Reasonably Happy with Paul Ollinger

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....

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...

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 stu...

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...

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 overdo...

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 attracti...

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...

The news from the economic world is pretty bad right now. Inflation up and the stock market’s down, which means we're all experiencing some degree of financial stress. Here to help us put it all in perspective is Ken Honda. Known as Japan’s Zen millionaire, Ken’s book Happy Money has sold over 8 million copies worldwide. In this, his second visit to Crazy Money, we talk about: What economic fear,...

Spencer Jakab is the editor of The Wall Street Journal's Heard on the Street column and the author of a fascinating new book called The Revolution That Wasn't: Gamestop, Reddit, and the Fleecing of the Retail Investor. In January of 2021, a large group of small investors from the WallStreetBets subreddit rallied around the stock of video game retailer GameStop, which they believe had been unfairly...

Up until last year, no college athlete could legally, officially accept compensation for playing a sport at his or her college. That changed last year with a Supreme Court ruling that now allows college athletes to be compensated for the use of their Name, Image and Likeness (NIL). On today's show, I talk to Darren Rovell, a sports reporter who spent 18 years on the air with CNBC and ESPN and now...

Saudi-backed LIV Golf is throwing hundreds of millions of dollars at top pro golfers in an attempt to lure them away from the PGA Tour. The Tour is responding with massively-increased prize money and more player-friendly tournaments. Here to discuss these unprecedented changes and their unsavory ramifications is Rich Beem, winner of the 2002 PGA Championship and analyst for SKY Sports Golf. Rich s...

Maitland Ward is an adult film star and author of a new book called Rated X: How Porn Liberated Me from Hollywood. Best known for her role as Rachel Maguire on Boy Meets World, Maitland enjoyed a successful career as a Hollywood actress before making the transition into the adult film industry. Her videos and photos on OnlyFans now earn her over $1 million per year. And that's in addition to the m...

I've got a great conversation to share with you today about international banking, massive drug cartels and billions and laundered money. My first guest is Chris Blackhurst. He's the author of a book called Too Big to Jail: Inside HSBC, the Mexican drug cartels and the biggest banking scandal of the century. And if you think about that, we've already had a couple of big banking scandals, so this i...

Carlos Ghosn is the former CEO of both Renault and Nissan. Japanese authorities arrested him for (allegedly) paying himself tens-of-millions in unreported income (and some other shady stuff). Carlos escaped the brutal Japanese judicial system by having himself smuggled out of the country in a box! My guests Nick Kostov and Sean McLain are Wall Street Journal reporters whose new book, BOUNDLESS: Th...

Why in the world is student debt treated differently than all other kinds of debt? Why does the cost of college keep sky-rocketing? Why do colleges and universities have so little skin in the game when it comes to the debt students incur to attend these institutions? On this week’s Crazy Money, Oren Cass helps answer these important questions about higher education in the U.S. The author of ‘The O...

Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management and the author of several books about investing. He is the founder of the blog ‘A Wealth of Common Sense’. He is, also, a co-founder and co-host of the podcast, Animal Spirits with Michael and Ben, which is an informative and fun podcast about the markets and the economy, et cetera. On this week's episode,...

Andrew Yang is a former Presidential candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for structural reform to safeguard our democracy. He lays all this out in his new book, Forward, which we discussed today. We also discuss Andrew's life as a teenager, his obsession with post-punk bands like The Smiths, Depeche Mode, and Nine Inch Nai...

Today’s guest is Coleman Hughes, he's a writer, podcaster and opinion columnist who specializes in issues related to Race, Public Policy and Applied Ethics. He 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 Har...

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 becom...

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 Circl...

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...

This is an encore epsiode with Professor Barry Schwartz, author of several books, including Why We Work and The Paradox of Choice. I spoke to Barry in August, 2020 about his findings in these two important books. Prevailing social wisdom is that more is better, and that more choices should yield much greater satisfaction. So why is it that the harder we work and the more affluent we become, the mo...

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 cal...

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 grea...

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 t...