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.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic:
The Key To Happiness Is Saving More Not So Much Making More Money! (Financial Samurai)
During our conversation, you’ll hear us mention:
- Importance of budgeting vs. income growth
- Why people don’t take control of their money
- Taking financial responsibility early in life
- The misconception that budgeting restricts freedom
- Automation as a budgeting tool
- Emotional connection to money decisions
- Role of mindset in achieving financial goals
- Budgeting for joy and values
- The “don’t deprive yourself” approach to spending
- Using money as a tool for intentional living
- Fear of looking at finances
- Starting small with financial habits
- Budgeting as a team sport in relationships
- The value of checking in regularly on finances
- Money systems as personal and flexible
- Why budgeting apps don’t work for everyone
- Identifying financial “leaks”
- Setting priorities before making a money plan
- “Pay yourself first” and how to make it stick
- Adjusting budgets as your life changes
- Budgeting as a form of self-awareness
- The impact of financial role models
- How to talk about money without shame
- Budgeting to reduce anxiety
- Celebrating wins in your financial journey
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jesse Cramer
Another thanks to Jesse Cramerfor joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors at Personal Finance for Long-Term Investors – The Best Interest – Podcast – Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant
Check Out Paula’s site and amazing podcast: AffordAnything.com
Follow Paula on Twitter: @AffordAnything
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- When was the first in-flight meal served on an airplane?
Mentioned in today’s show
Join Us on Monday!
Be sure to tune in on Monday when Theme Park Insider’s Robert Niles comes down to help us officially usher in summer, as he does every year.
Miss our last show? Check it out here: Is Any Expense Truly “Worth It”? (with Leisa Peterson) SB1682.
Written by: Kevin Bailey
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