
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

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.
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🎤 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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Mar 14, 2024 • 54min
TED's Chris Anderson on Infectious Generosity
Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues that YOU and I can improve the world by embracing our natural inclination toward generosity. He speaks not just of financial generosity, though that’s certainly a huge part of it, but also of creative generosity and generosity of spirit. In this conversation, Chris and I discuss:
The formula to determine if you are a net giver or a net taker in life
MrBeast and the phenomenon of performative philanthropy
How gratitude can foster a sense of generosity and empathy
The contribution TED has made to the world by providing a platform to share valuable ideas.
How one, small act of kindness can spark generosity in others
Chris was born in Pakistan where his father was "an eye surgeon and evangelical Christian who ran a mobile hospital. He attended school in the Himalayan mountains of India before transferring to a boarding school near Bath, England. He went on to study philosophy, politics, and economics at Oxford, then found himself captivated by the personal computer revolution in the mid-1980s. He launched computer magazines via Future Publishing and eventually published 150 titles and employed 2,000 people. Using the proceeds of his success, Chris established a foundation to tackle tough global issues through media, technology, entrepreneurship, and ideas. In 2001, that foundation acquired the TED Conference, then an annual meeting of luminaries in the fields of technology, entertainment, and design, held in Monterey, California. Chris left the publishing world to work on TED full-time. In the next two decades, TED expanded to include the TED Prize, Ted-Ed, and the licensing of its name via TEDx, local, independently-produced conferences around the globe. Learn more about Chris and the book on InfectiousGenerosity.org.
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Mar 5, 2024 • 1h 46min
Mike and Paul’s Road Trip
Join Paul and Mike on a road trip as they share memories of commuting, discuss the challenges of admitting what we want in life, ponder new names for the podcast, and delve into life, happiness, and philosophy.

Feb 28, 2024 • 50min
On Fire for Life with John O’Leary
A remarkable story of resilience and gratitude by John O'Leary who survived severe burns as a child. The podcast explores themes of living in the moment, gratitude, family, courage, and finding talents. It emphasizes the transformative power of love and grace, navigating through recovery, and embracing uniqueness for personal growth. The conversation inspires listeners to choose gratitude, love, and self-improvement in facing life's challenges.