions for Yahoo! and Facebook before bailing on the world of digital advertising to chase his comedy dream. He has headlined Carolines on Broadway, performed at legendary clubs such as the Hollywood Improv and the Comedy Cellar, and opened for everyone from Bill Burr to classic rock bands, Styx and Collective Soul. He plays comedy clubs, country clubs, and dirty bars all over the country. A graduate of Rhodes College, Paul earned his MBA at Dartmouth’s Tuck School. He lives in Atlanta with his wife, two tween kids, and French bulldog, Colonel Tom Parker. Follow him on Facebook. 

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 Gupta, a drama series on NBC, and a wildly popular TED Talk. In his new book, The Search: Finding Meaningful Work in a Post Career World, Bruce argues that the truths about work with which so many of us Boomers / GenX’ers were raised no longer apply and that today’s economy is “meaning based” as opposed to “means based.” We discuss what implications this has for employers, workers, and those of us trying to understand just what is going on out there. We talk about why Bruce dedicated the book to Pat Conroy, why that means something to Paul, how our expectations of a linear world and career stress us out and why it is critically important to “stop chasing someone else’s dream (or, in Paul’s case the approval of Sheryl Sandberg). Special thanks to 2x Crazy Money guest and occasional listener, A.J. Jacobs for connecting me with Bruce.

🔥 Visit Bruce’s website here. 🔥 
👀 Read Bruce’s Substack, The Nonlinear Life 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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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?

Get full access to Reasonably Happy at words.paulollinger.com/subscribe