Crazy Money with Paul Ollinger

Life after the PGA Championship with Rich Beem - ENCORE EPISODE

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 wo...

The Problem with Choice (with Barry Schwartz)

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 expectati...

The Problem with Choice with Barry Schwartz - ENCORE EPISODE

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 expectatio...

Hedge Fund Novelist (with Jay Newman)

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 wi...

Hedge Fund Novelist (with Jay Newman)

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 cajones, 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 w...

Hedge Fund Novelist with Jay Newman - Ep 145

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 wit...

The Puzzle of Life (with A.J. Jacobs)

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 th...

The Puzzle of Life (with A.J. Jacobs) - Ep 144

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 era...

Money and Comedy (with Christian Finnegan)

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 Ollinge...

Money and Comedy with Christian Finnegan - Ep 143

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 h...

The Joys and Anxieties of Wealth (with Paul Schervish)

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...

The Joys and Anxieties of Wealth with Paul Schervish - Ep 142

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 in...

Mid-Life Career Re-invention (with Chip Conley)

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 fou...

Mid-Life Career Re-invention with Chip Conley - Ep 141

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 found...

Fixing Financial Chaos (with Joe Saul-Sehy)

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—wealt...

Fixing Financial Chaos with Joe Saul-Sehy - Ep 140

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 m...

Jacob Goldstein

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 befo...

What’s Your Problem? with Jacob Goldstein - Ep 139

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 w...

Spring Break Essays

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 w...

Comparison and the Ultimate Money Delusion

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 w...

Comparison and the Ultimate Money Delusion - Ep 138

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 wha...

Why Things Are Better than You Think (with Grant J. Ryan)

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 ...

Why Things Are Better than You Think with Grant J. Ryan - Ep 137

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 bil...

Founder of Russian Hedge Fund on Defying Putin (with Bill Browder) - ENCORE

Bill Browder is the author of Red Notice: A True Story of High Finance, Murder, and one Man’s Fight for Justice, which is the best book I’ve read in a decade (and I read a lot of books). Red Notice is the story of how Browder turned a $25 million investment into a $4 billion hedge fund (Hermitage Capital) by exposing corruption in the newly opened Russian economy of the late 90’s and early 00’s. Eventually, Browder’s efforts to shine light on the newly privatized industries, cut too close t...

Founder of Russian Hedge Fund on Defying Putin with Bill Browder - ENCORE EPISODE

Bill Browder is the author of Red Notice: A True Story of High Finance, Murder, and one Man’s Fight for Justice, which is the best book I’ve read in a decade (and I read a lot of books). Red Notice is the story of how Browder turned a $25 million investment into a $4 billion hedge fund (Hermitage Capital) by exposing corruption in the newly opened Russian economy of the late 90’s and early 00’s. Eventually, Browder’s efforts to shine light on the newly privatized industries, cut too close to ...

LL COOL J (encore)

Nobody works harder than LL COOL J. The musician, producer, actor, and entrepreneur has been playing at the highest levels of art, business, and culture since he burst on the scene at the age of 17, in 1985. For over 35 years, LL has pushed himself to achieve in all that he does while leading with spirit and character. And achieve he has. The two-time GRAMMY-winner and first ever Hip Hop Kennedy Center Honoree has recorded 14 studio albums, landing massive hits including Going Back to Cal...

LL COOL J - ENCORE EPISODE

Nobody works harder than LL COOL J. The musician, producer, actor, and entrepreneur has been playing at the highest levels of art, business, and culture since he burst on the scene at the age of 17, in 1985. For over 35 years, LL has pushed himself to achieve in all that he does while leading with spirit and character. And achieve he has. The two-time GRAMMY-winner and first ever Hip Hop Kennedy Center Honoree has recorded 14 studio albums, landing massive hits including Going Back to Cali, ...

Judd Apatow on Fame, Money, and the Creative Process

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 cre...

Judd Apatow on Fame, Money, and the Creative Process - Ep 136

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 creati...

Olympic Economics with Apolo Ohno (Encore episode)

In this episode, Apolo Ohno and I go deep into the economic realities of becoming an Olympian. Due to the steep cost of coaching, training, equipment, and travel, many (perhaps most) athletes and their families go deep into debt in pursuit of a spot on the national team. And even for the few who make it, there is little preparation for post-Games remuneration and little preparation for a job “in the real world.” With eight Olympic medals (two of them gold), Apolo Ohno is America’s most decor...

Olympic Economics with Apolo Ohno - ENCORE EPISODE

In this episode, Apolo Ohno and I go deep into the economic realities of becoming an Olympian. Due to the steep cost of coaching, training, equipment, and travel, many (perhaps most) athletes and their families go deep into debt in pursuit of a spot on the national team. And even for the few who make it, there is little preparation for post-Games remuneration and little preparation for a job “in the real world.” With eight Olympic medals (two of them gold), Apolo Ohno is America’s most decora...

House of Gucci author, Sara Gay Forden

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 iconi...

House of Gucci author, Sara Gay Forden - Ep 135

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 ...

Raising Successful Kids (with Julie Lythcott-Haims)

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-pa...

Raising Successful Kids with Julie Lythcott-Haims - Ep 134

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-paren...

Zen Money (with Ken Honda)

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 newbo...

Zen Money with Ken Honda - Ep 133

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 daught...

Over-thinking and What to do About It (with Jon Acuff)

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 Harvar...

Over-thinking and What to do About It with Jon Acuff - Ep 132

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...

From the Trailer Park to the Comedy Big Time (with Rocky Dale Davis)

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...

From the Trailer Park to the Comedy Big Time with Rocky Dale Davis - Ep 131

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 K...

Life After Public Failure

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, Wa...

Life After Public Failure with Warwick Fairfax - Ep 130

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 t...

$50 Million Mistakes (with Ali Partovi)

Ali Partovi is an Iranian-American entrepreneur 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...

$50 Million Mistakes with Ali Partovi - Ep 129

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! T...

What HBO's Succession Tells us about Wealth (with James A. Miller, Meredith Blake and David Lenok)

Today we will be discussing the enthralling HBO series, Succession and all it tells us about wealth, dysfunctional family dynasties, ambition, and greed with three great panelists, including Meredith Blake from the Los Angeles Times, Dave Lenok from WealthManagement .com, and James Andrew Miller, author of the new book Tinderbox: HBO’s Relentless Pursuit of New Frontiers.    (**Please rate and review Crazy Money here.**)   In case you’ve been asleep for the past three years, here’...

What HBO's Succession Tells us about Wealth with James A. Miller, Meredith Blake and David Lenok - Ep 128

Today we will be discussing the enthralling HBO series, Succession and all it tells us about wealth, dysfunctional family dynasties, ambition, and greed with three great panelists, including Meredith Blake from the Los Angeles Times, Dave Lenok from WealthManagement .com, and James Andrew Miller, author of the new book Tinderbox: HBO’s Relentless Pursuit of New Frontiers.  (**Please rate and review Crazy Money here.**) In case you’ve been asleep for the past three years, here’s a brief synops...

Thanksgiving Essays

Thanksgiving Essays - Ep 127

Investing for Good (with Judith Rodin, Joan Salwen, and Pieter van der Gaag)

This week I speak to three distinguished guests about how money can be used to make the world a better place and how investors large and small can influence corporations to be more responsible global and local citizens.    Up first is Dr. Judith Rodin, former President of both The Rockefeller Foundation and the University of Pennsylvania where she was the first woman to permanently lead an Ivy League Institution. Judith is the author ofThe Power of Impact Investingand Making Money Moral:...