Reasonably Happy with Paul Ollinger

Latest Episodes:

TED's Chris Anderson on Infectious Generosity Mar 14, 2024

Show notes

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 life
MrBeast and the phenomenon of performative philanthropy
How gratitude can foster a sense of generosity and empathy
The contribution TED has made to the world by providing a platform to share valuable ideas.
How one, small act of kindness can spark generosity in others
Chris was born in Pakistan where his father was "an eye surgeon and evangelical Christian who ran a mobile hospital. He attended school in the Himalayan mountains of India before transferring to a boarding school near Bath, England. He went on to study philosophy, politics, and economics at Oxford, then found himself captivated by the personal computer revolution in the mid-1980s. He launched computer magazines via Future Publishing and eventually published 150 titles and employed 2,000 people. Using the proceeds of his success, Chris established a foundation to tackle tough global issues through media, technology, entrepreneurship, and ideas. In 2001, that foundation acquired the TED Conference, then an annual meeting of luminaries in the fields of technology, entertainment, and design, held in Monterey, California. Chris left the publishing world to work on TED full-time. In the next two decades, TED expanded to include the TED Prize, Ted-Ed, and the licensing of its name via TEDx, local, independently-produced conferences around the globe. Learn more about Chris and the book on InfectiousGenerosity.org.
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Mike and Paul’s Road Trip Mar 05, 2024

Show notes

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 Crazy Money
Life in general
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Topics addressed on Crazy Money 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, wealth, wealth management.
If you haven’t found what you’re looking for in the words above, you’re probably not going to find them down here. Seriously, all the important stuff is up yonder.
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On Fire for Life with John O’Leary Feb 28, 2024

Show notes

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 globe. John is also the author of the best-seller On Fire!: 7 Choices to Ignite a Radically Inspired Life and In Awe: Rediscover Your Childlike Wonder Unleash Inspiration, Meaning, and Joy. He hosts the Live Inspired podcast. John and I have a lot in common. We were both one of six kids in a big, Catholic family and raised by amazing parents who were married for over 50 years and whose humility and grace inspire us to this day. We’re both husbands and dads and both want our audiences to be radically aware of the value of their lives and the opportunity to make every day count. In this conversation, we discuss the importance of:
Living in the moment
Gratitude
Family
Courage
Friends who will fight for you
Finding your Talents
Learn more about John on his website.
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Subscribe to us on YouTube here.
Topics addressed on Crazy Money 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, wealth, wealth management.
If you haven’t found what you’re looking for in the words above, you’re probably not going to find them down here. Seriously, all the important stuff is up yonder.
Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Reads Money Essays Feb 21, 2024

Show notes

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 people who have more than he does.
The Dreaded H-Word: Should Labors of Love be Tax-Deductible? - Why Paul got so upset when the IRS got judgy about this podcast.
🔥Paul publishes these essays (about) every other Tuesday. You should subscribe HERE. 🔥
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Race and Money with Coleman Hughes (Encore) Feb 06, 2024

Show notes

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 Review, Quillette, The City Journal and The Spectator. He's appeared on many TV shows and podcasts including Real Time with Bill Maher, Making Sense with Sam Harris and the Jordan B. Peterson podcast.
In this conversation from summer of 2022, Coleman and I talk about:
The Racial Wealth Gap and its origins,
Why government action including reparations is not a solution
Whether 100% equality among all races is possible or even desirable,
How progressive policies that supposedly help African-Americans are actually holding them back and…
What issues we should focus on if we actually want to empower Black Economic Autonomy.
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Follow Coleman on Twitter and hear his music here.
Topics include DEI, race, racial wealth gap, reparations, Ibram Kendi, Robin DiAngelo, economics, inequality.
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The Joys and Anxieties of Wealth (Encore) Dec 28, 2023

Show notes

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 Marx, has come to appreciate more fully the humanity of the affluent. Learn more about Paul Schervish here. This episode was posted originally in April, 2022.
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Dr. Drew Pinsky on Careers, Money, and Fame (Encore) Dec 27, 2023

Show notes

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 Ulysses S. Grant. Oh, and doctor stuff. He knows about that too. Find out more about Dr. Drew on his website.
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How to Live a Stress-free Financial Life with Jared Dillian Dec 19, 2023

Show notes

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 his keen insights into market psychology and his ability to explain complex financial concepts in an accessible manner. He is also the author of the acclaimed book 'Street Freak: Money and Madness at Lehman Brothers' and the editor of the popular financial newsletter 'The Daily Dirtnap', where he shares his valuable perspective on the markets. Pre-order his new book, ’No Worries: How to Live a Stress-Free Financial Life’ here. On this week’s episode, we discuss:
Striking the balance between being a cheap f*ck and a high roller.
Why renting is often a much better idea than buying a home.
How much student debt is okay.
The five asset classes you should own in “The Awesome Portfolio"
Jared also graciously shares insights into his bipolar disorder and the side effects of the meds he takes. In so doing, he continues to help de-stigmatize mental illness. And for that, I thank him.
See Paul live in comedy mode:
Austin, Jan 11 - Buy Tickets Here
San Francisco, Feb 22 - Buy Tickets Here
Nashville, Feb 28 - Buy Tickets Here
🔥Learn and laugh by reading Paul’s Substack here. 🔥
🚀 Follow Paul on Instagram here. 🚀
DISCLAIMER: This episode contains a discussion of investment strategies and theories but in no way should be considered personal financial advice. Investing in any of the asset classes mentioned can result in material losses.
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Judd Apatow on Money, Fame, and Adam Sandler (Encore) Dec 13, 2023

Show notes

Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, directing, developing talent, and getting his family together for dinner. Judd has accomplished so much in his career that, in retrospect, his success appears to have been pre-ordained. But despite his massive success in the past 20 years, he never forgets his early struggles. In this week’s encore episode from Feb ’22, I speak with the writer / director / producer behind iconic comedy films such as Anchorman, Trainwreick, This is 40, and The 40-Year-Old Virgin about:
Why Adam Sandler paid $50 more in rent than Judd when they were roommates
Why he didn’t worry too much about finances as a young comedian
How failure prepared him to handle success
Being creative during a pandemic
Buddhism and stuff
Catch Paul Ollinger live (or tell your friends to go):
Austin, Jan 11 - Buy Tickets HERE
San Francisco, Feb 22 - Buy Tickets HERE
Nashville, Feb 28 - Buy Tickets HERE
🔥Learn and laugh by reading Paul’s Substack here. 🔥
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Author Gary Sernovitz Dec 05, 2023

Show notes

Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you possess either an interest in finance or a robust / dark sense of humor, The Counting House will make you laugh and, at times, cry in empathy with the protagonist. Gary has spent the last 25 years observing how money works from inside Goldman Sachs and the private equity business, bringing a keen writer’s eye to the money business through two previous novels, a non-fiction account of the oil and gas industrial, and a bunch of essays in The New York Times, The New Yorker and The Wall Street Journal. A Milwaukee native and longtime resident of New York, Gary now lives in New Orleans with his wife and daughter. See more about Gary and The Counting House here.
In this conversation, Gary and I discuss:
Investing with the constraints of a modern university stakeholders
Whether your performance is your identity
The state and cost of college
Writing as a side hustle while working full-time in finance
See Paul live in comedy mode:
Austin, Jan 11 - Buy Tickets Here
San Francisco, Feb 22 - Buy Tickets Here
Nashville, Feb 28 - Buy Tickets Here
🔥Learn and laugh by reading Paul’s Substack here. 🔥
🚀 Follow Paul on Instagram here. 🚀
Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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