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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

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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57:41

The Need to Belong with Geoffrey L. Cohen

Reasonably Happy with Paul Ollinger ·

2022/11/15

We don't think about it all the time, but BELONGINGNESS is the third most fundamental desire on Maslow’s Hierarchy of Needs. Just above safety and physiological requirements, is our need to feel safe as part of a tribe. My guest this week is Geoffrey L. Cohen, the author of Belonging: the Science of Creating Connection and Bridging Divides. Geoff is a professor of Psychology and Organizational studies at Stanford University in Palo Alto, California. In this conversation, he and I talk about what it

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48:12

The Hedge Fund Legend Hugh Hendry

Reasonably Happy with Paul Ollinger ·

2022/11/09

Former hedge fund manager Hugh Hendry grew up working class in Glasgow, Scotland. His anxiety, detachment from money, and passionate observations of life led him to hypotheses and market positions others couldn’t see. In 2008, when the rest of the world was melting down, Hugh’s Eclectica Asset Management returned over 30%. As great as the money was, he says what drives him is a profound need to be loved. Today, Hugh develops property in St. Barths where he lives full time. In this conversation,

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45:19

Money and Opioids with Barry Meier

Reasonably Happy with Paul Ollinger ·

2022/11/03

Barry Meier is a former investigative reporter at The New York Times and the author of the book, Pain Killer: An Empire of Deceit and the Origin of America's Opioid Epidemic, which explores how the Sackler family's greed catalyzed a plague of addiction and death that has destroyed families and whole communities across the country. Between 1999 and 2000, 564,000 Americans died from an opioid overdose. In 2020, the most recent year for which statistics are available, there were over 68,000 opioid

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53:23

Why Status Matters with Will Storr

Reasonably Happy with Paul Ollinger ·

2022/10/25

Where do you sit on the social hierarchy? You might not think about it daily, but if I asked you to compare your status to that of one of your friends, you'd probably know the answer: above some, below others, and probably on about the same level as most. Perhaps you'd follow up with questions like “Do you mean who has more money? Or who has more recognition in the community or who's more attractive or physically fit?” This request for clarification demonstrates the nature of status, and how we go

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57:55

Money in College Sports, Part 2 (with AJ Vaynerchuk...

Reasonably Happy with Paul Ollinger ·

2022/10/18

This episode is Part Two of our Money in College Sports: NIL series. Until last year, college athletes were prohibited from collecting any compensation. But today, thanks to Name, Image, and Likeness (NIL) deals, the stakes are high and getting higher. To make sense of this issue, I speak with A J Vaynerchuck from Vayner Sports and Laine Higgins from the Wall Street Journal. A J Vaynerchuk is the co-founder of sports management agency, Vayner Sports where he has been a part of several NIL deals for

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42:02

Emotions and Money Stress with Ken Honda

Reasonably Happy with Paul Ollinger ·

2022/10/11

The news from the economic world is pretty bad right now. Inflation up and the stock market’s down, which means we're all experiencing some degree of financial stress. Here to help us put it all in perspective is Ken Honda. Known as Japan’s Zen millionaire, Ken’s book Happy Money has sold over 8 million copies worldwide. In this, his second visit to Crazy Money, we talk about: What economic fear, uncertainty and doubt can do to our health and our relationships; How we can maintain peace of mind when

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48:50

Robinhood, Wall Street Bets, and the GameStop Stock...

Reasonably Happy with Paul Ollinger ·

2022/09/27

Spencer Jakab is the editor of The Wall Street Journal's Heard on the Street column and the author of a fascinating new book called The Revolution That Wasn't: Gamestop, Reddit, and the Fleecing of the Retail Investor. In January of 2021, a large group of small investors from the WallStreetBets subreddit rallied around the stock of video game retailer GameStop, which they believe had been unfairly attacked by short-selling hedge fund Melvin Capital. The subsequent and totally unexpected rally in the

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46:30

Money in College Sports, Part 1 with Darren Rovell...

Reasonably Happy with Paul Ollinger ·

2022/09/20

Up until last year, no college athlete could legally, officially accept compensation for playing a sport at his or her college. That changed last year with a Supreme Court ruling that now allows college athletes to be compensated for the use of their Name, Image and Likeness (NIL). On today's show, I talk to Darren Rovell, a sports reporter who spent 18 years on the air with CNBC and ESPN and now a senior executive producer at the Action Network. I also talk to John Staton, who is the Director of

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50:08

Money and Pro Golf: How LIV Golf’s Billions Threaten...

Reasonably Happy with Paul Ollinger ·

2022/09/13

Saudi-backed LIV Golf is throwing hundreds of millions of dollars at top pro golfers in an attempt to lure them away from the PGA Tour. The Tour is responding with massively-increased prize money and more player-friendly tournaments. Here to discuss these unprecedented changes and their unsavory ramifications is Rich Beem, winner of the 2002 PGA Championship and analyst for SKY Sports Golf. Rich shares his candid and often funny insights into where this crazy mess is headed, which league is in a

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50:50

Porn, Money, and Women in Hollywood with Maitland Ward

Reasonably Happy with Paul Ollinger ·

2022/09/06

Maitland Ward is an adult film star and author of a new book called Rated X: How Porn Liberated Me from Hollywood. Best known for her role as Rachel Maguire on Boy Meets World, Maitland enjoyed a successful career as a Hollywood actress before making the transition into the adult film industry. Her videos and photos on OnlyFans now earn her over $1 million per year. And that's in addition to the money she makes making adult films. Rated X is her first book, and I gotta tell you, I found it to be

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67:45

Drug Cartels, Money Laundering, and HSBC with Chris...

Reasonably Happy with Paul Ollinger ·

2022/08/30

I've got a great conversation to share with you today about international banking, massive drug cartels and billions and laundered money. My first guest is Chris Blackhurst. He's the author of a book called Too Big to Jail: Inside HSBC, the Mexican drug cartels and the biggest banking scandal of the century. And if you think about that, we've already had a couple of big banking scandals, so this is a big one. The book tells the story of how HSBC ignored money laundering laws and processed BILLIONS

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71:12

The Prison Break of a Global CEO - The story of...

Reasonably Happy with Paul Ollinger ·

2022/08/23

Carlos Ghosn is the former CEO of both Renault and Nissan. Japanese authorities arrested him for (allegedly) paying himself tens-of-millions in unreported income (and some other shady stuff). Carlos escaped the brutal Japanese judicial system by having himself smuggled out of the country in a box! My guests Nick Kostov and Sean McLain are Wall Street Journal reporters whose new book, BOUNDLESS: The Rise, Fall, and Escape of Carlos Ghosn chronicles the former globe-trotting executive’s meteoric rise

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52:42

Student Loan Debt with Oren Cass

Reasonably Happy with Paul Ollinger ·

2022/08/16

Why in the world is student debt treated differently than all other kinds of debt? Why does the cost of college keep sky-rocketing? Why do colleges and universities have so little skin in the game when it comes to the debt students incur to attend these institutions? On this week’s Crazy Money, Oren Cass helps answer these important questions about higher education in the U.S. The author of ‘The Once and Future Worker: a Vision for the Renewal of Work in America,’ Oren’s recent article ‘The Banality

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310 results

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