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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

62:32

Restoring Politcal Sanity with Charlie Wheelan (Encore)

Reasonably Happy with Paul Ollinger ·

2024/06/04

Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no nudity in either), and The Centrist Manifesto, all of which we discuss in this episode. The Chicago Sun-Times describes Charlie as someone who “combines a razor-sharp mind with a boatload of charm and impressive expertise in economics and foreign policy,” which might be why his students regularly pick him as one of Dartmouth's 10 best

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46:10

Mike Posner on Life Beyond Fame and Fortune

Reasonably Happy with Paul Ollinger ·

2024/05/28

Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays and his song 'I Took a Pill in Ibiza' reached the top five on the Billboard Hot 100. Mike "had it all" at a young age and captured his lifestyle in the lyrics of his biggest hit: “A real big baller (who) made a million dollars and...spent it on girls and shoes.” But Mike wanted more—he wanted to live a life of meaning and purpose - to become the person

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50:56

Andrew Yang on Our Broken Political System (Encore)

Reasonably Happy with Paul Ollinger ·

2024/05/21

Andrew Yang is a former Presidential and NYC mayoral candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for structural reform to safeguard our democracy. He lays all this out in his new book, ‘Forward,' which we discussed today. We also discuss Andrew's life as a teenager, his obsession with post-punk bands like The Smiths, Depeche Mode, and Nine Inch Nails, why he didn’t do drugs as a teenager, and how his parents felt when he got his ear

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64:32

The Third Path with Jordan Harbinger

Reasonably Happy with Paul Ollinger ·

2024/05/14

Jordan Harbinger is one of the most popular podcasters in North America, but it all started by accident. As a young University of Michigan grad, Jordan decided to go to law school because it was something to do after college and eventually ended up at a Wall Street firm. A multi-linguist, Jordan traveled and met new people all over the world. He eventually started teaching networking to other young adults. The tapes—compact discs, actually—of his presentations became so popular that he decided to

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51:32

Living The Constitution with AJ Jacobs

Reasonably Happy with Paul Ollinger ·

2024/05/07

Good morrow, chum! My guest this week is A.J. Jacobs, author of the new / amazing book 'The Year of Living Constitutionally: One Man’s Humble Quest to Follow the Constitution’s Original Meaning’, in which A.J. chronicles his year of living as an 18th Century citizen, including writing letters with quill and ink, carrying a musket around the Upper West Side of Manhattan while wearing colonial garb, and celebrating election days with cake and rum! It’s the latest of his year-long experiments in living

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61:48

Being Human at Work with Kim Scott, author of...

Reasonably Happy with Paul Ollinger ·

2024/04/30

‘Radical Candor’ author Kim Scott once had to inform a colleague that they smelled bad….like, really bad. She was able to do so becuase she had created on her team a culture or radical candor. No, this doesn’t mean you can just walk up to colleagues and say, “you stink!” or “nice shirt, bozo!” On the contrary, radical candor is a culture where authentic personal caring co-exists with direct challenges. Lacking this combination, workplace communication falls into one of three meaningfully-less

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56:22

Power Couple: Debbi “Mrs.” Fields and Wade Shealy

Reasonably Happy with Paul Ollinger ·

2024/04/24

Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his start selling Bibles door-to-door then went on to develop and sell > $3 billion in resort real estate over the next few decades, including Hampton Island, GA whose residents include Ben Affleck / Jennifer Lopez and Robert / Lydia Monday. He is now CEO of Third Home, a vacation home sharing platform that empowers its members to see the world. In this

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69:16

Death, Dying, and Israel with Rabbi Steve Leder

Reasonably Happy with Paul Ollinger ·

2024/04/16

Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times best-selling author of sevaral books, including 'For You When I Am Gone’ and 'The Beauty of What Remains,’ both of which pertain to death and dying. I had planned on speaking with Steve primarily about death for an hour, but our conversation covered everything from regret to forgiveness to the life of a rabbi. He shares lessons about fund-raising, his

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41:48

The Wealth Money Can’t Buy with Robin Sharma

Reasonably Happy with Paul Ollinger ·

2024/04/09

Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, The Monk Who Sold His Ferrari, The Everyday Hero Manifesto, and Who Will Cry When You Die?, Robin has a new book out called The Wealth Money Can’t Buy in which he examines the ways we can all develop happiness with and beyond financial wealth. In this conversation, Robin shares with me insights from the book, specifically: The danger of focusing

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65:56

America’s Government Teacher, Sharon McMahon

Reasonably Happy with Paul Ollinger ·

2024/04/04

Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience through “the fascinating world of democracy, politics, and history.” In the process, she is proving that Americans—and other good people around the globe—are hungry for unbiased political context and analysis. "With a heart for education and a mission to clear up political confusion,” Sharon has become known as America’s Government Teacher

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64:14

Poor Kid Makes Millions Trading, Fights Inequality...

Reasonably Happy with Paul Ollinger ·

2024/03/29

Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his gift for mathematics landed him a spot at London School of Economics (alma mater of Mick Jagger, Margaret Thatcher, and George Soros) where he attended with the sons and daughters of the global elite. His skill at a card game won him a job on Citibank’s trading desk and he went on to earn multi-million dollar—er, pound sterling—bonuses in his

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63:36

The Narcissist Next-door with Dr. Ramani Durvasula

Reasonably Happy with Paul Ollinger ·

2024/03/20

Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In this insight-rich conversation, Dr. Ramani explains the traits and behaviors of narcissistic individuals, how they hijack our well-being, and the motivations behind their attention-seeking behavior. She also relieves Paul of the sneaking suspicion that he might be a narcissist. Other topics include:Gender and narcissism (ladies is

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51:54

TED's Chris Anderson on Infectious Generosity

Reasonably Happy with Paul Ollinger ·

2024/03/14

Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues that YOU and I can improve the world by embracing our natural inclination toward generosity. He speaks not just of financial generosity, though that’s certainly a huge part of it, but also of creative generosity and generosity of spirit. In this conversation, Chris and I discuss:The formula to determine if you are a net giver or a net taker in

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106:09

Mike and Paul’s Road Trip

Reasonably Happy with Paul Ollinger ·

2024/03/05

This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip between San Francisco where Paul had just performed at Cobb’s Comedy Club and San Luis Obispo where he was heading to perform in the SLO Fest Comedy Festival. Among other things, Paul and Mike discuss:Memories of commuting from SF to Yahoo! in Sunnyvale Why it’s hard to admit what we want in life The history of Crazy Money The possible new names for

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49:06

On Fire for Life with John O’Leary

Reasonably Happy with Paul Ollinger ·

2024/02/28

When John O’Leary was 9 years old, he played with fire and got burned. Like really, really burned, over 99% of his body. Doctors gave him less than 1% chance to live and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, survive he did. His journey back took years, required dozens of surgeries, and cost him all of his fingers. Today, John is a world-renowned inspirational speaker who has addressed audiences around the

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39:20

Paul Reads Money Essays

Reasonably Happy with Paul Ollinger ·

2024/02/21

In this special “where has Paul been?” episode, Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include:Adventures in Affluence: Dry Cleaning - why Paul got freaked out when he starting thinking about how much he spends on dry cleaning every year. Gary v. Jerry: Why Gary Gulman Resents Rich People -Gary Gulman is an amazing comedian, but he harbors some very negative attitudes toward

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41:33

Race and Money with Coleman Hughes (Encore)

Reasonably Happy with Paul Ollinger ·

2024/02/06

Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.” Coleman has a new book out this week called 'The End of Race Politics: Arguments for a Colorblind America,’ in which he confronts the "failed corporate diversity and inclusion efforts and poisonous race-based policies that hurt the very people they intend to help." Coleman has been featured in the New York Times, The Wall Street Journal, The National

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51:58

The Joys and Anxieties of Wealth (Encore)

Reasonably Happy with Paul Ollinger ·

2023/12/28

Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of Boston College’s Center on Wealth and Philanthropy, Paul is the co-author of 'The Joys and Dilemmas of Wealth,' a 2010 report that is one of the most insightful studies of the ultra-affluent ever. We discuss how the fears and joys that come with being rich are often two sides of the same coin. And how Paul, a former Jesuit priest strongly influenced by Karl

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70:26

Dr. Drew Pinsky on Careers, Money, and Fame (Encore)

Reasonably Happy with Paul Ollinger ·

2023/12/27

This is a special holiday encore of the 2nd episode of Crazy Money with Dr. Drew, which ran Jan 30, 2019. Dr. Drew offers candid insight into the ups and downs of a career in broadcasting and medicine. From Loveline to Celebrity Rehab, Dr. Drew has been a staple on radio and cable television for over 30 years, but that doesn’t mean he’s rich — he’s got triplets to get through graduate school, after all. But he is definitely conversant on almost any topic you throw at him, including opera, coffee and

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61:00

How to Live a Stress-free Financial Life with Jared...

Reasonably Happy with Paul Ollinger ·

2023/12/19

Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like your house, your car, and how much you pay for college, makes all the difference. A renowned investment strategist and author, Jared is widely recognized for

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310 results

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