If you’re not familiar with a Deferred Sales Trust (DST), you’re not alone. While it may be a relatively unknown strategy, a DST, similar to an installment sale, can help mitigate significant tax liability for certain individuals. Primarily used by business owners and real estate investors, the proprietary tool is a flexible and valuable way to defer taxes when selling a highly appreciated asset, such as a business or property. On his podcast, The John Chapman Show, John welcomes guest Greg Reese, founder and principal of Reef Point LLC, which assists people in DST transactions.
What is a DST?
When a business owner, for example, sells their business, rather than receiving a lump payment from the sale, proceeds are placed in a DST. The seller can then draw upon the funds as income, similar to a 401(k) or IRA. A DST’s benefits are that the seller can decide the distribution amount they need every year and only recognize and pay taxes on what they withdraw annually. This approach allows individuals to avoid paying a lump sum of taxes in a single year, increasing their tax bracket, and dipping into their available cash reserves to pay taxes.
John and Greg discuss why you may consider using a DST for your next sale, including:
- An exit strategy. You are a business owner or real estate investor wishing to retire or move onto another investment and hold a highly appreciated asset you would like to sell.
- A 1031 exchange alternative. The primary difference between a DST and 1031 is the flexibility of the distribution terms and control offered within a DST to engineer your payments to meet your tax and financial needs.
Listen to the full episode for complete details and to hear John and Greg discuss:
- The financial minimums required for a viable DST transaction
- The mechanics of the DST process
- The valuable estate planning and asset protection components
- How you can creatively distribute your funds to support your goals and lifestyle or pay off debt
- The fee schedule and legal and maintenance fees within a DST transaction
Speaker 1: (00:02)
Welcome to The John Chapman Show, where we talk about retirement readiness strategies to help you grow and preserve your wealth so that you get the most from life with the money you do have. Are you on track? John is an employee of Worthpointe, LLC. All opinions expressed by John and podcast guests are solely their own opinion and do not necessarily reflect the opinion of Worthpointe. This podcast should not be relied upon for investment decisions. It is for informational purposes only.
Are you a business owner or real estate investor that feels paralyzed by the potential looming tax bill you might pay when you sell your business or property? Well, on today’s episode, I talk with Greg Reese, founder of Reef Point, LLC, about a proprietary tool called the Deferred Sales Trust and how it can be used as a way to defer taxes on selling an appreciated asset. A deferred sales trust or DST for short is similar to an idea of an installment sale. And in the case of a DST, it can allow for an asset to be sold and avoid having to pay taxes all upfront, but rather allow the business owner or real estate investor to take up to a 10-year period to decide how much in each year and when to take the income from the proceeds of this asset and still invest the money along the way. Of course, this is under current tax law which is subject to change. You should always check with your own tax advisor for your specific situation, as neither I nor WorthPointe provides tax advice.
Of course, this is a unique tool that has some complexities, so be sure to consult your financial advisor or attorney or tax professional along the way. But whether, again, you’re a business owner or a real estate investor looking for maybe a 1031 alternative, a Deferred Sales Trust is a potential strategy that you can look into. And so without further ado, let’s dive into today’s episode with Greg Reese. I’m so excited to talk about Deferred Sales Trusts and how folks can learn a little bit more about deferring taxes. So it seems, Greg, as if the biggest problem that the Deferred Sales Trust is trying to offer a solution to is mitigating tax liability. So tell us a little bit more about who should be considering a Deferred Sales Trust in the first place.
Yeah, good question. And you’re exactly right, because you know, the different sales trends really operate in three primary areas. The first one is an exit strategy. So for those people that started in business years ago and they’re looking to retire or sell it and move on, you know, what you find with business owners is almost the entire sales price that they get for their business is taxable because most business owners start with a computer or a phone and that’s their core investment at the start. And now it’s worth hundreds of thousands or millions of dollars. So it’s a huge tax liability. So, and also real estate owners, for example, most of the transactions involve the sale of real estate or the sale of a business. There are other things that are involved, other types of assets we can get into later, but they’re looking to have an exit strategy.
So business owners want to retire and kind of move on to a different retirement life. A real estate owner might want to get out of the active management of real estate. In other words, some might say, you know, I’m done with the tenants, toilets, and trash, and I want to move on to the club’s cocktails and cruises. So they move from the three teams and the three seats, and it could be for health reasons. It could be for lifestyle reasons. It could be to remove the handcuffs from always having to be available and there, and dealing with those midnight calls and stuff for the plumbing breaks or you know, electricity alters or whatever it may be. And so, you know, that’s the first exit strategy. The second lane we operate in is really a temporary one: exchange alternatives. So we all know the 1031 exchanges are a mechanism to sell and appreciate a piece of property and then reallocate into another piece of property and defer the taxes through mechanisms of IRC, section 1031.
Some people will use the DST as the vehicle to achieve the same result. But the key differences, if you use the DST, you can park your money effectively and wait for the right opportunity and not be bound by the timelines and other restrictions that are associated with 1031. So with COVID right now, we’re sort of still in the middle of it, so a lot of the real estate investors I talked to, a majority of the percentage feel there’s going to be better opportunities in several months down the road to 18 months down the road. They just think that the prices may come down or there’s going to be, you know, great opportunities. And so they don’t want to be stuck just trying to find something within 45 days. And then that’s coupled with the fact that the real estate market is still very strong.
Right now, prices are high and there’s oftentimes multiple offers going in on various properties. So I find people that have put offers in and they got beat out and they’re struggling. And they’re stressed about finding that right upside property. And sometimes, you know, in this confluence of these two events, sometimes they might find something or not. But if they do, sometimes it’s not ideal and they have to do what I coined years ago: sometimes you have to hold your nose and close, right? Not getting what you want, but you know what? You don’t want to pay the tax. If you had an alternative that allows you to park your money until you find the right opportunity that you love. And then you could do that and use the DST as your vehicle to achieve. But that’s valuable. It creates tha alternative.
We might have listeners, Greg, that are thinking something like that sounds amazing. And why haven’t I heard about this? And a lot of real estate investors, I’ve probably heard about a 1031, but maybe haven’t even gone down that road because of the fear that, like you said, of not knowing what the next leg is or having it be, you know, blown up during the deal or something like that. So maybe just really quick before we jump back to the mechanics for those that are thinking, why haven’t I heard about this before? What’s one of your responses to them?
So, you know, I often say, you know, almost every day that the DST is a strategy that’s not new, but it’s still new to a lot of people. And the primary reason for that is that the strategy itself is proprietary in nature. Campbell Law invented this, you know, in conjunction with following the IRS, but we don’t own the code, and the mechanics of how we put together transactions is unique. A lot of the intellectual property that goes into that and knowledge about the law and tax and the IRS and all that is very specialized. And the reason why there’s 10,000 other tax attorneys that aren’t really doing this right now, unlike 1031s, where there’s thousands of people involved from escrow to title, to exchangers, to appraisers, to everybody, everybody knows about 1031 exchanges because there are so many people that could benefit and play a role.
But in this space, it’s a unique, specialized way to utilize the code. And in order for that to become accepted and mainstream and get to the point in its life existence where that strategy is considered legal, proven, and tested, you got to go through some pain, you got to go through the scrutiny and it takes years for the IRS to even pop up and say, Hey, look, I’ve seen a couple of hundred or a couple thousand of these transactions, and we’re not quite sure what’s going on here. We want to investigate. So what do they do? They’ll do individual audits on individual clients, right? They may go to the proprietor of the law firm or organization that’s putting that together in the first place. They’ll typically do both of those things, but they’ll start with the individual audits because they want to examine individual transactions.
And it takes them years to sort of start to do that. And one of the core benefits every client gets when they retain our services is the attorneys stand behind their work. So if a given client is ever audited during the life of their particular DST trust, they will offer to represent at no additional costs. They will defend them. They will step up and defend it and basically back up what they’ve done. And it’s a low water rate, which is great, but enough has been done so that we can honestly and with integrity, say that our strategy is legal, it’s proven, and it’s been tested. Yeah. Other providers that, you know, could be smart enough to sort of replicate, figure out what we’re doing, they haven’t even gotten to the first base of that. So that’s why we’re in a very unique situation.
Okay. That makes sense. So I’m thinking now about some of the mechanics, again, for people who are thinking to themselves, gosh, this sounds interesting. Maybe this is for me, there’s some other criteria that might need to be met and I’ve seen in some of your literature that maybe it’s those that have a certain threshold of unrealized capital gains. So what’s the dollar amount that they should be thinking about when they’re weighing, do I sell this business or real estate, or do I look for a tax deferral strategy? Are there some dollar amounts or parameters there?
There absolutely are. So we’ve kind of determined that there’s a sweet spot or what we call a minimum viable transaction. So, okay. And I’ll say it two different ways, but it means the same thing. So the first way I would categorize this is if you are the seller of a highly appreciated asset, regardless of what it is. And if you were to sell that asset with no particular planning and fault and the resulting tax liability for you, federal, state, Obamacare, all around, would be 80 to $100,000 or more, then that is a viable case to consider using the Deferred Sales Trust. Put it another way, because not everybody knows what my tax liability would be if the appreciation or the gain that you would be taxed on. So in the case of a business, that’s kind of almost the whole purchase price purchase price over with real estate. Really it’s a mental calculation that says what is my appreciation from what I first bought it for? Plus how much depreciation have I taken since I’ve owned it? Add those two together. If that amount is about $250,000 or more, that’s saying the same thing in different way—that’s viable for a look at. Definitely.
Okay. And, you know, in Southern California, that’s in some ways a really low hurdle, which makes us even more attractive, because I was even thinking of coming from the capital markets, somebody that has a significantly appreciated stock from their company, or they’re an executive or something like that. So, you know, unrealized gains of $500,000 or more, but maybe for real estate, because you’ve got the depreciation factor to, you know, 250,000 combined with appreciation plus depreciation. So, you know, in some ways that’s not an enormous hurdle for someone to start thinking, okay, I might have more than a hundred thousand dollars in terms of a tax liability. Now, I’m really interested. So I want to keep talking about some of the mechanics of it.
Sorry, I’ll just interject really quickly. Another kind of asset class that most people wouldn’t even think about is your primary residence. So, you’re working and living in Newport Beach and I live in Newport Beach and my home office is in Costa Mesa, but we’re surrounded by multimillion dollar properties all around us. And the IRS does have a little bit of a tax benefit for some of those folks, all the section 121 exclusion, you can write 250,000 if you’re single or 500,000 if you’re married for your home. But a lot of people around here have a gain that’s much larger than that. Definitely much larger than that. And sometimes it’s the main house. The kids are gone, they want to kind of consolidate, or maybe they want to free up the equity to move into smaller quarters to have income that they can use for their lifestyle. So this strategy can also be used with highly appreciated personal residence.
Yeah. Okay. That’s another good example. And so I think as I’ve learned a little bit about the DST, there’s a couple of key components to it, you know. First, let’s say, just taking the example, if you’re selling an appreciated asset, and I’m just going to pick on a business, if I’m the seller of a business and I’m about to receive, let’s say $2 million for gross proceeds for the sale of the business. There’s, you know, one step which is the money goes not maybe directly to me, but to a trust. And then there’s another mechanic of us. There’s some period of time that I would get to defer the taxes for. So can you talk a little bit about where does the money go and how long does somebody have to defer it and you know, what might happen in between that timeframe?
Sure. So I’m going to scratch it to a half a step back and just kind of set the stage for what we’re really accomplishing here. So we’re utilizing section 453, which is the code section that governs the use of installment sales for real estate owners. That’s often referred to as a seller carryback for business sellers; it’s often referred to as an earning. The definition of an installment sale is one in which some of the proceeds of your sale will be received in one or more years beyond the actual year of sale. That’s the definition of an installment sale. Now the rules under installment selling mean that you only have to recognize and pay taxes on what you actually receive from year to year. So before I get into the mechanics, let me just throw an analogy your way, because I think it’s relatable to a lot of people.
Put your imaginary cap on, imagine that you could sell that business, sell that real estate, and place the net proceeds of sale before taxes into a trust for your benefit—much like it’s your personal IRA or 401(k). Once the money hits your 401(k), if you will, you get to decide how to reinvest those proceeds. We’re going to move with you. We have a team that comes as part of the DST strategy, but you ultimately will decide how you want those proceeds reinvested. And it’s not limited in the way 1031 exchanges are. You can reallocate your proceeds into any viable investment class you want. It could be real estate. It could be another business. It could be anything under the sun, really, that is a true bonafide investment. Number two, just like it was in your 401(k) or IRA, the client will determine how much they want to withdraw from their account from month to month or year to year, right?
Number three, they will only recognize and pay taxes on the amount they actually withdraw, just like your IRA. If I don’t need the money this year, I let it grow. But as soon as I need some money out of it, I’ll recognize and pay taxes just on what I’ve taken, right? So there’s a lot of control and flexibility. Number four, which is really a side benefit of what we do is, well, let me talk about it from an estate planning standpoint, because that’s one of my specialties. The client gets to designate effectively how any of their sales proceeds are going to be ultimately distributed or applied to the benefit of their designated heirs. So there’s an estate mining component to this, too, so that, hey, it’s a really big deal to have all this money sitting in this DST and you’re drawing income from it and you should die, for example.
What happens to that money? Well, it will accrue to the benefit of your designated heirs. And we’re going to work very closely with you to make sure that you do have that in place. It’s like if you placed an IRA for a client, you’re not going to just open the account and not have a beneficiary, that doesn’t take place. Now we’re going to make sure that they have their beneficiaries in place as to what they want to see happen. Number four, asset protection, is sort of a byproduct of the benefit. If the client sells their business or their real estate, the money’s in their DST, they’re drawing from it just like they would if it was a 401(k) or an IRA. If they get sued or they get a judgment against them, for any reason, it’s almost impossible for their judgment creditor to get access to the principal.
And so it’s got similar protection, you know, and I don’t want to speak as a lawyer, stuff like that. That’s not my intent here, but I’m just telling you, there’s a really strong protection on the principal that’s in your trust at any given time. So that’s the analogy I want to make before I kind of get into sort of the mechanics. So the mechanics kind of look like this. You’ve decided you’re going to sell this appreciated asset, right? And you’re going to go through the normal process that any owner would: hire a professional to help you market list, negotiate offers with potential buyers, negotiate the final terms with the ultimate buyer. You’re going to control that whole process. Just like you always would write in the background, we’re going to work with you and their transaction parties to create this trust for you and have our tax attorneys integrate with you and the transaction parties, whether it’s escrow, title, an attorney or a broker, whoever it may be in order to sort of weave this in, it’s kind of like the DST becomes an option that you want to consider, and you want to weave it into your transaction early.
It has to be created before you actually close, because once you closed or come close to closing, the IRS considers that you either have the money or you as good as have the money; they’re going to post that to you. So you want to have the structure set up in advance and you want to have it set up conditionally so that there is no cost upfront to put it together. You’ll only pay the legal fee. If you actually close with the DST, you’re not obligated to close with the DST. It’s kind of like selling a property and putting in a 1031 exchange provision into your contract. That just basically says, as the seller, I reserve the right to engage in the 1031 exchange. If I so choose or at my own expense, it doesn’t mean I have to do it.
It just means I have the right to do it, right? Oh, it’s sort of the same concept. So once we set up the trust and we get everything coordinated in advance, you don’t ever have to make your decision whether to use or not until right before the close is going to occur. If you don’t use it, there is no cost or a small issue. If you do use it, you’ll pay the legal fee. But then what happens is the trust receives the cash at close. You receive a promissory note for the full balance, the full amount that’s in that escrow, right? Which enables you to report your sale as an installment sale. Meaning that you’re telling the IRS I sold this thing for $5 million, but I haven’t gotten any money yet. And under the installment rules, what did I say?
You don’t recognize or report or pay taxes unless you actually received the money makes sense as an installment sale. And that way you create a note with your trustee, which is viral and you let me know how you want to receive your money over what period of time. We’ll figure out that attractive rate of return that should be applied to that note. And then the payout structure that you need to support, whatever bowl you have, whether it’s a lifestyle and income or pay off debt or whatever it is so that you all only, just like that 401(k) analogy, you only ever recognize and pay taxes on what you actually dropped from time to time. Every year you’re going to get a 1099 from the trustee that says, hey, here’s how much you withdrew from the trust. Here’s how much represents interest on your note. Here’s how many represents principal that might be subject to capital gains.
That’s fascinating. I have to admit that my brain as a financial planner runs wild, thinking about all of the creative ways that the distribution side of this can be crafted, because I’m thinking about all my clients that are in retirement and they’re taking money out of their 401(k). And maybe some years they’ve got high ordinary income. If they’re getting a severance payout or a deferred compensation payout, and then they’ve got years where they’ve got low income because they haven’t taken Social Security yet, or they’re not age 72 and not falling on their IRAs. And so it’s, if I’m hearing you right, Greg, it sounds as if there’s a lot of flexibility for somebody who’s sold something for $5 million that’s wanting to use this kind of installment sale idea and then have that 5 million to be paid back to them. I mean, eventually we’ll be paying taxes. They eventually will receive that money. It’s just not as if boom, all of it hits their tax return in this one year, right?
That’s right. So, you know, really two fundamental tax benefits that are at play here. Number one, by being able to defer the taxes you get to keep the money you would have paid in taxes to directly benefit you. The seller taxpayer, whether for income purposes or wealth accumulation purposes, if you’re not diluting your nest egg with tax money, who would otherwise go over here? Right? Exactly. Let’s say you are going to own a million dollars in taxes. What if you could keep that million dollars, put it to work directly for your benefit if you’re just looking for income and just to keep it super simple. What if I can earn 5% on that million dollars? Sure. That’s an extra $50,000 a year. I would never see exactly 10 years. That’s a half a million dollars. Right? Second tax benefit is if you sell without planning, the entire capital gain gets added to your other income in the year of sale. What does that do to your tax brackets? Boom, you’re up here. You’re at the top. There’s no question. Every single client that is eligible to do this, they would be.
Especially in the state of California.
A hundred percent California. But what if you could engineer the payments that you receive? Only such that you actually need the money. It’s like, I always go back to this IRA concept because none of us are going to retire tomorrow and cash out our IRA one hundred percent.
Right. It doesn’t work that way.
I don’t need to spend all the money this year. That would be the reason. I mean, nobody would do that. So I might as well just take it, pay debt. You’re all going to take what you need to supplement your retirement. If you take too much from your IRA the next year, you know what? I took a hundred thousand out of my IRA last year, but I left 50,000 in the bank at the end of the year. Why did I pay taxes on that extra 50,000 if I didn’t need to spend it? Exactly. I’m only going to take 50. And if it’s not enough, I’ll pick more. Or if it’s too much, I’ll back it down again. That’s what we’re talking about here.
So I love this because you know, it makes a lot of sense, especially in my context for folks that are retired and they’re wanting to design their income and there’s a lot of free range to be creative for how somebody takes income. And especially, maybe in regards to a business sale, you know, it’s going to be fairly or even any other appreciated asset. It’s going to be somewhat straightforward, but something that I’m hung up on, Greg, maybe you can help me. And maybe even the audience is thinking about this, too. So if I think back to a real estate example and somebody that is looking at the market and they’re saying, you know, I really want to redeploy this money. I would normally do a 1031, but there’s just too low inventory. So I can’t actually achieve my goal. How could they use the DST to further sales, but then redeploy into let’s say a real estate of their choice. And then are they effectively coming out of the DST? And they’re going back to a regular depreciation schedule with their real estate or something like that. So am I missing a link there?
I mentioned that when you’ve closed your escrow and the trust is holding all this money and you’re trying to figure out, okay, how do I want to reinvest this in order to meet the goal, which is get paid back a hundred percent of what you got in your account, plus a rate of return. So you’re going to need to invest that in some fashion, in order to achieve that ultimate goal. Now you could invest in traditional institutional types of investments, equities, bonds, ETF products, alternatives, and real estate, passive, you know, all that. You might also want to go out and buy active real estate. You might want to invest in a business and you might want to do hard money loans to other real estate owners.
These are other things that are sort of outside of the scope of a financial advisor, but you don’t typically manage real estate for people. You don’t buy cryptocurrency for people. You don’t do hard money loans, but those are eligible investments. If they could invest it certainly. So what happens is, you know, just simply put the DST can be a joint venture partner with the client who wants to go in that direction. So if they want to buy real estate a year from now, as opposed to 45 days from now, then they’ll find the property. They’ll tell the trustee what they need as far as the down payment goes. And they will be in charge of investing those funds. And the trust will come in as a joint venture partner. So we could get into the weeds about how that’s actually structured, but it’s really quite simple, you know, draw with the balloon payment down the road, but you can take any amount of money. You can amortize it. You can take a specific amount, you can take partial interest or interest only whatever you want to do, and you can change it over time. So what works today makes sense today; your lifestyle may change in a year or two, and you might want to modify this to keep pace with your changing lifestyle.
Greg, if someone’s seriously considering this, I think we’ve shed a lot of light on potentially a new area. It sounds really compelling. So I appreciate this. What are some of the fee schedules or the legal costs or the maintenance cost, things like that. So somebody can just understand what the ongoing fees are.
Sure. Great question. You know, our fee schedule is pretty much a standard schedule. It’s very transparent. So we bring three professionals into the mix with every DST transaction. One is the tax attorney, who’s coordinating all the legal work that needs to be done and defending it if it ever needs that. We’ve got an independent trustee, which is per the regs, gotta have the independent trustee and somebody is going to have to be approved through the organization. And then there’s an independent financial advisor. People just like yourself, you know that they’re going to help give advice and recommendations about how you might consider reinvesting your proceeds, even though the seller controls those decisions, it’s beneficial to have help guiding them to make them for themselves. So there’s a one-time, non-recurring legal and setup fee that’s due at the close.
Only if you close with the DST, which is the equivalent of one and a half percent of the first million dollars of your transaction amount. And one of the 4% of anything above a million dollars not referring those away on an ongoing basis. Easiest way to describe this is you’ll have somebody like yourself and myself that are performing roles to keep the integrity of this, oversee and manage investments, and work with the client on an ongoing basis. The two of us combined are typically going to earn between 1.1 and 1.5% annually, and that’s not separately. That’s kind of a combined fee schedule based on the amount of assets in the trust from year to year. That’s usually the fee schedule up to about $2 million in assets. As the amount of assets is higher, our percentage goes down. The idea is that our annual fees should be covered by the performance of the underlying investments that the clients choose that are approved. Definitely the client had, for example, a certain percent note rate on their DST. We expect the management and selection of those assets, the average performance is going to be 7.1, 7.5, so that our fees are net of their target return. That makes sense and is always the goal that we’re managing to; we want to see at least that target return on average delivered to the client, not diluted by some matter of ongoing fees.
Super, Greg. Well, this is spectacular information. I appreciate your sharing. Just remind us again. If somebody is interested in looking at your website or a little bit more educational content, what’s the best way for people to continue to learn about a DST?
You know, there’s a lot of good content on my website. If you care to check it out, even a couple of videos that give you a high-level explanation. You would go to reef point usa.com, reef as in great barrier reef. That’ll give you all kinds of references and resources and even mechanisms to reach back to us if you have.
Awesome. And if you do have questions, for the listeners out there, feel free to reach out to me. And that way I can talk about your specific financial planning needs and bring Greg into the conversation for an additional analysis. So, Greg, thanks again for joining us today. We really appreciate your time.
Thank you, John. I really enjoyed being here. Thank you.
Speaker 1: (31:24)
Thanks for tuning in to The John Chapman Show. Be sure to subscribe on iTunes, Stitcher, or Spotify. We encourage your questions, comments, and feedback for additional information. Check out The John Chapman show.com or look for John on LinkedIn and Twitter. See you next week.
Other articles filed under Financial Planning
July 19, 2021 - If you’re not familiar with a Deferred Sales Trust (DST), you’re not alone. While it may be a relatively unknown strategy, a DST, similar to an installment sale, can help mitigate significant tax liability for certain individuals. Primarily used by...
September 29, 2020 - Let me guess… You became a financial advisor because you want to help families secure their financial futures. You envisioned yourself coming to work every day fired up about helping your clients accomplish their dreams. But you’ve hit a roadblock....
August 27, 2020 - For most financial advisors, owning your own firm sounds like a dream. You set your own schedule. You call all the shots. You take home all the profit. But even if you’re pocketing all the profits, do you really earn...
June 17, 2020 - WorthPointe advisors John Chapman and Matt Addington provide their answers to that question in a new video that touches on three areas: the emotional impact of the pandemic; what you seek to accomplish; and what changes, if any, may be...
June 12, 2020 - Are you one of the many people who sold at the end of March when the market dipped — and are now wondering what to do next? In a new video, WorthPointe founder Christopher Van Slyke and advisor John Chapman...
- Retirement Planning: Where the Rubber Meets the Road
- Got Aging Parents? This Advisor’s Book Is For You