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

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

Author: Paul Ollinger October 22, 2025 Duration: 52:00
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 and experience to Albany for the most important position (Comptroller!) you’ve never thought about. As you’ll hear, there’s plenty that Raj and I disagree about. But he’s the kind of person we need more of in government: a smart, driven leader who wants to make government work for citizens. Among lots of other things, Raj and I discuss:
-Zohran Mamdani, the NYC mayoral candidate whom Raj supports and I DO NOT
-What a comptroller does
-Money, happiness, and public service
-What it was like for his parents–both doctors–to emigrate to the U.S.
-How Jimmy Carter helped shaped his belief in ethical capitalism and an accountable government
AI’s impact on the economy and what we can do about it

✍️Please rate my podcast (https://ratethispodcast.com/paulopod) ✍️
🗳️Learn more about Raj (https://rajgoyle.com/) 🗳️
👊Get Paul’s Substack newsletter (http://words.paulollinger.com) 👊

Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

Reasonably Happy with Paul Ollinger
Podcast Episodes
The Richest Family You've Never Heard Of [not-audio_url] [/not-audio_url]

Duration: 52:14
Investment management firm Fidelity is a private company that administers over $18 trillion in assets—that’s greater than the GDPs of Germany, Japan, the United Kingdom, and France combined. (Or, it’s18 Elon Musks.) Last…
W. Kamau Bell on Cosby, Comedy, and Father's Day [not-audio_url] [/not-audio_url]

Duration: 27:50
I was most pleased to speak this afternoon with W. Kamau Bell, a Peabody Award and 4-time Emmy-winning comedian, filmmaker, and television host who is also a Celebrity Jeopardy champion!He is best known as the creator an…
5 Questions with Bruce Feiler [not-audio_url] [/not-audio_url]

Duration: 36:48
Thanks very much to Bruce Feiler for joining me on the 5 Questions livestream to discuss his new book A Time to Gather: How Ritual Created the World—and How it Can Save Us.In this upbeat and positive conversation, Bruce…
5 Questions with Andy Borowitz [not-audio_url] [/not-audio_url]

Duration: 31:13
On this third episode of 5 Questions, I speak with Andy Borowitz, whose massively popular newsletter The Borowitz Report tops out around 200 words per post. So this intro is going to be brief!Even if you belong to Andy’s…
A Political Family Black Sheep Tells All (with Rosebud Baker) [not-audio_url] [/not-audio_url]

Duration: 50:23
My guest today is Rosebud Baker. Rosebud is one of the sharpest and most honest voices in comedy today. She’s an Emmy-nominated and Writers Guild Award-winning writer whose credits include Saturday Night Live, Inside Amy…
5 Questions with A.J. Jacobs [not-audio_url] [/not-audio_url]

Duration: 32:17
✍️ Follow Paul Ollinger on Substack by clicking here ✍️A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a great choice to be my sec…
I Read My Essays to You [not-audio_url] [/not-audio_url]

Duration: 35:59
✍️ Follow Paul Ollinger on Substack by clicking here ✍️Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack over the past six months. They cover the Manosphere, schadenfreu…
5 Questions with Dave Barry [not-audio_url] [/not-audio_url]

Duration: 30:52
✍️ Follow Paul Ollinger on Substack by clicking here ✍️Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack interview show that I’ll be…
Gretchen Rubin Will Teach You to be Happy [not-audio_url] [/not-audio_url]

Duration: 58:34
✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Happiness is a choice that requires effort at times.” -Aeschylus Whenever I go back and re-listen to one of my podcast interviews, I always discover elements of the…