Crazy Money With Paul Ollinger

Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience through “the fascinating world of democracy, politics, and history.” In the process, she is proving that Americans—and other good people around the globe—are hungry for unbiased political context and analysis. "With a heart for education and a mission to clear up political confusion,” Sharon has become known as America’s Government Teacher. And she’s such a clear and compelling teacher that over a million people subscribe to see her reels and stories that offer in-depth and unbiased background to the most important politics issues of the day. Sharon leverages her passion for history and government to promote knowledge, understanding, and TRUTH. Her work is strengthening democracy during a time when it is most urgently need. For that, Crazy Money salutes her! In today’s episode, Paul and Sharon discuss: The increasing politicization of the American cl

Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his gift for mathematics landed him a spot at London School of Economics (alma mater of Mick Jagger, Margaret Thatcher, and George Soros) where he attended with the sons and daughters of the global elite. His skill at a card game won him a job on Citibank’s trading desk and he went on to earn multi-million dollar—er, pound sterling—bonuses in his early 20s. Gary eventually become Citi’s top trader but the game started to take a physical toll on him. The stress, pressure, and moral conflict of betting against poor people—at least that’s how he saw it—led him to leave trading and begin to address growing income inequality around the globe. In this fast-paced and insight-rich conversation, Gary and Paul discuss: Gary's new memoir, The Trading Game: A Confession. The risks of trading currency How he felt when he got his first bonus of $750,000  Bias against wo

Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In this insight-rich conversation, Dr. Ramani explains the traits and behaviors of narcissistic individuals, how they hijack our well-being, and the motivations behind their attention-seeking behavior. She also relieves Paul of the sneaking suspicion that he might be a narcissist. Other topics include: Gender and narcissism (ladies is narcissists too!) The continuum and different types of narcissism, including: grandiose, malignant, neglectful and also self-righteous narcissism (Paul’s favorite!) How social media has amplified narcissistic behaviors and their impact on society. Gaslighting and other tools narcissists use to sow self-doubt. Which cities has more narcissists, Los Angeles or Washington D.C.? The Different roles that evolve in narcissistic family systems (the golden child, scapegoat, fixer, peacekeeper, invisible child, and truth seer)

Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues that YOU and I can improve the world by embracing our natural inclination toward generosity. He speaks not just of financial generosity, though that’s certainly a huge part of it, but also of creative generosity and generosity of spirit. In this conversation, Chris and I discuss: The formula to determine if you are a net giver or a net taker in life MrBeast and the phenomenon of performative philanthropy How gratitude can foster a sense of generosity and empathy The contribution TED has made to the world by providing a platform to share valuable ideas. How one, small act of kindness can spark generosity in others  Chris was born in Pakistan where his father was "an eye surgeon and evangelical Christian who ran a mobile hospital. He attended school in the Himalayan mountains of India before transferring to a boarding school near Bath, England. He went on to s

This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip between San Francisco where Paul had just performed at Cobb’s Comedy Club and San Luis Obispo where he was heading to perform in the SLO Fest Comedy Festival. Among other things, Paul and Mike discuss: Memories of commuting from SF to Yahoo! in Sunnyvale Why it’s hard to admit what we want in life The history of Crazy Money The possible new names for Crazy Money Life in general ✍

When John O’Leary was 9 years old, he played with fire and got burned. Like really, really burned, over 99% of his body. Doctors gave him less than 1% chance to live and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, survive he did. His journey back took years, required dozens of surgeries, and cost him all of his fingers. Today, John is a world-renowned inspirational speaker who has addressed audiences around the globe. John is also the author of the best-seller On Fire!: 7 Choices to Ignite a Radically Inspired Life and In Awe: Rediscover Your Childlike Wonder Unleash Inspiration, Meaning, and Joy. He hosts the Live Inspired podcast. John and I have a lot in common. We were both one of six kids in a big, Catholic family and raised by amazing parents who were married for over 50 years and whose humility and grace inspire us to this day. We’re both husbands and dads and both want our audiences to be radically aware of the valu

In this special “where has Paul been?” episode, Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Adventures in Affluence: Dry Cleaning - why Paul got freaked out when he starting thinking about how much he spends on dry cleaning every year. Gary v. Jerry: Why Gary Gulman Resents Rich People -Gary Gulman is an amazing comedian, but he harbors some very negative attitudes toward people who have more than he does. The Dreaded H-Word: Should Labors of Love be Tax-Deductible? - Why Paul got so upset when the IRS got judgy about this podcast.

Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.” Coleman has a new book out this week called 'The End of Race Politics: Arguments for a Colorblind America,’ in which he confronts the "failed corporate diversity and inclusion efforts and poisonous race-based policies that hurt the very people they intend to help." Coleman has been featured in the New York Times, The Wall Street Journal, The National Review, Quillette, The City Journal and The Spectator. He's appeared on many TV shows and podcasts including Real Time with Bill Maher, Making Sense with Sam Harris and the Jordan B. Peterson podcast.  In this conversation from summer of 2022, Coleman and I talk about: The Racial Wealth Gap and its origins,  Why government action including reparations is not a solution Whether 100% equality among all races is possible or even desirable,  How progressive policies that supposedly help African-Americans are actually

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 affluent. Learn more about Paul Schervish here. This episode was posted originally in April, 2022. •

This is a special holiday encore of the 2nd episode of Crazy Money with Dr. Drew, which ran Jan 30, 2019. Dr. Drew offers candid insight into the ups and downs of a career in broadcasting and medicine. From Loveline to Celebrity Rehab, Dr. Drew has been a staple on radio and cable television for over 30 years, but that doesn’t mean he’s rich — he’s got triplets to get through graduate school, after all. But he is definitely conversant on almost any topic you throw at him, including opera, coffee and Ulysses S. Grant. Oh, and doctor stuff. He knows about that too. Find out more about Dr. Drew on his website.  •

Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like your house, your car, and how much you pay for college, makes all the difference. A renowned investment strategist and author, Jared is widely recognized for his keen insights into market psychology and his ability to explain complex financial concepts in an accessible manner. He is also the author of the acclaimed book 'Street Freak: Money and Madness at Lehman Brothers' and the editor of the popular financial newsletter 'The Daily Dirtnap', where he shares his valuable perspective on the markets. Pre-order his new book, ’No Worries: How to Live a Stress-Free Financial Life’ here. On this week’s episode, we discuss: Striking the balance between being a cheap f*ck an

Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, directing, developing talent, and getting his family together for dinner. Judd has accomplished so much in his career that, in retrospect, his success appears to have been pre-ordained. But despite his massive success in the past 20 years, he never forgets his early struggles. In this week’s encore episode from Feb ’22, I speak with the writer / director / producer behind iconic comedy films such as Anchorman, Trainwreick, This is 40, and The 40-Year-Old Virgin about: Why Adam Sandler paid $50 more in rent than Judd when they were roommates Why he didn’t worry too much about finances as a young comedian How failure prepared him to handle success Being creative during a pandemic Buddhism and stuff Catch Paul Ollinger live (or tell your friends to go): Austin, Jan 11 - Buy Tickets HERE Sa

Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you possess either an interest in finance or a robust / dark sense of humor, The Counting House will make you laugh and, at times, cry in empathy with the protagonist. Gary has spent the last 25 years observing how money works from inside Goldman Sachs and the private equity business, bringing a keen writer’s eye to the money business through two previous novels, a non-fiction account of the oil and gas industrial, and a bunch of essays in The New York Times, The New Yorker and The Wall Street Journal. A Milwaukee native and longtime resident of New York, Gary now lives in New Orleans with his wife and daughter. See more about Gary and The Counting House here. In this conversation, Gary and I discuss: Investing with the constraints of a modern university stakeholders Whether your performance is you

Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you find yourself at a crossroad? Today, I speak to innovation expert Merrick Furst about how seeing ourselves and the world more clearly can tell us how to move forward when the way isn’t clear. Merrick is a Distinguished Professor at Georgia Tech. His list of academic and commercial accomplishments are longer than your arm (see below) but today we’re putting his immense analytical skills to work to determine the questions we should ask ourselves when we’re not sure about which way to go. Merrick is the co-author of a new book, The Heart of Innovation, which guides start-ups and the humans that lead them how they can go about being themselves.  In today’s conversation we discuss: What should you do when you feel stuck? How blind spots keep us stuck and how to find out what your blind spots are The importance of both radical candor and unconditional positive regard …

In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Every Day Is Thanksgiving This One Question Will Help You Stop Comparing Yourself to Others Why the Jews? The holy roots of anti-semitism might surprise you This is Us: Inconclusive Thoughts on Why We Kill Each Other During this Thanksgiving week, Paul commands you to be grateful and to savor your good fortune and your loved ones. That is all.

 ✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️

 ✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ Jennifer Wallace is a journalist and author specializing in psychology, parenting, and health. Her new book 'Never Enough: When Achievement Culture Becomes Toxic—And What We Can Do About It' delves into our modern dilemma of busyness, achievement, credentialing, and status-seeking. Katie Couric calls the New York Times best-seller 'Never Enough; “a wake up call for all of us.” A frequent contributor to the Wall Street Journal and Washington Post, Jennifer’s work explores the intersection of societal trends and individual well-being. In this conversation, Jennifer and I discuss: What Harvard can and can’t do for you (or your child) The 6 factors that contribute to a great college experience Why it matters that our kids know they matter Stress, grind culture, and mental health\ The importance of chores for children and teens The family chore that young Jennifer put off until Sunday night What Alanis Morissette was telling us in her

Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the United States in the late 1970s and early’80s. Triumph was known for its BIG live shows featuring lights, pyrotechnics, and lots of spandex (as was appropriate for the era!). Along with Rik's bandmates Gil Moore and Mike Levine, the power trio played loud, guitar-forward tunes with uplifting lyrics. 1981’s Allied Forces sold over a million copies in the US and included the songs “Fight the Good Fight” and “Magic Power,” which—if you haven’t heard it recently—merits a listen on your favorite music app. Eventually, disputes with the record label, the financial stress of touring / recouping advances, and intra-band competition lead to Triumph’s break-up. In his new memoir, Lay It on the Line: A Backstage Pass to Rock Star Adventure, Conflict and Triumph, Rik shares insights into the trials and tribulations of the rock n roll life and how he has found peace as a devoted

When Daniel Carcillo played in the NHL, he was known as an enforcer so tough and volatile that he earned the nickname “Car Bomb.” In his 12 seasons in the NHL, Daniel was a member of two Stanley Cup-winning teams (2013 and 2015 Chicago Blackhawks), led the league in penalty minutes, and was fined or suspended by the NHL 12 times. He also suffered about a dozen concussions and was diagnosed with early-onset dementia at 30 years old. As he told me, “I know I have CTE,” a progressive and fatal brain disease that he believes drove him to the brink of suicide until—as he describes it—mushroom therapy saved his life. Today, Daniel is a brain health advocate and the Founder/ CEO of Wesana Health, a life sciences company that leverages psilocybin-based medicine to treat traumatic brain injuries. In this episode, Daniel and I discuss: Whether winning the Stanley Cup made him happy The culture of violence in the NHL. The epidemic of brain injury among athletes. How psilocybin, mushrooms, MDMA, Ketamine, and other n

Over the past 30 years, Cal Fussman has interviewed a breathtaking array of the world’s most fascinating people, including Nelson Mandela, Clint Eastwood, Barbara Walters, Richard Branson, Muhammed Ali, Mikhail Gorbachev, Neil Young, Serena Williams, Tim Ferriss, Kobe Bryant, Al Pacino, Pelé, and hundreds more. He co-authored Larry King’s memoir and won a James Beard Award for a story about his journey to become a sommelier. Today he hosts the Big Questions podcast and speaks on big stages, all over the world. Cal was in Atlanta last week for one such event so we scheduled time for him to swing by my house (this is Paul typing