245 episodes

Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).

Crazy Money with Paul Ollinger Paul Ollinger

    • Business
    • 4.9 • 427 Ratings

Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).

    Being Human at Work with Kim Scott, author of 'Radical Candor’

    Being Human at Work with Kim Scott, author of 'Radical Candor’

    ‘Radical Candor’ author Kim Scott once had to inform a colleague that they smelled bad….like, really bad. She was able to do so becuase she had created on her team a culture or radical candor. No, this doesn’t mean you can just walk up to colleagues and say, “you stink!” or “nice shirt, bozo!” On the contrary, radical candor is a culture where authentic personal caring co-exists with direct challenges. Lacking this combination, workplace communication falls into one of three meaningfully-less desirable buckets: 1. Obnoxious Aggression, 2. Ruinous Empathy, and 3. Manipulative Insincerity. In this conversation, Kim explains how radical candor can generate respect, collaboration, better relationships, and improved performance. Kim also addresses the challenges of perfectionism and the application of radical candor in marriages and parenting. She emphasizes the need for open communication, soliciting feedback, and expressing appreciation. See - that’s what you should be doing with your teenagers - expressing appreciation…before you tell them to put on deodorant! :-)

    Kim also discusses:

    What Sheryl Sandberg taught her about radical candor

    The way culture affects communication styles

    Whether you can bring your whole self to work in an increasingly politicized world.

    Whether Google’s Gemini AI debacle would be less likely to happen in an environment of radical candor


    Listen to the Radical Candor Podcast here and BUY Kim’s new book, 'Radical Respect' here. 


    💰Rate and review Crazy Money here. 💰

    🔥 Register for Paul’s thought-provoking newsletter here.🔥

    🎤 See Paul LIVE for telling of comedy jokes here. 🎤


    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, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth management, culture, society, status, ambition, accomplishment, perfectionism. Today’s episode covers: radical candor, radical respect, workplace communication, feedback, culture, collaboration, respect, individuality, radical candor, radical respect, workplace culture, feedback, hierarchy, perfectionism, marriages, parenting. Please stop reading and have a great day. Paul loves you. 

    • 1 hr 1 min
    Power Couple: Debbi “Mrs.” Fields and Wade Shealy

    Power Couple: Debbi “Mrs.” Fields and Wade Shealy

    Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his start selling Bibles door-to-door then went on to develop and sell > $3 billion in resort real estate over the next few decades, including Hampton Island, GA whose residents include Ben Affleck / Jennifer Lopez and Robert / Lydia Monday. He is now CEO of Third Home, a vacation home sharing platform that empowers its members to see the world. In this week’s epiosde, these two wildly accomplished humans share lessons about entrepreneurship, friendship, and raising stable kids in an atmosphere of affluence. Debbi tells the story of how she went from Oakland A’s ball girl to cookie kingpin and her commitment to quality over cost control. She also tells us how she kept a positive attitude when circumstances compelled her to give up control of the company. Wade emphasizes the importance of motivation, positive attitude, and controlling one's thoughts in achieving success. Both discuss their commitment to friendship. Learn more about ThirdHome here.


    💰Rate and review Crazy Money here. 💰

    🔥 Register for Paul’s thought-provoking newsletter here.🔥

    🎤 See Paul LIVE for telling of comedy jokes here. 🎤



    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, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth management, culture, society, status, ambition, accomplishment, perfectionism. Today’s episode covers: entrepreneurship, customer experience, real estate, motivation, positive attitude, friendships, family, friendship. Please stop reading and have a great day. Paul loves you. 

    • 56 min
    Death, Dying, and Israel with Rabbi Steve Leder

    Death, Dying, and Israel with Rabbi Steve Leder

    Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times best-selling author of several books, including 'For You When I Am Gone’ and 'The Beauty of What Remains,’ both of which pertain to death and dying. I had planned on speaking with Steve primarily about death for an hour, but our conversation covered everything from regret to forgiveness to the life of a rabbi. He shares lessons about fund-raising, his thoughts about whether Scripture is based on fact or truth, and the conflict of conscience he experienced when counseling a temple member who had ALS about her assisted suicide. Finally, Rabbi Leder speaks frankly about what Israel means to him and the tragic complexity of the war between Israel and Hamas.

    Follow Rabbi Leder on Instagram here. 

    • 💰Rate and review Crazy Money here. 💰
    • 🔥Register for Paul’s thought-provoking newsletter here.🔥

    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, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth management, culture, society, status, ambition, accomplishment, perfectionism. Today’s episode covers: regret, joy, sadness, forgiveness, fundraising, preaching, teaching, relationships, advice, conscience, ALS, end-of-life decisions, euthanasia, Jewish law, compassion, Israel, Middle East, Gaza, Hamas. Please stop reading and have a great day. Paul loves you. 

    • 1 hr 10 min
    The Wealth Money Can’t Buy with Robin Sharma

    The Wealth Money Can’t Buy with Robin Sharma

    Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, The Monk Who Sold His Ferrari, The Everyday Hero Manifesto, and Who Will Cry When You Die?, Robin has a new book out called The Wealth Money Can’t Buy in which he examines the ways we can all develop happiness with and beyond financial wealth. In this conversation, Robin shares with me insights from the book, specifically: 


    The danger of focusing solely on money

    How to find joy in your craft

    What his work with billionaires has taught him about money and life

    Why and how he started writing

    Whether he believes in God

    Where the word “coach” comes from

    The benefits of mastery

    And, the 8 forms of wealth: wellness, family, craft, money, community, adventure, service.

     

    Learn more about Robin and his new book on his website.

    • 💰If you enjoy Crazy Money, please leave us a rating here. 💰
    • 🔥Register for Paul’s thought-provoking newsletter here.🔥

    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, ambition, accomplishment, perfectionism. Please stop reading and have a great day. Paul loves you.

    =====

    Takeaways

    Find joy and fulfillment in your craft, no matter what you do

    Don't focus solely on financial wealth; pursue all eight forms of wealth: growth, wellness, family, craft, money, community, adventure, and service

    In difficult times, practice meditation, visualization, and prayer (MVP) to build resilience

    Stay in the pain and learn from it; it can lead to personal growth and wisdom

    Lead with kindness and generosity, and give gifts to others without expecting anything in return

    • 41 min
    America’s Government Teacher, Sharon McMahon

    America’s Government Teacher, Sharon McMahon

    Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience through “the fascinating world of democracy, politics, and history.” In the process, she is proving that Americans—and other good people around the globe—are hungry for unbiased political context and analysis. "With a heart for education and a mission to clear up political confusion,” Sharon has become known as America’s Government Teacher. And she’s such a clear and compelling teacher that over a million people subscribe to see her reels and stories that offer in-depth and unbiased background to the most important politics issues of the day. Sharon leverages her passion for history and government to promote knowledge, understanding, and TRUTH. Her work is strengthening democracy during a time when it is most urgently need. For that, Crazy Money salutes her! In today’s episode, Paul and Sharon discuss:


    The increasing politicization of the American classroom and the importance of critical thinking 

    The broken two-party system and electoral college

    A purely hypothetical 2024 election between butter and olive oil, and the pros and cons of voting for a 3rd Party Candidate, I Can’t Believe It’s Not President

    What it was like to interview the VPOTUS, Kamala Harris

    Sharons' book, 'The Small and the Mighty,' which explores the stories of unsung Americans who changed the course of history.


    Learn more about Sharon’s book and podcast here. 

    • 1 hr 6 min
    Poor Kid Makes Millions Trading, Fights Inequality with Gary Stevenson

    Poor Kid Makes Millions Trading, Fights Inequality with Gary Stevenson

    Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his gift for mathematics landed him a spot at London School of Economics (alma mater of Mick Jagger, Margaret Thatcher, and George Soros) where he attended with the sons and daughters of the global elite. His skill at a card game won him a job on Citibank’s trading desk and he went on to earn multi-million dollar—er, pound sterling—bonuses in his early 20s. Gary eventually become Citi’s top trader but the game started to take a physical toll on him. The stress, pressure, and moral conflict of betting against poor people—at least that’s how he saw it—led him to leave trading and begin to address growing income inequality around the globe. In this fast-paced and insight-rich conversation, Gary and Paul discuss:

    Gary's new memoir, The Trading Game: A Confession.

    The risks of trading currency

    How he felt when he got his first bonus of $750,000 

    Bias against working-class people

    Why he knew it was time to quit the industry 

    The positive role of short-sellers in a market

    His YouTube challenge, Gary’s Economics


    Hot to tax billionaires more


    ⭐ Subscribe To Paul’s Substack HERE. (Seriously, Do It!)⭐
     ✍️ Rate And Review Crazy Money HERE.  (Seriously, Do This Also!) ✍️
    🎤See Paul’s Live Comedy Dates HERE. 🎤

    • 1 hr 5 min

Customer Reviews

4.9 out of 5
427 Ratings

427 Ratings

whatsuproger ,

Always Interesting

I look forward to Paul’s podcasts and essays. They always get me thinking and/or make me laugh. His work goes far beyond just money, and deep into our behaviors.

clw987 ,

Great stuff!

Paul’s curiosity leads him to dig in and deliver a fabulous podcast. His guests are interesting and Paul’s interview style feels easy and informed. Great stuff!

secatlanta ,

Smart and funny

A compelling listen. Great guests and worthy topics that don’t get enough air time elsewhere.

Top Podcasts In Business

Private Equity Podcast: Karma School of Business
BluWave
Money Rehab with Nicole Lapin
Money News Network
REAL AF with Andy Frisella
Andy Frisella #100to0
The Ramsey Show
Ramsey Network
The Prof G Pod with Scott Galloway
Vox Media Podcast Network
The Diary Of A CEO with Steven Bartlett
DOAC

You Might Also Like

Earn & Invest
Jordan Grumet (Doc G)
The Stacking Benjamins Show
StackingBenjamins.com | Cumulus Podcast Network
Afford Anything
Paula Pant | Cumulus Podcast Network
The Financial Samurai Podcast
Sam Dogen: Financial Samurai founder, personal finance blogger
Mile High FI Podcast
Carl Jensen & Doug Cunnington
Two Sides of FI
Jason and Eric