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PODCAST

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. words.paulollinger.com

comedy

All Episodes

64:01

Surviving the Loss of a Child

Reasonably Happy with Paul Ollinger ·

2026/04/16

“How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned him a Peabody Award, a WGA Award, and two Emmy nominations. He made his off-Broadway debut in Sorry For Your Loss, a raw, comedic, and deeply vulnerable one-man show about coping with a parent’s worst fear, the loss of a

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66:04

Millionaires v. Billionaires in NYC

Reasonably Happy with Paul Ollinger ·

2026/04/02

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 glamorous Manhattan apartment building where the lives of the ultra-wealthy residents intersect with the man who quietly watches it all—the doorman. Over the course of one explosive day, secrets, class tensions, and personal betrayals collide in a fast-moving plot that doubles as sharp social satire about modern New York and the divides of race,

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61:25

The Beatles, Ted Turner, and Ric Flair with Steve...

Reasonably Happy with Paul Ollinger ·

2026/03/26

This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with some of the biggest brands and celebrities in entertainment history. I originally wanted to talk to Steve because of his experience leading the go-to-market plan of The Beatles Anthology, one of the most commercially successful recording projects of all-time. It was to be the follow-up episode to last week’s interview with Peter Doggett, author of 'You

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58:00

Money, Fame, and Misery: Meet the Beatles

Reasonably Happy with Paul Ollinger ·

2026/03/19

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 money than they ever could have imagined. So why were these four young men so miserable? (And often short of cash!) My guest today is Peter Doggett—one of the great rock music writers of our time, and a man who has spent decades studying what happens when ambition, fame, and enormous piles of cash—and drugs—collide. Peter is the author of You Never Give

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58:30

Believe and You Will See! (w/ Nir Eyal )

Reasonably Happy with Paul Ollinger ·

2026/03/12

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 he published his latest - Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Extraordinary Results. In our chat, Nir and I discuss:Why beliefs can help us perform at our top potential (or vice versa) The difference between facts, faith, and belief How beliefs can benefit us, even if they’re not “true” The importance of

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61:26

Gina Gershon on Fame, Desire, and Boobs

Reasonably Happy with Paul Ollinger ·

2026/03/05

Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing disruptor of polite expectations. You know Gina from unforgettable roles in Bound, Showgirls, Face/Off, Cocktail, and a career that has zig-zagged fearlessly between Hollywood glamor, indie grit, Broadway, and music. We talked about her work and life as recounted in her new memoir, 'Alpha Pussy: How I Survived the Valley and Learned to Love My Boobs’ (a

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59:02

The Courage to Be Right w/ Matt Kaplan

Reasonably Happy with Paul Ollinger ·

2026/02/26

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 Imprisoned for Being Right in which he shares the stories of researchers—from Darwin to Pasteur to modern Nobel Prize winners—who had to fight for their revolutionary ideas to be accepted. "But Paul…” you might say. "This sounds very interesting, but how does it fit into the conversations here on Reasonably Happy?” Good question! It’s because I like

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74:36

Insider Trading w/Tom Hardin

Reasonably Happy with Paul Ollinger ·

2026/02/19

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 Securities Fraud and Conspiracy to Commit Securities Fraud, which are felonies. In 2008, during the beginning of the great finanical crisis, Tom desperately needed to put some points on the board at his fund. And since everybody else in the industry seemed to be doing it, Tom allowed himself to trade equities on material, non-public information—something he

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50:44

Surviving Middle Age w/ Ben Markovits

Reasonably Happy with Paul Ollinger ·

2026/02/12

Ben Markovits is the author of several acclaimed novels, including his most recent release The Rest of Our Lives, which explores marriage, infidelity, empty nesting, and mortality. The book, which was short-listed for the Booker Prize, focuses on a 55-year-old law professor’s midlife crisis and transformative road trip after his children leave home. You might say it examines the sources of happiness in our lives as we age. Ben’s writing has appeared in The New York Times, The New Yorker, and The

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42:31

Marriage, Infidelity, and Millennial Disillusionment...

Reasonably Happy with Paul Ollinger ·

2026/02/05

Erin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicating” and W praised the book for its “sometimes mocking examination of young middle age.” I wanted to speak with Erin because her characters reflect a sense of grown-up melancholy arising when goals like home ownership, careers, and parenthood don’t provide the fulfillment that was expected of them. So what do we do, she asks implicitly, when we find

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44:01

A.I. Facts, Fears and Fiction (w/ Bryan Reimer)

Reasonably Happy with Paul Ollinger ·

2026/01/28

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-author of the new book ‘How to Make AI Useful’ in which he explores AI’s power and potential to change the world. He and I sat down this week to discuss the facts, fears, and fiction around what might be the most transformational innovation of our lifetimes. Brian offers a grounded, human-centered perspective on how AI is evolving—and why most of the extreme

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60:23

From Apartheid to Atlanta w/ Robyn Curnow

Reasonably Happy with Paul Ollinger ·

2026/01/15

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 Desk with Robyn Curnow. Prior to that, she served as the network’s Africa correspondent out of Johannesburg and covered Europe out of CNN’s London Bureau.If you don’t recognize her name, I bet you’ll recognize her distinctive voice because you likely saw her interviews with some of the most prominent people of our lifetimes, including Nelson Mandela,

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72:11

Rewrite Mental Illness w/Laura Delano

Reasonably Happy with Paul Ollinger ·

2026/01/07

Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which was not something openly discussed at the time in her wealthy hometown of Greenwich, CT. Over the next 14 years, Laura was diagnosed with bipolar disorder, depression, social anxiety disorder, eating disorder, poly-substance dependence, and borderline personality disorder. These conditions earned her prescriptions for Seroquel, Abilify,

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86:17

Find your Essential Intent w/ Greg McKeown

Reasonably Happy with Paul Ollinger ·

2025/12/18

Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions for 2026, Greg’s insights will be a great way to think through WHAT REALLY MATTERS to you. To demonstrate how challenging this seemingly obvious exercise can be, I asked Greg how to help me focus my sincere but varied slate of professional ambitions. It gets a little uncomfortable, but that’s the point! And if you get one thing out of this

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40:41

High Net Worth Divorce with Laura Wasser

Reasonably Happy with Paul Ollinger ·

2025/12/03

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 attorney” might conjure up images of a rapacious shark in Prada boots squeezing every dollar out of her clients’ exes, Laura preaches the gospel of divorce with

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56:00

Surviving the College Application Process w/ Jeffrey...

Reasonably Happy with Paul Ollinger ·

2025/11/19

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 research and a survey of 3,000 parents to give families permission to think more broadly about what signals a “good” college for their child, Jeff outlines

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44:04

Paul’s Insights into NYC, Email, and Estate Planning

Reasonably Happy with Paul Ollinger ·

2025/11/12

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 general and some political stuff also. I put the political ones at the end, so you don’t have to involve yourself in that, if you don’t want to. But please

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64:49

Confronting Mortality with Thad Reichley

Reasonably Happy with Paul Ollinger ·

2025/11/05

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 with stage 4 metastatic melanoma. There is no known cure for the disease. A father, husband, educator, and pro-level endurance athlete, Thad’s “job” over the

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57:32

Walking Away from Fame and Money with Rachel Heck

Reasonably Happy with Paul Ollinger ·

2025/10/29

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 decided that a life on the road and in the spotlight wasn’t for her. Instead, she earned and accepted her commission as an officer in the U.S. Air Force

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52:44

Family, Politics & The American Dream with Raj Goyle...

Reasonably Happy with Paul Ollinger ·

2025/10/22

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 of Phone Free New York, Raj led a bi-partisan effort to get phones out of the classroom across New York state. And now he wants to take his immense talent

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322 results

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