self-directed IRA and Scott Maurer

JF1285: What CAN You Do With A Self-Directed IRA? With Scott Maurer

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Scott is here today to help us understand what is possible and legal with self directed IRA account. You may be surprised by how many investments you can buy with a self directed IRA. You may also be surprised at what you can’t buy. If you enjoyed today’s episode remember to subscribe in iTunes and leave us a review!


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Scott Maurer Background:

Director of Business Development for Advanta IRA, a self-directed IRA administrator.

A licensed attorney and has worked with self-directed IRAs since 2006

-Advanta IRA has close to $1billion in assets under management

-Scott frequently gives seminars and webinars on the subject.

-Say hi to him at

-Based in Tampa, Florida

-Best Ever Book: Grapes of Wrath


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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, and this is the world’s longest-running daily real estate investing podcast. We only talk about the best advice ever, we don’t get into any of that fluffy stuff.

With us today, Scott Mauerer. How are you doing, Scott?

Scott Maurer: Great, Joe. How are you doing?

Joe Fairless: I’m doing well, nice to have you on the show. A little bit about Scott – he is a self-directed IRA expert. In fact, he’s the director of business development for Advanta IRA, which is a self-directed IRA administrator. He is a licensed attorney and has worked with self-directed IRA since 2006. He is based in Tampa, Florida. With that being said, Scott, do you wanna give the Best Ever listeners a little bit more about your background and your current focus?

Scott Maurer: Sure. I started with a company back in 2006, and when I started at Advanta it was just a few of us here. At that time was really the time when I think self-directed IRA’s really began hitting on a lot more people’s radar, with the last real estate boom. So I was brought in and I started with the company in handling a lot of the initial transactions, people going through the process of buying and selling real estate and other assets through their IRA account. My position really morphed from doing that as I learned more about the business, to focusing more on the education, networking, and ultimately the sales and business development side of things… And teaching classes – teaching webinars, seminars, just networking with individuals and trying to spread the word more about what self-directed IRA’s are, and how they can be used; there’s certain things that you can’t do with them, but that’s certainly what I’ve spent more of my time doing, and that’s really our current focus right now, and really it has always been – to educate as many people as possible that what you can do with IRA accounts that a lot of people simply just don’t realize it’s possible.

Joe Fairless: What are some of those things?

Scott Maurer: As we’ll talk about today, it’s investing in real estate, whether you are an investor who wants to buy single-family properties, you wanna buy properties to rehab, you wanna invest among many other individuals on some type of multifamily project and have your IRA owning a piece of the pie, lending with your IRA account; we have people wanting to buy cryptocurrency in their IRA… There’s so many different things you can buy within your IRA, you just can’t buy life insurance or collectibles – the only two types of investments the IRS prohibits inside your IRA account. So when you have an IRA with a brokerage firm or a bank, they’re limiting you to those items that they sell, those particular investments that they sell and make money from… But the IRS regulations allow for so many more different options than what you typically would have it you don’t look outside that box.

Joe Fairless: Unless I’m mistaken, there’s also some other things you can’t do, like lend money to your family and things like that, right?

Scott Maurer: Correct, yes. Prohibited investments are life insurance and collectibles, and there’s also… When your IRA is for instance buying rental properties or is lending money from your IRA, there’s certain individuals – basically, yourself, your parents, your grandparents, your children and grandchildren – that cannot transact with your IRA or really benefit.

When we talk about buying real estate in an IRA, we do talk about the standpoint as a pure investment vehicle; it’s not something that you can use your IRA to buy a vacation home or buy a primary residence within the account. That’s not allowed. So it’s strictly from that standpoint a pure investment inside the IRA. It’s the alternative to putting your money in stocks or mutual funds or bonds, it’s having this other options of investing in real estate and these other types of assets.

Joe Fairless: What’s a challenge that you’ve come across with this process that recently has made you think “Hm, okay, let me think through that a little bit. It’s not what I typically come across.”

Scott Maurer: Actually, I had a really interesting scenario recently. I had an individual wanting to, in the context of buying a piece of real estate – actually a very nice parcel of real estate, well over a million or two million dollars within an IRA… It was the standpoint of making sure he got all the financing, because he wanted to use his IRA, or a combination of his IRA, his wife’s and his dad’s to buy this property… But the issue he was gonna have was that he wanted to treat it more as a business, as a rental facility, as opposed to more like a rental piece of real estate. So he was transforming that idea of wanting to invest in real estate to really investing into a business using your IRA account. That’s something that is very tricky; it certainly is possible to do, but that’s something that recently I had it as a challenge and trying to talk through with that particular investor.

I spent a lot of time with [unintelligible [00:06:01].27] talking with him and his CPA about exactly how that could be structured if he was gonna go forward. I think that’s one of the more recent examples of something that’s kind of, again, outside the mainstream of what we see, that made it a little bit more challenging.

Joe Fairless: So if I’m understanding it correctly – and we don’t even have to use the specific person, but a person was looking to buy a piece of real estate, but was gonna operate it as a business? Can you just give us a hypothetical example, in case you can share a little bit of the details on this?

Scott Maurer: Yeah, the details — it was a property that I think was listed for around 1.5 million. Actually, it was built as a single-family residence, a huge, huge property… But his idea in buying this property was not to simply buy it and then rent it for rental income, but actually transform that property from a single-family residence into a commercial kind of event planning rental space, where you could host weddings and other types of conferences or things of that nature.

For him the difficulty in figuring this out is that when you’re investing in real estate with your IRA from kind of a residential or rental perspective, that’s more of a passive investment; you’re receiving rental proceeds back to your IRA, which is fantastic. But what he was looking at doing is operating it as a business, in which he was going to work for the company that is operating this event rental facility. So it was challenging for him, because there are specific rules as we’ve mentioned, that you can’t benefit from things going on inside your IRA specifically, so it was trying to find the right vehicle that was gonna make that possible and structure it…

He ended up not going forward with the deal… Not because of that reason, just because of transforming a residential property into a commercial event space apparently was a lot more involved than he had anticipated.

Joe Fairless: Yeah, but it wasn’t because he couldn’t do it, from your perspective, it was because the deal just didn’t pan out.

Scott Maurer: That’s correct. That ended up killing the deal when he realized it wasn’t gonna happen because of the different structural engineering projects that would have to take place to make it a commercial space… But we never got fully to the point of using the IRA as a 401k type situation having the business, although I think his CPA was on board with that. I think that would eventually – if he’d bought the property, that’s how they would have gone.

We were able to work through that issue, it just turned out the property itself didn’t work out for him.

Joe Fairless: Okay, so theoretically if the economics of the deal worked, then there was a way to use this self-directed IRA to do the transaction.

Scott Maurer: There was, and it involved in that scenario using your IRA and setting up this new business venture that he was going to form for this event facility, of establishing a 401k plan for that facility and using his IRA through that 401k to fund a business that he can work with. It’s a very kind of narrow concept within the IRS regulations that allows for that. It does have to be a 401k, but again, that was a challenging topic, because it started from the aspect of someone calling in and getting our name to buy real estate in an IRA account and having that morph from that initial discussion, which is again, something we deal with on an everyday basis, to something a little bit obviously more advanced, and not just simply being a piece of rental property that’s gonna collect rent 12 months a year, but actually transforming it into a commercial space that he wanted to work with… It just added so many more factors into it.

Joe Fairless: What’s the question that you get asked the most often?

Scott Maurer: I think one of the questions I get asked a lot is “Why haven’t people heard about this before?” when they call… Or then, of course, how the process works. I think the question when people find out about this, they say “Hey, I didn’t know this was possible… Why hasn’t someone told me?” The answer is simply your stockbroker, your financial advisor doesn’t always have a vested interest in telling you where else you can place your money. If you have an IRA or a Roth IRA account, or an old 401k, if you’re not looking for it, your typical advisor is not gonna tell you that self-direction is an option. That’s, again, a common question we get, is asking “Why haven’t I heard about this before? Is this something that’s new?” If they’re just hearing about it, they think it must have been something that was allowed in the last year or two, and actually it’s been around and allowed inside IRS regulations since 1975.

Joe Fairless: What’s your role with Advanta?

Scott Maurer: My role as the director of business development is to oversee basically the sales and marketing side of our business in both our Tampa office – our home office is in the Tampa Bay area; we also have an office in Atlanta. So as the director of business development, I’m overseeing the sales staff, the individuals who are talking to individuals who call in or who visit our website to get more information on self-direction, and all of us on the sales team also are just core educators.

It’s the incoming phone call, to talk someone through the process, or it’s again, teaching seminars or online webinars that we have as well, on these different topics… And just explaining the process, explaining the rules and helping people eventually just through education feel more comfortable about self-direction in general. [unintelligible [00:10:53].24] a concept going back to the common question we get of “Why haven’t I heard about this? Is this something new?”, people did wanna feel comfortable and reassure that what they’re doing is allowed, that they’re not reinventing the wheel themselves, so a part of our educational program and process is really to make it seem as easy as possible, because at its core, self-directing is really not that difficult to do, you’ve just gotta make sure you understand what you’re doing.

Joe Fairless: As the director of business development and you’re overseeing sales and marketing, your responsibility is ultimately, I imagine, to make sure you’re bringing in business and converting those leads into customers… What are some of the ways that you’ve found to be most effective for bringing in new business?

Scott Maurer: For us it’s really been networking with I think the right individuals. We focus a lot of our networking and marketing efforts in attracting CPA’s who’s clients obviously go to them for tax advice, and since IRA’s are a tax vehicle or a tax-saving vehicle, CPA’s are gonna get asked questions about self-directed IRA’s as well. So it’s really kind of forming partnerships and relationships with CPA’s, with some financial advisors who are open to the concept and who have clients asking about it.

Another area where we focus on attracting new business is people who are forming multifamily property partnerships or they’re doing large-scale investment real estate where they’re looking to raise several million dollars of capital from a number of individuals, and we can help those companies and show them ways in which they can advertise self-directed IRA’s to their investor base and help attract additional capital. That’s really what we focus on on the business development side – those kinds of strategic partnerships, and then again, just helping CPA’s, financial advisors, real estate investment professionals as well understand what the process is and then making it as easy as possible on the clients and the actual investors who are using their IRA’s to make the investment.

Joe Fairless: CPA’s and then also people putting together deals, syndicators or fund managers… Maybe not fund managers, but definitely syndicators. Any other major groups that would be the ideal networking person, entity or professional?

Scott Maurer: Certainly branching off a little bit, attorneys to some extent, who have clients and have individuals who are asking them about creative ways to buy real estate. [unintelligible [00:13:18].00] CPA’s, the syndicators outside of the real estate space, we also try to work with a lot of private placement companies. Syndicators for real estate are forming an entity to raise capital to invest in real estate, and certainly there are other individuals in the financial world who raise capital inside of partnerships or LLC’s to invest in hedge funds or startup companies… Those are other areas ancillary to real estate that we focus on.

Joe Fairless: And how do you reach those – we’ll talk about the CPA’s and the attorneys – professionals?

Scott Maurer: Well CPA’s, for one, and attorneys a little bit to an extent as well – we teach… Again, this is part of our idea of education being so important… We do continuing education classes. For CPA’s we have a two-hour proved course we offered online. We’ve done some in-person as well for attorneys and CPA’s. We provide them that education of a little bit on IRA’s in general, because not all CPA’s are as versed in the intricacies of IRA’s and contributions and distributions etc., but talking to them about that and also talking to them about what self-direction is. So we do a lot of the educational programs, webinars and seminars, and certainly reaching out to those CPA’s that are in our areas – either in our Tampa or Atlanta market – and meeting face-to-face with them, sitting down and having lunch, going to their office or whatnot and really explaining what we do.

A lot of times we’re getting calls from them [unintelligible [00:14:42].29] the incoming call from a CPA who reached out to a fellow CPA who knew about us, and from that standpoint educating them on what’s possible, so that when they get a client that’s interested or is asking questions about “I heard something about real estate with an IRA account. How does that work?” The CPA at least just knows to forward our name along to them to get the questions answered.

Joe Fairless: I asked those specific questions for two reasons. One, just to understand your approach, and for the Best Ever listeners who are passively investing in deals to understand if they are speaking to a CPA and their CPA is not well-versed on this, then who to talk to… But then also for anyone who’s looking for private investors… So a multifamily syndicator or a fix and flipper – you’re basically targeting the gatekeepers of the people who have access to a lot of individuals who have money, and as a fix and flipper or a multifamily syndicator, also building relationships with CPA’s would be beneficial, because we can then have relationships with someone who has relationships with a lot of people who have money.

Scott Maurer: Yeah, without a doubt. That’s why we try to do a couple things from a marketing standpoint to help syndicators and people who are raising capital. We’ve created a personalized landing page for them that we host, that they can put their logo and their information and use that if they’re looking — again, soliciting for more capital… An easy way to do it, if a syndicating is not using IRA’s already, it’s a good way and an easy way to get more capital invested in your deal without really having to go out and find that new investor… Because you already have your stable of investors that you’re working with, many of whom don’t realize that they could invest more with you or invest in different projects by simply using their IRA accounts.

So we provide this landing page, we can provide some other marketing collateral that’s somewhat personalized for your company and your syndication, to help you reach out to those individuals, and kind of just letting people know that if you are interested in the deal I’ve put together – I’ve put together this syndication; here’s my ideas for an investment and I need capital… Just letting the individuals know “Here’s another resource for you to put that money in the deal, because you might have a lot of investors who would like to invest more, they just don’t think they have it, because they’re looking at their savings account or their own personal accounts, not even thinking that “My IRA or my 401k that’s been sitting there for years could even be used.” So you’re right, we turn to those gatekeepers and let them know “Hey, here’s another way to raise capital.”

Just a quick side-story – we had a company here in the St. Pete area in our Tampa Bay market that was raising private capital for their new startup insurance company. They included just a couple blurbs about self-directed IRA’s in our company in one of their offering pieces and were able to raise several million dollars more in capital just from letting the people they already were working with know that they could buy additional shares or make additional investments using an IRA account. That was obviously very powerful for them, and we’ve seen other syndicators that have used that type of platform be successful as well.

Joe Fairless: What is your best advice ever for real estate investors?

Scott Maurer: I think for when it comes to IRA’s it’s if you’re working with other people. If you’re a real estate investor out there and you are looking for more capital – and it seems a lot of real estate investors typically are; you’re always looking for your next deal – is to keep the IRA in mind when you’re talking to someone else. Not something that’s gonna be the panacea for all capital raising needs; you’re not gonna run into people that always have IRA’s available… But remembering however that there’s option out there, because again, I think a lot of people are unaware that an IRA could even be used in that context to make an alternative investment, number one. And number two, they’re not happy with where their funds are sitting. So not only do they not know it’s possible, they have their money sitting maybe in a CD, or maybe it’s in a stock market that’s great one year, but they know there’s gonna be a correction coming at some point, they don’t wanna be on the wrong side of that correction – it gives them the ability to put that money with you into something else, something alternative that’s not tied to those other markets. I think that’s the best piece of advice for a real estate investor.

Sure, a self-directed IRA can be great for you if you have your own IRA, but don’t forget about the millions of other people that have retirement accounts as well, that could help provide capital for your deals.

Joe Fairless: Are you ready for the Best Ever Lightning Round?

Scott Maurer: Sure.

Joe Fairless: Alright, let’s do it. First, a  quick word from our Best Ever partners.

Break: [[00:19:06].23] to [[00:19:52].05]

Joe Fairless: Best ever book you’ve read?

Scott Maurer: Grapes of Wrath.

Joe Fairless: What’s a mistake you’ve made in business?

Scott Maurer: Not always seeing the opportunity for growth.

Joe Fairless: Best ever way you like to give back?

Scott Maurer: I love to volunteer my time with youth sports.

Joe Fairless: And how can the Best Ever listeners get in touch with you?

Scott Maurer: They can reach out to me, I have a 0800 number – 0800 425 0653 – and simply ask for Scott. They can visit our website at Go to our Meet the Team page, you’ll see my picture and you can click right on there to send me an e-mail.

Joe Fairless: Scott, thank you for being on the show and talking to us about self-directed IRA investing, the things we can’t invest in – life insurance, collectibles are things we can’t do – and things we can invest in. Then the creative solution that you came up with or really had to think through, with the one scenario that we talked about with setting up a business, and then the approach that you take to building out the business and building out new leads and building relationships.

One, you identify who your target audience is, who happen to be gatekeepers, and then you have an education platform and then you build relationships through that education, and it’s a spiral up effect.

Thanks for being on the show. I hope you have a best ever day, and we’ll talk to you soon.

Scott Maurer: Thanks, Joe.

Dave Sobelman and Joe Fairless

JF1272: How To Be Proactive & Have A Vision For What Will Happen #SkillSetSunday with Dave Sobelman

Listen to the Episode Below (27:46)
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Dave is a previous guest on the show who specializes in triple net leases. Today he comes back on the show to talk about how he and his team try to predict certain things that will happen and be proactive in solving problems before they even come up. Dave gets a lot of people asking him how he “does so much”. He attributes being on top of everything all the time to his time spent working at The White House. If you enjoyed today’s episode remember to subscribe in iTunes and leave us a review!


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Dave Sobelman Background:

  • Founder & CEO of Generation Income Properties (a public net lease REIT)
  • Founder of net lease brokerage firm 3 Properties.
  • Managed more than 1,000 single-tenant net lease transactions and has been involved in about $10 billion in transactions
  • Began his tenure in commercial real estate as a Research Analyst and Associate for Grubb & Ellis Company
  • Was responsible for maintaining market data for over 134 million square feet of area properties and accurately forecasting regional trends for client assessments
  • Based in Tampa, Florida
  • Say hi to him at


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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, and this is the world’s longest-running daily real estate investing podcast. We only talk about the best advice ever, we don’t get into any of that fluffy stuff.

With us today, Dave Sobelman. How are you doing, Dave?

Dave Sobelman: I’m doing great, so fun to be with you again. Thank you.

Joe Fairless: Yeah, nice to have you back on the show. Best Ever listeners, first and foremost, I hope you’re having a best ever Sunday, and because today is Sunday, we’ve got a special segment for you called Skillset Sunday. You’re gonna walk away from this episode with a particular skill that you can hone if you already have it, or you can acquire if you don’t have it already.

The skill we’re gonna be talking about today is how to be a productive, proactive person who’s got a vision for what’s about to happen. And we’re not talking some mystical stuff, we’re talking about practical things you can do in your life to make that happen.

We’re gonna be talking to a previous Best Ever guest. Dave was on episode 1168, titled “How to Have Your Tenants Pay Taxes, Insurance and…”, what’s the rest of that title?

Dave Sobelman: Maintenance.

Joe Fairless: Maintenance, thank you, sir. A little bit about Dave – he is the founder and CEO of Generation Income Properties, which is a public net lease REIT. He’s managed more than 1,000 single-tenant net lease transactions and has been involved in about ten billion dollars worth of transactions. Based in Florida.

Before we dive into it, Dave, do you wanna give the Best Ever listeners just a refresher of your background?

Dave Sobelman: Absolutely. So I am the founder and CEO of a public real estate investment trust called Generation Income Properties, as you mentioned. We focus on net lease properties throughout the country, typically in the top 20 highest density cities in the United States. I also founded a brokerage firm that helps people buy and sell triple net lease investments throughout the country. That’s where my background started, in this very niche product type.

Lastly, I am one of the founders of an algorithm that focuses on triple net lease valuation, using actual metrics and data, and really trying to quantify subjectivity as it comes to the valuation of net lease properties. That company is called Vero, which is Latin for “truth.” That’s my immediate background and where I spend the majority of my time.

Joe Fairless: So with these things, clearly you’ve accomplished a lot and are continuing to accomplish things and performing at a high level… So walk us through the background for today’s conversation, because with this show I do do returning guests, but I always do a special segment with them, and that is either Skillset Sunday or Situation Saturday. I know when you and I were talking prior to this recording, you talked about the background for the focus of today’s episode and where it was coming from. Can you talk about that?

Dave Sobelman: A lot of people ask me, they say “You do so much, you’re so productive. How do you manage running three companies? How do you manage the staff that comes along with that? How do you manage the people and the tasks at hand, and writing books, and being published, and speaking around the country? How do you get all of this done?” And in my mind, it’s become very simple, but I understand from an outsider’s perspective it seems pretty unique.

The basis of my background or the skillset that I think that I’ve developed over the years comes from my time before real estate, which is when I worked at the White House. At the White it’s a very fast-paced environment. You have to think quickly, you have to think accurately for the most time, and you just have to be on top of everything all the time.

Politics aside – we won’t get into a political discussion, or which president I worked for – but every staffer (which is what I was) who works at the White House either has or has developed the skillset where they can accomplish a lot in a very short amount of time.
I was on the president’s advanced staff, which is a position at the White House that most people don’t know about, and it’s where you travel before the president, anywhere in the world, up to a week or two weeks ahead of where they go, and you establish the political logistics of their trip. In essence, who they’re gonna meet with, where they’re gonna meet, who will be in the room, what it will look like on TV, and sometimes the content of their meeting. And you prepare all of this for the president before he arrives.

So when the president does arrive at any place in the world, you typically meet them at the Airforce One; he walks down the stairs and you start briefing them on exactly what they’ll be doing on that trip and who will be with them. You’ve had all of this preparation for a week or two beforehand to educate yourself, which in turn allows you to very quickly and accurately brief the president on what he’ll be doing on that trip.

So you have to develop the skillset to be ahead of yourself and anyone else, and always think of every contingency that could happen in any scenario, and on top of that being prepared for it.

Joe Fairless: What type of training is involved to have that skillset?

Dave Sobelman: There’s no formal training. It’s not like you study this in school. I didn’t study political science, I didn’t study law… I learned this skillset by being around people who demand this sort of level of service within their lives. So you typically start at a very low position when you’re at the White House, where they don’t put you anywhere near the president, but you’re just working for the people who are near the president. You develop that skillset by watching what they’re doing over a period of time.

So it’s just helpful to completely think of any task at hand as not at what’s immediately in front of you, but what you’re ultimately trying to accomplish and who are the different players involved and what their roles are in each aspect of that plan.

Joe Fairless: When you were watching people over a period of time when you were starting out, what were some of the things that you picked up on?

Dave Sobelman: That’s a great question. A lot of times we’re putting a lot of effort and emphasis into aspects of our lives or aspects of our work that isn’t important to the big scheme of things. An example of that – one of my first assignments as working at the White House was working with the media. A lot of people don’t know that literally wherever the president goes at any point in his day, there is always media involved, because it’s deemed that the president is creating history from any aspect of their life… So from a state dinner, to visiting a foreign country, to doing a speech on a specific policy event, to going to play golf, or going for a run. That’s all considered history, so there’s media with him all the time. Even while the president is sleeping, there’s someone at the White House to report on any events that may occur at the White House that directly affect the president.

So one of the first jobs that I was assigned to was to work with the media and to see how they go about reporting what’s happening, both from a video perspective, and then — they call him pencils, people who are writers, where they don’t have a camera in hand; they’re just writing down what’s happening.

It was my job to coordinate the movements of the press, because everything is very coordinated. So being in a room with some of the well-known media outlets throughout the world and with people who you’d recognize by TV appearances all the time forced me to be in a position to be ahead of them all the time… So what are they trying to accomplish by being in this room with the president right now? What is the story that is coming across with the words that the president is using? What is the angle of the photograph that that photographer is trying to make, and what the background of that photograph and who else is in that picture with the president, and what message are you trying to convey with this particular presidential appearance.

My job was to think about all of those things, so as the media moved with the president, that they were capturing the story in which they were trying to accomplish.

Joe Fairless: When you internalized that and then you apply it, what are some things that you do to influence it one direction or the other?

Dave Sobelman: You know, I still use all of those skills in my real estate practices today. So let’s take a net lease transaction, for instance. I figured out at one point that there could be as many as 23 different people involved in any one transaction, everyone having a different role within that transaction. So whether you’re the buyer, the seller, the attorney, the engineer, the surveyor, the title person – whoever you are within that transaction, that you have a role… And from a brokerage perspective, it’s the broker’s job to coordinate that entire transaction, that entire effort.

So transferring those skills of being ahead, of coordinating people, truly being a leader within that and making sure everyone’s accomplishing their job, with the end goal in mind to complete that transaction. It’s something that I’ve transferred very easily to the real estate market. So over my time, as I developed my skills at the White House, I was promoted to different positions where I ultimately became what they called a lead advance person, meaning that I would not only just be part of the media, but I would control the entire trip, and having conversations directly with the White House beforehand, and reporting back to make sure that our efforts on the day of the president’s arrival are extremely coordinated and well-documented. So not only would I have to work  with the president’s White House political staff, but I’d also have to work with the president’s security, which is the Secret Service, and also with the United States military, which came with different roles, a lot of it being communication with the United States army, with air transportation, with the Airforce or the marines, and as the lead advance person, it’s your job to make sure that everyone is completing their task at hand.

So the organizational effort that goes into any movement that the president has is extremely time-consuming, but at the same time extremely detailed. So it really looks effortless when the president’s doing what he’s doing, but in the background there’s dozens and dozens of people who are involved in every effort he’s doing. As the lead advance person, it’s my job to control each one of those efforts and to make sure that the president is doing exactly what we have planned for him to do at that point.

Joe Fairless: Bringing it back to real estate like you did, and the 23 different people in a transaction, one thing you mentioned is you want to recognize there are lots of people in a transaction (23) in the case that you were looking at, and then understand the role that each person is trying to accomplish… What if there is a person, one of those 23, that you know the role they’re trying to accomplish – you could just look that up on Google, or something (what is this person’s role?), but the way they’re going about it is perceived to you as they are sabotaging the process, or they’re just incompetent… Then you know what they’re looking to accomplish ideally, but they’re just not going in the direction you want it to go.

Dave Sobelman: I found in my career that it’s better – and I would just be very frank about this – to call those people out directly. I choose to handle things privately in the first instance, and  have a very reasonable, professional conversation, pin-pointing that person and letting them know that I understand what they’re doing is not accretive to this process, and I hope that we change things and maybe give them suggestions on how to change them. If that doesn’t work, then essentially we bring it out to the collective good of those 23 people or so, or I should say up to 23 people, and letting them know where the weak link is in this process, just so everyone’s aware that I have identified it, I’m trying to work on it, and that’s it’s not (using your words) “sabotaging” the entire process. Everyone else typically can be a professional about it and realize that there is a weak link, but we’re working around it. I’ve had to do that many times in my career. Not everyone has the best of intentions, although we go into it hoping that they do.

I’ve been in positions where I’ve learned this trait by traveling throughout the world. In every country that I would attend there’s a negotiation point and there’s different styles of negotiation. For instance, when we were negotiating with the Chinese government on the president’s trip to China, the Chinese nationals are extremely shrewd negotiators; they’re excellent and expert negotiators on the different aspects of what we were trying to accomplish within that trip. We have to be able to communicate well, not only with our own team, because now we’re dealing with a whole other set of circumstances, which is an entire national government. So being able to fluidly get through this process and being ahead of what we are perceiving to be issues was always very helpful, so when the president does arrive and/or when a transaction does happen, these issues have already been dealt with.

Joe Fairless: How did you and the team come to a satisfactory conclusion or agreement in that scenario with the Chinese nationals, knowing that (to use your words) they’re excellent negotiators?

Dave Sobelman: Well, understanding who you’re working with beforehand is probably step number one. Assessing your situation, knowing what environment you’re going into is extremely important, because real-estate specifically – and we’ll get back to negotiating with the Chinese government – it’s a very dynamic industry. Properties right next door to each other each have their own dynamics, their own circumstances – different owners, different values, different surveys… There’s differences even in properties right next to each other. So assessing not only the real estate aspects of a specific transaction, but the people involved in those transactions and how they want to accomplish this process (whatever process you’re getting into) is step number one.

Relating that to my work with (in this case) the national government is we knew upfront that they’re shrewd negotiators, and now here we as Americans in a foreign country, and therefore you have typically lower leverage in which to negotiate, because you’re not in your homeland, you don’t have your own people surrounding you… And I’m not saying that from a very polarizing perspective, it’s just there’s a reason that there’s different countries – everyone has their own cultures, and their way that they go about doing business… We weren’t in the United States anymore.

I had the ability to prepare for my time in China by learning their cultures and the way that they do business, and how someone in the Chinese government may respond to a request that we have, and being prepared for that up-front just goes back to the thesis of doing your advance work – being prepared and knowing what you’re getting into before you start.

Joe Fairless: So the key is to learn the culture, learn who you’re gonna be working with and then approach accordingly?

Dave Sobelman: Absolutely. And that’s something that I think has allowed me to run my business currently – knowing the different people and the different scenarios that we’ll be involved with in any stage of our development and growth.

Joe Fairless: Now we’ll bring it back to real estate… When you’re doing research on who you’re gonna be working with or negotiating with, what questions should you be asking yourself and what type of research should you be compiling?

Dave Sobelman: Almost like an attorney… Not quite like an attorney, but almost like an attorney, you wanna be prepared for everything. So if you’re going into a transaction, you wanna know exactly what your end result should be, what you want it to be, before you start that transaction, before you start at negotiating, before you start your first offer on that property… Because usually there’s a negotiation with any real estate transaction, and everyone’s trying to get a good deal; both sides are always trying to get the best deal for themselves, but what is your walk away point? Where can you say “This just doesn’t make sense anymore?” Having that up-front in your brain, in a spreadsheet, however you’re structuring your own underwriting is paramount to the process.

Joe Fairless: To know what your walk away point is, and then be prepared for everything — but “everything” is pretty broad by definition… I’m gonna use some stupid example so you can rein me in a little bit. Do they like Fruity Pebbles or do they eat oatmeal for breakfast? What exactly should we look at, what are the most important things we look at? Because we’ll go insane if we try to be prepared for everything [unintelligible [00:20:46].20]

Dave Sobelman: Yeah, that’s fair… So you’re ultimately ending up at a price, so you should come starting with what’s your walk away price. I’ve made several mistakes early in my career where I was not prepared to understand what the value of a specific property would be, and purchasing that property at the wrong price, so when it came time to exit that property for whatever the reason, you can lose money, or not make money. So price is first.

The people involved – everyone says that real estate is a very people-centered business, or a relationship business, and developing those relationships over a period of time is important to the growth of yourself and your connections, but knowing the people involved… And let’s get specific about that – some people, like I mentioned, are shrewd negotiators and you just know that everything that you’re gonna do with this one particular person may be a negotiation. Other people may see the bigger picture and they’ll say “Listen, I’m willing to leave a few dollars on the table in order to get this transaction done quickly, because in that case I can get my money back and invest in the next project, and I’ll make a few dollars there, and over time, in aggregate, I’ve made a lot of money.” So there’s different types of people – some who are looking for the last penny, and others who are cycling through deals pretty regularly.

In my case, we work with attorneys on every single transaction. There’s always an attorney involved, and having an attorney who’s a deal maker, while also protecting your interest, is also really important. Sometimes the attorneys I work with are not licensed in different states in which I work, so we need to find other counsel in different markets, and that forces us to start that vetting process all over again, and finding that deal-maker who’s also protecting us.

These are just several examples of how to assess the everything that I mentioned, but getting granular about the different aspects of the transaction is something that you just learn over time by having to be prepared for each one of those.

Joe Fairless: Anything else you want to mention as it relates to — you’ve talked about two skillsets; you gave us a bonus one, thank you for that. One is being a productive, proactive person, and two is negotiating tips.

Dave Sobelman: Yeah, just to go back to the original topic we started discussing, which was being ahead of yourself all the time… I really can’t stress this enough of how important it is and how productive you can be by giving yourself the chance and the ability to not just be productive, but being overly productive, to a point where people are not only shocked by how much you’re able to accomplish, but impressed. And that leads people to be attracted to the work that you’re doing and how you’re approaching these different situations.

People use phrases like time management or organizational skills, or all of these catch-phrases that we try to adopt in our lives at different points, but in my opinion the real way to handle multiple tasks at one time is just to think way ahead. Be a slave to your calendar, and think about the different people that are involved in each aspect, communicate what you’re trying to accomplish with each one of these goals that you set, and implementing those goals through that work. So multi-faceted, for sure; not something that’s easily adopted or easily learned, but something that over the years — I won’t say I’ll ever be an expert in this, but I’ll say that I’m able to educate others on how I go about accomplishing a lot, with little time in my life.

Joe Fairless: Great advice, and I will attempt to summarize here in a second, but first, how can the Best Ever listeners get in touch with you?

Dave Sobelman: You can reach me by e-mail, and you can get that through my website, which is (Generation Income Properties REIT). I’m happy to discuss any of these topics with anyone at any point.

Joe Fairless: Outstanding. So, correct?

Dave Sobelman: That’s it, thank you.

Joe Fairless: Perfect. Well, thank you for being on the show and giving us insight into how you’ve gotten some skills that you’ve used to get to where you’re at, and how we can apply those skills in our own lives as real estate entrepreneurs. One, the first skill we talked about is being ahead of yourself, as you call it – and everyone else, quite frankly, most likely… And by how we can apply that in our life moving forward. One is think way ahead. When we think way ahead, we need to have a vision for what we ultimately are trying to accomplish. Then we need to think of the people who are involved in that process, put together a plan and communicate the plan of what we’re trying to accomplish, while being calendar-centric to make sure we’re staying on point.

Dave Sobelman: Well summarized.

Joe Fairless: Well, thank you, sir. With negotiating, the most important thing we’ve got to identify before entering into any negotiation is what is our walk away price… Because without that, we might get caught up in a whirlwind of stuff that might seem relevant at the time, but ultimately it’s not if we’re not getting our walk away price – or, I imagine terms, too; you’d probably throw in price and terms in case they give us crazy good terms and the price might be able to be compensated for that… Is that accurate?

Dave Sobelman: Very fair, yes.

Joe Fairless: Cool. Well, thank you for being on the show. I hope you have a best ever weekend, and we’ll talk to soon.

Dave Sobelman: Thank you very much.

Asset Class domination

JF1230: Finding An Asset Class With Less Competition And Dominating It #SkillSetSunday with Tyler Sheff

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When Tyler is looking for deals, he loves to find 5-50 unit deals. This is an interesting space because it cuts out the smaller investors who are intimidated by multifamily, simultaneously you cut out the bigger investors because the deal is too small for them. The biggest contributor to Tyler’s success he says is not assuming anything anymore, rather always asking questions. We get to hear great tips on how Tyler negotiates hs deals, be ready to take notes. If you enjoyed today’s episode remember to subscribe in iTunes and leave us a review!


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Tyler Sheff Real Estate Background:

Founder & CEO of & CashFlowGuys Podcast

-Commercial Real Estate Broker, Investor and Syndicator

-Over 16 year’s experience in real estate

-Based in Tampa, Florida

-Say hi to him at


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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, and this is the world’s longest-running daily real estate investing podcast. We only talk about the best advice ever, we don’t get into any fluff.

With us today, Tyler Sheff. How are you doing, Tyler?

Tyler Sheff: Hey, Joe. How are you doing today?

Joe Fairless: I’m doing well, and welcome back to the show. Best Ever listeners, if you recognize Tyler’s name, well then that’s because you’re a loyal Best Ever listener. If you don’t, well then shame on you, you should be a loyal Best Ever listener, but welcome; glad you decided to listen. Tyler was interviewed on episode 783, and the title of that episode is What He Did Immediately After Paying $40,000 for a 26-unit Memphis Property He Bought Remotely. That’s a mouthful, but that certainly is intriguing; if you’re curious about it, then go check out episode 783.

Today we’re gonna be talking about a specific skill that has helped him in his real estate endeavors. Because today is Sunday, and that’s what we do on most Sundays – Skillset Sunday.

Tyler, in addition to the lead-in I just mentioned, he is the founder and CEO of and The Cashflow Guys Podcast. He’s a commercial real estate broker, he’s an investor, and he’s a syndicator. He’s got over 16 years experience in real estate. Based in Tampa, Florida. His focus really is buying non-performing notes and apartment buildings 50 units or less. With that being said, Tyler, how about briefly — just give the Best Ever listeners a refresher on you and your focus, and then we’ll dive into this skillset today.

Tyler Sheff: Well, as you’ve said, my focus is multifamily; I like the smaller stuff – there’s a space I play in, the five to fifty unit space. I don’t have a lot of competition. It’s just a little too big for the single-family guys, they’re usually scared of it because it’s multifamily, and the bigger guys, guys that are playing in the big leagues like you are, it’s a little too small for you, it’s not worth your time. So I kind of exist in this space where there’s only a few of us that are buying in this space, the mom-and-pop type arena, and I like that space, I do.

Joe Fairless: I know we were gonna talk about the skill of asking questions and not assuming the answers, and we’ll get to that, but I wanna follow up on this five to fifty space, because it’s a thing that’s really interesting. Is that okay?

Tyler Sheff: Absolutely.

Joe Fairless: Alright, cool. Management is the first question that I bet you get a lot from people – how do you pay for a manager if the property doesn’t pay for it, and how do you allocate that? What’s your response to that?

Tyler Sheff: As we all know, we make our money when we buy, so it all comes down to building those costs in in advance. When I factor management, I’m always coming in at 15% to 18% as a management cost, therefore it forces me to negotiate a deal to pay for all my management expenses. It’s a little trick that I use to force myself to do what I’m supposed to do.

Joe Fairless: Okay, so you make sure that you have that line item in there, and it’s 15% to 18% of what?

Tyler Sheff: Of the annual income.

Joe Fairless: Of the annual income. Okay, 15% to 18% of the annual income is allocated to management… And where are you netting out after you see those expenses? Is it in that range, or is it a little bit lower?

Tyler Sheff: We’re averaging — as far as ROI, or cash-on-cash return?

Joe Fairless: I’m asking is it truly within the 15% to 18% of the annual income once you start operating the property, or is it a little bit lower?

Tyler Sheff: I find it usually between 10% and 13%, that’s the true number. I like to have a little bit of fluff in there, a little bonus money at the end of the year.

Joe Fairless: Okay. The actual management of let’s say a 50-unit, how do you structure that team?

Tyler Sheff: The properties I have in Memphis now – and I’ve been growing over some time – we’ve added some properties, taken away… We’ve got one management company that manages everything for us. They primarily manage smaller assets, that’s kind of their niche. They don’t get into the big stuff, so initially, part of that 50-unit limit came to what their comfort zone is, the type of clientele that they’re used to dealing with.

I’ve dealt with a lot of bad managers, Joe; I’m sure you have gone through that as well…

Joe Fairless: Yes, absolutely.

Tyler Sheff: When I find a good one, I’m in love. I’m gonna buy what they like to manage, and that’s what I’ve stuck with.

Joe Fairless: I understand that approach. As far as the management goes – that’s one big thing for why people say “I don’t wanna do 50, because the property doesn’t support it; I need to do 100, because then I can hire full-time staff”, but you’re just saying, “Hey, budgeted in on the front-end, so that the property can pay for it.”

Tyler Sheff: Absolutely.

Joe Fairless: Okay, what are some other reasons why people say “I don’t wanna do 50, I’d rather do 100”?

Tyler Sheff: Well, I’m not sure why people wanna go larger. To me, I’m very hyper-focused, I’m very conservative when it comes to my investing, first of all, so I’m gonna make sure, when it comes to due diligence – because as we’ve talked about in the previous episode we did, on episode 783, I’ve made a lot of mistakes, and I’ve lost money doing it, and I came away a better investor, I came away a better syndicator, I came away a better broker by going through that emotion of losing it. So for me, if 50 to 100 doesn’t really matter, but when I’m investing in a certain market and I’ve got a manager that they just like to me in that 50-unit space so they don’t have to put somebody on staff, they like to run a lean operation where they don’t have people all over town on site, that’s their reasoning – it makes sense to me, so I go with it.

Joe Fairless: Okay. You plug into an operation that’s already got the system and the expertise, and you kind of [unintelligible [00:07:48].26] definitely benefit from it already being in place… It makes sense.

Tyler Sheff: Absolutely.

Joe Fairless: Okay. Disadvantages to buying five to fifty, versus smaller or larger?

Tyler Sheff: It does take longer to scale, in my opinion. That’s a big disadvantage. Obviously, it goes a lot faster with 100 units, 200-300 units…

Joe Fairless: And when you say “scale”, what do you mean by that?

Tyler Sheff: Well, to grow my portfolio. If I’m looking at my income levels, I have to work a little harder than people do in a larger asset class; I’ve gotta think outside the box a little differently, and I’m not necessarily dealing with the same type of sophisticated owner (owner direct); I’m dealing with a little different seller than what you would be — you’re dealing with a hedge fund in your space, commercial brokers, big companies, stuff like this, where they talk about hundreds of doors… I’m almost always dealing with mom-and-pop, so the emotion comes back into the transaction, where it wouldn’t necessarily exist in the larger transactions.

Joe Fairless: Okay. And I think that is a good segue into asking questions and not assuming the answers, because when I asked you what type of skills you wanna talk about, that you’ve honed and you think it would be important for other Best Ever listeners to hone, you said “asking questions and not assuming the answers.” Do you use that skill when dealing with the mom-and-pop owners?

Tyler Sheff: I’ve gotta say across the board. It is what has helped me stay successful and profitable, 100%. I find that in every case, we as humans, we assume everything. This is why people don’t like each other on Facebook over three words on a post; somebody misunderstands it. They assume what the other person means, and then they have a freak-out about it. This exact same thing goes on every day in transactions.

I finally woke up one day and I said, “You know what? I’m just not gonna assume anymore, I’m gonna ask the question.” An example of that is let’s say I’ve got a guy by the name of John as my seller, and instead of me thinking “John’s not gonna take this offer. This offer is gonna insult him. He’s gonna get mad at me and he’s gonna hang up the phone and he’s never gonna call me again.” I pick up the phone and I say “John, I really wanna buy your property. As a matter of fact, I woke up this morning deciding that no matter what, somehow today you and I are gonna sit down, we’re gonna figure out how I can buy this property and help you out of the situation. Now, for that to happen, I can assume all kinds of things, but realistically, I’m not that smart and I’m probably gonna be wrong, and you may walk away upset. We both know I can only afford what the asset can afford to pay, and I can’t pay more for this property than what the asset can afford to pay, so let me ask you, John, what can this asset afford to pay?”, and I won’t say a word.

Joe Fairless: I would just say whatever the original price was.

Tyler Sheff: And I’ll restate the question, and when I do this… [laughter] Seriously, when I do this…

Joe Fairless: I’d say, “Well, I heard you the first time.” [laughs]

Tyler Sheff: And I’ll reiterate the fact that, “You know, I would love to, but here’s the thing – when we go into this transaction, we’re gonna have appraiser and bankers, and I’ve got investor partners coming in on this… We wouldn’t buy this just because it’s cool, we’ve gotta be able to make a profit, so… At this price point, John, how do I make a profit?” I put them in the driver’s seat, because I’m not gonna assume what they’re gonna say. And I can tell you, very often they come back around to our way of thinking.

Joe Fairless: The natural question there would be “Well, how much money do you wanna make off this?”

Tyler Sheff: Exactly, and I work on monthly numbers. In other words, I look at a return. I say “John, when you owned this property, was it profitable, did you enjoy it? Why did you buy this property?” I revisit why they originally bought it. Again, I’m constantly putting them in the driver’s seat, because I have no idea what they’re gonna say, but when they feel like they have the ability to be in control of the situation, I think the reality of it is I’m being a good listener, I’m letting them drive the car, and we’re gonna get to where we need to go if I give them the impression that they’re driving the car. If I listen to them, instead of just assuming.

Joe Fairless: So in that scenario, where you say “Hey, I’ve got investors, I need to make money off of this purchase…” and I say “Well, how much money would you need to make off of it?”, you don’t give a direct answer, you then answer that with a question of “Well, how much money did you need to make on it when you bought it?”, or what would your reply be?

Tyler Sheff: Every situation is different, but in that example I would probably say something along the lines of “John, the last couple transactions we’ve made, we’re looking for somewhere between a 16% and 18% return across the board. For us to be able to do that, after we go through the diligence process, we’re gonna have to really get down to brass tax.” Then I’ll go right back to him again – “When you bought this property, you were probably in the 25%-30% return, weren’t you?”, because I know his proud, because most men are proud… And he’ll say “Of course I was, yeah”, because you know, all investors are getting rich.

Joe Fairless: Of course, yeah. Everyone does.

Tyler Sheff: Yeah, yeah. Nobody ever does a mistake, nobody ever loses money. [laughter]

Joe Fairless: Right.

Tyler Sheff: Yeah, I’ve got six million units, that’s great. And why are you driving a Yugo? [laughter] Anyway, so I’ll revisit that, and they’ll always come up with a prideful number, which is beautiful, because now I’m always asking for a number just below what their pride number is. Again, I’m not assuming; I’ll let him drive.

Joe Fairless: Yeah, that’s interesting. I can hear that play out and how that would work. I could also hear the opposite response for — I’m thinking of a seller in my mind, a specific person, so maybe that’s what it is, but they’ve done a very good job investing in a local market, and they are incredibly tight with their finances, and they do self-management etc. and I think they would actually answer the question “When you bought this property, what were you looking for?” – I think they’d say something like “I was just looking to beat inflation, and fortunately we did, and we made a little bit more than that, but I’m looking to get a fair deal”, and then they go back to “I need to retire, and I can’t retire off of the amount that you’re offering.”

Tyler Sheff: Well, you know, I’d absolutely agree with you, Joe… It’s tough to retire in today’s society. “What does retirement look like for you?” I’m gonna get them to verbalize that to me. “What does that mean? Because if I give you a pile of cash, Joe, if I give you three million dollars for this apartment building, we’re gonna put three million dollars down on the table, can I come back 12 months from now and visit it? Will it all be there? Of course not; you’re gonna do something with the money. Retirement is what that is… Tell me about that. What does that look like?” I’m focused on him and his pain, I’m not necessarily focused on the deal.

Obviously, it’s not bulletproof, no plan is, but when I’m focused on the seller’s needs and not on my own, and I get them to verbalize and get comfortable with me… And I’m not a one-hit-wonder, so I’m not one of these people that walks in and just [unintelligible [00:14:30].24] some mobile home wholesaler. This is a process. Sometimes it takes six months, eight months, nine months; meanwhile, they’re turning down everybody else’s offers, and I’ve been successful walking in nine months later, buying the property for significantly better price returns than what anybody else had offered. In other words, I’m getting a better deal than anybody else offered just because of the rapport.

Joe Fairless: Over those (let’s say) eight months, what are you doing over those eight months?

Tyler Sheff: If they’re in my local market, we’ll have a cup of coffee. Recently, I flew up to Memphis and I talked to a guy I’ve been talking to for several months and I said “Hey, I’ve really never got to tour Beale Street. I’m gonna be in town for a couple days. Can you meet me for a beer on Beale Street and kind of walk me around?” He says “Yeah, man. That’d be cool”, so that’s where we’ve been in the afternoon, walking around on Beale Street. He was giving me a tour of the history of Blues in Memphis, Tennessee. We struck up a great, rich rapport; we’ve spent maybe 30 minutes talking about the deal (or the property, so to speak). He’s not quite ready to pull the trigger yet, but we part as friends, you see? We’ve gone to a different place.

Two weeks after that he calls me and says, “Hey man, I just wanna thank you for not coming up here and trying to hump my leg over this deal. I really appreciated hanging out with you.”

Joe Fairless: [laughs] Did he use that expression? Because I like that–

Tyler Sheff: He used those exact words; I’ve been using them ever since. It just stuck in my head, it’s like “Great, I like that…”

Joe Fairless: It’s a good visual. I don’t know about a good visual, but it’s a visual.

Tyler Sheff: No, it’s a bad visual. [laughter] So yeah, it works, and I feel good about negotiations… It takes all the animosity out, because I’m genuine.

Joe Fairless: As far as ways to improve this – so that’s the approach that you take and it works, but now let’s talk about how the listeners and myself get better at this.

Tyler Sheff: Start with the why. You can’t get the answer usually the first time you ask the question; that’s been my experience. They’re gonna give you some other sort of an answer, so… Practice makes perfect. I don’t know about you, Joe – you do a lot of transactions, I’m sure you look at a lot of different deals… Anybody that’s gonna be out there actually doing deals, you’re gonna get practice all by itself, and practice is really what it comes down to. Get out there, fail… You’re gonna ask the question the wrong way, and I can’t tell you which way to ask the question. I could tell you how I do it, but this voice only translates so well… People think that I’m more like a caveman, and I should be [unintelligible [00:16:49].04]  kick your door in and steal your car.

You’re gonna have to try different approaches, but the key is if you go in with the mindset that you genuinely care about solving the seller’s problem, the only thing stopping you from doing that is the answers to those questions; I think most people reasonably will figure out after a couple of times on how to answer those questions that works best for them, I truly believe that.

Joe Fairless: A lot of times brokers get in the way…

Tyler Sheff: Yes, they do.

Joe Fairless: Any thoughts on that?

Tyler Sheff: Well, being one… Full disclosure, I’m a realtor/broker, whatever, but I’m not licensed in Florida as a broker, but I’m a listing agent as well, I list properties, and… I encourage communication, first of all. I will automatically try to befriend the agent. It’s a little easier for me being one; they treat me a little better because I’m one of them, so to speak; at least that’s how they see me. But for a person off the street, I would think — first of all, they live in scarcity, a lot of them do. They’re very afraid of losing out on the opportunity; there may be some insecurities there, whatever… A little bit of a scarcity mentality working. Knowing that, play to that. In other words, assure them that you’re focusing on everybody winning in this transaction.

And what I’ve done in transactions is I’ve actually taken the responsibility early on for paying the broker’s commission from the seller. In other words, instead of “Listen, John (the broker), I understand you have this listing… How about this, I don’t want your commission, or the seller to think that your commission may impact this deal, so let’s even the playing field; I will go ahead and cover your fee if we successfully close on this. Does that make sense?” “Yes, it does.” “Good. So now the commission’s off the table. Now, help me get this thing put together.” I’ve done a couple deals that way and they’ve worked out quite well.

Joe Fairless: That makes a lot of sense on the five to fifty units, because what’s the typical commission on average, on (say) a 50-unit that you’re buying?

Tyler Sheff: You’re looking at 4% on average.

Joe Fairless: Okay, and how much are your purchase prices about?

Tyler Sheff: We’re looking at anywhere from 300k up to maybe 3 million.

Joe Fairless: That’s a big range. On a 3 million dollar purchase, 4% is 120k, so you would be baking that into the costs to acquire the property?

Tyler Sheff: Absolutely.

Joe Fairless: In exchange, you have an ally from the seller side, and that would help you get the transaction closed?

Tyler Sheff: Absolutely, correct. And over and above that, when I’m working with my license, representing the buyer, I always offer to take my fee as a promissory note, recorded against the deed. So in other words, I represent you in the transaction, and I say “Joe, I’ll tell you what – don’t worry about my commission. I will record it as a note. Pay me 6% a year. How long are you gonna keep the property? 10 years? Okay, let’s amortize it over 10 years. That’s 200-something dollars a month, or whatever it works out to be. Let’s do that and let’s let the tenants pay men, and then you don’t have to. It doesn’t become part of the transaction. It’s just [unintelligible [00:19:51].25]”

Joe Fairless: Let’s say that your fee is $100,000. How would you structure that again?

Tyler Sheff: I would basically amortize my fee. So let’s say if your exit strategy is a ten-year hold; I would note in the mortgage maybe 5%-6% interest, and then amortize it over the term of the duration, whatever you’re gonna own the property… Maybe structure a balloon, or something like that to pay off at closing, and that keeps it clean. And then I just become a monthly expense.

Joe Fairless: I haven’t heard of that before. In that case it would be roughly $10,000 + 5%, 6% interest, whatever you do a year, and then at the end of the ten years, you’re fully paid of… Or something like that with a balloon payment after ten years where it’s not 10k, whatever the structure is.

Tyler Sheff: Right. The beauty of it is that we can structure it any way we need to, to make the deal work.

Joe Fairless: And if they don’t pay it, what happens?

Tyler Sheff: I have a second position lien recorded against the property, so I guess we can start looking at foreclosure options and things like that, but I’ve gotta say, I’ve been in the business 17 years, I’ve never had anybody not pay, knock on wood.

Joe Fairless: That is one creative way I hadn’t come across before. Anything else as it relates to asking better questions and not assuming the answers that you wanna mention in our conversation?

Tyler Sheff: I would say – and this is gonna be a tough one for most people, especially in today’s society… But in today’s society, really there’s no excuse to not be face-to-face; we’ve got things like Zoom, we’ve got Skype, we’ve got the ability to get in the car and drive across town… Try to be face-to-face whenever possible – and by that I mean even virtually face-to-face – while you’re talking to people, because I think if they can see the fact that you’re genuine, I think that says a lot to the questions that you’re asking, and I think that’s gonna result in getting better answers. That’s been my experience.

Joe Fairless: Great stuff. I appreciate these insights and the overall approach. One additional resource I recommend on this topic of not assuming the answers is Crucial Conversations. It’s a book that I have read multiple times and I recommend to people. Anyone who assumes things, basically they’re telling themselves a story, and everyone has their own story, and nothing in life means anything until we interpret the meaning that we choose to assign it, and that’s something that this book talks about, and they give some great examples… So Crucial Conversations is a book I recommend.

How can the Best Ever listeners get in touch with you, Tyler?

Tyler Sheff: The best way to reach me is through my website, Of course, for our podcast, we’re on Stitcher, iTunes, the whole nine yards.

Joe Fairless: From why you buy five to fifty units, and the benefits, and how you handle the management – you just bake it in prior to closing, 15%-18% of annual income; in reality, you’re seeing between 10%-13%. Two, how you’re working with the local owners to purchase those properties and the focus that you have, which is being focused on the seller’s needs, not your own, and caring about solving the seller’s problems, that being the exclusive focus, then everything else falls underneath that. It might take a couple conversations, it might take eight months, or it might never happen, however you’re setting yourself up for success with a higher probability of closing with that approach. I appreciate you taking that approach and giving us some specific stories, with the Beale Street example, and the whole humping your leg thing.

Thanks for being on the show, Tyler. I hope you have a best ever weekend, and we’ll talk to you soon.

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JF1168: Have Your Tenants Pay Taxes, Insurance, and Maintenance! With Dave Sobelman

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Triple net leases allow investors to be very close to passive. The three nets; taxes, maintenance, and insurance, are all paid by the tenants. You can imagine the headaches that could save the building owner! While this strategy does offer less risk, it also comes with a little less return on your money. If you enjoyed today’s episode remember to subscribe in iTunes and leave us a review!


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Dave Sobelman Background:

  • Founder & CEO of Generation Income Properties (a public net lease REIT)
  • Founder of net lease brokerage firm 3 Properties.
  • Managed more than 1,000 single-tenant net lease transactions and has been involved in about $10 billion in transactions
  • Began his tenure in commercial real estate as a Research Analyst and Associate for Grubb & Ellis Company
  • Was responsible for maintaining market data for over 134 million square feet of area properties and accurately forecasting regional trends for client assessments
  • Based in Tampa, Florida
  • Say hi to him at  
  • Best Ever Book: Shoe Dog

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Joe Fairless: Best Ever listeners, welcome to the best real estate investing advice ever show. I’m Joe Fairless, and this is the world’s longest-running daily real estate investing podcast. We only talk about the best advice ever, we don’t get into any fluff.

With us today, Dave Sobelman. How are you doing, Dave?

Dave Sobelman: I’m doing great.

Joe Fairless: Nice to have you on the show, I’m glad you’re doing great. A little bit about Dave – he is the founder and CEO of Generation Income Properties, which is a public net lease REIT. He is the founder of net lease brokerage firm 3 Properties. He’s managed more than 1,000 single-tenant net lease transactions and has been involved in about ten billion dollars in transactions. Based on Tampa, Florida. With that being said, Dave, do you wanna give the Best Ever listeners a little bit more about your background and your current focus?

Dave Sobelman: Thank you so much. When you go through my [unintelligible [00:01:54].00] I can’t believe where we’ve come. I started my career at the very bottom. I was a research analyst for a national commercial real estate brokerage firm, where I sat in a cube; no one talked to me, the cube was far away from everyone, and they just wanted me to crunch numbers. It was one day when someone came up to me – about eight months after I started – and asked me my first question in that analyst role, and that’s when I knew that people started to value my work and my opinion.
Since then, I’ve had a sole focus, strictly on triple net lease investments throughout the entire country. Like you said, I’ve done about ten billion dollars in transactions in the last 15 years, and it’s been really interesting to see how having that sole focus has been extremely accretive to not only the companies that I’ve started, but also the industry itself.

I was an anomaly back 15 years ago when I was solely focused on this one property type, because net lease properties truly just were an ancillary investment at that point. A lot of shopping center owners had these outparcel locations, like a McDonald’s or a Burger King or something like that; they didn’t really treat them as an investment – or I should say an industry – in and on itself. So when someone like me came along and said “I’m only gonna focus on these single-tenant triple net lease assets”, we kind of took the market by storm at that point.

Joe Fairless: For anyone not familiar with what you mean when you say single-tenant triple net lease, will you just quickly define that?

Dave Sobelman: The stereotypical example of a single-tenant commercial triple net lease property is your average neighborhood Walgreens drug store. Most people know what that means. There is one parcel of land, there is one building, the building was built specifically for Walgreens in this instance, there’s one lease — a lot of people don’t know that Walgreens in this case doesn’t own a lot of their real estate, they lease it from people who build these buildings for them, and the leases are very long. In their case, they’re 75 years. They have options to terminate after 25 years, but even 25 year is a long time.

Walgreens is a big public company, and they have what’s called an investment-grade credit rating, meaning that they don’t have a lot of debt and they’re a strong and sound, credit-worthy company. Putting these factors together – real estate, good credit tenants, long-term leases, and you get the makings of a good investment.

Now, why are they called triple net leases is – and this may be strange for people to hear, but the three nets are taxes, maintenance and insurance. Those three attributes of the operations of the property are the tenants’ responsibility, not the landlord.

So the landlord in essence is passive from a day-to-day operational perspective. So these triple-net leases are actually very common around the country, and a lot of people don’t know that, but you can be a (somewhat) passive landlord – I put parentheses around ‘somewhat’ because no real estate is passive altogether, but this takes away changing light bulbs and fixing toilets and so on.

Joe Fairless: Ideally, we’re all doing that, not changing light bulbs… Ideally, we all have triple net lease tenants. The perception that I have – and I know you’re gonna educate me otherwise – is that there’s not as much money in buying these types of properties, because they’re… And again, you’re gonna probably punch me in the face when I say this – it’s easier to do triple net lease, to buy them, and you’re not gonna make as much money. So what did I just say that was incorrect?

Dave Sobelman: There’s definitely a stigma on the properties that when you have lower risk, lower amount of responsibilities, that your yield is lower. In some cases it’s very much true, so I wouldn’t disagree with that at all. When you’re getting into higher risk properties, let’s say buying vacant buildings or vacant land that you have to develop, your returns will be higher, but you are taking more risk. So these are probably one of the best risk-adjusted returns that an investor can get, real estate or otherwise.

Let me quantify that for you somewhat. Let’s just continue using our Walgreens example. If you were to purchase a Walgreens drug store as a triple net lease real estate investment, your return today would probably be around six; maybe a little bit lower, maybe up to seven, and that’s a percent return. If you’re getting that 6% return, you have Walgreens as your tenant for 25 years, you get the appreciation of the building, if you have a loan you get to deduct the interest expense on that loan… Now, let’s say you want to buy a bond. A lot of people know that bonds are very conservative; bonds are based on the guarantor of that bond… So let’s say we buy a Walgreens corporate bond. Today, that bond is still guaranteed by the exact same company that’s occupying the Walgreens drug store. The term could be the exact same, 25 years, and obviously the credit of the company is the exact same as the tenant who is occupying that building. But if you were to buy that bond, you are probably getting a 3% or 3,5% return.

So you have multiple hundreds of basis points difference in buying a net lease property versus their corporate bond. Now, if you’re comparing it to higher risk real estate investments, yes, they are on the lower end of things. But from a risk-adjusted basis, they are actually tremendous investments.

Joe Fairless: With your REIT, is your — I hate to say elevator pitch, because I don’t pitch things and I know you don’t either, but your short and sweet value proposition basically that? It’s “Hey, you’re likely gonna get a better return than buying a bond, and you have a collateralized asset?”

Dave Sobelman: No, that’s not my value proposition at all, because having a public REIT – there’s a tremendous amount of disclosure and transparency. That’s one of the things I like about the REIT – just telling the public everything. One thing I like to say is that my REIT Generation Income Properties is not a new concept. I’m not the first triple net lease REIT. In fact, there are 14 other triple net lease REITs that are currently trading all on the New York Stock Exchange.

Now, each one of those REITs has their own strategy within this niche product type. Some people say “We’re strictly gonna buy retail properties” or “We’re strictly gonna buy net lease office properties, or industrial properties.” Some other REITs will say “We don’t wanna buy any credit-worthy tenants whatsoever, so we will never have a Walgreens using that example in our portfolio. We only wanna buy much higher risk credit tenants, because our returns are higher”, and then different variations on everything I just said.

Joe Fairless: Okay.

Dave Sobelman: So the difference between Generation Income Properties and the other 14 net lease REITs is that GIP focuses on the real estate. Now, let me tell you what that means. When someone goes to buy a net lease property, typically they’re looking at the credit of the tenant and how long the lease is, because they want to make sure that their investment can actually pay them income, pay the rent for as long a period as possible, and that’s great. But you are buying that Walgreens that we’re using as an example in midtown Manhattan or in Dubuque, Iowa. With all due respect to Dubuque, Iowa, there’s probably a drastic difference in the valuation of the real estate than midtown Manhattan.

So Generation Income Properties puts the real estate underwriting first, because what we wanna do is increase the value of that real estate during our ownership, and ultimately what that means is not only do we get paid this rent from these investment-grade credit tenants with long-term leases, but there’s a much higher probability of that property appreciation during our ownership, and being a public company, if you do have appreciation of your assets, then the assets or net asset value of the entire company increases, and ultimately what happens is the stock price increases along with it. So I’m treating Generation Income Properties as a growth company, much more so than just a dividend machine, which all the other net lease REITs provide. They wanna tell their shareholders “If you invest with us, we will pay you a 4% return and we’ll pay you every quarter or every month, however it is.” A lot of people like that consistency, but I also provide that same market dividend, but I’m also giving the shareholders a much higher probability of increasing the stock price by buying only in the top 20 highest density cities in the country, like New York, L.A., Atlanta, Washington DC and so on. And they’re all listed on my website, the top 20 cities.

Joe Fairless: How do you increase the value of a triple net lease property?

Dave Sobelman: Just as I stated – by buying good real estate. Because most people derive the value of a net lease property from the credit of the tenant, and the length of the lease. What ultimately happens is the price is derived based on a return, which is called a capitalization rate (cap rate). When I mentioned the 6% return from the Walgreens earlier in the conversation, that’s what people like to see. “I’m gonna get a 6% return on my money, and I’m comfortable with that.” And that’s just based solely on the income, and they’re not really looking at increasing the value of the real estate, and that’s done strictly through higher density, better demographics, tough to invest markets, and just what we call barriers to entry, and that’s what we focus on… Because history has proven that you can quantifiably increase the value of a property by buying in these poor markets.

Joe Fairless: Okay, so you’re not doing anything to the property; you’re identifying the right place to buy the property, and then based on historic data, the property will appreciate because of the area that it’s in.

Dave Sobelman: Very much so. Our very first asset was purchased in Washington DC, just North of the White House. The tenant is 7-Eleven. Not super sexy, not exciting; most people will go get their Slurpee or their hot dog or their drink from there, but they have a AA- Standard & Poor’s credit rating. It’s one of the highest credit ratings there is. The Federal Government, by comparison, is AA+, so they’re not too far off from a credit perspective. This property was a brand new construction, it was the ground floor commercial condominium of a brand new construction, residential condominium building. It’s in the middle of everything, it took them four years to build this property, just because it’s so difficult to build in Washington DC. 7-Eleven has a ten-year lease (triple net), and not many people would have the opportunity to buy this. In fact, this didn’t even go on the market because the seller contacted me directly.

Another value proposition for the REIT is just my reputation in the industry allows me opportunity or access to different properties that most people wouldn’t. So that property is a great example of buying in the middle of everything, and it’s hard to buy in Washington DC. We have properties under contract in Tampa, Florida, about to be Atlanta, Georgia… Just very core markets that typically appreciate in value much faster than secondary and tertiary markets of the country.

Joe Fairless: Other than the 20 highest density cities, what are some specific benchmarks that you look for in demographics for where you buy?

Dave Sobelman: The easy ones to look for are just income, number of people, I look at the trends as well – are the trends going up or down? And then I actually visit each property I go to, to get a feel of it. Let’s take this Atlanta property that I just mentioned – it’s occupied by SunTrust Bank, which if some of your listeners don’t know, it’s a public company, Standard & Poor’s credit rating of A, and they’re headquartered in Atlanta. So this is a prime site for them.

I actually went to the site, I lived just above another commercial condo, triple net leased to SunTrust; I rented an apartment that’s just above this building and I actually embedded myself in the community for a period of time, so I can see…

Joe Fairless: How long?

Dave Sobelman: One night, two full days.

Joe Fairless: [laughs] You made it sound like six months or a year.

Dave Sobelman: No, for sure… I still want my wife to like me.

Joe Fairless: Alright, so you spent the night there, okay.

Dave Sobelman: But seeing the property at different points of the day is really important, because a lot of people go to a property one time, they drive by it, they don’t go inside, they just see “Yes, it does exist”, and they’re comfortable from that point on.

I take a much different approach, where I like to see it during morning hours, during lunchtime traffic where people are out getting their lunches; in the evenings, after they’ve left work, what’s the nightlife looking like? And so on.

There’s lots of different ways to diligent a property from a physical perspective, and that’s something that I take very seriously.

Joe Fairless: Drill in a little bit deeper on specifics  – you said you look at the income, the number of people, trends going up and down… Can you give us some specifics as far as what income do you look at, what number, how many people – 20, 5 million, 300 thousand? And what specific trends?

Dave Sobelman: I don’t have specific numbers, because every market is different. Washington DC actually has higher density than Atlanta, Georgia, and I’m not talking about the suburbs of Atlanta either, I’m talking about Atlanta proper, downtown Atlanta. So the densities are just different. So I don’t have threshold numbers, we take up to 100 different variables into account in any one property.

Joe Fairless: Are all 100 weighted equally?

Dave Sobelman: No.

Joe Fairless: What’s weighted the most?

Dave Sobelman: Just appreciative value. So “What is the potential to appreciate the value of this site?”, that’s the most important variable. But if we’re getting into the minutiae of underwriting, then we can look at “Is the property on a corner, or is it mid-block? What’s the access to the property? Is it good or is it bad? Does the property have parking?” If it doesn’t have parking – like a lot of these dense properties, they don’t have parking at all – then how do people access this property and how do they get to this property? What can we reuse this property for? Even though I’m telling you a great story right now that we’re buying properties occupied by these tremendous companies, I’m always looking at the asset from the worst-case scenario, because what we’ve learned during the last recession is even great companies go out of business.

Kmart used to be a great company, Circuit City used to be a great company, Blockbuster was a great company… And what we learned is even though they were a great credit-worthy company, we had to start learning how to reuse their real estate. In a lot of cases, that’s happening. Blockbuster is probably the best-case scenario on that. Even though they went bankrupt and vacated all of their thousands of locations around the country, a lot of them were in great locations. Those landlords who owned those assets were able to either sell them, or completely reposition them with different tenants, maybe retrofitting them for a different use or allowing the tenant to retrofit them at their own expense for a different use.

So there’s just so many different ways to look at an asset, and you really don’t do that unless you’re spending a decent amount of time there.

Joe Fairless: Based on your experience, for a Best Ever listener who’s listening to this and thinking “Well, I like what you’re saying and I wanna get in on some triple net lease single-tenant properties”, what’s your best advice ever for them as a startup?

Dave Sobelman: Well, first of all, they’re expensive. So if you’re gonna buy a property for yourself or a small partnership, I wouldn’t recommend just throwing a few dollars together. I would recommend waiting and kind of saving those dollars until there’s a substantial amount. That substantial amount could be 2-3 million dollars.

If you wanna get into the net lease business and have some exposure in your account to net lease properties, that’s what REITs are set up for, where you can buy shares of the REIT that’s focused on the net lease properties themselves, and then you can have your exposure that way.

Typically, if someone approached me during a brokerage transaction where they wanted me to represent them to purchase an asset and they said — let’s say I have $500.000, which you and I both know the value of a dollar, we both know that that’s a tremendous amount of money, but in the scheme of a net lease investment it’s a very low dollar amount. So the quality of the asset that they would be purchasing at those low dollar amounts would not be worth the risk that they would be taking.

So I would either encourage them to put a lot of people together at $500,000 each, or to kind of spread their risk and get the diversification of a REIT that’s focused on this.

Joe Fairless: Are  you ready for the Best Ever Lightning Round?

Dave Sobelman: Let’s go!

Joe Fairless: Alright. First, a quick word from our Best Ever partners.

Break: [[00:20:54].11] to [[00:21:51].26]

Joe Fairless: Best ever book you’ve read?

Dave Sobelman: Shoe Dog, by Phil Knight. It’s essentially my life story.

Joe Fairless: Best ever deal you’ve done?

Dave Sobelman: Probably a 17-property portfolio occupied by Havertys Furniture, in 10 different states, at a value of about 55 million dollars.

Joe Fairless: And why is that the best ever deal?

Dave Sobelman: Well, number one, the scale of it. Number two, it was very early in my career, so it was very meaningful to me.

Joe Fairless: How do you make money on these deals?

Dave Sobelman: My best advice to people who truly wanna make money on net lease properties is to make sure that you hold them for generations, hence the name of my REIT, Generation Income Properties. You wanna have that sort of outlook. You will get paid during your ownership of this property – that’s what the tenant is there for, that’s what the rent is there for… But you wanna make sure that you’re holding it for a long period of time so you can make a lot of money.

Joe Fairless: What’s a mistake you made on a transaction?

Dave Sobelman: Probably early in my career – this is an asset that I still own, because it’s not sellable; I just jumped at an opportunity, what I thought to be a well-priced net lease property, and it turns out that the tenant was very poor, and they vacated the property. We got a second tenant in there, they were very poor, they vacated the property – all of that happened within a  few years of each other, and now the property’s location is what I would call tertiary market… There are so few tenants who truly wanna be in this asset. It’s really a lesson that I learned – to your point, my worst deal ever – that in real estate the actual location does matter.

Joe Fairless: Best ever way you like to give back?

Dave Sobelman: My wife and I have a family foundation called The Wellspring Fund that focuses on children, and exposing them to other children that may be a little bit different than themselves – whether it has to do with nationality, race, religion, ethnicity… We really focus our philanthropy through our family foundation.

Joe Fairless: How can the Best Ever listeners either get in touch with you or learn more about your company or REIT?

Dave Sobelman:, that’s the website for the REIT. All of our contact information is there, there’s a video about me, you can hear me talking about the REIT, and I actually personally respond to every e-mail and every phone call. Actually, one of my great pleasures is educating people about the REIT, introducing them to that… So all of the investors who are in the REIT now, they’ve all had personal interactions with me, which I very much appreciate.

Joe Fairless: Dave, thank you for being on the show and talking about your positioning within the REIT space, how everyone is looking for that angle – some only retail-focused, industrial office, some no credit-worthy tenants because they want a little bit higher risk for better returns… Your focus is on the real estate itself and the appreciation of that real estate based on the location of where it is and how it’s positioned in that particular submarket, and then all the lessons learned along the way.

Thanks for being on the show. I hope you have a best ever day, and we’ll talk to you soon.

Dave Sobelman: Thank you.

Best Ever Show Real Estate Advice from experts

JF769: Don’t Use Your Renovation Contractor for a New Development

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General contractors come in all shapes and sizes, and we mean jobs. Your typical general contractor may be skilled at renovations, but wouldn’t have a clue what to do with new construction. In this episode you will learn what to look for, enjoy!

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JF532: A Closer LOOK at Optimizing Your Mortgage and How to Save Through Leverage

We have had a previous guest explain a phenomenon that seemed too good to be true, paying down your mortgage rapidly and saving by leveraging another interest bearing loan. Today’s guest will come to shed more light on the matter and tell us exactly how it works. He claims you can save in interest payments by leveraging another debt, don’t miss this episode!

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JF429: How Technology Elevates REI to a New Level

Our Best Ever guest is revolutionizing the way flippers streamline a property rehab analysis using an app contracted through Home Depot. He has built and liquidated real estate portfolios three times including up to 30 properties at a time. He now specializes in the sale of software that produces real estate investment analysis all in house, hear the details now!

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Best Ever Show Real Estate Advice

JF365: $1,000 Credit Card Charge to Virtual Wholesale Genius!

Ready for a new market? Our Best Ever guest hints how he successfully wholesales properties…virtually! No need to be everywhere at once; he instructs how to close a deal in another city while in the comfort of your home! How to find your “boots on the ground” including additional real estate professionals in places other than your hometown, you have to hear this!



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Chris Bruce’s real estate background:



  •  Full time real estate investor who started investing in Detroit, Michigan then went to Tampa, Florida
  • Say hi to him at
  • Popular podcast called Escape the REI Newbie Zone
  • Virtual wholesaling in different markets
  • Based in Tampa, Florida


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Listen to the Episode Below (26:47)
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Best Ever Show Real Estate Advice

JF101: Build Your Buyer’s List First…Here’s Why

Today’s Best Ever Guest shares why it’s important to build your buyer’s list first and we discuss who that is applied to all areas of real estate investing.

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Andrew Massaro’s real estate background:

–        Owner of Rockstar Rehabs based in Tampa, FL

–        Been wholesaling since 2005 and averages about 4 a month since then

–        Focus is on wholesaling and is author of Quick Flips and Fast Cash a former #1 best seller in Amazon store

–        Say hi to him at

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Listen to the Episode Below (24:26)
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Best Real Estate Investing Crash Course Ever!