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
Enjoy!
Our Topic:
5 Investing Rules You Can Steal From Millennials (Kiplinger)
During our conversation, you’ll hear us mention:
- Millennial investing habits
- Investing automation
- Tech democratization
- Robo advisors
- Target date funds
- Investing early
- Budgeting apps
- Spending tracking
- Procrasti spending
- Financial noise
- News overload
- Action bias
- Frictionless trading
- Gambling behavior
- Risk tolerance
- Time horizon matching
- Diversification
- Concentration risk
- Career risk
- Skill building
- Side hustles
- Multiple income streams
- Networking value
- ESG investing
- Values based investing
- Consumerism backlash
- Historical investing access
- Bucket shops
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jen Smith
Another thanks to Jen Smith for joining our contributors this week! Hear more from Jen on her show, Frugal Friends at Frugal Friends Podcast – Podcast – Apple Podcasts.
Visit her website at The Frugal Friends Podcast – The Podcast About Spending Less & Saving More
Check out her most recent book Buy What You Love Without Going Broke: Transform Your Spending and Get More of What Money Can’t Buy―An Empowering Personal Finance Guide with a … Plan, Take Control of Your Finances Today!.
Doc G
Another thanks to Doc G for joining our contributors this week! Hear more from Doc G on his podcast, Earn & Invest, on Apple Podcasts.
Check out his latest book The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
OG
For more on OG and his firm’s page, click here.
Doug’s Game Show Trivia
- NASA hopes to send a probe to Uranus in 2044. What is the currently proposed budget for the mission?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday when we’ll tackle setting up your foundation of good money habits.
Miss our last show? Check it out here: When Money Rules Don’t Match Real Life (Your Questions!).
Written by: Kevin Bailey
Episode transcript
[00:00:00] opener: Hey, this is Joe’s sister, Nikki. 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 [00:00:17] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show. [00:00:32] Doug: I’m Joe’s mom’s neighbor, Doug. And what’s your investing strategy today? We’ll highlight. Five rules. One publication says you can thank Millennials for, plus it’s the last month of the first quarter. We gotta have someone from either Team Jesse or Team Paula Challenge og. Come on you two. We’ll step forward to make this trivia contest a race. [00:00:55] Doug: Let’s find out. And now a guy who’s always racing for better returns, it’s Joe Saw Sea High. [00:01:06] Joe: Hey there, stackers. Happy Friday. Let us be the first ones to usher in a fantastic weekend of money. Fun with our Chattiest episode of the week. And man till we got a fun one today, because we’re gonna be talking about all the things that we can steal from millennials. And if you’re a millennial. You can steal from other millennials. [00:01:28] Joe: If you’re not a millennial, we’re gonna steal from them. Or you can steal from yourself. You can do whatever you wanna do. The guy who always does what he wants to do is here. Uh, Doug, what’s going on, man? [00:01:37] Doug: Hey buddy. Just, uh, having, uh, some great weather up here in the frozen tundra, [00:01:44] Joe: but are you ready to steal from millennials? [00:01:45] Joe: Let’s just be clear here about the mission today. Aren’t [00:01:47] Doug: we all, aren’t we all just sick of them and their neediness? Let’s just take it from ’em. [00:01:54] Joe: Oh boy. And the guy, who is he, is he a millennial or is he like younger? Uh, gen XI think he’s young. Gen X, isn’t he? Mr. OG is here [00:02:03] Doug: at Attitudinally. That dude is maybe the greatest generation. [00:02:07] Joe: He, he’s greatest. A hundred hundred 70-year-old Jesus. He might be like a depression era. [00:02:12] Doug: Baby. [00:02:13] OG: Millennials were born in 95. [00:02:16] Joe: Were they? What the [00:02:16] OG: heck? [00:02:17] Joe: Yes. [00:02:18] Doug: No. [00:02:18] Joe: Oh, I didn’t. Who knew? Did you know? I didn’t know. I had no idea. And a guy who was definitely born in 1995, doc G is here. Are you millennial, doc G? [00:02:28] Doc G: No. No. [00:02:29] Doc G: I was not born in 1995. I know you look at this face and you say millennial, but no, I’m Gen X. For [00:02:37] Joe: the four people that don’t know Doc G from our brother, show, earn and invest. Tell everybody about the show, man. [00:02:44] Doc G: Earn and invest is next level. Financial, personal finance, and purpose, meaning everything under the sun. [00:02:52] Doc G: We talk about life in general, how you can earn and invest in your life. Sometimes we just talk money. Other times we talk all sorts of things. I got a guy coming up, we’re gonna talk about investing in Broadway shows. So, you know, sometimes we talk money. Wow, [00:03:06] Joe: that’s not a, we did a show on Monday O OG about binary returns. [00:03:11] Joe: There’s a binary return investing in a Broadway show. [00:03:14] OG: I, I would, I would, uh, disagree with that. That is, uh, that is a way different thing. I actually happen to know people who do that. So [00:03:21] Joe: you don’t think that’s binary though? It’s either gonna do pretty well or [00:03:24] OG: no, [00:03:25] Joe: maybe not. [00:03:25] OG: No. I think you have a lot more control over that than, uh, something as silly as like investing in Doug’s Ice Cream Tang Shop Ice Cream and Tang Warehouse or whatever the hell we were [00:03:36] Doc G: talking. [00:03:36] Doc G: So according to Ken Davenport, the guy I’m interviewing about one in five, recoup, right? So your goal first is to recoup you put the money in, you hope to get at least your money back. But about one in five make a profit. But a lot of people go into it ’cause they love, they love Broadway, right? They love this idea being part of the in crowd s, [00:03:53] OG: singing In the Rain. [00:03:56] Joe: A woman who loves Singing in the Rain down in Florida from Frugal Friends, she’s back. Jen Smith is here. How are you? [00:04:04] Jen: I’m really good and I am a bonafide millennial. I’m right in the middle. 1989, some would argue the best year. I would say Swifties would argue it’s the best year. [00:04:15] Joe: So wait a minute, somebody Doc who just said that millennials were born starting in 1995. [00:04:19] Joe: Is it 1985? [00:04:21] Doug: No, it’s 81 to 96. [00:04:23] Joe: 81 to 96. So yeah. So Jen, you’re here today. You’re here today so we can steal from you. Is that fine? [00:04:30] Jen: The lone, millennial and female voice, and I. It will not represent all of us. [00:04:37] Joe: I was [00:04:38] Jen: gonna say, I’ll not take that mantle. [00:04:40] Joe: There is no pressure there, Jen. Not at all. [00:04:42] Jen: Nope. [00:04:42] Joe: So for the people that haven’t heard about your beautiful podcast, frugal Friends with you and your amazing co-host, Jill, what have you guys been up to lately? [00:04:51] Jen: We are over on YouTube right now. We’re doing a lot of video and just a lot of commentary on consumerism, pushing back on overconsumption that is pushed on social media, in traditional media, and even in our communities. [00:05:08] Joe: We’re doing this live on YouTube right now, in fact, and we’ve got Drew hanging out with us who says that he was born in 96. [00:05:16] Joe: He had to look it up whether he was a millennial or not. So there we go. We, we got lots of, uh, people paying attention to whether they’re millennials. Well, we got this wonderful piece from Kiplinger that is five investment strategies we can steal from millennials. I don’t care where we steal from, we just wanna make sure that they’re good ones. [00:05:33] Joe: So, Jen, doc g, og, Doug and I, we’re gonna get into it here in just a minute, but we’ve got a couple sponsors to help us keep on keeping on. We’re gonna hear from them first, and then let’s do some stealing today. Huh? [00:05:55] Joe: All right. The inspiration for today’s discussion comes to us from Kiplinger. As I mentioned just before the break, Corey Ann Hicks wrote this piece, five Investing Rules you can Steal from Millennials. She opens this up by saying Millennials are reshaping the investing landscape. See how the tech savvy generation is approaching capital markets and the strategies you can take from them. [00:06:17] Joe: I’m always, always open to stealing from anybody. I mean, one of my favorite interviews we’ve done here was, uh, Austin Cleon Steal Like an Artist, right? We want to take things that work and steal them, number one on his list, embrace tech to automate and accelerate investing, and I’m wondering, well, Jen, let’s start with you because you’re a millennial. [00:06:38] Joe: Do you think that using tech, does that accelerate your investing? [00:06:44] Jen: Absolutely when investing was like when index funds were invented, you didn’t have a computer to just be able to go on and buy them. I mean, even before that, when you were buying single stocks, you always had to go through someone and you couldn’t be sure if they were working in your best interest or theirs. [00:07:05] Jen: And then as we have grown in the internet and technology investing has just gotten more and more affordable and accessible. And for millennials, we graduated college around oh eight to oh, like to 12, and there weren’t a lot of jobs for us. So we didn’t have a lot of money right out of college to start this like large time horizon with investing. [00:07:29] Jen: And so we needed to be able to do small amounts affordably. And so technology really has been the bedrock of my investing. I did not know that I could invest on my own. I thought you had to go through a guy. Because that’s, my parents didn’t invest at all, but my parents’, friends, they all had a guy, so I had to learn through podcasts, like Stacking Benjamins, that there was even an option to do it on your own through the internet. [00:07:57] Joe: Wow. Investing through those little pipes that they run underground. Mm-hmm. And then in the other world, [00:08:03] OG: no, I’ve been told it’s like suitcases. [00:08:06] Joe: Is that the way it works? It’s like packets. They call ’em packets, right? Doug [00:08:09] OG: Nose. Yeah. It’s like suitcases. And then there’s like people that are moving the suitcases sometimes. [00:08:14] OG: They carry a lot of suitcases. [00:08:15] Doug: Little elves put put packets into the suitcases. [00:08:19] OG: Yeah. Something [00:08:20] Doug: about suitcases, like sweet, sweet, low packets and they ship ’em off. That’s [00:08:22] Joe: welcome to the Stacking Science podcast everybody. This is, uh, we’re gonna dive into the science of how the internet works. Doc, let’s ask you, man, I mean, you know, Jen makes this case that using your computer, using some of the modern tools has made it easier to invest. [00:08:37] Joe: But is it, has it democratized investing or has it just gamified it? Because I feel like I look at like what Robin Hood’s gotten in trouble for a lot. Like it’s over gamification to make people do things that might not be the right thing. [00:08:50] Doc G: I think it’s done both and here I think we can differentiate kind of basic tech, which is right, computers in the internet from I think some of the more complex FinTech you see out there now, like Robinhood, so you know, I’m part of Gen X and so we were right there where we went from defined benefit to defined contribution, right? [00:09:10] Doc G: We got rid of pensions and we went to 4 0 1 Ks and a lot of people in Gen X didn’t really make that transition really well. So they didn’t get their money into the 4 0 1 Ks. They didn’t really catch up with the retirement savings. Now what we see in millennials. Everything’s automated now. So you join your company, they put you into a computerized portal, you automatically opt in to a defined contribution. [00:09:37] Doc G: Your defined contribution gets opted into a target date fund. All of that is automated, and all of that is because of the basic simplified tech. And so I think millennials have really done well with that. And I, that’s why I think millennials in general have done better saving for retirement than at least a lot in Gen X did. [00:09:56] Doc G: On the other hand, we then have a little bit more of the complicated tech, which allows you to gamify things, things like Robinhood, which really pushes people to trade often, and to get on Reddit and learn about what’s the coolest, greatest, newest, and it’s turned it really into a game. So I think it’s done both. [00:10:16] Doc G: The gamifying part is probably not as good for us. [00:10:18] Joe: I did talk about one thing we all need to steal from millennials, Jen, is that, uh, you guys started earlier. How old were you when you first invested? [00:10:24] Jen: It was 2017, so I would’ve been 28. Okay. So I was a little older ’cause we paid off all of our debt. We paid off $78,000 of debt first, but it only took us two years. [00:10:37] Jen: We just took that same momentum and we, you know, for like four to six years maxed out everything we could. And it was a lot easier I think, than there was a lower, not easier, but there was a lower barrier to entry. Yeah. To get into investing for somebody who had never invested before, whose parents had never invested before. [00:10:59] Jen: Had actually, the only thing I had been told about investing was that my grandmother. Put like $2,000 in penny stocks into the stock market and then lost it all. And like nobody in my family invested after that. So [00:11:10] Joe: investing for you was a cautionary tale, [00:11:13] Jen: right? It was. I thought I had to have a guy, I had to pay him a commission. [00:11:17] Jen: Front load, backend load, like all of that. And. The financial guru that I was learning from at the time also said that, and then I said, let me see if there are other ideas out there. And that was another thing that the internet provided us, is education. Not just one voice to learn investing from, but a lot of different voices, which I mean is a blessing and a curse, right? [00:11:43] Jen: Right. Because you’ve got people, right, you on Reddit with the stocks and stuff, but you’re always gonna have that section of people who wanna make things more complicated than they should be. But it has, I think, really democratized investing for the better. [00:11:58] Joe: Yeah. I took this, uh, social media course through MIT that was really good. [00:12:03] Joe: And the professor, a guy named Son Oral, who was, uh, early on in uh, Twitter and, um, some of the dating apps said that, you know, you gotta decide, Jen, to your point, whether you play for good or bad. All that the internet does though, is it amplifies it. So, you know, the internet doesn’t say this is a good thing, this is a bad thing, but it will certainly amplify messages and get bad stuff and good stuff out very quickly. [00:12:27] Joe: I’m wondering, og with millennials starting earlier, is, is that more important than investing perfectly? [00:12:34] OG: Oh yeah, absolutely. I, I mean, if you are 80% correct, but you start right away, you have so much more flexibility and margin, you know, margin of safety into the future. And I do think that technology has helped make it easier for people. [00:12:49] OG: It’s helped. I think what you said there in terms of amplifying, I think is a good example. It, it will expose your flaws pretty quickly. If you’re a gambling addict, guess what? Like there is a tool for that. You do not have to go all the way down to the casino to do it. You don’t have to have a bookie, you don’t have to do it. [00:13:06] OG: You can do it on your phone. You don’t have to [00:13:07] Joe: wear pants. [00:13:08] OG: You, yeah, you can link it to your credit card or your PayPal account or whatever. It’s like you could, you could spend all your money and no one will stop you in, you know, 90 minutes if you want. So that’s a bad thing. The good thing with technology, of course, is sometimes it can give you some, uh, lower barriers to entry and make it easier to automate it. [00:13:30] OG: I think that’s really the biggest piece around technology is making it on autopilot, I guess maybe is a better way of saying it. So you make the decision one time, you know, unlike, like Jen was talking about back in the old days when you guys were around, it was like, you know, every month you had to figure out. [00:13:49] OG: How much money is left over and you know, you’d invest the difference, right? But now you can just automate it. You can automate it outta your paycheck, you can automate your, your Roth contributions outta your bank account systematically. You can set up dollar cost averaging from your paycheck into your brokerage account. [00:14:04] OG: Super easy. So I think that that’s helped quite a bit in terms of at least pushing people in the right direction. [00:14:10] Joe: I do like the idea doc that, uh, automation was really a great thing that millennials especially latched onto, right? Let’s just automate it and get it moving. But also millennials also ushered in robo-advisors, and I think if I’m 25, do I need tax loss harvesting and do I need a perfectly designed portfolio that’s right on the efficient frontier? [00:14:33] Joe: Like I don’t get me wrong, robo-advisors are doing all this cool stuff, but it’s stuff that’s, that is cool for a 50-year-old, much more I think, than a 25-year-old. [00:14:42] Doc G: You know, I’d still say that overcorrection is better than not engaging at all. And so yeah, I think there’s gonna be some overshooting, and I think with robo-advising and some of these things, we’ve taken the basic idea, invest, invest early and invest in index funds, and we’ve turned it into much more complicated, like, can you get that extra 1% by tax loss, harvesting, et cetera, et cetera. [00:15:07] Doc G: So I, I mean, an overshoot I think was bound to happen, but I don’t think the negativity of that outweighs the getting engaged, which I think millennials did take a step up from Gen X, and certainly I think some of this automation and some of the tech available made it better. [00:15:26] Joe: Let’s go from investing apps, Jen, over to budgeting apps. [00:15:29] Joe: You know, now we have all these pretty budgeting apps. I use Monarch, I’ve used Tiller Money. I, I like Tiller money a lot too. Why nab, you know, has an amazingly robust community. Have these apps truly helped people or does it just make tracking it prettier and make you feel like you’re doing more? [00:15:49] Jen: It depends on the person and the season and the goal, I think people can procrast to spend, which is spending money on something to like, yeah, we, we say that all the time. [00:16:00] Jen: There it is. Yeah. Do you really? So, [00:16:02] Joe: oh [00:16:02] Jen: my god, yes. So people spending money to do something productive, like get healthier or get better with their money. Spending money on doing something like that instead of actually doing the thing people can procrast to spend. I [00:16:15] Joe: feel like you’re looking at me when you say that. [00:16:17] Joe: Are you looking at me? Are you staring into my soul, Jen [00:16:19] Jen: Smith? No, I’m just, I’m staring right into the center of line between everyone, so it can happen, right? But these things have also made it a lot easier to track our spending and we can see in real time. Oh, I have a widget. I have the Monarch widget on my phone so I can keep up with my transactions and I can see really quickly Oh. [00:16:41] Jen: I don’t remember making that transaction or, oh, I canceled that. And that transaction went through, I had a gym membership that charged me an annual fee six months into my membership. And I was like, well, nope, that’s not right. Uh, so I got that refunded and that happened within 24 hours. So it has made stuff like that easier. [00:17:00] Jen: But on the flip side, it can also make it easier to get really in the weeds with budgeting, where we have like 18,000 categories. Oh, and then frugal friends, we get complaints all the time. Like, how do I make budgeting sustainable? How do I make tracking my spending sustainable? I’m like, well, stop. Making two transactions at the grocery store where you’re putting all your food first and then your paper product second, because those are two different categories in your budget. [00:17:27] Jen: Jill and I have differing views on this because she kind of does that, and for me it’s too much. So it does depend on the person. But again, I do love what technology has done for that space. [00:17:41] Joe: I love the fact though, that it is what you make of it. It still is what you make of it. Mm-hmm. I see people talking about. [00:17:47] Joe: Ai. You know, obviously all the time we all talk about ai, I feel like all the time, but it is what you make of it and how you, how you end up using it. The second part of this piece was that millennials grew up in a time when not only did we have noise on televisions that we could shut off, or magazines that we could stop, but now then you go over your computer and it’s surrounded by advertisements all the time. [00:18:07] Joe: You jump on Spotify to listen to the Stacky Benjamin Show or Earn Invest or Frugal Friends, and you hear advertisements there. We are being inundated with noise and I’m wondering, OG this is this 24 7 financial news cycle that we live in now. Live now, is this like, is this a feature or a bug for modern investors? [00:18:31] OG: Well, I, you know, I think about it this way. When we were kids, you know, you think about like the little crawl that happens across the bottom of the screen. What was that reserved for [00:18:44] Joe: the bottom of the screen. Oh, there was truly breaking news. Truly, truly, truly something huge. Like, uh, uh, we went to war. [00:18:54] OG: Okay. Yeah. It probably happened in 91 for that. [00:18:57] Joe: Yeah. [00:18:57] OG: I think it was more, at least where I was, it was more for major severe weather. Okay. I mean, it was for like other stuff, but it was like, you know, da da da da, and you’d like, it would direct your attention on, that’s probably the more often [00:19:10] Joe: thing. Yeah, [00:19:11] OG: yeah. [00:19:11] OG: The TV’s on, right. You come home from school, whatever, but [00:19:13] Jen: more sometimes, [00:19:14] Joe: right? [00:19:14] OG: Yeah. Yeah. Yeah. I mean, that’s kind of top of mind right now, I suppose, but, but it would be more like, in this county there’s a severe thunderstorm warning, right. Or severe tornado warning or something like that. Right. Like it, it attracted your attention to that thing. [00:19:26] OG: Okay. When was the first time that that got put on the screen and hasn’t left since? [00:19:34] Joe: No idea, but I think it was CNN that did it first. [00:19:38] OG: Okay. It was basically a tie, but yeah, some, I’m, I’m talking specifically about like news channels and stuff like that. Yeah. [00:19:43] Joe: Like what, what, what year? [00:19:45] OG: Yeah. [00:19:45] Joe: What year did this happen? [00:19:47] Joe: Uh, 2004. [00:19:50] OG: Close. Anybody else have a different guess? [00:19:52] Jen: 2008, [00:19:53] OG: there was an event that happened that was so chaotic with so much breaking news that we put it at the bottom of the screen. [00:19:59] Joe: Oh, September 11th, [00:20:01] OG: nine 11. Oh, right. Whoa. [00:20:02] Jen: Okay. [00:20:03] OG: It was nine 11 and we started putting that at the bottom, which made sense, right? [00:20:07] OG: Mm-hmm. Like that was in the moment. Pure chaos, right? Since then, it never goes away when you watch a football game on tv. It used to be. If you ever see like the, the, like back in 1971, the last time that this team played, they show the video, right? Like it was the football game. Now you have the score, the timeouts remaining, the time remaining, the play clock remaining who’s on the field, how many rushing yards they have, how many passing attempts the quarterback has, the down the distance, what the penalty was. [00:20:38] OG: Like all this information in your face to watch a football game or to watch the news, I think that it’s the oversaturation of that, whether it’s sports, whether it’s news, and certainly around money is absolutely a problem because it, it focuses you on the wrong thing. When you’re watching the football game, you wanna watch the football game. [00:20:59] OG: Need to care how much time is left on the play clock. Like who gives a crap? Like we’re watching the football game. And so when you, when you have this as it relates to financial stuff, there are times and places where, hey, there’s some financial news going on. We need to pay attention to this. Rarely does it affect, you know, your day-to-day transactions, but stuff that you’ll wanna pay attention to. [00:21:20] OG: But when everything is an emergency, when everything is crawling along the bottom of the screen all the time, 24 7, your brain can’t delineate between is this an actual emergency or is this a what CNBC thinks is an emergency or wants me to believe is an emergency? And more specifically, what do you wanna do during emergency? [00:21:39] OG: Do you wanna sit there or do you wanna do something? You wanna do something, do something. You wanna [00:21:42] Joe: do something, you gotta move, [00:21:43] OG: you gotta like, I gotta do something. Mm-hmm. There’s a flood coming. I need to do something. So the same thing happens with your money. You think that there’s this emergency, so you have this tendency to want to do something. [00:21:53] OG: And for the vast majority of people doing nothing, almost all the time is the right thing to do. [00:22:00] Joe: Let’s go to OGs example, doc of sports, right? You watch a football game now, and on that crawl at the bottom, it will tell you the odds of either team winning the game. [00:22:11] OG: Yeah. In real time. [00:22:12] Joe: In real time. [00:22:13] OG: Like as the pass is in the air, what’s the chances of this pass being completed? [00:22:17] Joe: And between that and the NFL now being part owner of the betting apps, you know exactly why they’re telling you the odds of winning. And not only betting, which is now frictionless that we talked about earlier. We also have frictionless trading. Doc does. Does frictionless trading match with this 24 7 news cycle? [00:22:38] Joe: Does it give us a chance for better returns or more mistakes? [00:22:42] Doc G: Oh, I mean, most definitely more mistakes. You have to remember, money is made in transactions. No one ever made money. When your broker called you back in the 1980s and said, we need to sell this and buy that, if you said yes, the broker made money. [00:22:57] Doc G: If you said, no, no, no, I think I’ll leave everything the way it is. Well, you’re talking [00:23:00] Joe: about middlemen. Middlemen don’t [00:23:02] Doc G: make [00:23:02] Joe: money when you say it. [00:23:03] Doc G: Well, the point being is poly market, all of these betting apps, et cetera, they’re all making money by convincing you to do something. There’s action bias, right? [00:23:14] Doc G: So they wanna present decisions to you often make you feel like you’re gonna miss out or lose if you don’t make a decision, and then push you towards that action bias to create revenue for a third party. And so it makes people feel like our financial decisions are multiple and often and made on a daily or moment to moment basis where all of us know. [00:23:39] Doc G: Actually you want to make some general basic decisions about your finances, automate them, set ’em on autopilot, and then stop making so many decisions. Remember, decisions basically generate costs. Almost always. [00:23:52] Joe: One of my, [00:23:53] Doc G: someone’s making a profit and someone’s paying for it. [00:23:55] Joe: Yeah. One of my favorite, uh, authors, in fact, it’s funny. [00:23:58] Joe: I have, uh, a book of hers that I love right here, uh, the Power of Fun by Catherine Price. She has another piece called How to Break Up with Your Phone, which I think Jen is, is actually really interesting. Like filtering out the noise is half of the game. How do you filter the noise in your life so that you’re able to sit and do nothing? [00:24:18] Joe: Like Andrea said in the comments earlier, don’t do something, just stand there. Which to OGs point the thing that usually is the right thing to do. [00:24:27] Jen: Josh made such a good point that the more information we are presented with, the more confused that we get, the more we get into fight or flight mode, and we want to take some kind of action to compensate for our confusion or insecurity or something. [00:24:47] Jen: And since Jordan brought up biases, we have a complexity bias too. So we think that simpler is stupider. You know, like I must not be as intelligent if I’m not doing anything and I want to be successful. I want to be smart, so that must mean I have to, to do something. And that leads to overcomplicating things. [00:25:06] Jen: And so I think one of the biggest solutions is just getting it out of our screens, off of our phones. If you need to delete social media, delete news apps, unsubscribe from emails for even just a while, not for, but for a season. Then that’s gonna be really necessary to just stop, take a break. Don’t take in as much information. [00:25:30] Jen: Don’t become ignorant. Don’t become apathetic. But do not believe that inundating yourself with information makes it easier to do the right thing. [00:25:41] Joe: Our editor Steve told me a while ago that he just stopped watching the news and he said, it’s amazing how he still knows every big thing that goes on. I feel like we think if we stop, and of course the news cycle wants us to believe this. [00:25:53] Joe: If I stop watching, I’m gonna miss something important. Like I’m gonna miss it. And then I started missing based on Steve’s advice and other people, and I’ll go almost a week without watching and I didn’t miss a thing. [00:26:05] OG: But it turns out that if it’s a big enough deal, you’ll figure it out. [00:26:08] Joe: Yeah. Everybody’s gonna be talking about it. [00:26:09] OG: You, you’ll know about it. [00:26:10] Joe: Mm-hmm. A hundred percent. [00:26:11] OG: I started using grok just to go give me a, like a three bullet point thing of what’s going on right now. In the universe, like what’s happening. Yeah. [00:26:19] Jen: And if everything is important, nothing is important. [00:26:22] OG: Yep. [00:26:22] Jen: Just getting the biggest, most impactful snippets of information, I think is gonna be the best instead of knowing everything about everything. [00:26:32] Jen: ’cause you’re never gonna know everything about everything. You’re gonna know just, uh, an inch deep and a mile wide of everything. You’re not gonna get perspective or nuance. And it’s just going to, it’s gonna lead to, you know, we wanna make 80% good decisions, 20%, you know, whatever. And it’s just gonna lead to a higher percentage of just bad decisions. [00:26:51] Joe: Yeah. A hundred percent. A hundred percent. 80, 20, a hundred percent. A hundred percent of the time we make. That decision’s 80% of the time. I dunno. We’re gonna, we’re gonna leave it right there before I get lost in my own language at the halfway point of every stack of Benjamin’s Friday episode, a year long challenge going on between OG and our frequent contributors, Jesse Kramer and Paula Pant. [00:27:12] Joe: And, uh, why don’t we just keep the genders the same, just to make it easy. So, Jen, you’ll be team Paula. Doc G, you will be Team Jesse. And guys, that means we’ve got good news and bad news. Jen, you want the good news or the bad news? [00:27:25] Jen: I always play for Paula and I always let her down so, [00:27:28] Joe: well, Paula’s really [00:27:29] Jen: gimme the bad news. [00:27:30] Doug: Pretty impossible to let her down. [00:27:34] Joe: Doug, you’re a hundred percent right. I was gonna give you that good news first. You can’t let Paula down ’cause she doesn’t do that well on her own, so there is no good. [00:27:42] Jen: Okay. [00:27:43] Joe: Yeah, no letting her down, [00:27:44] Jen: she hasn’t brought it up to me, so [00:27:47] Doug: I don’t think she talks about her trivia skills to anybody. [00:27:50] Doug: She’s not bringing it up. [00:27:51] Jen: She tries not to mention Stacking Benjamins at all when she’s out and about. [00:27:57] Joe: I think it would be funny though, if she like just for fun, sent you like a, a tersely worded text. I think that would be, that’d be a lot of fun. Uhhuh. Doug, what’s the score of this game thus far in 2026? [00:28:11] Doug: Well, so far we’re looking at a lot of goose eggs. We have, uh, Jesse, with zero points. We have Paula with Zero Points and we have OG with Six Points. So you can’t do any worse Jen or Doc than those guys have. [00:28:28] Doc G: Joe, Joe, I have a, I have a good idea Joe and Doug, why don’t you let me play for OG today? It doesn’t, it doesn’t matter if he’s here. [00:28:37] Doc G: Why don’t you let me play for him? [00:28:38] Doug: This is a great idea. [00:28:40] Joe: OGs gonna sit out and we’re gonna, we’re gonna have Andrea in the chat play for Jesse. Uh, yeah, I don’t know. Uh, we gotta do something here guys. So Jen and Jordan, no pressure, but, um, I think we gotta get moving, um, to get us moving. Doug, you’ve got. [00:28:55] Joe: The actual question. [00:28:56] Doug: Sure do. Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and today’s a big day because we’re talking about your anus. [00:29:04] Joe: I don’t think you pronounce it that way, dude. I think it’s Uranus. [00:29:08] Doug: Yeah, that’s, that’s what I said. Your anus now. Well, you just, just pipe down Joe and let me do my job. [00:29:15] Doug: You’ve had your turn for like the last three hours. It’s my turn to talk. It was on today’s date way before I thought, frankly, way back in 1781 that Sir William Herschel peered into his telescope and yelled, Hey, look how huge Uranus is. [00:29:31] Joe: I don’t think he said that. [00:29:33] Doug: Talking, talking right now. Is it me or is it you? [00:29:36] Doug: It’s me. Okay. Well, lots of people have talked about probing Uranus and finally it wasn’t that guy from third period, but actually it was NASA who got close with the Voyager two spacecraft, which flew by in 1986. Now. NASA wants a closer examination of Uranus, so they’re sending a probe deep into the planets. [00:29:57] Doug: Uh, what’s the word? Um, I don’t think we wanna hear [00:30:00] Joe: the word. We don’t wanna hear the word [00:30:02] Doug: atmosphere, Joe. That was the word I was looking for. Atmosphere. What do you think I was gonna say? Geez, here’s today’s question. Oh, those interruptions were so helpful. This is truly gonna be a Benjamin Burning mission. [00:30:16] Doug: How much money is the proposed budget when the USA sends a probe to Uranus? Assuming it goes off as scheduled in 2044? I’ll be back right after I figure out whether or not Uranus has rings around it once dated someone with rings in a really remarkable place. [00:30:33] Joe: We don’t wanna know. We so do not wanna know. [00:30:37] Joe: Just imagine when Doug found out that, uh, this was today’s date in history. Doug was skipping to the basement. We get to talk about this. [00:30:44] Doug: Distribute. People need to know about, [00:30:46] Joe: we gotta talk about William Herschel and his, uh, telescope. So, oh gee, you got to go first. In 2044, we’re sending a probe to, we’ll call it Uranus. [00:30:55] Joe: How much money is the proposed budget [00:31:00] OG: in today’s dollars or in 2040 $4 [00:31:02] Joe: in today’s, in today’s dollars? [00:31:04] OG: Well, it matters. [00:31:05] Doc G: He’s just wasting time here. He told me you could go there for free before the show started. [00:31:10] Joe: Budget is zero. [00:31:13] OG: I, I I can’t imagine that they have a budget for a 2044 mission that’s not in 2040 $4. [00:31:19] OG: That doesn’t make any sense to me. [00:31:21] Joe: Okay, then it’s said 2040 $4, say a number. [00:31:25] OG: So I think that they are forecasting that this is gonna be a, um, probably a $22 billion project. [00:31:36] Joe: 22 billion with a B dollars. Jesse finished second last year, which means, uh, doc, you are up to bat. [00:31:48] Doc G: I think it’s much higher than that. [00:31:49] Doc G: I’m gonna go a hundred billion, [00:31:51] Joe: a hundred billion dollars. Jen, we got 22 billion and we got a hundred billion. What do you think? [00:31:59] Jen: The first thing that popped into my head, because I have a 6-year-old, is six 7 billion, so 67 billion is my guess. [00:32:08] Joe: $67 billion. So we got 22, 67 and a hundred. We’re all in the billions. [00:32:16] Joe: Let’s see who’s right. We’ll be right back. All right, og, you kicked this off by saying 22 billion. Both Jen and Jordan said not nearly high enough. What are you thinking? [00:32:27] OG: I mean, I’ve got between 22 and 67, so 40, so I’ve got from basically like 40 million. 40 billion on down. Pretty wide range. I am. I’m I It’s not a, it’s not a hundred. [00:32:41] OG: That’s way too much. [00:32:42] Joe: Whoa, Jordan. Those are fighting words. He thinks you’re, you’re way too high. [00:32:47] Doc G: He’s probably right. I’ve been, I’ve been accused of being too high before. Not, not when we’re talking about trivia, but other things. [00:32:53] OG: Too many gummies. [00:32:54] Joe: Yeah. When the answer’s between one and 10 and, uh, doc answers a hundred. [00:33:00] Doc G: I’m, I’m just staying in character. [00:33:02] Joe: Jen, you’re right there in the middle. 67 feeling good. [00:33:06] Jen: I, you know what? I feel like I’ve heard that number too many times. Six, seven in the last, yeah, [00:33:13] Joe: in the last year. [00:33:14] Jen: In the last couple months. Yeah. And so here’s to hoping it pays off in some way, [00:33:20] Joe: man. I hope so. ’cause somebody’s gotta break the streak here, Doug. [00:33:24] Joe: Tell me somebody’s gonna do it. [00:33:25] Doug: Well, hey there, stackers. I’m Uranus lover and a guy with a really long telescope, Joe’s mom’s neighbor, Doug. Today we’re talking about Uranus and probing it in 2044. Can you imagine what Uranus will look like in 2044? I mean, I can’t imagine what a scientific breakthrough that’ll be. [00:33:44] Doug: But the question was how much will the budget be if they go with the currently proposed number. I’m not gonna just tell you what that number is, but I will tell you that it’s 95.8 billion less than what Jordan guessed. 62.8 billion. Less than what Paula Jen guessed, and just 17.8 billion less than what OG guessed. [00:34:06] Doug: The correct answer was 4.2 billion making Captain Cranky pants, our winner. [00:34:12] OG: So it wasn’t today’s dollars, [00:34:14] Doc G: that’s why I was wrong. [00:34:15] Jen: That’s not why I was wrong. [00:34:17] Doc G: If you guessed a 50% return on your money, it would definitely be over a hundred billion [00:34:22] Joe: by 24. 44. You said six seven. Jen, you were gonna say 6.7 more. [00:34:25] Joe: You duck 6.7. I know. I was like, bring in 6.7. Come on. Ugh. [00:34:30] Jen: I am sorry, Paula. [00:34:32] Joe: It’s all right you. You’re gonna get a strongly worded text. [00:34:35] Jen: So close, but so far I’ll be prepared for it [00:34:38] Joe: and the rich get richer this week on the Stacky Benjamin Show. Congratulations og. [00:34:43] OG: Thank you. [00:34:43] Joe: Yet another one. [00:34:44] OG: Are we dormy yet on the year, or do I got about six more weeks? [00:34:48] Joe: He’s, uh, just about rounding third base and headed for home. Let’s bring this podcast into the second half. We’re gonna talk next. Lemme see if I can bring this up. We’re gonna talk next about their third point, which is don’t be afraid of risk. And this is actually funny, Jen, because I remember early on hearing about millennials and risk and the fact that millennials didn’t want to take a lot of risk because like you said, when they first came outta college, there weren’t a lot of jobs. [00:35:15] Joe: We were coming outta the housing crisis. A lot of people were struggling and a lot of people, I remember reading some early stats around millennials that they were afraid to invest. So this idea of millennials and grabbing the risk train and running it ragged is, is that how you feel? [00:35:32] Jen: I think initially it could have been perceived that way, but we also in our first working years out of college, saw the longest bull market in history. [00:35:43] Jen: So I think that was what really shaped. Our risk tolerance. And so I’m very much like a 90% equities type of person. And I think it is because like we’ve seen a lot of tech startups that found their footing during the housing crisis in oh eight, like Uber and all these other tech startups that have just gotten so big and then all the growth seen over that, you know, 10 plus years bull market. [00:36:10] Jen: So I think that is really what has shaped millennials really being not afraid of risk, and that we have a long time horizon because none of us anticipate retiring [00:36:22] Joe: ever. We’re just gonna keep, ever just gonna keep working till we’re 160 years old. Og. I can totally see what Jen’s saying. This big, uh, runup in the stock market goes, Hey, every time I take risk, it pays off. [00:36:35] Joe: You learn from behavior and you’re high fiving yourself because your investments have done really, really well. But when does risk? Tolerance, turn into risk confusion, and maybe we’ve overstepped. [00:36:49] OG: Well, I, you know, I, as you know, I have a big problem with this whole concept of risk anyway, because risk implies the chance of loss, and as we’ve discussed very recently, even on the show, that there’s really no chance of loss when investing in the biggest companies in the universe, given it enough time. [00:37:05] OG: The problem with investing where people make mistakes isn’t the fact that they’re investing. It’s the fact that they don’t match up their timeframes with the money that they need. You know, when they need the money. If you’ve got a kid that’s going to college in two years, pretty stupid to buy Nvidia stock, even if it’s the thing that likes slays it for the next 24 months, because it could also go down by 50% if you match up the timeframe of needing the money with the actual tool that is designed for that cash. [00:37:31] OG: For short term things, maybe a little fixed income for medium term things, but for the vast majority of your money, for the vast majority of your wealth. Investing it in long-term companies. Basically, the ownership of these organizations that you do business with every single day across the spectrum of every single solitary organization in the, in the entire world. [00:37:49] OG: So you don’t have to pick which one’s gonna do well. You just go, I’m gonna own a little slice of everybody and make sure that that’s aligned with your timeframes. There is no risk. The risk is actually taking the money out when you’re not supposed to. Or the risk is behavioral where you go, oh my gosh, I didn’t know that that 20 year money might have a little wiggle in the, in the performance like in 2022 or the, you know, whatever, 17 days surrounding COD when that was a splash. [00:38:16] OG: Or as recently as last year when, when the tariff stuff came out in April, market went down 18% or something like that. Seven days. That’s some [00:38:24] Joe: big bumps. [00:38:25] OG: Yeah, but it happened so fast that if you didn’t know it was happening back to our financial, you know, pornography stuff, if you weren’t paying attention to that, you might’ve missed it. [00:38:35] OG: You might’ve got your statement in March and statement in April and went. Eh, yeah. Not the greatest month, but eh, you know, so the whole solution here is for, for people to use all of these tools in the manner in which they’re supposed to be used. And if you do that, you’re, you don’t have any risk. There is no such thing, [00:38:54] Joe: you know? [00:38:54] Joe: But over the short [00:38:55] OG: Rock, Gee’s got a comment. He, he’s chomping at the bit I can see. [00:38:59] Doc G: He’s like, he’s [00:39:00] Joe: loving it. [00:39:00] OG: G get me in. [00:39:01] Doc G: Go ahead Joe. Ask your question and then I’ll ignore it and say what I wanna say. [00:39:06] OG: Said by a true contributor to the Stacking Benjamin Show. Does, [00:39:10] Joe: he does belong on like CNN. Yeah. [00:39:12] Joe: Perfect. Well, here’s what I’m wondering is with the big runup, and you’ve been rewarded every single time that you had, that you take a risk, when I read this thing about millennials are more comfortable with risk, I thought, are they, or are they just desensitized to it? ’cause they really haven’t seen a pothole that was longer than just a few months. [00:39:31] Doc G: I think they somewhat get it wrong. And so instead of talking about high risk and low risk, what I’d really talk about is concentration versus diversification, right? Diversification is low risk, usually concentration is high risk. And I was just interviewing Joseph Moore, who’s a wealth historian, and he said, we get it wrong. [00:39:50] Doc G: People tell you when you invest, you should diversify. You said, actually, you should concentrate risk when you are young. And then once you make your money, you diversify so you don’t lose it. So here’s where I think the millennials could be, right? And here’s where they could be wrong. I think we have to concentrate risk, meaning be risky. [00:40:07] Doc G: In our jobs, in the businesses we start in the things in which we use sweat equity. On the other hand, I think where we see millennials this generation getting wrong is they’re concentrating risk in things like cryptocurrency. Something that feels a lot more like speculation than an actual investment that. [00:40:27] Doc G: Could be a higher, low profile risk. So I’d say, you know, yeah, you’re young. Put your monies in equities, which are high risk but not nearly as high risk as cryptocurrency. Maybe a diversified index fund like an s and p 500, but where we really wanna be risky and concentrate our risk, where we’re really gonna make our money is be risky in your career. [00:40:47] Doc G: Like do something innovative, be risky in your side, hustle. Be risky in those places. And starting a business, that’s where if we concentrate our risk, we eventually build the wealth and one day we’ll then diversify and de-risk when we actually have some wealth to protect. [00:41:02] Joe: Yeah. I like this idea of taking risk in your career, and I think we don’t think about that enough, but are you saying when you’re in your twenties, don’t swing for the fences with your investments? [00:41:10] Doc G: I a hundred percent say that. Don’t swing for the fences with your investments, at least when it comes to paper assets. Again, investing your time, your energy, building a company for sure. But when it comes to very high risk assets. I don’t think those are what really build long-term wealth. Certainly it does for a few, right? [00:41:30] Doc G: So if you were early in on some of these big companies or if you were early to cryptocurrency, you built a huge amount of wealth, but the grand majority of people lose not win on that. Whereas if you invest in, again, building a career, building a skillset, or building a business that’s more likely to pay off for you in the long term, [00:41:50] Joe: pays lots of dividends over your longer [00:41:52] OG: career. [00:41:52] OG: I, I would just add to that a little bit. Sometimes when it comes to that concentration doc, it’s like sometimes it happens without you even paying attention, right? If you work for any company, you might have RSUs, you might have company stock in your 401k, they might, you might have ESPP discounted shares that you can purchase, and so you take advantage of those things, or you have non-qualified options and you take advantage of those things. [00:42:14] OG: On the other side of it, if you don’t manage that concentration, or at least have a plan for it. What we see sometimes is, you know, you wake up 10 years later and yeah, you work for a company that was even take out the ones that are like wildly successful. Just ones that have stayed in business and did okay, and all of a sudden you’re going, oh crap. [00:42:33] OG: Now I have all this money tied up in this company, which is good. It’s been, it’s paid off. However, now to do something with it, I gotta go pay Uncle Sam 25 cents on the dollar to like unwind some of these transactions versus like having a strategy going into it, managing that, managing that concentration risk, like you said, throughout your whole life cycle. [00:42:53] OG: Sometimes it’s unavoidable, right? Right. You get a stock grant and you know, you hit home run, right? You got, but nobody’s mad about those. It’s like, you know, oh shucks, I gotta give, [00:43:02] Joe: oh man, [00:43:03] OG: uncle Sam, two and a half million of my 10. Like, darn, you know, they still, everybody still complains about it, by the way, but it’s still like a pretty cool problem to have if you, if you get it. [00:43:13] OG: But if you’re taking advantage of those resources at your employer. Pay attention to it. ’cause you could wake up in five or 10 years and then you’ve got that. Problem, but you’ve got a something to deal with. [00:43:24] Joe: I do love this idea of investing in your skillset though in your twenties. [00:43:28] OG: Absolutely. [00:43:28] Joe: And especially right now when we’re seeing the skillset that’s needed changing with AI coming to bear on some places that used to be the hot jobs. [00:43:37] Joe: Now you’re seeing that begin to rotate, uh, as it always does, but seems to be doing a little bit quicker today. Pretty interesting. The next one on this list, Jen, is when I really think of you millennials, I think of this one, which is this idea of multiple income streams. You can’t not think of the early, well maybe like 2005 into 2020 and not think of the birth of people having all these very quick second jobs that you can all of a sudden pick up driving Uber or whatever the case may be, starting an Etsy shop doing all these different things. [00:44:13] Joe: There’s been some pushback on that lately, hasn’t there been? I, I feel like as millennials get older, they’re like, dude, maybe, uh, this wholesale culture isn’t, isn’t all as cracked up to be. [00:44:22] Jen: Well, I mean, it’s been 10, 15 years, right? When these side gigs started becoming popular. We needed them because there weren’t a lot of jobs for people without experience. [00:44:34] Jen: They’re arguably still are not. And now it’s 10, 15 years later and we’re married, we’ve got kids, we’re already tired. We don’t have time for side hustles. And I think we’ve seen a lot of our peers who have hustled nonstop get burnt out. So I think there’s a time factor to it, but we’ve also seen our parents or other peers lose their income, which I think is why investing in skills and taking risks in starting something on your own, it doesn’t have to be like a risky business. [00:45:09] Jen: For lack of better term, but it does have to be something that protects you, that if you lose your job, which is very normal, we saw a lot of job loss last year that you can have something to fall back on. I lost my job when I was seven months pregnant back in 2019, and I was fortunate enough that, uh, as a finance writer, I could fall back on freelance writing even though I lost my full-time job because I invested in my network, which I think that’s an investment not enough. [00:45:38] Jen: People are talking about is investing in knowing people, meeting people, building relationships with other people in your community, in, in your field, because those are how a lot of jobs come up for people. You don’t get into a job through the front door anymore with people getting a thousand, you know, resumes. [00:45:59] Jen: You get these side jobs and these main jobs through knowing people. [00:46:03] Joe: I had a breakfast meeting a couple weeks ago, Sarah Catherine Gutierrez, who some of you know, and she has been a contributor to this podcast. Sarah Catherine lives up the road in Little Rock, introduced me to this young woman graduating from a local university who wanted to network. [00:46:18] Joe: So number one, she already knows Sarah Catherine Gutierrez, who can introduce her to a lot of really great people. She then has breakfast with me in Texarkana. She already knows the guy that won Citizen of the Year Award locally, he’s the president of the local bank. She, uh, did an internship with him like Jen, to your point, she’s 22 and she’s already doing something I don’t see 40 year olds do. [00:46:40] Joe: She knows everybody. She already is on her way to knowing the right people. Now, it doesn’t mean she’s not gonna have to hustle, but I think it’s a, it’s a combo. You’re, you’re looking at me, doc, like, yeah, this, this networking thing, you know, it’s cracked up to be. [00:46:53] Doc G: No, I agree with that. I’m, I’m rolling my eyes more that I think we’ve overplayed this multiple revenue things stream thing. [00:46:59] Doc G: I think it’s, I think I will put my foot down. I think most people are fully, when they talk about this, why are they fully, because your average professional has four revenue streams right off the bat and could get to six without a problem, without even thinking about it. So why does your average person have four revenue streams off the bat? [00:47:14] Doc G: So if you have 22 and you’re in corporate America, you’ve got your income, which is your skillset, right? That’s one revenue stream. If you’re putting money into your 401k, you’ve got equities, which is another revenue stream. You might have some bonds, that’s another revenue stream. And you have social security. [00:47:29] Doc G: So right away you have four revenue streams. Yes, you’re 22. You’re not gonna collect social security till you’re in your sixties, but you’re already building your social security, you’re building your investments, et cetera. You might have a house. Easy revenue stream. If you ever want to rent a room, anyone can do Uber. [00:47:45] Doc G: So you have another revenue stream there if you really want it. And guess what? Almost everyone has the revenue stream of selling things on eBay and putting things up on Facebook marketplace. So this whole idea that we’re supposed to have all these revenue streams makes people really anxious and they actually take away or don’t devote as much as they could to their primary income, which is their skillset or their job or their career. [00:48:07] Doc G: If you like your career, do that. Stop worrying about multiple revenue streams, you already have them. [00:48:13] Jen: I think that’s a great point. For years, I really divided my focus on all of these side hustles. ’cause I was kind of positioned to do that, like while we were paying off debt. And then I missed out on a lot of opportunities in the places I was passionate about because I was worried about a quick dollar versus a dollar that could grow through like my primary way of earning money. [00:48:38] Doug: Would that be procrast to earning, [00:48:42] Jen: procrast to spending my time. Busy work? Not all. Not all Action is progressive action. It’s a lot of the times it’s distraction. [00:48:50] Joe: Well, and that is interesting because on one side, og, like I hear what Doc and what Jen are saying, and frankly this is something that I said a bunch and I’ve been quieter about lately because of the fact that I always thought, man, you could just get good at the thing that you’re doing gets almost Steve Martin, right? [00:49:06] Joe: When he said be so good, they can’t ignore you. So even if you lose your job, Jen, to your point, even if you lose your job, you’ve got enough network inside of that area that everybody knows you, likes you, and bam, you land another one very quickly. But there’s still og there’s this risk that if I don’t have this other income stream already built yet, that I might have to swim this moat. [00:49:26] Joe: Like where do you stand on the whole side hustle versus just focus on one continuum? [00:49:33] OG: It wouldn’t be fair for me to say that I stand on one when I do a lot of things that generate money, some of it more successfully than others, but I do think that if you’re an expert in a particular area, it becomes easier to spin off into ancillary things. [00:49:50] OG: Or you have the network to do consulting, for example. Nobody cares to do consulting with somebody that hasn’t been successful. Like that’s not a, like I consult to small business owners on marketing. The first question is, how’s your marketing? It’s like, oh, I don’t have a business or do marketing, but I consult to you. [00:50:09] OG: You know? It’s like, okay. [00:50:11] Joe: I had somebody market me recently saying they can help us with our X following, and so I went and looked at their X following and they had like 3,200 followers. [00:50:20] OG: Yeah. And that’s a lot, but not [00:50:22] Joe: consulting [00:50:23] OG: a [00:50:23] Joe: lot, but not enough to be telling me what to. [00:50:25] OG: Yeah. Yeah. So I definitely think that it’s good to have other things. [00:50:29] OG: I, I think personally for me, I, I found that the stuff that I like doing also turns into opportunities to earn a few extra bucks, but it’s not anything that is gonna produce, like, you know, pay the mortgage type of money. It’s more of like, you know, just kind of extra fun stuff. But if you’re not topped out at where you are, if you’re not the go-to person in your career or the go-to person in your office, heck, you know, you probably should be spending some time and energy trying to work on that. [00:50:56] Joe: Does somebody’s cat need help? [00:50:58] OG: Yeah, that’s mine. My, well, not mine ’cause it, everyone knows how I feel about it, but it’s, um, my daughter came home and she went to the bathroom, but the, the cat is not excited by the fact that she shut the door to the bathroom. [00:51:11] Joe: Yeah, I thought that we had a new star of the show on Stacky Benjamins. [00:51:15] Joe: Uh, let’s move into this last one just briefly, because also the world of ESG kind of exploded during millennials, uh, uh, coming into the forefront of investing. And we’ll start with you, Jen. I feel like initially this idea of investing with your values is a great thing. And then I saw all these companies get on board and then we start looking under the hood. [00:51:39] Joe: And for a lot of companies it’s talking the talk, but it’s, it’s truly not walking the walk. [00:51:44] Jen: Yeah. It’s hard because a lot of people aren’t gonna look under the hood. They’re gonna trust the experts to say, oh, if this is a social justice or sustainability. Driven fund that it is what it says it is. And so it’s unfortunate that something that could have been like really good got tarnished so quickly by some bad players. [00:52:07] Jen: It stinks. And so I still know of, like my friend Laura Alain, she helps people invest kind of outside of Wall Street, like using self-directed IRAs for like investing in Main Street, you know, stuff like that. There are still options. I think they’re kind of like 2 0 1 level, like definitely not something that I would start with a little, yeah, don’t with any of that. [00:52:33] Jen: More complex and more risky. And then you’ve got other people who have diverted to maybe doing more real estate. So there are other options, but it, it was such a, like a bummer that something that could have been so good is now has a really bad vibe around it. [00:52:50] Joe: Yeah. Some, some not the same connotation that it had for a while. [00:52:54] Joe: Doc, you like having these philosophical arguments. You and I have had these discussions at Camp Fives before. Should your investments reflect your personal values or should you just look to maximize returns and then have your values outside of your investment portfolio? [00:53:11] Doc G: I think the answer can be either. [00:53:13] Doc G: Part of the problem is I truly believe when you try to invest your values, it’s much, much harder to get the same returns. It’s really hard over long, sustainable periods to invest, for instance, in ESG funds and have them return what the s and p 500 does. The other problem with that is, is the ESG fund really ESG, when you go under the hood, is it really what you think it is? [00:53:34] Doc G: I think you have to put your foot in the sand and just decide what’s more important to you. Like if staying consistent with your values to the greatest extent possible is more important with you, I think you have to accept lower returns and that’s totally fine, and look into it and study it because this is important to you, et cetera. [00:53:51] Doc G: I think if you’re, on the other hand, you’re like, I want to be a wise investor that gets the highest returns. Realize that there are occasions where you may, you know, be involved in a fund that supports, let’s say big tobacco and maybe you don’t believe in that and you believe they’re cancer sticks, but they’re part of an avidly growing portfolio and it is what it is. [00:54:09] Doc G: I think you just have to decide what fits and feels right for you. Even though even within that though, there are decisions, right? You can decide, well, where am I gonna invest through? Maybe I am a big fan of Vanguard because I like what they stand for, and so I’ll put my money in Vanguard and not Fidelity. [00:54:29] Doc G: Even if their computing system and their online portal isn’t as good, maybe I feel like what they stand for is better. So I think you can make some of those decisions and get some equivalent endpoints, right? ’cause you can invest through Fidelity or Vanguard. You’re gonna do fine either way. I think it gets harder the more you really wanna be a stickler about only putting your money in places that follow kind of your ethical dictates. [00:54:53] Joe: We have seen lately for a while, OG that, uh, ESG investments actually were leading the way for a while, and some people even said maybe that’s gonna continue into the future where companies are driving returns by doing the right stuff. Do you think we can really, you know, you’ve heard the phrase, can we, we can do well and do good consistently. [00:55:15] Joe: Is that, is that really a thing? Do you think we really can. [00:55:20] OG: Oh, I’m, I’m snickering here to myself because I, I wondered if this fund still existed and it does. It’s called the vice fund and the headline image, the hero image on the website is a dude gambling with a glass of whiskey. [00:55:33] Jen: I’d love to know the returns on that. [00:55:35] OG: Uh, 21% last year. It invest in, I bet, alcohol, defense, and aerospace. Gaming and tobacco. That’s the only thing it invests in. So it’s like literally, basically it’s like a Saturday night with Doug. That’s what you are investing in. [00:55:51] Joe: Maybe [00:55:51] OG: we should [00:55:51] Joe: call it that, the Saturday night with [00:55:53] Jen: Doug. All the prediction markets. [00:55:54] Jen: Yeah, all the prediction markets. [00:55:56] OG: So here, here’s my take on this. I, I don’t have a dog in the hunt. I think that if it’s like Doc G said, if it’s something that’s super important to you, I think you should go after it and you should do what you think is best for you. I don’t know whether or not it’s fair to predict into the future that this type of investing will do better or worse than that type of invest. [00:56:17] OG: I don’t know that I could prove that to anybody in advance. But my question always, just ’cause I’m a little bit of a cynic when it comes to stuff like this, is like, where do you draw the line? I’ll just use a a very open example that happened here recently. We just saw the news about Claude and Chat GPT and one company said, I don’t even remember which was which, but one said, Hey, we’re gonna do it our way to hell with the government. [00:56:41] OG: And one person, one the other one said, well, if you guys don’t want the contract, we’ll have the contract. What do you want us to do? And so some people may look at that. Now, neither of these are publicly traded companies, but you know, you might look at that and say, well, I’ve got a feeling about this one way or the other. [00:56:55] OG: Does that make you change your opinion about investing in either of those companies? If you take a, an example of, uh, or, or a company like, um, Nvidia, you could say, oh, well they’re doing a bunch of really good things with technology and that sort of thing, but they’re also using a bunch of energy and. [00:57:13] OG: Clear cutting forest to build all these, all this infrastructure that they need to run their organizations, which may be a good thing eventually or a bad thing eventually. I don’t know. Like, you know what I mean? Like you, it’s hard to, in my opinion, to firm out like always or nevers because there’s so much nuance there. [00:57:31] OG: If there’s some things that are like very particular like religious belief and say, Hey, I can’t, in my soul, I can’t do this, then that’s totally fine. And whether or not that leads to different returns, so be it. Like who cares? [00:57:44] Joe: I wanna ask you technology wise, because it’s been about a year and a half since we spoke with a gentleman from Vanguard, I’m not gonna get his name. [00:57:50] Joe: He was talking about the technology OG that we’ve seen coming around where we can take an s and p 500 fund or a total stock market fund and we can take stocks out just for us. We can say, I’m gonna do the total stock market, but not invest in this stock or this stock and this stock. And I know on some level people can do that with separate accounts. [00:58:10] OG: Yeah, [00:58:11] Joe: absolutely. But, but there’s gonna be a more mass marketization of that. Mm-hmm. Coming online. How far away do you think that is for the average stacker? [00:58:18] OG: Well, I, I mean, you could do it right now if you wanted. I mean, I’m, I I’m talking about like automate it and Yeah, obviously you could do it, you could literally pick your own stocks. [00:58:26] OG: But I’m saying like you can buy a pre-packaged product and say, exclude this stuff and automate it from here. Yeah, you can do that right now. There’s probably some limitations. [00:58:33] Joe: Yeah. [00:58:33] OG: In terms of minimum account size, I. And then you have to decide whether or not that’s again, back to, is the juice worth the squeeze? [00:58:41] OG: Right? Like, like what are we talking about? If you’ve got a hundred K in your brokerage account and you’re comparing it against the Russell 3000, each one of these stocks has 300 bucks in it, and you’re gonna say, I want to exclude these four because I don’t want to do that. Like, okay, like what? What are we doing? [00:58:57] OG: It’s you’re creating a rocket ship to like eliminate $1,200 from your portfolio of investing, you know? Yeah. And [00:59:06] Joe: yeah, [00:59:06] OG: I don’t know. I’ll play that game a little bit with people, but the reality is, is that it’s not my job, nor is it our job, any of our jobs, to tell people how they should feel about investing. [00:59:17] OG: It’s really just to say, here’s the roadmap for what is the way for you based on what your values and beliefs are. And to support it however we can. And if that turns out by the way that it’s lower returns again, so be it right then that, then that just changes your plan a little bit, right? So you just save a little bit more money or you work a year longer or something like that. [00:59:39] OG: It’s not the end of the world one way or the other. But if it’s important to you, you gotta get after it. [00:59:43] Jen: I have a hot take on the question. [00:59:46] OG: Oh, [00:59:46] Jen: let, let’s do it. I don’t think that you’ll be able to get as high of returns. I don’t think the whole do good and make good and [00:59:55] Joe: do well. Yeah. [00:59:56] Jen: And do well is sustainable long term. [00:59:58] Jen: ’cause Think about how do companies make money? How do stocks increase in value? There’s higher profits and companies do prioritize profits for that reason. And we’re seeing it in shrink inflammation, skimp, ifl, uh, social media over consumption halls. And I think that is doing more damage to us than. Us not investing or investing in sustainable funds or or whatnot. [01:00:28] Jen: I think if we all did do this, like the ethical thing, you know, like consume less, consume better, companies would not have as good of returns. They would not have as high of profits, and then the returns would be. Not as good, but that’s just like my hot take. [01:00:47] OG: Jen, I heard an interesting take on this, which was no, your job, if you disagree with something, is to make as much money as you possibly can so that you can dedicate enormous amount of resources in the future to getting rid of that thing that you don’t like. [01:01:01] OG: It’s like, so I’ll show them, you know, which has some, has some validity to it, right? I mean, like, you know, all the like political capital, right? It’s how much money goes into political campaigns? Who does it? Is your $400 contribution to such and such a political campaign gonna earn you a seat at the table? [01:01:19] OG: No, it doesn’t. It’s the $400,000 one that does, or the 4 million and now 400 million, [01:01:25] Joe: right? [01:01:25] OG: You know what I mean? How do you eliminate it? Well, you make a crap load of money and then go, now I’m gonna, now I’m a gazillionaire as, uh, what’s his name said Forrest Gump. [01:01:32] Joe: We got primaries coming up here, and as you know, og uh, somebody on one of my social media pages said, you know, by the sixth mailer you send, that looks exactly the same. [01:01:43] Joe: We probably already know who you are, and there was no reason for you to send that. And yet we, we just get in. It’s so much money wasted. It’s so frustrating. We’ll link to this piece on our show notes page at Stacking Benjamins, this [01:01:55] OG: article. Yeah. Are you gonna link to the article? [01:01:57] Joe: It’s a piece. We’re link to the piece. [01:01:59] Joe: The piece, but not the article is the piece of [01:02:00] OG: the article. [01:02:01] Joe: Yes. This is Jen’s favorite part of the show where we, uh, argue with the wording around it. Is it an [01:02:06] Jen: article or a piece? [01:02:07] Joe: It’s a piece. It is a piece from Kiplinger [01:02:10] OG: from the article. Kiplinger? [01:02:11] Joe: Yes. On our show notes page at stacky Benjamins dot com. [01:02:15] Joe: Jen, get us outta this. What the hell is going on at Frugal Friends that we can brag about to all our other stacker friends. [01:02:21] Jen: Oh wow. We just had an episode come out called The Man Responsible for Why You’re Broke. [01:02:26] Joe: It wasn’t me, I swear to God it wasn’t [01:02:28] Jen: me. It’s a deep dive into this guy named Edward Bernas, uh, who actually is responsible in the 1920s for getting women to smoke more and how his book propaganda has impacted the marketing for the last hundred years, and, uh, may be responsible for some of the reason why you’re overspending. [01:02:47] Joe: I love those history lessons. They’re so fun. And you’re like, maybe this is older and more time tested and thought about than I thought. It’s [01:02:53] Jen: crazy. [01:02:54] Joe: And that’s at Frugal Friends where the fine, wherever the finer podcasts are found. [01:02:58] Jen: YouTube, Spotify, apple, wherever you get your podcasts. But we do put some fun images and social videos and stuff up on YouTube. [01:03:07] Joe: Awesome. We’ll link there in our show notes. Doc G, what’s happening at Earn and Invest this Fine week in March? [01:03:14] Doc G: Well, I already mentioned him. I am talking to wealth historian Joseph Moore. We talk about everything from like, what the heck is pecuniary independence to how house hackers have always been around. [01:03:27] Doc G: And it’s not a new concept. People have always been having other people live in their houses. To even something that I never heard about. Great, great piece of trivia. This idea that we are always talking about, well, if you had been invested in the full market since the 19 hundreds, this would be your return. [01:03:41] Doc G: But back in the 19 hundreds you couldn’t even buy a stock without basically purchasing somewhere between, in today’s dollars, five to $10,000 worth of stock. You couldn’t just buy like a hundred dollars worth of stock. So the way that people invested were these places called bucket shops, where there would be a ticker of the stock market and people would place side bets in the bucket shop about what would go up or what would go down. [01:04:04] Doc G: And that’s actually how most Americans who invested in the stock market, it was the only way for them to invest in the stock market at that time. ’cause most people couldn’t afford the five or $10,000 to buy. The minimum amount of stocks you could in a company to be part of the actual stock market. [01:04:17] Joe: It’s amazing how what’s new is old, that now we’ve got these new ways to bet on anything you want. [01:04:22] Joe: We can bet on any, we can bet on the weather, bet on whatever we want, and yet you could do it way back in the day. [01:04:27] Doc G: Yeah. Cool stuff. [01:04:28] Joe: Wow. So it’s contributor History Week. It sounds like. Frugal Friends with a History show, earn and invest with a history show and earn and invest where only the finest podcasts are are found, I think. [01:04:38] Joe: Right. And you can read Jordan Substack as well. [01:04:41] Doc G: Yeah. Jordan grommet.substack.com. [01:04:43] Joe: Always good reading. Og what’s going on at the OG household this weekend besides, uh, you and your cat screaming at each other? [01:04:49] OG: Oh, uh, bicycle. I will be riding my bicycle over and over and over again nonstop. That is all I do now. [01:04:58] OG: Every time you ask me, I will be saying I am riding my bicycle as I get ready for this. Little, little event. [01:05:04] Joe: He’s going, he’s riding over a hundred miles in the mountains. In the mountains of Colorado, Jen. Ooh. I know, right? [01:05:10] Jen: Mountains. Nope. [01:05:12] Joe: Yeah, [01:05:12] Jen: you lost me there. [01:05:13] OG: A common follow up question would be, oh, you must have done this a lot. [01:05:17] OG: No, first time. [01:05:19] Joe: Yeah. Oh, ride a hundred. It’s the [01:05:20] Jen: first time for everything. [01:05:21] Joe: He, he could ride it on someplace flat, but No, he’s gotta go. [01:05:24] OG: Yeah. Like doctor, you said, oh, so a hundred miles. How long’s your longest? I’m like, uh, like 20 something [01:05:30] Joe: like three. [01:05:32] OG: Good. Good. [01:05:32] Joe: Yeah, he’s, he’s thinking about replacing the banana seed on his bike too. [01:05:36] OG: I was gonna say, the little tassels are pretty cool, [01:05:38] Joe: right? Yeah. [01:05:39] OG: Be time to upgrade ’em. [01:05:40] Joe: Alright, stackers. That’s gonna do it for today. Hey, we record these on Monday. It’s always fun talking about Friday, when it’s actually Monday when we record these. We do it on YouTube on Monday afternoon, so come join us. [01:05:51] Joe: Generally three 30 Eastern time. That would be one 30 Pacific. So come join our live recording and thanks to everybody who helped, uh, Eric, Shane, uh, Andrea, lots of people contributing today. Grace Drew, Rob so many people. Thank you so much for making it a fun hangout here on YouTube on Monday. We will be back speaking on Monday with a full new slate of shows. [01:06:15] Joe: But until then, Doug, tell them what we would’ve learned on today’s episode. [01:06:20] Doug: Well, Joe first take some advice from Doc G. Don’t fight the algorithm. When you’re automatically opted in for savings at your new job, just drink the Kool-Aid and let it happen, man. Second, don’t forget about Jen Smith’s new four letter word procrast to spending. [01:06:37] Doug: Actually, it’s 17, I counted. That’s spending money on stuff and not getting the benefit of that thing. Gym memberships, don’t do that. Just buy the pizza. Eat the whole thing right away. That way you’re not procrastinating. [01:06:50] Joe: No. You get right to it. Yeah, [01:06:52] Doug: yeah. Just get right at it. But the big lesson, don’t tell Joe’s mom that NASA’s gonna probe Uranus in 2044. [01:07:00] Doug: She’ll start swinging her big wooden spoon around. I don’t think that probe’s gonna reach ma. [01:07:09] Doug: Thanks to Jen Smith for joining us today to learn more about Jen and her frugal friends. Oh, they sound like tons of fun, Jen. Check out frugal friends podcast.com. We’ll also include links in our show notes at Stacking Benjamins dot com. Thanks to dot G for hanging out with us today. Be sure to check out his insightful podcast. [01:07:28] Doug: Earn and invest wherever you listen to finer podcasts. And finally, thanks to OG for joining us today. Looking for good financial planning help and a hell of a trivia player. Head to Stacking Benjamins dot com slash OG for his calendar and cheat sheet, [01:07:44] opener: not cheating. [01:07:46] Doug: How else can you be winning by a hundred? [01:07:49] Doug: This show is the Property of SP podcast LLC, copyright 2026 and is created by Joe Saul-Sehy. You’ll find out about our awesome team at Stacking Benjamins dot com. Along with the show notes and how you can find us on YouTube and all the usual social media spots, come say hello and oh yeah, before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. [01:08:16] Doug: This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I’m Joe’s mom’s neighbor, Doug, and we’ll see you next time back here at the Stacking Benjamin Show.
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