‘Young Money’ with Jack Raines

‘Young Money’ with Jack Raines

Author: Paul Ollinger September 3, 2026 Duration: 57:39

This week, I’m talking to Jack Raines, the guy behind the mega-popular Substack Young Money and author of a great new book called Young Money: A Field Guide to Wealth and Purpose in Your Twenties.

After graduating from college and landing a finance job at UPS, Jack turned $6,000 in retirement funds into $400,000 trading SPACs in his spare time. Then, by continuing to trade SPACS, he turned that $400k into $200k! This experience was expensive but vital.

Jack started publishing his thoughts about careers and finances on Young Money, and has built a following of over 60,000 “anxious but ambitious” readers. Morgan Housel, author of The Psychology of Money, called him “one of the best money writers around.”

Perhaps that’s why he got a call from Penguin Random House and an eventual book deal. Like Jack himself, it’s a book of unbridled enthusiasm and optimism. It’s a trip to read about money through the eyes of a 29-year-old who’s had just enough interesting life experience but has lost zero of his youthful energy.

If you have a young adult in your life who has found her way into adulthood, or one who is trying to figure himself out, Young Money might be the perfect read for them. In the meantime, check out my conversation with the pride of Tifton, GA, Jack Raines!

We talk about travel, Macon, GA, billboards along I-75 (“Repent or die!”), working at UPS, the Allman Brothers Band, playing Call of Duty in his pajamas during COVID, Wall Street Bets, and the Wall Street Journal’s Spencer Jakab.

Stay gold!

Follow Paul on Instagram here and Twitter here.

Get Jack’s book here.



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
How to Get Rich in America [not-audio_url] [/not-audio_url]

Duration: 1:06:04
✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But…
The Fragile Power of Wealth [not-audio_url] [/not-audio_url]

Duration: 47:24
If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusive…
Surviving the Loss of a Child [not-audio_url] [/not-audio_url]

Duration: 1:04:01
“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…
Millionaires v. Billionaires in NYC [not-audio_url] [/not-audio_url]

Duration: 1:06:04
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-w…
The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain [not-audio_url] [/not-audio_url]

Duration: 1:01:25
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…
Money, Fame, and Misery: Meet the Beatles [not-audio_url] [/not-audio_url]

Duration: 58:00
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…
Believe and You Will See! (w/ Nir Eyal ) [not-audio_url] [/not-audio_url]

Duration: 57:46
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 Limi…
Gina Gershon on Fame, Desire, and Boobs [not-audio_url] [/not-audio_url]

Duration: 1:00:42
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…
The Courage to Be Right w/ Matt Kaplan [not-audio_url] [/not-audio_url]

Duration: 58:18
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…
Insider Trading w/Tom Hardin [not-audio_url] [/not-audio_url]

Duration: 1:13:52
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.…