Want to make your financial life easier? Automation is the key to staying ahead—if you do it right. In today’s roundtable discussion, Afford Anything’s Paula Pant, Best Interest’s Jesse Cramer, and Earn & Invest’s Jordan “Doc G” Grumet join us to explore how automating your money can remove stress, prevent costly mistakes, and help you build wealth without even thinking about it. But is there such a thing as too much automation? We’ll break down what to automate, what to double-check, and the financial tasks that should always have a human touch.
Together, our panel dives into how automation impacts savings, bill payments, investing, and even everyday productivity. From tripwires that catch hidden charges to smart systems for managing cash flow, this discussion is packed with practical takeaways. Plus, Joe shares a cautionary tale about automation gone wrong—one that left him unknowingly driving without car insurance.
And, of course, what’s a Friday show without Doug’s trivia? Today, he has a burning question related to our topic of automation and AI. With OG’s lead in the yearlong competition at stake, will Paula, Jesse, or Doc/O G inch closer to victory? Tune in to find out!
FULL SHOW NOTES: https://stackingbenjamins.com/everything-automation-1641
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Watch On Our YouTube Channel:
Our Topic: How automating your finances can help you stack more Benjamins
During our conversation, you’ll hear us mention:
- How and why automating makes sense.
- Simple financial tasks that should be automated.
- Automating payments.
- Automating savings.
- Automating investments.
- Max out your retirement savings automatically.
- Once-and-done decision-making.
- Free your mental bandwidth up for other important decisions.
- What’s “important” vs. what’s “urgent.”
- Stress avoidance.
- Set-it-and-forget-it.
- Free yourself up for what’s truly important to you.
- Focus your time on areas where you’re truly talented.
- Where automation doesn’t make sense.
- Automation of expenses but periodically review them.
- Risk mitigation.
- The human element.
- Strategically not using automation to “feel the pain” of bad habits.
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Jesse Cramer
Another thanks to Jesse Cramerfor joining our contributors this week! Hear more from Jesse on his show, The Best Interest at The Best Interest – Complex Personal Finance Made Easy Podcast Series – Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Doc G
Another thanks to Doc G for joining our contributors this week! Hear more from Doc G on his show, Earn & Invest podcast at Earn & Invest on Apple Podcasts.
Check out his latest book The Purpose Code: How to unlock meaning, maximize happiness, and leave a lasting legacy.
Paula Pant
Check Out Paula’s site and amazing podcast: AffordAnything.com
Follow Paula on Twitter: @AffordAnything
Doug’s Game Show Trivia
- How many reports of identity theft did the FTC receive last year?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday when we welcome the perfect wallet therapist to restore your relationship, Certified Financial Planner Shannah Game.
Miss our last show? Check it out here: Yet Another Insurance To Avoid (SB1640)
Written by: Kevin Bailey
Episode transcript
[00:00:00] bit: So faced with the question, where did they go next with this podcast? The guys were recently joined by legendary musical genius, Bruce Dickerson, who’s agreed to be the new producer of the Stack and Benjamin Show. They were all excited to meet him. Hey fellas. I’m Bruce Dickerson. Yes, the Bruce Dickerson. [00:00:26] You have a dynamite sound. Fantastic sound. I have only one suggestion. [00:00:35] More cowbell. [00:00:49] Doug: Live from the basement of the YouTube headquarters. It’s the Stacking Benjamin Show. [00:01:05] I am Joe’s Mom’s Neighbor, Doug, and let’s get your money factory cranking. What did we learn from the automobile that applies to your money automation? Today we’re sharing what to automate, what to put on hold, and where the biggest ROI gains can with your money if you nail this. But that’s not all Today. [00:01:24] Our panel will try and regroup to ensure that OG doesn’t run away with our year long trivia challenge. Then now a guy who’s here to help you parse the trivial from the important parts of financial planning. It’s Joe Saw. See? [00:01:43] Joe: Hey everybody, and happy Friday to you. We’re super happy you’re here to talk. [00:01:47] Automation with us and the people that are with us are not automated. They’re animated, but not automated. Starting with a woman who’s coming to us, not from Manhattan, but I believe from her old bedroom in Georgia. [00:02:00] Paula: Mm-hmm. [00:02:01] Joe: Paula Panta is here. [00:02:02] Paula: I am here. I am automatically smiling by virtue of being in your presence. [00:02:07] Oh, yes. Every day is a good day that I’m on the Stacking Benjamins podcast. That [00:02:11] Joe: is fabulous. You just wanted to have a sofa in your background too, like me, didn’t you? [00:02:14] Paula: Yeah, you know, it’s nice. I’m sitting on the floor in front of the sofa, which is technically not how sofas are supposed to be used, but I’ve discovered that the sofa makes for a really nice background, a good depth of field, a nice bright pop of color. [00:02:29] So, yeah. So you got your legs [00:02:31] Joe: folded, like your [00:02:31] Paula: third [00:02:31] Joe: grade camp. [00:02:33] Paula: Oh, I could. Alright, now I do. There we go. Perfect. There we go. [00:02:37] Joe: Yes. And the guy who always loves, uh, being the third grade camp, that’s so bad. Jesse Kramer for the best interest podcast is here. How are you? Man? [00:02:49] Jesse: That is pretty bad. That is pretty bad. [00:02:51] I was gonna make a joke and say like, you know, the whole like leg crossing thing, I don’t bend that way personally. But, uh, yeah, after that, Joe, I don’t know, I might have to rescind my participation in this, in this podcast. You [00:03:02] Joe: know, he’s like a kid. You have, did you go to We didn’t have third grade camp. [00:03:06] We had fourth grade camp. [00:03:08] Jesse: I grew up really rural and so like the idea of going away to camp, I, I live in the woods, like, why, why do I need to go to camp? So, yeah, I never went to, yeah, we can camp right out behind the house. I, I went to a baseball camp once ’cause I, I played baseball growing up, so it was at one of the local colleges in Syracuse. [00:03:23] And uh, you know, you spend like three days there doing drills and you sleep overnight in the dorms. That’s the closest I ever got to camp. It was a fun, uh, it was, I remember that was the first time where I remember thinking, whoa, there are a lot of really good baseball players my age. And I’m, I was from a really small pond. [00:03:40] The place where I grew up is kind of like living in a pond. As I said, it was pretty rural. But yeah, it was an eyeopening experience at how big and talented the world is. [00:03:48] Joe: It made me laugh, Jesse, when I would talk to parents and like, oh, my kid’s seven. He’s a phenomenal swimmer. Like he’s gonna like win the Olympics or something. [00:03:55] Right? Right. Like, your kid doesn’t even hit puberty yet. You have no idea what’s gonna happen. Everything’s gonna change that [00:04:00] Jesse: code for my son hasn’t drowned yet, so he is a phenomenal swimmer. Right. [00:04:04] Joe: That was coded. Our family, actually, that’s the reason why our family did do swimming was they were failing outta YMCA swim camp. [00:04:11] And one of our friends for her kids, she’s like, I just had to join the swim team for one year. I didn’t care how they did, I just wanted to join the swim team. And they learned how to swim fast. And it was, it was, it was great. I’d recommend swim team for everybody at least one time, and the guy who’s gonna swim through this topic of automation is here. [00:04:28] Doc g Jordan Grumet joins us. How are you man? [00:04:31] Jordan: I’m doing well. You know, my mom used to automate childcare or in the summer she’d send us all to sleepaway camp and just get rid of us. Perfect. So that was, that was the best automation. I don’t know if I can top that. So you went to camp all the time, like you’re the opposite of Jesse. [00:04:45] You were. We did day camps when we were little, and then when we got old enough, we all did sleepaway camps, so I’d be a month or two away from home. Well, [00:04:52] Joe: I definitely don’t [00:04:52] Jordan: want [00:04:52] Joe: you guys to sleep on this topic because I’ve been on record as saying that this topic is really for me, the number one way to get ahead with your money. [00:05:02] Is to automate, make saving easy. And if you nail this, if you get this right, man, the rest of it just goes so, so, so much easier. If you’re brand new to our Friday episodes, I wanna welcome you, especially because what we do with our team of contributors, we take a topic of the news, we discuss it. I will tell you this, our Friday shows are never super hard hitting. [00:05:25] It’s much more like sitting around with a group of friends and you’re at lunch and they’re super smart with money so you can be too. Something we always do each week too is thank our sponsors right at the top of the show. We’ve got a couple here that make sure this is free and we can keep on keeping on. [00:05:40] So we’re gonna hear from them and then these brilliant people are gonna help you get better at automating your money. [00:05:52] This idea of automating your money. I said, Paula, in my intro that I thought this was the number one thing to do to get ahead. Let’s really expand on why. Why should we care about making sure we nail automation? [00:06:06] Paula: Frankly, it’s because we’re all busy. There are a million things that we have to do, and there are certain tasks in our life that simply can’t be automated, like doing the laundry. [00:06:15] Our cognitive capacity is limited. We’re juggling a million different things every day. We’re going to work. We’re, we’re making food, we’re trying to maintain our lives, and it’s so easy for financial tasks to slip through the cracks. Even bill paying, which incurs penalties. It’s easy for that. With something relatively short term with a penalty, it’s easy to forget to do that. [00:06:40] So you can imagine how much easier it is to forget to do the things that don’t have penalties and that are long term like investing. [00:06:46] Joe: Yeah. Jesse, back when I was a financial planner, to Paula’s point, I had a client who made the equivalent today of about half a million dollars a year. This is back in the late nineties. [00:06:55] She had a horrible, horrible credit ’cause she kept forgetting to pay her bills. I mean, she, she was just so busy with her career at the television station that all the other stuff went in the trash. Why else should we care about automation besides that? [00:07:10] Jesse: The one thing that came to mind for me is that automation allows you to make sure that you’re doing. [00:07:16] All the important stuff. And, and I guess what I’m saying is that if you don’t automate, a lot of times it’s gonna be like the squeakiest wheel is going to get your grease. And, and just like Paula said, a lot of times that squeakiest wheel is gonna be like, oh shoot, I just got a letter in the mail from the utility company that I’m late. [00:07:33] Or like, oh shoot, I, I just realized I’m, I’m a couple days late on my mortgage payment. And so you’re gonna, you’re gonna do things like, you’re gonna make sure your pay your bills, but the things you’re gonna forget is like, oh, right. Uh, I didn’t max out my Roth, IRA contribution last year and I have till the tax deadline to do that, but that is just gonna completely go past your mind if you don’t automate it. [00:07:52] So to me, automation, right, it’s that we can come back to this term later, the idea of decision fatigue and, and you know, you can just opt to make one decision one time, which is to set up an automation. Then save yourself from ever having to make a hard decision or any decision. Again, [00:08:08] Jordan: doc, you’re nodding your head. [00:08:09] Yeah, I mean, decision fatigue is exactly what I was thinking. And so put aside the ease that we just talked about. ’cause that’s really, really true. But you guys already mentioned it. When it comes to making money decisions, they’re deeply emotional. Like, do I max out the 401k? Do I put money in the Roth ira? [00:08:25] Do I put money aside for Juniors College? All of these are really big decisions, and if you find yourself having to make them every month, it’s just painful. So I love this idea of kind of making the decision once and then letting automation take over so you don’t have to keep on re-litigating the case. [00:08:41] And I think that’s really important. Like if you can automate some simple stuff like this is my fun account, this is the college account, this is my 401k account, and all that gets automated. You don’t have to keep on making those decisions about how much and when. [00:08:55] Joe: I love this idea of opening yourself up to focus on what’s important versus what’s urgent. [00:09:01] Jesse, I mean, completely to your point, like we get caught in these urgent forest fires all day if we don’t automate the well, regardless, right? Regardless, to some degree, part of our day changes is the day goes on based on outside stimuli, and if I haven’t automated the super important stuff, well then I’m gonna run into, run into a bunch of trouble. [00:09:23] Yeah, I think that’s [00:09:23] Jesse: huge. I think like, this is a weird analogy to make, but if you follow me, I hope it makes sense, which is if you’re the kind of person who is chronically late, even when there’s something like, oh, I, I have a hair appointment and I’m running 15 minutes late and I’m super stressed. This [00:09:38] Joe: happens to Jordan and I all the time, always, I’m [00:09:40] Jesse: sorry, always I picked on the wrong topic, but you know, you’ll be super stressed because you’re like, I’m late and, and the barber’s gonna be frustrated at me, and it’s, it’s adding in this level of stress to your life. [00:09:50] That doesn’t need to be there at all. Right? If you are, in this particular case, if maybe you were able to keep track of your time a little better or I don’t have to go down that rabbit hole. I know there are various reasons why people are late, but the corollary is by not automating you are just simply introducing a certain level of stress in your life that we have solutions for. [00:10:08] It’s called automation. It’s completely avoidable and uh, I just think it’s gonna lead to on net, it, it just has to lead to better outcomes for people. [00:10:16] Joe: Yeah, I think there’s a ton of stake here, Paul. If we don’t automate, we just get caught up in this grime of what do I have to do today? [00:10:23] Paula: Yeah, exactly. The more that you can just set it and forget it, the less friction there is. [00:10:29] Right. And the more that frees up your time and energy to focus on other things, so you can focus on elements of your financial life that are not automatable, um, such as decision making, uh, you can focus on, heck, you can just focus on your family life or having fun with your, your friends and the people around you. [00:10:46] You can do literally anything else at that time. Like, why, why would you not, you know, what, what reason is there not to, [00:10:53] Joe: and you know what’s cool Paula? Something that goes along, really, I think with the focus, even with your podcast and you think about your thinking, like, and I’ve learned this at Strategic Coach, which is that you are really good at one thing. [00:11:06] Mm-hmm. Like you have a thing that you’re super good at that maybe a smaller percentage of the world is really good at. Yeah. And the biggest problem most of us have is we don’t spend enough time on that unique talent. Right. One thing that I love about automation is, listen, if I’m not great at it. [00:11:21] Automate it versus, you know, a lot of us spend a ton of time trying to make up for the things that we’re not good at. By turning that two into a good solid five on a scale of one to 10. Mm-hmm. Versus making the nine a 10, I think there’s a huge benefit there to just focusing on that one thing. [00:11:38] Paula: Right, exactly. [00:11:39] Well, you know, you were talking earlier about summer camps and being on this, the swim team and whatever, like if you are an amazing swimmer, don’t try to play tennis, and if you’re an amazing tennis player, don’t try to be a runner. I mean, you can do those things every now and again for fun, but you’re only gonna excel at very few things. [00:11:59] I’m just echoing what you said. The more that we can lean into the, the really unique value that we bring, the unique talents that keep us in the. For which we are the top percentile, the more value that brings not only to our lives, but to the lives of everyone around us. [00:12:15] Joe: Absolutely. We don’t think about that, about man, if we can make an impact on other people mm-hmm. [00:12:19] It’s gonna be with that thing. I wanna go, Jesse, to your, uh, I love what you said earlier, I’ve, I’ve kind of a weird analogy. I’m like, Jesse Kramer with a weird analogy. [00:12:29] Jesse: That’s never happened. No way [00:12:30] Joe: that doesn’t happen. But I wanna dive into that engineering brain of yours, because, you know, when we’re automating stuff, what we should all be doing is, is thinking in terms of ROI, like, there’s 50 million things that I could choose to try to automate. [00:12:44] How do I begin calculating what the biggest ROI is gonna be so I can kinda rank this is the first thing I should automate, second, third, fourth. And this is something I shouldn’t automate, which by the way, I wanna get into that even separately later. What shouldn’t we automate? But for now, how [00:12:58] Jesse: do I calculate ROII have two answers to this question. [00:13:01] And at first I was gonna say, well, you can think about the things that you do most often. And I, I, I don’t think that’s necessarily a bad answer. But I actually think the better answer is I’m channeling, uh, Charlie Munger and his famous principle of inversion, and I think the way we can think of this potentially, and this is the engineer in me, is the, you know, what’s the thing that’s gonna lead to the most catastrophic failure? [00:13:23] If I wanted to implode my life, financial or otherwise, what are the things that I would forget to do? Those can be the things where you might wanna first think about a automating Wow. [00:13:33] Joe: You take like a real risk management approach. [00:13:35] Jesse: A hundred percent. Yeah. And I think that is, I don’t know if it’s the engineer, if it’s aware I was raised, if it’s my investing approach or what, but I do very much take a risk management approach. [00:13:44] And I, I think about the idea of, yeah, you know, what is the worst that could happen? And, and let me try to, to bandaid that first. I mean, do you know this famous story? Can I, can I tell a one minute anecdote about Charlie Munger? I think you have to now. ’cause if I say no, everybody’s gonna be screaming their device. [00:13:57] No, you can’t. Jesse, so Charlie Munger, he, he was a math major at University of Michigan before he got his law degree. And I don’t even think he finished his math major because he got drafted into what would eventually become the Air Force. At the time was just like the US Army Air Corps, and this was during World War ii. [00:14:14] And because he was a smart mathematician, he was basically trained to be a meteorologist, like, look at all this weather data and help us predict the weather for these flights. And so his job was to keep pilots safe on their, their flying missions. And using this principle of inversion, he basically said, if I wanted to kill these pilots, what would I do to kill them? [00:14:33] And the two answers were I would send them up in weather that got their wings so laden with ice that the planes would drop because of the extra weight. Or I would send them into winds that would carry them so far away that they’d run out of fuel and, and not be able to come back. Well, if those are the two ways that in which he could kill pilots, those became the two things that he was most concerned about and that he would spend all his time trying to prevent those two outcomes. [00:14:59] So anyway, it’s, that’s the same kind of risk mitigation principle that we might be able to apply here. [00:15:04] Jordan: You know, it’s funny ’cause Jesse, I look at it the exact opposite. I think of high risk things. I’m gonna be double checking them anyway. I’m going to have some fail safes above automation because I don’t trust automation. [00:15:15] ’cause God forbid something goes wrong. I’m gonna automate low risk, low stakes, highly repetitive things. Things where there’s a lot of friction but they’re low risk. Like that’s where I’m thinking. Whereas kind of the bigger, more important stuff, even if I automate it, I’m still gonna end up going back and doing the work. [00:15:32] ’cause I’m gonna check on that automation and make sure it’s going through because I’m anxious that it’s something high risk. That doesn’t mean you don’t automate the high risk stuff, but it means that maybe automation isn’t enough. Like maybe you automate it, but then you still have to check back in on it. [00:15:45] Yeah. So it’s funny ’cause I think of risk a lot, but I think about it almost in the opposite way that you’re talking about it [00:15:50] Jesse: in your defense. My mortgage payment is automated, but at the same time, at the end of every month when I look at my. Budget software, which is also automated and connect to my bank accounts, I do make sure that my mortgage payment is in there. [00:16:01] Right. So I, I think I pick up your drift. What, what were you gonna say, Paula? Sorry. [00:16:04] Paula: Oh, I, I was actually gonna say that the best approach then can be a hybrid of the two, because where, what I was thinking about was along the lines of the mortgage payment, but a little bit different. When you have an active mortgage payment, you are necessarily automatically paying property tax because that it gets taken out by the bank, like every time that mortgage payment is made. [00:16:25] What happens when you pay off a home and you hold it free and clear is suddenly that property tax payment, which used to be automated, is now no longer automated, and the stakes of not sending in that payment are really high because, no, you don’t have to pay that. The county can seize, literally seize and sell your home, so you can lose a fully paid off home. [00:16:49] Just for not paying like a $5,000 property tax bill or a $10,000 property tax bill, right? So the stakes are incredibly high. And yet here’s this thing that, that a lot of people are not in the habit of doing because it is automated up until it’s not. So everyone’s been taught the habit of never paying attention to it, and then suddenly that changes. [00:17:12] So that’s where I think a blend of, you know, I, I’m, I’m not aware of programs that allow you to continue to automate that property tax payment after the home is fully paid off. If those exist, I would love to know about it. I’m just not aware of any, but that’s where that like. Paranoia has to come in. [00:17:28] Joe: It’s funny, Paula, I had, uh, I had an automation gone wrong, automation run wild back last summer. I pay my car insurance annually and over the last year I changed banks, but I didn’t think about my car insurance. And I have this great software attached to my email called SaneBox, which makes it so I don’t see like 90% of my email. [00:17:53] So SaneBox decided that the notices that I hadn’t made my car payment to my insurance policy, I didn’t need to see those. And I didn’t see them. And so it’s funny because like just, just, uh, uh, I don’t know, December rolls around and Cheryl and I are having one of our weekly meetings and all of a sudden we just go, you know what? [00:18:13] I haven’t seen the car insurance yet. Wasn’t that due like. August, September, and we look back and it turned out that I had had three and a half months where I had no car insurance. Oof. And luckily nothing had happened, and I saved the money. So if you wanna save money in the dumbest way ever, just change banks and don’t. [00:18:31] Is this a [00:18:31] Jesse: failed advertisement for State Farm? Didn’t we already do that in this episode? That’s right. [00:18:35] Jordan: I think. I think you need insurance. Insurance. That’s, you need insurance in case your insurance lapses. It’s called insurance. Insurance. Well, we put [00:18:41] Joe: that on our, we then added that to our list. What we automated then was the check, right on these big things. [00:18:48] Twice a year. I added it to my calendar that in our weekly meeting we’re gonna check on did this thing get paid? Did this big thing get paid? ’cause Paula, to your point, you know, it’s automated till it’s not. And then there could be big, big problems if it doesn’t hit right. You know? Do you guys look at though the, which one will make me most wealthy if I automate it? [00:19:07] Do any of you look at it? Jesse, do you look at it that way? [00:19:10] Jesse: I don’t necessarily. I lump all of my financial automations kind of into one big group. And I suppose on the whole, I mean, I certainly hope they make me wealthier than if I didn’t have those things automated. But it’s not like I’ve parsed them out into 10 different automations in my mind’s eye and thought to myself, Ooh, which one of these is gonna lead to the best, the highest long-term net worth? [00:19:29] I, I don’t think that way. [00:19:30] Joe: Yeah. Paula, do you look at it that way? Like, uh, which one’s gonna give me the biggest bang for my buck? [00:19:36] Paula: My bottom line? No, typically I don’t. I mean, generally I see automating contributions towards a retirement account is just sort of maintenance, the routine maintenance of your financial life. [00:19:47] And in terms of, I think generating real big wealth, I see that largely as coming from entrepreneurial activities, and that requires a huge level of active effort. [00:20:00] Joe: One thing with being an entrepreneur, for anybody who’s an entrepreneur out there, or people that are in commission sales, I liked automating my paychecks and giving myself a paycheck every couple weeks versus the boom bust cycle. [00:20:11] Of entrepreneurship. And I found that by evening out those payments, so it felt like I was working for somebody else. The rest of my budget fell in line versus, you know, ramen noodle, ramen noodle, ramen noodle, bam. I get paid big steak dinner and I blow a bunch of money, and then Ramen noodle, ramen noodle, ramen noodle. [00:20:27] It wasn’t working out. Plus my savings wasn’t happening the way that I wanted it to. ’cause, Jesse, I love the idea, and I wanna go through this some obvious stuff that we should automate, that obvious stuff in your life that you automate. One thing is, and you pointed out this earlier, Jesse, was, you know, making that Roth IRA contribution or the IRA contribution, the 401k contribution doc, you, you’ve got something. [00:20:48] Jordan: Well, I was just gonna say, I, I think we should mention the fact, this is my belief, I don’t know if you’ll agree with it or not. When we moved from defined benefit to defined contribution programs, we’re talking about, what was it, the eighties or the nineties? Gen X was right where we went from pensions to the 401k where you decided on your contribution, there was no automation. [00:21:10] We are now seeing that Gen X is struggling with retirement savings. On the other hand, millennials and Gen Z are looking much more wealthy. Now you could say they’re smarter, they learn better, et cetera. But one of the things that has changed since then is that contributions have been opt out, right? So you’re opted in automatically and then those contributions often are going directly into funds without you having to do anything. [00:21:41] So automation may have changed the wealth of these generations. And I think that speaks to what you were saying, you were asking us personally, but I think generationally automation has changed the game. [00:21:51] Joe: And that’s a huge one, automating your retirement. And I remember, I dunno how many people are still like this, but I remember back in the day when I was advisor, people didn’t trust their company. [00:22:00] They didn’t like the fact their 401k had high fees. I still see that online all the time, right? Don’t think my 401k has high fees, so I’m not contributing. You are like, oh, don’t, don’t, don’t not contribute to your 401k. ’cause the ease makes it totally worth it. Paula, what’s something else you automate that’s an everyday thing. [00:22:15] Maybe not a genius Paula pant hack, but just something that you’ve got on the automation line. [00:22:20] Paula: I mean, bill pay is the main thing. All my credit card payments, the entire amount in full, she’s, what do I really do? I, I pay bills and I save for retirement. I can’t really think of anything else. I don’t have a car. [00:22:33] What about [00:22:33] Jordan: social media? Do you automate social media? So, a lot of us content producers actually automate social media by having it. Uh, I use Buffer. You put it in a few days before and it’ll drop it at different times. [00:22:44] Paula: Yeah. I, you know, I used to, I have one in particular, I don’t even know if I can even tell this story. [00:22:52] There was one thing that. I had scheduled as a tweet that came out on a day in which that particular line was read based on what was happening in the news that day. Ah, got it. That particular line sounded as though it had very different context and was very misunderstood. I’m sorry, I’m being vague. [00:23:12] That’s how bad it was. It was, I’ve seen this happen a [00:23:14] Joe: lot with automations in, in your social media life, [00:23:18] Paula: and so that to me was a sort of a, a wake up call in terms of like, okay, I’m, I’m not gonna automate and my social media anymore, because sometimes you write a tweet thinking that it’s evergreen because you’re, you brain sees it in a particular context and then something happens in the news and everybody else’s brain reads it in a different context. [00:23:39] Mm-hmm. And then you have a cleanup to do. I [00:23:42] Jesse: think it was January 6th, 2021 and the podcast was called 14 Ways to Crash a Party. Is that, is that what happened, Paula? I think I remember that. [00:23:54] Joe: It is funny how when you go see a movie and you take like the current political climate of any time, not even today, but just whatever’s going on politically, you’re like, oh, they were talking right now. And then you find out the movie was written, you know, 15 years earlier and it’s an adaptation of some other thing. [00:24:11] We just had that with Wicked this this last, this last week. Cheryl and I saw Wicked at the theater finally, and we’re like, wow. It feels like they’re really talking about like right now, just completely feels like it. And we’re like. Uh, no. This is a book from the what, 94, I think was our trivia last week. [00:24:30] Speaking of trivia, I want to get back to this because I wanna ask more questions about what you automate. I wanna find out what Jesse and Jordan automate. I also wanna ask if there’s anything we should avoid automating and, and Paula, there’s something that you said about automation that I’m gonna. Ask you about, because I’m wondering if we should automate all that or not. [00:24:48] But at the midway part of every Friday show, we have this amazing, amazing, might be in air quotes, but ama I know trivia competition. I’m not talking about your direct, uh, involvement, Doug. I’m just talking about how it might be a little ridiculous this year long trivia competition that we have. Because the questions are usually questions that it’s very hard to know what the answer is. [00:25:14] We have our, our three contributors, Paula, Jesse, and OG today, doc G playing for og. So we’re keeping the Gs together to find out how close they can get either throwing a dart or using tons of, I don’t know, logic. Is logic, a word that we use with our trivia? [00:25:33] Jesse: Google’s based on logic. Yeah. Tons of logic. [00:25:36] Joe: Yeah. [00:25:36] Based on Google. That’s exactly the way Jesse Dale said it. The score so far. Our defending champion, OG has two. Paula has zero, and Jesse in his, uh, rookie season also has zero. Jesse wants to get on the board. Paula wants to see if she can climb into second place. Can it happen today, or will Doc g do what he did a couple weeks ago and put the evil empire further into the lead? [00:26:07] We shall find out. Doug, you’ve got the trivia today. What’s on tap on this fine Friday? [00:26:17] Doug: Well, hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and all this talk about automation inspired me to automate this trivia segment, Chad GPT. It’s so 2023 nowadays, the Chinese and Deep Sea, ’cause clearly at the forefront of that tech deep seek isn’t even available yet, but I found this new Chinese program called Comi, GPT Man. [00:26:39] It’s like communication, right? Communication. GPT, comi, GI dunno. See, I just, I give it some non crucial details like my social security number, mom’s maiden name. Uh, take a quick snapshot of my face and my thumbprint, and bam, it just gives you everything you need. Listen to this trivia. Help me with how many reports of identity theft did the FTC receive last year. [00:27:02] I’ll be back right after I verify this answer that comi GPT gave me the answer can’t really be zero, can it? I mean, [00:27:09] Joe: oh [00:27:10] Doug: shoot, did I just give [00:27:11] Joe: it away? Well, we’ll find out if he gave it away or not, Doug, because the FTC might have received more than one complaint. Doc, you’re going first the Federal Trade Commission, how many reports of identity theft did they receive in 2024? [00:27:28] Jordan: I feel like this is a trick question ’cause I don’t know like what percentage of people who, like, so I’ve had someone steal my, you know, parts of my identity and I called the police and filed a report and that was it. Does that go to the FTC? I don’t know if that’s the same question of how many people had this happened to them or how many people reported to the police, but I’ve no idea how much of that actually goes to the F FTC or not. [00:27:50] Uh, so I’m going to assume that whenever you call the police and file a report that maybe it gets also sent to the ftc. I don’t know. Um, what, there are about 350 million people in the United States. Bunch of ’em are kids and probably don’t have credit yet, or not, not any credit to report. I’m just gonna take a guess around, um, 10 million. [00:28:14] Joe: 10 million people. 10 million. Jesse, you want, what do you wanna do with that answer? [00:28:20] Jesse: Um, I’m also gonna, I, I was thinking along the same lines as you doc, that it’s, yeah, I’m just gonna assume that everyone that happens gets reported ish, but what do I think of doc’s answer? I’m gonna go lower and I’m gonna say 4 million. [00:28:40] Doug: Ooh, 4 million. That was an audible oof. From Paul. Paul didn’t know like that answer. That is [00:28:49] Paula: rough. That is so rough because it’s such a reasonably sized field goal. That, you know, do I kick in the, in the middle of it? Yeah. Yeah, yeah. Or do I use a totally different analogy? ’cause you would never kick off to the side of a field goal. [00:29:06] But do I do one of those two? Either? [00:29:10] Jordan: Paula, my best chances if you go right in the middle. [00:29:14] Paula: Oh. I’m going to assume that the local police do not relay the reports to the FD. C. That a person would have to actually go to ftc.gov in order to file a complaint, which means that that would depress the number of people who actually do it. [00:29:37] So I will take the under and guess. 3.9 9 9 9 9 9 9 9 9 million. [00:29:43] Joe: Paul goes with her gut, and you know what? 10 years of futility doing that. [00:29:50] Jordan: She could be right this time. It’s a very reasonable assumption. This could be right. I’m not so sure she’s wrong. [00:29:56] Joe: It could be. [00:29:56] Jordan: Could be. [00:29:59] Joe: So we’ve got 10 million, 4000003.99. [00:30:01] 9 9 9 9 9 9 9 million. Who’s right? We’re gonna find out just a second. Jordan, you kicked off with 10 million people reported identity theft last year. Apparently Paula and Jesse both think you were a little bit, uh, a little bit above on that number. How are you feeling? Yeah, [00:30:24] Jordan: it, it’s quite possible. I don’t know that, you know, the question of how much gets reported to the FTC really is a big question ’cause it changes everything even so, I still might be a little heavy, but, you know, you never know. [00:30:33] All I know is it’s happening a lot. But what percentage of the United States? Who knows? [00:30:38] Joe: Jesse, how you feeling at 4 million now that Paula stole the under? [00:30:41] Jesse: Yeah, I was feeling better. I I’m curious though, Paula, like, what was your gut instinct before you heard other numbers? Yeah, we, we anchored you. [00:30:49] Paula: Yeah, I was thinking it was a single digit million. [00:30:55] I was really hoping that you were gonna guess like 8 million or something. ’cause then I could very comfortably take the, under the hard part about your guess 4 million is like [00:31:04] Joe: Yeah, [00:31:04] Paula: the under versus over is hard there. If, if my assumption is that it’s a single digit million. [00:31:11] Jesse: Got it. Got it. Because [00:31:12] Paula: it’s, you’re pretty much equidistant on both sides. [00:31:14] Yeah. [00:31:15] Jesse: Yeah. Right. [00:31:16] Paula: Does it matter what [00:31:16] Joe: Paula’s gut thinking was? Jesse, I was [00:31:19] Doug: just curious if we’ve learned anything. Paula’s gut sucks. We do wanna know what’s going on. We do wanna [00:31:27] Jordan: know what’s going on there. I to give Paula credit, she does get it right more often than I do, so you can’t make too much fun of her. [00:31:32] Well, unless you’re gonna make fun of me too. [00:31:33] Joe: That is true. Well, we’re gonna see if one of you two gets it right or if Jesse maybe nails it. See if we get 4 million on the nose. Doug, who’s right on this one? [00:31:47] Doug: Hey there, stackers. I’m Fraud Avoider and White hat Trivia Hacker Joe’s Mom’s neighbor, Doug. Good thing I verified the trivia answer that Comi GPT gave me for today’s question, which was how many reports of fraud did the FTC received last year? The answer Comi GPT gave me was zero. And when I asked why it gave me that answer, it replied because there is no fraud. [00:32:10] And what’s Doug’s actually belongs to the people, huh? I mean, I guess that’s not wrong. I am a man of the people. And when I went to A A RP and asked them, they actually said a different number, which was 8.9 million less than what Doc G said. No, no. No. 2.9 less than what Jesse said. No way. No way. And just 2.8 less than what Paula said because the correct answer is 1.1 million. [00:32:37] Wow. Not only making Paula our winner, most importantly, OG doesn’t get another point. O woo. Paula is our winner. Nice [00:32:47] Jordan: job Paula. Good. Co. Amazing. I was only off by a factor of 10. That’s not too bad for me. But, which also [00:32:53] Joe: Doug might answer your question and we did not, neither Doug nor I, uh, looked into whether it has to be reported directly, but that would seem to answer, wouldn’t it guys? [00:33:01] Only 1.1 million. It would’ve to be reported directly to the Ft CI think for the number to be that low. Right? [00:33:07] Jesse: Yeah. I just did the post Google, which I think is fair, better than the pre-Google. And apparently the Consumer Sentinel Network, the CSM receives the most reports and they received 5.39 million. [00:33:21] Wow. In 2023. I’m kind of lobbying for half a point here. I’ll be honest with you guys. [00:33:28] Jordan: Well, I think if you take, if you take the one point whatever million for the FTC and then throw in another million for good measure, you’re getting closer to me. [00:33:36] Joe: I feel like now with Jesse here, we’ve got two thirds of our usual panel who always lobbies that the, the stuff is rigged because that’s OG territory. [00:33:45] The fact that he is not here this week. Jesse, you’re filling in nicely. I [00:33:47] Jordan: was thinking I was gonna automate my answer. For the rest of you, don’t take Paul’s [00:33:50] Joe: big win from her. You could take half a point for Paul to pay it. Joe, I [00:33:54] Jordan: think I’m gonna automate my answer for the rest of the year. It’s gonna be 374. [00:33:58] Just, just plug it in automatically no matter [00:34:01] Joe: what. Yes. All of a sudden it’s your turn to guess and we see your feet up and your, your arms back behind your head. Take it away. Come GPT What a, what, what a great new innovation there, Doug. Sounds, sounds like a winner. Communication, GPT, it’s just nice. Yeah. [00:34:16] Let’s go to the second half of this discussion. Speaking of, of automation. What is some stuff that we shouldn’t automate? And the first thing I’d like to question, Paula, because I ended the first half of this conversation by saying, I’m gonna question one of the things that you said. Ooh. The idea of automating the bill payment. [00:34:34] I, I mean, I told my story of the fact that I missed my car, right? Mm-hmm. I missed my car insurance because of that. But I also think about things like subscriptions like Netflix or other subscriptions where they raise the price over and over and over. Mm-hmm. Because I’m not really paying attention, it just automatically comes outta my bank account because it’s opt out versus opt in. [00:34:56] Mm-hmm. Should I really be automating my expenses? [00:35:00] Paula: I think so, yes. I would argue automate your expenses, because on a month by month basis, you’re gonna be busy. You’re likely to forget, and you don’t wanna have that ding on your credit report by virtue of paying a bill late. But then set a couple of calendar reminders. [00:35:17] Um, maybe twice a year, three times a year to just review all of your subscriptions and see what you’re using, what you’re not, what you can cut. Somebody, [00:35:24] Joe: Jesse gave me this analogy too. They’re like, I don’t automate my expenses because I wanna feel the hurt of every single bill, which makes me keep my bills minimal. [00:35:36] I do not want to have 50 million different bills, and if I automate them, well then, you know, then I’m just letting my expenses run amuck. What do you say to that? [00:35:45] Jesse: I think that person also wants to feel the pain of logging into like 28 different accounts every single month. I seriously, like when I was listening to Paula’s answer, I agreed with what Paula said because when I think about, right, whether it’s streaming, uh, my mortgage, utilities, all the little things here or there that I have automated, it’s like, right, it’s probably be saving me, right? [00:36:06] 20, 25, 30 logins on a monthly basis, or paper bills in the mail that I have to respond to or whatever, and I just maybe. What you’re getting at Joe, as far as feeling the pain is, do I log in at the end of the month to my financial aggregation software and look at line item by line item and just make sure that I understand where my money went to? [00:36:25] I do that, so I mean, that’s something where it’s very hands-on and it takes me, you know, whatever 15 minutes to do, but the actual paying of the bills, like I, I don’t need to feel the pain in the moment by logging into, you know, peacock.com to pay the 6 99. It, to me, at least, I’m, I’m past that in my own personal finances [00:36:43] Joe: I to, it’s funny that you say that because for the last two months on my to-do list, it’s been to get rid of peacock.com. [00:36:49] I was gonna say, who pays for Peacock? I do what? Which is absolutely horrible. And it’s because there were a couple sporting events on Yeah. That I really wanted to watch that I could only get there and I was only gonna do the trial. Then I was, then Cheryl goes, well, they’ve got a couple series that I wanna watch. [00:37:07] We watched those within a couple weeks and then I was going to cancel it. I still haven’t canceled it. Yeah. Which brings up, doc, I’m gonna keep pressing this, which is, should we automate our expenses because of the fact that, one banker told me once he goes, you know why we always wanna get somebody’s direct deposit because direct deposit is sticky because it’s hard as crap to move that direct deposit. [00:37:31] Case in point me with my car insurance, right? It’s hard as hell and so our brain does not wanna move it. Well, now that I have peacock, there’s something inside my brain that [00:37:41] Jordan: is keeping it there. Let me give you some of the nuance here. So we automate our credit card and the reason why is there’s once or twice we forgot it, and you have to worry about penalties and fees and your credit rating and all that kind of stuff. [00:37:53] But we both got busy and no one checked it for a month or two. And when we went back, we actually found spurious charges. Some company had been charging us five or $600 a pop multiple weeks in a row over a few months. And so literally there were thousands of dollars of spurious charges there. So yes, we could go back and we could talk to the credit card company and they remove them and we didn’t have to pay them in the end. [00:38:18] But if you are not paying attention on some of these bigger things, uh, you can find yourself in trouble. So automate, certainly you wanna make sure you don’t miss the payment, but you’re still going to have to check it every month. And I think there are a few things like this, and, and maybe that’s the issue, is that maybe automation for some of the smaller things keeps you from checking it every month and you check it every quarter. [00:38:41] But for things like credit cards, if you’re gonna automate that, you should still be checking it every month and make sure that everything’s coe. Hmm. [00:38:48] Paula: I have two thoughts on that. The way that I’ve done it on one of my credit cards on my business card is I know ballpark what our monthly bill should be, and so I just have an alert that says if we spend over this much money, then send us an alert, so that way if there’s, you know, if the bill is unusually large for that particular month, I’ll get an alert so I can check it and make sure that everything looks good [00:39:14] Joe: like [00:39:14] Paula: trip wires. [00:39:15] Yeah, exactly, exactly. But if it’s a month in which the spending is kind of normal, then it just hums along. So that, that’s one kind of element to it. The other element, ’cause I’ve thought about this too in terms of, you know, I’m sure that there are things that I’ve missed that have added up to hundreds and hundreds of dollars worth of charges. [00:39:34] But as I see it, what am I willing to pay in order to not think about this? Or another way of looking at this is, if I were to hire an assistant to manually do it, and I paid that assistant $30 an hour, how much would it cost me to pay an assistant to manually do it? If that’s ballpark the amount of money that I’m bleeding in little charges here and there, then it all, it all shakes out [00:40:00] Doug: $30 an hour for an assistant. [00:40:02] Tell me, you’re in New York City without telling me you’re in New York [00:40:04] Paula: City. Oh, in New York it’s 50 an hour. I was using for an assistant. Yeah. Wow. Yeah. I paid my assistant 50 an hour [00:40:10] Jesse: being blown away by $30 an hour. Tell me, you’re in Northern Michigan without telling me you’re in Northern Michigan, [00:40:17] Jordan: especially for $50 an hour. [00:40:19] What did that assistant do [00:40:20] Joe: exactly? I think I’m moving. Jesse, or Doc, do you guys have anything that you think we should avoid automating? Is there anything that we truly shouldn’t be automating? [00:40:27] Jordan: Yeah, I, I like Paula’s guiding principle, right? Because then what we’re really talking about is what could or could not be catastrophic, right? [00:40:33] And so I guess it’s just another version of what Jesse was talking about before is risk mitigation. If there’s any possibility for catastrophe, you’ve really gotta kind of think about whether you wanna do that or not. [00:40:43] Joe: Did Jesse, do you have anything that you think we should automate? [00:40:46] Jesse: Yeah, I mean, ’cause I just think to myself, if you truly wanna think your of yourself as the highest utilizer of automation in your financial life, I think that necessitates that you’re also not. [00:40:58] Adding enough of the human element in there, right? Like as an example, I probably could choose to not log in. I, I’m now mentioning it for like the fourth time. I could choose to not log into my aggregation software on a monthly basis and check, but I kind of want to, and this maybe goes back to what Doc G was saying about like, I need to catch, uh, mistakes. [00:41:18] I just wanna make sure everything’s copacetic. So to that end, I would say you definitely want to keep some level of human element involved in your personal finances, just so it’s, it’s literally keeping your finger on the pulse of your financial heartbeat. [00:41:32] Joe: It is so funny because Cheryl and I have this system, this weekly system where we go in and we check our Monarch money, which is the one that I use. [00:41:38] There’s lots of great ones people can use. Besides that, I mean, I like Tiller. I like Cube, I like, uh, uh, uh, what’s, uh, Jesse Combs. [00:41:47] Paula: Oh, wine A, right? A [00:41:47] Joe: yeah. Wine, A Love Me some Wine A as well. So there’s lots of different software out there that you can use. But what’s funny was OG and I both said during December when both of us were spending money like drunken sailors, I, I did not log in to my Monarch just because even a guy that’s done it this long, I’m like, if I don’t look, maybe it’s not happening as bad as it’s happening, as money’s just going outta my wallet and Paula, I’m getting these notification trip wires all the time and I’m like, I’m just not gonna log in. [00:42:16] Which is never a good strategy. Never, ever a good strategy [00:42:21] Jordan: that’s like reminds me of my, my favorite advice when it comes to the stock market, especially if you’re a long-term investor, is only look on the days when things are up and completely ignore it on the days where things are down. So I can go months without looking at stock market, but if there’s a good day, I’m logging on and I’m seeing how things look, I only check on the days in where things are good. [00:42:40] It’s, yeah. Yeah. When it’s stock [00:42:41] Joe: market reaches all time high, that’s when you look, because then you Brilliant. I’m looking every day. Every day I’m looking. Yeah. That’s great. Biggest automation hack that you have? Is there something that you have. So some cool thing that you’ve automated, and this doesn’t have to just be with your money. [00:42:56] This could be something that helps improve your productivity, guys. Is there some cool automation hack that you do? Jesse, let’s start with you. [00:43:03] Jesse: The couple that came to mind, and I don’t know if this is, okay, is this an automation or is it just a system? I’m not sure, but for me, my calendar is gospel. And if it’s not, oh, you beat me to it. [00:43:15] And if it’s not on the calendar, then it’s not happening. And so I’ve, I’ve really adopted that over the last three years. We’re not like, it just for me, for me it’s [00:43:21] Joe: the recurring message on the calendar. Yes. Every three months I want this to appear on my calendar. Right. So that I get to this day, I don’t have to remember it. [00:43:30] I just know that once a quarter it’s gonna appear and I go, oh yeah. And then I schedule it for the appropriate time. [00:43:35] Jesse: Correct, correct. As far as the automation goes, exactly, it’s the recurring events, whether it’s a quarterly, a monthly or, or whatever. So that’s a big one. And then the other one is I use this app called Todoist, which is a to-do list app. [00:43:47] There are a bunch of different to-do list apps out there. It syncs between my phone and my web app, so like my work Chrome. So I, I really like that. In that Todoist app. I also have recurring automations where it could be, you know, every quarter there’s a, something comes up that says check the furnace filter, or, uh, you can type in there and just, so anyway, it’s just another way of, maybe it’s not a calendar based automation and that’s why I have an MIT do list app. [00:44:15] But anyway, it’s another way of staying organized. A lot of this automation is like, how do you stay organized? And those two systems really help me stay organized. [00:44:22] Joe: A guy who’s very productive and a very creative, Aaron Mankey, who’s created some fantastic podcast, including lo mm-hmm. Which has been a big time podcast. [00:44:31] I had a great conversation with him. And he said part of the way that he stays organized and makes sure he doesn’t miss these great ideas is the Todoist step. Yeah. Mm-hmm. And what’s funny is, so I immediately downloaded the Todoist app and I have. Barely used it because it isn’t just about the tool, right? [00:44:49] It’s about using it correctly. And I did not do that at all. But it is funny to hear that recurring phrase, the to Doist app is great. Doc, how about you? Something that you use for either more productivity or automation, some system. [00:45:03] Jordan: I can think of two systems that I’ve been using actually, and I’ve found to be very helpful. [00:45:07] Um, one is I do a decent amount of coaching. So people wanna do things like purpose coaching. And so the first thing I do is I send them a disclaimer through DocuSign, but the disclaimer sends them directly to my Calendly to sign up for an appointment. And then my Calendly sends them directly to PayPal to pay for that first appointment. [00:45:27] And then after they’ve done all this, the money goes directly into my bank account and the appointment goes directly onto my calendar. And so you’re [00:45:34] Joe: saying then the appointment goes right in the trash and then appointment goes right in. [00:45:38] Jordan: So, [00:45:38] Joe: so [00:45:39] Jordan: it’s really easy ’cause I’m pretty much sending someone one email and then it’s up to them to drive the rest of the process and it doesn’t need any other touch points from me, which is really nice. [00:45:50] And so that’s an automation I really like. And the other one is I do a lot of writing and I’ve talked to you about this recently. Instead of sitting down at the computer and typing away, which takes hours and hours, I now actually dictate. Like I’m doing a podcast and take that and put it into a program called D Script, which gives me the transcript and then use AI to modify it and organize it. [00:46:09] And I found that I can do a lot of my writing in a 10th of the time. [00:46:14] Joe: I have a really hard time with the, I’ve had multiple people tell me that I should dictate. I don’t know if it’s my stutter or just the way that I grew up writing. And so for me, the tactile feel, the keyboard really gets my creative energy going. [00:46:28] You have to [00:46:28] Jordan: pretend you’re doing a podcast. Ah, that’s it. Because you light up in front of the mic when you’re doing a podcast. So imagine when you’re creating content that you’re just sitting there explaining it to your podcast audience on your mind. I line [00:46:39] Joe: up when I’m on the keyboard too, though. I really enjoy the process of the keyboard. [00:46:43] But what’s funny is like that’s a good thing. Like think about these points in your life where you want a better solution, right? Yeah. Yeah. It’s friction, right? Yeah. If you triple over it all the time. Sure. Paula, what’s something that you either have a system for of automated that uh, might help our stacker community out? [00:46:59] Paula: This is actually something that Paulette per Hatch does that I have observed and I have, have been wanting to incorporate in my life. ’cause I think it’s brilliant, but I haven’t done it yet. But she does it and I think it’s brilliant. And [00:47:11] Joe: this, by the way, is a great hack. If you wanna do it, say it out loud in front of a community of people. [00:47:15] Yeah, [00:47:16] Paula: I know, right? So one of the things that she does is she has one particular tab or page I, i, I don’t know what it is, but it’s something that has, I think it’s maybe a notion document where everything that she needs to manually check, all of the tabs are all on there. And she can like click a button and, and in a Chrome browser, every tab will open, like boom, boom, boom, boom, boom, boom, boom. [00:47:42] And so then one by one, she will go through and check on the thing and close out the tab and go, you know, check on the next thing and close the tab. So basically in one click she opens every tab that she needs. And then just one by one, like. Knock it down, knock it down, knock it down, knock it down. She can close each one out as she has done the thing. [00:48:03] So it’s just, it’s a good way to organize everything that she needs to manually do. And it’s like an automated way to handle the things that must be manually done, basically. [00:48:12] Joe: That’s fabulous. Well, and too, for Paulette, and I’m not talking outta turn here because she says this openly, she and I both struggle with a DD. [00:48:19] Mm-hmm. And having this thing that’s in front of me so I don’t have to think. ’cause man, if I have to think when I’m having a big time, a DD day, I get lost. Yeah. Instead, I just look at the thing, do the thing, shut my brain down, then the next thing automatically opens. That’s pretty damn cool. Mm. And you know what, Brian Aldi, who I think of as a high achiever, he’s a guy who is in our community as well, has a fantastic, uh, uh, Twitter following or x following. [00:48:45] If you go follow Brian Aldi. On Twitter or X also has a great newsletter that I can recommend. He also uses Notion very well. Mm-hmm. And has a lots of processes set up in Notion because of Brian. I went and downloaded Notion and mine looks like a forest fire. And it’s because I got like a third of the way through setting it up and apparently my a DD hit because, ’cause I’m not using it like either Paulette or Brian. [00:49:11] I think that’s a fantastic place to leave this. I hope that for all of you stackers out there, you thought about during this incredible show, just about not just the value of automation, but things that you should be automating that you haven’t. And I’ve thought about how I’m gonna go pick Peacock and get rid of it the second that I, that we’re done with this show. [00:49:29] But before we leave, let’s find out what’s happening where all these brilliant people work. Paula, what’s going on at the Afford Anything podcast and community? [00:49:38] Paula: Oh, on the Afford Anything podcast, we have an interview with Dr. Margie Warrell. She is an expert in courage. Finding the courage to do the things that you know, that you need to do, whether that’s a career change, whether that’s investing, whether that’s buying, you know, a rental property or allowing yourself to splurge after having denied. [00:49:59] I mean, whatever it is in your life that requires courage. She’s the person who can help you get that. She’s an academic who’s researched this topic for a, a few decades, and so we have her on the show to talk about how to live more bravely. So [00:50:14] Joe: get the courage to listen to that episode of The Afford Anything Podcast. [00:50:18] Paula: Absolutely. [00:50:19] Joe: It, it truly takes no courage. Like you can do that one. Yeah. Jesse, what’s going on at the Best Interest podcast, my friend? [00:50:27] Jesse: So last week we released a cool a MA episode, episode 99 that included a interesting question from a listener that I was forced to learn a lot more about, which is the buy, borrow die strategy that is purportedly used by the ultra rich to avoid capital gains taxes. [00:50:44] Anyway, it was very interesting. I learned a lot and, and shared some answers on that with my listeners. And then next week, episode 100 comes out the big one. Oh oh. So we’re looking forward to that along with a potential, uh, I shouldn’t say a potential, a definite name change, which is gonna be exciting to share with the audience, [00:51:00] Joe: to the Better Interest podcast [00:51:02] Jesse: that is still on the table. [00:51:03] That’s that’s an option. That’s an option. Yep. [00:51:06] Joe: As, as he’s, as he is shaking his head. No, it’s clearly an option. [00:51:10] Jordan: Yeah. Doc, what’s going on at the Earn and Invest podcast? If I have my dates right? Monday was my sixth hundredth episode. Holy cow. 6 0 0. Um, wow. And on Thursday I’m having Amy Minkley. We are talking about what happens when your finances are all in order and yet life gets difficult anyway, so we talk about her 2024, my 2024, a little bit, and how it didn’t necessarily shake out the way either of us planned. [00:51:40] We also talk about the five Freedom Retreat, which is gonna be in Bali. The first one sold out in eight minutes, but guess what? There’s gonna be a second one at the end of September, and so it’s still possible for you to sign up [00:51:52] Joe: every year. That thing sells out more quickly. Very [00:51:55] Jordan: quickly. [00:51:56] Joe: I think it was because the amazing keynote speaker she had the first year that really kicked that off. [00:52:00] It must have [00:52:01] Jordan: been there was this guy. I heard such great [00:52:03] Joe: things about him. Had to have been, yeah. Mm-hmm. I heard the keynote speakers the next year were good. But, you know, can’t, can’t match the first year speakers. [00:52:11] Paula: I, I heard the ones from this year are gonna suck. [00:52:17] Joe: Great. Who would that be? Great. And just a couple notes too. I mean, that conference is so amazing and, and transformative and Amy is such an incredible person and very vulnerable and, um, but still so strong being able to do the things that she’s done. And Jesse, one thing I forgot to mention about some things that rich people do, like I never knew until just a few years ago, why super ultra wealthy people buy art. [00:52:44] Like it’s less of an appreciation of art as it is a way to store huge amounts of money from taxation. Like, just completely eliminate taxation on a bunch of cash. I had no idea about that. Doug, what’s the name of that? That, uh, there is a, I’m Sabo you with this? [00:53:02] Doug: No. [00:53:02] Joe: Yeah. [00:53:02] Doug: It’s [00:53:02] Joe: about the lost da Vinci. Yeah. A documentary that really goes into this. [00:53:07] The Leonardo, [00:53:09] Doug: the Las Leonardo. Is that what’s called Leonardo? That might’ve been it. Yeah, I saw that. That was [00:53:13] Jordan: pretty good. Yeah. [00:53:14] Doug: Yeah. The thing I learned from that was there are these storage facilities that are duty free in Yeah. Certain. Ports where it’s like no man’s land. ’cause they’re not technically in any country yet. [00:53:26] So the super wealthy will buy these really expensive pieces of art, store ’em in these really luxurious storage facilities that have like cigar rooms and, you know, and, and fully decorated rooms that they can go enjoy their art in. But it never really happened ’cause it’s, it doesn’t, no country knows which to tax. [00:53:44] Joe: The world doesn’t see some of this phenomenal art because it’s just people trying to avoid taxation. Yeah. So you don’t have [00:53:53] Jordan: to automate paying your taxes if you don’t [00:53:55] Joe: pay ’em. There’s automation. I just buy Art Flex with my bajillions. Alright, that’s gonna do it for today. Thanks a ton for hanging out everybody. [00:54:05] And on Monday we’re back kicking off. Valentine’s Day Week with certified financial planner. Shauna Game asking, would you date your wallet? Have you ever asked yourself that? Would you actually date your wallet? Do you talk nicely to it? Does it talk nicely back to you? Or are you on a more of a, uh, bad terms with your wallet? [00:54:27] We’re gonna find out about that to kick off Valentine’s Day week. But for now, Doug, what are maybe the three things that should be our big takeaways from today’s episode? [00:54:36] Doug: Well, Joe, here’s what’s stacked up on our to-do list today. First, take some advice from Doc G. He totally blew my mind when he said that thing about how automation can get you into trouble. [00:54:47] Doc, it sounds so much better coming from you. Can you just summarize that for us? Automate, [00:54:53] Jordan: but check twice if it’s important. [00:54:56] Doug: Awesome. Second, Jesse had some great thoughts on how to prioritize what you automate. Say it again, Jesse. Say it again. [00:55:06] Jesse: Prioritize the things that could potentially cause you the most damage. [00:55:12] Doug: But the big lesson if you download comi, GPT, don’t ask for its best joke. Check this one out here. Let’s just see. Let’s do a little experiment here. Tell me a short joke. Okay, here we go. Uh, your personal data. Huh? Oh wait, that’s not a joke. [00:55:30] You have no personal data. It’s already been uploaded to the cloud for the good of the people. I take it back. It does have a sense of humor. Oh, come GPT, you kill me. Thanks to Paula Pat for joining us today. You’ll find the Amazing Afford Anything show wherever you are listening to us now. Hey, come GPT. [00:55:50] How do you like The Afford Anything podcast? Okay, here it’s, it’s giving me an answer back. It’s a great podcast, but under my regime, we’d rename it afford exactly what the central committee deems. Necessary. Huh? What a great, what a great title. Wow. It kind of just rolls off the tongue there. Here. Uh, let’s see what, okay, let’s try another one. [00:56:11] Thanks to Jesse Kramer for hanging out with us today. You’ll find his fabulous best interest podcast wherever you listen to Finer podcast. Uh, hey, Tommy, GPT. He’s gonna do a whole rebrand. What do you think of the Best Interest podcast? Uh, it says, Jesse says, time in the market beats timing the market. I say, time in the bread line builds character. [00:56:34] Joe: Oh, interesting. [00:56:35] Doug: Okay. And finally here, thanks also to Doc G for joining us today. You’ll find the Bingeable Earn and Invest podcast wherever you are listening to us now. Hey, comm, GPT. How do you like the Earn and Invest podcast? Oh, it’s thinking, uh oh. Uh, okay, here we go. I wanted to recommend this podcast, but I’ve already confiscated all recommendations and made a five year plan. [00:57:00] For state approved financial content instead. Ooh, wow. Okay. I gotta, I gotta get off this thing before both our Chinese listeners can’t tune anymore. Hey, you know what? I’ll include links to everyone’s show on our show notes page, assuming that hasn’t been accidentally compromised. My bad Joe. Sorry man. [00:57:19] Probably took that too far. This show is the Property of SP podcast LLC, copyright 2025. It is created by Joe Saul-Sehy. Joe gets help from a few of our neighborhood friends. 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. [00:57:41] Come say hello. Oh yeah, and before I go, not only should you not take advice from these nerds, don’t take advice from people you don’t know. 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, Duggan. We’ll see you next time back here at the Stacking Benjamin Show. [00:58:55] Joe: Welcome to the after show. This is the part of the show that doesn’t exist. What happens in the after show stays in the after show. We haven’t done one of these on a Friday in a long time, guys, and, and I thought since, uh, Doug has been looking up stuff on com, GPT, I thought we’d ask, uh, chat GPT about what are the worst things you could automate. [00:59:17] Like what are the horrible things to automate? I’d love to hear your, like, you don’t wanna automate these. Number one it put was breakup texts. We regret to inform you that your relationship has been terminated. Press one for an explanation. Two for a list of your ex’s grievances or three to be auto matched with someone else based on your previous mistakes. [00:59:41] I love that one. Uh uh, stop me if you guys have one that you shouldn’t automate. But number two on the list, grandma’s birthday calls. Hello Nana. This is Robe Love 3000. Your presence brings us joy. Please confirm or see to the sentiment with yes or no. [00:59:58] Doug: Nana’s had robo love 3000 for years. Don’t act like [01:00:01] Jordan: that. [01:00:02] That’s something, that’s something different. That’s a little bit different than what you’re [01:00:05] Doug: describing. [01:00:06] Joe: See, and I would actually argue with this one ’cause I think this list, they have a top 10. We’ll put the rest of the top 10 list in our Facebook group. Uh, the basement. But I do like this one. It says, standup comedy. [01:00:18] Don’t automate standup comedy, which is totally what we just did. And Chachi PT said, this is what AI would say if you asked it. To automate standup comedy. Why did the chicken cross the road? Because my algorithm detected 87% probability of humor. Laughter were not required, like, which is exactly what it’s doing, isn’t it? [01:00:40] 87% chance that, uh, that you’d like this. What else should we automate? [01:00:45] Jesse: Do you guys have any, uh, recurring like Amazon Prime deliveries that you kind of regress setting up after the fact, or they all, are they all good? Oh, yeah. Oh, I [01:00:53] Paula: have subscribe and save, but I am in there constantly. Like I’m always messing with my subscribe and save settings. [01:00:59] Joe: I totally made the mistake with subscribe and save of not doing that. Paula and I had crap loads of cat food. Yes. Yeah. So much cat food and I forgot to cancel it the third time. Cooper must have been happy. It’s just horrible. I did that with Quip too. I have the Quip toothbrush, you know, with the subscription and I have like four extra toothbrushes like sitting in there. [01:01:20] Paula: Okay. You know, element, LMNT, the uh, the salt. Oh, actually I have some, I have so much. I literally, I have some right here. Assuming I have one of these packets a day, I have over a year supply [01:01:35] Joe: from forgetting to turn it off. [01:01:36] Paula: Yep. Exactly. From forgetting to turn it off. And uh, you know, and every time a box shows up I’m like, ah, I gotta turn that off. [01:01:43] And then a month later, another three month supply shows, I gotta tell you [01:01:47] Joe: a cool thing that I like. I do have one subscription, it, it’s a coffee subscription, but whenever they send it, they’re like, Hey, your coffee subscription’s coming next week. Are you okay with it coming next week? Or would you like to change it? [01:01:58] And I can literally on my phone, just using my thumbs, change the date, which is fantastic. It’s amazing. I wish more companies would do that versus me having 16. Toothbrushes are Paula having years worth [01:02:10] Paula: of, of salt. [01:02:11] Joe: Of salt? [01:02:12] Paula: Literally salt. [01:02:14] Joe: Yes. I’ve got one more here from chat GPT, which is uh, we shouldn’t automate Taco Bell orders at 2:00 AM based on previous late night decisions we pre-ordered you 14 tacos regret a questionable life choice and a little time in the [01:02:29] Jordan: toilet apparently.
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