
Reasonably Happy with 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.
Latest episodes

May 21, 2024 • 51min
Andrew Yang on Our Broken Political System (Encore)
Former Presidential candidate Andrew Yang discusses his new book 'Forward' and the importance of structural reform in politics. He shares his teenage years and music interests, addresses money's influence in politics, the need for entitlement reform, and why politicians should be paid more. Yang advocates for universal basic income, open primaries, and ranked choice voting to combat political polarization and improve the system for all.

May 14, 2024 • 1h 5min
The Third Path with Jordan Harbinger
Jordan Harbinger is one of the most popular podcasters in North America, but it all started by accident. As a young University of Michigan grad, Jordan decided to go to law school because it was something to do after college and eventually ended up at a Wall Street firm. A multi-linguist, Jordan traveled and met new people all over the world. He eventually started teaching networking to other young adults. The tapes—compact discs, actually—of his presentations became so popular that he decided to upload them to a central server. Thus did he unintentionally become a very early podcaster. Today,"The Jordan Harbinger Show” generates over 10 million downloads per month and features conversations with huge guests like Ray Dialo, Simon Sinek, Mark Cuban, Neil deGrasse Tyson, Tony Hawk, and hundreds more. In this converation, Jordan and I discuss:
What job interviewers are really looking for
The thing he asked Kobe Bryant, just months before the basketball star’s death.
The difference between NY and London law firms
Why he won’t accept gambling ads on his show
The scandals other prominent podcasters have faced recently and what Jordan believes he owes his audience in terms of the ethics of his own behavior.
Learn more about Jordan / listen to the Jordan Harbinger Show here.
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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: podcasting, Zoom, languages, law school, career paths, teaching, integrity.
Please stop reading and have a great day. Paul loves you.

May 7, 2024 • 52min
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.

Apr 30, 2024 • 1h 2min
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.

Apr 24, 2024 • 56min
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.

Apr 16, 2024 • 1h 10min
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.

Apr 9, 2024 • 42min
The Wealth Money Can’t Buy with Robin Sharma
Leadership expert Robin Sharma discusses the dangers of money-focused thinking, finding joy in work, lessons from billionaires, and the 8 forms of wealth beyond financial in his latest book. Insights on mastery, purpose, God, and the importance of wellness, family, community, and service.

Apr 4, 2024 • 1h 7min
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.

Mar 29, 2024 • 1h 5min
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
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Mar 20, 2024 • 1h 4min
The Narcissist Next-door with Dr. Ramani Durvasula
Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In this insight-rich conversation, Dr. Ramani explains the traits and behaviors of narcissistic individuals, how they hijack our well-being, and the motivations behind their attention-seeking behavior. She also relieves Paul of the sneaking suspicion that he might be a narcissist. Other topics include:
Gender and narcissism (ladies is narcissists too!)
The continuum and different types of narcissism, including: grandiose, malignant, neglectful and also self-righteous narcissism (Paul’s favorite!)
How social media has amplified narcissistic behaviors and their impact on society.
Gaslighting and other tools narcissists use to sow self-doubt.
Which cities has more narcissists, Los Angeles or Washington D.C.?
The Different roles that evolve in narcissistic family systems (the golden child, scapegoat, fixer, peacekeeper, invisible child, and truth seer)
The correlation between ADHD and narcissism
The process of healing from narcissistic abuse and moving towards a thriving life.
Learn More About Dr. Ramani Here:
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