

Reasonably Happy with Paul Ollinger
Paul Ollinger
Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.
Episodes
Mentioned books

May 25, 2021 • 53min
Wealth and Existential Despair with Melissa Bernstein - Ep 109
Melissa Bernstein has great wealth, a wonderful husband, and six healthy children. She has also endured a lifetime of “existential anxiety and depression,” suicidal thoughts, and a feeling that she does not belong on earth. The Co-founder of Melissa & Doug’s toys describes her brain as a “prison of despair” but that same brain also provides her the “boundless expanse of imagination” that has helped her design over 5,000 toys in the 32 years since she and her husband co-founded the massively successful company. Despite her success, all the money in the world can’t change the way her brain works, nor would she trade it for anyone else’s brain. For decades, Melissa kept her condition to herself and tried to fit in by pursuing conventional indicators of success: good grades, the right college, an investment banking career. Earlier this year, Melissa and Doug launched LifeLines, an app, book and online resource center for anyone dealing with severe mental health issues of their own or in their family. Check it out here: https://www.lifelines.com/ === SUPPORT THE SHOW: ✍️ RATE / REVIEW Crazy Money: >> http://ratethispodcast.com/crazyMoney CONNECT WITH PAUL: 📸 Instagram: >> https://www.instagram.com/crazymoneypodcast/ 🌍 Facebook (Crazy Money Listeners Group): >> https://www.facebook.com/groups/446049973036596 About Crazy Money: Unlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, 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 management, culture, society, status, ambition, accomplishment. Perfectionism

May 18, 2021 • 53min
Moby on Fame, Fortune, Addiction, Animals - Ep 108
Moby’s first job as a DJ was spinning records at a dive bar next to a methadone clinic. A few years later, he was rich and famous, but "never felt more depressed.” Having grown up as "poor white trash” in the wealthy town of Darien, CT, Moby's financial status made him feel like a “third-class citizen.” Decades after selling over 20 million albums, winning all kinds of awards, and experiencing "baffling success," he still feels disenfranchised. The massive, unpredictable success of his 1999 album, Play set an incredibly high bar against which the press and he himself measured his subsequent work. His consumption of alcohol, cocaine, and related chemical goodies drove him to a dark place from which he finally rebounded in 2008. He has been sober ever since. Moby addresses all these issues in the upcoming documentary, MobyDoc. In this episode of Crazy Money, we also discuss his relationship to finances, debt, why he’s never had a mortgage, and can’t even bring himself to borrow 50 cents to buy a pack of gum. He also shares the origins of his full-time commitment to animal rights and veganism. See the film trailer for Moby Doc here and learn more about his orchestral greatest hits record, Reprisehere. Both come out on May 28. ✍️ RATE / REVIEW Crazy Money: >> http://ratethispodcast.com/crazyMoney CONNECT WITH PAUL: 📸 Instagram: >> https://www.instagram.com/crazymoneypodcast/ 🌍 Facebook (Crazy Money Listeners Group): >> https://www.facebook.com/groups/446049973036596 Topics that come up in this episode include: depression, addiction, alcoholism, cocaine, David Bowie, animal cruelty, veganism, vegetarianism About Crazy Money: Unlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, 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 management, culture, society, status, ambition, accomplishment.

May 11, 2021 • 53min
Life After Paralysis with Maura McVann Coley - Ep 107
In 1988, Maura McVann Coley sustained a traumatic spinal cord injury that deprived her of the ability to walk. Just 17 at the time of the accident, the then high school athlete had to adjust her expectations for senior year, college, and life beyond. On today’s episode, Maura shares with great candor how she adapted logistically and emotionally to her new and very different circumstances. She offers insight into how she navigated college at the University of Illinois, traveled through Europe, and figured out young adult life. Things get very real when Maura tells me why she was scared to date. Today, Maura and her husband, Kevin Coley raise two children and a dog in Daphne, AL where they own and operate a small business called We Rock the Spectrum Daphne. Maura also runs a pediatric speech therapy practice called Speech Time Therapy Services where kids of all abilities learn and develop critical communication skills in a fun and playful environment. She loves traveling to new places with her family, helping others, and promoting disability awareness and acceptance through her work and life example. She has used a wheelchair for almost 33 years. Learn more about #spinalcordinjury and the place Maura started her rehab, Shepherd Spinal Center. SUPPORT THE SHOW: ✍️ RATE / REVIEW Crazy Money: >> http://ratethispodcast.com/crazyMoney CONNECT WITH PAUL: 📸 Instagram: >> https://www.instagram.com/crazymoneypodcast/ 🌍 Facebook (Crazy Money Listeners Group): >> https://www.facebook.com/groups/446049973036596 About Crazy Money: Unlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, 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 management, culture, society, status, ambition, accomplishment.

May 4, 2021 • 44min
Rebounding from Mid-life Melancholy with Jonathan Rauch - ENCORE EPISODE
(Originally posted Jan, 2020...but so worth another listen) In The Happiness Curve: Why Life Gets Better After 50, Jonathan Rauch explores the decline in happiness that most people experience in middle age and what there is to do about it. Even after achieving all we had ever dreamed of and more, many of us experience a disappointment or melancholy, and question if “this” is all there is to life. The first thing to understand that this is normal. Your doubts are okay and part of the aging process of the mind. The second thing to embrace is that you will be okay! Listen now to find out how and why. Jonathan Rauch is a Senior Fellow at the Brookings Institution and contributing editor of The Atlantic. His writing spans the full spectrum of society, including politics, marijuana legalization, health care, gay marriage, adultery, agriculture, economics, height discrimination, and animal rights. This work has earned him many honors, including the National Magazine Award and the National Lesbian and Gay Journalists Association prize for excellence in opinion writing. You have probably read some of it in The Economist, Reason, Harper’s, Fortune, The New York Times, The Wall Street Journal, The Washington Post, Slate, The Advocate, or many other leading publications. He does not like shrimp. See Thomas Cole's "The Voyage of Life" here. Learn more about Jonathan: https://www.jonathanrauch.com/ SUPPORT THE SHOW: ✍️ RATE / REVIEW Crazy Money: >> http://ratethispodcast.com/crazyMoney CONNECT WITH PAUL: 📸 Instagram: >> https://www.instagram.com/crazymoneypodcast/ 🌍 Facebook (Crazy Money Listeners Group): >> https://www.facebook.com/groups/446049973036596 ---------------------- About Crazy Money: Unlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, 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 management, culture, society, status, ambition, accomplishment.

Apr 27, 2021 • 52min
How business education builds character with Matt Slaughter - Ep 106
Matthew J. Slaughter is the Dean of the Tuck School of Business at Dartmouth where Paul (the host of this show) earned his MBA. In today’s conversation, Matt and Paul discuss the role of business education in creating not just savvy business leaders but curious, ethical human beings. Matt shares insights into the challenges the pandemic inflicted on universities, how Covid-19 caused the worst day of his career, and how to behave in the Oval Office. An expert on globalization, Matt is also the Earl C. Daum 1924 Professor of International Business. From 2005-07, he served on President George W. Bush’s Council of Economic Advisers.He is a member of the American Academy of Arts and Sciences, a life member of the Council on Foreign Relations, a Research Associate at the National Bureau of Economic Research; a member of the academic advisory board of the International Tax Policy Forum; and an academic advisor to the McKinsey Global Institute. Matt received his bachelor’s degree summa cum laude and Phi Beta Kappa from the University of Notre Dame in 1990, and his doctorate from the Massachusetts Institute of Technology in 1994. You can read more about Matt here. SUPPORT THE SHOW: RATE / REVIEW Crazy Money: http://ratethispodcast.com/crazyMoney BUY A SIDECAR FOR THE FASHIONABLE MOM IN YOUR LIFE: http://sidecarlove.com CONNECT WITH PAUL: Instagram: https://www.instagram.com/crazymoneypodcast/ Facebook (Crazy Money Listeners Group): https://www.facebook.com/groups/446049973036596

Apr 20, 2021 • 60min
The Science of Well-being with Dr. Laurie Santos - ENCORE EPISODE
(Originally posted Sept, 2019...but so worth another listen) Our brains are not good at predicting what will actually make us happy. You think you want more money, more fame, and to be alone, but what will actually make you happy are more social connections and more gratitude. Dr. Santos’ course Psychology and the Good Life—the most popular class in Yale’s history—teaches students to live happier, more fulfilling lives, which is good because student rates of anxiety, depression, and suicidal thoughts are at an all-time high. Laurie Santos, PhD is a cognitive scientist, Professor of Psychology and Director of Yale’s Comparative Cognition Laboratory. She is the host of The Happiness Lab podcast. Laurie earned her AB, AM and PhD’s from Harvard University. **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here.Email Paul guest suggestions, Bitcoin, and gift certificates at: Paul@CrazyMoneyPodcast.comAbout Crazy Money: Unlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, 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 management, culture, society, status.

Apr 13, 2021 • 56min
Our possessions, ourselves with Michael Heller & James Salzman - Ep 105
What does it mean to “own” something? Do you “own”your body? Do you own the dirt in your backyard? If someone flies a drone over your deck, do you have the right to blast it out of the sky? (Seems fair to me, but the law says otherwise.) In their new book,Mine!, law professors Michael Heller and James Salzman explore the the concept of ownership and property in ways you have almost certainly not considered. I love books that make me re-think a concept that I take for granted. InMine!, Heller and Salzman do just that. Most of us assume we know what it means to own something or who has the right to certain things or spaces. But the law isn’t always self-evident, is wildly inconsistent, and varies from country-to-country and state-to-state. Manyof the examples they cite will piss you off! For example, who owns the space just behind the airplane seat in front of you? Does that sweaty dude in that chair have the right to recline? Or does that space belong to you and your sensitive knees? Also, why can you copyright a song but not a comedy routine? (Huh, HUH??!!!??!!) I thoroughly enjoyed my conversation on this non-obvious topic with these two brilliant gentlemen. Michael Heller is the Lawrence A. Wien Professor of Real Estate Law at Columbia Law School. He has taught at the NYU, UCLA, University of Michigan and Yale Law Schools. He is an honors graduate of Harvard College and Stanford Law School. James Salzman is the Donald Bren Distinguished Professor of Environmental Law with joint appointments at UCLA School of Law and the UC Santa Barbara School of Environment. Among many other accolades, Jim is a fellow of the Royal Geographical Society, a McMaster Fellow and a Fulbright Senior Scholar. He is a graduate of Yale and holds graduate degrees in both Law and Engineering from Harvard University. Get tickets to Paul’s 4/22 show at MadLife studios HERE. Learn more aboutMine!here. **Please rate and review Crazy Money here.**Follow Crazy Money on Instagramand join the Crazy Money Listeners Grouphere. Produced and edited by Mike CaranoAbout Crazy Money:If you don’t like to think, you’re going to hate 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 be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, rat race, society, 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.Are you really still reading?

Apr 6, 2021 • 58min
Wall Street, the movie: a panel discussion - Ep 104
This week we tried out a new format—a panel discussion about the 1987 classic Oliver Stone film, Wall Street. It starred Charlie Sheen, Michael Douglas, Darryl Hannah and a whole bunch of other amazing actors. The movie, which was a morality tale about financial excess, both celebrated and condemned the era's obsession with money and over-the-top luxury (clearly that’s over!). In addition to cocaine, caviar, and steak tartare, it asked us to consider:
How much is enough?
How do you define success?
Is greed, for lack of a better word, good?
My friend A.M. Bhatt and I moderated this discussion on the Clubhouse app including previous Crazy Moneyguests:
Turney Duff, author of The Buy Side
Lisa Birnbach, author of The Official Preppy Handbook
Brad Klontz, financial psychologist and author of Money Mammoth and other books
Get tickets to Paul’s show in Woodstock on April 22 here. Rate and review Crazy Money here.

Mar 30, 2021 • 51min
Wall Street Trader Turns Big Time Writer with Jared Dillian - Ep 103
A working class kid from the poor part of Connecticut, Jared Dillian somehow managed in 2001 to land a job as a trader at Lehman Brothers, the then-prestigious investment bank. Wearing cheap suits from the Mens Wearhouse, he found himself out-of-place among the Armani-clad Ivy League set on Wall Street. But he loved trading and made a lot of money in the process. In this candid conversation, Jared shares frank insights into the incredible stress of trading and the mental health that became apparent as his career progressed. Those persistent mood swings turned out to be a symptom of undiagnosed Bipolar disorder, which resulted in him spending three weeks in the psychiatric ward, a place he described as “a very healing environment." After Lehman went bankrupt, Jared pivoted to a successful writing career. Today, he is the Editor of The Daily Dirt Nap, an investment newsletter providing daily market commentary and insight to traders and very serious investors. He has also written two books: Street Freak: A Memoir of Money and Madness, a gripping read which chronicles his time as a trader with Lehman Brothers from 2001-2008, and the novel, All The Evil of this World, which Paul is looking forward to reading. Jared graduated from the US Coast Guard Academy and earned his MBA From University of San Francisco. When he’s not writing or taking care of his 5 cats, he is making music under the name, DJ Stochastic. He lives in Pawleys Island, South Carolina.
Learn more about The Daily Dirtnap
Check out Jared’s music here.
Jared’s radio show here
Please take a second to rate and review Crazy Money here. (Click on “your" app)Follow Paul on Instagram.Topics covered in this episode include investments, trading, Wall Street, Lehman Brothers, writing, mental health, bipolar disorder, OCD, Bloomberg, Matt Levine

Mar 23, 2021 • 50min
Money and the Maasai people with Josphat Mako - Ep 102
My guest today paid a dowry of eight cows for his first wife and six cows and three sheep for his second wife. Josphat Mako, or just “Mako," grew up in Kenya’s Maasai Mara, a massive plain just north of the Serengeti. He taught himself English, learned how to drive, and has since become become a well-known safari guide for the legendary Cottars camps. In today’s episode, we talk about his childhood, daily life in the Maasai Village, who goes to school in their culture (it will surprise you!), and what it was like when he attended a football game at the University of Alabama in Tuscaloosa. Special thanks to Ann Short travel here in Atlanta, Bush & Beyond in Nairobi and the good people at Cottars Conservation camp in the Mara. See photos from our trip are in the Crazy Money Listeners group in Facebook.
See the Sidecar hat carrier here.
Get tickets to see Paul at MadLife Studios here.
Rate and review Crazy Money here.
Topics covered in this episode include: #alabamafootball #maasai #maasaimara #travel #safari #africaUnlike traditional personal finance 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 credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be 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.


