Reasonably Happy with Paul Ollinger

If your new college grad son or daughter is unemployed, sleeping in their childhood bedroom, and watching All My Children every day, fear not - Laura Belgray has been there and she turned out okay. As Laura explains in her new, laugh-out-loud (LOL) funny memoir, Tough Titties: On Living Your Best Life When You’re the F-ing Worst, sometimes it’s good to be unoccupied so that, when opportunity finally calls, you are there to answer the phone. The book, which her husband refers to as “Loser Sex in the City,” is a collection of hilarious, unfiltered stories about her life. Equal parts Nora Ephron, Tina Fey, Chuck Klosterman, and David Sedaris, Tough Titties is a celebration of failure, late bloomers, messy career paths, and lessons learned from indiscriminately blowing bartenders in the early 90s. So it’s no wonder that Kelly Ripa said of the book, “I didn’t want it to end!” Though slow out of the gates, Laura eventually found her thing and now celebrates the wonder of being paid for authentic self-expression. In this delightful chat, Laura and I discuss the primal fear of being disliked, how being a loser in 6th grade is related to her later success in adulthood. pre-Giuliani Times Square B.S. social media wellness gurus Mean Girls, Leg warmers Why Deb Fishbone is a shallow, basic bitch Getting paid to watch TV Learn more about Laura on her website.  ⭐ Rate and Review Crazy Money here. (Seriously, do it!)⭐  ✍️ Get Paul’s writing to your Inbox here. (Seriously, do this also!) ✍️ And yes, I said “Titties.” Here, I’m going to say it again: titties. Also, I know that All My Children is no longer on the air. Feel free to substitute: TikTok, Roblox, or PornHub

People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like Angelina Jolie, Kim Kardashian, Johnny Depp, Ryan Reynolds, Dr. Dre, Kevin Costner, Maria Shriver, and Jimmy Iovine, among many others. And while “celebrity divorce attorney” might conjure up images of a rapacious shark in Prada boots squeezing every dollar out of her clients’ exes, Laura preaches the gospel of divorce with dignity. Her book, It Doesn’t Have to Be That Way: How to Divorce Without Destroying Your Family or Bankrupting Yourself is a jungle guide for ending a marriage while preserving decency, values, and a couple’s wealth. As she writes, “…the more acrimony, argument, and angst, the more money your attorney makes. We profit from your inability to resolve issues.” In other words, don’t pay your lawyer $1,000/hr to determine—as famously captured in When Harry Met Sally—who gets the “stupid, wagon wheel, Roy Rogers, garage sale coffee table.” Her book is a plea to all those going through one of the most stressful human experiences possible to summon your best self and think about who you want to be when the dust settles. Laura and I talk about the fundamental language of divorce, including spousal support, child support, no-fault divorce, community property, and also the more philosophical dimensions of the process, like the concept of “fairness” and how one defines “winning.” Sincere thanks to my former Facebook colleague, Matt Jacobson for making the connection to Laura. I appreciate, Jake! Follow Laura on on Instagram and learn more about her practice here.   ✍️Subscribe to Paul’s Substack here ✍️

If you’re trying to hide assets from your spouse or soon to be ex-spouse, beware! Whether it’s Cayman Islands bank accounts, bearer bonds stashed in a safe deposit box, “hidden" real estate, or hundreds-of-thousands in Bitcoin, Nick Himonidis and his team at NGH Group will probably discover your secret stash. Nick is an attorney, Certified Fraud Examiner, and Certified Crypto Currency Forensic Investigator, which is a fancy way of saying that he is a high-end, sophisticated, and technologically-proficient private investigator. He and his team have have uncovered many millions of dollars in undisclosed assets in single cases. In this conversation, Nick offers insights into how he and his colleagues go about their work, why you’ll probably get caught, and why—if you’re going to hire a private investigator—it’s vitally important TO YOU to hire one with a high degree of professional ethics. Learn more about Nick and NGH Group on their website.    ✍️Get Paul’s writing to your Inbox here ✍️ About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

Having experienced divorce as the child of a wealthy family, Olivia Summerhill understands the massive impact parents fighting about money can have on their children’s lives. Today, Olivia provides financial consulting for ultra-high-net worth women going through divorce. Her typical client has a household net worth of $100mm or more, so she provides advice on everything from stocks, bonds, art, planes, country club memberships and cosmetic surgery! As importantly, she helps her clients clarify their values, financial priorities, and to visualize their lives post-divorce. The host of the Divorce for Wealthy Women podcast, Olivia is both a Certified Financial Planner and a Certified Divorce Financial Analyst. In this super-fun and sometimes-scary conversation, we discuss pre-nuptial agreements, shame around money, the concept of “fairness” in a divorce, and a book that she loved and I absolutely did not! She spoke to me from Seattle where it was 5:00 a.m.! (that’s three exclamation points in one episode description! I mean four! No, wait five…). Learn more about Olivia and her services on her company’s website.   ✍️Read Paul’s Substack here ✍️ 🎤 See Paul’s upcoming shows here 🎤 About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

Will Vogt is a photographer with a front row seat to the American upper class. Raised on Philadelphia’s Main Line, Will attended boarding school, and spent lots of time in the tony enclave of Watch Hill, Rhode Island where his family summered. His new collection of photography, These Americans, showcases decades of intimate snapshots of his social circle. Entertainment news site Vulture says the work "depicts the wealthy at leisure with their guard down.” Indeed, Will has captured a very rare, candid and un-self-conscious picture of the American upper class doing their thing, which—in a few cases—is cocaine. In some others it’s weed and/or alcohol. Since the majority of these shots were taken in the 1980s, it is highly appropriate that Jay McInerney (Bright Lights, Big City) composed the introduction. He wrote that Vogt is “documenting the world of the descendants of those whom (F. Scott) Fitzgerald wrote about. And he is clearly a member of this tribe, albeit a self-aware and observant one.”  See Will’s photos / order the book on his website.  🧘Watch Paul’s hilarious meditation videos here🧘  ✍️Read Paul’s brilliant writing here ✍️

Our higher education system is broken. But instead of trying to fix the underlying issues, the Biden administration is attempting to treat the symptoms with a massive giveaway to student loan debtors. In this encore episode (from August, 2022), I speak with Oren Cass. Executive Director of American Compass, whose article The Banality of Student Loans outlines the contradictions and self-defeating policies that have led us to this educational morass.  Ask yourself: • Why is student debt treated differently than all other kinds of debt? • Why are taxpayers on the hook for payments to colleges and universities instead of the institutions themselves? • Why would you forgive hundreds of billions in loans without addressing any of the reasons we got into this mess in the first place? Oren and I discuss the “college for all” approach and why it is the wrong way to prepare the vast majority of young Americans for a career–especially those who need an economic boost the most. We talk about why the federal government should not underwrite student loans and who should. And Paul vents about “these damn young kids - don’t they know what ‘obligation’ means?” Speaking of expensive colleges, Oren graduated Williams College and Harvard Law School, magna cum laude. (Paul graduated from Rhodes College, sine honoribus.)  ✍️Get Paul’s Substack newsletter here.✍️   Follow Oren- Twitter - https://twitter.com/oren_cass Website - https://orencass.com/

If you find marriage to be hard, you are not alone. If you feel as if your spouse should fulfill every single physical, emotional, sexual, and financial need in your life, you probably should be alone. This week, I talk to Eli Finkel, author of the book, The All-or-Nothing Marriage in which he presents data and anecdote about how the best marriages work and what we can learn from them. We discuss the evolution of marriage over the centuries, when and why love became part of the equation, how helping your spouse grow benefits you, the role of money in marriage, and why consensual non-monogamy will 99.999999999% for sure never happen in the Ollinger household. A survey of Eli's peers identified him as the most influential relationship scientist in the 21st century and the Economist declared him “one of the leading lights in the realm of relationship psychology.” On the other hand, his wife thinks it’s hilarious that he is a “marriage expert.” Learn more about Eli and his book here.  ✍️Read Paul’s Substack here ✍️ 🎤 See Paul’s upcoming shows here 🎤 About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

Turney Duff was making millions on Wall Street until cocaine addiction brought him to his knees. His book The Buy Side: A Wall Street Trader’s Tale of Spectacular Excess is a funny, horrifying, then hopeful read and a New York Times best-seller (you should buy it here). Paul and the esteemed author share a lot of laughs as they discuss what money meant to Turney as he got rich, got lost, got sober, then got published. This darn funny conversation covers everything Turney's middle school science fair fiasco to insider trading. Also, prostitutes. Find out more about Turney and hear the Galleon rap here.  🔥 Follow Turney on Twitter 🔥   ✍️Read Paul’s Substack here ✍️ 🎤 See Paul’s upcoming shows here 🎤 About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

For your summer listening while driving, walking, gardening, pleasure, Paul reads three of his latest pieces from Substack (Money and the Meaning of Life), including: How to Stay Hungry When Your Life is Full Money, Pain, and New Cars You Deserve It, i.e. reflections on what it means to “deserve” something Paul publishes these essays (about) every other Tuesday.You should subscribe here. 🔥 Please feel no pressure to pay for a subscription, but do feel pressure to share his writing and this podcast with ALL of your friends. Also, you can also see where Paul (i.e. me) will be performing comedy here. 🎤 Shows coming up in Chattanooga, Charlotte, and Atlanta. About Paul: Paul Ollinger spent 15 years in sales leadership positions for Yahoo! and Facebook before bailing on the world of digital advertising to chase his comedy dream. He has headlined Carolines on Broadway, performed at legendary clubs such as the Hollywood Improv and the Comedy Cellar, and opened for everyone from Bill Burr to classic rock bands, Styx and Collective Soul. He plays comedy clubs, country clubs, and dirty bars all over the country. A graduate of Rhodes College, Paul earned his MBA at Dartmouth’s Tuck School. He lives in Atlanta with his wife, two tween kids, and French bulldog, Colonel Tom Parker. Follow him on Facebook.  About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?

Bruce Feiler is a seven-time New York Times best-selling author of books such as Life is in the Transitions, Walking the Bible, and The Council of Dads, Bruce's 2008 account of his battle with bone cancer and the contemplation that his then three-year-old twin daughters would grow up without a father. The book birthed a documentary hosted by Sanjay Gupta, a drama series on NBC, and a wildly popular TED Talk. In his new book, The Search: Finding Meaningful Work in a Post Career World, Bruce argues that the truths about work with which so many of us Boomers / GenX’ers were raised no longer apply and that today’s economy is “meaning based” as opposed to “means based.” We discuss what implications this has for employers, workers, and those of us trying to understand just what is going on out there. We talk about why Bruce dedicated the book to Pat Conroy, why that means something to Paul, how our expectations of a linear world and career stress us out and why it is critically important to “stop chasing someone else’s dream (or, in Paul’s case the approval of Sheryl Sandberg). Special thanks to 2x Crazy Money guest and occasional listener, A.J. Jacobs for connecting me with Bruce. 🔥 Visit Bruce’s website here. 🔥  👀 Read Bruce’s Substack, The Nonlinear Life here. 👀 🔥 Read Paul’s Substack here. 🔥 🎤 See Paul’s upcoming shows here. 🎤 About Crazy Money: Unlike traditional personal finance or investing 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 cable providers. It is about deciding what role we want money to play in our lives and how we can use it to achieve our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-Life Crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, and status. Crazy Money is edited by Mike Carano. Are you really still reading?