Reasonably Happy with Paul Ollinger (Video Edition)
Episodes
Millionaires v. Billionaires in NYC
02 Apr 2026
Contributed by Lukas
Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a...
The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain
26 Mar 2026
Contributed by Lukas
This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with...
Money, Fame, and Misery: Meet the Beatles
19 Mar 2026
Contributed by Lukas
Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett )In the late ‘60s, The Beatles had it all: worldwide fame, critical admiration, and more...
Believe and You Will See! (w/ Nir Eyal )
12 Mar 2026
Contributed by Lukas
My guest this week is Nir Eyal, whose two books ('Hooked’ and ‘Indistractable’) have sold over 1 million copies in over 30 languages. This week ...
Gina Gershon on Fame, Desire, and Boobs
05 Mar 2026
Contributed by Lukas
Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing di...
The Courage to Be Right w/ Matt Kaplan
26 Feb 2026
Contributed by Lukas
Matt Kaplan is a science correspondent at the Economist and author of the new book I Told You So!: Scientists Who Were Ridiculed, Exiled, and Impr...
Insider Trading w/Tom Hardin
19 Feb 2026
Contributed by Lukas
How do you handle it when you screw up badly? (Like really badly.) Former hedge fund trader and Wharton graduate Tom Hardin was convicted of Securiti...
Surviving Middle Age w/ Ben Markovits
12 Feb 2026
Contributed by Lukas
Ben Markovits is the author of several acclaimed novels, including his most recent release The Rest of Our Lives, which explores marriage, infidelity...
Marriage, Infidelity, and Millennial Disillusionment with Erin Somers
05 Feb 2026
Contributed by Lukas
Erin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicati...
A.I. Facts, Fears and Fiction (w/ Bryan Reimer)
28 Jan 2026
Contributed by Lukas
AI will have at least as big an effect on society as the invention of electricity. That’s the prediction of MIT’s Bryan Reimer. Bryan is the co-au...
From Apartheid to Atlanta w/ Robyn Curnow
15 Jan 2026
Contributed by Lukas
My guest is Robyn Curnow, a native South African who spent over two decades at CNN, where she hosted CNN’s Newsroom, and anchored The International ...
Rewrite Mental Illness w/Laura Delano
07 Jan 2026
Contributed by Lukas
Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychia...
Find your Essential Intent w/ Greg McKeown
18 Dec 2025
Contributed by Lukas
Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and...
High Net Worth Divorce with Laura Wasser
03 Dec 2025
Contributed by Lukas
People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedi...
Surviving the College Application Process w/ Jeffrey Selingo
19 Nov 2025
Contributed by Lukas
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...
Paul’s Insights into NYC, Email, and Estate Planning
12 Nov 2025
Contributed by Lukas
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, w...
Confronting Mortality with Thad Reichley
05 Nov 2025
Contributed by Lukas
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...
Walking Away from Fame and Money with Rachel Heck
29 Oct 2025
Contributed by Lukas
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...
Family, Politics & The American Dream with Raj Goyle | Reasonably Happy
22 Oct 2025
Contributed by Lukas
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...
Stoic Street Smarts w/ Ed Latimore
15 Oct 2025
Contributed by Lukas
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 b...
Soul on Fire w/ John O’Leary (Encore episode)
08 Oct 2025
Contributed by Lukas
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 ol...
Why You Will Never Feel Rich w/ Daniel Crosby
01 Oct 2025
Contributed by Lukas
Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: ...
Why Two Parents Are Better Than One w/ Melissa Kearney (Encore)
24 Sep 2025
Contributed by Lukas
Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the po...
Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark
17 Sep 2025
Contributed by Lukas
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...
Laughing at Death w/ John Kenney
10 Sep 2025
Contributed by Lukas
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 Call...
Rise of Populism w/ Brad Todd
03 Sep 2025
Contributed by Lukas
Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happeni...
From Prison to Oprah
20 Aug 2025
Contributed by Lukas
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 fou...
Would you vote for Jesus?
15 Aug 2025
Contributed by Lukas
📬 Subscribe to Paul’s Substack: https://words.paulollinger.com/ 📖 Learn more about Jonathan Rauch: https://jonathanrauch.typepad.com/ What ha...
Tribalism is Dumb (w/Andrew Heaton)
30 Jul 2025
Contributed by Lukas
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 ...
Puck CEO, Sarah Personette
16 Jul 2025
Contributed by Lukas
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 Subs...
Weapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger
06 Jul 2025
Contributed by Lukas
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...
How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman)
02 Jul 2025
Contributed by Lukas
Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize ...
Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger
30 Jun 2025
Contributed by Lukas
Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blacks...
Jeffery Toobin Exposes Presidential Power | Reasonably Happy Podcast
18 Jun 2025
Contributed by Lukas
CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true characte...
A Poet’s Wild Past w/ Edward Hirsch
11 Jun 2025
Contributed by Lukas
Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in P...
Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger
05 Jun 2025
Contributed by Lukas
Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education an...
Facing Down Trump with Jocelyn Benson
30 May 2025
Contributed by Lukas
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 o...
Paul Wants $$ From Qatar (and other hilarious Substack posts)
23 May 2025
Contributed by Lukas
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 A...
From Chaos to Cambridge
14 May 2025
Contributed by Lukas
Rob Henderson’s dad walked out when Rob was an infant. Not long after, Rob’s drug-addicted mother placed him into the foster care system and a nea...
From Chaos to Cambridge - Rob Henderson
14 May 2025
Contributed by Lukas
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 ...
Mike Reiss: How The Simpsons Changed TV | Reasonably Happy with Paul Ollinger
07 May 2025
Contributed by Lukas
The Simpsons writer and showrunner Mike Reiss shares behind-the-scenes secrets from 36+ years on the iconic animated series. From working with comedy ...
Laurie Woolever- Dark Side of Celebrity Chefs
30 Apr 2025
Contributed by Lukas
Former personal assistant to both Anthony Bourdain and Mario Batali, Laurie Woolever, opens up about the untold truths behind celebrity kitchens, toxi...
E.A. Hanks - Famous Father, Troubled Mother
23 Apr 2025
Contributed by Lukas
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, surv...
Jim Lampley- Boxing, Fame & Fallout | Reasonably Happy with Paul Ollinger
16 Apr 2025
Contributed by Lukas
Legendary sportscaster Jim Lampley joins Paul Ollinger on "Reasonably Happy" to share unforgettable stories from his 40+ year broadcasting career, cov...
Jane Borden- Cults Like Us | Reasonably Happy
09 Apr 2025
Contributed by Lukas
In this thought-provoking episode of Reasonably Happy, Paul Ollinger sits down with journalist and author Jane Borden to unpack her explosive new book...
Life at Fox News w/ Jessica Tarlov | Reasonably Happy with Paul Ollinger
02 Apr 2025
Contributed by Lukas
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 ...
Too Woke to Joke w/ Jeff Maurer | Reasonably Happy Podcast
26 Mar 2025
Contributed by Lukas
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, n...
From $0 to $100,000,000: How Anne Mahlum Built a Fitness Empire | Reasonably Happy
19 Mar 2025
Contributed by Lukas
In this episode of Reasonably Happy, host Paul Ollinger sits down with Anne Mahlum, entrepreneur, philanthropist, and founder of Solidcore, the Pilate...
Bruce Vilanch: Hollywood Stories | Reasonably Happy
12 Mar 2025
Contributed by Lukas
🎭 Hollywood stories, comedy legends, and the pursuit of happiness! 🎭 In this episode of Reasonably Happy, host Paul Ollinger sits down with the ...
Gretchen Rubin: Happiness Hacks | Reasonably Happy
03 Mar 2025
Contributed by Lukas
Bestselling author Gretchen Rubin joins Reasonably Happy with host Paul Ollinger for a deep dive into happiness, self-improvement, and personal growth...
Fire Up Your Marriage with Carolyn Sharp | Reasonably Happy
12 Feb 2025
Contributed by Lukas
"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...
Anthony Scaramucci: Success, Failure & the Paradox of Wealth | Reasonably Happy Podcast
05 Feb 2025
Contributed by Lukas
In this candid and insightful episode of Reasonably Happy, host Paul Ollinger sits down with Anthony Scaramucci—founder of SkyBridge Capital, former...
Comedian Matt Ruby | Reasonably Happy
15 Jan 2025
Contributed by Lukas
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 ...
Nathan Macintosh | Reasonably Happy
01 Jan 2025
Contributed by Lukas
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, t...
Paul Shaffer | Reasonably Happy
18 Dec 2024
Contributed by Lukas
Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from hi...
Deepak Chopra & Dr. John Kaag | Reasonably Happy
11 Dec 2024
Contributed by Lukas
Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside awar...
Rickey Smiley: Living with Loss | Reasonably Happy with Paul OIlinger
04 Dec 2024
Contributed by Lukas
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 addi...
Is music meaningless? | Reasonably Happy with Paul Ollinger
27 Nov 2024
Contributed by Lukas
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...
Comedian Mandal was theWorst Student Council President | Reasonably Happy with Paul Ollinger
20 Nov 2024
Contributed by Lukas
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 an...
I sleep with a blankie | Reasonably Happy with Paul Ollinger
13 Nov 2024
Contributed by Lukas
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 t...
Start Thinking Rich | Reasonably Happy with Paul Ollinger
30 Oct 2024
Contributed by Lukas
Join us for an insightful conversation with Adrian Brambila and Brad Klontz, authors of "Start Thinking Rich," as we dive deep into the mindset strate...
Your Free My Book!
29 Oct 2024
Contributed by Lukas
Dear Premium Subscriber of Reasonably Happy Substack!I write today to request your snail mail address so’s I may send you a copy of my newly-publish...
Claiming Confidence | Reasonably Happy with Paul Ollinger
23 Oct 2024
Contributed by Lukas
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 i...
What Cocaine Taught Me | Reasonably Happy with Paul Ollinger
16 Oct 2024
Contributed by Lukas
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 Wa...
The Reason Ozempic Works
26 Sep 2024
Contributed by Lukas
Six months ago, I bumped into my friend Bill. Bill’s a big dude in his early 60s who has the frame of a guy who might have played offensive line for...
The People Who Never Quit with Henry Oliver
27 Aug 2024
Contributed by Lukas
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 opsim...
A Poet’s Life (with In-Q)
21 Aug 2024
Contributed by Lukas
Nobody gets into poetry for fame and fortune. And yet, there might be a tiny bit of each happening for In-Q, my guest this week who is a renowned poe...
“Second Class” Americans with Batya Ungar-Sargon
14 Aug 2024
Contributed by Lukas
The spirit of the working class is crushed. So argues Batya Ungar-Sargon in her new book 'Second Class: How the Elites Betrayed America's Working Men ...
Why the News is Bad with Angus Hervey
07 Aug 2024
Contributed by Lukas
**Hi friends - this is Paul writing to confess to an error in my introduction in this week's episode. The name of Angus Hervey's podcast is "Hope Is a...
Fighting for the Family Business with Stephanie Stuckey
04 Aug 2024
Contributed by Lukas
Stephanie Stuckey used her life’s savings to buy the company that is her family’s legacy. At it’s height in the1960’s and 70’s, there were ...
Persevering Through Grief with Nicole Avant
24 Jul 2024
Contributed by Lukas
Nicole Avant is the former U.S. Ambassador to the Bahamas and author of a new memoir, 'Think You’ll Be Happy: Moving through Grief with Grit, Grace,...
On The Move
03 Jul 2024
Contributed by Lukas
On this introspective episode of Crazy Money, Paul sits alone in his empty Atlanta house and talks openly about the thoughts and feelings that drew hi...
Who killed Rudolf Diesel? (with Doug Brunt)
12 Jun 2024
Contributed by Lukas
Yes, there was actually a guy named Rudolf Diesel who actually invented the diesel engine, which was incredibly revolutionary for its time. It earned ...
Restoring Politcal Sanity with Charlie Wheelan (Encore)
04 Jun 2024
Contributed by Lukas
Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Econo...
Mike Posner on Life Beyond Fame and Fortune
28 May 2024
Contributed by Lukas
Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays ...
Andrew Yang on Our Broken Political System (Encore)
21 May 2024
Contributed by Lukas
Andrew Yang is a former Presidential and NYC mayoral candidate and the founder of Venture for America. He's also the founder of the Forward Party wh...
The Third Path with Jordan Harbinger
14 May 2024
Contributed by Lukas
Jordan Harbinger is one of the most popular podcasters in North America, but it all started by accident. As a young University of Michigan grad, Jord...
Living The Constitution with AJ Jacobs
07 May 2024
Contributed by Lukas
Good morrow, chum! My guest this week is A.J. Jacobs, author of the new / amazing book 'The Year of Living Constitutionally: One Man’s Humble Quest ...
Being Human at Work with Kim Scott, author of 'Radical Candor’
30 Apr 2024
Contributed by Lukas
‘Radical Candor’ author Kim Scott once had to inform a colleague that they smelled bad….like, really bad. She was able to do so becuase she had ...
Power Couple: Debbi “Mrs.” Fields and Wade Shealy
24 Apr 2024
Contributed by Lukas
Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his...
Death, Dying, and Israel with Rabbi Steve Leder
16 Apr 2024
Contributed by Lukas
Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times b...
The Wealth Money Can’t Buy with Robin Sharma
09 Apr 2024
Contributed by Lukas
Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, ...
America’s Government Teacher, Sharon McMahon
04 Apr 2024
Contributed by Lukas
Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding h...
Poor Kid Makes Millions Trading, Fights Inequality with Gary Stevenson
29 Mar 2024
Contributed by Lukas
Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances)...
The Narcissist Next-door with Dr. Ramani Durvasula
20 Mar 2024
Contributed by Lukas
Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissisti...
TED's Chris Anderson on Infectious Generosity
14 Mar 2024
Contributed by Lukas
Chris Anderson is the Head Curator of TED and author of the new book, 'Infectious Generosity: The Ultimate Idea Worth Spreading' in which he argues t...
Mike and Paul’s Road Trip
05 Mar 2024
Contributed by Lukas
This episode is highlights of a conversation between Paul and Mike Carano, long-time friend and Crazy Money editor. It was recorded on a road trip b...
On Fire for Life with John O’Leary
28 Feb 2024
Contributed by Lukas
When John O’Leary was 9 years old, he played with fire and got burned. Like really, really burned, over 99% of his body. Doctors gave him less than ...
Paul Reads Money Essays
21 Feb 2024
Contributed by Lukas
In this special “where has Paul been?” episode, Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, so that yo...
Race and Money with Coleman Hughes (Encore)
06 Feb 2024
Contributed by Lukas
Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.”...
The Joys and Anxieties of Wealth (Encore)
28 Dec 2023
Contributed by Lukas
Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of Boston ...
Dr. Drew Pinsky on Careers, Money, and Fame (Encore)
27 Dec 2023
Contributed by Lukas
This is a special holiday encore of the 2nd episode of Crazy Money with Dr. Drew, which ran Jan 30, 2019. Dr. Drew offers candid insight into the ups ...
How to Live a Stress-free Financial Life with Jared Dillian
19 Dec 2023
Contributed by Lukas
Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on ...
Judd Apatow on Money, Fame, and Adam Sandler (Encore)
13 Dec 2023
Contributed by Lukas
Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to ma...
Author Gary Sernovitz
05 Dec 2023
Contributed by Lukas
Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’...
How to Get Un-stuck with Merrick Furst, Ph.D.
29 Nov 2023
Contributed by Lukas
Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you fin...
Paul Reads His Thanksgiving Essays
21 Nov 2023
Contributed by Lukas
In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of L...
Ed Begley Jr. on Finding Serenity in Hollywood
15 Nov 2023
Contributed by Lukas
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ 🎤 See Paul’s upcoming comedy dates here and random tho...
Pushing Our Kids Too Hard: On Toxic Achievement Culture with Jennifer Wallace
08 Nov 2023
Contributed by Lukas
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ Jennifer Wallace is a journalist and author specializing in ...
Lessons from an '80s Guitar god with Rik Emmett of Triumph
31 Oct 2023
Contributed by Lukas
Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the Unit...