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The Stacking Benjamins Show

How to Actually Enjoy Holiday Small Talk (And Give Better Gifts for Less) SB1771

The Stacking Benjamins Show

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

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

4.42K Ratings

🗓️ 8 December 2025

⏱️ 67 minutes

🧾️ Download transcript

Summary

Holiday parties make you want to hide behind the cheese tray. Gift-giving season makes your budget cry. This episode is your survival guide for both.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Pulitzer Prize-winning author Charles Duhigg to turn holiday small talk from awkward endurance test into something you might actually enjoy. Whether you're facing the office party, a family gathering with that cousin who won't shut up about crypto, or the neighborhood potluck where you know exactly three people, Charles reveals how to walk into any room with confidence, even if you're an introvert who'd rather be home watching movies.

The secret? Super communicators aren't the loudest people in the room. They're the ones asking better questions, reading the conversation correctly, and making others feel heard. Charles breaks down the skills that turn painful small talk into genuine connection, and why introverts actually have hidden advantages at holiday gatherings (yes, really).

Then the crew tackles the other holiday stressor of gift-giving that doesn't demolish your December budget. Joe, OG, and Doug explore the rising trend of secondhand gifting. It's not just about saving money (though your wallet will thank you). It can be more meaningful, more creative, and kinder to both your finances and the planet. From thrifted treasures to thoughtful "found" gems, they share how to give smarter instead of just spending more.

Plus, Doug's toilet paper trivia arrives right on schedule (because what's a holiday episode without something unexpected?), along with stories about neighbors behaving badly and a brief tour through apps you forgot you're still paying for.

What You'll Walk Away With:

• Charles Duhigg's framework for turning small talk into actual connection without feeling fake

• Why introverts have secret advantages at holiday parties and how to use them

• Smart, budget-friendly gifting strategies that feel thoughtful rather than last-minute or cheap

• The case for secondhand gifts and how to do it in a way that feels special

• How to avoid blowing your holiday budget without looking (or feeling) stingy

• Creative ways to personalize gifts without overspending or resorting to gift cards

• Why communication skills affect both your happiness and your financial decisions

This Episode Is For You If:

• Holiday small talk feels like torture and you'd rather shovel snow

• You want to give meaningful gifts but refuse to wreck your January budget doing it

• You're an introvert dreading the season of forced social interaction

• You're tired of generic gift guides telling you to "just spend less" without actual ideas

• You believe better conversations and smarter spending are both learnable skills

Before You Hit Play, Ask Yourself:

What's the most meaningful non-new gift you've ever given or received? Think about why it mattered. That's the kind of gifting Charles and the crew are talking about. Drop your story in the comments because we're building the anti-Amazon holiday gift playbook together.

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-actually-enjoy-holiday-small-talk-1771/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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Transcript

Click on a timestamp to play from that location

0:00.0

finally getting cold here in northeast Texas.

0:03.8

And that means my hands for everybody north of the Mason-Dixon line, cold we mean 60s.

0:09.4

Yeah, right.

0:10.4

Yeah.

0:10.6

Morning lows in the mid-40s.

0:13.1

It means I have to put on socks cold, like that cold.

0:16.5

Pants, yes.

0:17.5

We've been shoveling for three or four weeks, and you're now just maybe seeing a little

0:21.7

dew on the ground. To get my pants out. We're my sweatpants. Yeah. I did put on a sweatshirt

0:27.2

today because I was like, yeah, we're talking real cold, put on a sweatshirt kind of cold,

0:31.0

like real cold. At the beginning of our Monday shows, if you're new here, welcome, first of all,

0:36.5

second, grab the mug

0:38.5

and lift it in the air because we begin every week by saluting those people that protected us

0:43.0

all weekend so that we could party like it's 2025 this last month of the year. So on behalf of

0:49.9

the men and women at Navy Federal Credit Union who serve our active duty troops and our veterans and the people who make podcast to Mom's Basement. Here's to you. Thank you so much. Urah. So I'll go stack Benjamins together now. Wow. That is mighty brave of you to be waving around at Michigan State Spartans mug this time a year. It's basketball season, Doug.

1:11.1

It's basketball season.

1:12.1

By the time this airs, I'm pretty sure your football coach is looking for a new job. It's basketball season. No, didn't you hear, Doug? They just have eliminated football. Oh, State just got rid of it? They're just like we're good. After this year, I think that's okay. I went to a basketball school too,

1:28.7

but we never had any pretences.

1:30.7

We never acted like, like we're good. After this year, I think that's okay. I went to a basketball school too,

1:28.7

but we never had any pretences. We never acted like we were once a football school. We're

1:33.0

just, we make quarterbacks and we have great basketball teams. Ours goes off and on. We're like,

1:38.3

yes, we're no. Yeah, no. Yeah, no. How about we get the show started?

...

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