‘Young Money’ with Jack Raines episode artwork

EPISODE · Sep 3, 2026 · 57 MIN

‘Young Money’ with Jack Raines

from Reasonably Happy with Paul Ollinger · host Paul Ollinger

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

Episode metadata supplied by the publisher feed · Published Sep 3, 2026

Embed this episode

Ready to play

‘Young Money’ with Jack Raines

0:00 57:39

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Reasonably Happy with Paul Ollinger?

This episode is 57 minutes long.

When was this Reasonably Happy with Paul Ollinger episode published?

This episode was published on September 3, 2026.

Can I download this Reasonably Happy with Paul Ollinger episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!