Crazy Money with Paul Ollinger Paul Ollinger

Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no nudity in either), and The Centrist Manifesto, all of which we discuss in this episode. The Chicago Sun-Times describes Charlie as someone who “combines a razor-sharp mind with a boatload of charm and impressive expertise in economics and foreign policy,” which might be why his students regularly pick him as one of Dartmouth's 10 best professors. Charlie is also the founder and Co-director of Unite America, a movement of Democrats, Republicans, and independents working together to to put voters first by fostering more representative and functional government. In March, 2009, Charlie ran unsuccessfully for the Congressional seat vacated by Rahm Emanuel who went on to become President Obama’s Chief of Staff. Charlie is a graduate of Dartmouth and holds a Master’s from Princeton and a Ph.D. from the University of Chicago. In today’s conversation, we talk about:


Why our political process has become so polarized,

Why it’s near impossible to get reasonable candidates elected, and 

What each party is either right or wrong about.

Most importantly, Charlie lays out some very practical ideas for how we can restore sanity to our governing bodies.


Check out Charlie’s website here.

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About Paul Ollinger and Crazy Money
After working as one of Facebook’s first 250 employees, Paul retired from the corporate world at 42, only to find himself bored, lonely, and driving his wife crazy. Today, he’s a standup comic, captivating audiences with his unique blend of humor and insight, performing alongside a diverse group of comedy powerhouses and iconic musicians, including Norm Macdonald, Dave Attell, Chelsea Handler, Styx, and Collective Soul.
In 2019, Paul started this podcast, Crazy Money to explore the connection between money, happiness, work, and meaning. In one-on-one conversations with some of the world's most interesting people, he helps uncover the true sources of happiness in life and what wealth, success, and fame can (and can't) do for us. Previous guests include LL COOL J, Judd Apatow, Moby, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic gold medals.
Paul is always on tour and coming to a comedy club near you. Check dates here.

This episodes Keywords:
 Taxes, tax policy, inequality, infrastructure, Civics government, elections, voting, Dartmouth, federal debt. Please stop reading and have a great day. Paul loves you.

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 recent TED Talk, '5 Lessons on Happiness – from Pop Fame to Poisonous Snakes,’ he began a 3,000 mile on-foot trek across the United States, starting in New Jersey and making it all the way to Colorado where he was waylaid by a rattlesnake bite. After a few weeks of recovery, he set back out on the road, completing his walk with a run into the Pacific Ocean at Venice Beach, CA. In this joyous conversation, Paul and Mike cover:

Mike's journey from pop star to becoming his own person

Mean things people said about him on social media

What he rapped about when he was 8 years old

Mike’s youthful collaboration with Big Sean 

The duality of human nature and how we all have good and bad within us

Self-awareness and the importance of compassion

Following one's own path, rather than relying on external validation. 

Why we must embrace our mortality, and the reason others want you to forget it

The importance of faith

Check out Mike’s TED Talk: 5 Lessons on Happiness and his Spotify profile.


💰Rate and review Crazy Money here. 💰

🔥 Register for Paul’s incredible newsletter here.🔥

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



About Paul Ollinger and Crazy Money
After working as one of Facebook’s first 250 employees, Paul retired from the corporate world at 42, only to find himself bored, lonely, and driving his wife crazy. Today, he’s a standup comic, captivating audiences with his unique blend of humor and insight, performing alongside a diverse group of comedy powerhouses and iconic musicians, including Daniel Tosh, Dave Attell, Chelsea Handler, Norm Macdonald, Styx, and Collective Soul.
In 2019, Paul started this podcast, Crazy Money to explore the connection between money, happiness, work, and meaning. In one-on-one conversations with some of the world's most interesting people, he helps uncover the true sources of happiness in life and what wealth, success, and fame can (and can't) do for us. Previous guests include LL COOL J, Judd Apatow, Moby, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic gold medals.
Paul is always on tour and coming to a comedy club near you. Check dates here.

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, we talk about how money is the tail that wags the dog and both the GOP and the Democratic Party. He mentions why we should pay our politicians more, how gerrymandering and primaries forment polarization, and we talk about entitlement reform and universal basic income. Even if you don't agree with all his policy ideas, I think you'll agree that Andrew’s efforts to fix the machine of politics are worthwhile and something we should all think about supporting because the current polarized political system is making everybody freaking miserable. Andrew is the son of immigrants from Taiwan. He attended Philips Exeter, Brown University, and Columbia Law School. This episode oraingally ran in August of 2022.

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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. 

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. 

‘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.