August 28, 2021

JF2552: Top 3 Investor Underwriting Tips with Denis Shapiro

While investing in traditional assets, Denis Shapiro failed to create meaningful income. Instead, he merged traditional investments with real estate investments to cultivate the portfolio he has today. Denis lays out the research he does before investing in any deal, circumstances where a preferred return may not be a priority, and some major negatives of ATM funds.

Denis Shapiro Real Estate Background:


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Joe Fairless: Best Ever listeners, how are you doing? Welcome to the Best Real Estate Investing Advice Ever Show. I’m Joe Fairless, this is the world’s longest-running daily real estate investing podcast, where we only talk about the best advice ever, we don’t get into any of the fluffy stuff. With us today, Denis Shapiro.

How are you doing, Denis?

Denis Shapiro: I’m doing great. Thank you so much for having me, Joe.

Joe Fairless: Well, it’s my pleasure and looking forward to our conversation, because you bring a variety of different investing experience. So here’s Denis’s background—he’s a full-time fund manager, he has nine years of real estate investing experience. His portfolio consists of rentals, traditional equity positions, private lending, ATM funds, note funds, and he’s in 10 residential syndications as a limited partner. He’s based in Freehold, New Jersey. With that being said, Denis, do you want to give the Best Ever listeners a little bit more about your background and your current focus?

Denis Shapiro: Sure. So I started investing in traditional assets about 20 years ago, after my brother gave me a copy of Rich Dad Poor Dad. So I was in high school at the time, so I had no one to talk to about this. Went the whole traditional route, went to a business school, intended to be a traditional stock portfolio manager. And then I kind of got smacked right in the middle of the global financial crisis, where I couldn’t find employment. I ended up going for my MBA and then I got recruited for the government. And when I got my first paycheck, I realized that the government was not only my employer, they were also my business partner. So I started looking into legal ways of reducing my taxes, and that’s where I stumbled onto alternative investments and mainly real estate.

At first, I was really trying to keep the portfolio separate, where I was like, “Well, I have my traditional portfolio, I have my traditional stocks and bonds, and then I’ll have my alternative portfolio. I kept looking at it as two separate entities. And then what I kept realizing is on my traditional side, I kept failing to create meaningful income. I was an early subscriber to the FIRE Movement, and as I was approaching my retirement, I was like, “I really want my portfolio to both appreciate and create income.” And every single income strategy that I tried with traditional assets, it just didn’t work. I tried the bonds, and the utilities and the REITs and everything. And the same thing kept happening over and over again, I would have 2-3 years of good size yield, and then one small correction, and all of a sudden, all my yield was gone.

So what I realized was, I was looking at the portfolio and I was trying to make it into something that it wasn’t. So I had an epiphany moment where it’s like, “Okay, if I just take all my traditional assets and put into low-cost index fund, I’m going to be using 1% of my brainpower.”

Now I could focus in on the alternative side, where I’m creating a lot of income here and it’s so much less volatile because they’re all private securities. So when I realized this epiphany, where “Hey, I’ve got to stop looking at the traditional for income, but I have a perfect solution with the alternatives”, I kind of merged the two together and instead of looking at whether I should be doing traditional or alternative investments, I realized I should be doing them both, and they both complement each other more than investors like to admit.

Joe Fairless: Why are private securities less volatile?

Denis Shapiro: Just liquidity; it comes down to as simple as that. The best example is March 2020 – if you were a real estate investor in March 2020 and you owned publicly-traded REITs, because in quotation marks, that’s what’s a real estate investor in most circles, you were down 34% just like the rest of the market, because the market is basing it on future projections.

Now, my private portfolio of syndications and stuff – how many syndications traded hands at that time? There was such a disconnect between the buyers looking for a discount and the sellers saying, “Well, this isn’t so bad yet.” No one was meeting to actually trade. So what ended up happening is my private side wasn’t down anything. It wasn’t trading. Because of that, because it’s not as easy as clicking, going into your brokerage account and doing 1, 2, 3 clicks, it takes more time, there’s more parties involved… So the chances of you doing an emotional trade is much more limited when you have business partners, and everything that goes along with private securities.

Joe Fairless: Now, the downside to that is because it’s less liquid, if you need the money, you’re not going to be able to get it most likely at that time, it’s going to take a little while.

Denis Shapiro: Yep. And that’s actually one of the perfect synergies between having traditional and the alternatives, you’ll always get that liquidity from the traditional. So that’s why I’m not 100% here or there. My philosophy is more to keep a portion of your portfolio in traditional assets, mainly low-cost index funds, that are not going to require much brainpower, so you could take advantage of the low liquidity on the alternative investment side.

Joe Fairless: There’s something about being able to log into, say, Robinhood, for example, and see, “Oh, wow, my investments are going up by $3,000 today. I’m an all star, this is awesome.” There’s some psychological dopamine rush probably that you get by that versus the alternative investment, where not much is happening; you’re getting money, assuming it’s going well, but not much is happening. That’s just an observation I have, I guess it’s not a question. It’s just an observation. And feel free to riff off that if you’d like, or we can move on.

Denis Shapiro: No, I would agree to that. But I would also say, like a devil’s advocate is if you do get more familiar with commercial real estate, like yourself, if you get your monthly report and you see what your NOI number is, probably in the back of your mind, you’re already calculating what the value of that property is, right? So I think it comes with experience; definitely the newer investors to alternative investment space are not going to have any understanding what a monthly report is, and what the fact that you’re in the mid-90s occupancy versus low 90s or 80s, you’re probably not going to get all of that at once. But I would definitely say, with time and experience, you’ll definitely understand that your property is getting more value. But you’re right, you’re not going to be able to just define it, what that $3,000 bump is for that day, or whatever it is.

Joe Fairless: That’s a good point. Thanks for bringing an insight into my observation, so I appreciate that. Let’s talk about what you’ve invested in on the, as you call, the alternative side. And it’s funny, because I’m a real estate investor, when you originally said you got introduced to traditional assets 20 years ago, I was thinking real estate when you were talking about it. But you were talking about it from a stocks and bonds’ standpoint.

So with your portfolio on the, as you call it, alternative investments – and probably most people call it alternative investments – rentals, large traditional equity positions, private lending, ATM funds, note funds and an LP on residential syndications. What has not worked out based on that list that I just read?

Denis Shapiro: I think they’ve all served a purpose. Even some of my syndications definitely have not even been home runs, I would even be generous by calling them singles. They were definitely the ones that I did early on. But for the most part, they’re actually kind of unique. A lot of these are real estate-based. So whether or not you invest in a mobile home park or a self-storage, what you realize is once you start learning the language of real estate, this stuff really piggybacks off each other.

Now, I know alternative investments is a really broad term, and it really is almost any private security that’s not traded on the public market. But my core focus is definitely on real estate. Alternative investments require you to really gain a foothold of knowledge before you become proficient at it. Because you know as well as I do, the operators, they all have “conservative deals”, in quotation marks.

Joe Fairless: Right.

Denis Shapiro: And it’s all about that building curve where you could start actually taking the deal and saying, “Okay, let me see what assumptions the operator’s using. Let me see what the market is, let me see how they split up the market. Are they using the right comps?” All of that is a huge, huge learning curve.

So it isn’t one that sticks out. I would probably say my short-term rentals probably wasn’t what I expected, and my single-family rentals – I had a low-income housing story that is very typical for a low-income housing story. So they all have bits and pieces in my journey in terms of getting to this stage, but all of them have gotten easier as I got much more familiar and have a better understanding of them.

Break: [09:30] to [11:31]

Joe Fairless: Alright, let’s talk hypothetically about a new apartment syndication opportunity that you got emailed yesterday. And it’s from an operator who you are familiar with, because you’re on their email list. What do you look at in the email? And then what, if any, research do you do outside of the email to determine if you’re going to invest in that or not?

Denis Shapiro: Wow, this is a great question, Joe. At this point — it definitely has evolved to this point. So the first thing I know is I’m pretty familiar with my own portfolio. So I know there’s probably certain markets that I’m probably overexposed in. You know, as much as I do some primary markets, that’s where the majority of the deals are happening these days; Texas, Florida, the South-East handle.

So one thing I would look at right away, and this is where it tailors to your own individual needs, is “How much exposure do I have in that market?” Then the second part is – well, if I don’t have enough exposure in that market, how have the other deals been performing in that market? And then besides that, you also look at the operator and saying, “What is my experience with the operator?” Usually, if you’ve built out a network of other LP investors, someone has invested with that operator if you haven’t; if this is your first time, really on their investor list, and you haven’t done any deals. So if the market looks good, if it’s an operator that seems credible, then I’ll start actually reaching out to my actual network.

Now, at the same time, I’m also underwriting the deal myself. Not crazy — I’m not underwriting into the point that I’m submitting an offer on as a GP side would. But to the point where I’m looking at certain assumptions being used… What is the rent growth? Are they operating at least 50% operating expenses? What is the vintage of the property? How much cap-ex do they have? How many different levers are they going to have to push to get this business plan going?

Personally, the less levers, the safer the kind of deal is, because if they have to hit it out of the park on the renovation and repositioning the thing, and getting it right with a new property manager that they’ve never worked with. So if you start with all these different levers, then the deal probably looks a little bit more riskier than the operator would like you to believe. But if you go through all the levers, and “Hey, just a dog park might increase the rent by an extra 100 bucks, and these are the two comps that show it”, and $100 is all you need in the value outside to really make the deal work, now everything else – they negotiate a cable plan, or they do do higher-end renovations and everything else becomes like gravy, then the chances are that they’re going to overproject.

So those are the kinds of things that I look for – I look at the market, I look at the operator, I look at the business plan, I look at the assumptions being made on the deal.

Joe Fairless: So from someone who has a full-time W-2 job who is not in the financial industry, how could they approach doing something similar, but they don’t have your level of expertise in underwriting?

Denis Shapiro: One thing I would say is investing in private securities is not cheap. So one thing I strongly recommend is investing in education. I think it’s huge. Especially these days, you could put on LinkedIn, just put in the fact that you’re a real estate investor and you would get offered 15-minute calls left and right. Now, most of them will be spam, but at least you could start learning the language of real estate investing.

Now, once you have a decent grasp of the language, then you could start actually building out a network. Because you don’t want to try to build out a network and you don’t know what you’re talking about. You want to have a basic understanding of the language being used, and then you could start networking. And once you build out a certain amount of networking, a lot of times the due diligence could be done for you to a certain extent; like, did you ever invest with that operator?

Now, you might not get an unbiased answer for the first couple of months, but once you have a rapport with that fellow LP investor, they’ll probably tell you exactly what’s going on. And once you have that relationship, then you could feel a little bit better. Now you’re like, “Okay, well, that’s one checkmark off my checklist. Hey, now I know the language. Now I have a little bit of a network.”

And then the other thing that I can’t stress enough is, people who have a good W-2 job – it doesn’t take a long time to figure out some of the basics in underwriting. There’s so much great underwriting software that’s out there that comes with courses, that may take you maybe a week to learn—

Joe Fairless: Like what?

Denis Shapiro: I would probably put Michael Blank’s underwriting software… I kind of think that’s a standard, and he has a great walkthrough video series. It’s like 100 bucks. I think it’s extremely worth it. I know a lot of the syndicators use their own syndication software. But in terms of just the note rules, and to take a look at what assumptions are being used, I think Michael Blank’s is pretty good. And you’ll see a lot of his stuff copy and pasted into a lot of the offerings. So if you could get a better understanding of the software, I think those three are pretty powerful when you combine them.

So learning the language, getting a little bit of a network, and then learning the basics. I’m not talking about you should be the lead underwriter on the deal, but I’m just saying enough of the basics where you’re seeing what are the assumptions, and can you label them aggressive, or actually are they conservative?

Joe Fairless: One thing I didn’t hear you mention, so that leads me to believe it’s not top of your mind, because you didn’t mention it, is the deal structure, namely preferred return. How much do you look at that?

Denis Shapiro: That’s such an interesting point. And I would probably say, initially, I was much more tunnel-visioned into that. But what you start realizing, especially as an LP investor and as a fund manager, is the operators piggyback off each other. So you’ll start seeing one operator drops their preferred return, and all of a sudden, you start seeing a cascading effect of more operators dropping their preferred return. Or one operator does a fund, and then all of a sudden you start seeing the trickling effect, and more and more operators do the fund.

Same thing a year, a year and a half ago, it was that dual class preferred structure that went through the whole syndication world, where it’s the higher class A shares but with no equity kicker, and then the class B shares get a little bit of both, and 70/30.

So I definitely think the terms are more important if this is the first time dealing with the operator. But if you’ve done four deals with an operator and they’ve all gone really, really well and they’ve outperformed, are you going to choose a different operator that’s offering 2% projected returns higher? I’d probably say no.

The other thing I would look at is, what is the norm being offered. So if I have a bunch of class A operators giving me 13-14 percent IRRs. And then I will get a deal that has a 20% IRR on a similar class and a similar location, that’s more of a red flag to me tha. If A-grade operators are conservatively underwriting a deal at 13-14, and then I’m getting thrown a deal at 20 similar and I’ve never heard of that person – to me, that’s just more of an instant red flag than saying, “Oh, yeah, I want to do the higher returns.”

Joe Fairless: Would you invest in a deal with no preferred return?

Denis Shapiro: This is tricky. I think that’s more on the business plan. So I wouldn’t say it’s a complete no. Obviously, just the concept of preferred return is beneficial for an LP; a certain amount of the returns are protected before the profit is split. So it’s obviously a benefit for an LP. But on the flip side is, what is the deal? Is it a value-add where in two years you’re going to do a refi? Because the other thing that I think is extremely misleading, you’ll see in the industry; although there are 10% pref, but then in 12 months, there’s a projected refi of the whole thing. So then what is the pref going to do at that point? The pref disappears once there’s a capital return.

So I think as long as it’s not misleading, as long as you know what you’re getting yourself into, I wouldn’t say it’s a deal killer not to have a pref. And honestly, I think just that — I know from the certain operators that I follow, given the speed that they’re raising money these days, I wouldn’t be surprised in the next 12-24 months to see a shift away from pref.

Joe Fairless: Let’s switch gears a little bit, let’s talk about ATM funds. What’s your experience with ATM funds?

Denis Shapiro: A lot of the things with alternative investments is I’ll hear about an idea and I’ll kind of be intrigued, but it’s not like I’m going to be like, “Oh, I’m going to go write my checkout right now.” So ATM funds, I kind of put them in the same boat as life insurance policies. I liked idea when I heard it; I was like, “Well, that makes sense.” But I really have to get my head around this, because this isn’t your typical syndication where there’s a preferred return and then you get a split at the end. So it was very, very different, I’ll say.

The other thing that I came across is – I wrote this in my book on the ATM – is it has a high level of Ponzi schemes. So those are the big negatives. It’s a very different model. And if you invest with the wrong operator, you can lose at all.

Joe Fairless: Is that based on research, it has a high-level Ponzi schemes, or just anecdotally?

Denis Shapiro: I think it’s just the nature of the business, because it has so much cash.

Joe Fairless: But where did you identify that it has a high level? Is that just something you think or something that you’ve seen?

Denis Shapiro: There’s a list, and I could try to find the list… There’s certain asset classes that are identified by, I think, the SEC as higher likelihood of fraudulent operators. I could definitely try to find the list—

Joe Fairless: That’s all right.

Denis Shapiro: —and send it to you if want to put on the list. But it is actually on a list. In one case – this happened in New York only like 10 years ago – the operator said they have 4,000 ATM machines, and they literally had only 400.

Joe Fairless: They were just missing a zero…

Denis Shapiro: They were just missing a zero. The shame is who’s really the problem? Is that the operator or the asset class? The asset class make sense. The problem is the operators that sometimes get attracted to that asset class; there might not be the best intentions. And that’s why — this was one of those where I was like, “I really have to learn the due diligence of this.” And I really tried to network, and I luckily networked with someone who’s identified three Ponzi schemes in the space before in their own research, and gave me a blueprint of exactly the steps to take.

Joe Fairless: Wow.

Denis Shapiro: And I included that in the book. And that blueprint actually made me feel comfortable with saying, “Okay, let me actually try this out.” Because the business model is very different. If anybody’s — just quick, I don’t want to get into a tangent… The business model is very different, because basically, the value of an ATM machine depreciates so dramatically in seven years that you’re basically walking away with zero. But the cash flow during those seven years is so significant, where you’re still making a pretty decent return. But at the end of the day, you’re not actually expecting anything for those ATM machines at the seven-year mark.

Break: [22:29] to [25:32]

Joe Fairless: So right out of the gate, it better be a cash cow.

Denis Shapiro: Yeah. They contractually do it where, in four years, you kind of break even. With depreciation, it’s a little less. So it’s a very different model that you have to be comfortable with.

Joe Fairless: Mm-hmm. Yeah, it’s the opposite of real estate…

Denis Shapiro: Exactly.

Joe Fairless: You think real estate should hopefully go up, although you wouldn’t want to model that aggressively. Whereas with the ATM, it’s going down. That’s interesting.

Denis Shapiro: But they complement each other really well. So in my income fund that I have, most of that stuff is real estate. But the one non-real estate issue is the ATM fund. And it makes a small portion of the fund, but the reason why it’s there is because, like you know, apartment buildings have that wind up period; you have to factor in the closing cost and you have to factor in getting the rent bumps up and everything like that. So it might take 2-3 years to start seeing that high single-digit, double-digit cash on cash return. So during that time period, you can have something like notes or ATM funds balance out that cash flow. So you’re kind of getting a higher preferred return from day one, instead of being subject to that lower wind-up period if you only did one specific asset.

Joe Fairless: What’s the type of returns that would be normal to see, versus a red flag like, “Oh, wait, they’re overprojecting on this type of income for an ATM fund”?

Denis Shapiro: The ATM funds that I looked at – there were basically high teens IRR. But then the depreciation is significant; they’ll bring it into the 20s. But I don’t like to really factor in depreciation into returns, because it might not be applicable to everybody. So high teens are the standard. And most of the alternative investment world is actually really pitching one specific fund, but they’ll have different arrangements. So it will be one capital raiser, they’ll have their own little spin on it. But at the end of the day, it’s really—it goes back to one operator; from what I found that seems to be respected across the space. So it’s not like there’s a plethora of them out there, from what I found.

Joe Fairless: And going back to what you were saying early, I think I heard you say around year four is where you want to break even. So quick math – you’d want to hit 25% return a year through year four, right?

Denis Shapiro: Yeah. So it might be a little bit higher than 18, something like that… But it all depends on how you factor in the depreciation. But usually, the way that it’s structured, it’s – I believe, on a $52,000 investment, you get something like $1,000 a month. So if you factor in four years of that, you’ve basically got all your money back, and then five through seven you mak your money.

Joe Fairless: Man, that’s interesting. Before we go into the Lightning Round, one last question – are you still investing in single-family homes and short-term rentals? Because you mentioned short-term rentals weren’t what you expected and you had a single-family home, low-income property that wasn’t what you wanted either.

Denis Shapiro: So definitely no. Single-family rentals, probably never again in my life. I had every known stereotype known to man. So definitely not scalable. I would never look at it like, should I do a syndication or should I buy a single-family rental? It’s not even close, in my opinion.

The short-term rentals, I am fascinated by a few different models where — I have a family and I have three kids. So if there’s a way I could incorporate taking some really awesome trips and making some money out of it, that’s of interest to me. So I haven’t given up on the idea, just because they haven’t been the most successful in my past. It’s just something that I would want to network with people who are actually doing it really well, because I know a lot of people are crushing it in the short-term rental space. So it’s just more of, I know that it’ll probably be more time than I need right now to figure out how to do a right, but it’s something I wouldn’t mind doing in the future.

Joe Fairless: Based on your experience, what’s your best real estate investing advice ever?

Denis Shapiro: Network. Honestly, I go as far as to say, if you’re not willing to network, you probably shouldn’t be invested in alternative investments.

Joe Fairless: We’re going to do a Lightning Round. Are you ready for the Best Ever Lightning Round?

Denis Shapiro: Sure.

Joe Fairless: Best Ever book you recently read.

Denis Shapiro: I’m going to be a little biased here and I’m going to put my book, The Alternative Investment Almanac, just because after editing, I’ve probably read it 60 times; I’ve probably brainwashed myself during the process. So The Alternative Investment Almanac: Expert Insights on Building Personal Wealth in Non-Traditional Ways by me, Denis Shapiro.

Joe Fairless: Now is that the same one when I go to your website? The title is Ask the Experts: A Top Look at Nine Alternative Investments.

Denis Shapiro: That’s a free ebook.

Joe Fairless: Okay.

Denis Shapiro: On my website, I have two different free ebooks. So the way I structured the book is it’s a high-level intro to the topic, let’s say, apartment buildings. So you’ll get like a 20-30 page book on apartment buildings, and then it goes into two Q&A’s. So for my website, I broke out some of the best Q&A’s and I made just an ebook so people can download without having to read the 300-page book. If they want to read a smaller condensed version, they can just read the Q&A book. And then there’s another one that is just a primer on the different assets mentioned in the book.

Joe Fairless: Best Ever way you like to give back to the community.

Denis Shapiro: I know this is going to sound crazy, but I think it’s investing in real estate with good operators. I invested in a mobile home park about three years ago, and the park was in complete shambles. It was known as a meth park; there was 52 homes there, and within a span of three years, between adding lights, and evicting drug dealers and doing everything like that, it significantly improved the lives of all those 52 homes. So a lot of times investors are just focused on returns, but these are big projects. Joe, I know your projects are usually in the hundreds of units. So if you could go in and provide meaningful value, not extort the residents, but actually provide meaningful value, raise the rents properly and give them stuff that they want and love and are proud of living there, that’s much more effect than I can possibly do as a single person with one single-family rental. I can make that look nice, but it wouldn’t be the same impact across the board.

Joe Fairless: How can the Best Ever listeners learn more about what you’re doing?

Denis Shapiro: So the best place is my website, When you go in there, there’s the two free ebooks mentioned. Also, if you go on Amazon and put in The Alternative Investment Almanac: Expert Insights on Building Personal Wealth in Non-Traditional Ways by Denis Shapiro, it should come up. And reach out, I love connecting with investors as LPs or investors that are looking for an income fund, or just anything. I love talking to investors.

Joe Fairless: I see it on Kindle. Is that available on paper, too?

Denis Shapiro: Yep.

Joe Fairless: Okay, cool. Alright. Well, thank you for being on the show. If you’re able to find that SEC link to the top investments that have fraud, will you email it to me and I’ll ask the team to put it in the show notes?

Denis Shapiro: Yeah, absolutely.

Joe Fairless: Because I said no initially, because I thought I could easily search it. But my Google searching wasn’t very effective for the 60 seconds I tried. So yes, please share that.

Thank you for being on the show, Denis. Appreciate you sharing your insight into how you think about investing in different asset classes, and then how you underwrite deals, and how someone who doesn’t have the financial modeling experience that you have could still go about making more informed decisions prior to investing. So thanks for being on the show. I hope you have a best ever day and talk to you again soon.

Denis Shapiro: Thank you so much, Joe, for having me. It was a pleasure being here.

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