Crazy Money With Paul Ollinger

Would you consider yourself a success if you died with $1 million? How about $10 million? Well, what if you died with $0.00?  In his new book, Die With Zero: Getting All you Can from Your Money and Your Life, Bill Perkins challenges you to flout conventional wisdom and spend your money not just before you’re dead, but while you’re still young enough to enjoy it. That’s right, instead of maximizing your net worth at death, he wants you to die having lived a life rich in experiences that your hard-earned money made possible. And he’s not saying you should blow it all on parties or ignore the needs of your kids or charities. He’s just saying that the time to decide how to best invest, spend, gift, or bequeath your fortune--big or small--is while you are still on this side of the dirt and still mobile enough to enjoy it. After all, travel is no fun when you’re too infirm to explore and savor the local culture. So dither not! There will be plenty of time to watch Family Feud and The Price is Right when you’re 87 a

Kirkland Hamill’s grandfather was very rich. His mother and father raised him and his brothers in grand fashion until Grandpa's death exposed major cracks in the family fortune. When his dad left his mom, she took Kirkland and his brothers to Bermuda where they attended a prestigious school, but never knew how they were going to pay for groceries.  In his first book, Filthy Beasts, Kirkland tells the story of a youth spent in flux between affluence and the alcoholism that came with the country clubs and yachts of his early childhood, and the deprivation and calamity of the years beyond that. The book is sad but immensely engaging and full of stories that will leave you gobsmacked. For example, because life in his mother’s home was chaotic, he decided he’d attend boarding school at Andover (as one does when they can’t afford milk) and then attend college at Tulane. The whole story makes you wonder what the point of money or status or social standing is if when one can’t — or chooses not to — provide a stable,

Ken Rusk has made a very good living by working with his hands. A true-life, self-described “ditch-digger,” Ken is an entrepreneur who has over 200 people working on his team. In his new book, Blue Collar Cash: Love Your Work, Secure Your Future, and Find Happiness for Life, Ken advocates an alternative career path to anyone who doesn’t believe “college + white collar job” is the route for them.  Ken doesn't believe that university life is wrong for everyone, but he argues that society over-emphasizes the necessity of getting that degree regardless of the massive tuition and debt millions take on in pursuit thereof. Happiness, he argues is in finding work that suits your skills and personality. That’s the situation in which one will find comfort, peace and freedom (not to mention financial security) in one’s career.  In this week’s episode of Crazy Money Paul and Ken discuss work ethic, the true sources of happiness, and career satisfaction. Special guest-host: Steve Sidles (Paul’s father-in-law who, unlike h

Barry Schwartz is the author of several books, including Why We Work and The Paradox of Choice. I spoke to Barry about his findings in these two important books.  Why is it that the harder we work and the more affluent we become, the more depressed we get? Prevailing social wisdom is that more is better, and that more choices should yield more satisfaction, but that is not the case at all. More choice not only overwhelms us, it raises our expectations and makes us doubt our decision-making. Too much choice doesn’t just not make us happier, it increases our anxiety and makes us less happy.  Could it be, even in our freedom loving country, that we have gotten too much of a good thing? That we would actually benefit from some guardrails in our lives? I’m sure there are those who would argue against it, but Barry’s research and conclusions here are quite persuasive.  Barry Schwartz taught psychology at Swarthmore College for 45 years and is now Visiting Professor of Management at UC Berkeley’s Haas School of Busi

My dad died peacefully at his home last Friday. He left this world with a clear conscience while napping in his favorite recliner and surrounded by loved ones. He was 93 years old. If you’re looking for guidance on how to lead a good life, Dad was a pretty good example. In this interview from 2019, we discuss work, money, saving, and family, but all these are really just a coded way to answer the question, “what is most important in your life?” For Dad, it was faith, family, and security, which meant always putting himself second while providing everything his family needed and forgoing most discretional material acquisitions.  Dad eschewed luxury, living simply and well within his means. Eminently frugal and practical, he had few wants other than to be faithful, useful and kind. While a devout Catholic, he also demonstrated traits of the most practiced Stoics and Buddhists. He wanted little, maintained self-control and practiced moderation in both consumption and emotion. He enjoyed whatever beer was on sale

Chris Hogan is a retirement planning expert and popular financial media personality. A former college football player who once worked as a bill collector, Chris has seen the pain economic mismanagement can wreak on a family. Since 2005, he has worked with personal finance legend, Dave Ramsey at Ramsey Solutions to fulfill his goal of helping as many people as possible achieve financial autonomy. Via The Chris Hogan Show and his two books (Retire Inspired and Everyday Millionaires) Chris has helped millions not just understand retirement, investing and building wealth, but to put in place plans to achieve their goals.  In our brief but rich discussion, Chris and I discuss the importance of creating a vision for a post-work life, how to control our spending, and what can be done to help close the racial wealth divide. Btw, one way Stacey and I are helping to address this important problem is by supporting Year Up, a national job training program that helps ambitious, hard-working young adults acquire the skills

Making a living in the arts is brutal. One of the things artists have to learn to do is manage their money and to structure their lives so that they’re doing the kind of work they WANT to do instead of doing work they HAVE to do just to pay the bills. On this week’s episode, Kyle Kinane shares insights into his comedy career and spending habits that have kept him solvent and relatively stress-free during the quarantine. While many artists are scrambling to earn while clubs are closed, Kyle maintains his creative freedom and sense of calm, partially because he never bought a Porsche.  Kyle Kinane is a nationally-headlining comedian whose TV appearances include Comedy Central’s Drunk History, This is Not Happening, and Comedy Central Presents half-hour comedy special. He has also performed live on the TV on Conan and The Tonight Show with Jimmy Fallon, among many others. As an actor, he plays a coke-head ex-boyfriend in Judd Apatow’s Netflix series, Love and also appears on TruTV's Those Who Can’t. His new albu

Are you an airline that dominates all the flights at a particular airport (e.g. Delta in Atlanta)? Are you a global beer conglomerate that controls half the beer brands on the planet? Or, are you a gloomy corporate type that owns half the funeral parlors in America? If so, then YOU might be an oligopolist.  No, this isn’t a new Jeff Foxworthy routine with a decidedly Econ 101 vibe—it’s a conversation with Denise Hearn (co-author of The Myth of Capitalism: Monopolies and the Death of Competition) about the limits of competition in our market economy.  How does this relate to money and happiness? Well, it’s yet another gut-check for us to examine the world in which we live and to question the narratives that drive our lives. Is America really a meritocracy? Are our markets really free? Is Paul's success a product of his hard work or the result of having truly fabulous hair? If nothing else, asking these questions will make us more aware of the forces that shape our lives, for better or worse. Also, you’ll get t

A fun (and sometimes funny) conversation about frugality? Heck yes, friends, because this is Crazy Money! Emrys Westacott is the author of The Wisdom of Frugality and professor of Philosophy at Alfred University. In addition to courses on ethics, happiness and logic, Emrys teaches an Honors seminar called Tightwaddery, or The Good Life on a Dollar a Day in which students hunt for bargains at yard sales, cut each other’s hair, and cook a banquet composed of meals that cost about a dollar to prepare. One student’s recipe was called “Apple Crisp and how to pilfer your ingredients from the dining hall (which suggests she might not have gotten an “A+” in Emrys’ Ethics class). The Daily Beast named Tightwaddery one of America’s “Hottest College Courses” and CNN called it one of “22 Fascinating and Bizarre College Classes.” Emrys' work on the topic of frugality centers around a few important questions: What does it mean to live the good life? Can frugality actually make you happier? And--while we’re at it--what does

Oliver Burkeman is the author of The Antidote: Happiness for People Who Can’t Stand Positive Thinking. He also writes a column for The Guardian called This Column Will Change Your Life in which he explores psychology and wellbeing.  When I first learned of the title of his book, I wasn’t yet familiar with Oliver’s work and I didn’t really know what it was about. But I knew it was for me, and I wasn’t disappointed.  In The Antidote, Oliver explores the true sources of human happiness as laid out in Buddhism, Stoicism, and modern psychology. He not only debunks the notion that relentless positivity makes the practitioner happier, but argues persuasively that the accompanying expectations make the happy, go-lucky visioneers much worse off. He offers a second path toward contentment that has to do with recognizing and accepting the scarier parts of life. (I am tempted here to write something here like "Up with Realism!!! Up with Uncertainty!!! Up with embracing our mortality!!!! … but as a realist myself, I don’

What if you get everything you’ve ever wanted and it’s still unfulfilling? What then? Men’s coach Tripp Lanier is the author of the newly released, This Book Will Make you Dangerous: The Irreverent Guide for Men who Refuse to Settle. Since 2005, Tripp has spent thousands of hours coaching people on how to get out of the rat race and align their work with their personal values. Over the years, he’s designed several businesses to support a simple lifestyle focused on freedom, aliveness, fun and love.  Do you think that’s really possible? To live and work on your own terms? Even if you thought it was possible, would you even know where to start?  Tripp started with himself — he designed his personal and professional life to get the most out of every day. He has engaged in everything from 10 day silent meditation retreats to “plant medicine” journeys to men’s groups in the Coast Rican Jungle. He was an early podcast pioneer in 2008, launching The new Man Podcast: Beyond the Macho Jerk and the New Age Wimp, which

At 23 years-old, Michael Brody-Waite drank a fifth of vodka and a 12-pack of beer everyday. He smoked tons of weed and cigarettes, and would “do any drug he could get his hands on.” When he wasn’t throwing up blood, he was mooching off--or just stealing from--his friends.  After finally getting clean, Michael achieved tremendous success in technology sales and eventually became the CEO of a health-tech start-up that sold for many millions of dollars. In his new book, Great Leaders Live Like Drug Addicts: How to Lead like Your Life Depends on It, Michael discusses the importance of living "mask-free" (he acknowledges the irony of advocating not wearing a mask during the pandemic), i.e. to live and lead with honesty and vulnerability. While this podcast isn’t really about leadership or entrepreneurship, I wanted to talk to Michael because the lessons he shares in his book are worth implementing in all of our daily lives. Speaking of the book, when I started reading it, I had my antennae out for self-help or mot

In 2013, Julie Saxon’s career was rocking along. The mother of two young girls had just gotten a big promotion, and was managing the work-life balance quite nicely. Later that year, everything changed when her husband, Joel, was diagnosed with stage 4 colorectal cancer cancer. Thus began a six-year journey trek through chemo, surgeries, hospital bills, insurance hell, and trying to keep the train on the tracks at work and at home.  After 6 years, 87 rounds of chemo, ten rounds of radiation, seven surgeries, and two clinical trials, Joel’s valiant fight against cancer ended in his death. He lived longer than 99% of patients with his diagnosis. While I was listening to her tell the story, I couldn’t help but think how much Julie’s strength, support, and raw will had to do with his relative longevity. Julie and I met when we both worked in ad sales at Yahoo! in the early 2000’s. She was in the Atlanta office where I would visit from the West Coast when I was home seeing my parents. Her story reminded me of how l

Why are some millionaires miserable while many in poverty are happy?  Does a rapidly-improving economy always lead to more well-being? How does optimism affect our economic futures? These are some of the big questions Carol Graham has tackled in decades of extensive research into the economics of happiness. A Senior Fellow at the Brookings Institution and Professor at the University of Maryland's School of Public Policy, Carol’s books include Happiness around the World: The Paradox of Happy Peasants and Miserable Millionaires and The Pursuit of Happiness: An Economy of Well-Being, both of which have been published in several languages. The economic factors that lead to happiness are often not what we humans believe them to be. Carol has spent her career challenging assumptions about how hope, uncertainty, optimism, inequality, and rapidly developing economies contribute to well-being. Her results, which are often counter-intuitive, are a great reminder of what we should keep in mind when trying to optimize

Paul Sullivan writes the Wealth Matters column for The New York Times and is the author of The Thin Green Line: The Money Secrets of The Super Wealthy. In his book, he discusses the important difference between being rich and being wealthy. Hint: One means that you have a lot of money, the other means that you have control over your financial life. Paul grew up in a working-class family but won a scholarship to attend an elite boarding school, an experience that changed his life. After earning degrees at Trinity College and University of Chicago, he began a journalism career, reporting for Bloomberg, The Financial Times, and other top publications. In this conversation, Paul shares how his experience growing up in a cash-strapped home both drove his fascination with people of means and molded his personal financial values. Through his reporting on and interaction with the wealthy, Paul has garnered insights into their hopes, dreams, and anxieties. He understands their spending, saving, and investing habits. H

Wealthy families have huge advantages when it comes to playing the college admissions game, and it’s not just more AP classes and $400/hour SAT/ACT tutors. That’s the conclusion of Paul Tough in his most recent book, The Years That Matter Most: How College Makes or Breaks Us, which Ira Glass describes the book as, “Gorgeously reported. Vividly written. Utterly lucid.” (such an "Ira Glass" way to say it.) Tough reveals that Cash-strapped universities actively seek out prospective students whose parents can pay full tuition. Thus, despite the ongoing discussion about preferential treatment for minorities and underprivileged families, schools’ thirst for cash flow results in far more lenient criteria for the children of affluent parents. In other words, it’s better to be a dumb, rich kid than a smart, poor kid, even though less well-off students at good schools have very similar outcomes than their more affluent classmates. Said one admissions counselor of the struggle to meet her school’s tuition (i.e. revenue)

Rabbi Daniel Lapin believes that money is the reward we get when we serve another one of God’s children. Therefore, doing business is doing God’s work. In his videos, courses, and books, Thou Shall Prosper and Business Secrets from the Bible, Rabbi Lapin leverages scripture to weave a passionate and refreshing defense of capitalism. In short: God wants man and woman to be together, to serve one other, and to prosper as a result.  In addition to capitalism, Rabbi Lapin and I discuss Evangelicalism, the Prosperity Gospel (which he completely disavows), the respective financial attitudes of Protestants v. Catholics, and—yes—why Jews are disproportionately good with money. Full-disclosure: I may be a biased participant in this conversation because the two best financial days of my life were the days I met the late Dave Goldberg and the day I met Mark Zuckerberg. Suffice to say that I have benefitted tremendously from my association with The Tribe, even if I once made a tragic sartorial decisions at a Bat Mitzvah

Laura Delizonna, PhD is a Stanford University instructor, international speaker, author, and expert on the science of happiness. Her mission is to help others thrive in life and work. She delivers practical, interactive, science-based trainings and inspiring keynotes. She consults with top corporations like Google and Facebook to help optimize team performance. On today’s episode, we talk about happiness, being yourself at work, the relative importance of income, and how to find joy in the everyday. If you don’t know about the human negativity bias (you have one), you owe it to yourself to listen...lest you succumb to your fear, anxiety and disappointment. You don’t want to do that, do you? No, of course not. So listen, and share with all your friends.  Learn more about Laura on https://delizonna.com/. To find books by Laura and other authors who have been on Crazy Money, shop our store on BOOKSHOP. (CM earns a small commission.) Find out more about Paul Ollinger on his website and/or follow him on the social

James H. Lowry grew up in Jim Crow era Chicago. After graduating from Grinnell College and spending time in the Peace Corps, Jim became McKinsey & Company's first African-American consultant in 1968 and, years later, the first black senior partner at Boston Consulting Group (BCG). Jim worked with mayors, the federal government and leading corporations to implement ground-breaking and historic workforce and supplier diversity programs. Lowry continues to serve as a senior advisor to BCG, while heading his own private consulting firm, James H. Lowry & Associates. His new memoir, Change Agent, chronicles Jim's amazing life. As impressive as his professional resume is, the stories he has about his youth, college years and his work in the Peace Corps will blow your mind. Jim’s not only smart, incredibly accomplished, and networked out the wazoo, but he is just one cool guy. Special thanks to my friend and former Facebook colleague, Kay Madati for the introduction to Jim.  Buy Jim’s book, Change Agent,here.  To fin

Michael Arceneaux is the New York Times best-selling author of I Can’t Date Jesus and his new collection of essays, I Don’t Want to Die Poor, in which he chronicles the debilitating nature of his student debt. A graduate of Howard University who is known for his biting wit and cultural insights, Michael’s writing appears regularly in top publications, including NYT, Washington Post, Esquire, Rolling Stone, Wired, The Atlantic, and many more. We spoke over Zoom from his apartment in Harlem where he is sheltering in-place. Buy his new book here. Read Paul Ollinger’s latest essay, Your Only Goal is to Arrive: To Survive the Quarantine, Change Your Metrics on Medium:Forge. Find out more about Paul Ollinger on his website and/or follow him on the socials: • Twitter: http://Twitter.com/Paul_Ollinger • Instagram: https://www.instagram.com/paul_ollinger/ • Facebook: https://www.facebook.com/PaulOllinger/ • LinkedIn: https://www.linkedin.com/in/paulollinger/