Crazy Money with Paul Ollinger Paul Ollinger

Nicole Avant is the former U.S. Ambassador to the Bahamas and author of a new memoir, 'Think You’ll Be Happy: Moving through Grief with Grit, Grace, and Gratitude’ which tells the story of her extraordinary family and her mother’s tragic death by murder. Her mom, Jacquie was a philanthropist and community activist whose example taught Nicole kindness, respect, and humility. Nicole’s father was Clarence Avant, a highly successful music executive who gathered in their Beverly Hills home a mélange* of the most prominent musicians, producers, actors, and politicians. Indicative of the environment in which she grew up, Nicole’s godfather is legendary producer, Quincy Jones. Speaking of godfathers, Nicole produced a documentary about her dad called 'The Black Godfather,’ which is available on Netflix and is totally amazing. After college, Nicole worked in the music business but got into politics, eventually becoming the Southern California finance co-chair for the 2008 Presidential campaign of Barack Obama who appointed her Ambassador. Nicole’s film about the contributions of Black servicewomen during WWII, 'The Six Triple Eight,’ was directed by Tyler Perry and comes out later this year. Check out The Black Godfather trailer here and learn more about Nicole’s book here. (So you understand the context, the “Ted” to which Nicole refers in this interview is her husband, Ted Sarandos, Co-CEO of Netflix.)

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*I said it - mélange, baby!

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.

On this introspective episode of Crazy Money, Paul sits alone in his empty Atlanta house and talks openly about the thoughts and feelings that drew him back to Atlanta, and the head trauma that may or may not have initiated his desire to sell everything and move to New York City.
Oh, by the way, my name is Mike Carano and I’m writing these surely-to-be-deleted episode notes. Paul is occupied with the chaos of moving, but I suspect he’s more likely trying to get to the bottom of the, “which Ray’s Pizza is the REAL Ray’s Pizza.” In between mumbling, “miles to go before I sleep,” he asked if I could handle this writing task. Inspired by he and Stacey’s decision to embrace a big change and wring every drop out of this thing called life, I said uhh, okay. 
In this intimate podcast Paul talks about how this move came about, how he, Stacey, and their two kids, kid #1, and kid #2, ended up in Atlanta, and his plan to put the pedal to the metal and maximize opportunity, expand horizons, and have coffee with the dude from TED.
I found this be be genuinely inspiring, and I’ve decided to do the same thing. Only I’m going to Barstow, because I’m broke.
Please enjoy this thoughtful episode.


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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. 

Yes, there was actually a guy named Rudolf Diesel who actually invented the diesel engine, which was incredibly revolutionary for its time. It earned Diesel a massive fortune and had huge implications for how war—especially maritime war in the early 1900’s—would be waged. As European countries scrambled for dominance just prior to WWI, Diesel disappeared, leading to speculation that he was murdered by either Germany’s Kaiser Wilhelm II or by America’s John D. Rockefeller whose young petroleum empire Diesel's motor threatened. Or maybe Diesel leapt to his own death. Or maybe...something else happened. Author Doug Brunt’s new book 'The Mysterious Case of Rudolf Diesel: Genius, Power, and Deception on the Eve of World War I’ tells the story of this incredible innovator and the impact his machine continues to have on the world. Doug Brunt grew up in Philadelphia and graduated from Duke University. A former technology executive turned writer, his previous novels include 'Ghosts of Manhattan’ (which is f-in great!), 'The Means’, and 'Trophy Son'. He lives with his wife, journalist Megyn Kelly, in Connecticut. Check out Doug’s website here. 💰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 MoneyAfter 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.

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.

💰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 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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