Shows / Reasonably Happy with Paul Ollinger
Reasonably Happy with Paul Ollinger
Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection.
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Episodes
Reasonably Happy with Paul OllingerA Poet’s Wild Past w/ Edward Hirsch
Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A…
Reasonably Happy with Paul OllingerHas Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger
Has affirmative action failed in America?? In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing…
Reasonably Happy with Paul OllingerFacing Down Trump with Jocelyn Benson
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…
Reasonably Happy with Paul OllingerPaul Wants $$ From Qatar (and other hilarious Substack posts)
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…
Reasonably Happy with Paul OllingerFrom Chaos to Cambridge
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 near-constant…
Reasonably Happy with Paul OllingerFrom Chaos to Cambridge - Rob Henderson
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…
Reasonably Happy with Paul OllingerMike Reiss: How The Simpsons Changed TV | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerLaurie Woolever- Dark Side of Celebrity Chefs
Former personal assistant to both Anthony Bourdain and Mario Batali, Laurie Woolever, opens up about the untold truths behind celebrity kitchens, toxic food…
Reasonably Happy with Paul OllingerE.A. Hanks - Famous Father, Troubled Mother
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…
Reasonably Happy with Paul OllingerJim Lampley- Boxing, Fame & Fallout | Reasonably Happy with Paul Ollinger
Legendary sportscaster Jim Lampley joins Paul Ollinger on "Reasonably Happy" to share unforgettable stories from his 40+ year broadcasting career, covering…
Reasonably Happy with Paul OllingerJane Borden- Cults Like Us | Reasonably Happy
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…
Reasonably Happy with Paul OllingerLife at Fox News w/ Jessica Tarlov | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerToo Woke to Joke w/ Jeff Maurer | Reasonably Happy Podcast
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…
Reasonably Happy with Paul OllingerFrom $0 to $100,000,000: How Anne Mahlum Built a Fitness Empire | Reasonably Happy
In this episode of Reasonably Happy, host Paul Ollinger sits down with Anne Mahlum, entrepreneur, philanthropist, and founder of Solidcore, the Pilates chain…
Reasonably Happy with Paul OllingerBruce Vilanch: Hollywood Stories | Reasonably Happy
🎭 Hollywood stories, comedy legends, and the pursuit of happiness! 🎭 In this episode of Reasonably Happy, host Paul Ollinger sits down with the legendary Bruce…
Reasonably Happy with Paul OllingerGretchen Rubin: Happiness Hacks | Reasonably Happy
Bestselling author Gretchen Rubin joins Reasonably Happy with host Paul Ollinger for a deep dive into happiness, self-improvement, and personal growth. They…
Reasonably Happy with Paul OllingerFire Up Your Marriage with Carolyn Sharp | Reasonably Happy
"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…
Reasonably Happy with Paul OllingerAnthony Scaramucci: Success, Failure & the Paradox of Wealth | Reasonably Happy Podcast
In this candid and insightful episode of Reasonably Happy, host Paul Ollinger sits down with Anthony Scaramucci—founder of SkyBridge Capital, former White…
Reasonably Happy with Paul OllingerComedian Matt Ruby | Reasonably Happy
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…
Reasonably Happy with Paul OllingerNathan Macintosh | Reasonably Happy
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…
Reasonably Happy with Paul OllingerPaul Shaffer | Reasonably Happy
Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from his childhood…
Reasonably Happy with Paul OllingerDeepak Chopra & Dr. John Kaag | Reasonably Happy
Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside award winning…
Reasonably Happy with Paul OllingerRickey Smiley: Living with Loss | Reasonably Happy with Paul OIlinger
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…
Reasonably Happy with Paul OllingerIs music meaningless? | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerComedian Mandal was theWorst Student Council President | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerI sleep with a blankie | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerStart Thinking Rich | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerClaiming Confidence | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerWhat Cocaine Taught Me | Reasonably Happy with Paul Ollinger
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…
Reasonably Happy with Paul OllingerThe People Who Never Quit with Henry Oliver
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…
Reasonably Happy with Paul OllingerA Poet’s Life (with In-Q)
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 poet and…
Reasonably Happy with Paul Ollinger“Second Class” Americans with Batya Ungar-Sargon
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 and…
Reasonably Happy with Paul OllingerWhy the News is Bad with Angus Hervey
**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 Verb,"…
Reasonably Happy with Paul OllingerFighting for the Family Business with Stephanie Stuckey
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 hundreds of…
Reasonably Happy with Paul OllingerPersevering Through Grief with Nicole Avant
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, and…
Reasonably Happy with Paul OllingerOn The Move
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 him back to…
Reasonably Happy with Paul OllingerWho killed Rudolf Diesel? (with Doug Brunt)
Yes, there was actually a guy named Rudolf Diesel who actually invented the diesel engine, which was incredibly revolutionary for its time. It earned Diesel a…
Reasonably Happy with Paul OllingerRestoring Politcal Sanity with Charlie Wheelan (Encore)
Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no…
Reasonably Happy with Paul OllingerMike Posner on Life Beyond Fame and Fortune
Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays and his…
Reasonably Happy with Paul OllingerAndrew Yang on Our Broken Political System (Encore)
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 where he…
Reasonably Happy with Paul OllingerThe Third Path with Jordan Harbinger
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, Jordan decided…
Reasonably Happy with Paul OllingerLiving The Constitution with AJ Jacobs
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 to Follow…
Reasonably Happy with Paul OllingerBeing Human at Work with Kim Scott, author of 'Radical Candor’
‘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 created on her…
Reasonably Happy with Paul OllingerPower Couple: Debbi “Mrs.” Fields and Wade Shealy
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 start…
Reasonably Happy with Paul OllingerDeath, Dying, and Israel with Rabbi Steve Leder
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…
Reasonably Happy with Paul OllingerThe Wealth Money Can’t Buy with Robin Sharma
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, The Monk…
Reasonably Happy with Paul OllingerAmerica’s Government Teacher, Sharon McMahon
Sharon McMahon is living her purpose. Via her wildly popular Instagram account @SharonSaysSo, she is fighting political misinformation and guiding her audience…
Reasonably Happy with Paul OllingerPoor Kid Makes Millions Trading, Fights Inequality with Gary Stevenson
Gary Stevenson grew up in tough, working class East London. Despite setbacks in high school (having to do with the distribution of illicit substances), his…
Reasonably Happy with Paul OllingerThe Narcissist Next-door with Dr. Ramani Durvasula
Dr. Ramani Durvasula is a clinical psychologist and author of the New York Times best-seller It’s Not You: Identifying and Healing from Narcissistic People. In…
Reasonably Happy with Paul OllingerTED's Chris Anderson on Infectious Generosity
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 that YOU…
Reasonably Happy with Paul OllingerMike and Paul’s Road Trip
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 between San…
Reasonably Happy with Paul OllingerOn Fire for Life with John O’Leary
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 1% chance…
Reasonably Happy with Paul OllingerPaul Reads Money Essays
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 you can drive…
Reasonably Happy with Paul OllingerRace and Money with Coleman Hughes (Encore)
Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.” Coleman has a…
Reasonably Happy with Paul OllingerThe Joys and Anxieties of Wealth (Encore)
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…
Reasonably Happy with Paul OllingerDr. Drew Pinsky on Careers, Money, and Fame (Encore)
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 and downs…
Reasonably Happy with Paul OllingerHow to Live a Stress-free Financial Life with Jared Dillian
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 the little…
Reasonably Happy with Paul OllingerJudd Apatow on Money, Fame, and Adam Sandler (Encore)
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 material…
Reasonably Happy with Paul OllingerAuthor Gary Sernovitz
Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief…
Reasonably Happy with Paul OllingerHow to Get Un-stuck with Merrick Furst, Ph.D.
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 find yourself…