WIN180. The 5 Pillars of Smart Private Real Estate Investing with Spencer Hilligoss
- AJ Shepard

- 2 days ago
- 45 min read
AJ: Welcome to the Westside Investors Network. WIN, your community of investing knowledge for growth. This is the real estate professionals investing podcast for real estate professionals by real estate professionals. This show is focused on the next step in your career, investing. Thank you for listening.
And please, if you like our content, rate us on your podcast provider. Just a quick disclaimer. The views and opinions expressed in this podcast
Spencer H: are
AJ: for educational purposes only and should not be construed as an offer to buy or sell any shares or securities to make or consider any investments or take any other action. Alright.
Welcome, guys. I wanna welcome, Spencer Hillegoss to, our podcast today. Spencer, thanks so much for coming on with us.
You know, we know that you've got a lot of experience in, investing in, private placements, and just interested to hear your story. Do do you wanna start off by just telling us a little bit more about yourself and kinda what brought you, to this point in here?
Spencer H: Yeah. And it's honored to be here, guys. I'm glad we could figure this out. I lead Madison Investing, just a private investing club that I invest in and run, but it wasn't always that way. I sit here in Alameda, California.
It's like a little island community tucked between Oakland and the and, San Francisco Bay area. Got two boys, young kids, 11 and eight, and, I founded this business along with my wife and cofounder, Jennifer. And so that's a whole kinda separate podcast on starting a business with your spouse. We love it, not for everybody. You know?
So I was in tech companies and have been in tech now for coming up on fifteen years. And so a lot of these have been, like, fintech finance tech companies, like Intuit, Xero, Gusto, Kiave, Stripe. Before that, I grew up in a real estate household. My dad was a broker, so he was a real estate residential broker for thirty years. He was having me do open houses and clean out fridges for properties he was trying to sell and stuff that I thought at the time was so lame and so boring and not cool to tell anyone, and that's why I went into tech.
And so I I in hindsight, you know, I don't know about you guys, but the universe kinda pulls you back into the stuff that your parents led you to sometimes. And, apparently, I had to get over that and get more comfortable with it before I could come back around and realize, oh, there's a good reason to be involved in real estate somehow. So
AJ: We we just embraced it. Our our dad was in real estate, and we went right out of college just right into investing.
Spencer H: Yeah. Hey. Good on you. Served you well. Right?
And so, I mean, for me, I I didn't I mean, besides buying our home, we got very lucky. We found a, an up and coming market where we bought our first home in 2013 before it got really hot, built some equity that also allowed us amongst our own savings in the corporate world to start buying some rental properties. You know? And and in hindsight, I don't know about you guys, but like entrepreneurship and investing is clear as mud, like when you're going through it sometimes. Like like like, I don't have some crystal ball.
I don't have all the answers. I just know like the figurative machete we have to pull out sometimes to find clarity.
AJ: You know? Or even just choosing the right machete for that task. Right?
Spencer H: For the job. Yeah, man. And so I look at, like, twenty sixteen ish is when we started to invest in rental properties. And we just wanted to go and find the off ramp from this grind of the tech culture. You know?
I was waiting for the Silicon Valley lottery to somehow pay out the next Google IPO, Uber IPO money from one of the five companies I've been at. Thankfully, one of them hit, but I think, it doesn't usually work out that way. You know? And and so we were just grinding and, you know, raising a family with young kids and and trying to find a way to get some relief as we're getting promoted and fewer hours available to be a present parent. And so we bought a rental.
The first one we got, $430,000 purchase price in the Bay Area for $200 a month in cash flow. That's not exactly life changing. But it's appreciated since then. You know, you ask anyone, I know, AJ, you said you've lived in the Bay Area before, but I was happy to break even. So, you know, you buy a rental in the Bay Area and you're like, you're just hoping to pay off the mortgage and the and the insurance and and all that.
But we eventually found our ways into buying long distance rental properties, and that kind of led us to investing in private deals as well. So long story short, it's been a wild ride, and I'm very grateful for it now because it still is like a fundamental pillar of our wealth building strategy as a family.
Chris: Nice. So Spencer, when you said that entrepreneurship and investing, I was thinking you were going another direction and that those two hand in hand together are just phenomenal tools like building up a business that's creating income and then investing and receiving huge tax benefits from real estate as opposed to it's just like so murky and so difficult to I mean, the decision making and the strategy and the execution part of it is always so difficult, but the payoff aspect of it as well is for somebody who can wade their way through all of the murkiness and the tough decisions and just making the decision to continue you know, there is big payoff. So
Spencer H: Absolutely. Absolutely. Well, and and to that end, I mean, it has to be mentioned. For example, like last two summers, Jennifer and I did something we wanted to do with our kids for our whole lives. You know, we wanted to break the mold bit.
We went and lived abroad for six weeks in different countries with with our kids. Last year was in Croatia, Montenegro, which admittedly I had to look up on a map. The year before that was Portugal. And so, living in these different places was only possible to your point because of the of what investing in entrepreneurship has enabled. Right?
And we're we're not doing they didn't do that this this summer, in particular, but, like, those types of journeys have been made possible because of entrepreneurship and investing. And and and I appreciate you kinda honing in on that, though. You know, the, what I wanna get across with it is that, man, I read 400 books when I got into this. I mean, 400 podcasts rather and 18 or 19 books in my first year when I got into this space, like way over the top on education, way more than anyone needs to do.
AJ: That's that's a good amount.
Spencer H: Yeah. But but I I think there are paths forward. And there and a key part of that is just connecting with other people in the space such as yourselves and going to meetups and listening to to people who have had these experiences because I wouldn't be sitting here unless I was able to learn from those who have come before me. Right? And so, it it's a path worth walking to your point.
Absolutely.
AJ: Well, and, you know, thanks for kind of giving us the the little bit of the past, but, I mean, why don't you tell us a little bit about what you're doing now?
Spencer H: Yeah. You know, gosh. We're at the very beginning of 2026. What a different year than it was. If you look back to maybe, what, 2021.
Right? Like, really hot market at that time. Flash forward, you've gone through a few years of high interest rates. You've got some interesting volatility going on. And right now, we're looking at opportunities to invest still.
The asset classes I've historically liked have been multifamily, have been, you know, sometimes in self storage, mobile home parks, medical office. So we're still investing and looking at deals. I I I think right now, we still look at the same five part vetting framework that we put together, that Jennifer and I put together when we're vetting a new sponsor and taking a look at a new deal. Same one we did then, but I'd say our our pencils are thoroughly sharpened relative to what we first got into this because it's been a there's no way to sugarcoat it. It's been a challenging couple of years.
Right? We've had some deals that went really well. We've had some deals that went very poorly. And, that's paying tuition in painful ways sometimes. But I say all that, like, hey, we're still here and we're still doing it because it is so worth it.
And so the five part vetting framework is simple. It's like, look at the team, track record, their approach, communication, and their values. And it sounds nice and tight with a bow, but there's a very nerdy 70 to 75 row spreadsheet with questions beneath this thing. And so we're not gonna go into all that, but you gotta know who you're investing with. And and you really gotta take the time to get to know that they've done it before in some way, shape, or form.
And they've faced headwinds, man. You don't wanna necessarily park a $100,000 or $50,000 or more with someone who is facing the first challenges in the market ever with your money. So so there's so many different ways to to kinda, you know, vet and and take a look at their their performance historically. But, yeah, happy to nerd out on that in whatever way might be helpful.
AJ: Yeah. Well, I mean, I guess, I'm just gonna kinda ad lib this here. You don't know us very well. I mean, do you wanna kind of take us through I mean, I'm not saying the 70 questions per per thing or anything, but maybe a couple of the questions in each of the, framework?
Spencer H: Yeah. For sure. And there's a couple that relative waiting, have to put a bit heavier. You know, the the phrase track record, we gotta start here with that one. What does track record really mean?
And I take a look at some of the deals I invested in in past years. You had a great looking IRR, the average IRR, you know, internal rate of return for some of these deals. Pull up the hood and you're like, well, this sponsor had some amazing exits in 2021, 2020, maybe first half twenty twenty two, and good on them. They caught the timing, and they did their job. They operated well.
Well, what happens though if you take away those really strong positive tailwinds that were happening in the economy at that time and for interest rates. We were in the ZERP period. Right? The zero interest rate policy period. So when money's not free anymore and you're actually going out and seeing some challenges like higher insurance, higher taxes, property taxes, you know, just supply, oversupply in the market.
When I see track record now, I wanna see that coupled with approach. And what that means very specifically is like, okay. This team has done it before. Have they done it in the same asset class? And have they done it perhaps even in that same market?
And how well do they know that market? And I think about, you know, I'm a big obvious, like, guitar nerd, like, music nerd. If I were to to pull out the comparison point, it's like, if someone has been has been able to operate an asset, buy it, operate it, improve it, whatever that business plan might be and sell it at a profit, they should be able to articulate that in exhaustive detail and show that on paper and somehow. Same thing if I'm working and learning a guitar solo or trying to hacking through it, I'm not that good. I I should be able to articulate, here's the steps that I took.
Here's how many hours it took. Here's here's the the lessons I followed. Here here's all the different things that I practice, the different chords and modes and all that stuff. And so nerdy music aside, that that's gotta be the first one. You know, it's like, gotta pull up the hood more.
Track records look great. How do they achieve that track record is arguably the most important thing. So that that's probably the first one to call out.
AJ: How do so do you do that just by, like, talking with the GP? I mean, I guess, like, functionally, like, how do you go about that? Because, I mean, presumably, they're putting their best foot forward. The track record is usually a marketing piece. Sure.
Right? So, like, how do you how do you get under that hood?
Spencer H: Look for the, reconciling what is stated upfront for the pro form a on just the financials. You know, lot of it comes down to looking at sources and uses. K? Like, what is the financials that were said they were gonna be deployed? So perhaps the sponsor raised capital, go buy this asset, and they had a business plan.
They're gonna take the funds, allocate them, deploy them to achieve that business plan. If they did that, how did it go? And you can in practical terms, you can actually ask for just, well, let's look at all at least a reasonable sampling of all the different investor updates and the financial updates that went out throughout the whole life of that plan. You know, you don't have to look at all. If you're sent they're sending monthly, monthly, that's a heck of a lot of them.
Right? I'm not gonna ask for a five year 60 different emails, but I will ask for a pretty good chunk of them. Quarterly, little easier. But is you just wanna see, like, what were the facts that were being communicated? Ideally in the financials and the operational performance.
You can see that with the t 12, the the rent roll. You could see that with, you know, the operational performance. You could see anything that was, like, unexpected CapEx that had to go out. And then how did it sell at the end? Like and was the exit strategy that was performed?
Like, when they sold that thing, was that the original plan? Was that to to the buyer profile that they were even going for? You know, just all those different nooks and crannies can be can be, evaluated in hindsight much more easily because you can just pull the information. And if they don't wanna provide it, that's a red flag.
AJ: Right?
Spencer H: That'd be the first one. Yeah. I think the second one would be if you look at there's behavioral interviewing and, like, one of the things that I would pull on from the corporate world, this is not rocket science and you guys will probably, you know, be well familiar with this. But, like, if you're asking someone, hey, tell me about a time when. And, you know, I've done this with, like, interviewing for leadership roles in the corporate world and applied it to real estate plenty of times.
But, like, if I wanna ask someone, hey. Tell me about a time when the deal didn't go well. Like, what happened? Did did did something go awry? Was there, like, an unexpected expense that popped up?
Was there damage to the building? Was there a new regulation that was passed? And if, if the sponsor is basically saying like, nothing happened. Like we've never, we've never dealt with that challenge or we've never had a serious headwind. That's one of the biggest red flags possible in my mind.
You've basically got a scenario where someone is saying, oh, this is like like we're perfect. I'm like
AJ: because everyone is. Right? Everyone's perfect.
Spencer H: It's like this that doesn't exist. Right? And and we were talking about this a bit offline ahead of time, but like, we've all invested in deals that have gone far from perfect. And even on the good ones, like, the first deal we ever invested in personally was a multifamily deal in Alabama, and it ended up being a great outcome two and a half years later. Right?
It was like a 2.3 x equity multiple.
AJ: Yeah. I guess maybe circle back, like, what time of the market cycle was that? Like, kind of what years? I mean,
Spencer H: because it's not 18.
AJ: The last three years are significantly different than, you know, ten years ago.
Spencer H: Yeah. Of course. Right. So as yeah. I appreciate you asking that, AJ.
So, like, I I have zero expectations for current investments that I'm making right now to go full cycle in two and a half years with a 2.3 x equity multiple. Maybe they're out there. Some some of them, they are really, really good deals can be found. But this first deal we invested in around 2018 like that, it was a tree falling on one of the buildings. So was a two property portfolio in the first quarter of ownership, which paused all cash flow.
And we're like, well, we made a huge mistake. And then lo and behold, sponsor handled it really well. Like they not only fixed it, addressed it, was very transparent about it, pulled all the levers they had to. And then ultimately, we got our money back and then more than twice as much at the end of it, you know. So like What what help timing in addition to that, of course.
AJ: What what gave you the feeling that the sponsor handled it well?
Spencer H: The speed with transparency and their plan. You know, I I think something bad happening, that's just part of life and business. Something bad happening and then having it communicated with wild transparency done quickly, that's great. Know, everyone's an adult here. We we just wanna be communicated too transparently.
And I think that that was the big first step, AJ. Yep. Second one being, here's here's what we're gonna do about it. Kind of the same principle. Like, I I remember being in, like, my first or second management job in the corporate world and, like, leading people, and I felt weighing over my skis
AJ: because I was.
Spencer H: And and my boss was like, don't ever come to me with a problem without a plan.
AJ: Yeah. Without yeah. We tried to tell that to our employees too. It's like, you you don't get to dump a problem on us. You need to have two or three solutions when you come to us with this problem.
Spencer H: Right. It sounds fundamental, but it actually is is super common in a lot of the deals that I mean, I mean, some of the deals rather. You invest in it and you're like, okay. Got it. So so there's this problem of an act of God or a, maybe a fire happened or or oversupply or whatever, macro micro across the board.
Right? And and that's stuff happens, man. But how we choose the path forward, that's really what it's all about.
Chris: So you touched on communication and speed of communication. I mean, when it and you also mentioned monthly updates and quarterly updates. I mean, do you have, like, an expectation of what what is good communication versus, you know, what's not good?
Spencer H: Yeah. Gosh. I appreciate you asking that one because it's evolved so much. I used to put a premium on you know, I I think a lot of folks from what I gather, you know, I've talked to hundreds of LPs over the years now. And I I used to put a premium on monthly updates and monthly distributions.
I don't care about monthly distributions and updates. I really don't. What I care about is good ones quarterly. And good ones quarterly with transparent, professionally packaged financials. Full stop.
That's it. Like a business update with financials. And that's that's really the gold standard for me now. It's a if a as a sponsor can clearly articulate without having like a five page novel, you don't need to have a ton of verbiage. What you do need is the facts.
And the facts are usually told primarily through the financial lens, but also kind of like a strategic level update. Like, here's the big points that need to be stated. And and and then that's really it. Right? Because in the end, you know, there's one or two sponsors and and, you know, bless their hearts, I've gotten to know them over the years.
They will write a five page novel without just saying, I'm sorry. Your distributions are paused. They will not be resuming. We might never turn them back on. We're gonna sell the asset eventually, and maybe you'll get your pref caught up.
That like like that that's a hard message. But in that one example, I'm using an extreme one. I would much rather have the sponsor tell me that, as opposed to saying, hey. We're doing all this fluffy stuff. Hey.
You know, like, I I do think it on the values front, one of our five part value one of our five part, betting framework is values. And sometimes that comes across as really squishy. Right? And I think it's it's not squishy at all to me because what I what I mean by that is at the same time, I know we're all capitalists, we're investing for, like, we're investing for profit. However, it does still matter to me that like, if we're investing in something that builds wealth so effectively as all these wonderful private investments that we make, I still expect like the people living in the buildings to be taken care of and provided a good living community.
And so, you know, I also wanna make it very clear that like, yeah, I've asked a sponsor before, like, what was your philosophy on on tenant experience? You know, I don't need someone to have some perfectly worded whatever plaque that they put on a wall, but I hope that they would at least think about it, and at least have put something on paper to talk about it. And and this one sponsor who made it through every other hurdle of our vetting process kept dodging the question. And, ultimately, we weren't able to work with them, and we weren't able to invest with them. But I just bring that up to kinda couple it also with, like, the tougher talk of, like, man, I wanna see those financials because that because both things are true.
It's like, you know, just state state the facts. If stuff's going well, state the facts if stuff's not going well, and at least prioritize the people that are gonna be living in the asset. It's a little different with self storage because there's no one living in the units, hopefully. Right? Let's hope.
Yeah. Let's hope. But like in multifamily, yeah, there there's real human beings living there and it matters to us.
Chris: So you you touched on, you know, verbiage and then financials. When you're evaluating quarterly update and or I guess when you're evaluating previous deals that a sponsor, where they're giving you the quarterly update with the financials, how are you reconciling what what they're saying in their words and then what is on and then I guess what what type of financial reports do you really want?
Spencer H: Yeah. You know, nothing too innovative, frankly. Just the basics and the basics I and you guys will keep me honest on this one too because I'd be curious to hear yours as well. For me, it's just reconciling the the initial pro form a. Well, you know, the Excel spreadsheets that actually state, hey.
Here's here's what the plan is by by year, by quarter. I mean, if they did it by monthly, cool, but sometimes just stuff just stuff changes as you guys know. Right? So if it's you don't wanna get too granular where it's unproductive, but I would say some initial business plan pulled out, extrapolated over the course of five years, if it's a five year hold, ten year, because you wanna have some contingency plans hopefully. And then take a look at reconciling that with whatever financials have been, you know, made available on the way, you know.
So so just, you know, p and l, like profit and loss statements, you know, income statements, all all that good stuff to be able to say, is that NOI on track for where we expected it to be by the end of year x, you know, year two, year three, year four, and y. You know? And it's just those two things at a at a high level. Like, okay. Are the are the dollars and cents making sense?
And and and if so, how come they're they're they're going well? Is there it's okay if it's not perfect. There's never been a perfect forecast in man in human history. Right? Nothing ever hits exactly a 100%.
It's gonna be high or low or somewhere in between. But, as long as it tracks the on the story and you can reconcile that with the numbers. But does that answer your question, though?
AJ: Yeah. I think so. You're I mean, you're just taking a basis of the pro form a and comparing it against, you know, the whatever t 12 that they have or if it's a quarterly report, you know, what they made in the quarter. Like, I guess, I mean, like, certainly there's variances that are along the way. Like, what are are you looking at that for your current investments or is this just, like a project that you do when you're evaluating a new sponsor?
Spencer H: Yeah. I mean, really, we're looking we're spending a lot of our time more so on on new potential deals. Right? Of course, after you've it really comes down to, like, once you establish that trust with, a sponsor you're happy with. Like, the deal's going well and you you've ideally exited other projects with them.
Right? I mean, we've already exited a couple dozen, across the different sponsors. And ideally, we're gonna be looking at those less mid flight once we're getting into the second or third deal with that same sponsor. And it's already it's already been purchased and they're working on the business plan. So, yeah, we're spending most of the time, AJ, out on looking at the new deal, new deal flow and just trying to find stuff that's gonna be really good.
Chris: I mean, there's not really much you can do after you send the money and sign the PPM.
Spencer H: But That's exactly right.
Chris: You know? It I mean, it's it's not necessarily at some cost, but
AJ: if you're contemplating, you know, investing more money on another project, like having that information probably would be, you know, something to look at, know, are they, you know, within a couple percent of their, NOI? Or are they, you know, you know, way above or way below? And then, you know, on top of that, is it a result of market conditions, or is it a result of, like, actual operations?
Spencer H: Yeah. I mean, I think you're hitting on a really great point. I was just having a conversation with another LP I've gotten to know over the last couple of years this morning about this, which is like, he just invested with a sponsor that both he and I have been looking at for a while. And the sponsor reached back out and immediately said, like, we're talking, like, two months after he had made this first investment. They reached back out and said, hey, we got a new deal.
You wanna take a look? And he was just sharing with me. He's like, man, I'm not ready for that yet. Like, we're they they just closed on the property. Like like, we don't even know how the last one went.
And they're coming back and saying, come and do the next one. And admittedly, I've made that mistake. You know, I've made that mistake where I was so excited about the deals on with the first, deal with a new sponsor years ago. And I was like, k. Let's go into the next one with them.
And then I look at what has happened with that sponsor, and I'm like, should've waited. Should've waited. You know? Because time time tells you a lot. But
AJ: Yeah. And I mean, even if they have a substantial track record too. Right? Like, it's getting up on their cadence of how they do things. I mean, if they've been in the business twenty, thirty years, there's a few players out there, but I know that they've had some real struggles in the last three years as well.
So
Spencer H: For sure. The established ones and the the emerging ones. Right?
AJ: Yeah.
Spencer H: 100%.
AJ: I I kinda had a question. Like, your five part framework is very much geared towards the sponsor. I mean, how much weight do you put on the deal, compared to the sponsor? I mean, I I think we're we we've all heard the saying of, like, a bad sponsor can turn a good deal bad. And, you know, a good sponsor can take a bad deal and, you know, do okay.
But, you know, certainly, like, I imagine it's definitely weighted on the actual sponsor. But, like, I guess, you know, from your personal opinion, like, what how do you look at markets?
Spencer H: Yeah. I mean, you you took the words out of my mouth in the best way on that one, AJ. I think and truly, like, thankfully, the filtering gets a lot easier just because you don't have to go any further than the sponsor level most times. You know? So you start there.
So you're waiting over 90% probably. If I heard to put something quantitative into a pretty pretty qualitative question, but, like, under out of sponsor market and deal, over 90% of that goes on the sponsor. Yeah. Then you get down to the deal. I I'm fairly open minded on markets.
Just to briefly comment on this, I I feel like the places I haven't dove into, so I it's more like, I I guess I'd be open to them, but I haven't done it yet myself, our primary markets. You know, like I haven't I haven't invested in something that's in Downtown San Francisco or Downtown New York or Chicago. You know, the I I I don't know about you guys, but, like, I'm open to those. I just haven't necessarily gone deep on them. So we've largely looked at secondary and tertiary markets.
AJ: Yeah. I I mean, I think, you know, some of those are few and far between too. Right. You know, the product to that I mean, we're in Portland, Oregon, and we're doing deals here in Portland, Oregon. And, a lot of the product downtown is 100 years old, and you're not doing a full renovation on it.
It's more of a yield play and construction costs are way up. But we don't see too many of those deals.
Chris: Or you're doing new development.
AJ: Yeah. A new development, super risky comparatively to the space that we're in, which I think is kind of like a misnomer too amongst LPs. See that you know, bump in IRR, but it's hard to measure the risk associated with that.
Spencer H: That's right. Oh, man. You just you hit on one of the most common topics that I feel like I'm obligated to get into with new LPs all the time. I don't know about you guys, but, like, when I'm and I'm asked, like, hey. What do you think about this deal?
I'll I'll get into that with with every LP that I talk to. But the first question I come back with is, what's the goal for the money, man? Like, what's the goal for the money?
AJ: You know? Number one goal is preserve capital.
Spencer H: Yeah. Absolutely. Right? And so assuming that we're all in here for the the primary goal of let's preserve the capital, then is it are you trying to grow it? Or are you trying to just generate a cash flow from it?
And nine times out of 10, I don't know about you guys, but the same sentiment is usually shared at this point, which is, I don't know, a little bit of both. And it's like, cool. If that's the case, by when? You know? So just kind of pulling back on those those the ever deepening why questions, like, okay.
And I I I need this reminder too. Like, my lizard brain kicks on hard when I'm looking at a beautiful looking investment summary still. And I say, wow, that 25 to 30% IRR seems really sexy. So it's like a
AJ: new building the new building looks sexy too, doesn't it?
Spencer H: Absolutely. Yes. It's like it's all shiny and new. It's not one hundred years old. It's not like most of the properties that we all look at in, the Bay Area down the street.
You know? But I I I think in terms of just goal setting, it's it's very grounding to just kinda say, okay. We all wanna preserve the capital, but do we want this money to actually grow? And do you even need the income? Is because everyone kinda is conditioned to say, I want the cash flow.
And I ask an Apple engineer who makes $400,000 a year, been in that job for eight to ten years, has two kids at home and generation living with them and a floor above them, and they're trying to not leave their job right away. They're not trying to quit the rat race. They just want to continue growing their wealth and provide a cushion for the years to come. They don't need cash flow. It doesn't change anything in their lives.
What they want is their capital to be there at the end, and they want there to be a nice equity multiple on the other side and to be able to tell their friends they've invested in a big real estate project. And I'm not being facetious, like that's nine times out of 10, that is really the the check boxes that folks are often looking for, you know. So I I I digress, but I just wanted to at least share that, like, that that is super duper grounding for myself still just to be like, hey, why am I evaluating this? Is this gonna be a cash flow play? Am I trying to hit a cash flow number still, or is that something that we're not we're not begging for this year to be a goal?
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Chris: Nice. And so I guess when you're talking about value add versus new construction, how, like from our perspective, new construction is extremely risky just because of permitting zoning, construction delays, etcetera. Performance, performance.
AJ: And lack of lack of income.
Chris: And I guess I'm interested to hear your take on it. What do you think about a new construction?
Spencer H: Almost identical perspective. I have invested in terms of single asset deals that I've invested in, it's it's always been there's been a building there. It has an address, and there's a building. You know, I think there I have invested pretty significantly into some funds that might be, blended with a percentage of new build. I I can get comfortable with that, but it's not the majority percentage.
You know, it's, you know, one example or two examples I'll share would be in self storage, like invested in some funds where it's like, okay, cool. Most of these are established in markets that are not oversaturated, not expected to be oversaturated because of overbuilding. And there's like one or two new new facilities that are gonna get built. Cool. Out of like 15 plus to 20, I I I can get down with that.
There's a good risk balance there. You know, if if you're looking at like multifamily, kind of same story which is like if they wanna build some new stuff in a in a blended fund, most of the other buildings already need to be there, you know, and operating a cash flow positive, all all those those basic things. So I'm right there with you on that. I I I'm not, maybe that's just me. I know some folks like to shoot for the moon and they like to go for those those, you know, three x equity multiples and and see their money come back if it were if it goes well, you know, knock on wood within, you know, a three to five year period, awesome.
It's it's not me.
AJ: You know, you kinda touched on the the fund aspect and blended funds and single assets. I mean, how does that come into play when evaluating the sponsor? I mean, I'm assuming that's, you know, evaluating the deal, and it sounds like you've invested in both. Do you
Spencer H: have a
AJ: preference of of either one, or do you find one to be better than the other? And, like, from your opinion, like, what are the advantages?
Spencer H: Yeah. Gosh. I mean, I don't know about you guys. My my philosophy on this has evolved a lot in the past five years and largely because of some of the the wins and some some of the tougher learnings along the way depending on single asset versus blended fund. I think that the my appetite for getting into a blind fund when the sponsor says, here's our big plan.
We don't have any assets necessarily closed, but here's what we're gonna go buy in the next five years. I used to be more open to that until I've kinda seen some sponsors do that really well, some sponsors don't. We'll just leave it at that. You know, the the confidence to say, okay, I believe in this sponsor because I've exited deals with them has the has been the only time that I've been confident necessarily diving into, a multifamily fund like that and and seen seen the positive results already from like, okay. Wow.
They they exited that deal. It went that well. They ran their plan. I think they can pull this off, based upon what I've seen. Otherwise, I would say that kinda shift gears for like who is a fit for funds and who thinks that they're a fit from an LP lens.
This is a bit counterintuitive. You know? I don't know if I don't think it's contrarian to say in 2026, but, you know, but since you asked, AJ, like, I I would say that oftentimes folks who want cash flow from their deals in multifamily syndications and funds, oftentimes they're the first ones to say they only want to invest in single asset deals. And I think that that's an interesting perspective, because single asset deals, they could be the home run. Oh my god.
It's wonderful when that happens. Right? You invest in an amazing deal, it goes well, sponsor crushes it, Cash flows along the way and exits really well. When reality hits, sometimes it's nice if you want smoother cash flow to have five to seven to 10 different assets in a single fund because if one of them doesn't go well, the rest can still provide positive cash flow. So for the investors who like to do larger investment amounts and they're investing with a sponsor and it's actually like a really good track record, they got a great investment thesis, they've got the right management structure, operations look good, Sometimes the fun can be great.
It really just depends on what they're trying to solve for, you know. And I think that that that didn't used to be my perspective. I would say that I used to be much more keen to say single asset deals are bust. And and so many very, very new LPs will only ever ever look at single asset deals because their head kind of explodes from the concept of thinking about a five to seven to 10 asset fund of any type because it's confusing. But, yeah, I I still believe that there's a time and place for a good blended fund with a very experienced operator who's capable of managing funds.
AJ: Yeah. I mean, we've we we started syndicating probably about five years ago, six years ago now, and we have only done single assets. But I mean, we've talked about the potential of doing a fund. And maybe I'm just kind of curious from your experience and talking with significant amount of sponsors, which sounds like you have. Do you have a sense of the progression a sponsor takes to, you know, get to the point of, you know, having a fund with, you know, five to 10 assets in Yeah.
Spencer H: At least the ones that I've seen that where it went well, they tend to have, you know, at least, you know, I'm using this very broad strokes, but like, you know, half a dozen to a dozen exits already before they kinda go for that. I I think that is the right general trajectory. I mean, who am I to say the right one? There's so many different sizes of assets. There's so many different flavors of success.
Right? Like, mean, winning can look so different depending on the size of asset. There's a a really great team that I've seen that is buying, you know, around fifty fifty door assets. Right? Like like great size, you know.
It it it doesn't matter if, you know, another sponsor who focuses on 200 units to 300 units and up will go and launch a fund because they think that they can do that, add five to seven assets into it and they've already got a green track record to go do that, totally apples and oranges. Right? I I I look at that like you have to just take it in the context of the size of asset in the market that they're gonna go execute in because someone's buying a smaller property and and they wanna go all of a sudden go buy a 500 unit in, you know, Dallas, Texas or, I mean, DFW, like, you you gotta stick with what you're good at and hopefully the fun that they're trying to launch or someone is trying to launch is still focused in their same core buy box and criteria and business plan that they've already done. In which case, then my confidence level is gonna go up. It's it's it's when people try to try to jump lanes.
That's when my, you know, that's when my back gets up. Is it's like, oh, so you guys are trying to buy something totally different than you've ever bought and that's what your new fund is about.
Chris: It makes you wonder why.
Spencer H: Yeah. Yep. Yep. Yep. I mean, similar to, without going too far into it, some of the funky stuff you see out there in the past three years, you know, when a sponsor puts together a pref equity fund or preferred equity fund and they suddenly got into that and they've never done it before and they've never done any debt or equity, did private credit or private debt stuff and suddenly they're really good at that.
You know, it's those things raise my eyebrows.
Chris: I mean, I guess my take on that would be is that they have significant overhead and they need to keep transacting to continue the business that they built.
Spencer H: I would agree with that assessment.
AJ: Yeah. It's more of a necessity to exist, which means you also strip potential returns out of future investments, I guess. I don't know. I I'm gonna change not change the subject, but kind of still along the lines of, like, evaluating a sponsor. Like, what sort of stock do you place in a sponsor that's vertically integrated?
Spencer H: Gosh.
AJ: And is it is it a plus? Is it, you know, a minus?
Chris: Well, how do you evaluate it? Yeah.
Spencer H: Yeah. Yeah. I I think this is a very fun topic to talk talk about, honestly. Because now having seen what happens when it I've seen both work. That's the bottom line.
I've seen both work. Ideal case, they're vertically integrated and they know what that means. The challenge happens is when they think they need to be, they go and do it to then find out they don't want to be and then you're screwed. And I've lived through that. That's not fun.
It's very expensive for everybody involved. So without being preachy, I'll just say, I I think third party is a fine option for a sponsor that knows, like, who who they wanna work with to have a third party management firm. That's great. I've seen that work what really well. And I've invested in deals that have gone full cycle, and and that was the playbook.
And they solved for that in their pro form a, and and they ran that business plan, man. They're very self aware about it. More power to them. It's more cost effective and more effect it's it's in general more effective if the sponsor is vertically integrated and and they know how to do that. And so it's about a tool.
You know? It's a I look at it like from a really high level and everything else in business, it's a lever you can pull. It's a tool in your tool belt. If you pick the wrong tool or you don't know how to use it, you're gonna be in hot water. And so ultimately, just just choose wisely.
Chris: I'm interested in your thoughts on third party management and how it can be successful. I mean, I know that there are many, many, many cases where it's successful and that third party just does a fantastic job. And so I'm interested, like, how do you know when that's going to happen? And then how do you know when your,
Spencer H: I
Chris: don't know, spidey senses are kind of.
AJ: Spencer, I'm going to give my take on this before you give us the real answer. But my sense is that you probably wouldn't want to invest with a sponsor when it's their first time with that property manager. You wanna see a historical relationship with them.
Spencer H: You did take it out of my mouth. No. You're exactly right. Right? And, I I mean, to expand on it though, the like, what are the benefits?
Because I think I think your question is a great one about when it works, like, why does it work well? There are certain competencies that come along with doing this well, and and these are things that folks can very much built in house and they and they do build in house. So much of it comes down it sounds simple guys, but like, I don't know if you've experienced this, professionally packaged financials. Like, this is like, can they can that company translate what is happening with, you know, fixing a broken door on the 2nd Floor of Building 1 and explaining that was fixed on this day and somehow translate all of that into a reporting infrastructure, translate the expenses put toward repairing that door, and then multiply that times a thousand other things that just happened on that throughout that month. Put that into a professionally packaged infrastructure for reporting because in the end, where it falls apart utterly, I mean, is when, it's you don't have a dashboard.
You're flying blind, man. And and I feel like so often in business and in real estate and in life, we just have to know are things in the green and the yellow and the red. And, definitely have seen what happens when all of a sudden, you know, you're multiple different quarter, like three to four quarters in and suddenly, sponsor says, oh, we just found out blah. And that blah is a five digit repair number on a on a on a relatively small building. And you're like, yeah, that water heater needed to get fixed, like, six months ago.
And why was that not identified earlier? Well, it's because their operations are not tight. And so I'm using a really nerdy, very specific example. Yeah. You know, there's so many other ways that we could skin that cat, but, you know, you gotta gotta know what like, what's on the dashboard.
Like, like, what's on the radar? Are things going well, not going well, or are they going really poorly? Because that's when you have to intervene quickly. And if you can't act quickly because you don't know what's happening, then you're in hot water.
AJ: Don't know
Spencer H: if that answers your question.
Chris: Yeah. I mean, that's one area where, like, being vertically integrated is is nice because
Spencer H: Completely agree.
Chris: You know, when that work order comes in, you know, it goes straight to the asset manager as well as the property management company. And then, you know, it's pretty pretty easily triaged.
Spencer H: Totally agree. Yeah. I mean, generally, best case scenario, dialed in vertically integrated. That would that would be ideal.
AJ: Nice. Well, in case you were wondering, we are vertically integrated.
Spencer H: That is awesome.
AJ: Yeah. We we have the construction company that supports the property management company, the management company, and then, you know, syndication company. So Which
Spencer H: is really hard to stand up. So kudos to you guys.
Chris: Spencer, I'm I'm interested in your some family investing. I mean, you run Madison with your wife as well your dad. You know? I'm I'm I'm assuming he he taught you a few things and you'd consider him a mentor.
Spencer H: Oh, man. Yeah. In terms of the gosh. These are all the things that you don't really realize you learn until later. Right?
Because we most of us learn from role modeling and then eventually emulate those things in how we talk and how we think and think how how we question life, all those things. So I I used to, as an example, give my dad such a hard time. Like, dad, why the hell do you wake up at 4AM? And I was always so confused why he did that. And there I was like in my w two career, needing to find time to go and learn this nerdy stuff that is multifamily large apartment real estate.
And no one else wants to talk about it at my day job. So I have to spend two hours waking up at 4AM to go study like a nerd at in the dark from four to 6AM to go do the job before the job over the course of, like, two and a half years. You know? And I'm like, well, where did I get that? That was from dad.
AJ: Well, how did you even
Chris: know it was possible?
Spencer H: Right. I mean, that's and I appreciate you asking the question. You know, I I look at that. And one other thing to call out, though, is, you know, that that there's a there's a a resilience and a an entrepreneurship resilience, I think, that came along with an experience that we kind of refer to as like a dark decade in our family. And I won't go too grim on this, but this is just this is what happened.
In, you know, when I was like an early teen, mid teen, my dad's business was like absolutely flying. This is like in the nineties. And, my younger brother who's a teenager at the time, he got terminal cancer. He passed away many years ago. But, my dad's business, you know, suffered because because of obvious reasons.
Right? And that was the family's sole income. Right? I mean, the the brokerage business means you're working or you're working on you're getting an income or you're not and there's no income. And seeing, his ability to persist through that, it really just stays with you.
Yeah. And I think it also humbles you in terms of what mean, I there's so many other learnings to unpack there. We don't have time for it, but I'll just say that, like, hey. What happens with a one income household and how do I avoid that? You know?
Like, the learnings both in terms of action as well as things to not do. I I'm I'm so grateful for him, and for and for all those lessons that he imparts both in his actions and role modeling and also, you know, the tough lessons about what not to do structure wise. How do we add more income streams to our family? All those all those important things that lead me back to, hey, this whole investing thing is a really good idea.
AJ: Yeah. That is a that is that is a great story that promotes, you know, gaining that passive income. So when hard times do come, like, there's a little bit of cushion too.
Spencer H: Absolutely.
AJ: Yeah. Thanks for being vulnerable and sharing that.
Spencer H: Yeah.
AJ: This is probably a good segue. I you had talked about some of your material learnings from the past three years because as we all know in this market, it has not been the smoothest of sailings. So I think, maybe a good time to jump into that.
Spencer H: Yeah. You know, we talked about sharpening the pencil and how important it is. Right? There's a few things that are kind of like the just duh moments, but they're they're probably for any folks that are, you know, amongst your listeners and they're like new to the space. I look at these as pivotally important now and I'm I go much harder on them than I used to in hindsight.
The first one being, okay, well debt. You have to talk about the debt. You know, invested with amazing sponsors. I still believe in them now, but some of those deals, they were on floating rate debt. That floating rate debt, I sure wish some of those deals were on fixed rate debt.
And so is there a time and place for a bridge loan? Is there a time and place for variable rate debt? Of course, there is. Absolutely, there still is. But I'm much more keen to to look at deals with fixed rate debt these days.
And so I think that that's gotta be one of the overarching big ones. The we really hit on kind of the core of the other ones though. I I would I would say already, which is like the track record isn't enough. You know, like the track record at a high level isn't enough. Like you really have to appeal back what's underneath the hood.
Like how is that track record achieved and how are they gonna apply that on the next deal that they see? And last but not least, man, I definitely wish I had stayed, like, purely within at least in terms of private investing. I know I have a lot of friends and brethren in the tech space and they like their angel investing in tech companies. This isn't really about that because that's its own category. You can get a multiple of 25, 30 x plus one out of a 100 deals.
Awesome. More power to you. That that's its own thing, man. There's other niche opportunities outside of real estate in private placements, and I've invested in a couple of them in the past few years, and I've lost a lot of money from that. And so I'm sticking with real estate.
I'm sticking with real estate because it has an address. Unfortunately, there are some people who do, you know, sus space, as my kid would say, sus behavior. Right? You know, sketchy behavior and, like, you you don't wanna encounter bad actors in the space. And just in terms of due diligence in real estate, there's some beautiful things about due diligence that you can peel back the hood and just see more concretely when you're doing that due diligence.
So those are really be the key themes, guys. It's like, number one, make sure that debt in the capital stack is solved and aligned with the right plan. Number two would be gotta go and look underneath the hood for due diligence beyond the track record. And then number three is stick to what you know. You know, just just just stick to what you know and what I know is a lot of this real estate stuff.
You know, like multifamily, those primary asset class we focused on. Self storage has become, secondary when we focus on. But when I strayed away from that, I got hurt. And I I would like to to lean into that.
AJ: Do you mind giving a couple examples of some of the shiny objects that you looked into or invested in?
Spencer H: Yeah. I mean, one of them was like like crypto. Like like, I mean, crypto in general, I don't condemn. Like, I I buy Bitcoin and and Ethereum and everything, but I want it as like a crypto mining thing ended up just in some fraud. You know?
Mhmm. So so it'd be that and just other niche business models, you know, within the space, but I don't wanna I don't wanna overshare.
AJ: Just out of curiosity, I I keep seeing that there's a couple of companies that I'm on their list for, and I'm just curious if you've looked at them or have any opinions on them. But, one is like the oil gas sector.
Chris: Oh, the scrubbers. The oil and then
AJ: And then the the other one is land banking. So there's a company that will buy up tracks of land and then do the entitlement to and then sell it to, like, Taylor Morrison or sell it to someone else. And they're usually pretty quick turnarounds, but they've And I haven't researched into the gas thing a lot, but what I do hear is that the tax benefits on them is just substantially higher than normal real estate. And I was just curious if, like, with those other, you know, investments, it was was there a draw for you to them like that? Or was it just the promise of a higher return or, you know, like, what what kinda drew you to these other other things?
Spencer H: Yeah. Well, that that's a great question, AJ. The characteristics are the same ones that you and I appreciate about real estate in the first place. Right? I mean, I want cash flow, great return, ideally some depreciation benefits.
I mean, that's the big, you know, triad. Yeah. You know, for oil and gas, I have circled that for years. I I've looked at multiple sponsors. I've talked to multiple sponsors.
I've looked at multiple investment summaries, many I I've seen okay. The the big reasons why, as it to your point, that people tend to be attracted and happy with their investments, at least on this front, is that wonderful looking k one, you know, where they have like really good depreciation losses on it. More importantly, the reason I was circling it so long and I haven't pulled the trigger on it yet, unless you're happy to share why, but is that you can actually get active losses. At least as they say. And this is my this is my moment to give my I am not a CPA nor a tax professional.
Take none of this as tax advisory, yada yada.
AJ: Neither are we.
Spencer H: So Yeah. Yeah. None of us are tax professionals. But to go as a sponsor to have an offering of there's so many different business plans within the oil and gas space. Right?
The the different versions and flavors of business plans that they they run with. But across them, you'll find regularly these structures that say, oh, an LP can be structured as a GP and therefore get active tax losses to offset their w two of active tax burden. Well, to a medical professional making $800,000 a year, that sounds very attractive to it, you know. So so where where I get where I hesitate is that I had yet to talk to per and this is just me personally. This has nothing to do, I'm not condemning the space.
I'm not condemning the sponsors that work in that space, disclaimer provided. I just haven't personally talked to a CPA that condones that structure. So that's all that I know personally, which is why I haven't pulled the trigger on getting into one of them. So but, you know, I I I think that it's a hey, I I I don't wanna comment. I'm not an expert on the oil industry.
I'll just say that it got a lot more interesting in the last week. So, you know, when when The US decided to go into Venezuela. So I don't know what that all means and ties into, so I'm probably not gonna be diving into oil and gas anytime real soon.
AJ: Yeah. Un uncertainty doesn't provide, you know, high risk or not high risk, but
Chris: high Well, low volatility. Yeah.
Spencer H: Right. Yeah.
Chris: Back to, I guess, evaluating sponsors or essentially just lessons learned, I'm interested to hear in how you evaluate, you talked about debt, but how do you evaluate the capital stack when you're looking at a single asset deal?
Spencer H: You know, I I think one of the things that I put a premium on now is really getting a sense of like the who, not just the who, like who's involved, who's the lender, Like understanding who's the lender, is there preferred equity in the capital stack, like like a preferred equity lender in the capital stack, other layers, you know. Those are things that I put a very big focus on now. And just because I've been in deals where there's preferred equity and you find out after the fact that there's like certain things that that that lender can do that that puts like your capital in jeopardy. And and then you may not even realize that at first. Right?
And so that that's gotta be the kind of the big headline callouts on on how I think about the capital stack is just making sure that, well, first and foremost, also that the amount of leverage is reasonable relative to that business plan. You know, they're not taking on more debt than they can actually handle, that there's some cushion in there to be able to cover the debt obligations, the DSCR, the debt service coverage ratio, all that stuff. And that there's no mystery lenders that can pop out of the woodwork and start and suddenly say, you have to sell this asset even though you're gonna take a massive loss on it and wipe out everyone else's capital. Like that kind of stuff you could spot ahead of time as long as you're just asking the right questions and like, you know, understanding who the lenders are that that are involved. So I'd say that that's gotta be some of the big ones.
Chris: Yeah. We we learned that lesson the hard way last year, sadly.
Spencer H: Oh, I'm sorry to hear it. There's a lot of that going around.
Chris: It's you know, about a year and a half ago, we were at a conference, and the theme of the conference was rescue debt, that it was people were raising rescue debt funds.
Spencer H: Yes.
Chris: I guess.
Spencer H: I heard about this.
Chris: For the for for deals that had been invested in, you know, that were gonna need to be rescued. And so yeah.
Spencer H: Yeah. I mean, there's a lot of that going around. Unfortunately, I hate to say, you're you're not alone on that one, but I'm sorry to hear about it.
Chris: Well, I think we should probably wrap this up. We've got four questions for you.
AJ: Spencer, you got time for four questions real quick? Alright. I'll start us off with the first one. What's one piece of advice you would give to your 25 year old self?
Spencer H: Treat every interaction as a relationship, not a transaction. We all tend to be very focused on ourselves in our twenties, and I I was very much included in that. And, you know, I think every person you work with in a company or, you know, you happen to partner with or whatever, man, you just meet them because you're both parents of kids in the same class. Like, these are all human beings and it's just the world is way smaller than you tend to realize until you get there later on. And then and then and then you're like, wow.
I'm really glad that I got to know that person because of this new opportunity or whatever else happens.
Chris: Wow. What was your first entrepreneurial endeavor?
Spencer H: Gosh. I I don't know if it counts as playing in a band, but maybe it does because it's if you make a dollar, they say you're a professional. Right? Yeah. I played played in a, you know, a few punk rock and metal bands.
And so that probably would be it. You know? But we I don't think playing dive bars up and down Capitola in Santa Cruz and California counts as necessarily a big entrepreneurial endeavor, but we made some money.
Chris: So That's weird getting an experience. Yeah.
AJ: You get your experience. You get a little taste of the the the pie.
Spencer H: And you're like, this is the lifestyle I want. Yeah. But
AJ: Yeah. Usually, it's like, man, that was really hard for that couple $100.
Spencer H: Yeah. Exact exactly.
AJ: Next question is, how has your formal and informal training shaped your journey?
Spencer H: You know, in the corporate career, two of the most powerful mentors in my life talked me into going down a leadership path when I really had no interest in doing it. And, this is in my twenties. You know, I ended up going from a kid who didn't find business that interesting at all, frankly. Part of that whole playing in a band of me punk rock thing, to then like leading teams of like 200 people for Fortune 500 companies, you know. And I was like, how did I get here?
And I'm not qualified for this, you know. But but flash forward years and you're like, it it those those lessons and principles are just instilled in you, forever. And, you know, that informs how I parent, how I'm a dad, and how I'm a hopefully show up as a good husband, and and, in lead medicine investing today. And so I I look at that like, you never really realize where it's gonna take you when, you know, the the both formal and informal. Like, they've been through tons of leadership trainings in the w two environment.
And and it was the hardcore, hard nose, very direct feedback that you get from mentors. I tend to be pretty dense and slow to learn. And the best bosses have been the ones that can they get very, very, very candid with me, and I'm deeply grateful for grateful for those people.
Chris: Yeah. Wow. Alright. Our final question. What was your biggest mistake, and what did you learn?
You
Spencer H: know, the god, this is a platitude, but I have to put it out there. Trust but verify. You know? Trust but verify. And I think that means, like, I we talked so much about vetting today and, like, you know, doing your due diligence.
And I'm inherently an optimist. I I I I I try to see the the positive outcomes, and I think I have to hedge against that because someone with the right intentions, at the beginning, especially as we're talking about real estate deals, five year hold periods, seven year hold periods, that's a long time, man. People change. People change under pressure. So trust but verify means trust someone's intentions, you know, when they say that they're gonna go do it the best they can, but verify that they actually can deliver on it.
AJ: That is solid advice.
Spencer H: Easier said than done. But Yeah. Yeah.
AJ: Well, Spencer, it's been a pleasure chatting with you. Thank you for, you know, opening up your book on how to vet sponsors and your experience in investing. We appreciate it. You know, it's been a pleasure. Thank you.
If our listeners, wanna get ahold of you and, you know, pick your brain a little bit more, what's what's maybe the best channel to, get ahold of you? And if there's anything else you wanna plug?
Spencer H: Yeah. Well, thank you to you guys. I appreciate us nerding out in the fun way for all these topics. Yeah. So they can find us at madisoninvesting.com.
And, yeah, they can reach out and we can sound board some ideas about investing and all this other stuff.
AJ: Awesome. Well, thanks again for being on the show, and, yeah, looking forward to chatting with you more.
Spencer H: Yeah. Thank you, guys. Really appreciate it.
Chris: Cheers, Matt, sir.
AJ: Thank you for listening to this episode of the Real Estate Professionals Investing Podcast on WIN, your community of investing knowledge for growth. We hope that this episode has increased your knowledge and added value to your path to freedom. If you would, please take a second to rate us so that
Chris: we can get more great investors
AJ: to interview. If you or someone that you know wants to be on, please visit westsideinvestors.com and fill out our form to be on the show. Thank you again, and enjoy your day.




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