
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

Aug 7, 2024 • 39min
Why the News is Bad with Angus Hervey
**Hi friends - this is Paul writing to confess to an error in my introduction in this week's episode. The name of Angus Hervey's podcast is "Hope Is a Verb," not—as I called it—"Hope is NOT a Verb," which is kind of the opposite (insert winky emoticon). Unfortunately, I am unable to re-record the intro as we are traveling, but I can change these show notes, so that's what I'm doing. Sincere apologies to my most gracious guest for this ridiculous foul-up.**
The news is always bad, and that’s not an accident. “If it bleeds, it leads” has long been the theme that drives networks and newspapers to accentuate the negative because that’s how you earn ratings and pageviews, baby! This week, Dr. Angus Hervey, founder of 'Fix the News’ and the co-host of the podcast ‘Hope Is A Verb’ joins Paul to discuss the evolutionary and economic reasons behind this phenomenon and how it hurts us as a society. The dreadful headlines disguise the truth that we humans are making terrific progress fighting poverty, eradicating disease, finding alternatives to fossil fuels, and expanding human rights. But you wouldn’t know that reading the New York Times or scrolling your Facebook feed. Of course everything isn’t perfect. But thanks to technology and perhaps to the fact that—as Dr. King said—the arch of the moral universe bends toward justice, things are way better than they have ever been and they continue to improve. We ignore this to our peril and at the cost of our happiness. As Dr. Hervey cautions negative news is an addictive product that divides us as a society, "breeding cynicism, apathy, hopelessness, and even hate.” As if that weren’t bad enough, it also prevents us in believing that progress can be made, saying “If we want more people to devote themselves to making progress, maybe we should tell more people that it’s possible to make progress.” Further, he says that all these predictions of an AI apocalypse are highly-overblown. Angus earned his PhD in Political Econmomy at London School of Economics. His two TED Talks have generated millions of video views,
He lives in Melbourne, Victoria, Australia whence he spoke to Paul before his children woke up. Listen to Hope Is A Verb and read Fix The News today!
WAIT - don’t go until you’ve done 2 out of these 3 things:
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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:
News, good news, bad news, negative filtering, evolution, negative news, perception, progress, media, incentives, bias, optimism, technology, AI, biotechnology
Paul loves you.

Aug 4, 2024 • 49min
Fighting for the Family Business with Stephanie Stuckey
Stephanie Stuckey used her life’s savings to buy the company that is her family’s legacy. At it’s height in the1960’s and 70’s, there were hundreds of Stuckey’s stores selling gas, pecan candy, cold drinks, and quick meals near highway exits around the United States. But after her grandfather was bought out by a big corporation, the neglected enterprise and its stores fell into disrepair. Since buying what remained of the company five years ago, Stephanie—an attorney and former Georgia State Representative with no prior business experience—has been on a mission to restore the brand to its former glory. She relishes Stuckey’s history and philosophy of hospitality that welcomed *all* travelers during an era when segregation was the rule. Her inspiring story is that hopeless romantic who puts it all on the line to celebrate what’s good and authentic in the world. Stephanie lives in Atlanta. She loves sweet tea, R.E.M., and the Georgia Bulldogs. Follow Stephanie on Instagram and LinkedIn and getcha some Pecan Log Rolls on the Stuckey’s website. Oh, and buy her book here.
💰Rate and review Crazy Money here. 💰
🔥 Register for Paul’s incredible Substack 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.

Jul 24, 2024 • 57min
Persevering Through Grief with Nicole Avant
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.)
💰Rate and review Crazy Money here. 💰
🔥 Register for Paul’s incredible newsletter here.🔥
🎤 See Paul LIVE for telling of comedy jokes here. 🎤
*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.

Jul 3, 2024 • 34min
On The Move
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.
HEY - want to help Paul grow this great podcast? DO THESE THINGS:
💰Rate and review Crazy Money 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: 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.

Jun 12, 2024 • 48min
Who killed Rudolf Diesel? (with Doug Brunt)
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.

Jun 4, 2024 • 1h 3min
Restoring Politcal Sanity with Charlie Wheelan (Encore)
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.

May 28, 2024 • 46min
Mike Posner on Life Beyond Fame and Fortune
Grammy-nominated artist Mike Posner shares his journey from fame to seeking purpose, including his 3,000-mile walk across the US. Topics include self-awareness, embracing mortality, faith, and the importance of following one's own path.

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.
💰Rate and review Crazy Money here. 💰
🔥 Register for Paul’s incredible 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: 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
HEY - want to help Paul grow this great podcast? DO THESE THINGS:
💰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: 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.