246 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

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).

    Living The Constitution with AJ Jacobs

    Living The Constitution with AJ Jacobs

    Good morrow, chum! My guest this week is A.J. Jacobs, author of the new / amazing book 'The Year of Living Constitutionally: One Man’s Humble Quest to Follow the Constitution’s Original Meaning’, in which A.J. chronicles his year of living as an 18th Century citizen, including writing letters with quill and ink, carrying a musket around the Upper West Side of Manhattan while wearing colonial garb, and celebrating election days with cake and rum! It’s the latest of his year-long experiments in living for which A.J. is so well known. As his website describes him, "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 the only 3-time Crazy Money guest in history of the world! Huzzah! I’m such a fan of AJ’s becuase he is a true original. He is smart, funny, and just the right amount of kooky. He’s also on a misison to make the world smarter, more aware, and more grateful. So that’s cool. He lives in New York City, very near where Paul's family will soon be living. In this fabulous conversation, Paul and A.J. discuss:


    Originalism v. Living Constitutionalists

    The way the Constitution is like a Rorschach test

    How elections used to be parties with beer and cake

    The balance between individual rights and the common good

    What are rights? And who decides which rights to prioritize?

    The disproportionate power of the Executive Branch


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    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:  Constitution, originalism, living constitutionalism, individual rights, common good, abortion rights, free speech, society, interpretation, democracy, government, people, age and health of the president, executive orders, Supreme Court, Constitution, First Amendment, Second Amendment. Please stop reading and have a great day. Paul loves you. 

    • 51 min
    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

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