Crazy Money With Paul Ollinger

Holly Parker is one of the most dynamic people I have ever met. A top NYC realtor who has sold over $8 billion in property, she is also a self-made millionaire, consummate connector of people, world traveler, twin mom, and author. In her new book, Back on the Market: A Realtor’s Guide to Love and Life Holly tells the story of her divorce, re-entry into the dating world as an ultra-successful woman, and how she earns the trust of billionaires who purchase $50mm+ apartments.  On this week’s episode Paul and Holly talk about the source of her (and to an extent, his) motivation: an anxiety born of wanting to be seen, liked, and respected. And about how she channels that energy to destroy her sales goals and give back to the world.  Learn more about Holly on her website. Buy the book here. **Please rate and review Crazy Money.** Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here. About Crazy Money: Unlike traditional personal finance shows,Crazy Money is not about how to make a mill

If you have kids in or nearing college age, you HAVE to listen to this episode. Ron Lieber’s new book, The Price You Pay for College contains critical, in-depth information about one of the most important financial decisions your family will ever make. After 15 years of financial reporting, Lieber reports that “No consumer decision inspires more confusion and emotion than the question of what to pay for college,” which is understandable since 4 years at many state schools now costs over $100k in tuition and 4 years of private school can run over $300k! Ron explains that not only is college ludicrously expensive, but the admissions process is purposefully opaque, so it’s hard to know if you/your kid will get in and whether or not you/your kid will be able to afford to go. By throwing himself head-first into this stormy, complicated sea, Ron helps the reader find the best college for them, pay the fairest price, and not destroy their family and finances in the process.  Ron Lieber is a proud alumnus of Amhers

Daniel Markovits is the Guido Calabresi Professor of Law at Yale Law School and the author of The Meritocracy Trap in which he outlines the price meritocracy imposes on society. In addition to severely limiting opportunities for the middle and lower classes, our knowledge-based economy “devours the elite” who work brutally long hours at top law firms, investment banks, and consulting companies. And Daniel would know. After all, he acknowledges that he is part of the system that he is criticizing. Not only does he train the attorneys that will go on to work themselves silly, but he holds an academic resume like none you have ever seen. Check this out: After earning a B.A. in Mathematics, summa cum laude (which is Latin for “way smarter than you”) from Yale University, Markovits received a British Marshall Scholarship to study in England, where he was awarded an M.Sc. in Econometrics and Mathematical Economics from London School of Economics and a doctorate in Philosophy from the University of Oxford. Markovits

William “Bill” Irvine is an author, philosophy professor, and an active investor who describes his intended audience as "intellectually-upscale readers who have a minimal background in philosophy but who are interested in carefully rethinking the assumptions of everyday life.” (Hey, that’s YOU!) Bill wants to make philosophy accessible and applicable to our everyday struggles. His research can best be described as hybrid, reflecting topics that lie on the border between philosophy and something else. For example, many of his articles address the ethical issues involved in finance. His first two books were on the ethical and political aspects of parenting. And his book, On Desire (one of the two we’ll discuss today), has a philosophical component, but also a scientific and religious component.  In our conversation, Bill explains our biological incentive systems, how our brains are like a Thanksgiving poultry trifecta, and why it’s imperative for each of us to develop a Philosophy of Life or a Grand Goal in Liv

Jesse Itzler only eats fruit 'til noon, loves Run-D.M.C., and enjoys living life "out of the box." The author of the New York Times bestseller, Living with a Seal, cofounded Marquis Jet, the world's largest private jet card company which he and his partner sold to Berkshire Hathaway/NetJets. Jesse then partnered with Zico coconut water, which he and his partner sold to The Coca-Cola Company. He’s a former rapper on MTV and wrote and performed the NBA's Emmy Award-winning "I Love This Game" music campaign and the popular New York Knicks anthem "Go NY Go." When he's not running ultra-marathons, eating vegan food or being a dad to his four kids, Jesse can be found at the NBA's Atlanta Hawks games, where he's an owner of the team. He is married to Spanx founder Sara Blakely Get the BYLR Radio app here. Get the most out of 2021 with Jesse’s Big Ass Calendar Club and follow him on Instagram. Join the Crazy Money Listeners Group here. Rate and review Crazy Money here. About Crazy Money: Unlike traditional personal f

The New Yorker called Princeton and University of Melbourne bio-ethicist, Peter Singer “the world’s most influential living philosopher." Time included him on its annual list of the world’s 100 most influential people. Peter has a question for you: Did you know that for the cost of a new television ($600), you can save a life? Here’s another: would it be worth foregoing a nice bottle of wine ($50) to cure someone’s blindness, thus allowing them to return to work and provide for themselves and their family? Could you come up with $700 to fix a new mother’s fistula, a debilitating condition that otherwise sentences her to incontinence and ostracism? Peter asks these questions because he wants to remind us that sums that are relatively trivial to us in the West can literally save or radically improve the life of someone in the developing world. He argues persuasively that we have the not just the opportunity but the obligation to help these people and doing so is in our own “enlightened self-interest." Peter is

Tony Hsieh was the former CEO of Zappos, which Amazon bought for $1.2 billion. With a net worth reported at over $700 million, Tony appeared to have everything anyone could want. However, Tony suffered from severe addiction that pulled him down into a spiral of substance abuse, bizarre behavior, and his eventual death. During the Covid lockdown, Tony bought over $50 million worth of houses in Park City, UT and actually paid his friends to come live near him and “be happy.” He died from injuries sustained in a house fire where he was locked in a shed. Angel Au-Yeung and David Jeans wrote the Forbes feature article, Tony Hsieh’s American Tragedy which details both Tony’s extraordinary accomplishments and his tragic demise. Dr. Drew Pinsky joins after Angel and David to discuss the correlation between wealth and addiction.  Angel Au-Yeung writes about billionaires at Forbes. David Jeans, also a Forbes staff reporter, covers the technology industry. His work appears regularly in the New York Times. Dr. Drew Pinsk

John Helliwell is Professor emeritus of Economics at University of British Columbia and editor of The World Happiness Report, a landmark survey of the state of global happiness that ranks 156 countries by how happy their citizens perceive themselves to be. The report has been published since 2012 when the United Nations General Assembly invited countries to measure their citizen’s happiness. And why not? We measure and report GNP, the GDP, the unemployment rate, average income, home sales, but not happiness. Aren’t all these things surrogates for what we should be evaluating, i.e. happiness?  On today’s show, John shares the themes he and his colleagues have identified over years of study but also the more recent effects of Covid pandemic and quarantine on our overall happiness.  John studied as a Rhodes Scholar at Oxford where he received his PhD. In 1967, John joined the economics faculty at University of British Columbia where he is now Professor Emeritus. In addition to many other distinctions, he was a v

Kay Madati was born to a single, Tanzanian mother who died when he was 12. Kay and his brother were then adopted by a very affluent caucasian couple who lived on the Upper East Side of Manhattan. His new family situation was an uncanny mirror to the plot of Diff’rent Strokes, one of the most popular American TV shows of the early 1980s. In a very short period of time, Kay went from a world where “black kids were never supposed to be anything but working class” to attending Riverdale Country School, an elite and nurturing private school in which teachers opened his eyes to his own massive potential. His experience, while rooted in tragedy, is a testimony to the transformative power of adoption and how parenting, education, and access are undeniable sources of privilege.  Kay eventually graduated from Georgetown University and went on to a career in media, working for some of the world’s most prestigious corporations, including BMW, CNN, Facebook, and BET Networks where he was Chief Digital Officer. Most recent

In this special Thanksgiving encore episode, I talk to A.J. Jacobs about his latest book, Thanks a Thousand: A Gratitude Journey, in which he expresses gratitude to a thousand people who are involved with getting him his morning coffee. A.J. Jacobs is an author, journalist, lecturer and human guinea pig. He has written four New York Times bestsellers that combine memoir, science, humor, and a dash of self-help. He is also editor at large at Esquire magazine, a commentator on NPR and a columnist for Mental Floss magazine.  Despite his references to the hygienic benefits of not shaking hands, this interview was recorded in pre-COVID 2019 at his office in New York City. Learn more about A.J. on his website. **Please rate and review Crazy Money here. Follow Crazy Money on Facebook here and join the Crazy Money Listeners Group here. Get your official Crazy Money t-shirts here.  Produced and edited by Mike Carano About Crazy Money: Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Mone

Rich Beem won the 2002 PGA Championship, one of professional golf’s four major tournaments. Despite having won twice on tour prior to the PGA, Rich's win at Hazeltine was as unlikely as the groovy dance moves he busted out after sinking his final putt of the tournament. Describing himself as “the luckiest guy in the world,” Rich loves golf and hanging out with people who give him energy. He played the game loose and wide open, but the rising expectations he felt after becoming a major champion became a distraction, and he never won again on tour. On today’s Crazy Money, Rich speaks candidly about grinding his way up the golf ladder, and how he found purpose and meaning in life as his PGA prospects began to dim.  Rich was born in Phoenix, AZ, grew up in El Paso, TX and played college golf at New Mexico State University. Today Rich plays on the PGA Champions Tour and works as a TV golf analyst on Sky Sports in the UK and Ireland. Follow Rich on Instagram and/or Twitter.  **Please rate and review Crazy Money her

Lisa Birnbach is the author of over 20 books, includingThe Official Preppy Handbook, a cultural phenomenon from the early 1980’s. The book sold more than a million copies and has been cited as an inspiration to the founder of J. Crew and is thought to have boosted the growth of LL Bean.  InT.O.P.H., Birnbach celebrated, skewered, and democratized the concept of preppiness, with writing the The New York Times described as “affectionate but acerbic.” Upon re-visiting the book, I found her reflections on money, fashion, status, and the social hierarchy as insightful and hilarious today as they were forty years ago. In this thoroughly enjoyable interview, we talk about the preppy aesthetic, Connecticut, and how the world has (and hasn’t) changed since she launched this juggernaut into being.  Celebrated for her keen eye and sharp wit, Lisa Birnbach is an award-winning journalist, cultural commentator, and bestselling author. She has written for The New York Times, The New Yorker, Parade, Rolling Stone, and New Yo

Dr. Brad Klontz is a psychologist and certified financial planner. He helps his clients (many of whom are ultra-high net worth individuals or even billionaires) understand how what they learned about money as kids affects their attitudes and dysfunctions today.  This week, both Paul and his editor/producer extraordinaire Mike Carano take Brad's Money Disorder Assessment and discuss their results in the hope he can cure them of their money ills. Brad’s work has been featured inThe Wall Street Journal, New York Times, Washington Post, Los Angeles Times, Time, Kiplinger’s, Money, NPR and many other media outlets and professional magazines and journals. He is the author of several books, includingMind Over Money.  Take his Money Disorder Assessment here. Check out his YouTube Channel.  Please take a moment to rate Crazy Money here. Find out more about Crazy Money and Paul Ollinger on his website and/or follow him on the socials:  • Twitter: http://Twitter.com/Paul_Ollinger • Instagram: https://www.instagram.com/p

Dylan Mohan Gray is the director of The King of Good Times, the pilot film of the new Netflix series, Bad Boy Billionaires: India, which has been the most viewed show in India for much of October. The film chronicles the rise and fall of Vijay Mallya, heir to a brewing fortune and founder of Kingfisher Airlines. Vijay was known for his excessive lifestyle, over-the-top personality, and lavish investments in sexy, high-profile ventures like cricket and Formula One racing teams. Despite his massive affluence, Vijay is accused of money laundering and fraud, which is said to have arisen from financial recklessness and over-reaching at his growing airline.  In this episode, Dylan and I discuss not only Vijay’s story, but how his excessive ambition, over-confidence, and lack of a sense of enough got him— and others who already have way more than they need — into big, big trouble.  An award-winning documentarian, Dylan also directed Fire in the Blood, which explored the high price of AIDS drugs in the developing wor

Janny Scott grew up on an 800-acre estate near Philadelphia. The descendant of railroad barons and financial magnates, Janny tracks the effects of her family’s multi-generational wealth in her book, The Beneficiary: Fortune, Misfortune, and the Story of My Father. In the book, she lays the details of both the opulence and the tragic complications of her family’s vast resources. 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 fourteen 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 Re

Kathy Wang grew up in Northern California and graduated from UC Berkeley and Harvard Business School. After working in the technology field for four years, she quit her job and wrote her first novel, Family Trust, which is the story of the Huangs, a first-generation Chinese-American family. With their father dying and his second wife waiting, the adult kids are wondering what will become of their father’s estate.  The book and this conversation explore differences in cultural attitudes toward careers, success, and money among Asian-American families. Said Kathy, “In Asian culture, you’ll always feel inadequate. I don’t think I’ve ever met an Asian person, no matter where they are in life, (who) feel that they’re doing a great job.”  Kathy lives in the Bay Area with her husband and two young children. She is working on her second book, which will be out soon. Find out more about Kathy here: http://www.bykathywang.com/ Read Paul’s latest essay on Medium. Please take a second to rate and review Crazy Money here.

Morgan Housel is the author of the new book, The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness. Success with investing and maintaining wealth is less about quantitative skill than it is about consistency and self-awareness. 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." Morgan’s book is an elegant summation of many of the things I want to discuss on this show. While it is partially about investing, it’s really about how knowing what you want from life will help you make better decisions about money. A partner at the Collaborative Fund and a former columnist at The Motley Fool and The Wall Street Journal, Morgan is a two-time winner of the Best in Business Award from the Society of American Business Editors and Writers, winner of the New York Times Sidney Award, and a two-time finalist for the Gerald Loeb Award for Distinguished Business

With eight Olympic medals (two of them gold), Apolo Ohno is America’s most decorated winter Olympian. He won his first major speed skating title (the US Championships) at the tender age of 14, after only six months of training. He continued on to a career that played a major role in establishing short-track speed-skating in the 2002, 2006, and 2010 Winter Games.  His New York Times best-selling memoir, Zero Regrets, tells the story of success, setbacks and what it takes to become one of the top athletes in the world. In this episode, Apolo and I go deep into the economic realities of becoming an Olympian. Due to the steep cost of coaching, training, equipment, and travel, many (perhaps most) athletes and their families go deep into debt in pursuit of a spot on the national team. And even for the few who make it, there is little preparation for post-Games remuneration and little preparation for a job “in the real world." In his post-skating career, Apolo has worked as a sports analyst for NBC, a global ambassa

As early Microsoft employees, Jennifer and her future-husband, David Risher, made millions of dollars from their stock options in the quickly growing company. When David joined an online book-seller called Amazon, those “millions” became “tens of millions,” and Jen found herself nervously navigating the world of affluence.  In her new book, We Need to Talk: A Memoir About Wealth, she explores the mind-bending experience of earning way more than she needed or ever imagined. While acknowledging their very good fortune, she nevertheless found herself dealing with guilt, awkward social situations, imposter syndrome, and the loss of identity that comes when you stop working.  There are over 18 million millionaires in the United States. Most of them did not grow up with a lot of money, so they had to learn how to handle it. Yet, talking about having money is considered extremely rude. A recent Money Matters study found that 68% of people would rather talk about their weight than money. And more people are more comf

Guy Raz is the host and co-creator of the smash NPR program, How I Built This and author of a new book by the same name. On the show, Guy provides entrepreneurs a platform to share their company’s origin stories and the trials and tribulations involved in getting their companies off the ground. In the new book, Guy goes deeper, reflecting on all he’s learned about what makes founders click.  In addition to How I Built This, Guy is the co-creator of TED Radio Hour and Wow in the World, the first NPR podcast for kids. His programs reach over 14 million people every month.  Before becoming one of the best-known podcasters in history, Guy was a war reporter and foreign correspondent. In 2000 NPR named Guy the bureau chief in Berlin where he covered Eastern Europe and the Balkans. He was just 25 years old. During his six years abroad, he reported from more than 40 countries including the wars in Iraq, Afghanistan, and Macedonia. For his reporting from Iraq, Guy won both the Edward R. Murrow Award and the Daniel