Reasonably Happy with Paul Ollinger

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. 💰 🔥 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. 

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.

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.

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.

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. 

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. 

‘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. 

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 raising stable kids in an atmosphere of affluence. Debbi tells the story of how she went from Oakland A’s ball girl to cookie kingpin and her commitment to quality over cost control. She also tells us how she kept a positive attitude when circumstances compelled her to give up control of the company. Wade emphasizes the importance of motivation, positive attitude, and controlling one's thoughts in achieving success. Both discuss their commitment to friendship. Learn more about ThirdHome 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: entrepreneurship, customer experience, real estate, motivation, positive attitude, friendships, family, friendship. Please stop reading and have a great day. Paul loves you. 

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 conscience he experienced when counseling a temple member who had ALS about her assisted suicide. Finally, Rabbi Leder speaks frankly about what Israel means to him and the tragic complexity of the war between Israel and Hamas. Follow Rabbi Leder on Instagram here.  • 💰Rate and review Crazy Money here. 💰 • 🔥Register for Paul’s thought-provoking newsletter 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: regret, joy, sadness, forgiveness, fundraising, preaching, teaching, relationships, advice, conscience, ALS, end-of-life decisions, euthanasia, Jewish law, compassion, Israel, Middle East, Gaza, Hamas. Please stop reading and have a great day. Paul loves you.