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Crazy Money with Paul Ollinger
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Crazy Money with Paul Ollinger

Author: Paul Ollinger

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Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).

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Sam Dogen left his job in investment banking at age 34 to start his financial newsletter, Financial Samurai. He's got a new book out this week called “Buy This, Not That!” How to spend your way to Wealth and Freedom. Today Sam and I discuss his one word definition of 'Happiness', how wearing the right tie helped him get a job at Goldman Sachs, how he transitioned out of investment banking to become an independent financial writer, how the right plan is the key to surviving inflation and the ups & downs of the stock market, and why he advises young adults to forecast their professional misery. We also discuss his best and worst financial investments and among other things, the return on investment of private vs public school.  If you enjoy Crazy Money, please leave us a rating here.  Follow Paul’s Substack newsletter here. Subscribe to the Crazy Money YouTube channel here. Follow Sam- Twitter - https://twitter.com/financialsamurai  Website - https://www.financialsamurai.com/ Link to book - Buy This, Not That! https://www.financialsamurai.com/btnt/
Today’s guest is Vitaliy Katsenelson. He's an investor, writer and author of the new book ‘Soul in the Game : The Art of a Meaningful Life’. Nassim Nicholas Taleb, the author of The Black Swan calls the book deep, insightful, inquisitive and civilized, which is a pretty good description of Vitaliy himself.  In this episode we discuss what it was like growing up in Russia, north of the Arctic Circle, how America did and did not fit with his expectations, which were set by all the American movies he had seen before he arrived at age 18. Whether rich people are actually happier, what we can learn about careers in comparison from Franz Schubert and Beethoven, what it means to be a student of life, and what may or may not happen in Ukraine. We recorded this conversation in June (2022). This is coming out in July, so I can't say what has or hasn't happened in the meantime. Just so you know.  💰 If you enjoy Crazy Money, please leave us a rating here. 💰 🔥 Get Paul’s Substack newsletter here.🔥 🔥 Subscribe to us on YouTube here. 🔥 Follow Vitaliy Twitter - https://twitter.com/vitaliyk Website - https://contrarianedge.com/ Link to book - ‘Soul in the Game : The Art of a Meaningful Life’
This is an encore episode with Rich Beem, winner of the 2002 PGA Championship, one of professional golf’s four major tournaments. Despite having won twice on tour prior to the PGA, Rich's win at Hazeltine was as unlikely as the groovy dance moves he busted out after sinking his final putt of the tournament. Describing himself as “the luckiest guy in the world,” Rich played the game loose and wide open, but the rising expectations of being a major champion became a distraction, and he never won again on tour. In this chat, Rich speaks candidly about: Selling car stereos and grinding his way up the golf ladder, Finding purpose and meaning in life as his PGA prospects began to dim.  The reason he tells his son that “what you shoot is not you” Why he loves working as an analyst at Sky Sports Rich was born in Phoenix, AZ, grew up in El Paso, TX and played college golf at New Mexico State University. Today Rich plays on the PGA Champions Tour and works as a TV golf analyst on Sky Sports in the UK and Ireland.(Originally posted November, 2020. Follow Rich on Twitter.   💰If you enjoy Crazy Money, please leave us a rating here. 💰 💪Follow Paul on Instagram here. 💪 🔥Get Paul’s newsletter here.🔥
Jay Newman makes BIG bets. In his 40 year hedge fund career, Jay was the guy who fought to recover deca-billion dollar debt defaults by countries like the Congo, Panama, and Argentina. Recouping from these deadbeat governments required long term thinking, stealthy patience, and giant cojones, the same attributes required to publish a debut novel, which Jay did earlier this year. The New Yorker called his new book, Undermoney a combination of “espionage, financial intrigue, and geopolitics with a cynicism developed through years of observing politicians and Wall Street titans up close.” And because the plot lines include Russian oligarchs, private militias, and Vladimir Putin, Undermoney is also “unexpectedly timely.” I’ve read it: it’s juicy and enticing. Learn more about Jay here.  💰If you enjoy Crazy Money, please leave us a rating here. 💰 💪Follow Paul on Instagram here. 💪 🔥Get Paul’s newsletter here.🔥
A.J. Jacobs believes that puzzles can save the world. The famously obscure 4-time New York Times best-selling author of books like The Know-It-All, Thanks a Thousand, and The Year of Living Biblically tells us what we can learn from them in his new book The Puzzler: One Man’s Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life. We talked about some great life lessons A.J. gleaned from puzzles, including: Start with the end in mind Embrace the eraser (i.e. your first impression might not be accurate!), and most importantly, PAY ATTENTION, KNUCKLEHEAD!  Join other readers in the quest to win A.J.’s $10,000 by clicking here.  🔥Join Team Ollinger here.🔥 💰Rate and Review Crazy Money here. 💰 💪Follow Paul on Instagram here. 💪
Description: Christian Finnegan is a comedian and actor, well known for his work on Chappelle’s Show and the popular sitcom, Are We There Yet? He has performed on Comedy Central Presents, Conan, The Late, Late Show with James Corden, and his five comedy specials are in regular rotation on all major streaming services. An avid music fan, Christian wants to connect formerly-cool middle aged people to the best in new music. Check out his Substack, New Music for Olds here.  🔥Join Team Ollinger here.🔥 💪🏼 Rate and Review Crazy Money here. 💪🏼  🦸‍♂️ Follow Paul on Instagram here. 🦸‍♂️
Description: Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of Boston College’s Center on Wealth and Philanthropy, Paul is the co-author of The Joys and Dilemmas of Wealth, a 2010 report that is one of the most insightful studies of the ultra-affluent ever. We discuss how the fears and joys that come with being rich are often two sides of the same coin. And how Paul, a former Jesuit priest strongly influenced by Karl Marx, has come to appreciate more fully the humanity of the upper class. Learn more about Paul Schervish here.  💪🏼 Rate and Review Crazy Money here. 💪🏼  🦸‍♂️ Follow Paul on Instagram here. 🦸‍♂️
Something happens to many of us in our 40’s or 50’s: having achieved a certain level of success, we yearn to find work that is an expression of who we are. Chip Conley can help with that. He founded and runs Modern Elder Academy, a school and retreat center dedicated to helping people navigate midlife and beyond. To do so, he draws on insights and wisdom earned over his own incredible career journey. For over two decades, Chip ran Joie de Vivre, the boutique hotel owner/operator that he founded in his 20s. In the depths of the Great Recession, the combination of medical crisis and market turmoil compelled Chip to sell out at the bottom of the market. While many might have given up, Chip forged ahead, reinvented and redefined who he was, all the while staying open to where that journey would take him. It eventually took him to Air BnB where become the in-house consigliere (among other things) for Air BnB CEO/co-founder Brian Chesky. Today, Chip writes, speaks, surfs, and provides the space and resources to help other “successful” people examine their lives and commit to positive paths forward.  Learn more about Modern Elder Academy hereand Chip’s newsletter here.  • 💪🏼 Rate and Review Crazy Money by clicking HERE.💪🏼 • 🦸‍♀️ Follow Paul on Instagram HERE🦸‍♂️  Topics covered in this episode: #purpose #wellness #community #travel #hotels #Airbnb
41% of people who make over $200k per year still cry about money. That’s the finding of a recent study that Paul discusses this week with Joe Saul-Sehy, Creator and co-host of the Stacking Benjamins podcast AND author of Stacked: Your Super-Serious Guide to Modern Money Management. These two handsome bald fellas also chat about: The double life Joe was living as a young financial planner How he hit bottom when his car ran out of gas What you want in—and how much you should pay for—wealth management Whether or not you should manage your own money If you want to give Paul a birthday present, Rate and Review Crazy Money! And/or Follow Paul on Instagram. Order Joe’s book here. You’re the best. Really. I swear. (I mean, Paul swears.)
Jacob Goldstein is the author of Money: The True Story of a Made Up Thing and former co-host of Planet Moneywhere he worked for over a decade. His new podcast, What’s Your Problem? from Pushkin Industries explores how company founders solve consumers’ problems and what problems they themselves run into along the way. On today’s show, we tackle the following: The question that Ira Glass described as “the most stoner question ever”  How cash transactions worked in these United States before we had dollar dollar billz, y'all Why you making more money doesn’t mean someone else will make less How working at Pushkin is different than working at NPR and the Wall Street Journal The name of the very first compact disc he ever bought. Jacob is a former staff writer at the Wall Street Journal, the Miami Herald, and Bozeman Daily Chronicle. His work has appeared on This American Life, Morning Edition, and in the New York Times Magazine. He is a husband and father of two. He spoke with me from his soundproof closet in Brooklyn, USA. Check out What’s Your Problem?here.  ⭐ Get 15% off your SideCar carrier with promo code CRAZYMONEY by clicking HERE.⭐ 💪🏼 Rate and Review Crazy Money by clicking HERE.💪🏼  🦸‍♀️ Follow Paul on Instagram HERE 🦸‍♂️
If you think Paul Ollinger can’t draw poignant and funny lessons about money from the 1996 box office smash, Jerry Maguire, you are sadly mistaken. On this week’s very special spring break episode of Crazy Money, Paul reads a couple of his recent reflections on comparison and the delusions we all cling to about the power of wealth. Spoiler alert: money—past a certain point—will not complete you. And comparing yourself to your friends (or enemies) will make you miserable. Full stop. Here’s what we’ll be talking bout today: Stop Keeping Score: How to Quit Measuring Success by Net Worth, Fancy Titles, or TikTok Views Money Isn’t What You’re Missing: What I’ve learned after years of studying money and happiness  You should share this episode with all your friends. And then do 2 out of the following 3 things... Subscribe to Paul’s Medium Posts  Follow Paul on Instagram Rate and Review Crazy Money
Many people want you to believe that the world is in worse shape than ever. They assert that wages are stagnant, inequality is growing and the earth is heating up. But for the vast majority of humanity, things have never been better. Racism, sexism, and homophobia are at their lowest rates in history. We have more and better food than kings and queens could have dreamt of in the 18th century. We have access to clean water, indoor plumbing, effective healthcare, and technology that even billionaires couldn’t have gotten just 20 years ago (the technology, not the plumbing). So why the hell is everyone so freaked out all the time about the decline of civilization? In his new book Comparonomics, Grant Ryan shares a very simple tool to evaluate how the most important aspects of our lives have changed over the past 50 and 250 years, respectively. He also explores our innate biases that lead us to both respond to bad news and spread it around like the virus it is.  Grant spoke to me from his home in New Zealand.  Learn more about Comparonomicshere. YOU really should rate and review Crazy Money here.  YOU should also follow Paul on Instagram. He’s funny.
Judd Apatow doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, developing talent, and getting his family together for dinner. In this week’s episode, the writer / director / producer behind iconic comedy films such as Anchorman, This is 40, and The 40-Year-Old Virgin and I talk about: Why Adam Sandler paid $50 more in rent than Judd when they were roommates How failure prepared him to handle success Being creative during a pandemic Judd has accomplished so much in his career that, in retrospect, his success appears to have been pre-ordained. Despite his massive success in the past 20 years, he never forgets his early struggles and approaches every new project not knowing how it will be received. Having used Quarantine to crank out a George Carlin documentary, a new feature film (The Bubble), and a book, all his fans have lots new material to enjoy over the next few months. I am 364 pages into his new book (Sicker in the Head), and it’s fantastic. You should pre-order it here.  RATE AND REVIEW Crazy Money here. Follow Paul on Instagram here. Have a wonderful day wherever you are. That is all.
Sara Gay Forden is the author ofHouse of Gucci: A Sensational Story of Murder, Madness, Glamour, and Greed,on which director Ridley Scott based his star-studded film.The Economist named House of Guccione of its best books of the year, adding that it reads “like a novel,” which it totally does. The book is much more comprehensive story about the Gucci legacy than the movie, but both culminate in the murder of Maurizio Gucci, former Gucci CEO and grandson of Guccio Gucci, founder of the iconic fashion house. On March 27, 1995, a hit man gunned Maurizio down in the foyer of his 4-story Renaissance-style office and apartment building. His ex-wife, Patrizia, had hired the gunman because Maurizio’s impending marriage meant Patrizia’s alimony would be cut in half.As the sub-title suggests, the Gucci saga is a morality play about the sad by-products of wealth, fame, and status. Not only does being rich and famous not make you happy, but sometimes, it can get you killed. A business journalist with a knack for digging out compelling stories, Sara covered Milan's fashion industry, landing stories about family-owned designer labels like Armani, Versace, and Prada in the Wall Street Journal, Women’s Wear Daily, W, and Bloomberg News. She spent years researching and writing HoG, which came out 20 years ago and finally made its way to celluloid (okay, digital) in November, 2021. Today, Sara leads Bloomberg's reporting efforts on corporate influence and the scrutiny of major tech brands like Amazon, Apple, Facebook, and Google. Learn more about Sara on her website.  Please take a second to rate and review Crazy Money here.  Follow Paul on Instragram.
Julie Lythcott-Haims is passionate about raising self-sufficient kids and helping them find their unique path into adulthood. The former Dean of Freshman at Stanford University, Julie is the author of several books including How To Raise An Adult and Your Turn: How to Be an Adult, both of which we discuss today. In this amazing, smart, and no B.S. conversation, Julie and I discuss: What success means and how we can model it for our children Why affluent parents are more likely to over-parent. Why parents freak out about our kids’ college decisions What Rudolph the Red-Nosed Reindeer can teach us about career plans Julie holds degrees from Stanford, Harvard Law School, and holds and California College for the Arts. She serves on several boards, including LeanIn.org, Common Sense Media, and Parents magazine. She has appeared on NPR, Good Morning America, Today, and mega podcasts like the Rich Roll show. Her TED Talk has been viewed over 6 million times. In other words, she’s, like, super-smart and totally interesting. You should totally listen to our discussion.  Learn more about Julie on her website: https://www.julielythcotthaims.com/ Buy tickets to Paul’s Los Angeles show here.  Rate and review Crazy Money here.  Follow Paul on Instagram here.
When it comes to money, there are two approaches: love or fear.” That’s what Ken Honda writes in his latest work, Happy Money: The Japanese Art of Making Peace with your Money. Ken’s books on money have sold over 8 million copies worldwide. On today’s show, we talk about how we can: Feel worthy of money Say Arigato (thank you) to money  How to make money work in your marriage Make peace with our childhood money experiences  Ken was 29 when he first “retired” to welcome his newborn daughter in the world. He had owned a consultant and accounting business, so successful it had allowed him to close up shop and spend his days with the apple of his eye. Little did he realize his “second” career, impacting millions by helping them heal their relationship with money, was about to begin. That essay was the start of what would become Happy Money, the book we discuss today.   Learn more about Ken on his website: https://kenhonda.com/ Buy tickets to Paul’s upcoming show in Los Angeles here.  Rate and review Crazy Money here.  Follow Paul on Instagram here.
Overthinking is so deeply ingrained in humanity that it shows up as a theme in Buddhism, Stoicism, Shakespeare, and the songs of Barenaked Ladies. Jon Acuff joins us today to discuss his book, Soundtracks, The Surprising Solution To Overthinking. Jon is a New York Times bestselling author of seven books whom Inc. included on their list of Top 100 Leadership Speakers. His writing has been translated into more than a dozen languages and has appeared in Reader’s Digest, Fast Company, The Harvard Business Review andTime Magazine. In this lively conversation, Jon and I discuss:  90’s power pop (the music of Counting Crows, Fastball, Marcy Playground ) Parenting teens and how to help our kids with their negative soundtracks How to (or not to) start a new career Performing as the opening act for Dolly Parton  Listen to Jon’s podcast All It Takes is a Goal and learn more about him on his website. **Rate and review Crazy Money HERE.** Email Paul by clicking here.
Comedian Rocky Dale Davis grew in a trailer park in Brookwood, Alabama. His single mom worked hard to keep him fed and on the straight-and-narrow. After eight years doing comedy, Rocky is headlining all over the country and experiencing his first taste of financial success. So it’s that much more fun to watch me cringe as Rocky tells me that he tries to get rid of money as soon as it comes in and that he doesn’t have health insurance. Rocky has appeared on This week at the Comedy Cellar and Kevin Hart Presents on Comedy Central, NBC  In addition to all this, Rocky and I discuss:  His "abusive, White trash dad" Why he went to Mexico to get his teeth fixed. Getting into fights at church  Get you some more Rock here and here.   **Please rate and review Crazy Money here.** Email Paul here  About Crazy Money: Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Money is not about how to make a million bucks, how to beat the 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 be our best selves. Topics covered include: Philosophy, Happiness, Contentment, Meaning, dreams, purpose, Success, Rat Race, Society, 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. Status. Iranian immigrant, Persian immigrant. Iran. Immigration Edited by Mike Carano Did you already rate and review Crazy Money? Yes? Okay, you can go now...
Today we are going to talk about public mistakes: big, flagrant, public mistakes that might best be described as “failure” and earn the derision of the press and cost your family hundreds of millions of dollars.  Warwick Fairfax was the heir apparent to run John Fairfax, Ltd, an Australian newspaper and media conglomerate that ownedThe Sidney Morning Herald,The Agein Melbourne, and The Australian Financial Reviewand other valuable properties. In 1987, with corporate raiders lurking, Warwick took on massive leverage and launched a $2.25Billion bid to take control of the 150-year old company that had been founded by his great-great grandfather. Three years later, under Warwick’s leadership and due largely to the weight of the debt he sanctioned, the company went into receivership, bringing to an end his family’s media dynasty. In Warwick’s new book,Crucible Leadershiphe shares insights into the opulence of his youth, the pressure he felt to work in the family business, the lessons he learned when he botched things up, and — most importantly— how he survived and forgave himself.  Read more about Warwick and Crucible Leadership here.   **Please rate and review Crazy Money here.** Email Paul here  About Crazy Money: Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Money is not about how to make a million bucks, how to beat the 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 be our best selves. Topics covered include: Philosophy, Happiness, Contentment, Meaning, dreams, purpose, Success, Rat Race, Society, 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. Status. Iranian immigrant, Persian immigrant. Iran. Immigration Edited by Mike Carano Did you already rate and review Crazy Money? Yes? Okay, you can go now...
Ali Partovi is an Iranian-Americanentrepreneur and angel investor. He is best known as a co-founder of Code .org, iLike, and LinkExchange. He was an early investor in Airbnb, Dropbox, Facebook, and Uber. Ali grew up in Tehran during the Iran-Iraq war, attended Harvard, and sold his first startup, LinkExchange, in 1998. On this episode, Ali and I discuss: The GIANT MISTAKE he made in a meeting with Steve Jobs The not-quite as terrible mistake he made when meeting with Jerry Yang of Yahoo! The challenges of building a business on the Facebook platform How being an immigrant shaped his career and worldview. Ali is currently the CEO of Neo, a mentorship community and venture fund he established in 2017. Learn more about Ali and Neo here.   **Please rate and review Crazy Money here.** Email Paul here  About Crazy Money: Unlike traditional personal finance shows like Dave Ramsey or Suze Orman, Crazy Money is not about how to make a million bucks, how to beat the 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 be our best selves. Topics covered include: Philosophy, Happiness, Contentment, Meaning, dreams, purpose, Success, Rat Race, Society, 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. Status. Iranian immigrant, Persian immigrant. Iran. Immigration Edited by Mike Carano Did you already rate and review Crazy Money? Yes? Okay, you can go now...
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