

Reasonably Happy with Paul Ollinger
Paul Ollinger
Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.
Episodes
Mentioned books

Feb 14, 2023 • 58min
New Fame, New Money with Katherine Blanford
A year ago, Katherine Blanford was working as a nanny by day and doing comedy at night. Last summer, she made her network television debut on The Tonight Show with Jimmy Fallon and is now headlining around the country and opening for David Spade. She and I discuss the experience of having "heat" and cash in her pocket for the first time. We talk about artistic envy, the work ethic needed to succeed in comedy, what she learned about wealth and careers while working as a nanny, and of course, how much she loves the Ollinger family basement. 🔥 Follow Katherine on Instagram here. 🔥💪 Subscribe to Paul’s Substack here. 💪

Jan 2, 2023 • 22min
Crazy Money's direction in 2023
Hey everybody. Happy 2023! This is a short, lightly edited greeting from Paul /me about where the podcast has been in 2022 and where we're going to take it in the year to come. I am grateful for your continued support and interest. I wish you and your family a safe, prosperous, and fulfilled year.Carpe Diem!✍️ Subscribe to Paul's Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥📧 E-mail Paul at Paul@CrazyMoneyPodcast.com 📧 Crazy Money is produced and edited by Mike Carano. Topics addressed on Crazy Money include: Money, Happiness, Contentment, Meaning, philosophy, dreams, purpose, Success, mental health, Business, Work, Careers, Authors, Books, Values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society. Status.If you haven’t found what you’re looking for in the words above, you’re probably not going to find them down here. Seriously, all the important stuff is up yonder.

Dec 20, 2022 • 48min
How Your Mindset Can Change Your World with David Robson
The philosophical martial artist and actor, Bruce Lee is supposed to have said, “So you think, so shall you become.” On this week’s episode, we explore the power of positive expectations with David Robson, an award-winning science writer and author of the new book The Expectation Effect: How Your Mindset Can Change Your World. As you’ll hear, David makes a strong argument supporting Bruce Lee’s message: that positive expectations can meaningfully improve our lives. To be clear, this is not about the Law of Attraction. Robson bases the book on data gleaned from the scientific method. These studies provide ample evidence that our expectations can make us healthier, smarter, and significantly improve our aging prospects. (For better or worse–well, worse–the opposite is also true.)It’s important to note, as Robson and I discuss, that your expectations don’t just change your world. They also change the lives of others because our expectations of them–and theirs of us–have an impact on our respective lives. So we kind of owe it to each other to expect the best. In this chat we talk about how routine or process can help get us out of our heads before an important event. We explore the damage caused by guilt and shame, and why worrying about worrying (‘Meta Worrying’) or stressing about stress, might be the most dangerous thing we can do. Most importantly, he provides methods by which to break ourselves out of these bad habits when we find ourselves slipping into them. And that’s important because our expectations can change the world.🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow David Robson:Twitter - https://bit.ly/3PEkgps (@d_a_robson)Instagram - https://bit.ly/3G7VuL8 (@davidarobson)Website - https://davidrobson.meAmazon - https://amzn.to/3PvliUC

Dec 6, 2022 • 59min
Growing Up Rich with Kristin Keffeler
Kristin Keffeler is the author of a new book called The Myth of the Silver Spoon: navigating family wealth and creating an impactful life. Kristin is also the founder of Illumination360 where she works with ultra high net worth families, including many worth billions of dollars. Her specialty is helping the rising generations create their own identities having grown up with extreme family wealth.In this conversation, Kristin and I talked about how her own family's affluence led her into this field; the specific doubts and fears that teen and adult inheritors of generational wealth have to deal with. We talked about the negative messages that society sends to wealthy children, about the balance rising generation members must strike owning their family name, but creating their own. We talked about how all parents—especially wealthier ones—can model financial behavior for their kids. And lastly, we discuss what the NFL Hall of Fame can teach us about the likelihood of measuring up to our wildly successful parents or grandparents. ✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Kristin Keffeler:Website - https://illumination360.com/mythThe Myth of the Silver Spoon: The Book - https://amzn.to/3i6qFwN

Nov 22, 2022 • 46min
Why Boys and Men are Struggling with Richard Reeves
Richard Reeves is a senior fellow at the Brookings Institution and the author of a new book called Of Boys and Men: Why the Modern Male Is Struggling, Why It Matters, and What to Do about It. You might ask, “Why is this topic relevant to Crazy Money, a podcast about money and happiness, work and meaning?” Because the connection between education, gainful employment and life satisfaction is massive. And on these metrics, the modern male is not doing well. Consider some of these data points: Boys are 50% more likely to fail classes in math, reading and science than girls. By High School, 2/3 of the students in the top 10% of the class ranked by GPA are girls, while about 2/3 of the students in the lowest 1/5 of the class are boys. And education matters. One in three American men with only a high school diploma (10 million men!) are now out of the labor force. They're not unemployed–they're out of the labor force. They're not even counted in the unemployment numbers. And this matters because men without education and jobs do less well as husbands and fathers and thus perpetuate the cycle for their children. Yes, especially for their sons. Perhaps worst of all, men make up 75% of those who die by deaths of despair, i.e. by suicide, or acute substance abuse. The net of it is when you lose hope in the future, you will become increasingly volatile in the present. You've probably read Richard's writing in the New York Times, The Guardian, The Atlantic or the Wall Street Journal, his previous book Dream Hoarders, which The Economist named a Book of the Year.. I'm delighted to have him back on the show.🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Richard Reeves:Twitter - https://bit.ly/3EBSXIo (@RichardvReeves)Of Boys and Men: The Book - https://a.co/d/3SnjEhQWebsite - https://richardvreeves.com

Nov 15, 2022 • 58min
The Need to Belong with Geoffrey L. Cohen
We don't think about it all the time, but BELONGINGNESS is the third most fundamental desire on Maslow’s Hierarchy of Needs. Just above safety and physiological requirements, is our need to feel safe as part of a tribe. My guest this week is Geoffrey L. Cohen, the author of Belonging: the Science of Creating Connection and Bridging Divides. Geoff is a professor of Psychology and Organizational studies at Stanford University in Palo Alto, California. In this conversation, he and I talk about what it means to belong to a place, an organization, a family or a movement; We explore how belongingness and identity are intermixed, and what implications that has for discussing politics and other beliefs with people who have differing points of view. We talk about how to design diversity training so it doesn't alienate half the room (maybe we should call it “Belongingness Training”). We also talk about what groups you'd rather not belong to, because while belongingness is important, some tribes are better than others!🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Geoff Cohen:Twitter - bit.ly/3UVv5F4Website - www.geoffreylcohen.com

Nov 9, 2022 • 48min
The Hedge Fund Legend Hugh Hendry
Former hedge fund manager Hugh Hendry grew up working class in Glasgow, Scotland. His anxiety, detachment from money, and passionate observations of life led him to hypotheses and market positions others couldn’t see. In 2008, when the rest of the world was melting down, Hugh’s Eclectica Asset Management returned over 30%. As great as the money was, he says what drives him is a profound need to be loved. Today, Hugh develops property in St. Barths where he lives full time.In this conversation, Hugh shares anecdotes of Scottish thrift that will make you laugh, an honest description of how it feels to lose millions of other people's dollars, why closing his hedge fund felt “as if you've died in Mortal Kombat,” and why we should all be mindful of “the profound wrongness of today.” We spoke at the Stansberry Research conference in Boston in October.🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Hugh Hendry:The Acid Capitalist podcast - https://apple.co/3FX3D5vTwitter - https://bit.ly/3UKgfBgInstagram - https://bit.ly/3UDczkAWebsite - acidcap.com

Nov 3, 2022 • 45min
Money and Opioids with Barry Meier
Barry Meier is a former investigative reporter at The New York Times and the author of the book, Pain Killer: An Empire of Deceit and the Origin of America's Opioid Epidemic, which explores how the Sackler family's greed catalyzed a plague of addiction and death that has destroyed families and whole communities across the country.Between 1999 and 2000, 564,000 Americans died from an opioid overdose. In 2020, the most recent year for which statistics are available, there were over 68,000 opioid overdoses in the U.S. That's 188 per day and each one of these deaths represents a son or daughter, a brother or sister or a mother or father, who is not coming back. People died of opioid overdoses before the 1996 launch of OxyContin, but it’s clear that Oxy and Purdue Pharma’s (owned by the Sacklers) aggressive and deceptive marketing practices threw gasoline on a spark that has turned into a raging wildfire. In 2023, Netflix will launch a miniseries based on Pain Killer.In our conversation today, Barry and I discuss the Sacklers’ family legacy of ethically dubious marketing of pharmaceuticals and how they made tens of billions of dollars selling OxyContin using the same techniques, like pushing free samples, knowing that the drug was quite addictive. We discuss how and why the FDA approved claims that OxyContin was less prone to addiction in the complete absence of evidence proving that it actually was. And lastly, we discuss the extent to which OxyContin kicked off this opioid epidemic for which there is no clear way out.🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Barry Meier:barrymeier.comnytimes.com/by/barry-meierPain Killer: The Book - https://a.co/d/b9cEPHS

Oct 25, 2022 • 53min
Why Status Matters with Will Storr
Where do you sit on the social hierarchy?You might not think about it daily, but if I asked you to compare your status to that of one of your friends, you'd probably know the answer: above some, below others, and probably on about the same level as most. Perhaps you'd follow up with questions like “Do you mean who has more money? Or who has more recognition in the community or who's more attractive or physically fit?” This request for clarification demonstrates the nature of status, and how we go about gaining it and retaining it, whether or not we are conscious of our efforts to do so.My guest this week is Will Storr. He's the author of a fascinating book called The Status Game. The author of six critically acclaimed books, including The Status Game, Selfie, and The Science of Storytelling, Will’s writing has appeared in The Guardian, The Sunday Times, The New Yorker and the New York Times. And his journalism has been recognized with awards from the National Press Club, the One World Press and Amnesty International. If I haven't yet convinced you of his status, I’ll also share that he's a great looking guy who grows giant yams. (You'll understand that reference about 20 minutes into the episode.)In this conversation, Will and I discuss why status matters; Whether the pursuit of status is a fool's game for small minded people with totally fragile egos; We talk about a totally bizarre source of status in Polynesia that demonstrates the arbitrariness and locally relative nature of status. We talk about whether it's better to be a big fish in a small pond or a small fish in a big pond. We talk about how the quest for status shows up in politics and religion and boy does it ever and lastly, we discuss how the thirst for status among even the most rich and famous among us, like Sir Paul McCartney, demonstrate the insatiable need for this elusive and addictive drug that is STATUS.🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow Will Storr:Twitter - https://bit.ly/3D84YVg (@wstorr)The Status Game: The Book - https://amzn.to/3TnazNi

Oct 18, 2022 • 58min
Money in College Sports, Part 2 (with AJ Vaynerchuk and Laine Higgins)
This episode is Part Two of our Money in College Sports: NIL series. Until last year, college athletes were prohibited from collecting any compensation. But today, thanks to Name, Image, and Likeness (NIL) deals, the stakes are high and getting higher. To make sense of this issue, I speak with A J Vaynerchuck from Vayner Sports and Laine Higgins from the Wall Street Journal.A J Vaynerchuk is the co-founder of sports management agency, Vayner Sports where he has been a part of several NIL deals for some of the top athletes in the country. We talked about what brands are looking for when they partner with college athletes, how big the deals have gotten, the specifics of the deals he's done with Dr. Pepper and Kool-Aid, and we go down the road and think about just what college sports are going to look like in the next five to ten years.Laine Higgins is a former college athlete and is now a sports reporter for The Wall Street Journal where she covers, among other things, college sports. She and I discuss Title IX and its implications for the NIL deals, and what responsibility schools have for ensuring equal access for both men and women to these kinds of deals. We talk about how and why brands are structuring deals with athletes from non-revenue sports like volleyball, swimming, and track and field, and to what degree attractiveness and sex appeal drives followership on social media and thus, the potential value of an NIL deal. (Be sure to listen to that part because–even though I ask the question sincerely–I still manage to come across like a complete creep!)🎧Listen on Apple Podcasts here 🎧✍️Get Paul’s Substack newsletter here.✍️🔥Subscribe to us on YouTube here. 🔥Follow AJ Vaynerchuk:Twitter - https://bit.ly/3SZtPjt (@ajv)Instagram - https://bit.ly/3Vq0Rec (@ajv)Website - https://vaynersports.comFollow Laine Higgins:Twitter - https://bit.ly/3EJJWxh (@lainehiggins17)WSJ Articles - https://on.wsj.com/3VwSRrW


