The Importance of Goal Setting as a Passive Investor

Today’s guest is Spencer Hilligoss.

 

Spencer Hilligoss is a passive investor who deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, Spencer retired from a 13-year tech career to fully focus on Madison Investing, his passive investing club.

 

Show summary:

In this podcast episode, Spencer shares his personal journey from working in technology companies to retiring in 2019 to focus on his passive investing club. He emphasizes the need for clarity and vigilance in investing, advising investors to thoroughly vet teams and operators before investing. Spencer also provides advice on how to communicate with and motivate investors during challenging times, using two investor profiles as examples.

 

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Intro (00:00:00)

Spencer's background and retirement (00:01:26)

Clarity and vigilance in passive investing (00:04:25)

Twists and Turns in Investing Journey (00:14:05)

Positioning for the Next 12 to 24 Months (00:16:10)

Investing at the Wrong Time (00:19:19)

Motivating Investors to Invest (00:20:06)

Understanding Investor's Circumstances (00:20:41)

Educating Towards Future State (00:21:16)

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Connect with Spencer: 

Linkedin: https://www.linkedin.com/in/shilligoss/

 

Web: www.madisoninvesting.com

 

Connect with Sam:

I love helping others place money outside of traditional investments that both diversify a strategy and provide solid predictable returns.  

 

Facebook: https://www.facebook.com/HowtoscaleCRE/

LinkedIn: https://www.linkedin.com/in/samwilsonhowtoscalecre/

Email me → [email protected]

 

SUBSCRIBE and LEAVE A RATING. Listen to How To Scale Commercial Real Estate Investing with Sam Wilson

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Spotify: https://open.spotify.com/show/4m0NWYzSvznEIjRBFtCgEL?si=e10d8e039b99475f

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Want to read the full show notes of the episode? Check it out below:

Spencer Hilligoss (00:00:00) - The goal setting process, like if there were to be. What is the most active part of being a passive investor? Because there are active parts. Right? And this is the misnomer. I think it is sitting down and just gut checking with the financials. What is your true north? Or I'll take out the platitude like what is your financial target you're aiming for? Just like if you're inside of a business, if you're going to use to work in the corporate world, anyone who's in a W2 world, if you manage a profit and loss, if you manage a financial plan, you got to go and sit there and say, hey, last year we thought the target like a win would be that dollar amount. Well, this year is looking a little different. So let's revise like what are where is our bearing here.

 

Sam Wilson (00:00:44) - Welcome to the how to scale commercial real estate show. Whether you are an active or passive investor. We'll teach you how to scale your real estate investing business into something big.

 

Sam Wilson (00:00:58) - Spencer. Helios is a passive investor who has deployed seven figures of his own capital into passive investments in the past six years. In 2019, he retired from a 13 year tech career to fully focus on Madison investing his passive investing club. If you don't know, Spencer also came back on the show. Gosh, what was that? Spencer episode 274 I think. So sometime early 2021. We've done about 600 episodes since the last time you were on the show, so it's a pleasure to have you back on the show today.

 

Spencer Hilligoss (00:01:26) - Yeah. Wow, that's a fast two years. Sam. Thank you for having me back on. Absolutely.

 

Sam Wilson (00:01:32) - The pleasure's mine, and it is a fast two years. Spencer, before we get into the heart of the show, though, there are three questions I ask every guest who comes on the show. You have answered these previously, but we're going to have you answer them again in 90s or less. Can you tell me where did you start? Where are you now and how did you get there?

 

Spencer Hilligoss (00:01:48) - Oh yeah man, there's still fun questions.

 

Spencer Hilligoss (00:01:50) - Now I'm probably going to get a different lens on it though, as always, as life evolves. So where I am now actually, let's go back. I started growing up as a punk rock and metal kid playing in bands. My dad was a real estate broker for 30 years. I was working for him as a kid, which is why I ran screaming into technology companies. I live in Silicon Valley in the Bay area, California. I have, you know, grown up for 13 years professionally building and leading large operations and sales groups for fintech companies, financial tech companies. As you mentioned, Sam, I retired in 2019, five months before Covid, and that was not part of the plan, but I would say grateful now more than ever to be leading Madison Investing, which is our passive investing club, as you mentioned up front, where we help other folks walk the same path that we have. You know, I know that right before we hit record, I was sharing a quick story about highlight of the year so far.

 

Spencer Hilligoss (00:02:45) - We just got back from spending six weeks in Portugal as a whole family, that type of thing, that type of lifestyle decoupling from a geography, taking our kids who are six and nine and Jennifer and I are both living and working abroad with that flexibility. That's what's enabled by passive investing done right. And of course, it's not always like turnkey. Across the the journey. There's a lot of twists and turns. You got to pull out your figurative machete and hack through the the forest, as it were, and find clarity along the way. But hopefully I didn't exceed my 90s on that one.

 

Sam Wilson (00:03:17) - No, I think shoot, if you weren't, if you were, if you were over 90s, it was worth listening to. So I appreciate you giving us that. That recap yet again and again. If you didn't hear Spencer's first show, go back and check that one out, because I know we're going to cover some very different things. Maybe then what we covered there on that show. You know, I think one of the things and I'm not going to hopefully offend you here by saying this, but I feel like everyone has these grandiose ideas of what passive investing is.

 

Sam Wilson (00:03:44) - So they're like, oh, man, you know, we're going to be a passive investor and we're going to just cash checks all day long, and it's going to be amazing. But I think the experience is wildly different. I certainly know it has been for me, as I look at all the different passive investments I have, I go, okay, you know, there's some there doing well, some that are doing but not doing well, and then there's some that are performing very poorly. And I look at that and I go, gosh, that's that's it's kind of painful in some respects to look across all of them go, not everything's doing great. What would you say a current investors outlook and kind of mood should be about passive investing right now, because it doesn't always necessarily translate into six weeks in Portugal.

 

Spencer Hilligoss (00:04:25) - Oh my gosh, what a killer question to open with and for people listening. Sam didn't prep me for that question ahead of time. That's just a hell of a good question. Clarity and vigilance.

 

Spencer Hilligoss (00:04:36) - You know, I think clarity, first and foremost, it comes down to goals. And everyone out there hopefully is starting from that point. As a quick refresher, Sam, clarity to me means sitting down 2016. I'm working full time, deep into my career and climbing that ladder, making great W-2 income. Jennifer Morimoto, who is my my spouse, my wife, and my co-founder and, you know, co-pilot in life, you know, mother of our kids across the board. We work together in life and work. And we sat down and took a whole weekend to literally sit down and say while working full time, both of us in separate careers, what is the dollar amount per month that we could that we need to hit? Full passive. To cover our needs. And that was a scary exercise, man. That was a scary exercise. And it's something that I think I don't go into lightly, because that weekend had tears that we can had reconciliation and had laughter, and we had to get a sitter to get the kids out of the house just to do it right.

 

Spencer Hilligoss (00:05:37) - But that's where it started. We set that goal with a 15 year time horizon to remove all excuses. And so by clarity, what I mean is it sounds so clean and simple to say, I'm going to hit 8000 bucks in passive income, which I believe at that time was our monthly income, passive income target. And, you know, I'll qualify it by saying everyone has different expectations in life. Like, we don't want to we don't I don't need a jet. I'm a pretty simple dude. Like I got some guitars. I like plucking a guitar, but I don't need a boat and no judgments on those who want more. But that was our goal back then, and we hit that goal in the last about year and a half, two years ago, we hit that goal in full passive. And we're we're so proud of hitting that. That was hard. But we said 15 years on, the original goal came back shortly after that exercise in 2016 and said, well, that's just too long.

 

Spencer Hilligoss (00:06:29) - You know, you and I were chatting about our kids right before we hit record today, Sam. And I'll say that like, we wanted to catch some of the magic years, as it were, spending time with our boys while they were still pretty young, and being able to have that type of lifestyle where we could spend more time. And that is what got that clarity for me. So thanks for listening to that context. I just think it's so key for people to sit there instead of saying, man, look at that great looking Facebook paid ad that presents this two x equity multiple, right on a killer looking deal, a beautiful marketing deck. And you're like, that's my ticket to financial freedom. Be like, slow down, get clear. Get clear on why you're looking at this thing. And then don't worry about asset class yet. Come back to it later. Those are the lessons I wish I could impart on myself earlier on. One other thing I'll say is like 2023 for sure has presented some challenges, right? And you hit it earlier.

 

Spencer Hilligoss (00:07:19) - I'd say that things like understanding the basics of what is the purpose of this one investment, what's the goal for the money? Is it a growth play? If a person is working, like talk to one of our investors in our club who's actively investing with us, has for years, and he says, well, in 5 to 7 years I want to get X dollar amount. By fully passive, you know, 5 or 7 years out. And that's a very thoughtful, responsible goal for that investor. That's a cash flow investor who is making killer W-2 income at a day job, doesn't need it now, wants to have it later so they can still potentially afford to go and invest for growth. They don't need the cash flow now, but if that same investor puts a bunch of money, puts 100 K into a deal, and they have a pot distribution right now. And they're going to get great growth on the back end of that thing. But they don't have a distribution coming in now for a monthly income.

 

Spencer Hilligoss (00:08:13) - That's a mismatch. So I'll take a pause there. But just wanted to kind of cover at least the vigilance on the clarity.

 

Sam Wilson (00:08:18) - No I think that's great. I think that's really, really great. You touched on the term goal for the money, which I think is is a it's a powerful. It's a powerful idea because even though we have financial planners and we have people that lay out again all the, hey, you know, this is what you're going to have if you invest. And of course, we've all been through that drill with with our stockbrokers and everybody else where they show, you know, projected where it's going and what it's going to do. I think a lot of times we missed that same exercise. At least I have personally in my own and passive investments around the country in commercial real estate because it's like, oh, that's cool. Like you said, that's a cool deal, I like that. Why not? Let's throw 50 grand or 100 grand at it and see where it goes.

 

Sam Wilson (00:08:59) - Like, this is going to be fun. But then you look at it and you're like, wait, did that actually line up with what I wanted to do in 5 or 7 years? Because that requires discipline and time. It requires those weekends that you're talking about going, okay, you know, getting a spreadsheet of everything, or maybe it's even more complex than that. But if everything where it's going, what you're expected, payouts are getting them. I mean, that's hard work. I've got a sheet like that. It's hard work. Comparing zero eight. We got a distribution this month. Did it line up with what was pro forma? Which of these are doing what they say they're going to do. And that's that's just it becomes its own kind of animal that. I don't know. Speak to us on that front if you can.

 

Spencer Hilligoss (00:09:37) - Oh, man, I love this topic. I would say you're nailing it. And by the way, I'm so guilty of the same thing. You know, you see a great looking deal.

 

Spencer Hilligoss (00:09:45) - Or maybe you just love the team, like, like, oh, I love that operator. They have such a tight operation. Their reporting is killer. Their financial reporting is transparent. They have experience. They've got repeatable process. They've got the exits, full cycle deals, all the works. Right. And I'm like, oh cool, let's drop money. And then I'm like, well, that wasn't so much of a cash flow play. I mean, it reminds me of the very first property we bought is a duplex sitting in 45 minutes from our house, where I'm sitting right now in Vallejo, California, and that thing costs 430 grand. And that's a California property for you. We bought it years ago, cost us six figures. It's down payment and a cash flow is $200 a month. That is not a cash flow win by any measure. That's a quick way to use the player capital, right? But I bring that up as one example of like where we started to where we are now.

 

Spencer Hilligoss (00:10:35) - And I would say now actually we're going through a refresh of this very exercise. And it's related, I think, to what you brought up a moment ago, Sam, you know, the goal setting process, like if there were to be what is the most active part of being a passive investor? Because there are active parts, right? And this is the misnomer. I think it is sitting down and just gut checking with the financials. What is your true north? Or I'll take out the platitude like what is your financial target you're aiming for? Just like if you're inside of a business, if you're what I used to work in the corporate world, anyone who's in a W2 world, if you manage a profit and loss, if you manage a financial plan, you got to go and sit there and say, hey, last year we thought the target like a win would be that dollar amount. Well, this year is looking a little different. So let's revise like what are where is our bearing here.

 

Spencer Hilligoss (00:11:28) - And so we're going through that now to say well you got to track it in a spreadsheet. You've got to sit down and say what's the monthly income expected from this. Are we up? Are we down. How much do we need? Are we off track? Do we need to reserve some capital because our family is going to face some some headwinds or maybe tailwinds. Maybe there's good news coming in. You know, just got some unexpected great news on, like, an exit from a deal that is like a mobile home park refinance that's coming in. And I was like, wow, that's the first, I think, capital event that's occurred in 2023 personally. So like that was that was quite unexpected, you know. So I'm like, woo, that's great to see. And we'll see a lot more of that hopefully between 20 and 24 but most likely 2025. So it's tracking and knowing where you're at on that figurative map and sitting down and saying, let's put some financial assumptions behind it, like, what are we going to get out of this deal? Exits, cash flow.

 

Spencer Hilligoss (00:12:18) - What does take work? It takes some work, you know.

 

Sam Wilson (00:12:22) - It does take work. And I think it takes work. And it also, like you said, figuring out, you know, what your true north is in this and then and then picking the right opportunities that kind of make up that matrix of deals that you should or should not be investing in. So I think that's just knowing just knowing what it is you're looking for. And again, not being guilty of following my footsteps and just going, oh that's cool. Like I love the sponsor. I love the deal. I mean, why shouldn't we do it? Like, because maybe it doesn't fit the plan. I was having a call with a with a. Friend slash business guy here in Memphis yesterday. And he goes, he goes, Sam. He goes. My answer should be to, you know, he goes, it's no. Because for these two reasons he goes, but yet I just can't help but talk to you about it because this is really fascinating.

 

Sam Wilson (00:13:11) - So let's keep going. And I'm like, Bill, you know exactly what your answer should be. And I appreciated that. It was it was just a funny response. He's like, my answer should be no because I don't know anything about it and it doesn't fit my box, but I want to hear more like so anyway, we all.

 

Spencer Hilligoss (00:13:27) - Do it.

 

Sam Wilson (00:13:27) - We all do it, but we all do it. Yeah, we all do it. Not falling into that trap. So that's really cool. We've talked a little bit about defining temperament in our in our investments, being a tempered investor if you will, finding out goals for the money currently. Tell me tell me a little bit about this. Like what you said that there's two things. One, you said you've experienced some twists and turns in your investing journey. I think you said since 2019. So maybe if you can give us a couple examples of what those twists and turns are, and then tell us how you guys are positioning yourselves to really take advantage of the next 12 to 24 months.

 

Spencer Hilligoss (00:14:05) - Yeah. Happy to. So. Twists and turns first. Abbreviated version. I can define this in three quick phases. This is not how it felt. Real time. Of course. Life has crazy chapters. You don't know where you're at on the map sometimes until you come out the other side of it, right? So phase one still working full time. This is back in about 2016. We bought that rental that pricey for 30 K rental. I just told you about California and we're like, wow, we're going to run out of money real quick this way. Not in line with our cash flow goals. We then got more comfortable to really took our time and looked at more rentals. Still didn't hadn't quite moved on beyond that rental phase. And rentals are fine. They're a great wealth builder, but. They are semi passive at best. Right and I will happy to debate anyone on that topic. Anyone who's owned rentals can attest to that, property manager or not. They're semi passive. So we got up to five long distance rentals and they were out in Kansas City, Kansas City, Missouri and 60 K average purchase price 250 bucks a month.

 

Spencer Hilligoss (00:15:08) - Average cash flow. That's a heck of a lot better economics than the first one. Those were maybe, at best, C-minus neighborhood. Um, you don't really learn what that means till you do it.

 

Sam Wilson (00:15:21) - Right?

 

Spencer Hilligoss (00:15:22) - And, you know, you get you get it. So we learned that way in terms of overhead, you know. That was more work than we expected it to be. Even with property managers, the economics got a little bit kicked every year because the tenants would beat up the place a little bit, and then we had turnover costs, etcetera. So we sold those properties, and then eventually we started investing as passive investors purely as LPs and some multifamily deals. And we're talking in Alabama and in Texas and a few other great markets, eventually multifamily self-storage. And those twists and turns initially, I would say were super important. You know, like a little expensive. You pay tuition with experience and scars. You also pay it with physical capital. And I would just say that those those were not, in hindsight, ideal if you're trying to maximize return, but they were necessary for us to get to where we are now.

 

Spencer Hilligoss (00:16:10) - And so I look at those also, once we started investing as LPs, got some killer exits from those. This is around the 2018, 20, 2019. And then we're like, well. There's so many colleagues and so many folks in my network that were saying, Spencer, like, we don't want to fly out to these properties like, you're, you know, this stuff. They're saying this to me like, you know, this stuff, you're flying out of these assets, you're walking them. You want you know, how to underwrite them. All this stuff. And I'd work so hard to get there to do that. Why don't you? What? You help us, you know? And so then we started medicine investing around that time. And it's just the club dynamic of being an educator and a resource for folks to see who who are these teams we invest in. But that doesn't necessarily mean it's always clear. It doesn't mean it's always easy. You know, like like taking the time to get to know partners and operators is it is art and science.

 

Spencer Hilligoss (00:17:05) - You know, it's, you know, vetting teams and humans is always going to be that way. And so I would say those were some of the whiz bang version of like the twists and turns along the way that brought us to where we are now. Um, I'd say that looking forward to your second question, though, right now is a unique time. You know, I think before this journey over the past seven years, you know, coming out of a tech career, Sam, like, I wouldn't have known how to take in the feedback and the mentorship that we hear, the wisdom that we hear when it comes to when's a great time to invest? Like when do the wealthy people, the wealthiest of the wealthy, the Warren Buffett's like, when do they make the biggest returns? When do they maximize their wealth building? And I wouldn't have understood. Like, you got to go out there and take informed risks during challenging volatility times, during economic headwind times. And that is why right now we're walking into a killer buying opportunity.

 

Spencer Hilligoss (00:18:02) - We're walking into a killer investing landscape. And it's it's the tough part for every investor is to look through the noise. There's a ton of very real noise occurring right now in the headlines, of course, globally and nationally. But I would say take what you need from the news, but then look past. It has best you can, you know. And so we see opportunities to buy and invest at the asset classes that we love. Multifamily large apartment communities largely in the Sunbelt. With some of the Rockies still love self-storage. We've been focusing on self-storage now since 2019 as a sister asset class, along with multifamily and a couple of other niche non-real estate asset classes. But I would say that that's really what it's about is just being vigilant about not pouncing on a deal is because it looks like it's great from a team that we know you got to go do it deeper. And clearly I have to say this as well. One last thing is just like the interest rate has to be the debt, the loan, the loan structure has to make sense in the current climate.

 

Spencer Hilligoss (00:19:04) - It has to be either in a suitable loan. You know, there's a lot of that going on on the few deals there are, or it has to be some kind of unique situation where the seller is distressed and you're getting a very significant discount, but tough to find those.

 

Sam Wilson (00:19:19) - It really is. But those are those are things. And I like your, your you seem to be a more patient investor maybe than what some of the, some of the, you know, fury that's been out there in the last couple of years, you seem to take more time in what it is that you're investing in. And I think you're right here in the next couple of years, we're going to see we're going to see some great opportunities come down the pipe. But I guess here's a question for you. Most investors, the book, Howard Marks wrote the book, Mastering the Market Cycle. And in that he basically says that historically, investors invest at the completely wrong time. Like if you just take the data and you overlay it with the economic profile, he goes, they're always investing at the top and selling at the bottom.

 

Sam Wilson (00:20:06) - He goes just right the way they do it. So how do you in the times of how do you I mean, I'll get to my question, but how do you communicate to your investors and then motivate them to invest at the times when it's like when everybody else is out yelling, run! You know, there's blood on the street, everybody's going to die and you're going to go, hey, man, you know, actually, right now is the perfect time to buy this distressed asset. You communicate that in such a way that it then compels your investors to invest.

 

Spencer Hilligoss (00:20:41) - Yeah. Gosh, that's a fun topic, man. I love the reference for the Marx book. I think understanding the posture as like as a passive investor myself, you know, as a passive investor yourself as well, it comes down to understanding fundamentally that like motivation to invest in motivation to act is is probably the incorrect way to look at it. It's really like, does a person understand squarely where they are? If you're trying to educate like they understand, this is probably going to lead back to a goals comment.

 

Spencer Hilligoss (00:21:16) - But I would say that it starts with just holding up the figurative mirror and saying, here's where I'm at. You know, here's an investor's circumstances. And if they are comfortable where they are, you're really not going be able to prompt action and you don't want to. I'm not interested in trying to compel someone to go and invest in something that is not fit for their portfolio or fit for their their goals. I think really what it comes down to is helping them understand the future state, understanding the future state. What I mean by that is where is the life they want to be, right? Like in three years, five years, seven years, whatever that time horizon could be. And if that means, you know, let's take two profiles. I'll just keep them anonymous and kind of abstracted here. But like profile one most common one, I would say a fellow investors that we work and invest alongside with W-2 employees, at least one significant W-2 income coming into the household likely to if they're in California.

 

Spencer Hilligoss (00:22:10) - Absolutely to because it's just too expensive here to have one usually. So they're sitting there going, I don't necessarily need to quit my job right now. That profile of dual income with kids, California or West Coast pricing market, they're thinking in maybe five, seven, maybe ten years. Then we want to have some optionality, because perhaps they're aging out of the tech career because ageism is a thing, and eventually they want to have some kind of safety net. So they have to think about these goals. And so educating toward that future state absolutely is the most important thing. And then connecting the dots backwards from that, like reverse engineering where do they want to be. Similarly, it's going to sound familiar, probably to where Jennifer and I were at, you know, years ago. It's like where we where were we when we started holding up that figurative mirror? Looking across, auditing our income sources, auditing our wealth, picture all that stuff, and then setting a real clear, crystal clear vision of like, well, where do we want to be? You know, what kind of lifestyle do we want to have? What kind of options do we want to have? That all applies for people who are working, and they have to work currently for their income profile.

 

Spencer Hilligoss (00:23:17) - Two high net worth folks, folks who, you know, maybe they exited a business that they built. Maybe they own a company actively, but they're taking more of a backseat while the next generation takes it over. You know, all that profile of so many different high net worth folks out there. But I would say that is more of a discussion of hedging downside risk in a discussion of capital preservation and understanding, like, yeah, I absolutely agree. It's a unique time when you're looking over there at the treasuries and you're saying, wow, that looks like a super safe 5%. Well, what percentage of their portfolio are they trying to allocate toward that? And also, is it really 5% that they want or are they looking at that 5% a little bit too myopically. Are they are they overanalyzing and just using that as their, their, their Uber excuse for analysis paralysis because they just don't want to go and do the mental work across the market right now to think, oh, there are excellent deals that can produce double, triple plus whatever you're getting on a treasury, you know.

 

Spencer Hilligoss (00:24:17) - So not getting probably getting a little too nerdy here probably for that one Sam. But that's a fun question.

 

Sam Wilson (00:24:22) - That's awesome Spencer, thank you for taking the time to break. Break that down. And a like I like the the the the phrase you said educating to that future state. And again I probably misused the words not motivate or compel. But it's one of those things. How do you get people off the fence. Yeah.

 

Sam Wilson (00:24:37) - Yeah yeah.

 

Sam Wilson (00:24:38) - And it's and it's and that's because again, we don't want people investing. And I've told people that I've told people before I said, no, this just isn't for you like this. This deal is not for you. So please don't invest. Yeah. You can just sense it. But, you know, I do think it is important, though, to see people when they're stuck in that analysis paralysis going, oh my gosh. Like I'm just going to sit here because everything looks so scary. And I think you've you've made some really valid points there on that that I won't rehash and kill it because you did.

 

Sam Wilson (00:25:04) - You did a great job really explaining that. So thank you again for taking the time here to come back on the show today. It's been an absolute pleasure to have you back on. If our listeners want to get in touch with you and learn more about you, what is the best way to do that?

 

Spencer Hilligoss (00:25:17) - Yeah. No thank you, Sam, this has been awesome to reconnect. So Madison Investing.com, that's our website and folks can find some educational content there. We put up there monthly. They can also set up time to chat with me. Happy to be a sounding board on their passive investing strategy.

 

Sam Wilson (00:25:31) - Fantastic. Madison Investing.com. We'll put that there in the show, notes. Spencer. Thank you again for taking the time to come on the show today.

 

Sam Wilson (00:25:38) - I do appreciate it.

 

Spencer Hilligoss (00:25:39) - Yeah. Thank you Sam, really great to see you.

 

Sam Wilson (00:25:41) - Hey, thanks for listening to the How to Scale Commercial Real Estate podcast. If you can do me a.

 

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