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The Stacking Benjamins Show

The Happiness Debate (SB1683)

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Personal Finance, Financial Planning, Education, Retirement, Investing, Cfp, Business, Money

4.42K Ratings

🗓️ 16 May 2025

⏱️ 70 minutes

🧾️ Download transcript

Summary

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.


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Transcript

Click on a timestamp to play from that location

0:00.0

It's easy to grin when your ship comes in and you've got the stock market beat.

0:08.0

The man worthwhile is the man who can smile when his shorts aren't too tight in the seat.

0:16.0

Ha ha ha ha ha ha ha ha ha.

0:19.0

Okay, Cookie, you'll be honored.

0:25.6

Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show.

0:31.6

I'm not's mom's neighbor, Doug, and does making more money actually make you happier?

0:45.7

Or does shoveling away cash excite you?

0:48.5

We'll talk through this and other big either-or questions on today's show.

0:53.5

But that's not all, either one of these brilliant minds

0:56.3

will win my trivia today or the show will never end,

1:00.4

which is better?

1:01.7

And now a guy who never ends

1:03.8

when you ask about his favorite board games,

1:09.3

it's Joe Salcii.

1:11.6

Doug, you know you love it.

1:16.8

He knows he loves it.

1:18.1

I love it because I have trouble falling asleep at night

1:20.2

and then you just, you're like a magic pill.

1:23.4

Welcome back to the Stacky Benjamin show

1:25.7

where we've got some crankiness in the basement today.

1:29.5

But, man, we're going to have fun during the next hour.

1:32.5

And you know why?

...

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