“How do I know it’s time to fire my advisor?” That question came up over and over at a recent retreat, enough that Joe knew it needed its own episode. Today he and OG walk through five real, specific red flags, not vague warnings about fees, but concrete signs that your advisor might be coasting, out of their depth, or simply not built for where your life is headed. If you’ve ever sat in a meeting with your advisor and wondered whether you’re getting real value or just really good small talk, this one’s for you.
What You’ll Walk Away With
- Why an advisor who knows your portfolio better than they know your actual life is a warning sign, not a compliment
- The real reason a “free” advisor should make you more suspicious, not less
- Why an advisor working with literally anyone, instead of a defined type of client, often means shallower expertise
- How to tell the difference between a collaborative advisor relationship and one where you’re quietly doing all the driving
- Why outgrowing your advisor isn’t always about more money, sometimes it’s about more complexity, and that’s worth a real conversation
- A simple question to ask about fees that costs you nothing and might save you real money
- The single clearest red flag of all: an advisor who leads with products instead of questions
Why This Matters Now
Most people have no natural way to judge whether their financial advice is actually good, since the whole reason you hired someone was that you didn’t have the expertise to evaluate it yourself in the first place. That’s not a flaw in you, it’s exactly why concrete, observable signs matter more than a vague gut feeling. Knowing what a good advisor relationship actually looks like, real collaboration, a defined specialty, clear communication about fees and process, gives you a way to check in on that relationship without needing a finance degree to do it.
From the Basement
An Earth, Wind & Fire trivia detour uncovers the real, long-hidden meaning behind “the 21st night of September,” and a listener question from someone getting her first-ever 401k at 50 sparks a genuinely useful conversation about target-date funds, Roth versus pre-tax decisions, and the often-overlooked Rule of 55.
Resources Mentioned
Yell Down the Stairs — submit a question for a future OG and Anna episode
Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
Stacking Benjamins Benjamins After Dark meetups — local in-person Stacker meetup groups
OG & Anna
OG and Anna tackle listener questions about the tricky line between saving enough and actually enjoying your money. They discuss why a strong net worth doesn’t always feel wealthy, the danger of waiting for the “perfect” time to invest, what should change financially in your 50s, and how to know when you’ve earned permission to spend a little more.
If you have a question for OG & Anna, send it to og@stackingbenjamins.com.
Doug’s Trivia
- What was the significance of September 21st in Earth, Wind & Fire’s song “September”?
Have a question for the show?
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Join Us Wednesday
Tune in on Wednesday when we explore the long, sordid history of bonds and what corporate bonds, Treasury bonds, short-term bonds, and long-term bonds may be telling us about the future.
Written by: Kevin Bailey
Miss our last show? Listen here: Beyond Index Funds. Are You Ready to Pick Stocks? (SB1899) | Stacking Benjamins
Episode transcript
Letters: [00:00:00] What a filthy job Could be worse How? Could be raining
Doug: Live from Joe’s mom’s basement, it’s The Stacking Benjamins Show
Joe’s mom’s neighbor, Doug, and we’ve talked a lot about having good help in your corner, but when do you know that the help in your corner isn’t really helping? That’s right. Today, Joe and OG tackle their top five clues that your advisor might not be the best fit.
And if it’s Monday, you know what that means. Ana and OG are back with some money basics. What are they covering? You’ll have to listen to find out. But I won’t leave you hanging on this. Yes, there will be another dose of my incredible shareable [00:01:00] trivia today. You’ll want a slice, and that’s halfway through today’s show.
And now, two guys who can never stop halfway when it comes to a bowl of ice cream, it’s Joe and O-G-G-G.
Joe: Have you ever tried that, Doug? You ever tried to, like, have some self-control and stop halfway through? You’re like, “Maybe this is too much.”
Doug: I’m not even a huge dessert guy. In fact, I don’t really like desserts that much. I’ll always have another steak and potato, but you can’t walk away from ice c- You can’t
like, if it’s in the bowl, it’s, it’s as good as finished, so you just finish that. Yeah, you’ve already
Joe: claimed it anyway. Absolutely. Nobody’s gonna eat
Doug: that after
Joe: it’s been in your bowl. You can’t put it back.
Doug: Actually, that’s my theory on everything in the cupboard. I bought it. It’s eventually going in my stomach.
It might all, might as well all go in there now.
Joe: It’s now got my name… It’s gonna go there sooner or later.
Doug: It doesn’t even have to be in the bowl. It can just still be in the box in the cupboard.
Joe: Who needs a fork? Nobody. Welcome to The Etiquette Show. I’m Joe [00:02:00] Saul-Sehy, talking etiquette and pantry management today.
Actually, we got a great show for you. So happy that you’re here with us. Sit back and relax. Grab something to take notes because today, my other good friend across the card table, OG, and I, we’re talking about top five signs your advisor might not be all you would hope. How are you, OG?
OG: Excited to be here.
Joe: I’m excited that you’re here, too, because I was just at a Camp FI. For people who don’t know what Camp FI is, it’s a wonderful retreat with… We have 50 people out at this retreat center in Minnesota, and you spend the weekend talking about, “What do I really value? Am I going toward that stuff? Am I not going toward it?”
And a big question I got all weekend was this one: “How do I know it’s time to fire my advisor?” Or, “How do I know that it’s time to really lean in? My advisor’s great, and I should probably be, you know, leaning on them more than I am.” We’re gonna talk about that today, so super happy that you’re all here with us.
We have a couple sponsors who help us keep on keeping on. We’re gonna hear from a couple now and a couple [00:03:00] in the middle of Doug’s trivia at the halfway point of today’s show. We’re gonna hear from them, and then OG and I diving into our top five signs your advisor might not be great. I’m loving the early emails I’m getting about the Field Kit, and for those of you that have already tried it, you know what I’m talking about.
You can get your budget in order, your net worth, your privacy, your credit. It’s all in one place, stackingbenjamins.com/fieldkit. And by the way, Field Kit users and people wondering how the Field Kit works, we’re gonna be doing some webinars in the next couple weeks, so if you get the 201 newsletter, you’ll get an email about the Field Kit.
Stackingbenjamins.com/201 tells you when we are going live on YouTube with a webinar so you can ask all your Field Kit questions. That’s coming up, stackingbenjamins.com/201.
You know, it’s so hard, OG, when we get [00:04:00] the question, “Uh, h- how do I know that my advisor’s really a good advisor, like I’m really getting quality advice?” And it’s hard, right? Because there’s a certain level of knowledge that you have to have about financial planning in general to know that, okay, th- th- this is a good thing.
But if you’re somebody just really starting out and you have this person in your corner, and they’re telling you about some exotic strategy, and you’re not really sure how it works. You’re like, “What do I… Ugh, what do I know?” So I think this is a really important topic for a lot of people.
OG: Yeah. I, I’ll be interested to see how we, uh, get through this conversation ’cause I’ve got a few that popped into my mind.
I’m kinda c- curious to hear what you experienced when you were up north.
Joe: I wanna talk about one, OG, though, that didn’t make my list, and maybe it did make your list. The way the advisor charges did not make my list, and I think that’s gonna surprise a lot of people, and that is simply because there are some advisors who only get paid commissions.
That is the thing that when you [00:05:00] go onto online forums, people are like, “Do not hire somebody that just does commissions.” I know some of these people, OG, who are just fantastic advisors. They actually sell stuff when it’s needed. They don’t sell stuff when it’s not needed. So for me, it’s very difficult to isolate a good advisor based on their fee schedule.
OG: Well, the problem with anything money related is, what’s the phrase? Show me the compensation and I’ll show you the, uh, the bias or something like that.
Doug: You totally made that up.
OG: When you introduce a compensation structure that is deferred based on products and not complexity, then you introduce automatic biases.
There’s no way for a normal human being to say that they don’t have a bias if you’ve got option A and option B and they’re markedly similar, but option A pays you more money than option B does, that you’re not gonna just kind of maybe [00:06:00] tilt a little bit toward option A, even if it’s a 51/49% tilt. It’s just not possible as a human to do that, so, or not do that I should say.
Joe: Yeah, and that’s 100% why I brought it up because I do think it’s important to know how the advisor is paid. Yeah. But before we got into our list, and people are like, “How come you didn’t put how they’re paid?” It is a bias I wanna know. I just wanted a list of five ways that I know my advisor’s probably not great, and that isn’t one.
It certainly could be one, but it’s not always one, so it didn’t make my list. Let’s do this. Steve’s got our British guy ready. Uh, let’s do number five.
Letters: Number five.
Joe: All right, OG, you wanna go first with your number five?
OG: Uh, I can, sure. Uh, so my first one is, uh, that they know your portfolio better than they know who you are as a person.
Joe: Mm.
OG: So your advisor can recite facts and figures about alpha and standard deviation and what the performance is [00:07:00] and, you know, the fund manager and the tenure and all this great stuff about your investment portfolio, but doesn’t really know or hasn’t paid attention to the fact that, um, you’re really stressed about the fact that you gotta take care of mom all of a sudden, and that’s a thing.
But hold on, let me tell you how great your portfolio’s doing. I think, you know, portfolio serves the plan. Your investments serve, you know, the overall financial plan, and there’s a time and a place to be talking about those numbers, but if that’s the vast majority of your conversation- Yeah. Michaela’s not impressed, for those of you who get that meme reference.
Doug: I d- I don’t. Do you, Doug? Vaguely.
OG: Don’t know the Michaela’s not impressed meme? Ugh.
Doug: It’s a couple years old, isn’t it?
OG: Oh, a couple. Probably 15 now. It goes back to the, uh, Summer Olympics when McKayla Maroney did an amazing job at whatever thing she was doing in the gymnastics for the U- Team USA, and then didn’t score as high as someone else, despite [00:08:00] the fact that it was cl- like, everybody and their brother was like, “Oh, that’s way better than this other person.”
And she’s got this, like, pouty face where she’s just, like, got her arms crossed, and her lips are pursed and, like, off to the side, and it’s just a snapshot of- Yeah … like that. I do remember that
Joe: now. And it’s a- Just not impressed with the judges …
OG: Michaela’s not impressed.
Joe: Yeah.
OG: Guess it was a old one.
Joe: My talk at Camp Fi was about what are we really solving for, and a lot of the professors online will tell you, “Well, duh, you’re obviously solving for more money.”
And yet a statistic that I uncovered recently was that 40% of millionaires are still afraid they’re gonna run out of money. 40%. And the study also went on to show that by adding more money to the pile, it didn’t make that fear go away. What made the fear go away was knowing what you were chasing. And so to your point, if your advisor knows what the portfolio’s up to and all the intricacies of portfolio, but they don’t know what you’re chasing It’s still gonna cause a lot of consternation because you’re not sure what the money’s for.
OG: Yeah. Yep.
Joe: My number [00:09:00] five is, and, and I try to put these in order from most important to the least. You can certainly have a decent advisor who’s a generalist, but I think that a generalist is a first sign that you could probably do better. Somebody who just works with anybody, they have some solid criteria, which is that you can breathe.
If you can breathe, they’re gonna be a client for them. I really want an advisor who works with people like me. I want them to… You know, for me, it’d be somebody who is self-employed, somebody who’s in their 50s. Like, I want some criteria that makes sure-
OG: Upper 50s …
Joe: that they’re, m- you know, middle 50s, middle-ish 50s.
OG: Okay.
Joe: I truly, I truly want somebody who spends their time doing the thing. I don’t… I, you know, and no offense to generalists, like, one of my best friends happens to be my doctor. If I need heart surgery, I’m not going to Troy for that. I’m going to Troy when I have a cold, ’cause he handles everything, but man, I, I want a [00:10:00] heart surgeon to do the heart surgery, so.
OG: And Troy, in your example, and then Troy probably knows a really good heart surgeon. So you might go to him and say, “Hey, you know what? I’ve got this real big complication,” and because he’s a great advisor, he would say, “This isn’t my specialty, but I know a guy, I know a gal who I should send you. In fact, let me make the introduction, and make sure you get great care along the way.”
Joe: And that’s the sign of a great advisor to me. I think
OG: so, yeah.
Joe: Yeah, not that they know everything, but they are a hub of great information. Yeah. And, and if, and if they… I don’t like the one-stop shop where the advisor tells me, “Hey, in-house I can do this, I can do this, I can do…” You know, a few things, fine.
But I really, really want somebody who is connected in my community and connect me to the right people to do the thing for me. Yeah, but that’s number five. I really look askance when I’ve got somebody who just works with anybody. Did you just…
Doug: Hold on. Did you just say
OG: askance? Dropping a line from Hamilton.
Joe: What’s that?
Doug: I look askance? [00:11:00] Are we that podcast now?
OG: He’s quoting lines from Hamilton.
Joe: I’ve got good words. I’ve got good words. There’s a lot of good words in this brain. Somebody’s
OG: into show tunes.
Joe: Maybe just ’cause I was singing show tunes just before we hit record, you know.
OG: I get it.
Doug: Number four.
Joe: Number four.
Are we gonna do the snake draft thing, OG, where we go- Sure … back and forth? Are we gonna- Hit it. Okay. My number four, a big sign for me that your advisor might not be th- uh, best, and again, this one also is number four on my list, because it could be a good advisor, but it w- there’s a lot of yellow, orange, and red flags here.
If your advisor’s affiliated with a product company Hmm. There’s probably a good chance that the sales training that they get, and it is sales training, the sales training there they, they have is going to align whatever your problem is with products that that company sells. And I mentioned that, you know, the fee structure didn’t hit my [00:12:00] top five.
But man, when somebody tells me that they have an advisor who works for an insurance company, I immediately some, maybe not red flags, but deep, deep yellow into orange flags start to go off.
OG: Yeah. This isn’t on my list, but, um, because I was thinking more big picture than this. But I, I would, I would, again, back to the incentive thing, whether it’s because of their training or it’s because of that’s just where their knowledge level is, or if it’s literally where their bread is buttered from.
When everything… You know, what’s the phrase? When all you’ve got’s a hammer, everything’s a nail. We’ve been on record over many years of the show saying there aren’t bad products, there’s just bad applications of products.
Joe: Yeah.
OG: And, you know, you can look at a product and go like, “This one’s better than that one in that genre.”
Sure. And I agree that there’s some of those. But I’m saying, like, just generically speaking, whole life insurance, annuity, [00:13:00] l- term, whatever, mutual funds. It’s not that the product is bad, it’s the application of the product usually is the not so good thing. I’m dealing with something right now with a client, just happened to bring it up.
His mom had passed away and had two annuities. One was an IRA, one was a non-IRA. But basically led the family to believe that they are required to distribute the non-IRA over 10 years. And, “Oh, by the way, we just signed this paperwork, and, you know, we’ll give you-” Oh, no. “… this money over 10 years.” And because th- the traditional IRA, that is the case.
But he also led the people to believe that it has to stay with their company to do that. I said, “Well, it’s an IRA, you can have that wherever you want.” “No, no, no, he said that it’s gotta stay with them to get the 10-year deal, otherwise I have to take it all out right now.” It’s like, not true. Slimy AF is what I would say to that Ugh,
bumper: that’s horrible
OG: Over, by the way, not over like a $200 million annuity contract either, where this dude’s gonna make some money.
Like [00:14:00] literally a $70,000 account that is a $3,000 commission probably. I get it. It’s not zero. He’s probably putting some food on the table with it, but you’re hosing five family members for the next 10 years for three grand? Come on, man. So not impressed. I know we weren’t gonna talk about pay, but this is a product situation
Joe: That’s 100% a product situation, and when somebody works for a product company, I think the, the chance that that might come up.
Let’s put it this way- Yeah … Doug, I may look askance at that. I may look askance.
OG: Nope. Can’t, definitely can’t use it twice.
Joe: I had to. It’s called a
OG: callback. All right. My number four is you’re the project manager of your own financial life, and what I mean by that is you’re the one that’s sending emails going, “Should we be doing Roth conversions?
Hey, do you need to look at my estate planning documents? Can I get an analysis on my kids’ college funding and where we’re at on this?” Uh, every so often, if there’s some kind of one-off thing that you haven’t seen in a [00:15:00] while from your advisor or some, some specific analysis that you’re looking for, I think it’s totally fine.
But if you’re finding yourself that you’re preemptively bringing all of these topics up one right after another, and it kinda dovetails into another one that I had, but I think I’m just gonna combine them, which is if this sounds like the same meeting over and over and over again You know, and there’s not like a structure to either contemporaneous stuff that’s going on or, or a structure to, you know, your financial life.
Um, eh, it’s getting a little stale.
Joe: You know, I certainly want it to be a collaborative thing. I wanna be able to bring information to the, the meeting as a client. I also wanna be able to say, “Hey, I was listening to this podcast and I heard about this. Do you think this affects me?” And have the advisor opine about that one.
Mm-hmm.
Doug: Oh, he’s on it today.
Joe: I’m on fi- in fuego. I, I want them to let me know if that applies to me or not, so [00:16:00] I really wanna be involved. But there is a difference between collaborative and I’m driving the bus.
OG: Yeah.
Joe: The advisor does this every day. If I’m telling the heart surgeon, “Hey, I’m drawing the X on my chest,” like-
OG: Cut here, dot, dash, dash, dash, dash.
You’re like, “Doctor, uh,” uh, what’s, who’s the doctor in The Simpsons? “1-800-DOCTOR. The B is for bargain.”
Joe: I don’t … There was- “
OG: I do heart surgery for 129.95.”
Joe: Three words that don’t go together, discount and heart surgery. Yes. Do not- Yes … do not, three words I want together. Oh, that’s a great one.
Letters: Number three.
OG: I kind of pieced two together, but I was smart enough to bring a bonus one just in case I needed it.
So, um, I’m gonna say number three is your other professional CPA, attorney, insurance gal if you got it, nobody knows anybody. Nobody knows what’s going on. Y- either you don’t [00:17:00] want people to be engaged, which is a you thing, or it’s never been prompted of like, how do I interface with these other professionals that you have so that we can all be singing off the same song sheet?
One of the things you said, Joe, was, “I don’t want a one-stop shop.” I will say that having a one-stop shop where one person is like the head cook, bottle washer, and, you know, Maître D all at the same time is probably a bad idea. But if the firm itself can support Different areas of your financial life with professionals and all those things, I do think it’s actually kind of a good thing.
And then, you know, like we said before, being able to interface with these other professionals. We don’t have a law firm on, you know, a lawyer on staff. It’s not legal in the United States for non-lawyers to own law firms. So even if I wanted to have a lawyer on staff-
Joe: Couldn’t
OG: do it … he or she would have to be affiliated with a law firm that we’re not…
You know, it’s just not, you just can’t do it. [00:18:00] But we have a great relationship with a law firm that if there’s an estate planning need, or frankly any business/financial, you know, need as it relates to l- uh, uh, lawyering. Is that the right word? The-
Joe: I think it’s be
OG: lawyer. Lawying? Lawying.
Doug: Lawying. Litigating.
OG: Lit- lit- yes. Well, they wouldn’t, they wouldn’t do litigation.
Joe: Engaging in
OG: litigiousness. Yes. If one were looking askance.
Doug: Okay, we went too
OG: far. Is that… It’s not right.
Doug: We just did it. Went, went too far.
OG: We’ve got a great relationship, and we would have that resource for you. I, I always tell people, “We’re not gonna bring you problems with your financial life that we also don’t bring you solutions to.”
And that solution may not be something that we can directly do for you, but it’s, but it’s carried down the field as far as we can take it. You know, your life insurance sucks, Joe. Yeah. Period. You’re like, “Okay, so what do I do with that? Like, how much do I need? Where do I go? How much is it gonna cost?” I wanna say, “Joe, the life insurance isn’t what you, the number that you had needed.
You need to have 20-year term. Let me tell you how we got there in a $2 million policy. [00:19:00] Here’s, here’s my math. Also, I shopped 50 carriers. I found these three that I think are the best for you. We’ve taken the liberty to fill out most of the paperwork. The questions I don’t know are these health-related ones.
Here’s the DocuSign. Fill this out, hit submit, and then let us know how the process goes.” Same thing with the lawying.
Joe: When you have different advisors and their advice isn’t dovetailing, I think that’s a sign something’s wrong, when, when it’s not a collaborative effort between your advisors.
OG: You know, the other thing that I would say about this too, which is interesting, is not always are those people always gonna agree.
Joe: Right. It’s okay that they don’t agree-
OG: Yeah …
Joe: but you want them to be collaborative.
OG: Yes, 100%. We- we’ve got another circumstance right now where it’s like, well, I don’t agree with this, but also I’m not a professional. I’m not the one that’s signing this deal So here’s my take on it. Here’s that person’s take on it, Mr.
and Mrs. Client.
Joe: That’s actually great that they don’t agree. I think it’s- Sometimes. Gets a little extra work. I mean, once again, as long as it’s [00:20:00] collaborative and you can see- Yeah … and I get these different points of view, or they do agree, OG, and they go, “I like where they’re going, but here’s the Achilles heel,” you know?
OG: Yeah. Have we considered this as an alternative or, or whatever the case may be? Yeah.
Joe: Yeah. My number three, and I’m only bringing this up because I’ve, I’ve seen it way too much, and I know there’s people listening who are like, “I love my advisor. They don’t charge anything.” If your advisor does not charge anything, I can assure you they’re not working with you because they’re nice.
They’re not working with you because they’re some sort of a saint. They are getting paid, and you don’t know how they’re getting paid. It is scary the number of times I run into people that are like, “Oh, yeah, I don’t pay my advisor. No, I got this great advisor. They recommend stuff, and yeah, they don’t get paid.”
Are you kidding
OG: me? No. I had a sales leader, this reminds me of something a long time ago. I had this sales leader at Ameriprise, Joe you know who it is, where this would be a common, like, “Why do I have to pay you?” [00:21:00] Was the common objection. Now, remember, when you and I were doing this in the late ’90s, the idea of paying for advice was completely foreign.
Joe: Fairly new.
OG: I mean- To so many people … it, it, there was not a thing, and Ameriprise was kind of at the forefront of that of saying, “Hey, we’re gonna charge for financial planning advice. We’re also gonna manufacture and create a bunch of products,” which is one thing we talked about, you know, is not so great, “but we’re gonna charge for advice.”
And the sales leader would say, “Okay, Mr. and Mrs. Client, so you know, you’ve got a guy, you got a gal that’s gonna do this, this, this, this, this, this.” He’d like bullet point list out, like, the whole process of financial planning. And if you can remember those old offices with the whiteboards and- Yes … you know, the conference tables, and you’d have your little pitch that you’d write on the board, and all that sort of stuff.
And he would, he would talk, talk with his hands, and he’s got the marker in his hands, and he would go, “So we’re gonna do this, this, this. This, this, this,” all for less than the cost of this marker.
Joe: Oh, my God.
OG: And he would like slam it right down- Oh … in the middle of the table and like stand it up there. And you could just see the, like, it wash over them.
You know, it’s a little [00:22:00] slimy sales stuff, you know what I mean? Like- That there
Doug: is classy.
OG: It’s maybe a little, a little more aggressive than things are these days. But it drove the point home, and I think that’s the point that you’re making with this, which is, unless they are like literally billionaires, and frankly, I don’t know too many wildly benevolent billionaires anyway, or altruistic ones.
So it’s like, okay, unless they’re independently wealthy enough to, like, pick you out of a hat and say, “You know what? For you, I’m gonna do it for free.” There is that. We do pro bono work. Mother
Joe: Teresa of financial planning.
OG: Yeah. Well, we do do pro bono work from time to time, and we think that’s part of our role, but it’s not what supports the business, right?
Like, we still have to… You know, all the people that work for me want to get paid. All the vendors that I use, they also want contracts, and they want to get paid for their services and all this other sort of stuff, so all for less than the cost of this marker. Oh, my God.
Doug: I’m using, I’m totally using that somewhere.
OG: You’re gonna totally use that somewhere, I know. I
Doug: love it.
Joe: Yeah. I’ll tell you what, Doug, not only are you getting this for free, I’m throwing in [00:23:00] Michael Bolton tickets.
OG: It’s like the time that my mom went down to the, uh, campground sales place because it was, uh, they were giving away a free car. And I said, “Did you win the free car?” She goes, “No, we were really close though.” The key fit in the door, it just didn’t turn. I was like, “Oh, okay”
Joe: It’s so weird. Ev- everybody there was really close.
OG: And then she’s like, “In other news, we now have a campground membership.” “You guys wanna come camping, right?” I’m like, “Mom,
what the ?” “When was the last time you went camping?” She’s like, “72, s- 60- 68, I remember. I just thought it might be fun.” I’m like, “Do you have a camper? Do you know anything about camping? Can you start a fire?” “No, no, I don’t. I thought you guys might want to. We bought it for the kids, really.” Like, okay.
Doug: How long was she a gold tier member of this campground?
OG: Yeah, no kidding. I don’t even remember. It was, uh, it was-
Doug: Did you go camping? [00:24:00]
OG: Never. No one went, ever. No one ever went. But she almost did win the car.
Joe: Very close. There we go. Very, very close. That was my number three. Have you done your number three?
OG: Uh, yeah, maybe.
Joe: I think so.
OG: One, two, three. Yes. Yeah, you’re on number two.
Joe: All right, uh, Steve, play number two. Number
Letters: two.
Joe: You know, I get that some offices are one person only, and I think they can give good advice if they are a one-person office, but what I really want from an advisor is I want their brain power. I don’t want them answering the phones. I don’t want them helping filling out paperwork that an admin can do.
So it doesn’t mean they’re a bad, they’re, they give bad advice, OG. It just means I think I can do a lot better if the person has support staff. I really want that person focusing on the things that matter to most people. I don’t want the doctor answering the phone. I don’t want the doctor prepping people for the surgery.
I want them doing as many surgeries as [00:25:00] they possibly can. So I think it’s a flag, and I think it’s a big flag that my advice could be better if they, if she does it all herself. If, you know, going to see this woman and she’s doing all this stuff, uh, that’s my number two is an advisor without staff.
OG: Hmm.
Okay. I think you’ll get some pushback on that one. Um, I don’t know. See, I thought you were gonna go down, like, some continuity type of, type of route of, you know, “It’s great if I got one gal, you know, helping me out, but what if something happens and all that knowledge is locked up there?” Oh, I
Joe: like that too.
I love the fact that there’s a practice continuity, especially if the advisor’s older. Remember how, you know, i- in my career, some people didn’t wanna work with a younger advisor, they wanted the older advisor? Well, it’s great you’re getting somebody who’s been in the trenches, but, well, what do you do when they retire?
Yeah. If you wanna have a relationship with a firm, you really want the older person and the younger person coming in behind them.
OG: Yeah.
Doug: You need [00:26:00] somebody with all their heart valves on staff.
Joe: Yeah.
OG: You want gray hair, no hair, and full hair. Like, you just, you want the, like-
Joe: Mm-hmm …
OG: sequence of…
Joe: The full, full spectrum.
OG: Or as Doug calls it, the full Monty.
Joe: I worked early on by myself, and I know the amount of time I was able to devote to- Yeah … uh, complex good questions, and it doesn’t mean, you know, new advisors are bad. Everybody’s gotta start somewhere. But man, when I hire somebody, I really want to call Tina to handle my scheduling question because I wanna know that there’s a complex Roth IRA problem that, you know, Tina’s boss is actually solving.
OG: Yeah, we call this unique ability teamwork, borrowed from Strategic Coach, and it’s really get a bunch of people who are really good at a, at their specific thing and empower them to do their specific thing all the time really well. If you can do that, then you’re developing a really cool team.
Joe: And a question before we get to yours, OG, ’cause people are always like, “So how do I know?”
Ask them. Ask them [00:27:00] about their team. Ask them about the roles. Ask them about when I call in.
OG: Call the phone number and see who answers.
Joe: That’s right. You know? Yeah, but I do wanna know more granularly, like if I ha- Yeah … you know, who does what. What are the, what does the breakup in roles in your firm? And you’ll find out really quick, uh, what- Yeah
their answer is.
OG: Yeah. That one’s pretty good. All right. My number two is a little bit of a play on what you said maybe for your number three, which is, you know, some products and that sort of thing. I, I said you just don’t know what you’re paying, or more specifically, what you’re getting for it. So kind of in line with what you talked about there.
It said, you know, certainly not like fees are bad because advice is worth, you know, whatever it’s worth. You know, there’s a shelf life to that value. I get that. You save $100,000 on a tax problem, I think sometimes advisors look at that and go, “Hoo, I’m good for, like, the next 15 years. I don’t have to do anything.
You know, Joe, he’s gonna remember that I, you know, I hit a home run on the first pitch way back in aught seven.” You know, and it’s like, no, you still have [00:28:00] to provide value, you know, year after year, but it’s, but it’s not l- a linear type of value. So if you don’t know what you’re paying or what the process is or what the experience is that you’re supposed to get, I think the advisor may be doing a bad job of explaining that to you or may be doing a bad job of delivering it.
But I think it’s worth a conversation of, like, what is this, what is this client experience supposed to look like year after year?
Joe: Yeah. Either way, I mean, think about what their role is, OG. It’s to be an advisor. And if it, if you’re getting cloudy stuff from your advisor, your, your advisor’s job is to make things cloudier.
It’s to clarify. It’s to help- Mm-hmm … you be able to crystallize. “You know what, OG? I don’t think this is the issue that you think it is. Here’s the real issue.” “Oh, thank you.” You know, get really crystal clear. Uh, somebody to challenge your thinking, and if you’re not really sure, if it feels like, you know, smoke and mirrors, dogs and ponies, I got no idea what’s coming next, well, uh, I think there’s, there’s some problems there.
All right, we’re at it. Time for the drum roll. You gonna go back to [00:29:00] the old days, OG, and do the drum roll? Do the drum roll. Come on.
OG: I have no recollection of that, Senator.
Joe: Yeah. Look at what happens, Doug.
Doug: That’s ’cause he’s getting older. He’s losing his memory a little bit. It’s what happens. There it is.
OG: A little bit of the dexterity maybe, much to Doug’s mom’s
Doug: chagrin.
It’s been a while since we heard a good one of those.
OG: Well, for the people that know what, know what Joe’s talking about, then that’s a, that’s a triple entendre.
Joe: Number one.
OG: All right, number one for me is, uh, complexity. You’ve maybe just outgrown them. You’re… You know, you started working with a firm or with a, an advisor.
You were 30 years old, and you saved a few bucks, and, you know, life was good, and now you’re the CEO of a big organization, and you just had a big stock sale, and, you know, you’re selling your business for $10 million or $5 million or… And maybe that’s a little more complicated than what you think that person should handle.
And, [00:30:00] uh, this one’s really tough I think because outgrowing somebody because of, uh, complexity is different than outgrowing them because of relationship. You know, and it’s like, “Yeah, I’ve been with, I- I’ve been with George for 20 years. Like, he’s my guy.” It’s like, yes. Yeah. But if their specialty, back to what we were talking about before, is people that have $150,000 saved and are saving, you know, 10 grand a year in their brokerage account, nothing wrong with that.
It’s a perfectly fine specialty to be in. But if all of a sudden you’re the unicorn that, you know, you’re selling your HVAC company to PE for $17 million, I’m not sure that George is the guy, you know? That might be a little out of bounds.
Joe: This was a big aha for me way, way, way back in the day. In the early years of the podcast, we interviewed Tony Stubblebine, who is- Mm-hmm
one of the creators of an organization called Coach.me. They’re still around today. Yeah. They provide all kinds of coaching services. And Tony’s big point was you don’t need… It isn’t a life sentence with this person. It’s, “I have this specific need. [00:31:00] I plug in the person who’s really good at it.” And as an example, I hired Coach.me to do Inbox Zero once.
I hired him, I got to Inbox Zero, I learned what it was. A month later, OJ, he was gone. He did the job I needed.
OG: Yeah, I mean, my, yeah, my hope here is, is that over your lifetime, uh, you know, relationship with this team, they are growing in the capabilities and resources as you’re growing in capabilities and resources.
You know, so you’re growing with them. The other thing that’s interesting is y- the inverse of this can happen also. So speaking from an advisor perspective, if the advisor is growing, right, and, and we want, we as humans want constantly more fascinating and motivating things and projects to work on, right?
Like, we want to be challenged. It’s just like any other job. You, y- y- you want to grow in your career. And so sometimes you grow in your career faster than the people around you grow. And then as an advisor, you evaluate and go, “Geez, I don’t know that I’m providing the best support I can for this [00:32:00] group of people anymore, because we now are really good at this group of people.
We’re not really specializing in this group anymore.”
Joe: And even though it’s painful maybe in the moment- Oh, it’s ridiculous … that’s a great, it is a great advisor who admits that, though. Says, “I love you as people. I’m not your person.”
OG: Yeah. So it goes both ways, right, is what I, I guess what I’m saying, is that there can be a circumstance where an advisor’s career growth and practice and, like, all the stuff that they’re working on is growing faster than you are, and that might happen.
And they might say, “Hey, look, I can’t work with you anymore because the types of work that I’m doing is this, not this.” And it doesn’t have to be, like, more upscale. It could just be like, “All of a sudden I found out that I’m really good with working with welders, and you’re not a welder. I just want to lean into welders because I love ’em, and I’m real- I’m the best at welders, and you’re an eye doctor, so you need to go find eye doctors,” you know?
So it could be something like that. But if you have something like some sort of mega change, you go from making 100 grand a year and then grandma and grandpa die and you get $32 million, [00:33:00] you know, it might be worth a conversation anyway.
Doug: My takeaway from that was apparently there’s a welder kink. Like that’s a thing.
Joe: If your advisor’s a welder kink, maybe it’s time to get rid of him.
OG: No.
Joe: Father will talk about his
Doug: welding. People are into welders?
OG: Have you seen those cool hats that they wear?
Joe: They do wear cool hats.
Doug: And nothing else.
OG: And they do it like with their head. They go like that, and it comes down.
Joe: Comes down.
Yeah. The clunk.
OG: Yeah.
Joe: I think just learning that move is part of what being an apprentice welder is all about. I
OG: know. I just did it for the first time, and it hurt my neck. I was just like- See? … oh, my God.
Joe: My number one is a very easy flag, an incredibly easy flag, and it’s this. If your advisor leads with product and not questions about process, really it’s very closely related to your number five, OG.
Mm-hmm. If they are talking products, they’re not talking process and questions, here’s how we’re gonna solve problems. Instead they’re just plugging in solutions, and they haven’t asked you [00:34:00] questions, they haven’t introduced a process, that’s the 100% the wrong advisor. 100% the wrong person. All right, those are our five.
What did we miss, Stackers? You can share your top five with us in the basement, which is our Facebook group. And to get there, you go to stackingbenjamins.com/basement. That’s the quick way to join a lot of our other Stackers, or our meetup groups around the country may be talking about this, so you can talk to people face-to-face.
I love it when our meetup groups get together, and you can find them at stackingbenjamins.com/bad, which is Benjamins After Dark, the name of our meetup groups. I think there’s a lot of ways to find out if your advisor is good or bad, and I think we tackled a bunch of those today. So I hope we helped a lot of people.
All right, time for your favorite part of the show. Buckle up, Stackers, because Doug, you’ve got a trivia question today
Doug: Hey there, Stackers. I’m Joe’s [00:35:00] mom’s neighbor, Doug, and I can hear and feel Joe’s moms upstairs dancing across the living room because it’s September 21st, AKA Earth, Wind & Fire Day. You know the song. I mean, it literally opens with, “Do you remember the 21st night of September?” Man, I never realized how I sound exactly like Maurice White.
Joe: Exactly. It’s uncanny. Wow.
Doug: Well, that song made tons of Benjamins referencing today’s date, but what was the significance? I’ll be back with the answer after I go move some chairs so we don’t have an accident like last year. That was a huge carpet cleaning bill.
Hey there, Stackers. I’m furniture mover and beat groover … Oh, that rhymes, Joe’s mom’s neighbor, Doug. Earth, Wind & Fire not only stacked a ton of Benjamins, they were inducted into the Rock & Roll Hall of Fame [00:36:00] in 2000 alongside other classic artists Eric Clapton, Bonnie Raitt, James Taylor, and The Lovin’ Spoonful.
Today’s question is about arguably their biggest hit of all, the song September. What was the significance of the 21st of September that they referenced to kick off the hit? The answer? For years the band said there was no significance, and 21st of September just sounded great, until 2019 when band members reversed course, finally letting everyone know it was the due date of the arrival of singer Maurice White’s son.
His son arrived very early, August 1st, but both mom and son were healthy and lived happily ever after. More good news: you can now share that with your friends right after you hear from OG and Anna.
OG: Hey, everybody. It’s OG. Anna’s here, too.
Anna: That was kind of scary.
OG: I know. No, it’s kind of, it’s kind of fun. So we are smack dab in the middle of conference travel.
Anna and I just got back from Future Proof. [00:37:00] Joe and the rest of the team are at FinCon. We’ve had sick babies and broken arms and all manner of chaos going on, so we are super gluing together this little episode. Uh, not exactly what we had planned when we kinda sketched out the, uh, season. But instead we’re gonna do some Q&A that we had piled up, and, uh, as Seinfeld said, we’re gonna pivot.
Was it … or no, it wasn’t Seinfeld, it was Friends. It was Friends. Anna doesn’t know either. So, so just a little Q&A time. So if you wrote in some questions and you thought it might be a little bit, you might get it answered today. All right, you ready? Let’s go. Let’s do some Q&A.
Anna: Hit it.
OG: And give the people what they want.
Anna: Yes. Anna. This is what they want.
OG: All right. Mm-hmm. So the first one that I’ve got here is from Michael. He’s in Arizona, and he says, “Hello, Anna and OG. Uh, I hope you can help with this question. My wife and I make good money, and we save consistently, but somehow we don’t feel wealthy. At what point in time should you actually feel like you’re doing well financially?”[00:38:00]
Anna: I hear this a lot during meetings, especially when we’re doing full financial plan meetings. So when we’re, like, really looking at long-term numbers, I hear this, I wanna say, 80% of the time. Mm-hmm. Like, people see their net worth statement, and they’re so surprised because they don’t feel like that’s actually how wealthy they are.
It’s important to be looking at that side of things, like looking at the net worth statement, looking at your total assets, because the reason why things feel tight is probably because you are saving quite a bit, and you’re having these, like, passive saving funnels that are happening. And so you don’t see a lot of the, the cash that’s going into these different channels.
So I think a lot of people experience this. I don’t think you’re alone, Mike, and I think that, that what you have to do is just kind of come back to those, like, monthly check-ins or quarterly check-ins with your family and be looking at, where does your net worth actually stand? How have [00:39:00] things changed? And if things feel tight cashflow-wise, maybe there’s some adjustmen- adjustments that actually need to be made, but more than likely, that’s probably a good thing ’cause it means you’re probably saving pretty well.
OG: Yeah, the reason your balance sheet looks so awesome is because of the discipline that you have, and so much of the social media and friends and family and stuff makes wealthy feel like, “I gotta spend a bunch of money.” And so it’s like, like, “I feel like I don’t have a lot of money to spend.” Well, yeah, ’cause you’re saving a bunch.
But maybe, you know, you’ve got a good amount of net worth saved up, and n- now that money can start compounding. You can let off the savings gas just a little bit maybe.
Anna: Mm-hmm.
OG: Free up some cash flow. Cool. All right, your turn.
Anna: Jennifer from Nashville, Tennessee
OG: Jenny, Jenny from the block …
Anna: Jenny from the block of Tennessee.
“I’ve got about 300K sitting in cash because the market feels expensive right now. Am I being prudent, or am I really just trying to time the market?”
OG: [00:40:00] Uh, B. Next question. I mean, first of all, awesome on having $300,000 in cash. That’s pretty flippin’ cool. Setting aside s- that some of that might be emergency fund and cash reserve money, and if it is, I think, you know, that you gotta carve out and say, “Hey, I’m supposed to have, like, 50K or 100K.
Like, that’s my emergency fund. That’s my, that’s my cash reserve.” When you’re trying to decide whether or not to invest, every single day looks like the worst time to do it because either it’s too high Mm-hmm … air quotes, too high, or it’s too low, right? It’s like, oh my gosh, the market’s down. It’s down 30%.
No way could I put money in today. Look at what’s going on, the chaos. And so the best method is to set up a s- system and invest the same amount at a regular basis. And now that you’ve accumulated a bunch of money, it’s gonna feel kinda weird to dump that all in because Murphy’s Law will tell you as soon as you put it in, it’s gonna go down by 5%.
You’re gonna go, “I knew I shouldn’t have [00:41:00] done it. That was a mistake,” you know, whatever. So what I would advise is kind of maybe like a two-prong attack. So first of all, take half the money that you would invest and invest it today. So you’ve got your asset allocation. Let’s assume that’s done. Just get the money in by nightfall.
So maybe 100,000 is your emergency fund. You got 200K left over. Invest 100,000 today. The other 100, we’re gonna decide one of two things. We’re either gonna say, uh, let’s say the S&P is at 7,000 today. We’re gonna say, all right, if the market does go down from here, at what number do we wanna get the rest of the 100 in?
So let’s pick a 10% number. We say, hey, it’s at 7,000. At 6,300, we’re putting the rest in. So we, we were right. It was high. Now it’s gone down. We got a discounted price. Let’s get it all in at 6,300 Conversely, which is probably what’s gonna happen, at what point in time do we say, “Okay, we were wrong”? But let’s pick that number to be maybe 5 or 10% higher.
So 7,000 is the S&P right now, maybe 7,700 or [00:42:00] 7,350, somewhere in there. You just say, “Okay, you know what? I was wrong. It wasn’t, wasn’t high, it was actually low relative to today, and now I gotta get the rest in.” Because if you look at the chart over a long period of time, you know, stocks go up and to the right.
There are just little periods of time where it goes down. And, uh, you know, you just can’t pick when those days are. So that’s kind of the best of both worlds. If I were t- telling you what to do, I would say invest it all tomorrow and just be done. But I think a good mix of going, “I’m gonna do a little today,” and then have a plan for the other, you know, the other half.
Either I’m right or I’m wrong, but I’ve got a decision to make when I get there.
Anna: Mm-hmm. Completely agree. I feel like for the last 10 years- Oh,
OG: completely agree.
Anna: Completely agree. I feel like for the last 10 years people have been saying the market is really expensive and it’s really high, and, and it’s just- Yeah
the same conversation, and, like, we’ve changed so much since 2016. So anyways, let’s- Yep … I’m gonna ask you the next question.
OG: Oh, I get another one. All right. Back
Anna: to back. You get, yep, back to back.
OG: Cool.
Anna: Uh, David from Grand Rapids, Michigan.
OG: Michigan.
Anna: Michigan. Go
OG: Blue. [00:43:00] Go Grand Valley State.
Anna: There we go. Um, “My wife and I are 54 and 52, and retirement suddenly doesn’t feel that far away.”
“What should we be doing in our 50s that’s different than what we were doing in our 30s and 40s?”
OG: This is kind of interesting because if you’re like most, let’s say young 50s, maybe you have kids that are now growing or grown and kind of transitioning out of the house, and the refrigerator bill, the shopping bill isn’t maybe as high as it used to be.
Maybe you’re traveling a little bit more. I think the opportunity that you have when you’re in your 50s, you know, setting aside the normal, I’d say normal things like you can save more money into your 401, you can do catch-up contributions, that sort of thing, is really taking stock of w- what is really important, you know, over the next, let’s say, 10 years.
Like, what do you wanna do? Because you’re probably in as good a shape and health as you’re gonna be, right? What do you… In a perfect world, what does [00:44:00] that look like from a retirement standpoint? Are you thinking, “I’m gonna retire when I’m 60 or 62 or 65?” Like that, those are all, you know, things to start thinking about.
And then as you’re working through your budget and cash flow, paying particular attention to the things that are gonna happen in the future, right? So maybe you’re aggressively paying the house off. We have done the studies on this, and we know or read the studies on this, and we know that the happiest retirees don’t have a lot of debt, if any.
You know, you say, “Well, but my mortgage is 2%, it’s super awesome.” It’s like, yeah, I know, but we can tell you that people say it’s really good not to have a mortgage payment. So maybe that’s a priority. Or starting to volunteer more and, and, and picking up what are the things that I want the next 20 years to look like if you’re on the back end of the kids thing and, you know, the kids may be off to college and that sort of stuff.
I feel like in your 30s and 40s, you’re like hanging on for dear life. You know, it’s like kids, and you’re beholden to the travel schedule of school and, you know, all that stuff is going on [00:45:00] with, with, with the immediate family. And now as you kinda get to that 50s, kinda early to mid-50s time Now it’s a little bit more of the expanded family, right?
You know, mom and dad are a little bit older. Aunts and uncles are a little bit older. You know, kids are starting to be out of the house. Like, what do you want that period of time in your life to be? And then what does that look like from a money standpoint? The good news is that most people in their 50s, this is kind of like your peak earning years.
A lot of times people worry about catching up and that sort of stuff. Stick to the plan in terms of investing. Maybe step on the gas a little bit if you have the opportu- opportunity to do that. But if you’re ahead of the curve or, you know, on pace, don’t be afraid to, to explore a little bit and have a little, uh, a little bit more fun.
Anna: Yeah. We’ve had so many clients who are, like, so, so good at investing in their 30s and 40s, that 50s actually might be a time where it’s like you still continue to work and pay your bills, but maybe we’re actually saving a little bit less on the other hand- Yeah … because we’re focusing now on, like, that retirement transition and visiting the [00:46:00] kids at school and, like, making that time to spend a little bit more.
So I’ve seen that transition too, where we’ve, I’ve talked with clients about, “Okay, what if we actually let off the gas when we get into this time period?”
OG: Yeah, yeah. Having so much flexibility, building in that flexibility kind of early on.
Anna: Yeah.
OG: Okay, we got time for uno mas. Yes. That means one more. Yep. Um, one more for Anna.
Uh, Chris from North Carolina, great city of Charlotte. “My wife thinks we should enjoy…” Kind of similar question here. “My wife thinks we should enjoy more of our money now, but I’m always worried if, about saving enough. We’re both reasonable people, but we see money completely differently. How do you figure out how much is enough, and when is it okay to spend?”
So kinda like what we were just talking about a second ago.
Anna: Yeah.
OG: Continuation.
Anna: That’s what I was gonna say. These questions are kinda tied together. I think it’s important, so I’m assuming that this client is also probably closer to retirement, because [00:47:00] they’re saying that they are saving. They’ve already saved quite a bit.
I know this is, this is kind of a self, a plug a little bit for us, but also just in general, if you have some sort of plan in place so that you understand how are these changes going to impact us long-term. Like, how does increasing expenses… ‘Cause once you get to a certain level of expenses, you’re probably gonna enter into retirement at that same level.
It’s not like you’re gonna go backwards in terms of spending. So- Right … I think when you do add on, we turn on the faucet a little bit more with the spending, we gotta assume that that’s gonna continue, like indefinitely, mo- more than likely. We’re not gonna go back in time in retirement. Um, there’s always things that are gonna come up.
So I think it’s important to have a plan and know how that spending is going to impact things long-term for you. So that’s number one, and I always think that it’s, i- if this is someone who’s similar to the previous [00:48:00] question writer, it is important to enjoy your money right now. There are so many conversations about how we enter into re- retirement, and we get hit with some sort of illness or disease or something like that-
OG: Right
Anna: or just shortly into retirement, and we are not able to actually enjoy it. So maybe what that actually looks like is balancing being able to do all these things that you wanna do while also working at the same time. So we’re not pulling from our assets to retire early to do all that stuff, but we’re able to kinda do it at the same time and let our previous savings just continue to grow.
So this is something, again, we talk about a ton with our clients- Yeah … who are, like, in this stage of life of transition- This is- … closer to retirement.
OG: I was gonna say, it’s a v- it’s a very common topic of, like, model out the worst-case scenario for how much m- like, worst case in terms of, like, how much I spend before the plan breaks.
bumper: Mm-hmm.
OG: And in conjunction to that, like, how much do I actually even have to work right now? Can I go back? Can I go down to 70% [00:49:00] time or 80% time or 50% time, and if I do that, I keep my, you know, I keep my insurance benefits, which is what I want, and I’m only working Monday and Tuesday one week, and Monday, Tuesday, Wednesday the next, and, you know, I’ve got these long weekends, and, you know, I’m paying my bills, and I don’t have to save anything because I’ve- saved for 30 years, and now it’s doing its thing.
So it’s kind of like a mini, like a mini retirement maybe- Mm-hmm … type of concept. But I think in particular as it relates to the comfort level of are we spending enough or, or can we spend more, and where’s the balancing act, it’s really just knowing what that is. And I think most people would be, who have saved, are pleasantly surprised to find out like, oh my gosh, like I would really have to go crazy in spending and, and go crazy in spending forever to have this be a thing.
Because it could, you know, you could say, well, you know, the wife wants to or the husband wants to, you know, have a trip. It’s like, well, you’re not gonna go to Africa and do a, you know, 15-day safari every single [00:50:00] year probably. Mm-hmm. So can you do it once and it’s 40 grand, and, you know, you bring the whole family and it’s like a boatload of cash?
Yeah, probably. Should you do it every single year? Eh, probably not. You know, if the market does really poorly one year, you know, it’s the Paul Merriman thing. The market did bad, so we, we have a lot of staycations. The market did really good, we’re going to Europe. You know? Mm-hmm. It’s just you just kinda plan accordingly and adjust, you know, as time goes on.
So these are really great questions. If you’ve got more questions for us, I think we like doing these rather than trying to figure out what it is that you guys wanna talk about. But if there’s something in particular you want us to cover or you’ve got a, a question for me or Anna to answer, og@stackingbenjamins.com.
You can leave a voicemail, stackingbenjamins.com/voicemail. And if you’re, you know, wanting to have these conversations with Anna or you wanna have them with me, you can, uh, reach out to us at stackingbenjamins.com/og. Just type in stackingbenjamins.com/ and you can fill in anything else you want after that.
[00:51:00] Voicemail, OG, you know?
Anna: Whatever you’re feeling that day.
OG: W- whatever you’re feeling that day, just plug that in- There’s, yeah … and you’ll probably go somewhere. Um, well, I appreciate you jumping on today. I think we did it. We’re gonna hit end. We did it. And we’re gonna kick it back over to Joe or Doug or, hell, maybe you’re kicking it back to me.
I don’t even know what’s happening right now. So it’s all I’ve told you. We’re just kicking
Anna: it.
OG: We’re just kicking it. See what happens.
Joe: Bye.
bumper: I’m Rocky Lalvani, the Profit Answer Man. And when I’m not helping small businesses stack Benjamins for themselves, I’m stacking Benjamins for myself.
Joe: Hey, guess what, Doug?
Doug: What, Joe?
Joe: We just got a letter.
Letters: We just got a letter. We just got a letter. We just got a letter. Wonder
Joe: who it’s from? Doug, you’ve got the letter. W- who wrote us?
Doug: JC wrote us, Joe. And JC says, “I’ve been listening to the show for two years and came to you through Paula’s show, [00:52:00] Afford Anything. Thank you for all the great information, education, and laughs.”
Are you JC, Joe?
Joe: I am … I’m JS.
Doug: Oh, yeah. It’s a soft … Yeah, okay. “I’ve never had a 401since most of my work life has been as a business owner, contractor, and freelancer. I have not heard any recommendations for people over 50 who have never had a 401. Most of the talk is for younger folks and/or people who have had the opportunity to have this savings option throughout a career.
A few months ago, I landed a full-time job working for a small and growing company that offers a 401. What is your suggestion/recommendation for how best I can set myself up to make good use of this opportunity? I am 50 and married. I do have a Roth IRA with Vanguard that I dollar cost average into monthly, and a three-month emergency fund, an investment account and money market account, and no debt.
My husband and I live small, but not without comfort. We are not big consumers and tread lightly on the planet. [00:53:00] No mortgage or car note. The kid is grown and on his own, therefore saving more now while I have a steady income can happen without feeling a loss to our daily activities. The company offers a Roth 401and a traditional 401.
They do not match contributions. I set the deductions up the first chance I got at 8% with a split between Roth and traditional, 4% each, with a 1% increase per year. State Street Target Retirement 2030K is the one that the company has set up for employees. I have 60% going into this fund.” I know you’re not a fan of the target date fund, Joe.
“These two I picked. T. Rowe Price, small cap value, 20%, Vanguard Morningstar Growth Index institutional 20%, $830 per month total going into these three funds. It looks like there’s an advisor fee and a plan administrator fee. Am I being charged by the company? Who do I ask about these fees? If you have thoughts, ideas, twists, or turns you think I would benefit from doing, [00:54:00] please do let me know.
I’m open to your input and am grateful for all the help you have given me already via your podcast and book. Looking forward to hearing from you. You’re the single best person I’ve ever heard on a podcast ever.” “Cheers, JC.”
Joe: Hey, Doug I don’t know, JC. But thank you very much, JC, for the kind words. And OG, somebody in their 50s, first 401ever, are they gonna use it differently than somebody who’s getting their first job at 25?
OG: I wouldn’t think so. This is great that you have access to one. Yes, if there’s anything I would do differently, I would, uh, probably ratchet up the savings a little bit faster. But it sounds like you’ve got that kind of on autopilot, which is great. Already talked about the fund choices and the target date fund, which is gonna be wickedly conservative for somebody who’s in their 50s.
Not a fan. And frankly, you’ve already demonstrated that you can pick through a few funds and say, “Well, I like this growth fund and I like this small cap fund.” What the hell do you [00:55:00] need a target date fund for when you pick two of the three you kind of need anyway? Like just add an international one and you’re good.
I might change that, but otherwise, no, I like it.
Joe: Yeah, I might
OG: swap out that- The pre-tax Roth thing, I was gonna say the pre-tax Roth thing, sorry, um, is kind of a… It’s just a guesstimation, right? It’s like how much should I put in each? Sure. Depends on what tax rates are today and what they’re gonna be in the future.
So hard to- Hard to say where you’re at,
Joe: but- Let’s talk about that. I do think JC, if she’s able to put 100% Roth in, like she was already into a Roth, at this point in life, why wouldn’t she just go 100% Roth?
OG: Yeah, I mean, I, I can’t say I disagree with that. It, it kind of depends on the total income, household income at this point and that sort of thing.
But I do generally fall on the side of, like, if you can pay the taxes today, it’s probably better than paying taxes in the future. But there could be some circumstances where the pre-tax side…
Joe: Yeah, no, G, obviously I’m with you. She already noted that you and I don’t like target date [00:56:00] funds because of the fact that they are so incredibly overly conservative.
You’re gonna end up with money in them most probably when you don’t need the money, and at that point, the fund continually gets more and more and more conservative, and you’re sitting on money that’s not keeping up with inflation. So it just does not make sense. Better to make the move when you need the money to reposition it into the bucket that is, uh, meant for using it today versus toward growing.
So if she’s 20% small cap value, 20% growth index, I would swap out that growth index for the 20% international piece, and then, you know, maybe then 60% into more of just a large company stock fund like a S&P 500 fund. And again, we don’t know enough about JC’s life and about when she’s gonna need the money to make a specific recommendation, but just directionally that’s kinda what I like better.
OG: Okay. Yeah. I can get, I can get behind that.
Joe: Yeah. She talks about the fees. There’s an advisor fee and a plan administrator [00:57:00] fee. These are when you work for a small company, JC, they’re gonna have some fees that get passed on to you because of the fact that they just wanna be able to offer this. I think while those fees exist, OG, you know, it kind of is not the end of the world.
OG: I mean, the alternative is don’t put money away If you have a seat at the table and you have a sense of how big the plan is, how many employees there are, how much money’s in the plan, there’s opportunities to renegotiate that as the plan gets bigger. And maybe the f- company can absorb some of those, or the plan administrator will be able to kind of restructure those so it’s a little bit less.
The reality is, is there’s a bunch of record keeping that has to happen here. There’s a bunch of technology that has to work correctly to make sure that your paycheck and the 401company are all talking together. There’s a lot of people involved. And like we talked about just, you know, a few minutes ago, ain’t nobody doing that for free yet.
You know? No. So ev- everybody wants to get a paycheck and put food on their table and, you know, that sort of thing. So if you’ve got an opportunity [00:58:00] to just say, … You know, my favorite question is, is this th- th it, and I asked my wife to do this when she went and bought a, uh, dishwasher the other day. She, our dishwasher was on the fritz.
She had, she knew exactly what she wanted. She researched it all. And I said, “Hey, do me a favor. When you go to the s- uh, sales guy, just say, ‘Hey, is this the best price?'” And she was like, “No, this is a little, this is like s-” you know, whatever. I said, “Just ask. What’s he gonna say?” Y- like, you did all the work, right?
You walked in, you
Joe: said- If he says yes, you’re where you are already.
OG: Yeah. Yeah. And you know what he said? Yeah, that’s right. He goes, “Well, I think we could probably pull forward the Labor Day sale, knock a few percent off. Is that, would that get it done?” Wow. She went on August 30th. Like, you know, uh, you know, just kind of lining up the stars here you go.
This, you know, I don’t know how the pay schedule works at Nebraska Furniture Mart, but if it was gonna work anyway, it might work like the end of the month is when I get my commission.
Doug: Mm-hmm. Mm-hmm.
OG: Right? So, um, you know, you just say, “Hey, is this…” Just ask. If you’re in the room, and you’re a decision maker, and you’re with the person who’s doing the 401, just go, “Hey, I see there’s a bunch of fees here.
Is, uh, is this the best price on all [00:59:00] these line items?” I
Joe: saw this w- with a friend in our adventure show that we do. They were just talking about when they walk into a hotel, they just say, “Is this the best room I could get, or is there, are there other rooms?” And again, you’re already in the room, and every once in a while they go, “Oh, well, we do have these other rooms we could do.
What, what, you know, what exactly are you looking for?” “Well, I don’t know, I just wondered if there was
OG: a-” Yeah, I could move you to the corner further away from the elevator. You know, like, that’d be great. If I
Doug: did that, the response would be, “I don’t like your tone, sir.”
Joe: Well- And I’d
Doug: be, I would lose the room I had.
Joe: It’s also… Neighbor Doug out on the, out sleeping in the car again.
Doug: Yeah.
Joe: And that’s not even from the person at the desk. That’s from Mrs. Neighbor Doug. “I don’t like your tone.” Uh, JC, there’s one other way to look at this, and that is 401plans have this rule of 55. And it doesn’t apply to all of them. Your 401has to allow it.
OG, if she’s looking at a retirement before 59 and a half, she may go the exact opposite way here, which [01:00:00] is to use this to build maybe her first money that she spends so that the rest of her money she can keep in growth mode. What do you think about that idea if maybe she’s looking at an earlier retirement?
OG: Yeah, I mean, if you’re trying to figure out where cash is gonna come from already.
Joe: Yeah. So the rule of 55, your employer has to allow it, but if you leave the money in this retirement plan, you may be allowed to withdraw it without penalty before 59 and a half. So again, you wanna dig into the paperwork about how your 401works, if it’s even eligible for that.
I certainly like the rule of 55 if it is available better than something like IRS Rule 72where you’re on a periodic payment plan on, like a pension-type schedule for 5 years or 59 and a half, whichever’s longer. So you could look at it that way. But w- again, we don’t… OG and I don’t know when you wanna retire.
Great question. Thank you for the question. By the way, a better move for JC would’ve been to call this in. We are building a show coming up, and we do these periodically, where we dive into questions when you [01:01:00] call them in. We thank you with Stacking Benjamin swag. Go to stackingbenjamins.com/voicemail or stackingbenjamins.com/yell downstairs and we’ll answer your question on a future show.
All right, that’s gonna do it for today. Big thanks to all of you for hanging out with us. If you have an advisor, you know somebody who’s looking at their advisor, not sure if it’s a great advisor or not, probably a good idea to pass this one onto them. It was a big question I got at Camp Fi, like, uh, uh, w- what’s an episode for this?
And after almost 1,900 episodes, we have an episode for just about everything that you could be looking for. But this is a good one for people looking maybe at their advisor. All right, that’s gonna do it. Doug, you’ve got it from here, man. What should we have learned on today’s show?
Doug: Well, Joe, first, take some advice from our top five.
Bad advisors leave lots of clues. Great advisors can make you a great investor, so hire wisely. Second, that 401, jump in. Even in your 50s, a 401is a great retirement vehicle that can make it much [01:02:00] easier to save because of payroll deduction. Even better, you can stop it if things get too tight. You’re not locked in.
But the big lesson After seeing Joe’s mom dancing in the living room, there is no way I can forget the 21st of September. That’s something you can’t unsee. 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.
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 [01:03:00] show
JC says, “I’ve been listening to the show for two years and came to you through Paula’s show, Afford Anything. Thank you for all the great information, education, and laughs.” Are you JC, Joe?
Joe: I am… I’m JS.
Doug: Oh, yeah. It’s a soft… Yeah, okay. Uh, “Details with questions. I’ve never had a 401k” I wasn’t supposed to read that, was I?
Joe: I know. That’s why I just deleted it. I was like, he’s gonna read that.
Doug: And I read it. Yeah
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