Most people plan their retirement like they control the date. The data says they don’t. A new Society of Actuaries study found that 59% of retirees stopped working earlier than expected — and for most of them, the decision wasn’t theirs. Health setbacks, job loss, caregiving demands, and plain old job dissatisfaction all showed up before the spreadsheet said it was time. Joe and OG dig into what the numbers actually mean, who’s most at risk, and the specific steps that create real flexibility before retirement finds you. OG and Anna follow with a full walkthrough of equity compensation — RSUs, ESPPs, and stock options — including the tax surprise that catches most people off guard.
What You’ll Walk Away With
- Why 59% of retirees left the workforce earlier than they planned — and why only 6% left later
- The income gap nobody talks about: how high earners retire early mostly because they wanted to, while lower earners are pushed out by health and job loss
- Why Coast FIRE math falls apart the moment your income stream stops before you planned — and what that means for how aggressively you should be saving right now
- The one manager change that can end a 20-year career overnight — and why keeping your network warm is one of the most underrated retirement prep moves available
- The 30-year mortgage paid like a 15-year analogy: why building financial margin now means retirement can happen on your terms, not someone else’s
- How to prepare for the emotional side of early retirement — including the identity shift, the relationship changes, and the pent-up demand that makes the first year unexpectedly wild
- RSUs versus stock options versus ESPPs: what each one actually means, how they’re taxed differently, and why getting a grant without a strategy is the most expensive mistake in equity comp
- The 5-10% concentration rule: how much of your net worth should be tied to company stock — and why your paycheck counts in that math
- The RSU tax trap: why your company withholds at 22% but you might actually owe 37% — and why spending all your RSU money on a pool before April is a terrible idea
- Stacker Kiki’s accountability letter: the complete list of what she’s cutting, what she refuses to cut, and why the gamification of frugality is more powerful than white-knuckling it
Why This Matters Now
You may not get to choose your retirement date. But you do get to choose how prepared you are for the day it arrives. The people in this study who retired early by choice had one thing in common: they’d built enough margin that the choice was actually theirs.
From the Basement
Joe and OG dig into a USA Today piece on the surprising frequency of unplanned early retirement — and what to do about it before the decision gets made for you. OG and Anna deliver episode five of their financial basics series with a full equity compensation walkthrough, including the tax withholding gap that sends people to April with surprise bills. Doug arrives with Mickey Mantle trivia. A community poll on how often Stackers check their portfolios during headlines produces results that are more honest than most people expected. Stacker Kiki writes a detailed letter about her intentional spending cuts, and OG quietly admits he’s been burning through hotel shampoo samples all year.
Resources Mentioned
Stacking Benjamins Community — stackingbenjamins.com/basement
Society of Actuaries Retirement Risks Survey — released May 2026; linked at stackingbenjamins.com
USA Today — “Most of Us Retire Earlier Than Planned. Here Are the Top Reasons.” by Daniel DeVise; linked at stackingbenjamins.com
Stacking Benjamins Basics Guide — season one and season two workbooks free at stackingbenjamins.com/basicsguide
Stacking Benjamins Scorecard — stackingbenjamins.com/scorecard
Stacking Benjamins Newsletter (The 201) — stackingbenjamins.com/201; Kevin Bailey’s hot take on this week’s piece
Stacking Benjamins YouTube channel — full OG and Anna equity comp series; youtube.com/stackingbenjamins
Stacking Benjamins BAD Groups — meetups in Boston, Seattle, Twin Cities, Mankato, Tucson, and more; stackingbenjamins.com/bad
Stacking Benjamins Vault — stackingbenjamins.com/vault
Our Headline
Doug’s Trivia
- On this date in 1969, the New York Yankees officially retired uniform number 7. Which legendary switch hitter wore that number?
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Written by: Kevin Bailey
Miss our last show? Listen here: Why High Earners Still Feel Broke (And What to Do About It) SB1851
Episode transcript
[00:00:00] Joe: Welcome to the number one personal finance podcast in Mauritius. Woo-hoo.
[00:00:05] OG: Sweet.
[00:00:05] Joe: To all of our Mauritius fans, both of you, hope you’re having a great day.
[00:00:09] OG: Think it’s people that are listening, or do you think it’s somebody who’s on vacation?
[00:00:13] Joe: I, I doubt it. I think we’re huge in Mauritius. I think we need to- Ah, you’re
[00:00:16] OG: probably right.
[00:00:16] Joe: Yes. How come we don’t have a Benjamins After Dark group in Mauritius?
[00:00:20] OG: Soon to be one,
[00:00:20] Doug: I think. Excellent question. I’m just happy we get to check one of our to-do list items off.
[00:00:27] Joe: W- what do people from Mauritius call themself? Mauritians? Mauritians? I don’t know.
[00:00:33] Doug: Martians?
[00:00:34] Joe: You know what we call this segment, though?
[00:00:36] Joe: We call it the time when we salute our troops. We do this to begin every week here on Stacking Benjamins. So raise your mug, everyone, on behalf of the men and women making podcast in mom’s basement and the men and women who are stacking benjamins around the world, especially in Mauritius. Thanks for all you do.
[00:00:58] Joe: Let’s go stack some benjamins together now, shall we? Cheers.
[00:01:01] Doug: Thanks everybody.
[00:01:02] opener: Ignition sequence start. Six, five, four, three, two, one, zero. All engine running. Liftoff.
[00:01:20] Doug: Live from Joe’s mom’s basement, it’s The Stacking Benjamins Show
[00:01:35] Doug: I’m Joe’s mom’s neighbor, Doug, and do you ever drive along and you see that phrase, “Objects in mirror are closer than they appear”? What if that were your retirement? A new study shows that millions of people retire earlier than they’d planned. Could that happen to you? We’ll share the study’s findings, plus our plan to help you prep on today’s show.
[00:01:56] Doug: Plus, in our Financial Basics segment, OG and Anna are back with another hit segment, what if you have the opportunity to own your company’s stock? They’ve got your go-to guide. And then I’ll share some retirement-themed trivia. And now, two guys who appear larger in person than they do on a podcast, it’s Joe and O, J-J-J-J-G.
[00:02:25] Joe: Hey there, Stackers, and happy Monday to you. We are back. Sit back, relax. You’ve found us. It is the Stacking Benjamins show. We’re super happy to be here. Doug, how’s things going on your side of the card table?
[00:02:37] Doug: Lovely. Things are great over here, Joe. Way, way, way over here on the other side- Way … of the card table.
[00:02:42] Doug: Way, way, way. The weather’s great on this side of the table, birds are singing, children are happy and playing.
[00:02:48] Joe: And the guy who’s way, way on the other side of the triangular card table, Mr. OG, joins us to kick off another great week. How are you, man?
[00:02:56] OG: Uh, very good. Thanks for asking.
[00:02:59] Joe: Well, you know, it-
[00:02:59] OG: How are you, Joe?
[00:03:00] Joe: Well, I am great. But you know what? I’m not somebody who is worried about the fact that I might have to retire early. The numbers on this are far more- Well, we
[00:03:10] OG: have been meaning to talk to you about some things But go on, tell us more.
[00:03:13] Joe: We often don’t think that retirement might be around the corner yet. A recent, uh, USA Today piece talks a lot about that, so we’re gonna dive in, and this will be your go-to guide.
[00:03:23] Joe: If you know somebody who is in that predicament, where they might find retirement thrust upon them, uh, we’re going to dive into what to do there. And Doug, I know you’ve got your best trivia ever waiting.
[00:03:37] Doug: Probably the best one ever, statistically, scientifically.
[00:03:40] Joe: Yes. And then the next, uh, this sounds like the start of a joke, uh, what do you get when you put two CFPs in a room?
[00:03:46] Joe: And it, it, it does sound like the beginning, beginning of some- Sleep
[00:03:49] Doug: apnea.
[00:03:52] Joe: Well, this’ll keep you awake, ’cause it’s actually gonna be really interesting. Anna and, uh, OG going to help those of you… And even if you don’t have stock in your company yet, man, if you change jobs tomorrow and they offer stock, this is all stuff that you’re gonna wanna know ahead of time.
[00:04:08] Joe: All right, everybody get ready to strap in, because we are gonna get this conversation started, but first, it is here, we are super excited, you can try it for free, the Vault. The tools that you use every day, budgeting and net worth tracking, we have a free feature where you can see how the Vault works at a very basic level.
[00:04:31] Joe: Stackingbenjamins.com/vault gets you there. And of course, the real Vault, if you sign up, is a Swiss Army knife. It does things that seven other apps on your phone do to help you control your financial life, from your net worth statement, to your budget, all the way down to your privacy and your credit. How does it work?
[00:04:50] Joe: Go check it out. Stackingbenjamins.com/vault. We got a couple more sponsors who help us keep on keeping on. We’re gonna hear from them, and then OG, Doug, and I, we’re diving into this USA Today piece about retirement suddenly being much closer for people than maybe they’d expected.
[00:05:06] Doug: If you’re in back-to-back meetings all day, you know the struggle.
[00:05:08] Doug: You’re nodding along, you’re contributing, you’re trying to stay present. You get done with the last one, you’re like, “
[00:05:13] Joe: What did we even talk about? Where do I begin with my to-do list?” This happens to me all the time. Just yesterday, I had three different interviews. I had a meeting with our team, putting our guides together.
[00:05:27] Joe: I had a meeting with the amazing Kevin Bailey about our 201. We had a script meeting, Doug and Doc G and I, going over recordings that we’re going to be doing in the near future. That’s six different meetings during the day. You finish the day, you’re like, “What did I do?” Well, the cool thing is I use Granola AI, and what is incredible is not only does it take these amazingly detailed notes, but I have, in order, what I committed to do, what they committed to do, and it’s all laid out for me in the best way that I’ve ever seen.
[00:06:01] Joe: I’ve tried a lot of different ways to take notes. Granola AI has been the best one that I’ve used. So how does it work? Well, Granola’s an AI-powered notepad built for the way real people actually meet. You take rough notes like you normally would, and in the background, Granola securely transcribes the meeting.
[00:06:19] Joe: Then it turns everything into these clean, structured, actually useful notes when the meeting ends. And the best part? It works through your device’s audio, so you don’t have to install anything. There’s no setup, no awkward bots. It just integrates seamlessly into whatever you’re using. In fact, we use a tool called Riverside for many of our interviews.
[00:06:38] Joe: Interfaces with that fine. My other meetings were on Zoom. It went phenomenally well there. It’s just your normal meeting, but with superpowers. You get to actually listen instead of frantically typing every word. You still walk away knowing exactly what was decided and who does what. So no more being called out on, “Hey, didn’t you say you were gonna do that in that meeting?”
[00:06:58] Joe: It’s all taken care of, because what’s important is always right in front of you. So if meetings are eating up your day, Granola is a no-brainer. You can try it totally free by heading to granola.ai/sb. Go to granola.ai/sb and get your time back. Once again, try it for free at granola.ai/sb.
[00:07:29] Joe: Doug, if you had to retire tomorrow, what’s the first thing you’d go panic buy at Costco?
[00:07:36] Doug: Why would I be panic buying just ’cause I was retiring tomorrow?
[00:07:39] Joe: You’re like, “Oh, my God, I need more wine.”
[00:07:41] Doug: Yeah, I mean, maybe hearing aids. I d- I mean, I don’t know. What do retirement people go panic buy at Costco? Yeah, it’s probably booze and beef.
[00:07:51] Joe: 48-pack of soup and a kayak? I don’t, I don’t- Yeah … like, what do you, what do you get a- at Costco? Well, the scary part is a lot of people don’t retire when they want to retire. It turns out the numbers are worse than I had even thought, and heck, OG, we’re around this a ton. This comes to us from USA Today, most of us retire earlier than planned.
[00:08:11] Joe: Here are the top reasons. This is written by Daniel Davisi. Daniel writes, “More than half of retirees stopped working earlier than planned according to a new report, and the decision was often beyond their control. The Retirement Risks Survey released in May by the Society of Actuaries Research Institute found that 59%” 59% of retirees left the workforce before they’d expected.
[00:08:36] Joe: Only 6% retired later than expected. I don’t know, OG, you get people that, uh, are meeting with you for the first time, maybe entering into retirement, some of them. Does this track with what you see?
[00:08:48] OG: I mean, 60% of people retiring, kind of being forced to retire? Um, I, I mean, I don’t think that that number checks with me, but I also think that we don’t have a full data set, you know?
[00:09:03] Doug: Yeah, your sphere that you’re operating in are probably not those folks.
[00:09:08] OG: Yeah, maybe not, but I know it happens, and it certainly, n- and even if it’s not retirement, it’s some sort of job change always seems to happen at the least opportune time. So maybe just expanding this idea just a little, you know, a smidge, you know, if you’re 35 watching this or listening to it or you’re 40 and going, “I don’t give a crap what happens to me when I retire, uh, it’s 20 years from now.”
[00:09:29] OG: It’s like yeah, but you could’ve been one of those 10,000 people that just got laid off.
[00:09:32] Joe: That was exactly my question when I read this was if most people retire early, why do we all plan like we control the date? ‘Cause the data shows- Yeah … that in a lot of cases we don’t control the date.
[00:09:45] OG: Yeah. The whole idea of planning is to be prepared, right?
[00:09:48] OG: Isn’t that what planning is about? You know, when you go camping or you go on vacation or you go do a thing, you’re planning it so wise. I’m planning it so that I am prepared for things that might come up. And this is why I think all of that stuff that we kind of harp on time and time again where people go, “Well, that’s boring.
[00:10:10] OG: Don’t– That’s not interesting. I only wanna talk about cool option trades.” It’s like, well, but all of this kind of feeds into the same thing. Like you, you have to have an emergency fund because statistically this might happen. You have to have a good amount of liability protection and insurance for whatever because you can get sued, and all of these things have an effect, a secondary effect on your ability to be financially independent in the manner in which you wanna be.
[00:10:39] OG: I think there’s another piece of this too, which is if you’re preparing f- as if, right? If you’re saying, “Hey, I need to save a little bit.” This is kinda side note, this is one of the problems that I have with the idea of like Coast Fire. Oh, I’m good if I just save till I’m 65 at this little rate, like it’ll compound.
[00:10:54] OG: It’s like, if you got the money till you’re 65 to save, right? If cash flow gets stopped at 57 That’s another doubling that doesn’t happen because you’re gonna start taking the money out, so. Oh,
[00:11:04] Joe: assuming that your income stream lasts as long as you projected, you mean?
[00:11:08] OG: Yeah.
[00:11:08] Joe: Yeah, so I’m not gonna save any more money.
[00:11:10] Joe: The idea of coast FI might be beyond some of our stackers, so let me share what that means, is it-
[00:11:15] OG: Maybe I’m using the terminology incorrect.
[00:11:16] Joe: Well, no, it just means that I’m gonna stop saving into my 401now because I’ve done the math, and I’m not gonna… And as long as I don’t have to withdraw from that until whatever date I’ve set my eye on, then I’m good.
[00:11:28] Joe: So you’re saying that, uh, that people that stop saving early and they’re coasting in, that assumes that your income stream will continue, and this data right here says, eh, you might be-
[00:11:39] OG: Yeah. Yeah, might not. So all of this stuff is really important, you know, making sure that you’ve got a good emergency fund, making sure that you’ve got, you know, a good savings rate, and that you’re not spending, like, literally up to the max every single month of your cash flow so that if you do have a short-term change, you have some place to, not literally draw from, but you have, you have some margin, you know, to, some buffer to kinda offset a little bit of the, the money stress.
[00:12:04] Joe: Well, let’s begin this discussion with a solution to control because I think most people think that retirement somehow is linear, right? We’ve already talked about on other episodes that retirement’s not linear at all. Even during the retirement years, OG, I mean, you’ve got the, what do they call them? The go-go years, the slow-go years, and then the no-go years.
[00:12:22] Joe: It’s a… Retirement’s gonna be bumpy, a bumpy ride as it is, but a lot of people pre-retirement think, “Well, I get to decide later when that day’s gonna be,” when you might not decide at all. We also assume that work is always gonna be available. That apparently, according to this piece, and we’ll get around to this, is something that changes where, you know, you’re 60 years old.
[00:12:45] Joe: You get let go, and you start looking for jobs, and it just ain’t happening in your field. It’s gone. There’s not the opportunity that you thought. And we also kind of assume that health stays stable, right? We did a statistic, uh, last August from the Wealthy Accountant blog showing that the average healthy retirement age- Is 66, meaning you’re gonna be healthy till you’re 66, and then really your health is gonna, uh, kinda determine what happens with your retirement years after that.
[00:13:19] OG: There’s so many, like, old guy jokes that are, like, lined up in my brain right now about that, that I … I’m just g- I’m just … I gotta get through all those before I get to the thing that I think is, uh, important to say because, I mean, if all of that is true, then you should hope to get laid off, honestly. You know what I mean?
[00:13:36] OG: Like, you should, you should hope to be forced to retire at 54, ’cause you got, you know, a dozen years to go. Look, I, I think for a lot of people who are listening, they’re saving money, they’ve got an eye on when they think they can retire, and they’re striving for a certain number, striving for a certain age, a certain timeframe.
[00:13:53] OG: Like, I wanna be done the same time my kids are done, or, you know, like, whatever. This, there’s some sort of benchmark that you have, but I think it’s a good exercise to stress test your plan against crazy stuff. Like, what if my company goes out of business tomorrow? Or what if Social Security’s not gonna be around?
[00:14:10] OG: Even if you have a very comfortable stance on both of those things, I think it’s a good exercise because you, you just never know. And you’re right, it’s never as easy as you think to just jump back in, you know, in terms of the workforce.
[00:14:25] Joe: The number one reason why people retire early, you guys wanna hazard a guess?
[00:14:30] OG: Uh, health
[00:14:31] Joe: It is. It’s your health, yeah. Health setback’s the most common reason for retiring early. The report also broke down retirement decisions for Americans of higher and lower incomes, and the differences are pretty incredible. For retirees with incomes under $35,000, the most common reason for retiring early was changes in health status, uh, presumably health setbacks for the worker or someone in their household.
[00:14:54] Joe: Job loss ranked second. Both factors fell outside of the worker’s control. For people with over, making over 75,000, the principal reason for retiring early, job dissatisfaction. D- just got sick of it. Just had had enough. The second ranked reason, achieving a retirement savings goal earlier than expected. I
[00:15:15] OG: mean, that’s encouraging.
[00:15:15] OG: That’s fantastic, yeah.
[00:15:17] Joe: Yeah.
[00:15:17] OG: That’s the second reason?
[00:15:18] Joe: Most of those fell within the worker’s control. So if you have a higher, uh, level of income, you have retired earlier than expected, but usually just because you wanted to.
[00:15:32] OG: Yeah. The other piece about the health thing that I think you glossed over for a quick second was it’s not necessarily only your health.
[00:15:39] OG: Right. It’s the health of the people around you, too.
[00:15:41] Joe: I did.
[00:15:41] OG: And in my circle of people that I’m familiar with, I’ve had two people in the last, I don’t know, three months basically say, “I’m gonna take a big step back in my career right now because I have to take care of this other person that is close to me from a health standpoint.”
[00:15:59] OG: I mean, it just happened to one of our politician people. I don’t know what her title was, I can’t remember, but Tulsi Gabbard, right? She just resigned citing her husband’s pretty significant health problems. So she’s in a different status than all of us, I suppose. Sure, but still. But that wasn’t her plan.
[00:16:15] OG: Right. You know? And so I guess the way I’m thinking about it is even if you’re looking at it going, “I’m, you know, I get my checkup every year, heart’s clean, lungs are clean, get great blood panel,” it’s like, cool, but Mom might not be as good as you, or your sister, or your brother-in-law, or, you know, whatever.
[00:16:32] OG: So if you’re called into action because you have to support somebody, it’s gonna … It could have an effect on your, uh, income, which then- You know, has an effect on your savings rate potentially
[00:16:43] Joe: Here’s a question I have. You know, when they ask people what age they thought they were going to retire at, the average worker, and this is according to the Employee Benefit Research Institute, the average worker expects to retire at age 65.
[00:17:01] Joe: 39% of people plan to retire after 70, yet the data shows they’re retiring at 62, OG. So, let’s say you’re a person that likes their job, and you say you’re gonna retire at 70. Seems to me what this data says is in your brain it’s okay to think about age 70. It’s great to think about age 70. In your planning, we should probably plan on, on going earlier.
[00:17:26] OG: I don’t understand 40% of people saying that they… That stuff doesn’t work in my brain. Not working past 70 piece, that’s not what I’m talking about. I’m talking about, like, number one reason for leaving is job dissatisfaction. Two-fifths of people think, “I’m gonna stay working at my job till past 70.” So one of those things is not working together.
[00:17:45] OG: Well, yeah. Unless it’s the, unless it’s people who are saying, “I’m planning on working past 70 ’cause I ain’t got no money.”
[00:17:50] Joe: I think what that says is something- Right, right. That’s what I think
[00:17:51] Doug: it is …
[00:17:52] Joe: Well, I actually think it’s something different, Doug. I think it’s we predict how we’re going to feel when we’re 60 when we’re 40 We, we predict
[00:18:01] OG: How, how are you feeling?
[00:18:02] Joe: Yeah, at f-
[00:18:02] OG: How are you guys feeling right
[00:18:03] Joe: now? At, at 40, I know how I’m gonna feel when I’m 70. Tired.
[00:18:06] Doug: Just so tired, OG.
[00:18:08] OG: Guys, like how is it starting to feel, guys? I just out of curiosity.
[00:18:11] Joe: Well, you see these people who are 30 years old. How, how many times have we seen this, right? Some, uh, quote, “influencer” who’s 30 and retired is setting the trajectory of their life, and you can look at this person and go, “There’s no way you’re gonna feel about this the way you do.”
[00:18:26] Joe: That, you know, $200,000 in a Vanguard total index fund and your Coast FI is gonna be plenty. Mm. Like, you’re setting this very, very strict collar around what- Yeah … the rest of your life looks like when you don’t have any idea. That’s what I think it is. I think people get to 60, Doug, and they go, “You know what?
[00:18:44] Joe: I thought I was gonna be fine. I fricking hate it.”
[00:18:47] Doug: Yeah. “
[00:18:47] Joe: I thought I’d do this till 70.” I mean, we did this story about how corporate culture is BS. Ashley Goodall had written a piece in the Harvard Business Review, wrote a book with Marcus Buckingham, then more famously came on into the Stacking Benjamin show and talked about it.
[00:19:02] Joe: But corporate culture- Much more famously … is BS. Your corporate culture is the five people you work with every day, and if your manager changes, everything changes. You could be 60 years old and love it. 61 years old- Yep … your boss changes, you’re done.
[00:19:17] Doug: Some punk kid, 28-year-old’s now suddenly your boss, and you’ve just had enough of that.
[00:19:22] Joe: Doug, I remember this, just if you don’t mind, in your career, like, I remember where I was in some of the discussions about Doug got a new boss, and the new boss changed everything.
[00:19:33] Doug: Oh, it does, and I think that is still, long time running, the number one reason people leave their job is because of their immediate supervisor.
[00:19:41] Joe: My daughter, that was her reason. My son- Yeah … that was- It
[00:19:45] Doug: sets the tone for everything. Even if their management above them are amazing or if the culture is pretty great, that’ll maybe keep you hanging on a little longer. But eventually, if your direct supervisor is not meshing with your personal culture, you’re probably gonna check out
[00:20:01] Joe: Overall top five reasons people left their job.
[00:20:03] Joe: Change in health status, we mentioned earlier, 31%. Job dissatisfaction, 25%. Job went away, and I just decided, “You know what? I’m just not going back. I’m not gonna start up some other thing.” That’s 20
[00:20:17] Doug: per- Thanks,
[00:20:17] Joe: AI That’s 20% of people. Change in family situation, what you’re talking about, OG, something happened at home, 19%.
[00:20:24] Joe: And then 16% achieved a retirement savings goal earlier than, than expected. But all these, OG, point to, uh, plan on an earlier retirement just in case. You may need that parachute.
[00:20:37] OG: Yeah, s- stress testing early retirement to see- Right … what you would do if that happens to you. Is- Yep, I agree …
[00:20:41] Doug: is this an appropriate analogy?
[00:20:43] Doug: It feels a, a little bit like when we say, “Get a 30-year mortgage, but pay on it like it’s a 15-year mortgage. And then if you have to fall back because you’ve lost a job, you can fall back to that lower payment of the 30-year mortgage, you know, minimum payment.” Is that a little bit analogous to plan for the early retirement, and then if you don’t have to, awesome?
[00:21:05] Joe: And it’s interesting, OG, because, you know, you’ve talked about the 15-year mortgage before, but if you’ve got this payment structure, you talked about how a lot of people stay in the job because, “I just have to. I need the cash.”
[00:21:16] OG: Mm-hmm. I think what Doug’s saying is plan as if you have 15 years to go.
[00:21:21] Doug: Yeah.
[00:21:22] OG: Save as if, and then if you really have 30, then you’re gonna be great. You’re gonna be in great shape I mean, I can see that. I’ll, I’ll, I’ll allow it, Your Honor, as an analogy.
[00:21:33] Joe: There’s a piece of this that is difficult, and OG, you see this more and more in retirement planning, which is not about the money.
[00:21:39] Joe: It’s this emotional stumbling block. All of a sudden I didn’t expect to retire at age 62. Now all of a sudden I’m on the bench even though I didn’t really plan to be. I think that can make the early years of retirement difficult as well.
[00:21:54] OG: Well, the early years are always gonna be a little bit wild from a lot of reasons.
[00:21:59] OG: I mean, there’s the pent-up demand of all the stuff that you wanna get done, like, “Oh, finally I get to take the cruise, go to the safari, travel the world, see the kids, hike the mountains. Like, I can do all this stuff.” And so there’s… It’s a little wild from that perspective a lot of times. It’s wild because you’ve got a new rhythm to trying to figure out what the hell you’re gonna do every single day.
[00:22:22] OG: It’s wild because of your relationships changing with the people that are around you, because if you have been traveling to work every day at 7:00 AM and coming home at 6:00 PM every day for the last 35 years, and now you get up at 6:30 like you normally did, but now you’re having breakfast with your spouse, who by the way, is used to it being quiet and not listening to your television program, but hers or his, you know.
[00:22:44] OG: T- you know what I mean? Like, there’s just, it’s just a whole new thing for everybody across the board. And then if you add to that any sort of money stress, you know, you can see how this can be a pretty, uh, exciting, for lack of a better term- Yeah. Yeah … time. Which I think is why we talk… and Joe, you talk about this more than anything, it’s like, if you have the opportunity to take a, a block of time off and test it, this is a really great reason for that, because you can say, “Well, what would I do if I had three months off?
[00:23:14] OG: You know, if I had two months off? What-” What am I gonna fill my time with? Because you can go on vacation for a week and get a little detox, or two weeks and sit on the beach and read a book or two, kind of that’s piled up maybe in the last year. But if you take six weeks off, or you take eight weeks off, or 16 weeks off, that’s a different experience.
[00:23:35] Joe: I used to think that all these different pieces of planning were all separate, but really, the older I get, the more I see that they all merge into each other. A- and as I walk down all these reasons why people leave their jobs, I thought it’d be good to finish out this conversation by giving people some tactical things to do.
[00:23:52] Joe: But we gotta start off with health flexibility, and you and I are not health experts by any stretch of the imagination. There’s people that have-
[00:23:59] OG: False, but okay
[00:24:00] Joe: that have, that have spent their entire career coaching people on health and wellness. But I gotta think, number one, prioritizing your preventative care.
[00:24:12] Joe: Number two, funding that HSA. Beth Pinsker, who will be on the show on Wednesday, she and I were chatting earlier, and we were t- she was talking about how, in all the research she’s done around HSAs, most of them are drastically underfunded, people not putting anywhere near the amount of money in an HSA that they probably should.
[00:24:32] Joe: But finding that. The third, I think, y- you know, but what, what’s the insurance people always minimize, OG? Disability insurance, and yet it’s the health scare that ends up being the reason why we find ourself maybe needing money sooner than we thought.
[00:24:46] OG: On the preventative piece, I think that’s probably the only thing I can really speak to.
[00:24:51] OG: The HSA component, you know, I think is really important because, you know, it gives you, you know, just another bucket of savings. But the reality is it’s like if you’re maxing out your IRAs, maxing out your 401ks, and you’re in a two-person household, the HSA would put you at what? The 70,000th dollar of savings for the year, like if you’re on that level.
[00:25:11] OG: So y- you’re already doing pretty good if you’re maxing out, you know, a couple 401Ks, maxing out a couple Roth IRAs, and you still have eight grand left over, cool, use the HSA. Um-
[00:25:22] Joe: Should you be flipping around the priority of that, though?
[00:25:25] OG: Well, I, I’m not sure. I, it’s, it’s very highly dependent on, you know, your personal situation because the thing everybody loves to talk about HSAs in the context of, like, it’s a tax-free savings vehicle, and it’s amazing.
[00:25:38] OG: You invest the money and it’s like, well, yeah, but you have to pay for more stuff out of pocket. So, you know, you gotta weigh that out. Yeah, and, and, and you know, we’ve talked about this over the years. When, when we were having kids, we would change our health insurance because it didn’t make sense to have all that out-of-pocket costs in the year that the babies were being born because, yeah, we didn’t put money in an HSA that year because we had all this other healthcare stuff.
[00:26:03] OG: And so if you do the HSA, you gotta be okay with floating a big tax bill or a big, a big insurance bill to the tune of, you know, whatever that is, 15 or $20,000 a year. So I think that’s a piece. The, the preventative thing I think is really important because it’s so inexpensive. A, it’s probably covered from your health insurance anyway, you know, an annual care visit, you know, whatever.
[00:26:25] OG: A year ago I bragged for how many shows about a colonoscopy, guys? I don’t know, like eight- I think about 26,
[00:26:31] Joe: Doug. Doesn’t
[00:26:31] OG: it feel like 26? Eight shows in
[00:26:32] Joe: a row?
[00:26:33] Doug: Yeah.
[00:26:33] OG: That was, it probably wasn’t a half… Well, I mean, I was gonna say half a year, but it wasn’t that long. But that’s covered as preventative generally speaking.
[00:26:41] OG: Probably most people forego doing health stuff because they’re scared of what they might find, which is a fair assessment. You know? Like I’d rather the devil you know versus the devil you don’t. I get that. But in our day and age, there’s so much stuff that is treatable and preventable if you catch it early.
[00:26:58] OG: So your quality of life will be a thousand times better if you Take care of yourself. It doesn’t matter how much frigging money you have
[00:27:07] Doug: Plus, if you really build up that HSA, you can pay for unexpected car repairs, like that one stacker of ours did.
[00:27:12] Joe: I love the callbacks, the callback to past episodes.
[00:27:16] Joe: Doug specialty
[00:27:17] Doug: It’s just a hack. It’s just a hack that I think everybody should know about.
[00:27:20] Joe: It’s just… may or may not work. May not, with emphasis on may not. Uh, second, this issue of retirement being binary, to the extent that you can try to mitigate that is gonna be important. So can you consult? Can you freelance?
[00:27:36] Joe: Can you work part-time? Can you pivot careers? Even if you’ve had an employer that has seemed stable for the past 10, 15, 20 years, and you feel like you’re gonna be there forever, as we mentioned, one manager could change everything, so remembering to network is probably, uh, and keeping the door open for the future of more income could be a huge win.
[00:27:57] OG: Yeah. Yep, super important.
[00:27:59] Joe: Third, I think, is on the expense side. Of course, you know, most financial shows, I think, focus on expenses. I think it’s always important to focus on income streams first. Are there fixed costs that you can lower? Are there ways that you can work on maybe paying off your house early?
[00:28:18] Joe: You’ve talked about that, OG, so that you don’t have that mortgage payment hanging over your head, and avoid over committed living. I think that becomes even more important when you know that you might go early.
[00:28:28] OG: Anything you can do to reduce the money that goes out every single solitary month regardless of what you choose to do makes your life a thousand times better.
[00:28:36] Joe: I remember I was a brand-new business owner, and I was bragging up to a guy that had been in business for a long time about how I was gonna have three different locations of this particular business that I was running, and he just looks at me and goes, “Keep your overhead low. You might wanna rethink that.
[00:28:51] Joe: Why have three locations when you could just have one?” And I was like, “Oh, that’s stupid” . And now, and, and now I’m like that dude. Way, way, way, way, way, way smarter than, uh, than having three locations Good stuff. Uh, we will link to this piece from USA Today on our show notes page if you’d like to dive into that.
[00:29:10] Joe: Of course, Kevin Bailey, who has worked for Vanguard and TIAA, and is a great writer of our 201, Kevin’s gonna dive into a hot take from today’s piece on our 201 newsletter that comes out once a week. You can sign up for that for free at stackingbenjamins.com/201. Well, coming up in just a moment, OG and Anna talk about equity compensation.
[00:29:35] Joe: But before that, Doug has maybe the best trivia he’s ever had. The bar is very high, Doug, very high.
[00:29:42] Doug: Wow, you’re just setting me up for failure, aren’t you, Joe? Hey there, Stackers, I’m Joe’s mom’s neighbor, Doug, and today’s trivia question is brought to you by the number seven, which coincidentally is also the number of times Mom has told Joe that if he doesn’t clean out the freezer downstairs, she’s gonna retire him early from the basement.
[00:30:01] Doug: Speaking of retirement, on this date in 1969, the Yankees officially retired the number seven, belonging to this legendary switch hitter, which proves that unlike most internet financial independence experts, some people don’t actually just talk about retirement, they do it.
[00:30:18] Joe: Ooh,
[00:30:18] Doug: there’s a
[00:30:19] Joe: hot take.
[00:30:19] Doug: So, whoa.
[00:30:20] Doug: There
[00:30:20] Joe: is a,
[00:30:22] Doug: pss, it’s like a pugilistic verbal jab. So who was the baseball legend whose number got the gold watch treatment while we’re still down here using the card table as a standing desk? I’ll be back with the answer right after I go check to see if I can get my number retired, too. I’m practically a legend down here, right?
[00:30:54] Doug: Hey, stackers. I’m podcasting trivia legend, but guy without a number on his shirt, so he can’t get retired, Joe’s mom’s neighbor, Doug. We’re talking retirement today, and honestly, around this basement, early retirement usually just means mom found another one of Joe’s half-finished financial spreadsheets in the laundry room and threatened to change the Wi-Fi password again.
[00:31:13] Doug: Now, today’s trivia takes us back to the New York Yankees, and for our non-sports stackers, yeah, that’s a baseball team. The Yankees today are worth over eight billion dollars, which means if you’d invested in the Yankees instead of Joe’s mom’s brief but really passionate lava lamp startup, you might actually be retiring early.
[00:31:32] Doug: And speaking of money, the player we’re talking about made around 100,000
[00:31:39] Doug: a year near the end of his career. Today, that amount just gets you approximately three innings at Yankee Stadium, one foam finger, and a parking for Joe’s aggressively practical Chevy Equinox. Aggressively practical But on today’s date back in 1969, what does that mean, aggressively practical? Is it just incredibly boring?
[00:32:01] Joe: Just where do you come up with that stuff?
[00:32:04] Doug: But on today’s date back in 1969, the Yankees officially retired the number seven after this legendary switch hitter helped lead the team through the glory years of the ’50s and ’60s. So who was this player whose number was retired on today’s date back in 1969?
[00:32:21] Doug: It was none other than Mickey Mantle. And now two people on the Mantle with all the financial education greats, let’s turn this over to OG and Anna.
[00:32:33] OG: Anna, we are back, episode five, season two. Today we’re gonna talk about equity compensation. So this is something that’s kind of, uh, top of mind for a lot of people.
[00:32:42] OG: Uh, everybody either lights up about this or their eyes kind of glaze over, ’cause either they have it or don’t have it. But the people that don’t have it might have it at some point in time.
[00:32:51] Anna: Mm-hmm.
[00:32:52] OG: This could be something worthwhile.
[00:32:54] Anna: Right. And if you have it, you really need to pay attention to this one, because I feel like people get equity comp and they’re like, “This is amazing.
[00:33:00] Anna: I love this. What in the heck does this mean?” So this is where we kind of break down a couple categories of equity compensation. Some of them are really complicated and some of them are a little bit easier to dive into. So we’ll get into that today.
[00:33:14] OG: I was gonna say, it kind of feels just like a bonus just falls from the sky.
[00:33:18] OG: Like, ooh. Mm-hmm. Yay. RSUs. Cool. Now what?
[00:33:21] Anna: Yeah. Yeah, but all of them earn a little bit differently. So if you get an X amount of shares of RSUs, X amount of shares of stock options, those are very different. That’s a different dollar amount for you. That’s a different tax situation that comes up. So it’s important to understand how that all works and what your strategy is.
[00:33:38] Anna: That’s really the big thing here, is, like, you wanna have a common strategy that you’re doing for every time you have a grant, every time that that grant then continues to vest. That’s what the workbook should help you walk through and come up with.
[00:33:51] OG: And the whole idea of having the strategy is that you’re putting your investment policy statement to work at the same time as your equity strategy, so you’re not gonna be trapped in the, “Well, I think maybe the stock might go up,” or, “Oh my gosh, the stock might go down.”
[00:34:06] OG: You just have a consistent thing to exercise or execute, I think is a better way to say that, to execute over time. It takes that guesswork out of it.
[00:34:15] Anna: Yeah, absolutely. We can get into the different categories that we have. So the most common that we see are RSUs, and they’re pretty easy, honestly. You pretty much will get a grant, and then they earn a vest over a specific time.
[00:34:31] Anna: And RSUs, like, really function similarly to a cash bonus in a way. When you’re given the stock, you’re given the full value of the stock. Whereas if we look at a stock option, you’re basically given the option to purchase your company stock at a specific time, at a specific price, and so you’re not just given, like, the full value of the, the share.
[00:34:55] Anna: It’s basically you’re given a discount on the share.
[00:34:58] OG: And usually RSUs have that vesting scale that is traditionally a little bit quicker- Mm-hmm … because it’s your bonus money.
[00:35:05] letters: Mm-hmm.
[00:35:05] OG: And, uh, non-qualified options or incentive options maybe have a little bit longer run rate, because at the end of the day, there’s a lot more risk involved with your value of that.
[00:35:17] opener: Mm-hmm.
[00:35:18] OG: But also, there’s a lot more return potential with the value of that because, you know, if the stock really explodes in value, you could have a, uh, a pretty successful outcome, I guess, is the way to think about that. So for most people, if they have equity comp, generally speaking, we’re talking about RSUs.
[00:35:38] Anna: Yeah, for the most part. And you might be even given, like, multiple different types within, which that’s where it really gets confusing. You’re like, “Oh, I have these RSUs. I have these ISOs,” which is a type of stock option like you mentioned. Right. And then the other one we didn’t mention was ESPPs.
[00:35:52] opener: Mm.
[00:35:52] Anna: Basically, it’s another form of discount, but you’re purchasing it typically at a cadence throughout the year. Like, your company will let you purchase every quarter. It’s deducted from your pay biweekly, monthly, however you get paid, and they’ll give you a up to 15% discount on the share price of today, of the day that you’re purchasing it.
[00:36:12] Anna: Yeah. A lot of companies offer this. It’s not really something where you have to, like, qualify for it or get the R- like, it’s not similar to an RSUs. It’s just kind of like, “Hey, you have this opportunity to buy IRC or ESPPs.”
[00:36:26] OG: All right. So let’s talk a little bit about w- working through the workbook here. So the first step that we wanna do is really just to kind of take an inventory of- what you have.
[00:36:36] Anna: Let’s open up the workbook. Onto step one, log into the custodian where your RSUs stock options, ESPPs are all located. And you basically wanna fill this out with how many shares are you currently granted, which is, like, total amount. You might have multiple grants.
[00:36:52] opener: Mm-hmm.
[00:36:52] Anna: You wanna tally all those up. Then you’re gonna look at how much of that is vested, meaning how much could you sell today, and then how much is unvested, meaning it’s going to vest in the future, which could be later this year, it could be years in the future.
[00:37:07] Anna: And you’re just gonna write that dollar value. You can look at it in, with today’s share price- Right … just knowing that it’s gonna change. So by the time it vests and you are gonna have the opportunity to actually sell that or own that share, it could be a different dollar value, but just using today’s price.
[00:37:22] Anna: And then tally all that up on the right-hand side with the total value in each category there.
[00:37:28] OG: Well, and this is really important, this inventory idea and the different tranches, because if you’ve been at a company for a period of time, you could have a lot of different grants, a lot of different RSUs vesting at a lot of different times.
[00:37:40] OG: You know, that causes tax issues, that causes diversification issues that we’re gonna talk about, lots of different things. So just having an inventory really sets the stage for all the rest of the decision pieces.
[00:37:51] Anna: Yeah. And part of that, too, is just to understand how much of your net worth is tied up in this specific company.
[00:38:00] Anna: And not only do we have RSUs or ISOs or ESPPs in this company, but we also have your paycheck- … coming from this company.
[00:38:10] OG: Your job is the company.
[00:38:11] Anna: Yeah. So that’s not something to dismiss and not include when you’re thinking about your total exposure to this company and how much of your net worth is potentially tied up in this.
[00:38:23] Anna: We talk so much about diversification, so it’s really important to understand this number and then come up with a strategy to unwind a lot of this and get you into a more diversified portfolio.
[00:38:36] OG: If you look at your equity comp and all those other pieces of your life that’s tied into this one organization, you can kinda see the risk.
[00:38:45] OG: Now, this also can be very successful and also very risky at the same time. Those things are not mutually exclusive, right? Mm-hmm. Like, you can have a lot of risk and a lot of success, but don’t trap yourself into thinking, “Well, I know what’s going on behind the scenes here,” so.
[00:39:00] Doug: Mm-hmm.
[00:39:00] OG: If you did know what was going on be- behind the scenes, you couldn’t act on it.
[00:39:05] OG: So if you’re high enough up that you really do know what’s going on behind the scenes, you have lots of money probably, so that becomes less of an issue. Even though it is a concentration risk, it’s like, well, 40% of my $600 million net worth is tied up in this, kinda just like, yeah, okay, well, you’re still gonna be okay.
[00:39:22] OG: But if you’re a mid-level or an executive level person without all of those details, the reality is you can’t act on it anyway even if you did, and there’s probably some stuff that you don’t know, so just be aware of it. Where should we start in terms of max exposure from an allocation standpoint?
[00:39:39] Anna: Max exposure should probably be somewhere between, like, 5 to 10% of your net worth tied up in, like, what I would say is currently vested, ’cause you can’t control your unvested shares.
[00:39:52] Anna: Mm-hmm. It’s good to understand, like, what’s on the horizon for you, but in terms of actual vested, I wouldn’t really let it go over that amount. Now, your strategy of if that’s, like, all RSUs, all stock options, it’s gonna look a little bit different as to, like, are we gonna let that creep up a little bit because it’s stock options, and we kind of wanna wait until we get closer to expiration date?
[00:40:16] Anna: Yeah, maybe. Is it RSUs that have already vested, and we could have sold them for the price that they were vested at, and now we’re just letting them kind of, like, bounce around at the stock price? That’s more so where I would be like, “Yeah, let’s get rid of a lot of those RSUs and diversify them.” Stock options, on the other hand, I would prefer to let that creep up a little bit and let yourself hold onto those until you get a little bit closer to expiration date.
[00:40:46] OG: So now that you know what the allocation looks like, and maybe what you want it to look like- Now I guess you gotta have a plan for what are you gonna do with this liquidity, right? You’ve decided, okay, I’m at 25%, I want it to go down to 15 short-term, I want it to go to five long-term, so therefore I’m gonna have this bucket of money.
[00:41:04] OG: Now what?
[00:41:05] Anna: Like you said in the beginning of the episode, we can look at this as more of like a bonus. Like think about it as a bonus, ’cause that’s really what it is and what the company’s trying to incentivize you with-
[00:41:15] OG: Right …
[00:41:15] Anna: um, by giving you this. So when you think of bonuses, we think about how much of that is gonna go towards investing, how much that is gonna go towards debt pay down, how much of that is gonna go towards fun spending, vacations, or a new toy you want.
[00:41:30] Anna: A- whatever that is. Let’s come up with a percentage that’s right for you and your family. Maybe debt pay down is really, really important right now. Maybe there’s student loans, maybe there’s credit card, maybe that number is 100% that’s gonna go towards debt- Mm-hmm … until we get… You know, we’re gonna talk about debt in our next episode, but- I was gonna
[00:41:47] OG: say, foreshadowing.
[00:41:48] Anna: Yeah.
[00:41:48] OG: Foreshadowing alert.
[00:41:49] Anna: Everyone is gonna be different. There is no person that needs to be the same allocation between all three of those buckets. It is really what’s the priority in your family today, what are you guys focusing on right now? But it’s good to have those numbers ahead of time so that you don’t get the like $60,000 RSU-
[00:42:07] Anna: and then you’re just like, “Oh, let’s start- Woo-hoo … our pool project,” you know, and you need all of the money.
[00:42:11] OG: Not saying you can’t do that, but if you thought about that a year ahead of time, then that makes that decision easier. You’re trying to avoid decision fatigue of like, okay, I gotta make all these decisions.
[00:42:20] OG: How much do I sell? When do I sell? How do I pay the taxes? What am I gonna do with the money once I do sell it? That’s a lot of stuff to deal with, number one. And then number two, you’re trying to avoid all the emotional regret that comes with spending money. Like- Mm-hmm … it’s your money, you should be able to spend it, but you should do it in a way that makes you feel good about your decision-making.
[00:42:36] OG: And what we found is people feel good about decisions when they have had time to prepare for them in advance, and they’ve kinda come complete circle in that. The last little piece on this is there’s a bunch of tax problems here, too, as well, and I know we could spend like a whole episode on taxation of- equity comp, and we focused on RSUs.
[00:42:58] OG: There’s d- different kinds as well, but talk about how the functionality works around taxes with RSU vesting. What’s gonna happen? What’s likely to happen in the future? What do people have to know about taxes and vesting of your RSUs?
[00:43:13] Anna: RSUs specifically, they’re gonna be taxed when they vest, not when they’re granted to you.
[00:43:19] Anna: So you get a bunch of RSUs, it’s not like you’re gonna have a big tax bill that day. They get taxed on the day that they’re vested at the price that they vest at, and typically, your company is going to, I mean, this is an election that you can make, but it’s typically defaulted to this, where you can sell a certain amount of shares to cover the taxes on that.
[00:43:42] Anna: Right. Sometimes it’s still under withholding taxes for you, so that’s something to be aware of. Like, oh, yeah, my, you know, my company sold some of this, so we’re fine. We’re gonna pay taxes on it. You might still have a big tax bill come April. It’s important to understand what withholding they’re using. Do you guys fall into that bracket, or do you potentially just wanna keep an eye out for an extra tax bill that comes down the line?
[00:44:06] OG: Yeah, that’s, I was gonna say, that’s where we see a lot of surprises. It’s withheld at 22% or 25%, but I’m really in the 37% bracket because of this bonus, because of this grant, and now I owe a tax bill of, you know, $20,000, and I spent all my RSU money on a pool.
[00:44:20] Anna: Yeah.
[00:44:21] OG: So.
[00:44:21] Anna: So it’s good to have an eye out on that.
[00:44:24] Anna: The other piece to this is that whether you sell your RSUs or not, you’re paying the taxes on them. When they’re given to you, if they’re still sitting in your company’s stock, and you didn’t actually go in and s- liquidate it to put it into cash or diversify it, you’re still paying taxes on that. Now, if you hold onto it, like I said, you didn’t sell it, you’re gonna pay taxes, ordinary income, when they vest, and then if that stock price continues to go up, and then you sell it in the future, you’re then gonna pay long-term capital gains, as long as it’s held for a year.
[00:45:00] Anna: Mm-hmm. Long-term capital gains on the growth of that between the vesting date and the date that you sell it. So that’s something to keep in mind, too. If you’ve held onto it for nine months, and now you’re thinking about selling it, maybe hold onto it for another three months, get that long-term capital gain rate, and sell it when it hits that year mark.
[00:45:20] OG: One last quick thing before we wrap up. If I’m the person that has kind of two problems going on, I’ve got a bunch of stuff I haven’t addressed, so I’ve got this big concentration problem, I’m also in a high tax bracket, am I just gonna eat it and get it right or spread it out over time? Is there a strategy to this, or is this more unique person by person, do you think?
[00:45:41] Anna: Everything’s unique person to person, but- Correct
[00:45:43] OG: answer. Good job.
[00:45:45] Anna: Which is why you need to talk to us about your individual problems. Just kidding. If you are s- very concentrated in this position, you need to weigh the risks here. Is the risk that we take on a lot of taxes in one year but we’re unwinding a lot of the exposure that you have to that company, is that worth the tax bill?
[00:46:07] Anna: Sometimes yes. Um, unless you’re doing intense tax planning where you know, like, okay, let’s sell X amount of stock options this year to get you to the top of the 24% tax bracket or 32% tax bracket, whatever that is, like, it is really hard to be able to predict all of that and, and play that out throughout the year.
[00:46:28] Anna: And so sometimes it is like, yeah, we’re just gonna unwind it in one year, and we’re gonna take that tax bill. It really does depend-
[00:46:36] OG: On what problem you’re trying to solve.
[00:46:38] Anna: Yeah.
[00:46:39] OG: Okay. So just kind of wrapping up then, as you work through this worksheet, take an inventory of what you have, figure out the percentage of, of your net worth relative to your company stock.
[00:46:50] OG: Decide on the vesting schedule and mapping out in advance what you’re gonna do for every dollar that shows up in your life, like you would a bonus. This is a bonus. It’s a cash bonus that your company gave you as company stock, and you get to choose to keep it in that or not, or to spend it on other things like debt paydown and the stuff we talked about.
[00:47:08] OG: Next week we’re gonna talk about debt, my favorite topic. I love having debt. It’s amazing. We will, uh, we will unpack the psychosis of that next Monday. So two things, if you don’t have the guidebook, stackingbenjamins.com/basicsguide will get you a copy of the guidebook. If you wanna do the scorecard to see how you rate yourself and maybe how you rate yourself against other people, that is very simply stackingbenjamins.com/scorecard.
[00:47:33] OG: /scorecard, /basicsguide, two different paths, but, um-
[00:47:37] Anna: Both amazing …
[00:47:38] OG: both amazing outcomes. Uh, see you next week.
[00:47:41] Anna: Bye.
[00:47:43] bumper: Hey, this is Jen Pilcher, Navy spouse, and when I’m not helping military spouses connect in our digital community, I’m stacking Benjamins. And
[00:47:52] Joe: there you have it, equity compensation at its, at its best Back to the trivia for a second.
[00:47:59] Joe: I just went to, uh, Yankee Stadium, Doug. Have you been to the new Yankee Stadium?
[00:48:03] Doug: I haven’t been to either Yankee Stadium. I’d like to go to the old one first.
[00:48:06] Joe: Well, I got some good news and some bad news.
[00:48:09] Doug: Oh, what’s that?
[00:48:10] Joe: We should start with the bad news. Uh, that is, may have been demolished. However- Is
[00:48:15] Doug: it a parking lot now?
[00:48:16] Joe: It is a parking lot. We, we, we went the year, the last year it was around, and we really liked it. The new one actually kept a bunch of the same flavor, but obviously with more luxury boxes, and to your point, the price tag slightly, slightly higher.
[00:48:30] Doug: Yeah, I think they’re charging more for the flavor now.
[00:48:32] Joe: It is.
[00:48:33] Joe: It is a little bit more flavor-tastic. But a nice place to watch a ballgame, good place to watch a baseball game. I’m going back to New York, by the way, to see the Mets. I finally am gonna get to see the Mets and the Orioles this year.
[00:48:47] Doug: So you’re going to a minor league game?
[00:48:48] Joe: I am. If, if only, if only a major league team played that stadium.
[00:48:53] Joe: All right, enough baseball jokes. Let’s move out to the… We, we lost half our audience going, “What? Wait, what? Huh?” The other half, though, thinks we’re hilarious.
[00:49:01] Doug: I’ll take
[00:49:01] Joe: it. Let’s chat about, uh, what’s on the back porch because- We just got a letter.
[00:49:08] letters: We just got a letter. We just got a letter. We just got a letter.
[00:49:13] letters: Wonder who it’s
[00:49:15] Doug: from. Joe, before we get to the letter, I don’t know, 10 days ago or so you posted a poll in the basement, and I, I would like to respectfully ask that you make the question much more quickly apparent, because I just clicked on the answer option multiple times a day before I fully read the question, just assuming I knew what the question was.
[00:49:39] Doug: Turns out it was, it was just about how often you check your, your portfolio and your-
[00:49:45] Joe: Why,
[00:49:46] Doug: so what did you- … and the market’s making headlines. Why?
Why?
[00:49:48] Joe: What was the-
[00:49:48] Doug: What else could it be, Joe? What were
[00:49:50] Joe: the
[00:49:50] Doug: answers, Doug? Multiple times a day, once a day, once a week or less. I mean, come on, we’re not dead.
[00:49:57] Joe: Are you worried about going blind?
[00:50:00] Joe: Is that what you’re worried about?
[00:50:01] Doug: I didn’t like… I felt like it was bait and switch when you put those answers out
there.
[00:50:05] Joe: Seriously, Steve plays the Blue’s Clues music, we do the whole thing about the letter, and you got interrupted all for a, uh-
[00:50:13] Doug: Yeah, I just- For a little- It, it was just a public request, ’cause I think there’s a lot of other stackers out there that got faded
[00:50:19] Joe: into that.
[00:50:19] Joe: Well, let’s chat about this then, since you went there. Seriously, we, we did a poll in our Facebook group, The Basement, because I was wondering after Simone Stolzoff was on talking about uncertainty and how we can find ways to deal more with uncertainty, I was wondering how often people check their accounts when there is news.
[00:50:40] Joe: And it, it was what, more than once a day, once a day, uh, once a week. People put in a few other ones. A few times a week. Right. I know our friend Nords, uh, Doug Norbin, a great, uh, military money writer. Nords wrote, “Whenever my friends, like, tell me something interesting is happening.” Uh, we had a few,
[00:50:58] Doug: but- Honestly, almost every one of these alternative options still works with what I thought the question originally was.
[00:51:06] Doug: Whenever my friends get excited, I mean, that works.
[00:51:09] Joe: If my friends get excited-
[00:51:11] Doug: As scheduled.
[00:51:12] Joe: How did these come down? How did the answers come down, Doug? How often do people… And by the way, what I didn’t wanna do, ’cause you know, the internet’s a place people brag, “Well, I never get worried. I never check mine.”
[00:51:21] Joe: I gotta tell you, I don’t know if this is the case for you, OG, but for me, when I was an advisor, my clients that told me they worried the least were the ones that called me every stinking time the market went down. “What do we do? What should we do?” I’m like, “I thought you don’t panic.” “Oh, I’m not panicking at all.
[00:51:37] Joe: I wonder if there’s some strategy we should do to move stuff around.” Yeah, okay.
[00:51:41] Doug: So a resounding 44% of respondents said that they check their portfolio once a week or less. Number two was once a day. And number three, my camp, multiple times a day. Uh, and then, you know, few times a week, 11%, and then we get into the single digits after that.
[00:52:01] Joe: Yeah, yeah. 44% of people said that they’re pretty stoic about it.
[00:52:06] Doug: Once a week or less.
[00:52:06] Joe: And then the second highest was once a day.
[00:52:09] Doug: Yep.
[00:52:10] Joe: And that, that… What percentage was that?
[00:52:11] Doug: Once a day was 17%.
[00:52:13] Joe: 17%.
[00:52:13] Doug: Decent chunk of people.
[00:52:14] Joe: Yeah. Yeah, and I think the number’s probably a little bigger than that, but we don’t wanna, you know, we don’t wanna admit that we’re hitting refresh on the old brokerage account.
[00:52:24] Doug: W- why is the door always closed when you’re checking your account multiple times a day?
[00:52:29] Joe: I don’t, don’t know where you’re going with this, Doug.
[00:52:31] Doug: That’s a lot of showers. Uh…
[00:52:34] Joe: Hey, Steve. I- Hey S- Hey, Steve, guess what? We just got a letter.
[00:52:39] letters: We just got a letter. We just got a letter. We just got a letter. Wonder who it’s from.
[00:52:46] Doug: All right. Should we get to the letter?
[00:52:47] Joe: Yes, ’cause Kiki wrote us a kickass
[00:52:49] Doug: letter. Yeah. Yeah, Stacker Kiki, great name, Kiki, is getting intentional with her spending, and she wrote to us for accountability. Her note was, “Hello, Joe and team. Longtime listeners, at least, since at least 2016, and always enjoy seeing one of y’all’s podcasts in my feed.”
[00:53:06] Doug: So right there, we know she’s from New England when she said y’all’s podcast. “In response to the latest podcast, Intentional Spending,” which was, for those of you keeping score at home, episode 1845, “Here are some items I will and will not cut back on.” So here are the things that, that Kiki will cut back on, but I like how she put with caveats.
[00:53:26] Doug: Like, she’s giving herself a backdoor if she really needs it. Anyway, she will be cutting back on restaurants unless she has a coupon.
[00:53:33] Joe: Okay.
[00:53:34] Doug: Property taxes, just s- she just successfully protested and dropped the valuation down 22,000.
[00:53:41] Joe: You’re on that train, OG, aren’t you?
[00:53:43] OG: Yeah, big time.
[00:53:44] Joe: Yeah.
[00:53:44] Doug: Yeah. She will be cutting back on extra grocery items unless they’re on deep discount, and, uh, they have room in the freezer or the pantry.
[00:53:53] Doug: Travel, unless work related. Alcohol. See, that’s where she lost me, right there. And cut, Kiki. She’s cutting back on the alcohol.
[00:53:58] Joe: A bridge too far.
[00:54:00] Doug: Okay. Let’s, what’s the next segment, Joe? Uh, no, she’s also cutting back- Fun. I’m
[00:54:04] OG: cutting out fun. I’m cutting out any excitement.
[00:54:07] Doug: Any joy in my life.
[00:54:09] OG: Joy.
[00:54:12] Doug: And this plays right into that theme, also cutting out entertainment unless a deal is found, junk food…
[00:54:18] Doug: Oh my God She’s going into solitary confinement, I think. Clothing, I’m actually a fan of this one. Personal care products, use up any extras until they were gone and/or find items at deep discount. Here are the non-negotiables that Kiki will not be cutting.
[00:54:35] OG: Actually, the personal stuff, the toiletries and that sort of thing, I actually think is a great idea.
[00:54:39] OG: I don’t know if you guys have this. I have a drawer full of, like, hotel lotion and soap and-
[00:54:44] Joe: Yes …
[00:54:45] OG: shampoo. Like, you know, you just get it, and it just piles up, and you go, “I’ll use that for my… That’ll be my travel stuff.” And then you just travel and get more of it. I actually kind of worked through that this year of not buying any new…
[00:54:58] OG: I don’t know if you guys can tell this or not. I’ve not bought any new soap or shampoo- Oh, we can
[00:55:02] Doug: tell …
[00:55:02] OG: all, all year.
[00:55:03] Doug: Oh, we can tell. It’s a small card table.
[00:55:05] Joe: That’s why we put OG at the long end of the table.
[00:55:07] OG: I took, I took the joke right out from underneath you. This one I actually do like because, you know, you probably have a drawer full of, like, these little half bottles of shampoo and stuff.
[00:55:16] OG: Just burn through them. Get them gone.
[00:55:17] Doug: That’s what Kiki’s gonna do. Here are the things that Kiki will not cut: anything health-related, medical appointments, organic produce, uh, family health items, vitamins and supplements, pet care, vet visits, vaccinations, et cetera, safety items, fire extinguishers and blankets, housing maintenance, car maintenance Kiki’s always been frugal, proud Gen X and raised that way, and it’s been a longstanding game to see how much I can either go without or get the lowest price.
[00:55:48] Doug: Am a value conscious person. Thank you for sharing your knowledge with all of us. This is Kiki saying this to us. Thank you for sharing your knowledge with all of us, especially Doug. Uh, and please also thank… It’s, it’s right there in black and white. I swear to
[00:56:01] Joe: God, no.
[00:56:04] Doug: And also thank OG neighbor Doug and his fin turn, Paula, Doc G, Len Penzo, and the rotating cast of characters who provide interesting perspectives on personal finance.
[00:56:14] Doug: Gig ’em, Kiki.
[00:56:17] Joe: Kiki, back at ya. By the way, thanks for the note, and I love the personal accountability of hit and reply on the 201 email, uh, or in just writing to us. I, I think that putting it out there in the universe, writing it down, is a great way to stay on top of what’s important to you. And, you know, at first you lost me with some of the, you know, “I’m, I’m gonna cut the fun out of my life unless it’s on discount,” but I, I gotta say, I do like the gamification of that.
[00:56:42] Joe: I think gamifying that is super. And in lean times in my life, if I thought about how miserable it was that I could not go to a restaurant or I was, uh, was cutting back on everything, it stunk. But when I turned it into a game, you know… Uh, what, what, what’s that game? The floor is lava, right? When I turned it into a game, it made it much, much better.
[00:57:07] Joe: So thanks for the note, Kiki. I also love hearing from our stackers making big life changes. If you’re somebody who wants to make, uh, some significant life changes and you, you want the surround sound, there’s not just the podcast. We have a YouTube channel. If you want to dive further into not just this week’s OG and Anna segment, but all the segments, this is on the Stacking Benjamins YouTube channel, along with our great lessons from our mentor interviews.
[00:57:36] Joe: We have a great Start Here section if you’re introducing people to Stacking Benjamins. I think that that’s a great, uh, way to introduce them to the channel is to go there. That’s at our YouTube channel, youtube.com/stackingbenjamins. Also, we have meetup groups around the country, so whether you’re in Boston, Seattle, the Twin Cities, Mankato, Tucson, and, uh, we’ve got a couple more coming on board that I can’t wait to tell you about.
[00:58:03] Joe: Stackingbenjamins.com/bad. That’s Benjamins After Dark. Those are our meetup groups. It’s always great to meet other stackers, like-minded people in person. We’ll have all of our links to everything we talked about, of course, that, the 201 and more at stackingbenjamins.com. We have a lot of takeaways. I hope you wrote down a lot of takeaways and a lot of things that you may need to share with people who are in the situation of maybe retiring early, and some steps to begin thinking logically along that process.
[00:58:30] Joe: And even if you’re not- planning on retire early. W- I think the big lesson today is that sometimes it, it finds you. But Doug, you actually have the big three lessons we should learn today. What are those, man?
[00:58:42] Doug: I got the real ones, Joe. First, take some advice from our featured topic. Retirement doesn’t always happen the way we envision it.
[00:58:51] Doug: Building on-ramps early to retirement so you can smooth out the transition will pay for itself quickly, even if retirement happens as you prefer. Second, is company ownership part of your income stream? Diversification is your friend, so knowing your options and the tax implications are only table stakes before you can begin playing the game of using this equity effectively.
[00:59:17] Doug: But the big lesson, if you’re talking to Joe’s mom about early retirement, mention a party. She’ll get cooking immediately, and then, you know, we all win. This show is the property of SP Podcast, LLC, copyright 2026, and is created by Joe Saul-Sehy. You’ll find out about our awesome team at stackingbenjamins.com, along with the show notes and how you can find us on YouTube and all the usual social media spots.
[00:59:45] Doug: 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 see you next time back here at the Stacking Benjamins show.
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