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We’re not overpaying. No, we’re not overpaying. We’re not overpaying anymore. The tax code’s complicated, boring, and overrated. You don’t want that, you want a pro. One thing that you should know: this is a radio show. It’s not tax advice, don’t take it that way.

Steven (00:49):

Hello everyone, and welcome to the next episode of the Retirement Tax Services podcast, financial Professionals Edition. I’m your host, Stephen Jarvis, CPA. And with me today I have Larry Sprung a financial advisor who is kind enough to come on and talk about the ways he incorporates taxes with his clients. So Larry, welcome to the show.

Larry (01:08):

Hey, thanks for having me, Steven. It’s a pleasure to be here and always say pleasure to talk taxes, I guess, right?

Steven (01:16):

I love it when people can say that with a smile on their face. We actually got introduced through another guest on the show, Eric Shadoan. So shout out to Eric. I always love meeting people who, who can genuinely with a smile on their face, say, let’s talk taxes.

Larry (01:29):

Absolutely.

Steven (01:30):

So Larry, tell me why you’re willing to get on a podcast and with a big ol’ smile on your face, talk about taxes.

Larry (01:36):

Well, listen, it’s something we talk about very, very often here at Midland Financial because, and I think it’s something that anybody who is an advisor has to have these conversations with the families they serve. Because if you think about it, almost everything we do, everything we advise on, everything we talk about has ramifications and implications. And many times those have to do with taxes. So it’s something that we have to have a working knowledge of , and I’m not a CPA but I’m sure we’ll talk about how we work with the team of the family that we serve. But it’s important to have that knowledge because when you’re advising families, you better have at least an understanding of taxes because it’s gonna come into play.

Steven (02:25):

Oh, yeah, absolutely. I jokingly will put out lists of things that financial advisors do that don’t have a tax impact. And of course, that list is blank. Larry, it would probably be helpful if you could just talk real high level about maybe what your typical client looks like or the most common tax areas that you’re focused on, and then we’ll get into what does that actually look like in practice? I’d love to dive down to the details of what are the actions you take?

Larry (02:49):

Yeah, so, you know, the families we serve, ideally are somewhere in the one to 5 million range. They’ve done a great job of accumulating assets or are in that accumulation phase, right? And where we come into play is we act as almost like the family’s personal CFO in terms of helping them and guiding them in almost all areas of their financial life. And where taxes come in are in a number of different places, right? It could be as simple as looking at capital gains from year to year to talking about Roth conversion strategies to QCDs for families. It, you know, it goes on and on and on. And we find that that kind of sweet spot in that 1 to $5 million range is really where a lot of these concerns start coming up. And then obviously $5 million and up, there’s even a greater emphasis on tax planning and strategies. So, you know, we’ve developed a process over the years in terms of, you know, addressing these issues on an annual basis with families and making sure that we’re hitting on those important areas that they need to be addressing and be on the lookout for and make sure that they understand that what they do today could have an impact, not tomorrow, but when they go to file their taxes in April of the following year. And we wanna make sure those surprises don’t exist.

Steven (04:19):

I love taking out surprises. A lot of times when we, when there’s articles or social media posts on taxes, it’s really just focused on, I mean, these edge cases, these exceptions of, Hey, let’s save somebody a million dollars in taxes. That may or may not have actually happened, but one of the ways we can deliver value on tax planning in addition to helping reduce someone’s lifetime tax bill, is just taking those surprises out, taking some of the pain out, giving a little bit of clarity. Now, Larry, I know you host a podcast as well, and we’ll give everybody a where they can go to to follow up with you on that afterwards, but because of that, I’m gonna trust that I can put you on the spot just a little bit. So you have to forgive me if this is coming outta nowhere, but I recently came across a Roth conversion that just, just peaked my interest. So, out of curiosity, what is the largest Roth conversion you’ve ever advised a client on?

Larry (05:09):

The largest one we’ve ever done is about 300, 400,000, somewhere in that range. Okay. And that was a couple years ago.

Steven (05:16):

Yeah, that’s a pretty big amount. This is one of those things that Roth conversions come up all the time and you mentioned it as a potential opportunity, but what I find like so many other things is that people wanna have just like a rule of thumb of, well, every Roth conversion should only be up to this percentage or this amount, but if we’re talking about a 3 or $400,000 Roth conversion and the one that came across my desk recently was just over a million dollars. And to me, I love seeing those, those kind of, well, what for a lot of people is gonna be an edge case because to me, it shows that we’re thinking specifically about that situation. I am not saying that everyone should go out and do a $400,000 Roth conversion tomorrow, or million dollar Roth conversion, but it needs to be specific. So maybe Larry, maybe talk a little bit about how do you have that conversation with a client, or how do you help them decide whether they’re gonna do a $400,000 or a $40,000 Roth conversion?

Larry (06:09):

Yeah, and, and Steven, like you said, I think it’s more of an edge case than it is a rule of thumb, if you will. Yeah. We probably do more 25 to a hundred thousand dollars Roth conversions, maybe even 25 to 75 than we do 300 or 400,000. But in this particular case and with this particular family, and I think what you’re getting at is, you know, well, we talk about here is, you know, planning is personal. Yeah. There, you know, when I hear general rules of thumb being spewed out, that this is the way everybody’s gotta do something, generally that doesn’t work that way, and that means that they’re not listening to me. But in this particular family’s case virtually like 90 to 95% of their assets were in qualified monies and they had very little in non-qualified monies whatsoever.

(07:00):

So essentially, and, and they’re young, they’re in their early sixties. So at their point in their stage of life, everything that’s coming out to support them is pretty much taxable at this point. And they wanted to have a period of time that would not be the case, or if they didn’t need to, that money could be passed on to their heirs. So for them, it worked and we were very conscious about the amount and taking into account various tax brackets. I I will tell you this, we actually advised the client to not do that large an amount. We actually talked to them about doing a smaller amount because we felt that it would be a greater tax savings, but we presented, you know, both and they wanted, and were interested in doing more. So we drew up the case for that and showed them, and really their rationale was, they really wanted to take the hit from a standpoint of, you know, social security and their Medicare premiums being hit in one shot rather than having a prolonged increase in those premiums on a go forward basis.

(08:06):

And listen, you know, we’re not here to make the decisions. It’s not our money. They made it, they earned it. It’s their hard-earned money. We’re there to make suggestions and then help them make decisions, show them the pros and cons. And if ultimately they go with something that may not be our top choice, then as long as they do it with their eyes wide open, we have to help facilitate that and make sure that it happens in the best way that it can in that scenario, I think.

Steven (08:33):

Yeah. Larry, thanks so much for sharing that example. There was a couple of things that really stood out to me in there. I love that you’re covering so many different areas that you’re thinking about as you’re making that recommendation. You brought up social security and Medicare, you throughout their age, the percent of their money that’s qualified versus non, that this isn’t just a, well, here’s what’s left in the bracket, so go ahead and do it. And then you also commented on ultimately, I mean this is the client’s money, which is it, it seems almost silly that we have to reinforce that, but it is their money. They worked really hard to earn it. And at least the way I heard that is, it’s not that you’re gonna make a recommendation. And if they’re like, ah, Larry, I don’t wanna do anything you say that’s probably a different kind of outcome if they’re just gonna ignore you. But there’s gonna be this kind of this range where we say, Hey, as long as we’re going in with our eyes wide open, I really like that you put it that way. If we’re going in with our eyes wide open, you know, what this means for you both now and long term, it’s a range there. In no situation is there one magic number for what a Roth conversion should be.

Larry (09:31):

Yeah, I agree. And I mean, to your first point, if it was as easy as checking a box and saying, Hey, it’s this, this and this, families wouldn’t need us, right? Yeah. And we talk about it all the time, you know, as much math that’s involved with all of this. It’s more of an art than a science when it’s all said and done. And you have to be an artist really in this profession, to be able to present these things and understand how everything works together.

Steven (09:58):

Yeah. I mean, a lot of people get, whether it’s financial planning or accounting taxes, I mean, a lot of people get into these professions because they have an affinity for numbers. It’s really easy to nerd out and try to find the mathematically optimal outcome for, well, if we do X, this exact amount, then over the next 20 years, that’s how we just do it perfectly. Perfect Doesn’t exist. But to your point it’s that balance of yes, we’ve gotta understand the numbers, we’ve gotta be pointing the client in the right direction, but we’ve gotta do things that they’re actually gonna implement. Because even if you figure out what that perfect number is, if they’re not committed to it, if they’re not excited about it, they don’t understand it, they’re not gonna follow through on it. And in a couple of years when there needs to be some kind of follow up action or something’s changed in their life, they’re gonna look back with resentment and not, oh, that’s right. We had this plan and here’s why we’re doing this.

Larry (10:46):

Agreed. And I think to your other point is, you know, you have to look at these planning techniques as dropping a pebble in a body of water, Right? And what we try to do is anticipate and understand what those ripple effects are gonna be once that pebble is released from our fingers, versus being reactive and dropping the pebble and figuring out what it actually is in April. And I think that’s where we come in many times unfortunately, where somebody has had a bad experience and they had an advisor who was really just an investment person, who was, you know, investing money for them and not really being an advisor. And that’s really where we come in. We’re really on the advisory piece. We’re advisors who happen to get involved in asset management. We’re not asset managers who happen to get involved in planning.

Steven (11:40):

Yeah. Being able to step back and consider all those different things is just so critical. Larry, one of the things I hear from the audience quite often is questions around, okay, but how does this work in practice? It’s nice for us to get together and talk kind of really high level about, oh, here’s these great situations where we helped a client. But you mentioned that a lot of your clients are maybe more in that 25 to $75,000 Roth conversions. I mean, talk about the mechanics a little bit. What time of year are you bringing this up? How are you identifying which clients this is a good fit for? Is this something you delegate to people on your team? Like how do you make this a reality?

Larry (12:14):

Yeah, so I mean, everybody on the team is really on the lookout for potential opportunities. And there are things that we’re looking for there are telltale signs that present this in a good light that could be a good opportunity for a family, right? One thing is that they have a lot of qualified money versus and also have non-qualified money. Cuz one thing we haven’t talked about is when you do these conversions, there’s gonna be tax bills and, you know, we as a firm do not feel it’s a good idea to, you know, pay the taxes from the conversion. Meaning if your goal is to convert 50,000 and you’re gonna have a $20,000 tax bill, we don’t want to gross that 50,000 up to cover the taxes too. We don’t think it’s that efficient. So we would prefer if the family has dry powder in the terms of non-qualified money on the side to pay those taxes.

(13:06):

It’s an ideal situation. So if they have a good amount of qualified money and a good amount of non-qualified money, that’s a good indicator that this might be a good idea for them. Two is if they don’t have any Roth money already, three is if they are already hemming and hawing about potentially taking RMDs at 73 or 75 whenever they’re gonna have to start taking them and they’re already heeing and hawing about it that’s another good indicator. And if they, you know, if they’re in the situation where they have a pension that’s, you know, an income already that’s covering their income needs, you know, these are all indicators right. And that basically just brings us to a point of having a conversation with the family. And I think they’re younger, they are better off if we are to have these conversations because I think most of your listeners, although I don’t believe in this, you know you know, the model that fits everybody, I think a lot of the folks we speak to pretty much agree on the fact that taxes, there’s a high likelihood that taxes will be higher in the future than they are today.

(14:18):

So that’s another indicator. And these generate conversations and then we talk to them and see if there is an interest for them to go down this road. If there is, then we start modeling some opportunities of converting some of the IRA money. And what we’ll do is we’ll model it in different increments. We’ll model it at 25, 50, 75, a hundred, you know, in those increments and take a look at what the impact would be for them. And then we have another conversation. And then typically once we get on the same page, if this sense for them and we pull the trigger on that first initial Roth conversion, then it becomes a thing that we review again on an annualized basis. And I think one thing that really prompted a lot of conversation around this was last year because markets were down, which really presented another opportunity that we haven’t had in a long time, which we had these conversations saying, Hey, basically if you’re down, you know, 15, 20% right now, you can convert that much more and then when, and if the markets bounce higher, you’re just gonna benefit that much more from those events.

(15:28):

So it also prompted a lot of conversations. So I I think it’s a, you know, it’s a confluence of a lot of events and you know, your team and my team is trained to look for those kind of fact patterns. And again, that doesn’t mean that just because they have that fact pattern that it’s right for them, it still requires those additional conversations to make sure that it makes sense for them, they understand it, to your point they’re bought into it, that it makes sense for them and that they’re gonna continue implementing it and utilizing it over time and see the value.

Commercial (16:04):

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Steven (16:58):

I like that you highlighted both quantitative and qualitative factors that you’re looking for. Again, it can get, it can be easy to get hung up on the numbers and there certainly are numbers that will tell us, Hey, this might be a good candidate for Roth conversion. But, you slipped in there a couple of times of the client’s attitude, those conversations that are going on, whether they’re hemhawing about RMDs. There’s some of these things that the qualitative piece is important. We can’t forget about that.

Larry (17:22):

No, and I’ll share with you, we had a family last year that he is in his early fifties. Has a ton of qualified money. We’ve talked to him about RMDs and he has more income than he’ll ever need because he’s a retired FDNY, he’s got a really nice pension. He’s collecting social security disability at the same time cuz he went out on disability. So he has more income than he would ever need and last year he was fighting a disability case to go out on Social security disability and we were at the final stages of about to make a Roth conversion for him. He was all on board. He felt it was a good move cuz we figure, you know, he’s in his early fifties, we have about a 10 year window to start converting his IRA money to Roth over that 10 year period and really make some significant impact so that he doesn’t have to worry about these RMDs.

(18:14):

And at the last minute in like the first week of December of 2022, he got notified that his disability case was settled in his favor and he was getting a payout backwards to when he filed for disability. Wow. So he was getting a huge lump sum and at that moment he was like, you know what? I don’t know how much I’m gonna owe on tax on this lump sum. Yeah. You know, we’re trying to work that out. He’s like, I don’t know that I want to complicate my tax situation this year any further. So how about we put this off till 2023? And to me it made sense. We didn’t wanna rush it at the last minute or final weeks of December to get this squared away and potentially make an error that we couldn’t reverse. So we figured he had 10, 11 years now we’ll have nine or 10 years to do this same thing. It’s really not gonna make a difference of, you know in the long run. But I think that’s an example where both qualitative came into play and quantitative, you know, into that decision making process.

Steven (19:14):

Definitely. Larry, what are some other areas that you’re seeing value to your clients through taxes? Roth is a huge opportunity and it, and certainly one that gets addressed quite often. Sounds like you’ve got a great approach to that. But what else do you see?

Larry (19:27):

Well, last year we had a great opportunity with regard to tax loss harvesting, you know. If any of your listeners have been in the profession as long as I have, it’s been a long time since we’ve really been able to do that in a meaningful way at the end of the year. I know that there are a lot of strategies that will you know, take losses along the way during the year, but if you’re not in one of those active type strategies, it was really the first time in a long time that we were able to really make some significant headway with regard to that. You know, we’re always talking with our small business owner clients about the benefits of, you know, whether it be a single K whether it be a simple IRA set IRA or some vehicle like that.

(20:09):

You know, perfect example. We had a family that we work with called us up in November and basically they had a business that was gonna have about a million dollar plus profit at the end of the year. And he was kind of scrambling, what could we do where, you know, where could we put in money? They had a SEP previously. So I said, have you ever thought about a defined benefit plan? So long story short, we coordinated with their cpa, we coordinated with their company and basically we were able to shelter about 300 plus thousand dollars of their profit between four profit sharing and cash balance plan significantly reducing their taxes. You know, again, you know, you have to have an understanding of what to look for and when you see it, then put it into action and work with the team.

(21:03):

And in this case, the accountant was so pleased because he wasn’t really familiar with a cash balance plan. He kind of knew about them but didn’t know how it would work. And then, you know, he asked some good questions cuz he was concerned about the company’s ability, not their ability to continue funding it. He was concerned about the owners wanting to continue funding it. So we made sure we got on a call with them and made sure that they understood that there was a, a commitment here that they were you know, it wasn’t a one and done that they could use it as a tax shelter. It was something that we were gonna have to consistently utilize on an annualized basis. And they were thrilled because their expectation is that this business is gonna continue in the same direction. So it’s things like that in new, you know, being in New York, there are some small benefits to making 5 29 plan contributions.

(21:54):

To New York State 5 29 plan. So it’s just, you know, understanding those nuances, looking for them and, and then coordinating and collaborating when needed with the other team members of the family to make sure that what you’re thinking from a tax perspective is actually going to benefit them. And we talked about not liking surprises. The last thing I want to do is get a phone call from their CPA who I’m trying to build a relationship with in March saying, what did you do? You know, we try to have that conversation in October and November so everybody’s on the same page when those tax documents arrive, our tax letter arrives. Everybody understood what took place and there are no surprises.

Steven (22:39):

Yeah. So much value in taking those surprises out of it. And I’m sure the CPA was thrilled that you’re working together on a strategy that saved taxes in the current year because I know at times where advisors run into frustration working with CPAs is on those strategies that intentionally pay more taxes now because most CPAs are tasked by their clients to get ’em as big a refund as possible right now, even if that isn’t really the best for their long-term plan. Larry, you talked about building relationships with CPAs and you mentioned a tax letter in there. I’d love to hear how you approach doing a tax letter and then what you’ve seen successful in building those CPA relationships.

Larry (23:14):

Yeah, so I mean what we do from a tax perspective is anytime we perform a task or do you know, a level of service for a family that we work with that’s tax related, we basically document that information into a tax letter for that year. And then essentially over the course of the year, you accumulate a number of different things that get embedded into that document. And then what we do is from the beginning of the year through about the end of January at the latest is we go through those families and make sure that all those items that we address during the year are on the tax letter. So things like, hey, your 1099 reminder’s gonna come out around January 31st, but keep in mind there may be some amendments to you. Remember you made a $10,000 contribution to your New York’s Day 529 plan two, you did a Roth conversion two, we took tax loss harvesting this year, or set up a simple separate 401k and then we send that out to the family so they have a copy.

(24:20):

We also CC their accountant so they have a copy. So hopefully when they get the documents, they’re matching it up to what’s in our letter and they understand that everything that we’ve done is kind of wrapped up right there. And I think that that goes a long way to building those relationships with those CPAs and tax professionals. Because I know a lot of the folks that come on your show and talk to you, they’re doing some similar things to what I’m talking about. But I assure you, and I think you could attest from experience, a lot of advisors are not. So that allows us to separate ourselves immediately with the accountant, with the tax professional. And if you think about it over the course of time, that just builds up a level of credibility and reassurance that the family’s in the right hands.

(25:13):

And if they have somebody that could utilize this same handholding and same advice and guidance, then we become a go-to partner for them. So it starts by building that relationship, by having those conversations, making sure that there aren’t any surprises, and then reinforcing that with the letter. Just kind of reaffirming what was done over the course of the year. And I can’t tell you how many times Steven, we reach out to a client’s or a family’s CPA initially to have a conversation to talk about, you know, X, Y, Z, we’re thinking about this for the family, what do you think? And they’re like you’re calling me. I’ve never had these conversations. Usually I find out about it afterwards and I’m like, no, this is not how, this is not in the family’s best interest. If you’re finding out about it afterwards, it’s in their fa family’s best interest if we talk about it.

(26:08):

Now, if you say you’re, you’re on board and I’m on board, then we definitely know it’s in the best interest of the family and we have to move forward. And sometimes it takes both of us to have that conversation with the family to make them understand what the, you know, may be in their best interest. Because sometimes having one over the other, you know, may not make sense or they’re going back and forth between the two of us. That’s a difficult conversation cuz as you know, things get lost there. So it allows us to get on the same page initially and then talk to the family.

Steven (26:41):

Yeah. I really like how you described that and that was a great reminder in there that we do handpick the people who come on this show. And so if you just, if you just take the advisors who come on as guests as a representation of the entire industry, you might think, oh, well everyone’s doing all this stuff. No, I assure you it is very much the exception. I spend a lot of time working directly with advisors, helping them in improve how they’re doing their tax planning. And these are things that we’re talking about all the time of getting tax returns from clients, of communicating with CPAs, of doing these tax letters or 1099 letters. And you’re absolutely right that that’s one of the best ways that you can build that relationship because it demonstrates to the CPA how you deliver value to clients. It’s not you patting yourself on the back and telling the CPA how great and smart you are or asking them for referrals, which is a terrible idea. It’s you demonstrating what you’re doing to take care of the families they serve as well.

Larry (27:32):

Yeah. And I think what you have to do is, you know, there’s, you know, people are hesitant about reaching out to the CPA because they feel like they may be threatened by us. You know, we’re not looking to replace them. We’re not looking to, you know, replace their job. We’re just looking to enhance the relationship that they currently have and maybe even take some of the onus off of them, right. Because yeah, there may be some of these questions that they’re getting that may be better suited for us that they may feel obligated to answer. But now if they know we’re competent, they’ll say, you know, listen, this is really better suited to talk to Larry and we do the same, this is better suited to talk to Mr. Or Mrs. CPA if we know that they’re a qualified person to do that.

(28:14):

And it just makes life that much easier and it makes sure that the family’s getting the best advice and guidance that they should be getting. And I will tell you this occasionally again, we’re not looking to catch mistakes, but occasionally we do. We had a family we work with that we ran their tax return through holistiaplan. and I realized, or we realized that there was no capital gains listed in there tax return for the year. And I’m like, that’s weird cuz I know we had checked their account. There certainly were the accountant missed the 1099 even though they were reminded and told they missed it. And then we had to inform the client, client went back to the CPA and then they had an amended return done to, to include that. And again, we’re not doing it for those specific purposes, but, you know, you do catch those things from time to time. People arehuman, they make mistakes.

Steven (29:12):

Yeah. We all do. And that’s, that’s such a better outcome for the client for you to identify it and have it corrected before they get a love letter from the IRS. Right. And so, I mean, they, either way they still have to pay the additional taxes, but it’s definitely a better outcome. Well Larry, I really appreciate your time coming on and talking about all of this. We like to make sure that people are turning this podcast into value, which of course comes through action. So we’d love to recommend some action items for our listeners from this conversation we’re having. So since you’re the guest, I’ll let you go first. As you think about the things you do in your practice for your clients, what are action items you would recommend that advisors take who also are looking to up their game on taxes?

Larry (29:48):

Yeah, I think you have to get a process down in terms of knowing what you wanna do, right? And, and it may not be all these things because depending on the size of your practice, you may not be able to, you know, service all of these things. So I think you have to get a list of those things that you can do now and start and use that as building blocks to start building on and maybe have a wishlist of items that you’ll add to it. And then start working out a process in terms of how are you going to implement and get those items done. Who’s going to do them and when you’re going to do them. You don’t wanna wait till December and then all of a sudden have to pump this out. There should be action items that everybody’s taking throughout the year to do this.

(30:33):

And it shouldn’t rely on just one person, it should be a group. And I think the third thing I would say is make sure your team and the organization that you’re with understands what those drivers are and those things that you should be looking out for as a team that would warrant some of these conversations. Because a lot of times these discussions are on the same topics. Those drivers are the same. Once you’ll hear it again and once they’re trained and educated on it, once they hear it, they’re gonna snap into action and say, Hey, we should be talking about this, or we should be contacting your accountant. So I think if you take those three things, you know, I don’t want to overburden you, but I think if you take those three items and figure out what you’re gonna cover a process around it and then train your team members on what to look out for, I think that’ll be a great start to get you on your way to addressing these issues for the families that you serve.

Steven (31:30):

Great recommendation there. And I’ll, I’ll add that on that list of things that you can do. Everyone listening to this podcast really should already be doing this, but if you’re not getting tax returns for every single one of your clients, you don’t need a designation for that. You don’t need years of tax experience. That is a place that everyone can start and every definitely every advisor should be doing. And of course, if you’ve made it this far through the podcast, you’re clearly enjoying something. So last action items. So take a minute to go, give us a five star review, leave a comment. We want this to keep growing so that we can help more and more advisors serve their clients through taxes. So Larry, once again, thanks for being on the show. It’s been great having you.

Larry (32:02):

Hey, thanks Steven. It’s always a pleasure and make it a great day.

Steven (32:06):

Thank you every, for everyone listening. Until next time, good luck out there. And remember to tip your server, not the IRS

 

We’re not overpaying. No, we’re not overpaying. We’re not overpaying anymore. The tax code’s complicated, boring, and overrated. You don’t want that, you want a pro. One thing that you should know: this is a radio show. It’s not tax advice, don’t take it that way.