Reasonably Happy 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...

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 journ...

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 hi...

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 a...

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. A...

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 h...

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. E...

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 C...

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 r...

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 t...

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 t...

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 me...

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 c...

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 translate...

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...

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...

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...

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 revie...

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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 Leagu...

That voice in your head isn’t all bad. Sure, it sometimes tells you you’re not good enough or that Bob from Accounting is plotting to get you fired, but your inner dialog can be your friend if you take the time to get to know it. Dr. Ethan Kross is the author of Chatter: The Voice in Our Head, Why It Matters, and How to Harness It. A Professor of Psychology at the University of Michigan and one of...

Lisa Birnbach is the author of over 20 books, includingThe Official Preppy Handbook, which became a cultural phenomenon in the early 1980’s. The book sold more than a million copies, has been cited as an inspiration to the founder of J. Crew and is thought to have boosted the growth of LL Bean.  InT.O.P.H., Birnbach celebrated, skewered, and democratized the concept of preppiness with writing the ...

What would happen if the richest neighborhood in your town declared itself its own municipality, taking with it the tax dollars of the richest 20% of citizens? That is what might happen here in Atlanta where a well-funded group is petitioning to carve the wealthy neighborhood of Buckhead (coincidentally, where I live) away from Atlanta, into its own city. This initiative has gained traction and ha...

Educated at Brigham Young and Emory Universities, Dr. Daniel Crosby is a psychologist and behavioral finance expert who studies and writes about the intersection of financial markets and the human brain. A New York Times best-selling author, Daniel has published several books, including The Laws of Wealth and The Behavioral Investor, which we discuss in this episode.  His ideas have appeared in th...

J.R. Martinez joined the Army to give back to the country that accepted his immigrant, single mother and to earn money for college. As a 19-year-old, handsome Infantryman, he quickly deployed to Iraq. One bad day, his Humvee hit a roadside bomb, trapping J.R. inside where burning fuel literally melted the skin from his face and consumed one of his ears. J.R.’s buddies pulled him clear but not befo...