

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

Jul 26, 2022 • 40min
Racial Wealth Gap with Coleman Hughes
Today’s guest is Coleman Hughes, he's a writer, podcaster and opinion columnist who specializes in issues related to Race, Public Policy and Applied Ethics. He 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. He's also a rapper who goes by the name Coldxman and his latest tracks can be found on Spotify and YouTube. In today's episode Coleman and I talk about the Racial Wealth Gap and its origins, why government action including reparations is not a solution whether a hundred percent of 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. All this and more with Coleman Hughes.💰If you enjoy Crazy Money, please leave us a rating here. 💰🔥Get Paul’s Substack newsletter here.🔥🔥Subscribe to us on YouTube here. 🔥Follow Coleman-Twitter - https://twitter.com/coldxmanWebsite - https://colemanhughes.org/YouTube- http://bit.ly/38kziumColdxman Music-http://bit.ly/3jXTwAr

Jul 19, 2022 • 44min
Buy this, not that! with Author Sam Dogen
Sam Dogen left his job in investment banking at age 34 to start his financial newsletter, Financial Samurai. He's got a new book out this week called “Buy This, Not That!” How to spend your way to Wealth and Freedom. Today Sam and I discuss his one word definition of 'Happiness', how wearing the right tie helped him get a job at Goldman Sachs, how he transitioned out of investment banking to become an independent financial writer, how the right plan is the key to surviving inflation and the ups & downs of the stock market, and why he advises young adults to forecast their professional misery. We also discuss his best and worst financial investments and among other things, the return on investment of private vs public school. If you enjoy Crazy Money, please leave us a rating here. Follow Paul’s Substack newsletter here.Subscribe to the Crazy Money YouTube channel here.Follow Sam-Twitter - https://twitter.com/financialsamurai Website - https://www.financialsamurai.com/Link to book - Buy This, Not That! https://www.financialsamurai.com/btnt/

Jul 12, 2022 • 54min
Soul in the Game with Vitaliy Katsenelson
Today’s guest is Vitaliy Katsenelson. He's an investor, writer and author of the new book ‘Soul in the Game : The Art of a Meaningful Life’. Nassim Nicholas Taleb, the author of The Black Swan calls the book deep, insightful, inquisitive and civilized, which is a pretty good description of Vitaliy himself. In this episode we discuss what it was like growing up in Russia, north of the Arctic Circle, how America did and did not fit with his expectations, which were set by all the American movies he had seen before he arrived at age 18. Whether rich people are actually happier, what we can learn about careers in comparison from Franz Schubert and Beethoven, what it means to be a student of life, and what may or may not happen in Ukraine. We recorded this conversation in June (2022). This is coming out in July, so I can't say what has or hasn't happened in the meantime. Just so you know. 💰 If you enjoy Crazy Money, please leave us a rating here. 💰🔥 Get Paul’s Substack newsletter here.🔥🔥 Subscribe to us on YouTube here. 🔥Follow VitaliyTwitter - https://twitter.com/vitaliykWebsite - https://contrarianedge.com/Link to book - ‘Soul in the Game : The Art of a Meaningful Life’

May 17, 2022 • 57min
Life after the PGA Championship with Rich Beem - ENCORE EPISODE
This is an encore episode with Rich Beem, winner of the 2002 PGA Championship, one of professional golf’s four major tournaments. Despite having won twice on tour prior to the PGA, Rich's win at Hazeltine was as unlikely as the groovy dance moves he busted out after sinking his final putt of the tournament. Describing himself as “the luckiest guy in the world,” Rich played the game loose and wide open, but the rising expectations of being a major champion became a distraction, and he never won again on tour. In this chat, Rich speaks candidly about:
Selling car stereos and grinding his way up the golf ladder,
Finding purpose and meaning in life as his PGA prospects began to dim.
The reason he tells his son that “what you shoot is not you”
Why he loves working as an analyst at Sky Sports
Rich was born in Phoenix, AZ, grew up in El Paso, TX and played college golf at New Mexico State University. Today Rich plays on the PGA Champions Tour and works as a TV golf analyst on Sky Sports in the UK and Ireland.(Originally posted November, 2020. Follow Rich on Twitter.
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May 10, 2022 • 1h 3min
The Problem with Choice with Barry Schwartz - ENCORE EPISODE
This is an encore epsiode with Professor Barry Schwartz, author of several books, including Why We Work and The Paradox of Choice. I spoke to Barry in August, 2020 about his findings in these two important books. Prevailing social wisdom is that more is better, and that more choices should yield much greater satisfaction. So why is it that the harder we work and the more affluent we become, the more depressed we get? More choice, Barry argues, not only overwhelms us, but raises our expectations and makes us doubt our decision-making. Too much choice increases our anxiety and makes us less happy. Could it be, even in our freedom loving country, that we have gotten too much of a good thing and that we would benefit from some guardrails in our lives? I’m sure there are those who would argue against it, but Barry’s research and conclusions here are quite persuasive. Barry Schwartz taught psychology at Swarthmore College for 45 years and is now Visiting Professor of Management at UC Berkeley’s Haas School of Business. He holds an M.A. and a Ph.D. from University of Pennsylvania, and a B.S. from New York University. His TED Talks on the topics of work, choice, and wisdom have been viewed over 20 million times.
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Produced and edited by Mike Carano Topics addressed on Crazy Money include: Philosophy, Happiness, Contentment, Meaning, Success, Buddhism, Stoicism, The hedonic treadmill, Mid-Life Crisis, Authors, Books, Consumerism, Anxiety, mental health, wealth, money, careers, values, and The Container Store.

May 3, 2022 • 50min
Hedge Fund Novelist with Jay Newman - Ep 145
Jay Newman makes BIG bets. In his 40 year hedge fund career, Jay was the guy who fought to recover deca-billion dollar debt defaults by countries like the Congo, Panama, and Argentina. Recouping from these deadbeat governments required long term thinking, stealthy patience, and giant cojones, the same attributes required to publish a debut novel, which Jay did earlier this year. The New Yorker called his new book, Undermoney a combination of “espionage, financial intrigue, and geopolitics with a cynicism developed through years of observing politicians and Wall Street titans up close.” And because the plot lines include Russian oligarchs, private militias, and Vladimir Putin, Undermoney is also “unexpectedly timely.” I’ve read it: it’s juicy and enticing. Learn more about Jay here.
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Apr 26, 2022 • 51min
The Puzzle of Life (with A.J. Jacobs) - Ep 144
A.J. Jacobs believes that puzzles can save the world. The famously obscure 4-time New York Times best-selling author of books like The Know-It-All, Thanks a Thousand, and The Year of Living Biblically tells us what we can learn from them in his new book The Puzzler: One Man’s Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life. We talked about some great life lessons A.J. gleaned from puzzles, including:
Start with the end in mind
Embrace the eraser (i.e. your first impression might not be accurate!), and most importantly,
PAY ATTENTION, KNUCKLEHEAD!
Join other readers in the quest to win A.J.’s $10,000 by clicking here.
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Apr 19, 2022 • 44min
Money and Comedy with Christian Finnegan - Ep 143
Description: Christian Finnegan is a comedian and actor, well known for his work on Chappelle’s Show and the popular sitcom, Are We There Yet? He has performed on Comedy Central Presents, Conan, The Late, Late Show with James Corden, and his five comedy specials are in regular rotation on all major streaming services. An avid music fan, Christian wants to connect formerly-cool middle aged people to the best in new music. Check out his Substack, New Music for Olds here.
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Apr 12, 2022 • 53min
The Joys and Anxieties of Wealth with Paul Schervish - Ep 142
Description: 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 upper class. Learn more about Paul Schervish here.
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Apr 5, 2022 • 56min
Mid-Life Career Re-invention with Chip Conley - Ep 141
Something happens to many of us in our 40’s or 50’s: having achieved a certain level of success, we yearn to find work that is an expression of who we are. Chip Conley can help with that. He founded and runs Modern Elder Academy, a school and retreat center dedicated to helping people navigate midlife and beyond. To do so, he draws on insights and wisdom earned over his own incredible career journey. For over two decades, Chip ran Joie de Vivre, the boutique hotel owner/operator that he founded in his 20s. In the depths of the Great Recession, the combination of medical crisis and market turmoil compelled Chip to sell out at the bottom of the market. While many might have given up, Chip forged ahead, reinvented and redefined who he was, all the while staying open to where that journey would take him. It eventually took him to Air BnB where become the in-house consigliere (among other things) for Air BnB CEO/co-founder Brian Chesky. Today, Chip writes, speaks, surfs, and provides the space and resources to help other “successful” people examine their lives and commit to positive paths forward. Learn more about Modern Elder Academy hereand Chip’s newsletter here. • 💪🏼 Rate and Review Crazy Money by clicking HERE.💪🏼 • 🦸♀️ Follow Paul on Instagram HERE🦸♂️ Topics covered in this episode: #purpose #wellness #community #travel #hotels #Airbnb


