Crazy Money with Paul Ollinger

What did Ray Kroc, Maya Angelou, Margaret Thatcher, and Malcolm X all have in common? (Don’t worry - this isn’t a dirty joke!) They were all opsimaths, i.e. a person who blooms late in life. In his new book SECOND ACT: What Late Bloomers Can Tell You About Success and Reinventing Your Life, author Henry Oliver shares the stories of well-known people whose greatest accomplishments happened in or past middle age. In other words, there’s still hope for you! Maybe you’re 45 and haven’t written the great American Novel yet. There’s still time! You’re 55 and haven’t made your first million or billion? There’s still time! You’re 65 and havne’t gotten elected to political office? Well, let’s not push it, but you never know. If you are indeed an opsimath, you’ll keep working toward your goal for the sake of the thing and not in hope of any extrinsic rewards. In this informative and sometimes humorous conversation, Henry and I—two urbane gentleman that we are—discuss the following:

Pre-order Henry's book here. Subscribe to his Substack here. 

WAIT - don’t go until you’ve done 2 out of these 3 things:

💰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:

late bloomers, success, age, intelligence, motivation, hard work, meandering path, passion, experience, network, late bloomers, success, reinventing life, Ray Kroc, McDonald's, Katharine Graham, Washington Post, David Duffield, Workday, internal motivation, careers, second careers, reinvention

Nobody gets into poetry for fame and fortune. And yet, there might be a tiny bit of each happening for In-Q, my guest this week who is a renowned poet and spoken word artist. When he started freestyling (aka, “rapping" for you old people) with his friends at age 13, In-Q felt an empowerment that didn’t exist in the rest of his life. The words inside him took on a life of their own and, after he started writing poetry at 19, In-Q found himself in the embrace of L.A.’s slam poetry community. He never really considered poetry taking him to a place where could make a living, "let alone live in abundance.” But through dedication, perseverance, and perhaps, the sheer inability to quit, he’s now selling out theaters, writing hit songs, and publishing books and albums. In-Q has appeared on A&E, ESPN, and HBO’s Def Poetry Jam. His stand-up poetry special, 'Live at the Ace Theatre', is now streaming exclusively on Amazon Prime Video. To top all that, Oprah (you know “Winfrey”) named him to her SuperSoul 100 list of the world’s most influential thought leaders.

On this week’s episode, In-Q and I discuss:

Watch his special, Live At the Ace Theater and listen to his album The Never Ending Now

WAIT - don’t go until you’ve done 2 out of these 3 things:

💰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:

IN-Q, poet, spoken word, slam poetry, creativity, self-expression, learning disabilities, dyslexia, art, IN-Q, poetry, creativity, writing process, empowerment, tattoos, Amazon special, immersive experience, album, book, events, forgiveness

Paul loves you. 

The spirit of the working class is crushed. So argues Batya Ungar-Sargon in her new book 'Second Class: How the Elites Betrayed America's Working Men and Women’. Batya says that working men and women in the United States have been abandoned by both political parties and left to fend for themselves all while unchecked immigration makes an already challenging job market untenable. As her title suggests, she believes “elites” are causing this problem. And though you hear the word used more often and somewhat scornfully on Fox News, “elites”  doesn’t just progressives. It’s alll of us who are educated, have stable jobs, and aren’t worried aobut making rent next month. But just because Batya uses the word doesn't mean her main argument—that unchecked immigration is making life untenable for working Americans—is wrong. At the very least, it is inarguable that immigration is putting a strain on our housing, educational and medical infrastructure. And all of us foot the bill for that. What’s really odd about this to me is, despite the fact that Batya defends Donald Trump as a friend of the working people, that the policies she recommends to fix the problem feel like Democratic policies from an earlier time. Unions, tarriffs - that sort of thing. Whichever side they’re from, she is passionate about the importance of a thriving middle class for a stable democracy. Batya is The Opinion Editor at Newsweek. She holds a BA from the University of Chicago and earned her PhD at UC, Berkeley. Her writing has appeared in The Washington Post, Los Angeles Times, Foreign Policy, the New York Times, The Daily Beast, and The Free Press. Buy ’Second Class’ here.

WAIT - don’t go until you’ve done 2 out of these 3 things:

💰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:

elites, working class, income inequality, immigration, Trump, unions, working conditions, middle class, stable democracy, vice president, politics, kamalaharris, election, timwalz, joshshapiro

Paul loves you. 

**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:

💰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:

News, good news, bad news, negative filtering, evolution, negative news, perception, progress, media, incentives, bias, optimism, technology, AI, biotechnology

Paul loves you.

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.

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.

This episodes Keywords:

Family, business, careers, succession, gas stations, convenience store, pecans, stuckeys, Buc-ees, C-store

Paul loves you.

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.

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:

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 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:

Rudolf Diesel, boats, engines, Writing, author, novelist, Technology, Innovation, Diesel, Rockefeller, Doug Brunt, Megyn Kelly, transportation, oil industry, history, sea, invention, diesel power, invention, innovation, inventors, entrepreneurship, military, international politics, technology, war. 

Paul loves you.