Reasonably Happy with Paul Ollinger

A working class kid from the poor part of Connecticut, Jared Dillian somehow managed in 2001 to land a job as a trader at Lehman Brothers, the then-prestigious investment bank. Wearing cheap suits from the Mens Wearhouse, he found himself out-of-place among the Armani-clad Ivy League set on Wall Street. But he loved trading and made a lot of money in the process. In this candid conversation, Jared shares frank insights into the incredible stress of trading and the mental health that became apparent as his career progressed. Those persistent mood swings turned out to be a symptom of undiagnosed Bipolar disorder, which resulted in him spending three weeks in the psychiatric ward, a place he described as “a very healing environment." After Lehman went bankrupt, Jared pivoted to a successful writing career. Today, he is the Editor of The Daily Dirt Nap, an investment newsletter providing daily market commentary and insight to traders and very serious investors. He has also written two books: Street Freak: A Memoir of Money and Madness, a gripping read which chronicles his time as a trader with Lehman Brothers from 2001-2008, and the novel, All The Evil of this World, which Paul is looking forward to reading.   Jared graduated from the US Coast Guard Academy and earned his MBA From University of San Francisco. When he’s not writing or taking care of his 5 cats, he is making music under the name, DJ Stochastic. He lives in Pawleys Island, South Carolina. Learn more about The Daily Dirtnap  Check out Jared’s music here.  Jared’s radio show here   Please take a second to rate and review Crazy Money here. (Click on “your" app)Follow Paul on Instagram.Topics covered in this episode include investments, trading, Wall Street, Lehman Brothers, writing, mental health, bipolar disorder, OCD, Bloomberg, Matt Levine 

My guest today paid a dowry of eight cows for his first wife and six cows and three sheep for his second wife. Josphat Mako, or just “Mako," grew up in Kenya’s Maasai Mara, a massive plain just north of the Serengeti. He taught himself English, learned how to drive, and has since become become a well-known safari guide for the legendary Cottars camps.  In today’s episode, we talk about his childhood, daily life in the Maasai Village, who goes to school in their culture (it will surprise you!), and what it was like when he attended a football game at the University of Alabama in Tuscaloosa. Special thanks to Ann Short travel here in Atlanta, Bush & Beyond in Nairobi and the good people at Cottars Conservation camp in the Mara. See photos from our trip are in the Crazy Money Listeners group in Facebook.   See the Sidecar hat carrier here. Get tickets to see Paul at MadLife Studios here.  Rate and review Crazy Money here.   Topics covered in this episode include: #alabamafootball #maasai #maasaimara #travel #safari #africaUnlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.

(Originally posted October, 2019) Ryan Holiday is the author of ten books, which have sold sold more than 2 million copies worldwide and been translated into 30 languages. World-class athletes, celebrities and political leaders use his lessons to achieve peak performance. His 2014 book, The Obstacle Is The Way, was read by the New England Patriots during their 2014 Super Bowl-winning season and by four-time major champion golfer Rory McIlroy as preparation for the 2019 Masters Tournament.  In this conversation, recorded in September, 2019, we discuss his then-upcoming release, Stillness is the Key, the author explores how each of us can find wisdom in our lives by slowing down and quieting the barking dogs in our head. Ryan is also the founder of Daily Stoic, a community of 200,000 people dedicated to leading better lives by contemplating the ancient philosophy.  Find Ryan on http://dailystoic.com Find Paul on http://PaulOllinger.com Email Paul at Paul@CrazyMoneyPodcast.com TICKETS to Paul’s upcoming comedy shows: https://laughingskulllounge.com/ Subjects covered this week include: Stoicism, Buddhism, Money, ambition, pride, stillness, meditation, Marcus Aurelius, memento mori, Daily Stoic, books, authors 

Communicator, author, and pastor Andy Stanley founded Atlanta-based North Point Ministries (NPM) in 1995. Today, NPM consists of seven churches in the Atlanta area and a network of nearly 100 churches around the globe that collectively serve nearly 185,000 people weekly. A survey of U.S. pastors in Outreach magazine identified Andy as one of the ten most influential living pastors in America. Andy holds an undergraduate degree in journalism from Georgia State University and a master’s degree from Dallas Theological Seminary. He is the author of more than 20 books, including Irresistible; The New Rules for Love, Sex & Dating; How to Be Rich; Deep & Wide; Enemies of the Heart; When Work & Family Collide; Visioneering; and Next Generation Leader.His success reaches well beyond the Atlanta area. Over 10.5 million of his messages, leadership videos, YouTube videos, and podcasts are accessed each month. He is the host of the TV show, Your Move with Andy Stanley, which airs in major markets after Saturday Night Live.In this episode, Andy and I discuss what Jesus taught regarding money, wealth, and charity. And why it’s a great idea to always GIVE FIRST. Learn more about Andy’s ministry here and watch Your Movehere. **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here.Read Paul’s latest thoughts on life on Medium.  Topics covered in this episode include: money, church, rich, pastor, Jesus, christians, christianity, churches, tithe, charity, philanthropy, gospel, living About Crazy Money:Unlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.Are you really still reading? Go listen to another episode, silly.

Comedian Paul Ollinger started Crazy Money to explore the connection between money, happiness, work, and meaning through the lens of his guests' expertise and/or money journeys. Preveious interviewees include prominent authors, academics, CEOs, celebrities, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic Gold medals, including: Academics: Princeton's Sir Angus Deaton (Nobel laureate) and Peter Singer (“the world’s most influential living philosopher”), Yale’s Laurie Santos, Brookings' Richard Reeves, Jonathan Rauch, and Carol Graham, Oxford’s Will MacAskill, UC Berkeley’s Barry Schwartz on The Paradox of Choice, Yale Law School’s Daniel Markovits. Journalists: Ron Lieber (NYT), Paul Sullivan (NYT), Paul Tough (NYT), Adam Minter, Oliver Burkeman (The Guardian). Best-selling authors: Ryan Holiday, Bill Browder, Lori Gottlieb, Michael Arceneaux, Christopher Ryan, AJ Jacobs, James Altucher, Jesse Itzler, Lisa Birnbach. Broadcasters: Guy Raz, Dr. Drew Pinsky, Adam Carolla, Bobbi Rebell. Others of interest: LL COOL J, Lord John Browne (CEO of BP, 1995-2007), Danny Wuerffel (Heisman Trophy winner now working with the urban poor), Apolo Ohno (8-time Olympic medalist), Rich Beem (PGA championship winner); comedians Rory Scovel and Kyle Kinane. Everyday folks: My dad (discussing raising six kids on a modest salary), My wife (talking about how we talk about money), AJ Jain (on losing everything and starting over), Julie Saxon on maintaining a career and sanity during her husband’s 6-year battle with cancer.

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, Mama Said Knock You Out, Rock The Bells, and many, many more. As an actor, he has played “Sam Hanna” on NCIS: Los Angeles for the last 12 years, appeared in hit films like In Too Deep, Any Given Sunday, and Wildcats, and starred in the NBC sitcom, In the House.In this, the 100th original interview of Crazy Money, LL shares what he really wanted when he released his first record, how he approaches potential business deals, and why he pours his soul into Rock The Bells, his company that elevates timeless and classic Hip-Hop culture by celebrating MC’s, DJ’s, Break Dancers and Graffiti artists on its website, found here. LL also created and curates programming for the radio channel of the same name on SiriusXM Channel 43. **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here.Read Paul’s latest thoughts on life on Medium.  Topics covered in this episode include: hip hop, music, rap, culture, money, wealth, motivation, inspiration, persistence, work ethic, black money, racial wealth divide.About Crazy Money:Unlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth management, culture, society, status.

“Never tell anyone a secret because they will surely use it against you.” That’s what Lord John Browne’s mother, an Auschwitz survivor, always told her son. The former CEO of BP followed her advice until he was 59 years old when his secret—the fact that he was a closeted gay man—was exposed by an ex-boyfriend in the British tabloids.  The revelation resulted in a media storm and Lord Browne’s immediate resignation. Just like that, after almost 40 years of service to his employer, he was out of a job and out of the closet. Keep in mind that in the few years before he was outed, Lord Browne had been knighted by Queen Elizabeth II, named to the house of Lords, won the UK’s “Most Admired Leader” Award 4 times in a row. John Browne, Baron Browne of Maddingley served as BP's CEO from 1995 until 2007. When he took the helm, the company was called British Petroleum. The re-branding to BP was only one of several major accomplishments during his tenure. He also engineered mergers with Amoco, Arco, and oversaw major exploration projects around the globe.  Lord Browne is the former President of the Royal Academy of Engineering and has served on the boards of Intel, Daimler-Benz and Goldman Sachs. He is the author of five books, including The Glass Closet: Why Coming Out is Good for Business, which is what we disussed in most detail today. He holds a BA in Physics from St. John’s College, Cambridge and earned a Masters at Stanford.  See a list of countries that still have the death penalty for homosexuality here. Learn more about Lord Browne on his Twitter feed and his foundation’s website. **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy MoneyListeners Group here.Read Paul’s latest thoughts on life on Medium.  Topics covered in this episode include: business, leadership, executives, oil, fossil fuels, LGBT, homosexuality, inclusivity, diversity, inclusion, homophobia, gay employeesAbout Crazy Money:Unlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, Rat Race, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.Are you really still reading? Go listen to another episode, silly.

James Altucher is an author, chess master, podcaster, former hedge fund manager, angel investor, and — just to top it off —comedian. Oh, he’s also an entrepreneur who has started 20 companies, 17 of which failed. Over the course of his career, James has made and lost multi-million dollar fortunes “three or four times.”  The Wall Street Journal best-selling author of Choose Yourself, Choose Yourself Guide to Wealth, and The Power of No has  a new book, Skip the Line that is all about how thinking linearly and doing things the way they have always been done will get you exactly nowhere. Oh, he also owns a comedy club. You’ll hear all about this.  Learn more about James’ podcast and books on his website. Here’s his NY Post essay, New York City is Dead Forever (you probably read this). **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here.Read Paul’s latest thoughts on life on Medium.  Here’s the link to my 2019 interview with my wife, Stacey, talking about how we talk about money. About Crazy Money:Unlike traditional personal finance shows,Crazy Moneyis not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, Rat Race, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.Are you really still reading? Go listen to another episode, silly.

Rachel Greenwald is a professional match-maker whose business serves wealthy men looking for love. A graduate of Harvard Business School where she is an Executive Fellow, Rachel is also the New York Times bestselling author of Have Him at Hello and Find a Husband After 35. In today’s episode we discuss the mistakes both men and women make when talking or inquiring about money during courtship. She also divulges the #1 mistake successful women make on first dates, as reported in interviews with over 1,000 men. (Some of you won’t like this, so it’s that much more important that you listen!) An expert on building successful relationships in both love and work, Rachel also helps corporate executives improve their professional relationships, deepen connections among their teams, and elevate their EQ skills by using tactics honed through her two decades of match-making. Learn more about Rachel and her books on her website. **Please rate and review Crazy Money.**Follow Crazy Moneyon Instagram hereand join theCrazy MoneyListeners Group here.About Crazy Money:Unlike traditional personal finance shows,Crazy Moneyis not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, Rat Race, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.Are you really still reading? Go listen to another episode, silly.

Holly Parker is one of the most dynamic people I have ever met. A top NYC realtor who has sold over $8 billion in property, she is also a self-made millionaire, consummate connector of people, world traveler, twin mom, and author. In her new book, Back on the Market: A Realtor’s Guide to Love and Life Holly tells the story of her divorce, re-entry into the dating world as an ultra-successful woman, and how she earns the trust of billionaires who purchase $50mm+ apartments.  On this week’s episode Paul and Holly talk about the source of her (and to an extent, his) motivation: an anxiety born of wanting to be seen, liked, and respected. And about how she channels that energy to destroy her sales goals and give back to the world.  Learn more about Holly on her website. Buy the book here. **Please rate and review Crazy Money.**Follow Crazy Money on Instagram here and join the Crazy Money Listeners Group here.About Crazy Money:Unlike traditional personal finance shows,Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, Rat Race, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, mid-life crisis, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth, wealth management, culture, society, status.Are you really still reading? Go listen to another episode, silly.==== Outro: Check out the book. Link is in the show notes. Back on the Market.  Takeaways: 1. You never know what’s going on with someone else. When you compare, you have to take the 2. Some of the most successful people I know are dealing with anxiety. Money is something we look at the same way we looked at our report cards in high school. I must be doing okay if I am making all A’s. 3. A big part of your wealth and your health are the people you are lucky enough to meet on the way. When you