How to Live a Stress-free Financial Life with Jared Dillian

How to Live a Stress-free Financial Life with Jared Dillian

Author: Paul Ollinger December 19, 2023 Duration: 1:00:00
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 things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like your house, your car, and how much you pay for college, makes all the difference. A renowned investment strategist and author, Jared is widely recognized for his keen insights into market psychology and his ability to explain complex financial concepts in an accessible manner. He is also the author of the acclaimed book 'Street Freak: Money and Madness at Lehman Brothers' and the editor of the popular financial newsletter 'The Daily Dirtnap', where he shares his valuable perspective on the markets. Pre-order his new book, ’No Worries: How to Live a Stress-Free Financial Life’ here. On this week’s episode, we discuss:


Striking the balance between being a cheap f*ck and a high roller.

Why renting is often a much better idea than buying a home.

How much student debt is okay.

The five asset classes you should own in “The Awesome Portfolio"


Jared also graciously shares insights into his bipolar disorder and the side effects of the meds he takes. In so doing, he continues to help de-stigmatize mental illness. And for that, I thank him.

See Paul live in comedy mode:

Austin, Jan 11 - Buy Tickets Here


San Francisco, Feb 22 -  Buy Tickets Here


Nashville, Feb 28 - Buy Tickets Here 


🔥Learn and laugh by reading Paul’s Substack here. 🔥
🚀 Follow Paul on Instagram here. 🚀

DISCLAIMER: This episode contains a discussion of investment strategies and theories but in no way should be considered personal financial advice. Investing in any of the asset classes mentioned can result in material losses.

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: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
Stoic Street Smarts w/ Ed Latimore [not-audio_url] [/not-audio_url]

Duration: 1:08:48
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…
Soul on Fire w/ John O’Leary (Encore episode) [not-audio_url] [/not-audio_url]

Duration: 52:07
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 10…
Why You Will Never Feel Rich w/ Daniel Crosby [not-audio_url] [/not-audio_url]

Duration: 56:27
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 asp…
Why Two Parents Are Better Than One w/ Melissa Kearney (Encore) [not-audio_url] [/not-audio_url]

Duration: 40:55
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…
Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark [not-audio_url] [/not-audio_url]

Duration: 41:15
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 u…
Laughing at Death w/ John Kenney [not-audio_url] [/not-audio_url]

Duration: 53:15
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 K…
Rise of Populism w/ Brad Todd [not-audio_url] [/not-audio_url]

Duration: 48:56
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 s…
From Prison to Oprah [not-audio_url] [/not-audio_url]

Duration: 56:52
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,…
Vote for Jesus! w/ Jonathan Rauch [not-audio_url] [/not-audio_url]

Duration: 45:20
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-P…
Tribalism is Dumb (w/Andrew Heaton) [not-audio_url] [/not-audio_url]

Duration: 1:06:10
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…