Life after the PGA Championship (with Rich Beem) rebroadcast
Crazy Money with Paul Ollinger
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...
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The Problem with Choice (with Barry Schwartz)
Crazy Money with Paul Ollinger
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 more depressed we get? More choice, Barry argues, not only overwhelms us, but raises our expectations and makes us doubt our decision-making. Too much choice increases our anxiety and makes us less...
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Hedge Fund Novelist (with Jay Newman)
Crazy Money with Paul Ollinger
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...
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The Puzzle of Life (with A.J. Jacobs)
Crazy Money with Paul Ollinger
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!),...
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Money and Comedy (with Christian Finnegan)
Crazy Money with Paul Ollinger
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 . 🔥Join Team Ollinger .🔥 💪🏼 Rate and Review Crazy...
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The Joys and Anxieties of Wealth (with Paul Schervish)
Crazy Money with Paul Ollinger
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...
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Mid-Life Career Re-invention (with Chip Conley)
Crazy Money with Paul Ollinger
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...
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Fixing Financial Chaos (with Joe Saul-Sehy)
Crazy Money with Paul Ollinger
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...
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Jacob Goldstein
Crazy Money with Paul Ollinger
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...
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Comparison and the Ultimate Money Delusion
Crazy Money with Paul Ollinger
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...
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