Paul Ollinger

Reasonably Happy with Paul Ollinger

Comedy EN ↓ 335 episodes

Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection. words.paulollinger.com

Author

Paul Ollinger

Category

Comedy

Podcast website

words.paulollinger.com

Latest episode

Jul 8, 2026

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Episodes

"How to Be a Financial Grownup" with author and financial journalist Bobbi Rebell - Ep 35 15.10.2019

Bobbi Rebell is an award-winning TV anchor and personal finance columnist most recently at Thomson Reuters, the largest news organization in the world. She is also the host of the Financial Grownup podcast and the co-host of the Money with Friends podcast. Her Reuters column was syndicated to newspapers and websites worldwide. Before that, she was a reporter at PBS’ Nightly Business Report and hel...

Comedy Entrepreneur, Rick Bronson - Ep 34 08.10.2019

Rick Bronson is an award-winning comedian, magician, TV Host, and entrepreneur. He has worked with President Bill Clinton, Spinal Tap, Martin Short, The Smothers Brothers, and many other fascinating people. Rick is the recipient of 8 COCA Comedian of the Year awards, an AMPIA award for Best TV Host on his travel series, The Tourist, and many other comedy accolades.  Today, Rick owns and operates s...

"Stillness is the Key" with Author Ryan Holiday - Ep 33 01.10.2019

Ryan Holiday is the author of ten books, which have sold sold more than 2 million copies worldwide and been translated into 30 languages. World-class athletes, celebrities and political leaders use his lessons to achieve peak performance. His 2014 book, The Obstacle Is The Way, was read by the New England Patriots during their 2014 Super Bowl-winning season and by four-time major champion golfer R...

"Happiness" with Professor in Psychology, Yale University, Dr. Laurie Santos - Ep 31 25.09.2019

Our brains are not good at predicting what will actually make us happy. You think you want more money, more fame, and to be alone, but what will actually make you happy are more social connections and more gratitude. Dr. Santos’ course Psychology and the Good Life teaches students to live happier, more fulfilling lives, which is good because student rates of anxiety, depression, and suicidal thoug...

"Does happiness peak?" with Nobel Laureate and Economist Sir Angus Deaton - Ep 31 17.09.2019

Princeton economist and Nobel Prize-winner, Sir Angus Deaton co-authored a famous study concluding that well-being peaks at $75k/year in income. But the results of this research go much deeper and are widely misconstrued. The first question we wrestle with is "what does it mean to be happy?” We also get into health, opioids, and trout-fishing.  A native of Edinburgh, Scotland, Angus Deaton earned...

"Quit Like a Millionaire" with Authors Kristy Shen & Bryce Leung - Ep 30 10.09.2019

Kristy Shen grew up in abject poverty in rural China where her family lived on $.44 per day. Chronic hunger and worm-infested drinking water were regular parts of her youth. Her husband, Bryce Leung, is also a first generation Canadian, but from a more middle class background.  Early in their computer-programming careers, they committed themselves to frugality. In their early-30’s, with millions i...

"Chutzpah" with Author Inbal Arieli Ep - 29 03.09.2019

Israeli kids grow up in a world of uncertainty, with war and terrorism never far away. They are independent yet group-minded. They know that when they turn 18, they will serve in the Israeli Defense Force (IDF). Their parents don’t hover over them, obsess over every mistake, or give them trophies for losing.  In her new book, Chutzpah, Inbal Arieli argues that these traits uniquely prepare them fo...

"Rich People Have Problems Too" with Financial Therapist Brad Klontz - Ep 28 27.08.2019

Dr. Brad Klontz is a psychologist and certified financial planner. He helps his clients (many of whom are ultra-high net worth individuals or even billionaires) understand how what they learned about money as kids affects their attitudes and dysfunctions today.  This week, both Paul and producer Mike Carano take Brad's Money Disorder Assessment and discuss their results in the hope he can cure the...

Short-seller who goes after “bad guys" with Marc Cohodes - Ep 27 20.08.2019

Marc Cohodes has made a career betting against companies he suspects of fraud. So when two FBI agents showed up on his farm to tell him to stop Tweeting about MiMedx CEO Pete Petit, Marc says he knew something was rotten in the Marietta, GA biotech’s company’s operations.  Marc contends that MiMedx has been engaged in several dishonest practices and that Petit called in political favors from Georg...

Closing the Opportunity Divide with Year Up Founder and CEO Gerald Chertavian - Ep 26 13.08.2019

Gerald Chertavian is the Founder / CEO of “Year Up.”  According to the US Dept of Labor, there are 7.3 million unfilled jobs in the United States. At the same time, there are millions of young adults who are working way below their potential or not working at all. Year Up takes those who want to work, arms them with both technical and social skills, then connects them to employers who need motivat...

America's Got Talent finalist and two-time David Letterman guest ; Comedian Joe Matarese - Ep 25 06.08.2019

You’ve likely seen Joe Matarese on one of his many television appearances, including two sets on Late Show with David Letterman, five on the Late, Late Show with Craig Ferguson, or on his Comedy Central Presents half hour special, among many others. As a finalist on America’s Got Talent, Joe received a standing ovation from the 2,000-person crowd and all four celebrity judges.  With all these amaz...

Minimalism and Design with CEO of LifeEdited ; Graham Hill - Ep 24 30.07.2019

Graham Hill has a message for you: that big ol’ house of yours—and all the stuff in it—isn’t making you (or the environment) happy. His words are resonating. Graham’s two TED Talks on low-impact living and #minimalism have been viewed over 7 million times. A successful entrepreneur, Graham co-founded, ran and sold both SiteWerks and TreeHugger.com . Today he runs LifeEdited, which is dedicated to...

"Effective Altruism" with Oxford professor Dr. Will MacAskill - Ep 23 23.07.2019

Will MacAskill—whom Bill Gates describes as, “a data nerd after my own heart"—is Associate Professor in Philosophy and Research Fellow at the Global Priorities Institute, University of Oxford. Will’s academic research focuses on the fundamentals of effective altruism—the use of evidence and reason to help others by as much as possible with our time and money, with a particular concentration on how...

Glamour Magazine Editor-in-Chief ; Samantha Barry - Ep 22 09.07.2019

Samantha Barry is Editor in Chief of Glamour where she is responsible for setting the voice and mission of the publication.  As a young woman in Ireland, Sam once dreamed of being a war correspondent. Her early work in journalism took her all over the world, including stints in Nigeria, Burma, Pakistan, Iraq, Papua New Guinea, Burma, and many other turbulent locations where she worked for the BBC,...

"Power of the Upper Middle Class" with Richard Reeves of Brookings Institution - Ep 21 02.07.2019

If you’re in the upper middle class or above, today’s conversation might make you uncomfortable. In fact, my guest says that discussing his research ruins dinner parties with his affluent friends. Why? Because his studies conclude that the upper middle class keep all the societal goodies to themselves, and worst of all, he may just be right.  Named by Politico magazine as one of the top 50 thinker...

"Making Money after Growing up Poor" with Comedian and Radio Legend Adam Carolla - Ep 20 25.06.2019

When it comes to delivering hilarious, non-obvious wisdom through a microphone, Adam Carolla is the very best. Yes, Stern is amazing and Terry Gross is the patron saint of the modern interview, but for the improvisational spoken-word, Adam Carolla is the unique genius of our time. In addition to a decades-long radio career, he is also a comedian, actor, film director, auto racing enthusiast and on...

"The Vietnamese Refugee" with Mom and Entrepreneur Gianni Le Nguyen - Ep 19 18.06.2019

Gianni Le Nguyen fled Vietnam at the age of 5. Late one night in the early 1980s, her father wrapped his two young daughters in a fishing net, then rowed a basket boat out to meet a more seaworthy vessel a quarter mile offshore. They spent five days battling storms, illness and pirates who took everything Gianni’s dad possessed, including his official papers. Thus began a beauracratic mess that le...

"An Economist Walks Into a Brothel" with Author Allison Schrager - Ep 18 11.06.2019

Allison Schrager is the author of the new book, An Economist Walks into a Brothel in which she explores risk through the lens of prostitution, big-wave surfing and war. If you liked Freakanomics, you’ll dig this book too.   Allison is an economist, journalist at Quartz, and co-founder of LifeCycle Finance Partners, LLC, a risk advisory firm. She has been a regular contributor to the Economist, Reu...

Millennial Extraordinaire with Darrah Brustein - Ep 17 04.06.2019

In my mind, Darrah Brustein is the ultimate Millennial. Not because she writes, travels the world and has a weekly video series with Deepak Chopra called weekly "Diving Deep with Deepak & Darrah." While she does all of the above, she’s the ultimate millennial because she uses money as a tool to live a good life then uses that life to make more money! She is living the life she designed. And damnit...

"Red Notice" with Author and Hedge fund Legend Bill Browder - Ep 16 28.05.2019

Bill Browder is the founder and CEO of Hermitage Capital Management, the largest foreign investment fund in Russia until 2005. He grew an initial investment of $25mm to over $4 billion while challenging violent oligarchs. Bill eventually ran afoul of Vladimir Putin, kicked out of the country, and declared a “threat to national security." That was just the beginning. Russian police officials took o...

Brian Portnoy, author "The Geometry of Wealth" - Ep 15 21.05.2019

Brian Portnoy, Ph. D., CFA, is an expert at simplifying the complex world of money. In his two books, The Investor's Paradox and The Geometry of Wealth, he tackles the challenges of not only making better investment decisions but also how money figures in to a joyful life. He is currently the Head of Education at Magnetar Capital and has spent the last 25 years as educator, investor, and strategis...

The Importance of Gratitude with A. J Jacobs - Ep 14 14.05.2019

A.J. Jacobs is an author, journalist, lecturer and human guinea pig. He has written four New York Times bestsellers that combine memoir, science, humor and a dash of self-help. He is also editor at large at Esquire magazine, a commentator on NPR and a columnist for Mental Floss magazine. Learn more about A.J. on his website. **Please rate and review Crazy Money here. Follow Crazy Money on Facebook...

Growing up poor: Yancey Spruill and Susan Nicholas - Ep 13 07.05.2019

This week we continue to discuss “straddlers,” i.e. individuals who grew up working class but worked their way into white collar careers. Yancey Spruill grew up in a rough neighborhood in west Buffalo, NY where food stamps and eviction were part of his reality. He attended Georgia Tech and earned his MBA at Dartmouth’s Tuck School. Yancey worked on Wall Street for seven years then took two separat...

Alfred Lubrano, journalist and author, Limbo - Ep 12 30.04.2019

Alfred Lubrano is the Philadelphia Inquirer’s poverty reporter and the author of Limbo: Blue-Collar Roots, White-Collar Dreams. The book explores the conflicts within individuals who grow up working class but graduate into a white collar career. These “straddlers” are often torn between the culture that raised them and the professional world to which they aspired. Limbo has been quoted in Harvard...

Jean Chatzky, NBC Today Show Financial Editor - Ep 11 23.04.2019

Jean Chatzky, financial editor of NBC’s TODAY show, award-winning personal finance journalist, and host of the HerMoney podcast. She has written several personal finance books. Her latest, Women With Money has just hit shelves in bookstores, real and virtual. Go see Paul tell jokes this week at the North Carolina Comedy Festival. Show details and more dates available on  http://paulollinger.com/ev...

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