Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter.
Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday.
💰 In this episode:
- Why motivation fizzles out—and how to make it last
- The seven keys to Dynamic Drive (and how to apply them to your finances)
- How milestones and energy management keep you on track
- Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins?
- What cowboy fencing teaches us about peak performance (yes, that’s a thing)
Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun?
👉 Listen in now and get fired up—without burning out!
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
Our TikTok Minute
Doug’s Trivia
- Which baseball player did sports agent Scott Boras help sign the biggest contract of all time…$765M?
Have a question for the show?
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Other Mentions
- Flow: The Psychology of Optimal Experience (Harper Perennial Modern Classics)
- Mindset: The New Psychology of Success
- The Brand You 50: Fifty Ways to Transform Yourself from an ‘Employee’ into a Brand That Shouts Distinction, Commitment, and Passion!
Join Us Wednesday
Tune in on Wednesday when we’re joined by sports agent, “The Female Jerry Maguire,” Molly Fletcher. We dive into how to keep your engine running even when you feel like quitting.
Written by: Kevin Bailey
Miss our last show? Listen here: Yeah, We Overpaid For That (SB1656)
Episode transcript
[00:00:00] Joe: It’s Monday, and that means two things. Coffee and the Stacking. Benjamin Show you guys, you’re here at the mic nearly on time. Doug. Close but not quite. Yeah, it’s on me. Uhhuh, it’s, it’s a hundred percent. Okay. Oh gee. How long were we waiting for Doug? [00:00:18] OG: Nine minutes. Probably. [00:00:20] Joe: Yeah. My God. At [00:00:21] OG: least all I know is that when I sat down to turn on my computer, it was 8 28. [00:00:27] I was like, oh, [00:00:28] Joe: I’m on time. That’s all we need to know. But the second half of that then is coffee. So we’re here. We got coffee here. Doug, you got coffee? I have coffee today on the mission as far as you know, og Mic, Michigan Mission, um, getting ready for the NCAA tournament this week. Yes, we’ll see U of M, Purdue and Michigan State in the tournament. [00:00:52] It’s gonna be [00:00:52] OG: maybe in the final four. That would be something, [00:00:54] Joe: probably three of the final four, I’m sure. Let’s bet on it. [00:00:57] OG: Deal. [00:00:57] Joe: Who [00:00:58] Doug: does [00:00:58] Joe: that? I’m in. Alright. On behalf of the men and women at Navy Federal Credit Union, check that out. I’m my mug and the men and women making podcasts in mom’s basement. [00:01:10] Here’s to our troops, people keeping us safe while we celebrate college basketball, spring, and showing up to work. Doug, [00:01:20] Doug: here’s my takeaway from all of this. Now you’re flashing the fact that you have an amazing Navy federal credit union insulated mug with a nice travel lid on it. OG did it a few weeks ago. [00:01:35] Still sitting here with this old tech ceramic mug. I get it. It’s wonderful. [00:01:42] Joe: I get it. Here’s store troops. Let’s go stack some Benjamins together. Thanks folks. Rah. [00:01:47] bit: I guess you should have called. I did call earlier when using the phone. Earlier. When was that? Or later when Then I, uh, left a message. A message. [00:01:59] What number did you call? 2 4 9 5 6 7 8. I [00:02:06] can’t hear you. You’re trailing off. And did I catch a niner in there [00:02:09] where you’re calling from [00:02:10] a walkie-talkie? [00:02:11] No, it was cordless. Mm-hmm. [00:02:12] You know what? Don’t, not here, not now. [00:02:20] Doug: Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. [00:02:34] I’m Joe’s mom’s neighbor, Doug. And between the weather, time change, politics, wherever you look and. Deciding what to make for dinner. Like every night for the rest of your life, you’re probably feeling a little drained. Let’s help you create a machine to earn more, save better, and invest for the win. It’s all about seven steps to creating dynamic sustainable drive and we’ll dive in. [00:03:00] Plus we’ll share not one but two TikTok minutes and help stacker Alex learn how to pay less tax on selling his funds in his brokerage account. What’s the best way we’ll tackle it? And like that dream you never wanna wake up from, of course. Oh, I wanted to wake up from last night’s. I’ll share my amazing trivia. [00:03:21] And now here come two guys who think compound interest is magic. But still wish it worked faster, Joe and oh, [00:03:35] Joe: hey there, stackers. Welcome back to another week of Stacking Benjamins. Goodness. I’m Joe Salhi, average Joe money and across the cart table from me as he reports for duty on a Monday morning. It’s Mr. Og. How are you man? [00:03:52] OG: God. [00:03:53] TikTok: Fantastic. [00:03:54] Joe: He always forgets. It’s a audio podcast. Doug Camera. It’s not camera, audio [00:03:57] OG: podcast. [00:03:58] We put this on YouTube. [00:04:00] Joe: Well, we, [00:04:00] Doug: we put snippets on YouTube. He’s also trusting the great editing. We have to cut out all of the gaps because he’s like Bill Clinton. You ask him a question and then there’s this long thoughtful, and then you get, oh, I’m fine. [00:04:13] Joe: Mm, good. We’re talking about Dynamic drive today, guys. [00:04:17] Why do some people, I. Succeed where other people fail. [00:04:22] OG: Are you, are you guys watching nepotism? Oh, [00:04:24] Joe: nepotism, right? Have you watched the documentary Full Swing? All of them. Eh, isn’t it called Full Swing About Golf? Yeah. Watch some of it. There’s a golfer on there and stick with me, uh, stackers that aren’t interested in golf. [00:04:36] There is a guy on there named Joel Domon. And Joel Domon is a professional golfer and in the first season of Full Swing, he is profiled. He’s a super nice guy. He’s got this wonderful backstory that if you, if you watch it is heartwarming. He does some amazing things and he becomes a celebrity. And in season number two, he absolutely sucks. [00:04:59] And the question is, you know, there’s such thing as contentment, but if you’re driven to do better, why is it that some people can show up at work and be okay and you have other people that are just absolute rock stars? We’re gonna talk about the difference between success and not failure, but maybe complacency on today’s show. [00:05:24] So og, time to time to dig in and help our stackers earn a little bit more money. Today, I [00:05:30] OG: brought my shovel [00:05:31] Joe: well, and I don’t wanna stop there either. I think this is important in your financial plan. I think your financial plan can help you get some of this drive stuff that we’re gonna talk about. And the woman who created that term dynamic drive, Molly Fletcher, she’s here on Wednesday, so we’re gonna do a deep dive on how to get the drive today on Wednesday. [00:05:49] We’ll talk to the woman behind it, sports agent Molly Fletcher. But first, before we dive in, we got a couple sponsors who make it so we can keep on keeping on and you don’t have to pay a dime for all of this. Goodness. We’re gonna hear from them. And then we’re diving into Dynamic drive [00:06:12] on Wednesday. We’re gonna talk to Molly Fletcher for only about 25 or 30 minutes. I think this topic is so important, like this inner drive, like how do we succeed? Oh gee, you work with a lot of different clients. You see some people who, their financial plan, I’m sure is like clockwork. When I was a financial planner, I saw that other people where it always seemed like there was something that was derailing the plan, right? [00:06:34] All the time. And obviously. Some of those come outta the blue. Right? But I do have to tell you, there were some frequent offenders where, where it had less to do with what was going on around them, as it did with them. They would constantly find ways to self-sabotage. And that’s the, it’s the worst thing to have front row seats do. [00:06:54] Watching somebody self-sabotage their own success. [00:06:58] OG: Well, it ends up, it’s like a slow motion train wreck, especially when some of those things are self-inflicted. And obviously some of the biggest culprits are things like just living beyond your means for an extended period of time. And don’t get me wrong, there’s plenty of, you know, there’s a lot of stuff going on right now. [00:07:11] Government workers in particular are impacted by this, but there’s gonna be lots of secondary effects of trade policies and that sort of thing. And not talking political, but. There’s some stuff to roll downhill, right? And so there’s periods of time where you go, oh my gosh, we had a job change and you know, bills are still due and that’s gonna cause us to be a little, a little tipsy turvy for a little while. [00:07:32] And, uh, and that’s just life. It happens. But when you do it on a self-inflicted manner, you know, you’re like two, two people that are working full time and have for a long time and you go making good money, whatever that means to you. And somehow manage to spend $5 too much every single month, you know, every single month. [00:07:51] It’s like, well, as soon as I get the next pay raise, their next year’s bonus that’s going to be used to pay this off, or something like that. And, and of course, you and I know, and maybe most stackers know that that’s a recipe for disaster. It is interesting to see some things like that, and it really takes a different mindset shift to restart everything. [00:08:12] How many times, Joe, have you talked to people and you say, Hey, we gotta figure this out. And they go, well yeah, but the, this thing is sacred or this thing, you know, my kids have to go to private school. It’s like, well no, they don’t have to. You’re choosing to And I get why you’re choosing to I. Yeah. Which is perfectly fine. [00:08:26] I support why you’re making the decision. However, the limiting belief of I have to do this takes your ability to make that change or your ability to make a choice completely off the table. You say, I choose, I’m choosing to, and then you fill it in, makes it a little bit more in control. [00:08:42] Joe: The thing that frustrates me, and, and by the way, I lived exactly the life and you know this og I lived the life that you’re talking about for quite a while. [00:08:49] Yeah. Like the big lie. Me too. If I just make a little more money just a smash, things are gonna get better smidge money. And until I learned how to put at least a little bit of a lock on my spending and, and track my spending and have a budget, I can make more and more and more money. And I always found a way, you [00:09:03] OG: know what’s really, hold on just to talk about that for a quick second. [00:09:07] Every year let’s say that that’s you. I don’t know what broke the habit for you or broke the, what the breakthrough was for you on this, but for me it was looking at the last period of time, 5, 8, 10 years and going, hold on a second, how much has gone through my fingers in 10 years? Like, wait, wait, wait a second, man, this is so much money and I understand that I’ve got a mortgage and I’ve got kids that still, you know, you start looking at it from a big picture standpoint and you go, you know, if you’re a family that’s making 200,000 a year for 10 years, you had $2 million. [00:09:49] That went through for once. Once we got kind of a sense of that, and then thought about this moving forward and saying, okay, if the next 10 years are like the last 10 years and we also have 200,000 a year, that’s another 2 million. Like what do I want to make sure that this 2 million is different than the last 2 million? [00:10:07] And for me that was a big change kind of. Broadening that scope quite a bit and saying, let’s look backwards and try to get a better sense of what this is. ’cause day to day, month to month, hell, even year to year sometimes it’s like, I’m just, I’m just surviving here. You know what I mean? [00:10:22] Joe: Yeah. And there’s so much to unpack there. [00:10:24] I mean, don’t get me wrong. At the bottom level, I think people are motivated just to figure out how to eat tomorrow. But when you get past that kind of further up on Maslow’s hierarchy of needs, it becomes this, yeah, the job kind of sucks. My spending kind of sucks. I’m not doing things the way I should, but I’m okay. [00:10:41] I’m gonna be okay. And it’s a little bit of lack of respect for your own time and for your own wellbeing. [00:10:47] OG: Yeah. Maybe you’ll, [00:10:47] Joe: and uh, I got to the point where I realized if I wanted to go anywhere, I had to have a little bit more self-respect. It, it was damn hard to make that money. Mm-hmm. And the fact that I’m handing it to credit card companies Yeah. [00:11:01] Is a huge mistake. You know, and I even wanna take this to the career because what, what I’ve seen over my career, and I know you guys have too. Some people, they get that big job, they get the big promotion, or they get on the quote, big stage, right? Whatever it is. Here we are at the beginning of March Madness, and even if you’re not a basketball fan, I think you’ll understand this. [00:11:20] There are some teams that are gonna show up at March Madness and OG. They’re just happy to be there. They’re like, Hey, I’m happy to be there. They proceed to get their as kicked and they go home. And there’s other teams year after year after year. And I know all things aren’t created equal and some programs have more money. [00:11:35] I get all that. But there also is this difference between just showing up and high fiving myself and going, you know what? Now I’m on the platform, now I’m gonna do something with that platform. Now that I’m here, I’m gonna make something happen. I started studying this back in the nineties. I was really interested in a football coach, uh, Jimmy Johnson, who is never heard of him. [00:11:58] A Hall of Fame? Yeah. He’s a Hall of fame football coach for people who aren’t football fans. And I really started studying him ’cause no matter who, who he was. Oh, right. Well, no matter where he was og, he would win. [00:12:10] OG: Mm. [00:12:10] Joe: He’s at this program, this program, this, he wins no matter where he goes. [00:12:14] OG: All he does is win, win, win, no matter what. [00:12:17] Just lots of winning. He’s got money on his mind. [00:12:20] Joe: Just lots of winning going on. So as I was digging into Jimmy Johnson, I also dug into, by the way, Oprah Winfrey later in a winter. Um, all kinds of, of top CEOs and top performers. But studying Johnson back then in the early nineties, all he could talk about behind his success was this philosophy of flow, which is by, uh, uh, [00:12:46] OG: yeah, good luck. [00:12:46] Joe: Yeah. It’s pronounced Mihi Cheek Semi high, which is, I had to do it phonetically on my screen here to get that out. It’s all the [00:12:55] OG: letters in a random order. Yes. [00:12:57] Joe: But have you read Flow og? [00:12:59] OG: Uh, I’m, uh, do the abridged version. [00:13:02] Joe: Yeah. What Flow is all about is why do these people in an orchestra who are never gonna be famous. [00:13:10] Practice the violin over and over and over and over until their fingers bleed, and they’re gonna be one of 150 people out on a stage. Nobody’s gonna notice them specifically most of the time. Right? There’s, there’s a few that cut through, and even if they do, the top performers on the violin are not still well known to the average person in the world. [00:13:33] They certainly have a, have a fame base. We all see it in the things that we do. Even with board games, there’s a, there are board game creators where I’m like, oh my goodness, these people can clearly go into a target. Nobody’s gonna be asking for their autograph, right? Mm-hmm. Why do you design these things that they’re gonna create no money, they’re gonna have a small imprint. [00:13:51] Maybe 20,000 people will buy this thing. Why do they do that? And it all comes down to optimal life. I think this whole idea of Molly’s dynamic Drive is kind of built on this, which the quote directly from, uh. Mihi is the best moments in our lives are not the passive, receptive, relaxing times, the things OG that we think we’re dreaming about, right? [00:14:14] Oh, I wanna be on a beach somewhere. He’s like, Nope. Don’t get me wrong. Recharging the batteries fantastic. However, that’s not the optimal time, and I’ll continue with the quote. The best moments usually occur if a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile. [00:14:34] That’s a hell of a quote. I love that. Love, love, love that quote. But it’s not, when we think about retirement og, I mean, let’s talk about our goals. I mean, this goes to putting your goals down in the right way, way. How often do you see my goal in retirement is to sit on a beach. My goal is to not have to wake up at a certain time. [00:14:52] My goal is to not worry about the way that I eat and exercise anymore. I don’t wanna do any of those things. And it turns out when you look at the happiest retirees. Those things all suck for a happy retirement. [00:15:07] OG: I was talking to a client that recently retired. He retired quite young, actually. Of course, the big concern when you are done earlier than quote unquote whatever that traditional age is, you know, like, what are you gonna do? [00:15:20] Like, what’s the whole day look like? And we had a conversation a couple of weeks ago and I said, what’s your, what are you doing, man? Like, he’s a single guy, doesn’t have 15 kids running around that occupy him. He goes, he goes, I made a really strong commitment to my health and to volunteering, but I also wanna be in complete control of my time. [00:15:40] So I don’t sign up for volunteering. I show up for volunteering. [00:15:43] Joe: Oh yeah, I’m the guy that, they’re like, [00:15:44] OG: oh, awesome. We got another guy. And he is like, and I’ll do it for a little bit and go, Hey, I gotta, I gotta get, and they’re like, great. But he’s like, I go to the gym and I work out at my own pace for two or three hours a day and I, I just love the process. [00:16:00] Of really diving into all of this stuff around my health and wellness and strength and, and flexibility and, you know, all of the nuances that he said when I was working. I couldn’t, I, I, you know, I could get to the gym, I could pull out a half hour, 45 minute workout, two, three times a week and maintain, but I never had any progress because, you know, I couldn’t dive into nutrition and dive into, ’cause I was in between meetings and what do you do in between meetings? [00:16:29] You shovel in a can of ramen real fast so that you can go to the next presentation, you know, and what was interesting in talking with him was his day is every bit as busy as it was, what, you know, while his, you know, while his career was going on, lemme see this a little bit, Doug, for you, right? It’s like your day is every bit as busy as you were when you were working. [00:16:50] You’re just doing other things around family and you know, your property and exercise and. And that sort of thing. It’s not your, your financial independence time is not legs up, feet up on the couch and eating bon broth. Well, sometimes it is true, but it was when [00:17:10] Doug: I was working too. Exactly. [00:17:13] OG: Which may be why you’re not working anymore. [00:17:15] Honestly, too much bon bon time. To your point, Joe, I bet that if we asked, if we asked our stackers, those who are not fully employed, the ones that are financially independent right now, they’re every bit and, and happy. Every bit is busy. [00:17:29] Joe: That’s a great question. I know the people can give us, uh, comments on Spotify that we can chat about. [00:17:35] Can’t do that on Apple yet, but we can do it on Spotify. If you’re a Spotify listener, let us know if you’re that person or in our Facebook group, the basement, let us know if your every bit is busy as well and all the studies. I like what downtown Josh Brown from CNBC said when he was here that retirement planning is so young, we’re still learning, but the data as it’s coming in is like, it’s far more like a job. [00:17:59] Molly dives into actually how, how to create this drive to not just reach the stage, but then to excel. And obviously like everybody else, it’s not built on. Oh, she’s walking through the woods one day and comes up with this thing. She’s working on the shoulders of a lot of other people and a lot of research. [00:18:13] I remember a great book from 2003, which still holds up today by, uh, Jim Rohn, the big motivational speaker, Jim Roh and Tony Schwartz. He, uh, has written Tony Schwartz Big Thinker, co-written a bunch of books. Tony Schwartz actually even published a Harvard Business Review about their study back in. 2003 around the power of full engagement, which is the tactic to getting more flow in your life. [00:18:37] OG is around not managing your time, but managing your energy. Mm-hmm. And they compared the average person in any workplace or any life to a tennis player. Tennis players have tournaments all year round. And their big point was you can’t show up for every one. And if you’re, uh, working in a corporate environment or even with your family, you can’t show up to everything equally just on stage every time there has to be a recharge period, there has to be a time when you’re working on your skills so that you can show up better at those things. [00:19:08] And so they recommended a calendar where you spend your time focused on those things that are gonna make those highlights of your year even better. Like what are those things? So I can show up optimally at these four huge points in my year. Everything else that I do. So if I’m a tennis player and I go to, I, I don’t know, Cincinnati, I’m on my way to Cincinnati this week for economy. [00:19:34] So we’ll see scoreboard. There’s a thing in Cincinnati and I’m just gonna work on my forehand the whole time. I’m there like that. Is that that that is what I’m gonna work on. Uh, if I’m a tennis player, Doug Tennis player. [00:19:45] Doug: Oh, okay. I tuned out there for a second and I came back and I thought, I think you’ve worked on that enough, Joe. [00:19:52] I think you got it mastered there. [00:19:54] Joe: Let’s get back. Molly begins with our enemy and our enemy. Once you get past not having a house or not having a food is complacency and the way to knock yourself off complacency. She’s got seven steps. Her first one OG, is mindset. And it’s funny that you talk about trusting the process and about how people get into the process. [00:20:14] And this is the first thing she immediately goes to Carol Dweck. And this how, how many times have we referenced this book for any stacker that hasn’t thought about growth mentality. Guest after guest, after guest talks about it all begins with having this growth mentality, which means, where am I wrong? [00:20:33] Stop defending how you’re right, and instead ask yourself, where am I wrong? Of course, it’s horrible to shame people into, well, you’re wrong. You’re wrong. But when it’s yourself and you’re looking for your Achilles heel in your plan, that is huge. Now, Dan Sullivan, you and I have gotten help from Strategic Coach for this great coaching organization. [00:20:53] They also talk about OG living in the Gap, right? Versus living in the game. Can you talk about that concept? ’cause I think this has a lot to do with mindset as well, when you’re starting off to peak performance. [00:21:07] OG: Well, I think that the big struggle for most people is not appreciating where you are from, and instead always focusing on where you’re trying to get to and when you look to the future for all of your goals, whatever they are. [00:21:23] Physical or financial or professional or relationship or whatever, you’re always measuring it against this like ideal outcome, right? Like this thing that in a perfect world, all of these things are going on. To have all of those things exactly perfect is pretty rare and maybe even impossible. But instead, if you look from the back and say, how, where are we coming from and how far have we gone? [00:21:52] You know, and you’re looking at, for example, your retirement projections and you’re like, okay, I need to get to 2 million. And you’re sitting there with 190,000 in your IRA, like 2 million seems like the impossible goal. And it’s very easy to look at that and say, oh, it’s just not even worth it at this point. [00:22:12] There’s no cha, I did the math a thousand ways. I need 2 million. I’m at 200,000. Under no circumstances do I get there in my lifetime, or anyone’s lifetimes for that matter. So f it. But you forget that at one point in time you had 20,000 and somewhere along the line, through your contributions, through market growth, through time, you 10 times your portfolio already, right? [00:22:35] You went from 20,000 to 200,000. And I guarantee when you’re at 20,000, somebody saying to you, someday you’ll have 200. You’re like, yeah, okay, sure. Whatever bud. Whatever you say. Money guy. All right. You know my challenge to everybody recently, you know we’ve talked about this a little bit in some review times, is I know you look at those projections and you can do this on an Excel worksheet. [00:22:57] Here’s how much I have, here’s how much I’m contributing, here’s how much I expect by portfolio to grow, grow, and draw it out. And then you see this number when you’re a hundred and it’s like $10 million or 8 million, 5 million, 80 million, whatever the number is, right? You go, okay, that’s bull crap. Ola. I believe next year’s number May in the year after, but there’s no way that this, you know, maybe my great grandkids will see this number, but not. [00:23:19] Math is math, right? And so looking into the future is very difficult when considering compounding. Instead, look at how far you’ve gone over your lifetime, or look at how far you’ve gone in the last 10 years. I give you that 10 year example of, you know, looking at, looking at your income, look at your net worth over the last decade, look at your net worth over the last half decade. [00:23:40] And you say, how? Why would it be impo? You know, I’ve, I’ve three Xed it since 2020. Why would it not be reasonable to assume that I would three x it in the next decade? You know, I’ve already demonstrated the ability to do it like it’s already happened, right? Yeah. So why wouldn’t it happen again? Like I just have to do the same things and I, it’s reasonable to assume. [00:24:02] Now, obviously you go, well yeah, but the market was up 20% a year for the last five years and it’s not okay, I got that part. I understand that was a tailwind for sure, but it’s reasonable, right? It’s not exactly gonna be the outcome, but it’s reasonable to assume. [00:24:15] Joe: This is where I love the phrase you used earlier, loving the process. [00:24:20] Because the whole concept of flow, the whole concept of dynamic sustainable drive is that I’m not as attached to the outcome. Don’t get me wrong. I got outcomes that I want, but I’m not as attached to the outcome as I am a process which will create the outcome. And I’m passionate, not as much. I’m passionate about the outcome, but I’m much more passionate about the process. [00:24:40] How would a guy in sports like Tom Brady have won Super Bowl after Super Bowl, after Super Bowl, if he reaches the first Super Bowl and goes, yeah, I did it. I mean, that’s results focused, right? If I’m results focused, I win one Super Bowl and I’m done. Yeah, Brady gets done. LeBron James gets done. All of these, all these top athletes get done and they are added again, looking at the next, uh, next hill. [00:25:02] OG: I mean, there’s so many examples with sports or life around this that’s translatable to money. I mean, we’re, I mean, just talking with, with my middle kid about, about sports in school, he’s, you know, I don’t think he’ll mind me saying this. He’s, he’s a 15 going on, 16-year-old boy. Both of you have had that before. [00:25:22] There’s a little bit of an emotional rollercoaster that goes on around this time. Just a slo. Yeah. When Alex, who’s about to turn 18, he seems to be past it. And I’m not saying that he’s not gonna have ups and downs also, we all do. But William is right in the middle of it. I mean, to the point of like, what’s the point of all this? [00:25:39] So what I get a’s in classes, maybe I’ll just get b’s. Does it really matter? I don’t even know what my job’s gonna be. I don’t even know what, how to do taxes. Like that was like literally the jump that he made yesterday was, why do I have to get A’s and B’s? I don’t know what my job’s gonna be. And oh, by the way, I don’t know how to do taxes. [00:25:56] It’s like, okay, hold on, we’ll get there buddy. Like pump the, you don’t have to have the answers to everything right this second, but you have to trust me and you have to trust your teachers and your pe, the people around you. That getting A’s and B’s is a good thing because it will help all these other dominoes that are falling. [00:26:12] And whether you’re talking about sports, you know, going, Hey, you just need reps. You need to. You know, have at bats, you have to, you just need to show up basically and not worry about am I getting a hit? Am I getting an A? Do the steps. And the same thing is true with money. It’s like, yes, you have to max out your 401k. [00:26:30] Yes, you have to max out your Roth. Yes, you have to max out your HSA and your spouse’s stuff. The whole way to think about this isn’t necessarily, how do I get to 2 million? It’s how do I do the thing today? A hundred percent. How do I, I deal my, make my life so that I have a great, I have a great life and I’m doing the steps that for the next 25 years are gonna put me in the right spot. [00:26:50] Joe: This is why milestones are so important, is so that you don’t live in that gap of, oh, I’m not there. I don’t know how to do taxes. Yeah, I don’t, I don’t know My next step, I don’t know my thing if I build, it was [00:27:00] OG: so funny, I almost spit out my coffee when I said, said that, and I don’t even know how to do taxes. [00:27:04] I’m like, neither does half of America. So [00:27:08] Joe: welcome to the rest of your life. But this is why milestone your goals. I think it’s so important, especially those, those big goals, Doug. [00:27:15] Doug: Well, you know, I was gonna chime in, but I think it, it may be redundant, but I know when, when my guys were in high school and sports was a big part of their life, one of the things we did to take the results out of the. [00:27:27] Equation and reduce the rollercoaster effect was to not focus on the results of the game, but to have them focus on some detail of the process of that game and let everybody else play the, did I get a hit, did I hit a home run today? Did I win that race? And it was more about focusing on some smaller details and it took the stress out of it. [00:27:50] Let let everybody else play the stress game. You’re just focusing on, did I see eight pitches at this at bat? Because that’s a huge success. If you can make that pitcher throw, I’m using a baseball example that was big in our house. Did I make that pitcher throw eight pitches, let my teammates see eight pitches of what that guy then I, that was a successful at bat, even if I struck out because I just helped my team because they all just got to see all of the pitches that this guy had because he couldn’t get me out. [00:28:15] So he starts throwing every pitch he’s got. And that’s a different kind of success. The one everybody else thinks about is, did I retire with $16 million? That may be success for them, but it might not be success for you. And so there are different measurements there that you can think about in your process that can help you find some small successes along the way. [00:28:37] And who knows, you might end up with 16 million, but not if that’s the only thing you think about. [00:28:41] Joe: Loving that process and loving the fact that I’m working on that one thing and I’m enjoying the fact that I’m trying to get the guy to throw me eight pitches, I think is a huge thing. Which leads us to number two, I wanna talk about before the break, and then we’ll do the other five. [00:28:53] Energy is Molly’s number two and creating dynamic drive. So we start off with mindset. Where am I wrong? What do I need to learn? What do I need to do? How do I set up milestones and how do I not live in the gap? Number two is energy. Sam Altman from chat, GPT Fame, OG said this quote, you never feel burnout when you’re working on the right stuff. [00:29:14] This is, we’ve got a case study right in front of us this week and last week, assuming that by the time this comes out, the stock market hasn’t recovered 1200 points. The amount of bullshit, hand rigging I’m seeing from people because they’re focused on the wrong stuff. OG this, this is an energy drainer to wake up and go, oh, I, I saw somebody go, I’m four years away from retirement. [00:29:37] Carrie Stacker in the basement was talking about a friend at work. He goes very proud of the fact, she’s like, oh, my husband just took all of our money outta the stock market so that if this gets worse, oh, you are dealing with the wrong stuff. Even if that works outright, og, that is such an energy burn for no payoff versus how do I sustain doing the right things toward my goal? [00:30:02] And if I have this goal, I. That I’m trying to reach and I’ve got the milestones built up, I’m gonna have a lot of energy around just continuing my process. And by the way, if you’re feeling that consternation, I think the best thing to do last week would’ve been to go, is my process really serving me because I’m on Facebook talking about how I’m loading up on gold? [00:30:24] That is just, that’s such an energy drainer. [00:30:27] OG: Well, and for some people, that whole thing isn’t energy producing and automating it makes it so that you can focus on the other things. Yes. Other things that are energy producing for you. I mean, that’s one of the things about that book flow that you’re talking about. [00:30:43] It’s like if you have the opportunity to do things from a scheduling standpoint and from a time standpoint in the manner that suits you best, I know that I do my best work from roughly nine o’clock in the morning until one. So sorry. If you have a meeting with me at two, you know, or a podcast recording at three, by that time, this is the best show of the day. [00:31:07] This one and the one we do next. And then by the round table at three o’clock today. You know, but that’s me. And some people have different times during the day when they’re better suited to do different things. And so, um, managing your energy in the day to day, but also big picture, you know, you’re using the tennis analogy or whatever before it’s like, [00:31:29] Joe: yeah, [00:31:29] OG: don’t cheat yourself on free days, on vacation days. [00:31:33] That’s designed to recharge the batteries. If you, it’s funny, my kids and, and I’m usually pretty religious about this, but my kids said, Hey dad, next week can we go on spring break? Are you gonna take any work with you? I haven’t in years, but there was a period of time where I would go on vacation, bring the laptop, do work, do meetings, go, Hey, I can’t go to the beach right now. [00:31:53] I’ve got stuff to do. Probably the last time I did that was maybe five or eight years ago. That’s still like in their mind like, oh well there’s some chance we’ll go on vacation and dad will just sit back in the hotel. And that’s draining for them. That’s not the experience that we want for the family. [00:32:07] So use your free days if you are lucky enough to have a week off or you know, a weekend or whatever, like use those free days to recharge your batteries so that you do have the energy to get into. [00:32:18] Joe: Of course, all this stuff we talk about dovetails when you get these experts and Eric Alman, we talked to the first week of 2024 and he talked about cowboy fencing, those important times. [00:32:28] Oji. So if you know that you’ve got your peak energy, why are you wasting it on email? Right? Why are you wasting it on um, inconsequential stuff when you know when you work best fence off that time. So it’s only the stuff that makes sense. And then also fence off the time when you gotta recharge the battery. [00:32:46] ’cause if you don’t do that, it’s gonna show up crappy. Later it will show up crappy if you don’t fence off vacation. It’s just gonna show up in your work. And, and I also think burnout comes from, you know, I’ve, uh, I gotta choose my insurances, or I gotta do a budget or look at what’s going on in the stock market. [00:33:04] I think if you’re goal oriented and you’re just looking at the milestones, I think then choosing insurances, you are like, okay, based on my goal, uh, yeah, okay, this is kind of fun. Choosing the right insurances. Budgeting, I know what I’m budgeting for, I’m budgeting, so I’m focused on these things that I value and not these other things that I don’t. [00:33:25] All of a sudden all these things that seem tiring and energy drainers all of a sudden have purpose and meaning because of the fact that I’ve got this financial plan that has milestones and has meaning and is based on the stuff that I’m really wanna focus on. We’ve got, uh, five more. And now that we’re in it, I think we’re rolling. [00:33:45] These ones are gonna be a little quicker, but we’ll cover those in the second half of the show. Time for us to take a little break here because Doug, speaking of sports, you’ve got some sports related, uh, trivia today, I think. [00:34:00] Doug: Hey there, stackers. I’m Joe’s mom’s neighbor, Doug, and happy St. Patrick’s Day. It’s a day when we celebrate being in the green, if you know what I mean. Seriously. Here’s exactly what I mean. I’m wearing this incredible green shirt Joe gave me and sampling Joe’s mom’s mystery Green Punch. She’s been fermenting in the back of the fridge all year. [00:34:18] He’s delicious. I might add Greg stuff, ma. So, uh, onto the trivia, you know, with Molly, that’s a great Irish name right there, coming to join us on Wednesday. I thought maybe she’d help me solidify a baseball contract if I could show her my incredible curve ball. I’ve been throwing a few down here by the peaches and just check this out. [00:34:38] Sorry, mob. I’ll clean that up in a minute. Well, I’m gonna tune that up just a little bit more. Maybe I haven’t had enough of a punch yet. Yeah, that’ll help me. One sports agent you may have heard of is Scott Boris. I can’t even say that guy’s name without thinking about Todd down at the Sizzler. Both of those guys grind my goat. [00:34:58] Ugh. Ah, sorry again, ma. I got it. Okay. All right. All right. Before she comes down here, let’s get you some trivia. Scott. Boris recently helped one baseball player grab the biggest contract in history. On December 8th, this player agreed to a 15 year, $765 million contract with the New York Mets. Wow. With the Mets, amazing history of winning. [00:35:24] I’m not surprised they paid that much. What Mets fans too soon. I think I need a little bit more of that punch. Here’s the question, which player snagged that deal? I’ll be back right after I, uh, after I cleaned up some peaches. [00:35:46] Hey there, stackers. I’m Curveball thrower and a guy with two glass slivers in his pinky. Right now, Joe’s mom’s neighbor, Doug Scott Boris, AKA. The Darth Vader of Sports has locked down some huge deals during his career. Back in 2020, he helped Carlos Correa grab a three year $105 million contract with the Minnesota twins. [00:36:09] Boris helped him double that number two years later to over 200 million. Not a bad payday for my least favorite agent, but today’s question in honor of Molly Fletcher joining us on Wednesday. Which baseball player did he help sign the biggest contract of all time for $765 million? It’s none other than baseball player Juan Soto. [00:36:33] And now back to two guys who are the Hank Aaron and Babe Ruth of money mostly. ’cause they’re pretty old. Joe and og. We [00:36:42] Joe: even mentioned the distinct Patrick’s Day. [00:36:45] Doug: I’m a little more focused on the, uh, recreational activities today than you guys might [00:36:49] Joe: do. You, you, you totally must be. Yeah. I I was like, why has he got mom’s punch? [00:36:54] Why did mom make a punch number one? But number two, Doug, you look at that green shirt I, I loan you and that awesome letter on the front. You loaned it to me. [00:37:03] Doug: The, oh, that was the one that I used to start the fire with. Uh, easy to warm up the house this morning. [00:37:10] Joe: Go Sparty, spart on. By the way, sports agent Molly Fletcher, also a Spartan, which is why she’s amazing. [00:37:18] I wanna dive back into this idea of dynamic drive. We start off with mindset. What is my plan? Where might I be wrong? Where might the Achilles heel be in my plan? And how do I create a process? Second, then controlling your energy. Third is discipline. And what’s funny, OG is that for, for us, I think discipline when it comes to money is overrated. [00:37:42] And what I think the key to discipline is, I think there is a key component of discipline. If you’re trying to manage money well, and it’s the discipline to do just the thing that’s gonna make it. So you need no discipline. Like that’s the, that is the thing I love. Uh, I was reading about creativity from, uh, choreographer Twila Tharp, and she was talking about how she schedules a car. [00:38:04] She lives in Manhattan. She schedules a car to come get her at 5:00 AM and that is all the discipline she needs because once she gets in the car, the car takes her to a gym. When she gets in the gym, she’s not gonna not work out. And so she works out every morning, but it’s because she had the discipline OG to schedule the car. [00:38:23] I think that’s where we get it wrong. We think that every day we gotta show up with a bunch of discipline to not show money or not eat the pizza or whatever it is. And instead, if we just create these wind conditions that make it so I don’t need discipline, I think life goes a lot better. [00:38:37] OG: Well, it’s in the system, right? [00:38:38] And I think we’ve already talked about that. It’s like if you can figure out a way to set up a system that makes it so you don’t have to worry about the system, like you said, yeah, then that makes life a lot easier. Automate as much as you can, whether it’s around money or your time or whatever the case may be. [00:38:55] Doug: Yeah. Joe, I know you love the Twila Tharp example. We’ve talked about that before and I usually respond with my favorite example about the, the ultimate system. In process engineering often gets talked about as the factory of the future, which is it only has one man and one dog. The man is there to feed the dog, and the dog is there to keep the man from touching the machines. [00:39:21] That is what you want to set the process up [00:39:23] Joe: perfectly and then don’t mess with it. And this supply stackers in so many ways. What do you do with your direct deposit that makes a difference? How do you make sure that if you forget about a credit card bill, that at the very least it gets automatically paid to your credit doesn’t go down? [00:39:39] What is your system for making sure that you check that your homeowner’s insurance is the right amount? Just these things, instead of thinking about the discipline to do these tasks, which can be an energy drainer. Mm-hmm. Instead, focus on your energy on the stuff that you care about. Which brings up OG number four in Molly’s list, which is curiosity. [00:39:58] And this is where you find a lot of people get to the point that they don’t have the results that they think that they would, and it’s because they truly don’t care about the thing that they’re chasing. They don’t care about it. They think that they should or they have to. I’m thinking about her friend, uh, SUNY Rao who works with Paula over Ford, anything. [00:40:21] SUNY was a professional tennis player. Her parents, as she was growing up, were all about tennis. By the way. I’m not speaking outta turn. SUNY tells this story to everybody. She was on this grind of, I need to be good at this thing. I have to be good at this thing. I’ll let other people down and she’ll be the first to tell you g that when she gave that away and said, what makes me curious? [00:40:42] What am I excited about? Real estate investing is what she gets excited about. Her whole life changed and all of a sudden now she’s on this path. Not to extreme wealth. I mean, maybe that comes with it, but I don’t think SUNY does real estate for extreme wealth. I think she does real estate ’cause she’s addicted to it and she thinks it’s super fun to be somebody’s landlord and to own these houses and, and, uh, treat her tenants well. [00:41:09] And Doug, really, I guess I should point to you on this one because you’ve ranted about this before. Ranted Joe, well, Tom Peters, management guru, Tom Peters has always asked the question in brand, you one of his big books. He said, why do you wait for your boss to design a plan for you? Yeah. I think that’s what curiosity gets to, right? [00:41:26] Don’t do stuff because you think you should or whatever. Think about what makes me curious and how do I drive my own career? Am I learning around that thing versus going to you or somebody else and going, Hey, could you, could you create a, a plan for me to get to some place that I don’t really care about? [00:41:45] Doug: You’re right. I have ranted about that, and now you’re gonna get me going all over again. It’s just like, you know exactly what buttons to push because that does drive me crazy. But you rant about it [00:41:54] Joe: because it’s important. It is. It is so important. Why are you waiting for somebody else to control your life? [00:42:00] And if you’re curious at all, you’re gonna make moves that give you more drive. I [00:42:05] Doug: know why it happens. I mean, when you think about the, the general progress or path that most people start on or stay on for a lot of their life, at least in, in the western economy, is you go to school, your day is planned out for, you have a very prescribed set of things you have to do every day. [00:42:22] The, you know, this class to this class, to this class, you get, oh, maybe you do a little recreation, then you’re doing your homework. You do that for 17 years. And you go to work with some company and they’re prescribing, we need these tasks done by the end of the week. It just, you get into that repetitive kind of a of a environment and you think, well, somebody’s gonna tell me what to do next because that’s exactly what’s been happening to you for the previous 25 years. [00:42:47] bit: Yeah. [00:42:47] Doug: Even if that’s your chosen way of earning an income, you’ve gotta find a way to break yourself out of that and realize you are driving your bus [00:42:56] Joe: own brand. You Yeah, a hundred percent. [00:42:59] Doug: Yeah. [00:43:00] Joe: Then that road, no matter what road you take, is gonna be a little bit rocky, guys. So Molly points at resilience is next. [00:43:08] You have to be able to weather the storm. And it’s funny because we think that the way that we. Whether the storm is by buffering ourself from anything bad happening. This is a recent talk by, uh, well, it’s time for our TikTok minute. This is the part of the show where we shine the light on a TikTok crater’s either doing something brilliant or air quotes brilliant. [00:43:31] Oh gee, I think I just, uh, already gave this away, but do you think we’re about to your brilliance or air quotes, brilliance, [00:43:38] OG: say air quotes probably. [00:43:40] Joe: Oh, come on. I totally gave it away. This TikTok creator just brought their phone to Jensen Wong, the CEO of Nvidia, talking about the role of resilience on a big stage. [00:43:52] Let’s listen into what Jensen has to say about resilience. [00:43:55] TikTok: People with very high expectations have very low resilience, and unfortunately, resilience matters in success. I don’t know how to teach it to you except for I hope suffering happens to you. And I was fortunate that I grew up with my parents providing a condition for us to be successful. [00:44:14] On the one hand, there were plenty of opportunities for setbacks and suffering. And to this day I use the phrase pain and suffering inside our company with great glee. And the reason, and I mean that, you know, boy, this is gonna cause a lot of pain and suffering. And I mean that in a happy way because you want to train, you want to refine the character of your company. [00:44:33] You want greatness out of them. And greatness is not intelligence. As you know, greatness comes from character. And character isn’t, is informed out of smart people, it’s formed out of people who suffered. [00:44:44] Joe: It’s incredible. I don’t know about the leadership efficacy of the second half of that. Let’s make sure there’s a lot of suffering. [00:44:50] I think, uh, might have some pushback about that. But the first part, og, the fact that he calls pain and suffering. Opportunity is where he meets Molly here. Molly’s like pain and suffering is an opportunity. You don’t get better when you’re high fiving yourself about how brilliant you are. You get better when things aren’t going the way that you want. [00:45:10] You have an opportunity then to restructure that system, that process that you’re in love with to make it work better. [00:45:17] OG: Well, the other thing is, is that all of that is just a mental model. You know, if you think that you’re suffering, you are. If you think that you’re dealing with something above and beyond, then you probably are. [00:45:31] And just as easily as you think that you can think other things. And it sounds really trite to say that, you know, that it’s just, it’s all in your mind. But whether, uh, what’s the phrase? Whether you think you’re, [00:45:42] Doug: whether you think you can or think you can’t. [00:45:43] OG: Yeah, you’re right. That sounds good. We’ll go with that one. [00:45:46] Yeah, [00:45:47] Joe: that is it. Given Doug’s motivational speech and with Marsh Madness here, we have to have two of these. This is uh, a coach who’s been in the news a lot lately. Rick Pitino back with the team St. John’s, which has done a lot of stuff this year. That hasn’t happened in a long time. I [00:46:03] Doug: thought for sure you were going to Tom Izzo, please play this. [00:46:05] Thank you. [00:46:06] Joe: We’ll let Molly go to Tom Izzo on Wednesday. I’m sure the Pat two Spartans in a room. We’ll talk about Tom Izzo a little bit there, Doug. But for now, let’s go to Rick Patino and resilience talking to his team at halftime. [00:46:17] bit: Every time you miss a shot, you’ll game the flight. We don’t care about your mid shots like you guys keep blowing. [00:46:24] Opportunity upon opportunity upon opportunity. You’re like children with, with bad things happening. Instead of digging in and be tougher, you wilt. Where is your toughness? Don’t you know what adversity is all about? That’s a game of life, not the game of basketball. You don’t get down when things go wrong. [00:46:44] You digging and get tougher. Your whole life’s gonna be adversity. Learn how to deal with it. He, [00:46:50] Joe: he maybe could have done that with a few less FBOs, but I love the idea, Oog, that he takes this, this silly game of basketball and turns it into a life lesson that, you know what? You guys are doing this stupid stuff out on the basketball court. [00:47:04] If you can’t do it on the basketball court, how the hell are you gonna deal with life? Mm-hmm. Life is adversity after adversity, after adversity. And when you realize it’s gonna be there. What’s that book you love that book? OG The Road Less Traveled. [00:47:15] OG: I mean, it’s a super old one. But yeah, there’s a lot of stuff in there that just, you know, just life is life, you know? [00:47:21] Like it’s not good or bad, it’s just you just are where you are. Both of you guys have had sports kids who are very successful in those sorts of things, and y’all have your different ways of dealing with it. But, you know, like you can be excited for a period of time and then you can be sad for a period of time with whatever happens. [00:47:40] What if, with whatever’s going on. But eventually you have to like go to the next thing. You know, like Rick Pitino was talking about, if you’re playing a game and it just doesn’t go your way, it, you can be mad about it. You can be upset about it. You can pound your fists a little bit and that sort of thing. [00:47:53] Or the other way, if it does go the way that you hope, you know, you can be excited and that sort of thing. But if you don’t, if you don’t let that go and go to the next thing, you’re just always gonna be living in that spot. And some people are quicker at this than others, but this is kind of the piece on what Molly’s talking about here. [00:48:10] It’s, it’s acknowledge where you are, but then. Get on with it. And if this is about money and you’re like going, but you don’t understand, I’ve got all this money. It’s like, I get it. We’ve all been there. Maybe not all of us, but I certainly have. I’ve said this many times, whatever dumb thing you can do with money, I’ve done twice. [00:48:28] So trust me, I know what to, I know where you’re at, but you know, get on with it. Stop your belly aching like let’s go. You know? It’s gonna be [00:48:36] Joe: adversity and all you can do is what you can do next. You can’t bathe in where you’ve been. What happened? [00:48:42] OG: Yeah. Market’s gonna go down. It’s okay. I get it. It sucks. [00:48:46] You’re four years from retirement, some of your money just went away. I wouldn’t be excited either. [00:48:51] Joe: Number six on our list is connection. I’m not gonna spend a lot of time here because we’ve spent a lot of time here lately on past episodes. Go to our episode with Benjamin Brant recently, especially if you want to talk about connection. [00:49:01] But Molly says, think partnering over transactions. If you’re transaction oriented, that’s not a fulfilling existence and it doesn’t give you more drive. It doesn’t give you sustainability, but when you feel like you’re actually useful helping somebody. Remember OG Alex Ozzi said this. He said the key for him is be useful if I’m more useful than the next person. [00:49:22] Yeah. Solve problems. I go to sleep every, yeah. Go to sleep every day thinking about how great my life is. ’cause I got to help somebody and you’re making money doing it. [00:49:29] OG: Yep. Solve problems for people. [00:49:32] Joe: Number seven then is all of this leads to confidence. And you and I have seen this in Strategic Coach, that, uh, competency, working through mindset, energy, discipline, curiosity, resilience, and connection, that builds confidence. [00:49:49] ’cause now your energy’s in the right place. You’re focused on problem solving what you can handle, not what the world around you is doing. But what, what can I do? I’m focused on that and I’m focused on the machinery. As much as I’m focused on the outcome, I’ve set up milestones. So I’m celebrating along the way. [00:50:04] I have enough discipline just to continue to work on the machine and not touch the machine. I love that analogy, Doug. And then finally, build connections to be useful for people. And that all builds confidence. And I’m gonna give you a little preview of, uh, Molly. Molly had this to say recently on a YouTube short about. [00:50:25] What you should do to help you build confidence [00:50:28] bit: if you struggle to stay motivated, which is super normal, right? Totally normal. We all do. Try this, do this. Pause. Pause after every milestone, and tell yourself, I’m headed in the right direction, right? I’m headed in the right to direction. See, when you do this, you literally release dopamine. [00:50:46] It drips into your brain and it tells your mind and your body. It tells it to keep going. It helps reset that engine of motivation that we often, so often we all need. Try it. [00:51:00] Joe: And there it is. Living in the game, og. Living in the gain, I’m going in the right direction, and there’s confidence to keep. I just wanna [00:51:06] OG: drip dopamine. [00:51:07] That’s all I wanna do. Yeah, [00:51:08] Doug: that’s the image that stuck in my head from that whole thing is, oh my God, it’s dripping in [00:51:13] Joe: my brain. Well, that’s the sad thing is right. There’s a science behind this, which is kind of gross for a bunch of finance guys. My skull’s tapped like a maple tree in March. She’s ripping stuff in there. [00:51:26] Hey, we got time here for one more segment for a stacker who said, you know what? Better, call us all. See Hi N og. This is the part of the show where we shine a light on a stacker who needs some help. And if you need some help from og, head to stacky Benjamins dot com slash voicemail and you can be as cool as Alex who, oh gee, Alex has this, uh, tax planning question. [00:51:49] caller: Oh, hey guys. Alex here. For the first time ever, I went to pull money out of my brokerage account with Vanguard. It started giving me options about. Do I take it out as an average cost or a first in, first out, uh, highest in, first out all this minimum tax, all these random options. And I just kind of chose average cost ’cause that was default. [00:52:18] But after that I thought, man, is there a, uh, specifically I should be doing this, like to make sure I’m taking the long-term capital gains, you know, would that be a first in, first out one? So not sure if I made a mistake there, but curious if you guys have a specific way I should be going about this. If I just need to pull out 10 grand for a car car, 20 grand, you know, what’s the best way to approach pulling this money out? [00:52:46] Appreciate it. Thank you. [00:52:48] Joe: It’s a great question. Og, they all default to average. Is that what we wanna go with? [00:52:54] OG: Well, I mean, ultimately there, there is no right answer here, and it’s not a uniform answer. And certainly it’s gonna change depending on what’s going, you know, what the market’s doing. But basically what he’s talking about here is what do you wanna recognize as your cost basis on these transactions? [00:53:11] So if you’ve been putting money in, you know, a hundred dollars a week for the last 15 years, you have some shares that you purchased 15 years ago and some shares that you purchased a year ago, right? And some shares you purchased five minutes ago. And all of those have different prices. And so one of the ways you can do is you can say, well just average the price out of all of it, you know, so some prices were low, some prices were high, the market did whatever it did over that period of time, average the price, and then compare it against today’s price. [00:53:40] And, you know, if there’s a gain, then I’ll pay a capital or I’ll, you know, I’ll have capital gains on that and, and maybe subject to some capital gains tax. You can also, depending on the brokerage company, and every company’s a little different on how they deal with this, but you can also say, well, I want to pick the shares that I wanna sell. [00:53:58] So if I’m gonna sell something, I wanna sell the ones that have the highest basis. You know, I’m gonna sell the ones that are the closest to today’s price. Maybe the ones I just bought yesterday, because yesterday’s don’t have a gain. In fact, they have a loss and I wanna sell those because I need the money. [00:54:13] And then, then that has a different tax treatment as well. Because then if you have a loss, then obviously that shows up in your tax forms a little differently than if you have a gain. Or maybe you choose to say, I wanna sell the first shares that I bought. That’s the first in, first out. I wanna buy. I wanna sell the shares that I got, you know, back in 2010. [00:54:32] Then if I do that, then probably those are the lowest cost shares and I’ll have the highest gain potential. So there’s no right answer to this. You have to plan out what your tax bill’s gonna look like, and then decide what does this mean From a tax standpoint, you may not make enough income to have a capital gains tax this year on a distribution that you make, even if you have a capital gain. [00:54:56] So if that were me, I would say, well, I’ll take all the capital gains I can because I’m getting taxed at 0% right now. That would make a lot of sense to say, I’m gonna take a bunch of cap gains at a 0% tax rate. If that’s where you are in your tax fund, you may be, Hey, this is also the year that I got a bunch of RSUs vested and my income is at the highest level it’s gonna ever be because of all this extra stuff. [00:55:19] And a big bonus that I got, well, why are you taking money outta your brokerage account? You got a bunch of cash. I’m just kidding. But you know, so maybe you don’t wanna pay any capital gains. So it’s gonna vary. Depending on your, your very unique situation. So unfortunately, Alex, there’s no right answer to this. [00:55:36] You have to sit down with a tax person with your CPA, you know, maybe it’s 10 grand you go. I don’t really care that much to dive into it, but it’ll be a good exercise to do anyway, to really figure out which one of these is going to, um, have what impact on your tax forms. [00:55:53] Joe: Yeah. My bias OG is usually to try to find opportunities. [00:55:58] To pick those shares that actually have the biggest capital gain and get rid of those to make my life easier for later. We’ve, we’ve seen the studies that show that there’s this tax trap that a lot of retirees have that they don’t spend money because they’re worried about the taxation of that money. [00:56:14] So if I can make sure that I’m not as worried about that later, then I will often bias tort. So I gotta be talked outta that. The way I’m talked out of it is if I have a big tax bill that year, if I have, uh, nothing that I can use, you know, if I’m weeding the garden, so to speak, and I don’t have any losses, I can offset it with, I think that then if it’s just gonna be this big kapow in my gut, then there’s no reason for me to do those shares. [00:56:44] I might do what you mentioned, which is, okay, this year I’m gonna go with the shares that maybe have, have a, a loss as an example so that I don’t have to have to worry about the tax at this particular time, but. I think this is, this is a hundred percent subjective. Yeah, absolutely. Yeah. Thanks for the question. [00:57:04] If you’ve got a question for og, head to stacky Benjamins dot com slash voicemail and uh, you can be cool like Alex. And guess what? Alex is gonna go pick out some swag at our Stacky Benjamin store, some sweet sweet SB swag, which you can see over at, at the Stacky Benjamin store. [00:57:22] Doug: Why don’t you send him that special green shirt with the letter on the front of it and I’ll take the swag. [00:57:27] Joe: Be fantastic. Alex, would you prefer Michigan State shirt? I think you probably would. I think you probably would. Alright, that is going to do it for today. I am looking at the clock. We’ll have back porch, uh, stuff next time. We do have some Doug, we do have some community stuff we wanna share, but not today. [00:57:45] Coming up on Wednesday, you heard us talk about Dynamic Drive, the woman who’s behind the whole seven steps. We just talked about Molly Fletcher coming down to the basement. So can’t wait for you to hear it right from Molly, why this is important, her big point. And making sure that you get the most out of your drive and you’re not just focused on some sugary motivational talk, but much more on a sustainable way of keeping going and not just making it to the stage, but being kick ass when you get there. [00:58:12] Alright, that’s gonna do it for today, Doug, man, what’s our top three takeaways today? [00:58:16] Doug: Well, Joe, here’s what’s stacked up on our to-do list for today. First, dynamic Drive comes from focusing on the right tasks and with your money. That means having just enough discipline to build systems that’ll keep you focused. [00:58:30] Second, taking money from your brokerage account. Take into account your whole tax situation that year and plan accordingly while first in first out may be the biggest pain. Now, it may help you stay more flexible in the future, but your situation that’s gonna depend on your current tax situation and other tax strategies you can use to minimize the amount you owe. [00:58:52] But the big lesson. Don’t tell Joe’s mom, you were doing her a favor by knocking over her canned peaches. When practicing your curve ball, she’s gonna tell you that she’ll do you a favor by knocking you and I quote into next week. Sorry, ma. This show is the property of SB podcasts LLC, copyright 2025, and is created by Joe Saul-Sehy. [00:59:21] 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. 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. [00:59:43] 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. [01:00:46] Live from Joe’s mom’s basement. It’s the Stacking Benjamin Show. Okay, hold on. I just had a huge flashback reading that, and I just realized I had a dream last night where I kept having to say that over and over and over again. Oh my God. Did you really? Until I just said that just now. I forgot all of, you know, you’re like, oh my God, I can’t believe that. [01:01:15] And it was just like I couldn’t stand the sound of it in the dream. [01:01:21] OG: So now you know what it’s like for us for the less 1700 episodes. [01:01:25] Doug: I’m sorry, everybody. Okay then. We’ll, we’ll do it this way. Live from Joe’s mom’s basement. Ah, it’s the Stacking Benjamin Show. We’ll go like NPR. I like it. Are we starting over? [01:01:41] I dunno. I think at this point we’re starting over. I guess so. I [01:01:44] OG: like the whole thing. Keep it [01:01:46] all. I.
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