Why Doing Less With Your Money Is the New Investing Edge (SB1815)
The Stacking Benjamins Show
Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
4.4 • 2K Ratings
🗓️ 13 March 2026
⏱️ 68 minutes
🧾️ Download transcript
Summary
Millennials didn't just change how people invest -- they changed what investing even looks like. Cheaper, faster, more automated, and occasionally more dangerous than anything that came before. The real question isn't whether to adopt their habits. It's which ones are actually building wealth and which ones are quietly lighting your portfolio on fire. Joe, OG, Jen Smith (Frugal Friends), and Doc G (Earn & Invest) sort the signal from the noise.
What You'll Walk Away With
- The quiet Millennial investing shift that made building wealth more accessible than any generation before them -- and why most people missed it
- Why automation may be the single most powerful tool in your financial stack, and the one condition that turns it against you
- The difference between technology built to help you invest and technology built to keep you tapping the trade button
- How budgeting apps can create real spending clarity -- or accidentally trigger what the crew calls "procrasti-spending"
- Why fewer investment decisions often outperform more of them, and what the research actually says
- The hidden cost of frictionless trading and why the winning move is sometimes the most boring one available
- Where to take big swings if you want outsized rewards -- and why your long-term portfolio probably isn't the right arena
- How Millennials are diversifying beyond just assets, and what that broader thinking means for investors in their 40s
- The honest tension between values-based investing and long-term returns -- and how serious investors are navigating it without sacrificing either
- What growing portfolio customization actually means for everyday investors who aren't managing millions
Why This Matters Now
If you're in your 40s, you've watched an entire new financial infrastructure get built around a generation younger than you -- and you may be wondering what's worth borrowing. More access and more information don't automatically produce better outcomes. Knowing which Millennial habits genuinely compound over time, and which ones just feel productive, is the kind of edge that shows up in your account balance a decade from now.
From the Basement
OG makes his case for patience (again), Doc G steers things toward the bigger life picture, and Jen Smith grounds the conversation in the money habits real people actually use. Doug surfaces a trivia question involving a NASA probe budget -- and whether you think you know the answer or not, the basement scoreboard has a way of humbling even the most confident Stacker.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
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Transcript
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| 0:00.0 | Hey, this is Joe Sister Nikki. |
| 0:03.1 | I think I might be the only girl in the world who has a brother who spends his entire day in the basement, pretending he has an internet radio show. |
| 0:17.5 | Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show. |
| 0:28.5 | I'm Joe's mom's neighbor, Doug, and what's your investing strategy? |
| 0:36.8 | Today we'll highlight five rules one |
| 0:39.2 | publication says you can thank millennials for plus it's the last month of the first quarter we |
| 0:45.8 | gotta have someone from either team jesse or team paula challenge oh gee come on you two we'll step |
| 0:52.6 | forward to make this trivia contest a race? |
| 0:55.7 | Let's find out. |
| 0:56.9 | And now, a guy who's always racing for better returns, it's Joe. |
| 1:02.1 | So, see-high. |
| 1:06.5 | Hey there, Stackers. |
| 1:08.7 | Happy Friday. |
| 1:09.9 | Let us be the first ones to usher in a fantastic weekend of money fun with our chatiest |
| 1:17.0 | episode of the week. |
| 1:18.1 | And man, we got a fun one today because we're going to be talking about all the things |
| 1:23.2 | that we can steal from millennials. |
| 1:25.0 | And if you're a millennial, you can steal from other millennials. If you're not a millennial, we're going to steal from them or you can steal from yourself. You can do whatever you want to do. The guy who always does what he wants to do is here. Doug, what's going on, man? Hey, buddy. Just having some great weather up here in the frozen tundra. But are you ready to steal for millennials? Let's just be clear here about the mission today. Aren't we all? Let's just take it from them. Oh, boy. And the guy who is he, is he a millennial or is he like younger Gen X? I think he's young Gen X, isn't he? Mr. O.G. is here. |
| 2:03.8 | Attitudinally, that dude is maybe the greatest generation. He's great. |
| 2:07.1 | He might be like a depression era baby. |
| 2:10.1 | Millennials were born in 95. |
| 2:12.4 | Were they? |
... |
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