Reasonably Happy with Paul Ollinger

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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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.

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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.

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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.  

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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.

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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.

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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.

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Sara Gay Forden is the author ofHouse of Gucci: A Sensational Story of Murder, Madness, Glamour, and Greed,on which director Ridley Scott based his star-studded film.The Economist named House of Guccione of its best books of the year, adding that it reads “like a novel,” which it totally does. The book is much more comprehensive story about the Gucci legacy than the movie, but both culminate in the murder of Maurizio Gucci, former Gucci CEO and grandson of Guccio Gucci, founder of the iconic fashion house. On March 27, 1995, a hit man gunned Maurizio down in the foyer of his 4-story Renaissance-style office and apartment building. His ex-wife, Patrizia, had hired the gunman because Maurizio’s impending marriage meant Patrizia’s alimony would be cut in half.As the sub-title suggests, the Gucci saga is a morality play about the sad by-products of wealth, fame, and status. Not only does being rich and famous not make you happy, but sometimes, it can get you killed. A business journalist with a knack for digging out compelling stories, Sara covered Milan's fashion industry, landing stories about family-owned designer labels like Armani, Versace, and Prada in the Wall Street Journal, Women’s Wear Daily, W, and Bloomberg News. She spent years researching and writing HoG, which came out 20 years ago and finally made its way to celluloid (okay, digital) in November, 2021. Today, Sara leads Bloomberg's reporting efforts on corporate influence and the scrutiny of major tech brands like Amazon, Apple, Facebook, and Google. Learn more about Sara on her website. 

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Julie Lythcott-Haims is passionate about raising self-sufficient kids and helping them find their unique path into adulthood. The former Dean of Freshman at Stanford University, Julie is the author of several books including How To Raise An Adult and Your Turn: How to Be an Adult, both of which we discuss today. In this amazing, smart, and no B.S. conversation, Julie and I discuss:

What success means and how we can model it for our children

Why affluent parents are more likely to over-parent.

Why parents freak out about our kids’ college decisions

What Rudolph the Red-Nosed Reindeer can teach us about career plans

Julie holds degrees from Stanford, Harvard Law School, and holds and California College for the Arts. She serves on several boards, including LeanIn.org, Common Sense Media, and Parents magazine. She has appeared on NPR, Good Morning America, Today, and mega podcasts like the Rich Roll show. Her TED Talk has been viewed over 6 million times. In other words, she’s, like, super-smart and totally interesting. You should totally listen to our discussion. 

Learn more about Julie on her website: https://www.julielythcotthaims.com/


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When it comes to money, there are two approaches: love or fear.” That’s what Ken Honda writes in his latest work, Happy Money: The Japanese Art of Making Peace with your Money. Ken’s books on money have sold over 8 million copies worldwide. On today’s show, we talk about how we can:

Feel worthy of money

Say Arigato (thank you) to money 

How to make money work in your marriage

Make peace with our childhood money experiences

 Ken was 29 when he first “retired” to welcome his newborn daughter in the world. He had owned a consultant and accounting business, so successful it had allowed him to close up shop and spend his days with the apple of his eye. Little did he realize his “second” career, impacting millions by helping them heal their relationship with money, was about to begin. That essay was the start of what would become Happy Money, the book we discuss today.  

Learn more about Ken on his website: https://kenhonda.com/


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Overthinking is so deeply ingrained in humanity that it shows up as a theme in Buddhism, Stoicism, Shakespeare, and the songs of Barenaked Ladies. Jon Acuff joins us today to discuss his book, Soundtracks, The Surprising Solution To Overthinking. Jon is a New York Times bestselling author of seven books whom Inc. included on their list of Top 100 Leadership Speakers. His writing has been translated into more than a dozen languages and has appeared in Reader’s Digest, Fast Company, The Harvard Business Review andTime Magazine. In this lively conversation, Jon and I discuss: 

90’s power pop (the music of Counting Crows, Fastball, Marcy Playground )

Parenting teens and how to help our kids with their negative soundtracks

How to (or not to) start a new career

Performing as the opening act for Dolly Parton

 Listen to Jon’s podcast All It Takes is a Goal and learn more about him on his website. **Rate and review Crazy Money HERE.** Email Paul by clicking here.

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