Thinking Like a Family Office with Ashley Tison - Episode - 566

There's 8,700 of these things. You know, it's amazing some of the real estate plays that are out there under 1.0. And I think that we're gonna see the same thing happen with the 2.0 designations, that there's really great places that people can go to invest. And then, you know, I'm also able to, you know, kind of get 'em outside of the box to say, hey, listen, this isn't just a typical 1031 where you're going into another locked and loaded real estate deal. Let's get outside of the box, right? You sold your business. I know you've wanted to do this other business, so let's create that as a Qualified Opportunity Zone business.

Most people focus on how much they make. Family offices focus on how much they keep. Thinking Like a Family Office breaks down how disciplined investors redeploy gains, reduce tax liability, and invest with intention without crossing ethical Or compliance lines. Welcome to Stream Stamp Act, brought to you by Steve Tucker Capital. I'm your host, Dr. Allen. Most people are taught to focus on how much they earn. Family offices focus on something very different, and that is how capital is structured, protected, and redeployed over time. That difference often separates taxable success from enduring wealth. Today's conversation is about learning to think that way. Not as a billionaire, but as a disciplined steward of capital who wants decisions to be defense, intentional, and aligned with long-term impact. Before we begin, I want to invite you into Beyond the Paycheck: The Financial Clarity Compass, a private mini instructional masterclass for professionals who want their money to work as intentionally As it possibly can. You can access it at www.go.stetucker.com/beyond-paycheck. This conversation is for educational purposes only and should not be construed as investment, legal, tax, or financial advice. All investments carry risk, and you are encouraged to consult your professional financial advisor before making any decisions. Many professionals experience a liquidity event and immediately ask, how do I minimize taxes? Family offices ask a very different question. How do I redeploy capital in a way that's defensible, intentional, and aligned with long-term impact? Today's guest has built his life's work around helping investors make that shift. Ashley Tyson, Esquire, is a tax strategist, entrepreneur, and co-founder of OZ Pros, a leading advisory firm focused on Opportunity Zones and advanced tax-efficient investing. Through OZ Pros, Ashley has helped investors legally defer or reduce more than $1 billion in taxes while directing capital into projects designed to create jobs, housing, and durable community outcomes. A magna cum laude graduate of WNC Charlotte and WNC Chapel Hill School of Law, Ashley draws on his background as a real estate and securities attorney and fund counsel to build practical, audit-ready strategies, not theoretical tax plays. Known to many as the Oz Sharpa, he's respected for translating complex tax code into clear, compliant decisions that mirror how family offices think, regardless of portfolio size. Today's conversation isn't about loopholes. It's about learning how disciplined investors structure exits, redeploy gains, and align capital with both preservation and purpose. So Ashley, welcome to Streams to Impact. For someone hearing about Opportunity Zones for the first time, can you explain what the program is in plain English and how it came into existence and why a professional with a recent or upcoming capital gains should be interested.

Yeah. So, Allen, thanks for having me on the show. It's an honor and a privilege. And I think that opportunity zones are the greatest tax incentive ever legislatively created. You know, there's all types of different tax things that are out there that were creatures of kind of creative planning and creative strategies that people have deployed. And I'm nothing against those, but as it relates to actual legislatively created ones, I think that the Opportunity Zone program is bar none the best one that's out there. And I gotta hand it to the drafters of the legislation that they were, number one, they were able to sneak it into the Tax Cuts and Jobs Act at the final hour of 2017. And that number two, in 3 pages of legislation, number one, They got the attention of private capital. Number 2, they got it off the sidelines. And then number 3, they made it patient. And they'd done— and we're talking about to the tune of no other program ever before, to the tune of about $150 billion worth of private capital going into areas that need it the most. So the authors of the legislation saw that in 2017 that there were these areas of the country that had been kind of bypassed by the rebound from the Great Recession and that they had not experienced a similar rebound. And so what they wanted to do was incentivize private investors to go into these areas and invest into either real estate deals or operating businesses that would then have the benefit of kind of raising the tide and lifting all boats in that area. And so they said, all right, how can we do this? How can we manage to, number one, get the attention of private capital? And so they made this program as simple as possible. And so it's an as-of-right program. So the greatest thing about the Opportunity Zone program is that you do not have to ask for permission from anyone. All you have to do is have a capital gain. And I'll get into the why of the capital gain here in a second. But if you have a capital gain and you put it into a qualified opportunity fund within 180 days of that gain, Or a little bit longer if it's coming off of a partnership or a K-1, that you get to defer that capital gain under the first program. So I'll also explain OZ 1.0 versus 2.0. You get to defer that capital gain for a period of time. Under 1.0, it's till December 31st, 2026. Under 2.0, it's 5 years. And then in order to get 'em into the gain, they say, To get 'em into the game, they said, listen, if you're invested by December 2019, we're gonna give you a 15% reduction when you pay the taxes in 2026. And if you're invested by December of 2021, we're gonna give you a 10% reduction. And so they got 'em to actually get off the sidelines. So that's the second thing they did. So number one, they got the attention of private capital because they made it as of right. Number 2, they got it off the sidelines. And then number 3, they made it patient. Because after a 10-year hold, after you've held your investment inside of the qualified opportunity fund for 10 years, it comes up out with a step-up in basis to fair market value. That's really significant because the difference between your basis and fair market value is what you pay taxes on. And so if you get a step-up in basis to fair market value, that completely eliminates capital gains taxes, but it also eliminates depreciation recapture. So through that, they were able to get private capital to move $150 billion into qualified opportunity funds that are now investing into these 8,763 qualified opportunity zones that got designated back in 2018 as opportunity zones. If you're interested in seeing where those are, you can go to ozpros.com/map and you can pull up an actual address, or you can generally kind of search around to see where they are. And so, you know, part of the kind of the initial overwhelm was like, oh man, well, I gotta be some sophisticated fund manager to go out there and do this in order to invest into a qualified opportunity fund, or I've gotta invest with, you know, a fund manager to do that. And the answer is that a qualified opportunity fund is not something that's all that complicated. It can literally be a partnership Or an LLC taxed as a partnership where you've designated it that it's going to invest into qualified opportunity zones. And so we've set up almost 2,000 entities at this point where people are doing this, right? From Main Street to massive capital gains. Anybody that has a capital gain, whether that's long-term, short-term, it could be from the sale of a business, it could be from the sale of stock, it could be from the sale of crypto. It could be this from the sale of appreciated gold or silver, any other kind of collectible that you take that capital gain, you drop it into a fund inside of 180 days, you get to defer that gain. And then that gives us time to be able to do other tax mitigation strategies before you have to pay that gain. But the great thing is, is that whatever your new investment is, whether that's real estate or an operating business, after your fund turns 10 years old, everything that's a capital asset that's owned by that fund is coming out tax-free. So as you can imagine, that's a really powerful difference when you compare a side-by-side investment, right? And you compare just letting it continue to eat in a taxable environment versus shifting it into a tax-free environment. So that's why we've seen $150 billion move into opportunity zones.

Well, thanks for that explanation. That makes a lot of sense and brings a lot of clarity. And you also gave us the site on your site that we can go to to find Opportunity Zones. So, once we have found the Opportunity Zone, we have the capital gains, and we know where the Opportunity Zones are, the next question is, how do we find the opportunities within and the opportunity zones to invest in?

Yeah, so there's, I mean, the great thing about the program once again, right, is that you could either invest with a professional fund manager. So there's about 7,000 qualified opportunity funds out there. There's a database that we've got that we'd certainly be willing to share with folks, right, if they're interested in that. We've got some, and once again, it kind of depends on what they're interested in, what kind of specific kind of investment categories they might be more or less interested in, whether it's real estate, whether it's multifamily, industrial, or perhaps agricultural land, or if they're interested in operating businesses, like specifically what kind of operating businesses that might be. We've done deals for folks and we've got active funds out there that I mean, it literally, it runs the gamut. It's storage deals. We've got a fund that invests into RV and boat storage that's creating jobs and that's also positively impacting the communities that they're in. And we've got active operating businesses, right? So I helped somebody buy a bakery that was in an opportunity zone and they did it with their own capital gain. So the possibilities are pretty much endless. It's more of a function of what You know, like, uh, like what can't you do then versus what can you do? And I can tell you that the can't you do list is, is fairly short. You can't have a sin business, so it can't be a golf course or a, uh, a hot tub facility, a tanning salon, or an off-premises alcohol, uh, place like a cash— like a C-store that's selling liquor or a liquor store. Um, and then you can also not— it's very tough to do kind of financial services businesses that are heavy on actually having to hold financial services instruments because there's a restriction on non-qualified financial property, which is cash, stocks, bonds, accounts receivable, that kind of thing. So what they didn't want somebody to do was to set up a hedge fund inside of an opportunity zone and then be able to not have to pay taxes on the growth of those capital assets. And so pretty much everything else is on the table. And we've helped people do deals where they've actually taken their capital gains and they've set up their own captive fund. A lot of times people do that because they want to have the flexibility to potentially do their own deal, but then also to be able to allocate into different professionally managed funds that are out there and to just co-invest alongside of the sponsors in the individual deals. So that's kind of the bread and butter of our business is setting up captive funds and then helping people to figure out their strategy and helping them execute the strategy about exactly to your point, like how do you find the deal inside of the zone? What kind of deals should I be looking for? What should I be thinking about? If you're doing a real estate deal, you either need to be buying something that's new construction or that needs substantial improvement because that's a category. They didn't want people just land banking land and just sitting on stuff. And so that's one of the requirements is that you get in and you actively do something to it as a real estate deal. On an operating business, man, we can pretty much buy anything. Whether you're starting up a business from scratch or you're buying an existing business that's in the zone or you're buying one from outside of the zone and moving it in, we've done all of that as well.

Yeah, opportunity zones are a great thing to be into. The one limitation that I keep running into with them is that they're so arbitrarily created, and you can have a multifamily opportunity that sits across the street from the opportunity zone, and you're just out of luck.

Yep.

It's, you're either in it or you're out of it. And you had mentioned you can move businesses into it. Well, you can't move a multifamily.

It's, it's a little bit tough to pick that, uh, pick that apartment complex up and move it across the street. Right?

Exactly. Yes. So, uh, so yeah, that has been the dilemma that I have run into with that.

Yeah. So unfortunately the zones were designated back in 2018 and there was not a whole lot that we could do about that. And so what Congress did is they allowed the governors to designate up to 25% of their low-income census tracts as opportunity zones.

Mm-hmm.

And so the governors came in and they, you know, they picked and chose based upon usually kind of local input about which ones were most investible of the low-income census tracts. The smart states did that. Other states like Massachusetts just said, hey, we're just gonna pick the bottom, you know, lowest income census tracts, and we're going to make that our zone. And they've seen the least amount of investment. Alabama got really intentional about it and said, listen, we think that these zones are the most investible. And as a result, they've gotten the most amount of investment. And so they're, as part of the legislation to create permanency inside of the program. So the first program timed out December 31st, 2026, under the original legislation. Now, you could still invest after that, but you'd had to have the capital gain prior to that point in time. And so what Congress, because they saw how much money and how much impact these things did have, they said, listen, we need to extend the program. And they didn't just extend it, they made it permanent. And so as part of that, they said, hey, listen, governors, we're going to give you the ability to redesignate zones every 10 years beginning July of 2026. So there's actually a window right now where the governors are going to be redesignating zones. And so if somebody's interested in having their zone designated, they need to get involved with their local governor's offices right now to make that happen and to start lobbying for that designation. I'm helping a gentleman down in Florida that's got a sporting lodge that should be inside of an opportunity zone where he's located. It absolutely should be. And he's literally getting ready to buy like the better part of this town down there in order to bring more jobs in and that kind of thing. And so he needs to be talking to the Florida Department of Commerce or whoever it is inside of the Florida governor's office that's going to be designating zones to say, hey, listen, on the next round of designations, I need you to pull this zone in. And pull this census tract in because we've got some really cool stuff that's happening here and this area is inherently investible. And so that's what people need to be doing now if they're interested in trying to get either their parcels or their projects or their areas and localities designated as an Opportunity Zone census tract.

Makes sense. Yeah. That's how the political machine works, doesn't it?

It is.

Lobby and stay involved. So you have seen capital deployed well and poorly. So what measurable community outcomes show up when it's done right, and how do we as investors vet the deals for both real impact and financial discipline?

Yeah, so what's interesting, and this is the great thing about the program that I love, is that Just by very definition of investing into one of these communities, you are going to have positive community impact because it's new dollars coming in that would've otherwise not been there. And we've seen that time and time again relative to deals that are getting done just because of the fact that they are Opportunity Zone deals. That by very definition lifts the tide for all of the members of that community. And we're actually seeing the results of that through EIG studies and through other things that are coming out that are showing that the census tracts that got designated as opportunity zones are outperforming their peers that were similarly situated tracts in the form of increasing home prices and also just increasing property values and significant movement in the context of the poverty scheme. That we're seeing people starting to come out of poverty in these zones. That's where we've seen the needle move. And we've seen that from the data that EIG, the Economic Innovation Group, is putting together. EIG was part and parcel. They were part of the original architects of the Opportunity Zone legislation, and they've done a great job of keeping a finger on the pulse of it. And putting that information out there relative to how it is positively impacting those communities. I've seen specific deals that are having absolutely cool impact too, right? That it's palpable stuff, right? There's a gentleman that was doing an autism community down in Alabama where they were creating kind of a closed ecosystem where the autistic folks would have a job working on a farm. And I mean, it's absolutely changing lives. I've just got story after story of things like that where we're seeing jobs created, we're seeing things happen inside of the community. And part of that is that you just need to, as you're evaluating a deal, like any kind of deal that you're looking at from a private investment standpoint, You want to look at the quality of the sponsor. You want to look at how intentional they've been about crafting their deal, all of the things that they've thought about that they're presenting to you in the context of that deal, specifically including how, what is the measurable and what are the KPIs that they're attaching to that community impact piece. And so by very definition of going into these zones, they're going to have impact. But I think that the really good sponsors are also showing you measurable places about how they're actually doing it. And then they're anecdotally sharing evidence of the stories of the lives that they're changing. And we've seen a ton of that happening. We've got a bunch of sponsors that are actively doing that. If somebody's interested in seeing deals that kind of walk and talk like that, we can absolutely put 'em in front of that.

Well, thinking like a family office, when you say this, what does that mean in practice for exits, for timing, and for redeploying capital?

So family offices are focused on creation of generational wealth. They're focused on the real true economics of, okay, how do I take this How do I steward this resource, whether it's from an exit or whether it's an actual business or whatever? How do I best steward this resource? And so they're looking at that critically from all angles. They're looking at it in a taxable environment versus a non-taxable environment. They're looking at it from a transactional deal drag basis as well. They're looking at all of the factors that could have impact on that, including dynamics of, okay, How much risk am I looking at as well inside of my portfolio mix? And so the family office then gets really intentional about taking action steps in order to shift the risk, right? To trying to minimize the risk as much as possible, both from a geopolitical to a market risk, also down to that tax and transactional risk as well. And the drag that is put on the return based upon that. Opportunity zones then become a really powerful tool for that family office because it allows them to take things out of a potential market risk, right? So they can go in and they can evaluate their portfolio and look at things where they've got significant appreciation. And instead of just kind of doing the de facto, like, well, man, I don't want to sell that because I don't want to have to pay the taxes. Instead, they're like, okay, Now's the time to sell that because that's probably at the apex of its growth potential, or certainly on the upside of that curve. And now let's take that and let's shift it on a tax-deferred basis into a tax-free environment that, oh, hey, by the way, not only is it inside of a tax-free environment, so instead of looking at, all right, how quickly can I flip this? How quickly can I achieve the highest internal rate of return possible? Instead, what they're saying is, how long can I keep this inside of this tax-free environment and how can I eliminate deal drag and transactional fee drag along the way? And so, opportunity zones line up perfectly with those metrics relative to now being able to stick something into something that they've done their due diligence on and saying, listen, I'm going to let it sit and I'm going to let it eat inside of that deal. And now, I'm not going to have to spend my time, my energy, my resources on underwriting it every 3 years, looking for the next deal and worrying about a time clock on getting it in on a 1031 basis, right? So, a lot of private equity shops do this. They look at real estate deals and they're flipping it every 3 years because they think that that's the greatest return metrics available. But then every 3 years they're having to find another deal. Every 3 years they're having to underwrite it. They're having to pay transactional fees. They're having to pay brokers. They're having to pay all of this stuff along the way instead. And so you need to really factor in those costs versus being able to do it one time and letting it eat.

Yeah, absolutely. So for listeners who want to act without creating friction with their CPA or advisors, how does your firm plug in, simplify the steps, and help to deploy capital into compliant and audit-ready projects?

Yeah, so we've got, uh, we've got a couple of different ways that we interact with people, right? Like on the products that we sell, We've got the setup where we'll actually set up somebody's own captive qualified opportunity fund. We can then do their compliance for them if they want us to. We can do their bookkeeping, and we're not stepping on anybody's toes there. If they've got a lawyer that they want to get involved into it, we welcome that. As part of that product that we sell, we have a weekly call where people can come in and they can ask questions of me. It's like office hours, and they can flush out their strategy. They can flush out If they want to go into a professionally managed deal, they can invite their CPAs and their attorneys and their professionals into that weekly call with me. That's also available if they just want to join that mastermind, right? To get the access to that kind of strategic level thinking. And so we are specifically there in order to handle whatever they don't have, right? If they've got it covered with a different professional, totally fine with that. If they don't have it, we've got somebody that can step into that role. We've got accountants that we work with. I am an attorney, so we handle the setup and we handle the documentation on things. We've got individual deal where we can help find them deal attorneys if they need a local attorney to actually affect a real estate deal or whatever that looks like. We don't do the actual closing of stuff, but we can walk people through how to do it and the best way to do it to make sure that it's Opportunity Zone compliant. And so, we're regularly working with their local council, their real estate lawyers, their CPAs, their other financial advisors to make sure that what we're doing jives with what their bigger picture ideas and objectives are.

Excellent service. So, looking across everything you've seen, what's the biggest mistake people make after a big win? And what would you want them to pause and consider before they move forward?

The biggest one is that they don't do it inside of the 180 days. They don't come and talk to me. And if they blow the 180 days, unfortunately, there's nothing I can do about that. And now if it came off of a partnership or an S corporation, we can start that 180 days not with the date of the sale. We can either start it on the year end or we can start it the next March 15th. So we got a little bit of wiggle room on that where we can go back all the way to January of 2025 and pick up a capital gain if it came through some kind of partnership or S corp. But that 180 days I think is the biggest one that we see people blow. And a lot of times it's kind of analysis paralysis, is that they're like, okay, I've heard about these, but I want to know everything about it before I jump. And that's what we specialize in, is helping them get something that's comfortable for them to put their money into. Because a lot of times maybe you're not going to be able to do the due diligence on individual deals and professional sponsors and that kind of thing inside of that timeframe. We specialize in helping them get their own fund set up in their own bank account so that way they could literally just moving it from one pocket to the other. They control it. They're the master of their own destiny. And accordingly, we've now deferred those taxes and we've made it eligible for them to go into an opportunity zone deal. Now, I've also had people that have done that and then they haven't been able to find a deal. So I got people this year that haven't been able to find a deal. They've looked for 'em, they've done their due diligence, and they're like, listen, man, I just can't do this. I can't get comfortable with opportunity zones. Okay, well, just distribute the money out and now you're going to pay the taxes in that year. There's no penalties, there's no back taxes because you've actually done something with it. You didn't just use this as a tax avoidance scheme, right? You actually looked at it and you did all of the things that you were supposed to do. And we helped them do that. And it's kind of like no harm, no foul, right? Like, all right, well, I can't do that. And I'd say that that's probably the serious exception because as people They put the money into their fund and then they're like, okay, now I need to start, now I got some time and some ability to be able to look at this. So walk me through a difference between an opportunity zone deal and a non-opportunity zone deal. And so then they go in and they actually look at those deals and I'm able to kind of get them past the preconceived notions that opportunity zones, I hear this all the time. Well, the whole reason why there are opportunity zones is because they're bad areas with bad investments. That's the reason why there's a tax program. By the way, that's how the naysayers talk. And I'm like, no, that's not the case at all. There's 8,700 of these things, including beachfront property in Myrtle Beach, lakefront property on Lake Adger. I mean, it's amazing some of the real estate plays that are out there under 1.0. And I think that we're going to see the same thing happen with the 2.0 designations, that there's really great places that people can go to invest. And then I'm also able to kind of get them outside of the box to say, hey, listen, this isn't just a typical 1031 where you're going into another locked and loaded real estate deal. Let's get outside of the box. You sold your business. I know you've wanted to do this other business. So let's create that as an opportunity zone fund, as a qualified opportunity zone business. Let's capitalize it with your capital gains. And now let's position that so that your next 10 years of growth up to 30 years are going to come out tax-free.

Can't pass that up, I would think. But yes, people do have strange ways of thinking sometimes. So thank you, Ashley, for being with us today as we have talked about opportunity zones not as loopholes but as a framework for design. We've seen how a liquidity event doesn't need to trigger rushed decisions. It can be a moment to redeploy capital through thoughtful actions that reduce taxes legally and align strategy with real-world outcomes. We've also explored what it means to think like a family office, not in terms of net worth, but in discipline. So timing matters, structures matter, and audit readiness matters, and impact when paired with rigor can strengthen returns rather than diminish them. Than dilute them. For those who want to go deeper, Ashley and his team have created a dedicated resource for Streams to Impact listeners, and you can find that in our show notes, but I'll just read it out here for you. That's at www.ozpros.com/podcast?podcast Underline show equal streams to impact. You could learn more at that site. Once again, that will be in our show notes. Enlightened investors, thank you so much for being with us and spending this time with us today. If today resonated, especially if you're navigating a gain, an exit, or a moment that calls for thoughtful redeployment, I hope you will consider Visiting Ashley and his team. And also, I hope that if this conversation helped you slow the decision down and design it well, that you will continue to explore how high-achieving professionals align capital with long-term stability, prosper, and impact. So, I invite you to our Beyond the Paycheck: The Financial Clarity Compass. This is a private educational experience and it's our gift to you and you can claim it at www.go.steedtucker.com/beyond-paycheck. Until next time, stay grounded, stay disciplined, and keep building wealth that serves both people and purpose.

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