

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

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

Mar 29, 2022 • 52min
Fixing Financial Chaos with Joe Saul-Sehy - Ep 140
41% of people who make over $200k per year still cry about money. That’s the finding of a recent study that Paul discusses this week with Joe Saul-Sehy, Creator and co-host of the Stacking Benjamins podcast AND author of Stacked: Your Super-Serious Guide to Modern Money Management. These two handsome bald fellas also chat about:
The double life Joe was living as a young financial planner
How he hit bottom when his car ran out of gas
What you want in—and how much you should pay for—wealth management
Whether or not you should manage your own money
If you want to give Paul a birthday present, Rate and Review Crazy Money! And/or Follow Paul on Instagram. Order Joe’s book here. You’re the best. Really. I swear. (I mean, Paul swears.)

Mar 23, 2022 • 47min
What’s Your Problem? with Jacob Goldstein - Ep 139
Jacob Goldstein is the author of Money: The True Story of a Made Up Thing and former co-host of Planet Moneywhere he worked for over a decade. His new podcast, What’s Your Problem? from Pushkin Industries explores how company founders solve consumers’ problems and what problems they themselves run into along the way. On today’s show, we tackle the following:
The question that Ira Glass described as “the most stoner question ever”
How cash transactions worked in these United States before we had dollar dollar billz, y'all
Why you making more money doesn’t mean someone else will make less
How working at Pushkin is different than working at NPR and the Wall Street Journal
The name of the very first compact disc he ever bought.
Jacob is a former staff writer at the Wall Street Journal, the Miami Herald, and Bozeman Daily Chronicle. His work has appeared on This American Life, Morning Edition, and in the New York Times Magazine. He is a husband and father of two. He spoke with me from his soundproof closet in Brooklyn, USA. Check out What’s Your Problem?here.
⭐ Get 15% off your SideCar carrier with promo code CRAZYMONEY by clicking HERE.⭐
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Mar 15, 2022 • 16min
Comparison and the Ultimate Money Delusion - Ep 138
If you think Paul Ollinger can’t draw poignant and funny lessons about money from the 1996 box office smash, Jerry Maguire, you are sadly mistaken. On this week’s very special spring break episode of Crazy Money, Paul reads a couple of his recent reflections on comparison and the delusions we all cling to about the power of wealth. Spoiler alert: money—past a certain point—will not complete you. And comparing yourself to your friends (or enemies) will make you miserable. Full stop. Here’s what we’ll be talking bout today:
Stop Keeping Score: How to Quit Measuring Success by Net Worth, Fancy Titles, or TikTok Views
Money Isn’t What You’re Missing: What I’ve learned after years of studying money and happiness
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Mar 8, 2022 • 41min
Why Things Are Better than You Think with Grant J. Ryan - Ep 137
Many people want you to believe that the world is in worse shape than ever. They assert that wages are stagnant, inequality is growing and the earth is heating up. But for the vast majority of humanity, things have never been better.
Racism, sexism, and homophobia are at their lowest rates in history.
We have more and better food than kings and queens could have dreamt of in the 18th century.
We have access to clean water, indoor plumbing, effective healthcare, and technology that even billionaires couldn’t have gotten just 20 years ago (the technology, not the plumbing).
So why the hell is everyone so freaked out all the time about the decline of civilization? In his new book Comparonomics, Grant Ryan shares a very simple tool to evaluate how the most important aspects of our lives have changed over the past 50 and 250 years, respectively. He also explores our innate biases that lead us to both respond to bad news and spread it around like the virus it is. Grant spoke to me from his home in New Zealand. Learn more about Comparonomicshere. YOU really should rate and review Crazy Money here. YOU should also follow Paul on Instagram. He’s funny.

Mar 1, 2022 • 58min
Founder of Russian Hedge Fund on Defying Putin with Bill Browder - ENCORE EPISODE
Bill Browder is the author of Red Notice: A True Story of High Finance, Murder, and one Man’s Fight for Justice, which is the best book I’ve read in a decade (and I read a lot of books). Red Notice is the story of how Browder turned a $25 million investment into a $4 billion hedge fund (Hermitage Capital) by exposing corruption in the newly opened Russian economy of the late 90’s and early 00’s. Eventually, Browder’s efforts to shine light on the newly privatized industries, cut too close to strongman, Vladimir Putin who kicked Browder out of the country and declared him a “threat to national security.” And that was just the beginning! Russian police officials took over his companies, used them to steal $230 million from the Russian treasury, framed Bill, and eventually arrested and killed his lawyer, Sergei Magnitsky. Today Bill lives under threat of retaliation and spends his time fighting to honor Sergei’s memory. This episode originally ran in May, 2019. Read more about Sergei Magnitsky here. Please RATE and REVIEW Crazy Money here. Follow Paul on Instagram here.

Feb 22, 2022 • 39min
LL COOL J - ENCORE EPISODE
Nobody works harder than LL COOL J. The musician, producer, actor, and entrepreneur has been playing at the highest levels of art, business, and culture since he burst on the scene at the age of 17, in 1985.For over 35 years, LL has pushed himself to achieve in all that he does while leading with spirit and character. And achieve he has. The two-time GRAMMY-winner and first ever Hip Hop Kennedy Center Honoree has recorded 14 studio albums, landing massive hits including Going Back to Cali, Mama Said Knock You Out, Rock The Bells, and many, many more. As an actor, he has played “Sam Hanna” on NCIS: Los Angeles for the last 12 years, appeared in hit films like In Too Deep, Any Given Sunday, and Wildcats, and starred in the NBC sitcom, In the House. In this special encore edition of Crazy Money, LL shares:
What he really wanted when he released his first record,
How he approaches potential business deals, and
Why he pours his soul into Rock The Bells, his company that elevates timeless and classic Hip-Hop culture by celebrating MC’s, DJ’s, Break Dancers and Graffiti artists on its website, found here.
**Please rate and review Crazy Money HERE.**Follow Paul on Instagram here.Topics covered in this episode include: hip hop, music, rap, culture, money, wealth, motivation, inspiration, persistence, work ethic, black money, racial wealth divide. About Crazy Money:Unlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered 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, affluence, wealth management, culture, society, status.

Feb 16, 2022 • 55min
Judd Apatow on Fame, Money, and the Creative Process - Ep 136
Judd Apatow doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, developing talent, and getting his family together for dinner. In this week’s episode, the writer / director / producer behind iconic comedy films such as Anchorman, This is 40, and The 40-Year-Old Virgin and I talk about:
Why Adam Sandler paid $50 more in rent than Judd when they were roommates
How failure prepared him to handle success
Being creative during a pandemic
Judd has accomplished so much in his career that, in retrospect, his success appears to have been pre-ordained. Despite his massive success in the past 20 years, he never forgets his early struggles and approaches every new project not knowing how it will be received. Having used Quarantine to crank out a George Carlin documentary, a new feature film (The Bubble), and a book, all his fans have lots new material to enjoy over the next few months. I am 364 pages into his new book (Sicker in the Head), and it’s fantastic. You should pre-order it here. RATE AND REVIEW Crazy Money here. Follow Paul on Instagram here. Have a wonderful day wherever you are. That is all.

Feb 9, 2022 • 55min
Olympic Economics with Apolo Ohno - ENCORE EPISODE
In this episode, Apolo Ohno and I go deep into the economic realities of becoming an Olympian. Due to the steep cost of coaching, training, equipment, and travel, many (perhaps most) athletes and their families go deep into debt in pursuit of a spot on the national team. And even for the few who make it, there is little preparation for post-Games remuneration and little preparation for a job “in the real world.” With eight Olympic medals (two of them gold), Apolo Ohno is America’s most decorated winter Olympian. He won his first major speed skating title at the tender age of 14, after only six months of training. He continued on to a career that played a major role in establishing short-track speed-skating in the 2002, 2006, and 2010 Winter Games. In his post-skating career, Apolo has worked as a sports analyst for NBC, a global ambassador for the Olympics, and a winner of ABC’s hit show, Dancing with the Stars. He finished the 2014 Ironman World Championship Triathlon in less than ten hours. Apolo now spends much of his time speaking to business and nonprofit leaders around the globe. His New York Times best-selling memoir, Zero Regrets, tells the story of success, setbacks and what it takes to become one of the top athletes in the world. His next book Hard Pivot, which tells the story of reinvention and tackling new challenges while maintaining his iconic positive attitude comes out later this month. Check out Apolo’s website here. Please take a second to rate (and review!) Crazy Money here. Follow Paul on Instagram here. This episode originally posted Sept, 2020. Produced and edited by Mike Carano Topics addressed in this episode include: performance, motivation, achievement, retirement, reinvention, regrets, Olympics, Olympians, athletes, reinvention, second careers.Topics addressed on Crazy Money include: Philosophy, Happiness, Contentment, Meaning, dreams, purpose, Success, Rat Race, Society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, Mid-Life Crisis, Business, Work, Careers, Retirement, Reinvention, Authors, Books, Consumerism, Values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management.