When Is "Good Enough" Actually Good Enough With Money? SB1884

There's a version of financial responsibility that looks a lot like discipline but can quietly become something else: an inability to ever stop optimizing. Chasing 0.2% more interest. Driving fifteen minutes out of the way for cheaper gas. Budgeting so tightly that a $5 bottle of multivitamins feels like a crisis. Wealthy Kids Club founder Maya Corbic joins Carol Ann Desiderio and Jesse Cramer for a genuinely fun debate about where the line actually sits, and what over-optimizing quietly costs when nobody's counting it. What You'll Walk Away With A simple test for telling the difference between smart optimization and time-wasting perfectionismWhy budgeting "until it hurts" can quietly damage your relationship with money more than it helpsThe real math behind small optimizations, like driving out of your way for cheaper gas or chasing a slightly higher savings rate, and when they're actually worth itA reframe on "one more year" retirement thinking that flips the entire question aroundWhy letting kids make small, reversible money mistakes teaches more than any lecture ever couldThe surprising overlap between "still researching the best option" and simply avoiding a decisionWhy the biggest lever in your investment returns has almost nothing to do with picking the "best" individual stockWhy This Matters Now It's easy to assume that more research, more comparison, more fine-tuning always makes for a better financial decision. But there's a point where that instinct stops protecting you and starts costing you, in time, in joy, and sometimes in the decision never actually getting made at all. Recognizing when a plan is genuinely good enough isn't giving up. It's redirecting your energy toward the things optimization can't fix: time with people you love, work that fulfills you, and a life that isn't built entirely around squeezing out one more percentage point. From the Basement A wild detour into the 1964 Great Plymouth Mail Truck Robbery keeps the crew's year-long trivia race razor close, while an entirely unrelated cookie heist upstairs in mom's kitchen proves that not every optimization scheme goes according to plan. Resources Mentioned Wealthy Kids Club https://wealthykids.club — Maya Corbic's family financial education programPersonal Finance for Long-Term Investors podcast https://pfltipodcast.com — Jesse Cramer's show, referenced episode: "Is My DIY Financial Plan Working?"Stacking Benjamins Benjamins After Dark meetups https://stackingbenjamins.com/bad — local in-person Stacker meetup groups, including BostonGranola https://granola.ai/sb — AI-powered meeting notes tool mentioned in the sponsor break See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

• 0:00Speaker 00

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• 1:03Speaker 02

  Good morning, Christopher Robin.

• 1:04Speaker 03

  Oh, good morning, Winnie the Pooh.

• 1:11Speaker 00

  Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show.

• 1:26Speaker 00

  I'm Joe's mom's neighbor Doug, and on today's show, I got my stopwatch rolling because I'm gonna time out this introduction to see how it goes. Seriously, in this world of optimization, do you think optimizing this intro is a bridge too far? Or should I tweak it even more? That's right. Today, we're asking, when is good enough, good enough? But that's not all, because we'll optimize today's show around my incredible trivia question. This one's gonna amaze your friends, so have them gather around. And now, a guy who loves impressing his friends by talking about just how old his car is, it's Joe. Oh, Saul Sehi. Dang it. I double tapped the watch at the beginning, and now I gotta do it all over again.

• 2:15Speaker 00

  Don't you hate that? When a good plan goes awry. Hey, everybody. I am Joe Saul Sehi. Happy Friday to you. We have a phenomenal, phenomenal show today. We have a fantastic cast. We're gonna talk about how do we actually pay attention to stuff? Should we optimize every little piece of our life? Or when is good enough, good enough? In fact, and I'll get into this in a minute, I wrote a Fast Company piece on this, which kind of made me think about a broader topic on this and around your money, because so often in the financial community, we see people optimizing. And a guy who's always optimizing, who you just heard, and we're gonna hear again, Mom's Neighbor Doug is here. How are you, man?

• 2:56Speaker 04

  Fantastic today, Joe.

• 2:58Speaker 00

  Optimizing the front end of the show. Feeling good?

• 3:01Speaker 04

  Well, we're still working on it. I've still got a team of researchers working on it. But there's, I try to optimize a lot in my life. Here's an example. You know, sometimes late at night, you just need something cold and crunchy. And usually, the answer to that is cereal, right? Like, it's tough to beat a bowl of cereal, like 10 o'clock at night, and you just.

• 3:23Speaker 00

  It's like the best worst decision ever.

• 3:25Speaker 04

  Well, I mean, I do it healthy. I do cinnamon toast crunch. So I thought, well, we could do this better, right? There's a way to optimize this. You want cold? How about we make it colder? Throw the ice cream in there.

• 3:35Speaker 00

  Oh, really?

• 3:36Speaker 04

  Turns out that's over-optimization. It does not. It doesn't work.

• 3:41Speaker 00

  Maybe not enough. And a guy who, speaking of ice, it is mid-August, and they're waiting for the first snowfall in Rochester, New York. It's Jesse Krabers here. How are you, man?

• 3:52Speaker 05

  I'm doing well. I'm doing well. It's still beautiful and summer up here. But I will say, a friend of mine, we were talking about trying to make maybe a hiking trip to the Adirondacks in like mid-October, which is upstate New York, beautiful mountains. But up at those elevations, mid-October, you are flirting with snow and ice season. And who wants to hike on an icy mountain? So it's coming sooner than we want it to come, Joe.

• 4:14Speaker 00

  Well, not here. It's 95 degrees still in Texas. So bring it this way, please, God. Gray, even in Mom's basement, where it should be nice and cool down here. It's still crisp 85. Hey, question. Are you a Buffalo Bills fan?

• 4:28Speaker 05

  Oh, yeah, I am.

• 4:29Speaker 00

  Speaking of winter coming, let's talk about this before we introduce the rest of our cast. Your Bills have a brand new football stadium, and apparently, it's already getting ripped for bad sightlines. And have you seen this, Doug?

• 4:41Speaker 04

  Everybody loves it. Tiny little screen. As big as your iPhone.

• 4:45Speaker 00

  Yeah.

• 4:45Speaker 04

  The jumbo drone.

• 4:46Speaker 05

  I take the summers off from following football. I'm a fair weather football fan, which is pretty funny, us speaking about the weather. But I'll have to look that up. It doesn't surprise me that people are already complaining about the nice new thing, though.

• 4:57Speaker 00

  I know. Already, already. You can't have anything good there. You can't have anything good. You know what is good, though? It's good when you can teach your kids about money. Also, and I'm super happy this woman's here, we have known her for a long time. She was one of the coordinators of our Benjamin's After Dark group in Boston. Carol Ann Desiderio joins us. Carol Ann!

• 5:23Speaker 06

  Joe, that was so awesome, the way you botched my last name like that. Thank you.

• 5:27Speaker 00

  So it's DeSiderio?

• 5:29Speaker 06

  It's DeSiderio.

• 5:30Speaker 00

  DeSiderio. What is a DeSiderio, DeSiderio among friends, Carol Ann?

• 5:35Speaker 06

  Hey, listen, I had to nail you on something. So here we go. Thank you for having me. Nice to see everybody. I'm happy to be here.

• 5:43Speaker 05

  Carol Ann, I think, didn't the Eagles write a song about your last name?

• 5:48Speaker 06

  DeSiderio?

• 5:48Speaker 05

  Desperado.

• 5:49Speaker 06

  Desperado.

• 5:50Speaker 05

  Never mind. Wrong word. We all make mistakes.

• 5:53Speaker 00

  But Carol Ann, you have had somebody say, a DeSiderio, why don't you come to your senses? Have you had somebody say that line before?

• 5:59Speaker 06

  Not until this very moment. So that's awesome. Thank you for that. I'm never gonna not hear that now every time I hear that song.

• 6:07Speaker 00

  You're welcome. Well, you're married to a musician, right? So.

• 6:10Speaker 06

  That's true. Yes, I am. Yeah, I'm sure Kevin can do something with that.

• 6:14Speaker 00

  Well, let's chat about that for just a moment. You are one of the members of our Bad group in Benjamin's After Dark group in Boston. So tell us about getting together with some other stackers in Boston. How's that?

• 6:27Speaker 06

  It's been so great. We've been going a few months now. We're playing with times and dates, just to kind of make things a little more accommodating for everybody. So we used to do it 6:00 to 7:00 PM. Now we do it 6:30 to 7:30. It gives people a little more time to get there after work. And we also have changed it to the third Wednesday every month, instead of the second, to make it a little more accommodating for people's work schedules. So we're new, and we're trying to get up and running and be a little more flexible. We're five months in, but we've had some great conversations and some repeat customers, including your own beautiful daughter, who comes to our groups.

• 7:01Speaker 00

  I gotta tell you, I love the young people that come. There's another awesome young lady who, we can give a shout out, her first name maybe, who I just met at our quarterly meetup, our national meetup. And I'm trying to remember her first name.

• 7:13Speaker 06

  Talking about Sue?

• 7:15Speaker 00

  No. Well, Sue's very young, but this is a woman in her 20s.

• 7:20Speaker 06

  Who?

• 7:21Speaker 05

  This is great radio.

• 7:22Speaker 00

  This is great radio.

• 7:23Speaker 05

  Yes, yes.

• 7:28Speaker 00

  I'm not gonna remember her name, because I only met her once. But she came to our quarterly meetup. She had come to your meeting maybe the month before. Maybe it was one that you missed.

• 7:35Speaker 06

  Oh, was she the school teacher?

• 7:37Speaker 00

  Yes.

• 7:39Speaker 06

  I can't remember her name. Oh, my God. This is terrible.

• 7:41Speaker 05

  What does she teach?

• 7:44Speaker 06

  Children.

• 7:44Speaker 05

  What's?

• 7:46Speaker 06

  Elementary-ish children.

• 7:48Speaker 05

  Good answer.

• 7:50Speaker 06

  She's one of the reasons why we're changing the scheduling of the meeting, because during the school year, it just doesn't work for her. And we're trying to make it accommodating for people to be able to come out. And we meet at Hannah's Brewery on Main Street in Melrose, which is an awesome place. They've been so accommodating to us. We love it there. It's a great space.

• 8:07Speaker 00

  Awesome. Close to public transportation?

• 8:09Speaker 06

  Close to public transportation, close to the commuter rail. If you're in the Boston area, you can get anywhere you need to be. We are on the orange line, but also the commuter rail. Boston people will know what that means.

• 8:19Speaker 00

  Yes. I was gonna say, if you're in the Boston area, come on out, take the orange line, the commuter rail, whatever it takes. Just come, hang out with Carol Ann and everyone else. All right. This woman not only runs the Wealthy Kids Club, she has only about a quarter of a million people following her on Instagram. Our friend Maya Corbic is back. How are you?

• 8:39Speaker 07

  I'm good. I'm very good. Thank you for having me.

• 8:42Speaker 00

  You just got back from a nice vacation. Someplace warm or cold?

• 8:46Speaker 07

  Well, I live in Canada, so it, I guess it was warm, but it was up north. It was further than where I normally live. So in the cottage country, it was lovely.

• 8:55Speaker 00

  Nice. Beautiful. Fantastic. Let's talk about Wealthy Kids Club. How does it work? What do you do?

• 9:02Speaker 07

  Wealthy Kids Investment Club actually helps families budget their money, manage their money better, and pursue their financial goals. Originally, it was kids-only club, but then I started noticing, because it's been operational for the last four years, I started noticing that parents were just kind of sticking their kids in the club, but they themselves did not really understand finances. And so it became a family-oriented club where other families can meet families like them. It's this lovely experience where families get together and learn about finances and get their money better.

• 9:37Speaker 00

  It's really fun. And that's what you lead to also, I think, in your Instagram videos.

• 9:42Speaker 07

  Yes. And it's funny, actually, because the Instagram videos are done in a way that kids can understand them, but I find that a lot of parents are learning from them too, because they didn't learn this stuff when they were younger.

• 9:53Speaker 00

  It is funny. I found that, Maya, just with Stacking Benjamins, is that we try to keep stuff one-on-one as often as we can, because we often think that people understand what up in Canada, like a tax-free savings account is, or a Roth IRA here, we just take that for granted. And many people don't, and they're afraid to ask, which, the more we do this, the more we find out. Well, I'm super happy you're here, and Carol Anne's here, Jesse's here. We're going to talk about optimizing your life. I read a wonderful piece at Fast Company about the power of good enough. When is good enough, good enough? And I wonder that around specifically, that was around your whole life, but specifically with your money and with your work life, like, when is it enough? And then Maya will ask you specifically

• 10:36Speaker 00

  as well about, you know, teaching kids about, you know, when we teach kids, are we teaching kids optimization? When should we teach them to optimize? And when is enough, maybe enough? So I can't wait to get into it. We've got Maya here, we got Carol Anne, we got Jesse, we got Doug. We are going to dive into this in a moment. We've got a couple sponsors, though, who help us keep on keeping on. We're going to hear from them. And then we're going to talk optimization and maybe over-optimization. How many meetings a day do you take notes in? Or how many different just events where you have to jot something down? Here's a hill I will die on. Granola AI is the best, the best note-taking software that is available. I've used a ton, and it is by far the best.

• 11:19Speaker 00

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• 12:04Speaker 00

  up your day, Granola is a no-brainer. You can try it totally free by heading to granola.ai/sb. That's granola.ai/sb. And get your time back. Here it is again. Try it for free. Granola.ai/sb.

• 12:22Speaker 00

  Well, you may know that Chaos is the name of the game here in Mom's Basement, what with guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug. The holidays make it even worse, because it's all about food and big meals. And the problem is, prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge, huge bookends? Well, that's where Factor comes in. Factor is made with high-quality ingredients that you recognize and trust with over 175 banned ingredients. You always know you're eating something that's good for you, even when you don't have time. It's ready in two minutes, whether it's lunch between meetings

• 13:03Speaker 00

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• 13:43Speaker 00

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• 14:23Speaker 00

  I was walking down the beach a few weeks ago. All of a sudden, I see my social media blows up with a gentleman named Stephen Bartlett. And Stephen Bartlett is the host of a popular show called Diary of a CEO. And Stephen had said on his podcast that three glasses of wine had completely wrecked his week, had wrecked his week. He had gone out with some friends. He had three glasses of wine, and now his entire week was a disaster. And immediately, everyone on social media, and I don't know if it was right or not, started saying, okay, are we just optimizing too much stuff? What a third glass of wine you can't appreciate with friends, because you're so worried about your productivity?

• 15:06Speaker 00

  You're so, so insanely worried about it. That was really what caught my attention to actually read this piece. Now, I'll link to the Fast Company piece in our show notes, but really, if you want to read it to dive deeper, you can, but you don't have to. But let's dive in with you guys. Maya, let's start with you. What is something that you, you maybe went off the deep end and went, you know what? This is Maya's, quote, "three glasses of wine" where you might have over-optimized?

• 15:32Speaker 07

  What comes to mind is budgeting and over-budgeting. So I grew up in poverty. We had very little money. And when I was becoming who I am today, I had some very low-income jobs, and so I had to budget every penny. That sort of stuck with me. But also, being in this industry as a financial educator, you know, we're constantly told that, you know, we need to budget and allocate every cent. And some people even say, like, budget until it hurts, which I completely disagree with now. I remember, my kids were very little, and I needed to buy some multivitamins. I remember going into a health food store and

• 16:14Speaker 07

  not buying the multivitamins, because I was going to go, I don't know, maybe $5 over the budget. It was ridiculous. I remember coming home, and my husband asking, where are the vitamins? And I said, well, you know, we were going to go over the budget. And he just looked at me, and he was like, are you kidding me? Like, there is enough money. Like, you can, you know, we don't need to budget this tightly. This is ridiculous. Like, we are optimizing for every cent, and there is no need for that. It's sucking out every joy and fun out of life. That was the moment when I realized I wasn't really enjoying doing that. I mean, I did that for many, many years, because I had to. But we were in a good financial place where that didn't need to be done anymore.

• 16:56Speaker 00

  And it's so wild that budgeting can be either a wonderful tool, or just this absolutely rotten thing. And so much like a money nerd, Maya, that you would, you're prioritizing wealth over health, you know, when you say that. Like, who cares if my kids are healthy? We need more money.

• 17:14Speaker 07

  Yeah. It sounded absolutely crazy. And I remember reflecting on it, and I thought, okay, this is nuts. Like, we need to change things.

• 17:22Speaker 00

  I love that you started with that one, because we often optimize saving money, but we don't think about time. We don't think about health that much in our personal finance community. Carol Anne, what's one where you maybe went a little off the deep end?

• 17:35Speaker 06

  Yeah, I actually can relate a lot to the story Maya just told. Thank you for sharing that part of your background with us. I came from a similar kind of situation where divorced at a very young age, raised two kids on my own. Money was always tight. It was always so hard to make ends meet, that you really did have to watch for every penny. But then what I did with my kids, once they were in college and out of the house or whatever, I ended up having to then turn around, and every spare cent that I used to spend on the children now got reallocated to making up for lost time, what I thought was lost time, catching up with retirement in savings and things like that. And I optimized.

• 18:15Speaker 06

  That's my vitamin alarm. I'm sorry about that.

• 18:18Speaker 00

  Time to take your multivitamin?

• 18:19Speaker 06

  Yeah, that was my multivitamin.

• 18:22Speaker 06

  But I optimized so much that I was got to the point where I had like a 67% savings rate from my salary.

• 18:30Speaker 00

  Oh, my goodness.

• 18:31Speaker 06

  It was such forced scarcity that there was never any money to do anything because I felt like I was catching up for lost time for all those years in retirement that I couldn't afford to save. And so I did have to get to the point where I was like, I gotta slow down. Why am I doing this? I've caught up to where I need to be. I'm in a good place. It's okay to have a little extra money so that I'm not counting every penny. I can afford to go food shopping now without using a calculator. Like, it's okay. And so it's a different mindset that you really, really have to wrap your mind around when, when does enough become enough? And you can slow down a little bit to just make the other areas of your life a little more enjoyable as well, because I'm at the point now where I've got more money than time.

• 19:15Speaker 06

  And that now becomes the problem or the concern.

• 19:17Speaker 00

  Yeah, time becomes, becomes, and then you think about the time that you may have, I don't want to say wasted, but spent the time that you spent on accumulating money, living this lifestyle far below, you know, what you could have done if it was more moderated. And I'm glad you brought up that story because that's also prevalent in the personal finance community, Carol Anne, with people, you know, especially in the FIRE community where they're like, no, no, no, have fun tomorrow. Today, we're going to make sure that we wring every penny out of this. Jesse, you've never over optimized anything, never overthought anything like as a guy that was an engineer, there's no way you overthought a thing. I never meet any overthinking engineers.

• 19:57Speaker 05

  I was trying to think of the funniest one, but there was a time where probably for like a couple of years where I tracked all the mileage on my 2012 Toyota RAV4. And I also tracked every single time I filled up at the gas pump and how many gallons it

• 20:10Speaker 00

  Wait a minute, okay, the first part, tracking your mileage, doesn't your Toyota RAV4 do that for you?

• 20:15Speaker 05

  Well, yeah, yeah, but, but, but my point is, you know.

• 20:17Speaker 00

  The distance it was giving you? It says 212.

• 20:19Speaker 05

  You need a spreadsheet for specific dates, Joe, for specific dates to say this month, this month, this month. And then simultaneous to that, I was tracking how much gas I would add and how much I would spend on gas. So that way I could calculate the running miles per gallon at any given point in the, in the life of that Toyota. And then, you know, how much I was spending on gas. I would be going down the throughway and they say what, that which gets measured gets managed. Like in order to improve on something, you ought to measure it. And so sure enough, the act of throwing all this useless data into a spreadsheet meant that as I'm going down the throughway, I would be like, okay, that tractor trailer is going 68 miles an hour and I'm pretty happy with 68. I'll just tuck in behind him to draft. Draft, yeah. Cause I'm tracking this data.

• 21:04Speaker 05

  I need to improve my mileage. So that was a couple of. As a hypermiler, exactly. Some people think about credit card points. I'm just all about mileage, baby. And so that was a couple of years of my life that I probably won't get back.

• 21:18Speaker 00

  But you've seen the backend of a lot of nice tractor trailers.

• 21:21Speaker 05

  Oh, my gosh, I know so many 1-800 numbers you can call if someone's driving erratically.

• 21:27Speaker 00

  Did you ever calculate how much money you saved by drafting off of tractor trailers?

• 21:33Speaker 05

  I mean, I will say for my little RAV4, my, my mileage in the moment, like, you know, RAV4 gets 26 miles to the gallon or something like that on average. But when you're there drafting, you're getting like 45, which again, what does that mean? It means that your, your, we'll, we'll say it doubles your, your fuel efficiency, which would cut your gas cost in half.

• 21:54Speaker 00

  Must have saved tens of dollars.

• 21:56Speaker 05

  I bet you I saved hundreds, maybe even, maybe even a thousand a year if I was doing it well.

• 22:01Speaker 00

  Before we go any further, I want to know exactly who I'm talking to, who we have on a scale of one to 10, 10 being that you are always thinking about optimizing and you gotta force yourself not to optimize, zero being you have to remind yourself once in a while that maybe a little optimization might help your life. On a scale of one to 10, Jesse, who are you?

• 22:24Speaker 05

  Probably a seven, I'm gonna say.

• 22:27Speaker 00

  Carol Anne, how about you?

• 22:29Speaker 06

  I, I don't know. I might be like a nine or 10 because every time I try to pull back on one area, it makes me realize I'm, or think at least that I'm not doing enough in another area. And so I'm always biting off more than I can chew.

• 22:41Speaker 00

  Always, always overthinking it?

• 22:43Speaker 06

  Always, yes. Cause there's always something more I can be doing.

• 22:47Speaker 00

  Maya, where would you put yourself on a scale of one to 10?

• 22:51Speaker 07

  One is where I have to remind myself, probably say I'm five. Like I'm really in the middle.

• 22:59Speaker 00

  Right in the middle.

• 23:00Speaker 07

  I, I do realize the importance of it, but.

• 23:02Speaker 00

  All right.

• 23:02Speaker 07

  So yeah, I, I do realize the importance of it, but I, I actually thrive that, you know, thrive sometimes on just going along and, and doing the main things that are important, but not really focusing too much on optimizing as long as I see some progress.

• 23:19Speaker 00

  Well, let's talk about kind of the cost of optimizing for a minute. Jesse, do numbers people have an especially difficult time accepting good enough because there's always a mathematically better answer?

• 23:30Speaker 05

  Could you rephrase that question for me, Joe? I think I understand what you're asking, but I just say it one more time.

• 23:35Speaker 00

  I feel like a lot of our stackers are mathematically oriented.

• 23:37Speaker 05

  Okay, yeah.

• 23:38Speaker 00

  Let's say that they are the 10 like Carol Anne. Do you think, because you see a lot of people when you're talking about financial planning, that numbers people have this difficulty accepting that being a five, like Maya said, is okay sometimes?

• 23:53Speaker 05

  Yes, yes, I see. Yes, excellent question. I love the question. I come from a world of numbers, right? I've got two degrees in engineering and I spent seven years working as an engineer. And the thing that math and the hard sciences tell you is that every equation can be optimized, right? Calculus, every, every curve has a maximum or a minimum menu. Anytime you're trying to design something in engineering, there's a certain way to get the, the strength to weight ratio as, as high as possible.

• 24:21Speaker 00

  Yeah.

• 24:21Speaker 05

  And, and right, you can kind of keep on squeezing for more and more efficiency. And I think that a lot of people who maybe have that mathematical bent to them naturally want to come into the world of money and apply the same exact thought process. I did for many, many years and maybe you could argue that I still do. It's just that when that world of money collides with that soft mushy stuff between our ears, you, you realize that you're no longer, you're no longer optimizing a mathematical equation. You're now trying to optimize mushy psychology and feelings and emotions. And it just breaks down. It doesn't work the same way. So I, I think, I suspect that a lot of this optimization tension that we're here talking about today has to do with where the, the math and the mushy brain start to collide

• 25:06Speaker 05

  and it just, it's gray. It's a gray area. It's gray matter, you could say.

• 25:11Speaker 00

  Mushy brain. You have a way with words, Kramer. Maya, I know that all kids are different, right? But do kids naturally begin as optimizers for the most part? Or do they learn optimization from watching us?

• 25:27Speaker 00

  And she's gone again. We're having trouble keeping Maya. Carol Anne, you've had kids, same question. Did your kids learn optimization from you?

• 25:36Speaker 06

  I feel like I've been a bad influence in this area on my daughter because what I noticed with her, she grew up always trying to, you've spoken to her before, Megan, she's wonderful. She's 30 years old.

• 25:48Speaker 00

  Megan's been on the show.

• 25:49Speaker 06

  Smart and successful and she's a great kid. But she always grew up thinking, I gotta do more, I gotta do more. And I think she learned that from watching me. And so when she was in high school, she kind of was like, whoa, now I've done this. Now I need to get my first job and I got my first job and I gotta stop picking out college and I picked a college and I gotta do the next, the next best thing, the next best thing. And at some point I had to tell her like, slow down. It's okay. It's, life is not a checklist. You can enjoy the successes. Take your time. There's no rush to do anything. And um, she's a young married couple. I've got a wonderful son-in-law, Jesse, they're a great couple together. They were like, oh, automatically now the next thing we have to do is buy a house.

• 26:32Speaker 06

  And I was like, well, we had to have that talk. You're not necessarily ready for a house just because you think that's the next adult thing that you're supposed to do to kind of check that box. Doesn't necessarily mean that's what comes next. And I had to like slow her down and help her really like live in the moment and enjoy it instead of just going on to the next thing.

• 26:51Speaker 05

  Just real quick, I, I don't think you should question Jesse so much, Carol Anne. I just, nah, just you had, yeah, I was following your story just fine. And then, yeah, you lost me there.

• 27:01Speaker 06

  Don't ever underestimate a Jesse. They know what they're talking about.

• 27:04Speaker 00

  We've learned that the hard way here at Stack Your Benjamins too. Underestimating Jesse a couple of times. Guys, let's do a little game called the Optimization Olympics. You're going to choose, is this worth it? Is the optimization worth it? Is it good enough or should you stop? All right. Let's take turns until we get Maya back, we will just go back and forth. Jesse, we'll start with you. Drive 15 minutes to a gas station where the gas is eight cents cheaper.

• 27:31Speaker 05

  I despise this one. I, I despise this one with everything in my being. It's never worth it. It's never worth it unless the gas station has made one of those mistakes where like they accidentally hang up a one instead of a three and it's like a dollar gas instead of $3 gas. The time that you waste and the gas that you waste to get there, never do it.

• 27:50Speaker 00

  Let's see if that's the difference between a seven and a 10 optimizer. Carol Anne is the 10, eight cents cheaper, 15 minutes out of your way. You going?

• 28:00Speaker 06

  I gotta say no for the amount of time and money that you're spending in gas to get to that gas station. I'm not doing that.

• 28:06Speaker 00

  All right, Carol Anne, let's change it then. Let's say that you've got two gas stations along the same route and both are on your way. You optimizing for the one that's eight cents cheaper?

• 28:17Speaker 06

  Oh, yeah, absolutely.

• 28:18Speaker 00

  Jesse?

• 28:19Speaker 05

  Probably not paying attention to it is my honest answer.

• 28:22Speaker 00

  Not paying attention? That sounds like an OG answer, by the way.

• 28:27Speaker 05

  Not for gas prices. I just think gas is that commodity that is so similar from station to station that, you know, I just, I probably wouldn't notice.

• 28:36Speaker 00

  I'm on the Carol Anne end of this. Doug?

• 28:39Speaker 04

  If I see gas is cheaper across the street, but it means I have to take two lefts and a right to get there, I'm still not going to get the cheaper gas.

• 28:48Speaker 00

  Go.

• 28:49Speaker 04

  They have to be giving out free tasty freezes over there before I make my way to the cheaper gas.

• 28:54Speaker 00

  Let's go to the next one. Open another credit card for a $500 signing bonus. Jesse?

• 29:02Speaker 05

  Um, probably worth it. I have to admit, I don't do a lot of the credit card game. And, and because usually I find, Joe, there's some strings attached. But if it's just like, hey, open this credit card, we give you 500 bucks. And three months from now, you can close it again. I would certainly consider it. And, and that sounds like pretty easy, free money.

• 29:21Speaker 00

  Okay. Carol Anne?

• 29:23Speaker 06

  I struggle with the, the whole credit card hacking thing. I feel like it's a waste on me. So no, I don't do that. I, well, you know why? Cause in the past I've done these things where I've opened a credit card, but I don't spend enough money to really take advantage of points and stuff on credit cards. And there's always strings attached. You have to spend X amount of money in the first six months that you open the card or things like that. And I don't know, I don't benefit from those things.

• 29:46Speaker 00

  You and I are direct opposites because I don't do it because of the fact that I would open it and I wouldn't get rid of it. I would start using it and next thing you know, it's a, it's a bad deal. I had to rein that in when I was getting my financial act together. Maya, $500 you're offered for a new credit card. Would you, would you do it or not?

• 30:05Speaker 07

  No, I side with Carol Anne on this one. Unless it was significant amount of money, but a hundred dollars or $500 right now is not enough to motivate me. Maybe years ago, but not now.

• 30:17Speaker 00

  Let's do another one. Uh, you've got $20,000 in savings. We'll stick with you, Maya. And you are offered at another bank, uh, 0.2% more. So two tenths of 1% more. Do you take it for a 0.2 difference?

• 30:36Speaker 07

  If it's one of those offers where, you know, that only applies for the next three months or six months, it's a no for me.

• 30:45Speaker 00

  Okay.

• 30:46Speaker 07

  It's too much work. I guess I'd have to calculate exactly, you know, I'm trying to do calculations in my head right now, but if it's only for three months or something like that, then definitely.

• 30:55Speaker 00

  Gotcha. So bonus offer, no, but if they're consistently point two higher, you'd do it?

• 31:01Speaker 07

  Yeah, I do.

• 31:01Speaker 00

  Yeah. Carol Anne?

• 31:03Speaker 06

  Yeah, I've opened accounts at different banks, not my main bank though. I've never changed my main bank because it is too much trouble to change your auto, your mortgage payments and all that kind of stuff coming out of the banks. I'm not going to put that much work into it if it's only for like 0.2%. But I have done in my brokerage account, CD ladders, just to get that little tiny bit of optimization, even though it was more work to have to make sure I re-upped every three months or six months or nine months, depending on the term of the CD. I have done that, which may or may not be worth the time.

• 31:37Speaker 00

  Calculating the, the time benefit. It's like hypothetically, maybe driving behind a semi to get just a little bit more mileage.

• 31:45Speaker 06

  Who's crazy enough to do that?

• 31:46Speaker 00

  Jesse, how about you?

• 31:47Speaker 05

  I know. Man, ridiculous things people do to save money. Uh, Maya, I had the benefit of, you know, I pulled up a calculator. I calculated it's a $40 a year difference in the interest rate there.

• 31:58Speaker 00

  There it is, Maya. Forty bucks.

• 31:59Speaker 05

  0.2% on 20 grand was 40 bucks a year difference. I would not make that particular change. That, that feels like over optimization to me. Unless I had some sort of ulterior motive to be like, this bank sucks. They, they've screwed me over one reason or another, something I just don't like. Their, their online portal stinks. The new bank I'm going to seems really, really slick. Like, okay, maybe then I'd change, but not.

• 32:22Speaker 00

  You're going to look at surrounding features.

• 32:23Speaker 05

  Correct, correct. It's other factors would weigh in my decision.

• 32:27Speaker 00

  All right. Let's stick with you for one more here. I like this one. Let's not make it $40, make it $112. You can save $112 instead of flying direct to take a connecting flight, but it adds four hours.

• 32:42Speaker 05

  Okay. Slightly longer answer than it needs to be, but certainly not an OG answer. In today's modern age, you can sit at an airport for hours. And, and in the pre, in 30 years ago, you're like wasting your time. But today, so much work occurs like on a laptop that I could probably be really, really productive sitting there for that four hour layover, like totally wasting my time. But I still don't think I would do it. It would have to be a much, much, much bigger dollar amount for me to accept that. Cause if I could be home four hours earlier and in my own environment, hanging out with the family, that there's no way I'd do that for $112 to set.

• 33:16Speaker 00

  You're valuing the time more than the money. There it is. Maya?

• 33:20Speaker 07

  Yeah, I side with Jesse on that one for sure. I definitely value my time more than the money and it's not enough. I feel like it'd have to be a larger amount of money and I'd rather be home with my kids, get home sooner or wherever I'm going.

• 33:33Speaker 00

  I was going to ask you, Maya, if you had said, yes, I'd do it. I'd say, but you're traveling with two kids.

• 33:40Speaker 07

  No, then especially not. It would have to be significantly larger amount of money.

• 33:44Speaker 00

  It is different if I'm doing it myself, because I've taken this deal before where I have plenty of work that I have to do anyway, and I'm traveling to a place. It's also different if I'm traveling to the place versus coming home. Yes. If I'm coming home, I want the direct flight.

• 33:55Speaker 04

  Yeah. Joe, when my kids were young, I would find overnight layovers just to delay getting home.

• 34:03Speaker 00

  Carol Anne?

• 34:04Speaker 06

  There was a time in my life when I would have said yes to this question, but I gotta give credit to my husband. I, we don't do that anymore. We don't have to. First of all, we don't have to live that way anymore. We don't have to optimize for every single thing. Kevin's much better at this than I am. So, so he keeps me, he keeps me, he's the fun and I'm the money. He's, he figures out how, what we want to do to have fun. And I figure out how we're going to pay for it and stuff like that. But, um, no, I don't do those kinds of things anymore because we can afford the extra $112 not to have to wait three hours in a, in an airport someplace for a layover.

• 34:37Speaker 00

  You call him the fun. He's very fun, but I think you're fun too.

• 34:40Speaker 06

  Oh, thanks, Joe.

• 34:41Speaker 00

  Even though you're the money and keep dragging him to the Boston Benjamin's After Dark groups. So that he becomes the money too. All right. In the second half, we're going to ask you questions that are a lot more serious. We're going to bring it with some of the bigger questions, which are five more year syndrome for people that are maybe hanging on to work for too long, just to optimize their money situation. That one. And then we're going to give a money test for people that have kids, teaching your kids about money. And I'll be curious to hear what all of you have to say, because you all, all three of our participants have kids, but we'll get Maya's take on that one. But halfway through our episodes on Friday, we have this phenomenal year-long competition

• 35:23Speaker 00

  between our three frequent contributors, Jesse, who's here, OG, who is now being played by Carol Anne, and then Paula Pant, who is being played by Maya. Maya, you want the good news or the bad news about how this is going to go?

• 35:42Speaker 07

  Let's do the bad news first.

• 35:43Speaker 00

  Well, the bad news for you is the good news for Carol Anne, because Paula is in last place. That's the bad news for you. That's the good news for Carol Anne. But that also Maya means there's some good news for you because Paula's in last place. You get to guess last. Carol Anne, that's the bad news for you because OG's in first place. You have to guess first. And Jesse, no news is good news for you because, uh, you're in the middle, buddy. What's the score, Doug, so far this year?

• 36:14Speaker 04

  Well, last week Paula made it really, really interesting and fun by scoring a point all by herself. So she's up to seven points now. That leaves Jesse as the forgotten middle child. He's at eight points and OG is in the lead, but not by much at 10 points.

• 36:32Speaker 00

  Seven, eight and 10. It is fairly close. So let's see if it's going to get closer or if we're going to break it apart. Doug, what's today's question?

• 36:45Speaker 04

  Hey there, stackers. I'm Joe's mom's neighbor Doug. And it was on today's date back in 1964 that an incident known as the Great Plymouth Truck Robbery occurred. Seriously, it was nearly as big as Joe's mom's ATM incident of '09 that we aren't allowed to talk about. But I just did. Ah, I did it again.

• 37:05Speaker 00

  There you go.

• 37:06Speaker 04

  Okay. Anywho, two men dressed as police officers stopped a US mail truck delivering small bills from Cape Cod to the Federal Reserve Bank in Boston. They tied up the driver and the guard and drove off, stopping to drop off money in various places. The truck and its two tied up occupants were later abandoned. This was the biggest cash heist ever. It was huge at the time. So let's ask this question. Just how big was it? How much money in small bills did these bandits make off with? I'll be back right after I see if I can heist a few of the chocolate chip cookies I hear coming out of the oven upstairs. Listen, folks, if you've got the phone number for Joe's mom's house, call her right now because I need a distraction.

• 37:51Speaker 00

  I can't wait to hear the phone calls upstairs. While we're waiting for those, Carol Anne, that's actually close to home for you.

• 38:00Speaker 06

  It really is.

• 38:00Speaker 00

  It was a long, long time ago, long, long time ago, but maybe you know some of the, the history of the area. How much money was stolen?

• 38:10Speaker 06

  Did David Doug say what year this was?

• 38:14Speaker 04

  I did. It was 1964.

• 38:16Speaker 06

  Thank you. Okay. I don't know the answer to this question. I feel like I should because I think they made a movie out of it.

• 38:24Speaker 00

  I don't know. You're, you talk about the one with Ben Affleck?

• 38:27Speaker 06

  Yeah.

• 38:28Speaker 00

  That was where they held something up. I don't know if that's the-

• 38:30Speaker 04

  The town? Are you talking about the town?

• 38:32Speaker 06

  I don't know if it was the same. It doesn't help me to answer the question anyway. So at this point, I'm just stalling for no good reason.

• 38:39Speaker 04

  It was not about this.

• 38:40Speaker 06

  So 1964, there was a lot of money. It's obviously gonna be, I don't know. I'm gonna go with, um, $10 million.

• 38:48Speaker 00

  $10 million. Jesse, what are you gonna do with that number?

• 38:55Speaker 05

  A good guess, Carol Anne, interesting guess. I liked how the movie angle helped you answer the question in the form and fashion of OG, you know, telling a story, weaving in outside details. That was very well done.

• 39:11Speaker 04

  And this really did almost happen in her hometown, as OG often claims.

• 39:16Speaker 05

  Correct, correct.

• 39:18Speaker 06

  Listen, Kevin's not gonna be happy when I get home tonight, I can tell you that.

• 39:23Speaker 05

  I'm gonna go lower and, uh, is a million, is that too high or too low? I'll go with a million. I'll go with 1 million even.

• 39:33Speaker 00

  1 million. So much, much, much lower. So Maya, you've got 10 million from Carol Anne, a million from Jesse. What are you thinking?

• 39:43Speaker 07

  I was originally gonna go with a million, but since Jesse picked that number, I was also thinking, how far is Cape Cod from Boston? Because they were stopping and distributing all this money or hiding it along the way. So I thought, okay, does that have anything to do with anything? It really doesn't. I mean, they could have put away as much money or as little money along the way.

• 40:05Speaker 05

  Could have been $10 here, $10 there, right?

• 40:06Speaker 07

  I'm just gonna go, yeah. I mean, really. So I'm gonna go with 5 million. It's completely unrelated, but just kinda-

• 40:14Speaker 00

  So split the difference. All right. We got Carol Anne at 10 million, Jesse at 1 million, Maya halfway, well, almost halfway between them at 5 million. Who's gonna take this home? We're gonna find out in a minute. We'll be right back. Well, you may know the chaos is the name of the game here in mom's basement, what with guests coming in and out, Cooper the cat getting in the way, Doug being, well, being Doug. The holidays make it even worse because it's all about food and big meals. And the problem is, prepping for those takes forever. But what about those between meals, right? The meals between those huge, huge bookends? Well, that's where Factor comes in. Factor is made with high quality ingredients

• 40:57Speaker 00

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• 41:42Speaker 00

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• 42:24Speaker 00

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• 43:08Speaker 00

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• 45:39Speaker 00

  All right, Carol Anne, you started at 10 million and, uh, these two thought that maybe that was a little high, but listen, if it was 50 million, you're gonna bring this home. Feeling good?

• 45:49Speaker 06

  Feeling good about my answer, Joe.

• 45:51Speaker 00

  Excellent. Jesse, you got the lowball answer at a million. It was 1964, so it could have been, you know, what's a million then versus a million today?

• 46:02Speaker 05

  Right, exactly. I don't really have a good feel for how much these trucks have in them. I mean, even today, if you ask me, how much does that truck going by on the highway have in it? I have no idea. Uh, so anyway, I'm pretty flustered on this one.

• 46:14Speaker 00

  Find out one time.

• 46:17Speaker 00

  While you're tailing it, while you're tailing it down the freeway.

• 46:22Speaker 00

  That might not end well. Uh, Maya, you're right in the middle at five. So you've got like from what, 3 million to 7 ish? Feeling good?

• 46:32Speaker 07

  Yeah, I think so.

• 46:34Speaker 00

  All right. Maya thinks she's bringing it home, but only one person knows who's taking this home. Is Maya helping Paula get back into a tie with Jesse? Is Carol Anne helping OG pull ahead again, like he was earlier in the year? Or is Jesse creeping up right behind OG? Man, I can't wait to find out. Doug?

• 46:58Speaker 04

  Hey there, stackers. I'm chocolate chip appreciator and guy who needs better henchmen, Joe's mom's neighbor Doug. Nobody called. You know, good work usually boils down to having a good team. And I gotta say, phone didn't ring, stackers. So when I say my hand was caught in the cookie jar, it's not a euphemism. She literally caught me with my hand in the cookie jar. Like, it was all the way up to the elbow, it was all the way in there. Well, unlike me, back in 1964, some bandits got away with a ton of cash. Most of the money was never recovered. And while some people were indicted, most fear that the true criminals may have gotten away. That Carol Ann knows who they are. But how much money did they get away with? Well, it was eight and a half million less than

• 47:42Speaker 04

  what Carol Ann guessed, three and a half million less than what Maya guessed, just 500,000 more than what Jesse guessed, because the correct answer is $1.5 million, making Jesse our winner, who is now just one point out of the tie for the lead.

• 47:58Speaker 00

  Jesse Cramer with the big win.

• 48:00Speaker 05

  I'm drafting OG. That's what it is. I'm drafting him. I'm gonna say like, one point behind him right until the end.

• 48:07Speaker 00

  You kind of figured out that if you draft him all season, like, that's optimizing this whole stacking Benjamins thing.

• 48:12Speaker 05

  That's the goal. That's the goal. Yeah. I'm sorry for taking the 1 million guess before you got to it. That's my bad.

• 48:20Speaker 00

  You would think going last would be a benefit, but Paula goes last every week.

• 48:25Speaker 04

  If she'd only said a million and $1.

• 48:28Speaker 00

  A million and one. Yeah.

• 48:30Speaker 06

  It's like Price is Right.

• 48:32Speaker 00

  Yeah, that's what when she first said, well, my first guess was a million, I thought she was going a million one. I thought, oh, maybe, maybe she's doing it. All right. Let's get back to the real questions, because we're talking about optimization. Let's start off with kids and a conundrum with kids, and then let's talk about one for adults. All right, your 12-year-old has saved $200. They want $150 sneakers. It's their money. Is it worth it? Is it good enough? They should do it? Or do you stop it? Let's have Maya answer last. Jesse, you've got kids too young for this so far. So put your dad hat on. What are you thinking?

• 49:10Speaker 05

  My first instinct is to let them spend that money the way they want to. And then, I mean, right, as long as it's not like truly harming them, you know, but like, right, I think spending money on shoes is a perfectly reasonable way to spend money. And then, there's always that lesson, if there even needs to be a lesson, maybe they love the shoes, and it's the best thing they've ever spent money on. Or maybe there's an opportunity down the line to be like, oh, you see, like, you know, when you spend money, sometimes you don't exactly get the fulfillment that you thought you would. And it's an interesting lesson to carry forward. But I don't see any issue with it.

• 49:42Speaker 00

  Carol Ann, I'm sure you've been through this before.

• 49:44Speaker 05

  Issue buying the shoes. Sorry.

• 49:46Speaker 00

  Issue. Oh, just a

• 49:48Speaker 05

  Not an issue me.

• 49:48Speaker 00

  Hold on, hold on. There it is. Yeah. Carol Ann, you maybe have been through this before.

• 49:55Speaker 06

  Yes, I'm actually in agreement with Jesse on this one. If they put their mind on something, they saved up for it, they worked for it, let them buy it, it's not harmful to them. I'm hoping that they do see that once they have $200 sneakers on their feet, it's not all it's cracked up to be. And maybe that's the first and last time they do that. But you can't teach that kind of lesson. I think people have to spend their money and waste it sometimes to learn that. I'm in agreement with Jesse on that. I'm buying the shoes.

• 50:21Speaker 00

  Okay, sometimes even if it's a bad decision, might be the right decision. What does our kids and money expert say, Maya?

• 50:27Speaker 07

  Yeah, I agree with both Carol Ann and Jesse. One thing that I frequently talk with parents about is about letting kids make their own mistakes. Personal finance is called personal for a reason. And so, as long as we're responsible in terms of, you know, we save, we invest, we pay our bills, the rest of the money should be used to give us some fulfillment and joy, in my opinion. And a lot of times, I like to use an example of, you know, how there are some things that I like to spend my money on that my teenage son would find very wasteful. Some things that give me joy are like my manicures. To him, that's obviously ridiculous, but he likes spending money on video games. And as Carol Ann said, these are the lessons that they can only learn by spending that money.

• 51:11Speaker 07

  And maybe they will have, they will enjoy those sneakers and have the best time ever wearing them. Or maybe they will be like, well, this really wasn't worth the money. I could have done something better with it.

• 51:21Speaker 00

  It sounds like it takes some strength. I mean, you really got to circle back a few weeks later and have a conversation.

• 51:26Speaker 07

  Yes, absolutely. And I always suggest that. And I've done that with my own kids. I remember sometimes the hardest lesson, or hardest thing for parents to do is to watch their kids spend the money on silly things. They're silly to us, but they're meaningful to the kids. And so I've done that with my own children. And I would always follow up a week or so later and gently ask, hey, how was that? Would you do that again? Would you recommend that purchase to your friend? And kids know, they know when they've made a mistake. They know when they should have done something different. Or once in a while, they're like, no, this was really great. I would do it again.

• 51:59Speaker 00

  That's great, guys. Let's go to adults. We see this one all the time, especially in personal finance. Carol Ann, you're financially ready to retire, let's say. But given another five years, you would have a much larger safety margin. Is it worth it, going another five years at work, when you're ready to go? And you're shaking your head, no.

• 52:19Speaker 06

  I'm shaking my head because I'm actually struggling with this right now.

• 52:23Speaker 00

  Oh.

• 52:23Speaker 06

  Yeah, this is a very timely question for me. My husband retired two years ago. And I have a ways to go before I can or planned on retiring. But every time I look at the numbers, they seem to work. But yet, I'm still hesitant to pull that trigger and leave. Like, I originally planned on working till 65, and that's a long time from now. And he's already retired, and I'm missing out on time that we could be spending together and like, waiting to do the things that we're putting off until retirement, some of the bigger things. And so, I'm really having a hard time with the two more year thing.

• 53:03Speaker 00

  Do you enjoy what you do?

• 53:05Speaker 06

  I do. I enjoy what I do. And I do feel like I've got some goals, professional goals, that I still want to meet. And I'm capable of meeting, and I see no reason why I can't meet them within the next two to five years. And that's great. But like I said earlier, I'm also looking at people my age and realizing that we might not have as much time or health as we think that we do. And so, how much Russian roulette do you really want to play with the time that you've got left? Because, God forbid, here I could get sick, and maybe that decision is made for us, and it doesn't work out the way that we want it to work out. Yeah. So yeah, I'm kind of teetering on that right now. Every time somebody asks me when I'm going to retire, I keep saying, it's either going to be somewhere between two and nine years, which is a ridiculous time span. I

• 53:49Speaker 06

  just, but I can't figure it out. I don't know what to do.

• 53:52Speaker 00

  Give it between one and 100 years for now. But it's interesting. I'm wondering if there's a, I mean, this is a topic for another day, but for a lot of people, maybe there's a halfway on this. Maybe there's a, maybe there's a, there's a mid-ground. Maya, what about for you? Let's say you've got enough money to retire, but stay in a couple more years would really help and give you a margin of safety.

• 54:14Speaker 07

  So, you know, it's really interesting, because I'm kind of thinking about that as well. It is a timely question for me and my husband as well. Our kids are older. Our son is in university right now. The daughter will be going next year. We're at that point now where we could retire. We could downsize. And I feel like, as Carol Ann said, you know, I'm doing the calculations, there seemed to be, there would be enough money. But I've also created, luckily, I was lucky, and I created a life that I love, and I enjoy what I do. And part of me always thought I was going to work forever, because I like what I do. But I also realized that sometimes I get, I guess, a little bit too obsessed,

• 54:57Speaker 07

  or maybe I'm a little bit of a workaholic. So I tend to forget to have fun. And my husband is also the fun one as well. And the older I get, and as the kids are getting older too, I realize like what Carol Ann is saying, our health, you know, we have it now, we're capable, we can travel, we can do things that maybe as we get older, we may not be able to. So I think it's about trying to find that balance, and maybe retiring part time, maybe not retiring full time.

• 55:25Speaker 00

  Let's go to the pro last. You know what I find fascinating about both Carol Ann and Maya's answers, Jesse, is that, you know, we're kind of, we're gonna be talking about this a lot in the fall on the show, kind of questioning the whole premise of this full retirement. What's it all about? Where's the boundaries? It seems to be less about the money for both Maya and Carol Ann.

• 55:45Speaker 05

  Yes. I loved both answers. I find this topic endlessly fascinating. Isn't it interesting? Right. So the answers had to do, both your answers had to do with time, had to do with children, had to do with travel. It didn't have to do with the optimization of the numbers themselves. And I forget if this episode is even out or not. But either way, recently, I was speaking into a microphone for my podcast, and I talked about the idea of, let's stop thinking about it as one more year syndrome. One more year of income, one more year of compound interest, so that it can feel safer. And let's got to flip it on its head and think about one less year syndrome. So, right, it's, it's a one less year of time where you'd get to really spend a lot of time with your children. It's one less year where you're going to be healthy enough to do things like travel and be an active retiree. And if you

• 56:30Speaker 05

  think about the pot of available years that you have to spend time with your kids or be active in retirement, it might not be nearly as big as you think. And to take away one of those years to say, I'm going to keep on working, you are taking away a very limited resource in terms of that viable time that you have to pursue your passions and life goals. And so that doesn't mean that people need to dive into retirement headfirst when they financially ought not to. But I think what it does mean is that once your numbers say that you're good enough, you really need to pivot into thinking about what you are sacrificing by staying at work for more and more years, if work's not the thing that really fulfills you, and if your goals lie elsewhere.

• 57:09Speaker 00

  I think that fulfillment part's so important, because what I didn't like about the way you framed that, Jesse, was around, what are you sacrificing by staying at work? And I did like what Carol Ann said, where she's like, I got some professional goals. And I think sometimes you might leave work and go, you know, I left some things on the table that I really wanted to get done, if I'm pretty passionate about what I do. I think that may be a big piece of the key. Let's stick with you for a second. Let's talk about optimization, where we see it a lot as financial nerds. Investments, Jesse, do you think that optimizing your investments can actually make you a worse investor? Where's that line?

• 57:48Speaker 05

  Yeah. One of the data points that I really like to point to, although it does have some people who criticize it, but I think this particular data point is referred to in a positive manner, much more than it's referred to in a negative manner, comes from John Bogle, and it's research from like the late 80s or early 1990s. And it basically says that your broad asset allocation leads to something like 90% of your overall investment returns, meaning your choice of investing 70% in stocks versus 30% in bonds, that's the broad asset allocation, is so much more impactful than which stocks you actually invest in, which would be like the micro asset allocation. So when we talk about investment optimization,

• 58:30Speaker 05

  it often is people really diving into that nitty gritty nuance about which stocks and should I invest in TIPS or treasuries? Should I invest in municipal bonds in my taxable account to prevent the tax bill? And it's not that these questions are bad. It's fine to try to squeeze some juice out of that final 10%, but I think it is important. I think some people lose the, they lose sight of the forest for the trees, or whatever it might be. And they forget the fact that the biggest decision they can make is that broad asset allocation decision. And everything after that, it just, you're really getting a lot less bang for your buck for the time that you're spending there.

• 59:03Speaker 00

  So you're saying studying and learning asset allocation better could be a great use of time, but picking individual stocks, maybe not?

• 59:12Speaker 05

  Correct.

• 59:13Speaker 00

  Yes. And yet, Maya, I saw a tweet, do we still call them tweets? I saw a tweet recently from Elon Musk saying, all these people betting against SpaceX, they are selling short SpaceX shares, that they are in trouble because if you've bet against him in the past, it's been a losing proposition. And he said, you know what, SpaceX is going to go up? It's going to go up big? And I read that and I'm like, oh, maybe I should put some money in SpaceX. I don't know. I feel like there's always a quicker, better, funner stock that I could own.

• 59:46Speaker 07

  Yeah, I find that a lot of times, like, there is that FOMO. And with FOMO,

• 59:53Speaker 07

  oh no.

• 59:53Speaker 00

  And we lost her again. Maya's had so much fun with her internet today. I've been where she's, she's at before. We'll go to you, Carol Anne. Are there times when you think that you just, if I take her with it a little more, like, maybe it'll get a little better?

• 1:00:08Speaker 06

  You know, when it comes to that kind of stuff, no, because, so I'm like an index fund kind of investor. I just want a piece of everything. To me, when you get to the point of what you're asking about right now, Joe, it feels like you're gambling. And my money is too hard come to me. And I've worked too hard to get my portfolio where it is to really gamble. So I don't want to be like trying to optimize in one area, SpaceX is an example. You might be losing out on something else. But if you just kind of go in with ETFs or index funds or things like that, you get a little bit of everything. I feel like I'm hedging my bet in multiple ways as opposed to individual stocks. And fear of missing

• 1:00:49Speaker 06

  out is not an issue for me because just like I could go up, I could go down. And I just don't want to risk it.

• 1:00:57Speaker 00

  I love that quote that my money's too important to me to bet. That is the direct opposite thinking of so many people. And I absolutely love it. I want to ask you one more thing. Let's talk about optimization outside of money. You know, you see some people that are really optimizing productivity, optimizing their health a lot. Is there a time, Carol Anne, you find that maybe optimizing productivity or optimizing health can make you less productive or less healthy?

• 1:01:22Speaker 06

  I always feel like your health is your number one priority. And if you're spending any money on your health, vitamins, medicine, gym, wellness programs, whatever it is, that's an investment in the larger picture. I suppose you can get a little obsessive about it. A third glass of wine isn't going to necessarily take 10 years off your life. You can become obsessed by it. I have been that person at certain times in my life where I've looked at the steps on my watch and took another walk around the house before I went to bed just because that's a little cuckoo. I don't need to be doing things like that. It's not gonna, it's not gonna move the needle all that much. But I do think overall, in the bigger picture of things, optimizing health should be a number one priority. Because what good is the money for if you don't have the health and the lifespan? And not so much

• 1:02:07Speaker 06

  lifespan, but the health span to be able to spend it and enjoy it and do all the things.

• 1:02:12Speaker 00

  So Carol Anne, I want to clarify something. So three glasses of wine, like, where's the line? Like, where do I need to get worried? Is it that ninth glass? The third bottle? Just for clarification, for a friend.

• 1:02:24Speaker 06

  When you, when you go from glasses to bottles, as far as a measurement goes, you might want to think about the line being somewhere in there.

• 1:02:30Speaker 00

  Is that, is that when I kind of check my?

• 1:02:31Speaker 06

  Yeah, that's what I'm taking from that.

• 1:02:33Speaker 00

  I'll let, I'll let my friend know. When you're measuring in bottles, that's awesome. You know what's interesting to me is that when I see people that spend so much time at the gym, that it ruins other pieces of their life, like their, they don't see their family as much, same thing as work. And I know people like this, that spend so much time. By the way, Carol Anne, to your point, yesterday Cheryl and I went for a walk and we were one tenth of a mile away from the next mile marker. So she went and walked a little bit down the street and back to get that last tenth of a mile, same thing. Jesse, productivity, can optimizing productivity make you less productive?

• 1:03:08Speaker 05

  Probably. And I think even, what's the, um, there's some famous, like, business school type guy, Hutchinson or something like that. And he's got this law that says, you know, work kind of expands or contracts to fill the time allotted to it. I find that to be true in my life. So I guess what I'm saying is like, optimizations hacks haven't always worked. And what really it comes down to is if I'm working to a deadline, I somehow managed to get it done. And if I sit down at my computer and I'm like, oh, I've got a wide open day. I don't really have anything I need to do. What will I do today? I tend towards dilly-dallying and not being very efficient. And maybe that could very well just be a Jesse problem. My point is that these optimization productivity hacks don't

• 1:03:53Speaker 05

  always seem to work for me, or I've just had a very mixed bag of reviews. And it just leads me to the conclusion that maybe it's just less about the hack and more about some other factors.

• 1:04:03Speaker 00

  Maya, based on what Jesse said, I want to end on this question. Do you ever feel like there's a time when this obsession with over-optimization really is just procrastination in disguise? And maybe we should recognize it as such?

• 1:04:16Speaker 07

  100%. I think you nailed the problem here. In my line of work, there are a lot of parents that want to start investing for themselves and their kids. And so many of them watch financial literacy content online, or they listen to podcasts, and they analyze things. And yet, I get so many messages on Instagram from parents saying, hey, I've followed you for so many years, but I still haven't opened that investment account. And I'm not sure if I should invest in this or that. And it's like, how about we just open that account? And we find a nominal amount of money that you invest that lets you sleep at night. It could be $50. You can buy fractional shares. Let's just get to move on, rather

• 1:04:58Speaker 07

  than optimizing for all this, you know, what to invest in, what account is better for me in terms of my financial situation and taxes and everything else.

• 1:05:07Speaker 00

  I love this so much. On our Financial Action Month here at Stacking Benjamins, such a great thing. Just get started. All right, we're going to wrap it up there. I've got 87 more questions, but we're going to call it a day. I love the idea of optimizing. But when I hear about getting behind a, getting behind a semi, to draft the semi, maybe there's too much. That makes me laugh nearly as much as I did when I heard about the three glasses of wine, just totally wrecking a podcaster's week. Like, really? What about that time with friends? Is that, are there times when times of friends might be worth the third glass of wine? I don't know. Let's find out what's happening where you all are. So Carol Anne, let's have you go first. Next Wednesday night, let's do the details again, 6:30. If you're

• 1:05:50Speaker 00

  in anywhere in New England, come out and visit. You guys, where are you going to be?

• 1:05:54Speaker 06

  Come on down to Melrose. We're at Hannah's Brewing Company on Main Street in Melrose. And it's the third Wednesday of every month, 6:30 PM. So next week.

• 1:06:04Speaker 00

  And if you go to stackingbenjamins.com/bad, B-A-D, you'll find our Benjamin's After Dark groups across the country. Thanks, Carol Anne, who I'm not even going to mispronounce her last name again. Embarrassing. I've known Carol Anne, maybe for what, 10 years, maybe?

• 1:06:18Speaker 06

  And every time you say it, you get it wrong. It's extraordinary.

• 1:06:21Speaker 00

  I know. I'm wicked smut at pronouncing it horribly bad. Did I get that accent right?

• 1:06:26Speaker 06

  That was good. Yep.

• 1:06:27Speaker 00

  I'm coming close. Maya, thanks for hanging out with us. It's so good to have you. We were talking about how we've been in internet jail before, and everybody feels super bad when, there's days it just isn't, isn't working. But I'm so glad you could share your wisdom with us. So tell us what's going on with you. What's coming up next?

• 1:06:46Speaker 07

  Right now, the Wealthy Kids Investment Club is open for enrollment. And I'm also taking on any opportunities for speaking engagements at the schools, or events and conferences and things like that.

• 1:06:59Speaker 00

  People can go to wealthykids.club, right? It's wealthykids.club. You know, if you're a kid or a kid at heart, right?

• 1:07:06Speaker 07

  That's correct.

• 1:07:07Speaker 00

  Jesse Cramer, tell us what's coming up at the Personal Investing for Personal Finance for Long Term Investors podcast. I can't, I can't get Carol Anne's name right. I can't get your podcast name right.

• 1:07:21Speaker 05

  Well, I mean, Carol Anne's last name, I think it's five syllables.

• 1:07:26Speaker 06

  Well, it's a long name.

• 1:07:27Speaker 05

  Is that right, Carol Anne?

• 1:07:28Speaker 06

  Yeah.

• 1:07:28Speaker 05

  Desa Dario?

• 1:07:30Speaker 06

  Dario, yeah.

• 1:07:30Speaker 05

  Yeah. I mean, my podcast title is, I think, 48 syllables. So it's a different magnitude there, different scale factor. I ran out of fingers. Nevertheless, we still create podcast episodes even with all the syllables. And this past Wednesday, we published an episode, is my DIY financial plan working?

• 1:07:50Speaker 00

  Oh, cool.

• 1:07:51Speaker 05

  Just kind of a deep dive into, oh, I think we all know the importance of having a good financial plan. But I would posit that there are plenty of people out there who don't exactly know what a financial plan is. I don't think our industry has done a very good job of even defining what that term means. So we talk about that. And then we help listeners understand if their financial plan is kind of working or not, and what some of the telltale signs are that it's good or bad or somewhere in between.

• 1:08:13Speaker 00

  It's always interesting when I see somebody who's like, I think I'm going to fire my financial planner because the S and P 500 is fine. And I'm like, you have no idea what a financial plan is or what a financial planner does. And if your financial planner is somebody that just competes against the S and P 500, it's time to fire them anyway.

• 1:08:29Speaker 05

  I think that's very well said, well said.

• 1:08:32Speaker 00

  We will link to Wealthy Kids Investment Club, we'll link to the Benjamins After Dark meetup in Boston and elsewhere around the country and a personal finance for whoever podcast, personal finance for long-term investors on our show notes page at stackingbenjamins.com. All right, Doug, you've got it from here, man. What should we have learned on today's show?

• 1:08:53Speaker 04

  Well, Joe first takes some advice from our guest panelist, Maya Corbic. It's possible to over budget. Dude, chill out a little. Make sure you don't lose sight of the fact that a big part of the goal is happiness. Second, remember what Carol Ann said about optimizing your career. If you enjoy what you do and you still have goals you want to achieve, maybe it's okay to work a few more years than you absolutely need to.

• 1:09:17Speaker 00

  Wait a minute, what?

• 1:09:18Speaker 04

  But the big lesson?

• 1:09:21Speaker 04

  If you're planning the great cookie iced of the 2000s, it's better to formulate a game plan ahead of time. Otherwise, you'll be doing time washing windows all weekend, which wouldn't have happened if you were all better at creating diversions. Maybe we'll practice again next week, team.

• 1:09:38Speaker 04

  Thanks to Carol Ann Desperado for joining us. If you're in the Boston area, you can meet Carol Ann, James, Sue, and our great stackers who meet up every month at our Benjamins After Dark meetings. Heck, if you're in other cities, you can also meet up. Head to stackingbenjamins.com/bad for details about our meetup groups so you can hang out with people nearly as cool as Carol Ann. Thanks to Maya Korbic for joining us today. You'll find Maya's work helping kids learn about money at the Wealthy Kids Investment Club, found at wealthykids.club. We'll link to it in the show notes at stackingbenjamins.com. And finally, thanks also to the Jesse Kramer for gracing us with his presence once again.

• 1:10:21Speaker 04

  Look for his absolutely filthy podcast, Personal Finance for Long-Term Investors, wherever you're listening to us right now. You'll love it. This show is the property of SB Podcast LLC, copyright 2026, and is created by Joe Saul Sehi. You'll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. And oh, yeah, before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. 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

• 1:11:06Speaker 04

  see you next time back here at the Stacking Benjamin Show.