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PODCAST

Reasonably Happy with 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.

business philosophy

All Episodes

74:46

Searching for Meaning at Work with Bruce Feiler

Reasonably Happy with Paul Ollinger ·

2023/05/31

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

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52:34

Family Fortune and Misfortune with Janny Scott (Encore)

Reasonably Happy with Paul Ollinger ·

2023/05/23

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

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74:14

Kevn Kinney is Done Auditioning

Reasonably Happy with Paul Ollinger ·

2023/05/16

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

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47:40

Starting from the Bottom with Justin Richmond

Reasonably Happy with Paul Ollinger ·

2023/05/09

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

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57:26

Is Private School Worth it?

Reasonably Happy with Paul Ollinger ·

2023/05/02

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

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50:36

Using Your 4,000 Weeks with Oliver Burkeman (Encore)

Reasonably Happy with Paul Ollinger ·

2023/04/25

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

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52:22

Cooking with Money w/ Frankie Celenza

Reasonably Happy with Paul Ollinger ·

2023/04/19

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

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36:04

Wealthy Woman Flies Southwest with Leah Rudick

Reasonably Happy with Paul Ollinger ·

2023/04/11

Leah Rudick is an actor, writer, and comedian whose Wealthy Woman character videos have earned her almost one million followers on Instagram and TikTok. Thanks to her breakout social media success, Leah is now selling out comedy shows all over the country. In these videos, a clueless woman of wealth shares her point-of-view on everyday experiences like going to Cracker Barrel, flying Southwest Airlines, renting a car, or taking the bus. I (Paul Ollinger, hoster of show / writer of episode notes)

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53:45

Morgan Housel on The Psychology of Money (Encore)

Reasonably Happy with Paul Ollinger ·

2023/04/05

Morgan Housel is the author of the book, The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness. 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." While the book is partially about investing, it’s really about how knowing what you want from life will help you make better decisions about money. I really enjoy Morgan’s writing and found

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40:38

Cars, Sex, and Money with Robert Searle

Reasonably Happy with Paul Ollinger ·

2023/03/29

Do women find men in expensive cars more attractive than men in less expensive cars? Some people believe that the answer to this question is so patently self-evident as to not require any thought. But my guest today conducted actual scientific research into this age-old stereotype. Rob Searle is a Welsh psychologist who co-authored a paper evaluating the status-enhancing effects of luxury vehicles on the attractiveness of both men and women to heterosexual members of the opposite sex. He asked

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28:08

Why it’s Called “F-You Money” and other Thoughts on...

Reasonably Happy with Paul Ollinger ·

2023/03/21

This week, Paul reads some of the recent essays from his Substack. In "Why Talking About Money and Happiness Matters” he reflects on the reasons Bono, Jonah Hill, and Brian Cox have all, in the past few months, engaged in public discussion on the nature of success and what it can and can’t do for us. In "Lessons from a Freshman Pimple,” Paul recalls the devastating experience of an early high school face blemish and why seeking others’ approval can lead us to bad decisions. In "The Real Reason They

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56:40

Cancer, Careers, Finances, and Family with Julie...

Reasonably Happy with Paul Ollinger ·

2023/03/15

Julie Saxon is the mother of two and a senior media executive. In 2013, her life was upended when her husband, Joel, was diagnosed with stage IV colorectal cancer. Thus began journey during which she had to keep the train on the tracks at work and at home while helping Joel fight for his life. But after 6 valiant years, 87 rounds of chemo, ten rounds of radiation, seven surgeries, and two clinical trials, he lost that battle. Joel lived longer than 99% of patients with his diagnosis, and—as I was

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42:17

Mass Hole Donuts co-founder Peter Gladstone

Reasonably Happy with Paul Ollinger ·

2023/03/07

This episode is about working for fun, love, and legacy. Peter Gladstone is the Co-founder of Mass Hole Donuts, bakers of gourmet donut holes that celebrate the people, traditions, and spirit of Boston and Massachusetts. After 20 years in consumer marketing with companies like Gillette, P&G, and the Boston Beer Company (aka, Sam Adams), Peter retired and is now building Mass Holes because, he says, it’s fun, and he wants to contribute to the culture of his hometown. When he’s not establishing his

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42:24

Rich B*tch Nicole Lapin: More than Meets the Eye

Reasonably Happy with Paul Ollinger ·

2023/02/28

Nicole Lapin is the New York Times best-selling author of Rich Bitch, Boss Bitch, Miss Independent, and Becoming Super Woman. A summa cum laude graduate of Northwestern University’s journalism school, she became one of the youngest anchors in CNN’s history at age 21. In this episode, we discuss her parents’ rancorous divorce, her dad’s death by overdose, and the resulting financial turmoil that set her on a mission to help women have more financial literacy and empowerment in their lives and

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54:22

A Hollywood Dream Career with Larry Thompson

Reasonably Happy with Paul Ollinger ·

2023/02/21

Larry Thompson is an entertainment manger in Beverly Hills, CA. In his 50+ years in Hollywood, Larry has guided the careers of over 200 stars, including Drew Barrymore, William Shatner, Cicely Tyson, Joan Rivers, Sonny & Cher, David Hasselhoff, Barry White, and Cindy Crawford. Larry grew up in Clarksdale, MS, graduated from Ole Miss law school then drove across country to chase his dream in Hollywood. As a young lawyer at Capitol Records, he helped negotiate the break-up of the Beatles then

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58:24

New Fame, New Money with Katherine Blanford

Reasonably Happy with Paul Ollinger ·

2023/02/14

A year ago, Katherine Blanford was working as a nanny by day and doing comedy at night. Last summer, she made her network television debut on The Tonight Show with Jimmy Fallon and is now headlining around the country and opening for David Spade. She and I discuss the experience of having "heat" and cash in her pocket for the first time. We talk about artistic envy, the work ethic needed to succeed in comedy, what she learned about wealth and careers while working as a nanny, and of course, how much

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22:04

Crazy Money's direction in 2023

Reasonably Happy with Paul Ollinger ·

2023/01/02

Hey everybody. Happy 2023! This is a short, lightly edited greeting from Paul /me about where the podcast has been in 2022 and where we're going to take it in the year to come. I am grateful for your continued support and interest. I wish you and your family a safe, prosperous, and fulfilled year. Carpe Diem! ✍️ Subscribe to Paul's Substack newsletter here.✍️ 🔥Subscribe to us on YouTube here. 🔥 📧 E-mail Paul at Paul@CrazyMoneyPodcast.com 📧 Crazy Money is produced and edited by Mike Carano

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48:08

How Your Mindset Can Change Your World with David Robson

Reasonably Happy with Paul Ollinger ·

2022/12/20

The philosophical martial artist and actor, Bruce Lee is supposed to have said, “So you think, so shall you become.” On this week’s episode, we explore the power of positive expectations with David Robson, an award-winning science writer and author of the new book The Expectation Effect: How Your Mindset Can Change Your World. As you’ll hear, David makes a strong argument supporting Bruce Lee’s message: that positive expectations can meaningfully improve our lives. To be clear, this is not about the

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58:36

Growing Up Rich with Kristin Keffeler

Reasonably Happy with Paul Ollinger ·

2022/12/06

Kristin Keffeler is the author of a new book called The Myth of the Silver Spoon: navigating family wealth and creating an impactful life. Kristin is also the founder of Illumination360 where she works with ultra high net worth families, including many worth billions of dollars. Her specialty is helping the rising generations create their own identities having grown up with extreme family wealth. In this conversation, Kristin and I talked about how her own family's affluence led her into this field;

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45:42

Why Boys and Men are Struggling with Richard Reeves

Reasonably Happy with Paul Ollinger ·

2022/11/22

Richard Reeves is a senior fellow at the Brookings Institution and the author of a new book called Of Boys and Men: Why the Modern Male Is Struggling, Why It Matters, and What to Do about It. You might ask, “Why is this topic relevant to Crazy Money, a podcast about money and happiness, work and meaning?” Because the connection between education, gainful employment and life satisfaction is massive. And on these metrics, the modern male is not doing well. Consider some of these data points: Boys are

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303 results

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