Best Crazymoneywithpaulollinger Podcasts (2025)

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High Net Worth Divorce with Laura Wasser 40:41

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5d ago40:41

40:41

People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like Angelina Jolie, Kim Kardashian, Johnny Depp, Ryan Reynolds, Dr. Dre, Kevin Costner, Maria Shriver, and Jimmy Iovine, among many others. And while “celebrity divorce attorne…

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Surviving the College Application Process w/ Jeffrey Selingo 57:00

19d ago57:00

57:00

As the father of two prep school students, I was very eager to meet this week’s guest. Jeffrey Selingo has written about college admissions for more than 25 years and is a New York Times bestselling author of four books, including Who Gets in and Why and his latest, Dream School: Finding the College That’s Right for You. Drawing on two years of res…

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Paul’s Insights into NYC, Email, and Estate Planning 44:04

26d ago44:04

44:04

Hello friends. On this week’s episode, I read to you—like a daddy rocking his baby to sleep—the most recent posts from my Substack newsletter, which you can find here. (You can subscribe for free or pay a few bucks, if you want to support my work, but really I just appreicate you reading / listening and sharing.) These essays cover both life in gen…

1
Confronting Mortality with Thad Reichley 1:04:49

1M ago1:04:49

1:04:49

Imagine being told you have a terminal illness. Would it change the way you approach each day? Two years ago, Thad Reichley went to the doctor because he had the flu. When initial attempts to address his symptoms were unsuccessful, additional procedures revealed the presence of three dozen tumors in the lining around his lungs. He was diagnosed wit…

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Walking Away from Fame and Money with Rachel Heck 58:32

1M ago58:32

58:32

Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at Stanford University, where she went on to win both individual and team national championships and became Nike Golf’s very first NIL sponsored athlete. But when the time came to turn pro, Rachel deci…

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Family, Politics & The American Dream with Raj Goyle | Reasonably Happy 53:44

2M ago53:44

53:44

Raj Goyle is running for Comptroller of New York state, and he wants your support. He’s got mine because I think Raj is what America is all about. A first-generation Indian-American, Duke undergrad and Harvard Law grad, Raj was the co-founder of Bodhala, a legal spend analytics and management platform which he and team sold to Onit. As the leader o…

1
Stoic Street Smarts w/ Ed Latimore 1:10:33

2M ago1:10:33

1:10:33

Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed about his new memoir, Hard Lessons From the Hurt Business: Boxing and the Art of Life in which he shares stories about discipline…

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Soul on Fire w/ John O’Leary (Encore episode) 53:51

2M ago53:51

53:51

John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really, really burned, over 100% of his body, 87% of which were third-degree burns. Doctors gave him less than 1% chance of living and told his parents he would…

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Why You Will Never Feel Rich w/ Daniel Crosby 58:11

2M ago58:11

58:11

Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the fun, non-obvious aspects of money and emotions, such as how comparison drives us crazy and why our bias toward action —doing something when things are…

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Why Two Parents Are Better Than One w/ Melissa Kearney (Encore) 42:39

3M ago42:39

42:39

Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised in two-parent homes have better personal and professional outcomes (ON AVERAGE) than those raised in single-parent homes. Specifically, two-parent hom…

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Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark 42:59

3M ago42:59

42:59

If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most urgent challenges. In this week’s episode, Craig and I discuss the early days of Craigslist, its radical “revenue-minimization” str…

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Laughing at Death w/ John Kenney 54:59

3M ago54:59

54:59

What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In this episode, I (i.e., me–Paul–the host) sit down with John Kenney—award-winning author and longtime New Yorker contributor—for a candid and sometimes very funny conversation about writing, d…

1
Rise of Populism w/ Brad Todd 50:40

3M ago50:40

50:40

Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in American politics. From growing up in East Tennessee to advising senators, governors, and big-time campaigns, Brad’s been in the trenches for decades — and he’s got the stories to prove it. Paul a…

1
From Prison to Oprah 58:36

4M ago58:36

58:36

What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New York Times bestselling author? In this unforgettable episode, Paul sits down with Lara Love Hardin, author of The Many Lives of Mama Love, a mind-blowing memoir of crippling dependence, incar…

1
Would you vote for Jesus? 47:05

4M ago47:05

47:05

📬 Subscribe to Paul’s Substack: https://words.paulollinger.com/📖 Learn more about Jonathan Rauch: https://jonathanrauch.typepad.com/What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan Rauch returns to the podcast to talk about his new book 'Cross…

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Tribalism is Dumb (w/Andrew Heaton) 1:07:54

4M ago1:07:54

1:07:54

Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism comes from, how it is tearing us apart, and how we might fix it. With wit, warmth, and some surprisingly deep evolutionary psychology, Andrew explains how our ancient brains are wired to see…

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Puck CEO, Sarah Personette 1:00:50

5M ago1:00:50

1:00:50

This week, Paul sits down with Sarah Personette, CEO of Puck, the fast-growing news outlet the New York Times described as “Vanity Fair for the Substack era.” From her ambition to become a CEO at age seven to her senior roles at Facebook, Universal-McCann, and Twitter – which ended after Elon Musk bought the company, Sarah unpacks what it takes to …

1
Weapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger 1:21:02

5M ago1:21:02

1:21:02

Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who discovered himself after years of addiction and psychedelics only to emerge on the other side as one of the funniest comedians working today and starring in the hit Off Broadway Steven Soderbergh sho…

1
How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman) 51:50

5M ago51:50

51:50

Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize Your Full Potential. Scott’s writing dives deep into the psychology of the victim mindset, narcissism, and the impact of performative vulnerability on social media. Having overcome childhood misdiagno…

1
Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger 45:54

5M ago45:54

45:54

Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blackstone founder Stephen A. Schwarzman. Zibby shares how grief, motherhood, October 7th, and why it’s okay–great even–to marry the tennis pro! She shares how resilience shaped her path, from launching a a…

1
Jeffery Toobin on Presidential Power | Reasonably Happy Podcast 1:00:15

6M ago1:00:15

1:00:15

CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of American presidents. From Trump’s transactional pardons to the controversial case of Hunter Biden, Toobin offers sharp analysis, historical insight, and headline-worthy commentary. He discusses why…

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A Poet’s Wild Past w/ Edward Hirsch 52:30

6M ago52:30

52:30

Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A Stand-Up Comedy and a Skokie Elegy. Hirsch reflects on his chaotic upbringing in 1950s Jewish Chicago, his complicated relationships with his parents, and the wild characters who shaped his l…

1
Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger 54:57

6M ago54:57

54:57

Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing policy scholar—explains why race-based affirmative action has failed America's working class and what can be done to fix it. A self-described “liberal maverick,” Kahlenberg dives into his contr…

1
Facing Down Trump with Jocelyn Benson 46:15

6M ago46:15

46:15

In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this we…

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Paul Wants $$ From Qatar (and other hilarious Substack posts) 27:54

7M ago27:54

27:54

This week, Paul reads his three most recent Substack posts, including: A very funny take on Qatar's bribery of pretty much every institution in America, How his dog's feel about castration, and Why many of us will have our TikTok handles on our tombstones. Please join Paul's Substack family by following here: http://words.paulollinger.com . And, if…

1
From Chaos to Cambridge - Rob Henderson 57:31

7M ago57:31

57:31

He was drinking by age five, shuffled through ten foster homes, and emotionally shut down by the time most kids are starting kindergarten — yet Rob Henderson clawed his way from chaos to Cambridge. In this powerful episode, Rob, author of Troubled: A Memoir of Foster Care, Family, and Social Class, shares his incredible journey from trauma and addi…

1
Mike Reiss: How The Simpsons Changed TV | Reasonably Happy with Paul Ollinger 59:39

7M ago59:39

59:39

The Simpsons writer and showrunner Mike Reiss shares behind-the-scenes secrets from 36+ years on the iconic animated series. From working with comedy legends like Sam Simon, Al Jean, and Conan O'Brien to writing for Johnny Carson and witnessing the wild beginnings of FOX, Mike recounts hilarious Hollywood stories and life lessons from his travels t…

1
Laurie Woolever- Dark Side of Celebrity Chefs 46:07

7M ago46:07

46:07

Former personal assistant to both Anthony Bourdain and Mario Batali, Laurie Woolever, opens up about the untold truths behind celebrity kitchens, toxic food culture, addiction, and what ultimately drove Bourdain to suicide. From Mario Batali’s manipulative power plays to Bourdain’s romantic obsessions and lifelong depression, Woolever shares the un…

1
E.A. Hanks - Famous Father, Troubled Mother 49:33

8M ago49:33

49:33

In this raw and revealing episode of Reasonably Happy, author and screenwriter E.A. Hanks opens up about growing up as the daughter of Tom Hanks, surviving a chaotic childhood with an abusive, mentally ill mother, and forging her own path in Hollywood. From hidden trauma and therapy breakthroughs to the price of fame and writing a memoir about fami…

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Jim Lampley- Boxing, Fame & Fallout | Reasonably Happy with Paul Ollinger 1:13:05

8M ago1:13:05

1:13:05

Legendary sportscaster Jim Lampley joins Paul Ollinger on "Reasonably Happy" to share unforgettable stories from his 40+ year broadcasting career, covering everything from Olympic Games and Super Bowls to boxing icons like Muhammad Ali and Mike Tyson. Lampley reveals the behind-the-scenes drama of his rise at ABC Sports, recounts his emotional conn…

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Jane Borden- Cults Like Us | Reasonably Happy 53:44

8M ago53:44

53:44

In this thought-provoking episode of Reasonably Happy, Paul Ollinger sits down with journalist and author Jane Borden to unpack her explosive new book Cults Like Us: Why Doomsday Thinking Drives America. Together, they explore how apocalyptic beliefs, religious extremism, and cult-like behaviors have shaped American identity—from Puritan roots to m…

1
Life at Fox News w/ Jessica Tarlov | Reasonably Happy with Paul Ollinger 54:01

8M ago54:01

54:01

In this episode of Reasonably Happy, Paul Ollinger sits down with Fox News contributor and Raging Moderates co-host Jessica Tarlov for a wide-ranging conversation on politics, media bias, Israel, parenting, and the chaos of air travel. Jessica opens up about raising two young kids, finding peace in Jamaica, and holding her own as the lone Democrat …

1
Too Woke to Joke w/ Jeff Maurer | Reasonably Happy Podcast 1:02:49

9M ago1:02:49

1:02:49

In this episode of Reasonably Happy, comedian and writer Paul Ollinger sits down with former Last Week Tonight writer Jeff Maurer for a razor-sharp, no-holds-barred conversation on comedy, politics, and the state of liberal discourse. Maurer, now the voice behind the acclaimed Substack I Might Be Wrong, unpacks his journey from speechwriter to Emmy…

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From $0 to $100,000,000: How Anne Mahlum Built a Fitness Empire | Reasonably Happy 1:11:32

9M ago1:11:32

1:11:32

In this episode of Reasonably Happy, host Paul Ollinger sits down with Anne Mahlum, entrepreneur, philanthropist, and founder of Solidcore, the Pilates chain she sold for $100 million. Anne shares her incredible journey from starting a nonprofit running club for the homeless to building a fitness empire with over 100 locations. She dives into overc…

1
Bruce Vilanch: Hollywood Stories | Reasonably Happy 50:22

9M ago50:22

50:22

🎭 Hollywood stories, comedy legends, and the pursuit of happiness! 🎭 In this episode of Reasonably Happy, host Paul Ollinger sits down with the legendary Bruce Vilanch—Emmy-winning writer, comedian, and one of the funniest minds behind Hollywood’s biggest events. Bruce spills the tea on outrageous celebrity encounters, wild award show moments, work…

1
Gretchen Rubin: Happiness Hacks | Reasonably Happy 58:33

9M ago58:33

58:33

Bestselling author Gretchen Rubin joins Reasonably Happy with host Paul Ollinger for a deep dive into happiness, self-improvement, and personal growth. They explore habit formation, the psychology of motivation, the power of self-awareness, and why enjoying the process matters more than the outcome. Gretchen shares insights from The Happiness Proje…

1
Fire Up Your Marriage with Carolyn Sharp | Reasonably Happy 54:17

10M ago54:17

54:17

"Love isn't enough." So says marriage expert Carolyn Sharp in her new book 'Fired Up: Four Secrets to Reigniting Intimacy and Joy in Your Relationship.' Paul talked with Carolyn (a college friend) this week and dove deep into the challenges of modern relationships, the importance of emotional connection, communication, and radical acceptance, and w…

1
Anthony Scaramucci: Success, Failure & the Paradox of Wealth | Reasonably Happy Podcast 35:16

10M ago35:16

35:16

In this candid and insightful episode of Reasonably Happy, host Paul Ollinger sits down with Anthony Scaramucci—founder of SkyBridge Capital, former White House Communications Director, and author of From Wall Street to the White House and Back. Scaramucci shares unfiltered lessons on entrepreneurship, resilience, wealth, and personal growth, refle…

1
Comedian Matt Ruby | Reasonably Happy 56:53

11M ago56:53

56:53

Join Paul as he sits with the very funny Matt Ruby and discuss performing on psychedelic mushrooms, being raised by a bohemian mom who ran around New York City with Alan Ginsberg and more! Links to all things Matt Ruby including his newsletter, specials and more: https://www.mattrubycomedy.com/ Get Paul Ollinger's book Here: "Reasonably Happy: Essa…

1
Nathan Macintosh | Reasonably Happy 57:09

11M ago57:09

57:09

Join hilarious comedian and hater of all things technology Nathan Macintosh as he sits with host Paul Ollinger and discusses his love hate for tech, the overabundance of screens in socoiety and the fear of what AI will do to the world. Watch Nathan's latest 2 specials here: "Money Never Wakes" https://www.youtube.com/watch?v=sQd7kHYiNsQ&t=20s&authu…

1
Paul Shaffer | Reasonably Happy 1:02:43

12M ago1:02:43

1:02:43

Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from his childhood in Thunder Bay to iconic roles on Saturday Night Live and The Blues Brothers. Shaffer sits with host Paul Ollinger and reflects on his early love for music, working alongside comedy greats lik…

1
Deepak Chopra & Dr. John Kaag | Reasonably Happy 52:46

12M ago52:46

52:46

Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside award winning author, professor, writer and speaker Dr, John Kaag. Visit Rebind at https://s.rebind.ai/0PmPOV and use the promo code reasonablyhappy to get 15% off your first Rebind book experience Get Pa…

1
Rickey Smiley: Living with Loss | Reasonably Happy with Paul OIlinger 48:58

1y ago48:58

48:58

Paul sits down with comedian and syndicated radio legend Rickey Smiley and talk about happiness in the face of grief after losing a son to opioid addiction, surviving being shot at point blank range and continuing a life in comedy in the face of tragedy. Check out Rickeys book: "Sideshow: Living with Loss and Moving Forward with Faith" https://www.…

1
Is music meaningless? | Reasonably Happy with Paul Ollinger 56:18

1y ago56:18

56:18

Paul is joined by SNL music director Eli Brueggemann to discuss everything from what landing a gig like Saturday Night Live does for a musician to how quickly a masters level university degree can become outdated because of simple technology. Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollinger…

1
Comedian Mandal was theWorst Student Council President | Reasonably Happy with Paul Ollinger 56:09

1y ago56:09

56:09

Paul sits down with the insanely funny comedian Mandal to discuss his rise, fall and rise again that lead him to be a go to opener for John Mulaney and performing at the world famous Hollywood Bowl. Paul and Mandel dive into the world of stand up comedy and how Mandel finds purpose and happiness and why it is the driving force in all of his artisti…

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I sleep with a blankie | Reasonably Happy with Paul Ollinger 56:17

1y ago56:17

56:17

Paul sits down with lawyer turned comedian Liz Glazer to discuss how a successful lawyer and law professor can find happiness by saying goodbye to a tenured career by pursuing a life in the arts. Follow Reasonably Happy host Paul Ollinger: https://www.instagram.com/paul_ollingerBy Paul Ollinger

1
Start Thinking Rich | Reasonably Happy with Paul Ollinger 57:24

1y ago57:24

57:24

Join us for an insightful conversation with Adrian Brambila and Brad Klontz, authors of "Start Thinking Rich," as we dive deep into the mindset strategies that lead to success. Discover how your background, no matter the challenges, should never hold you back from achieving your goals. Learn practical tips and valuable lessons on how to develop a w…

1
Claiming Confidence | Reasonably Happy with Paul Ollinger 54:05

1y ago54:05

54:05

We are joined by Lydia Fenet, the founder and CEO of the Lydia Fenet Agency, a boutique agency representing best in class charity auctioneers. Lydia is a best selling author and ground breaking art auctioneer who sits with us to talk about art, confidence and how to decide what success means to you. Pick up a copy of "Claim Your Confidence" by Lydi…

1
What Cocaine Taught Me | Reasonably Happy with Paul Ollinger 53:33

1y ago53:33

53:33

We are joined by New York Times best selling author and former Wall Street wild man Turney Duff to discuss Hookers, Blow, Million-dollar bonuses on Wall Street and the journey through recovery and what lies the other side of the Wall Street hustle. Pick up a copy of "The Buy Side" by Turney Duff: https://www.amazon.com/Buy-Side-Street-Traders-Spect…

1
The People Who Never Quit with Henry Oliver 57:40

1+ y ago57:40

57:40

What did Ray Kroc, Maya Angelou, Margaret Thatcher, and Malcolm X all have in common? (Don’t worry - this isn’t a dirty joke!) They were all opsimaths, i.e. a person who blooms late in life. In his new book SECOND ACT: What Late Bloomers Can Tell You About Success and Reinventing Your Life, author Henry Oliver shares the stories of well-known peopl…