Reasonably Happy with Paul Ollinger

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...

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 me...

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...

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 ad...

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...

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...

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.  ...

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 ch...

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 ...

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. V...

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...

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 conversat...

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...

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 was...

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...

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...

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...

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...

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...

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 s...

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 ot...

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 ha...

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 work...

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, Rolli...

Lori Gottlieb is a psychotherapist and author of the best-selling (and excellent) book, Maybe You Should Talk to Someone, which is being developed into a series for ABC by Eva Longoria. Lori pens the weekly "Dear Therapist" column for The Atlantic, and has written for The New York Times, The Washington Post, The Los Angeles Times, Time, People, Slate, Salon, and many other top periodicals.  Lori a...