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Crazy Money with Paul Ollinger

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Crazy Money with Paul Ollinger

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...

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Recent Episodes of Crazy Money with Paul Ollinger


Mike Posner on Life Beyond Fame and Fortune

Mike Posner on Life Beyond Fame and Fortune

Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays and his song 'I Took a Pill in Ibiza' reached the top five on the Billboard Hot 100. Mike "had it all" at a young age and captured his lifestyle in the lyrics of his biggest hit: “A real big baller (who) made a million dollars and...spent it on girls and shoes.” But Mike wanted more—he wanted to live a life of meaning and purpose - to become the person he was supposed to be. As he shares in his re...

Episode 28 May 2024 46m and 10s


Andrew Yang on Our Broken Political System (Encore)

Andrew Yang on Our Broken Political System (Encore)

Andrew Yang is a former Presidential and NYC mayoral candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for structural reform to safeguard our democracy. He lays all this out in his new book, ‘Forward,' which we discussed today. We also discuss Andrew's life as a teenager, his obsession with post-punk bands like The Smiths, Depeche Mode, and Nine Inch Nails, why he didn’t do drugs as a teenager, and how his parents felt when he got his ear pierced. More to the point of his political career...

Episode 21 May 2024 50m and 56s


The Third Path with Jordan Harbinger

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 podcast...

Episode 14 May 2024 1h, 4m and 32s


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...

Episode 7 May 2024 51m and 32s


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 gener...

Episode 30 April 2024 1h, 1m and 48s


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 ra...

Episode 24 April 2024 56m and 22s


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 co...

Episode 16 April 2024 1h, 10m and 16s


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...

Episode 9 April 2024 41m and 48s


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 unbias...

Episode 4 April 2024 1h, 6m and 56s


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 star...

Episode 29 March 2024 1h, 5m and 14s

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