What really moves the needle on your happiness—making more money or saving more of what you’ve got?

This week, Joe Saul-Sehy and OG are joined by Paula Pant, Jesse Cramer, and the guy who still owes money on his Beanie Baby collection—Doug—for a roundtable filled with bold financial takes and even bolder choices. It’s a rapid-fire round of “either-or” dilemmas, and while nobody gets voted off the island, a few sacred cows are gently tipped over.

Should you max out your retirement account or finally slay your student loans? Ditch credit cards for cash? Bet your future on crypto or keep it stuffed in a fireproof mattress? Our panel debates these decisions and shares real-life stories of what’s worked—and what’s blown up like a microwaved burrito.

Of course, it wouldn’t be The Stacking Benjamins Show without a detour or two: we dig into financial hoarding (how many dusty envelopes is too many?), reveal why your credit score might be your best frenemy, and serve up some vintage airplane trivia, just to keep things classy.

So whether you're team "Earn More" or team "Cut Back," this episode delivers the kind of guidance that helps you feel a little more confident making your next money move—even if it’s just saying no to another financial “shortcut.”

Topics covered include:

Why more income might not be the golden ticket
The case for ditching your credit card (and why that makes Doug twitchy)
Saving vs. investing vs. spending like you’re already retired
What financial hoarding reveals about your mindset
Index funds vs. individual stocks: which one should get your long-term commitment?
The never-ending crypto debate (now with 12% more existential dread!)
How obsessing over your credit score may or may not ruin your weekend

If you’re figuring out how to balance today’s latte with tomorrow’s freedom—or you just want to feel smarter about money than your cousin Gary who “invests in vibes”—this one’s for you.

And remember, no matter how much you earn or save, the real ROI is tuning in with the Stackers each week.

FULL SHOW NOTES: https://www.stackingbenjamins.com/the-happiness-debate-1683/

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ep. 57: Jason Posel, VMS, MSP, And The Plumbing Powering The Freelance Economy