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Douglas Skipworth on Building Profitable Investor Relationships

Douglas Skipworth on Building Profitable Investor Relationships

Today, on The Profitable Property Management Podcast, I’m talking with Douglas Skipworth, the co-founder and Principal Broker at CrestCore Realty, a market-leading real estate firm, that manages residential investment and rental properties in Memphis, Tennessee.

Since 2001, CrestCore has helped real estate investors purchase over 1,000 properties and its management portfolio has grown to more than 2,500 residential properties in Memphis, TN.

In today’s episode, Douglas shares where most property management entrepreneurs go wrong when it comes to attracting and closing investors and the exact steps you can take to build dependable investor relationships.

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Topics covered:

  • Background leading up to today
    • How did you get started with CrestCore Realty?
    • Talk me through your first deal
    • What does your business look like today?
  • Attracting and closing investors
    • What is the reality of WHY your company attracts investors, regardless of whether it’s applicable to others?
    • What is the story CrestCore is selling, how has that story evolved over time?
    • How would like to see that brand story change in the future?
    • When it comes to attracting investors, what should more real estate entrepreneurs be talking about?
    • Walk us through what your approach to attracting investors looks like in practice.
    • How has your approach evolved over time?
    • What is your strategy when it comes to closing the deal?
  • Leveling up
    • As you scale, how do these strategies evolve?
    • What changes in the market are you paying close attention to?
  • Tying it together
    • What is one thing listeners can do this week to improve their approach to sales and marketing?

Rapid-fire Questions:

  • What type of real estate transaction or deal structure will you never do again?
  • How would you advise someone who’s starting a new business and debating whether to go solo or take on a partner?
  • Who do you learn from?
  • How do you think about legacy in business?
  • What one book has impacted you the most?
  • If you could do it all over again what advice would you have given yourself at the beginning of your career?
  • Are entrepreneurs born or bred?

Where to learn more:

Connect with Douglas at CrestCore.com, LinkedIn, or BiggerPockets and if you happen to be in Memphis, Douglas welcomes you to come and visit.


Jordan Muela: Welcome closers. Today we have another episode of the Profitable Property Management Podcast coming at you. This is season two on sales. I’m your host Jordan Muela and every week, I interview world class property management entrepreneurs and industry experts who share actionable insights to help you grow your property management empire. Whether you manager 100 or 1,000 units, this broadcast is designed to help you see the big picture and give you the tools and tactics you need to get to the next level.

Today, I’m talking with Douglas Skipworth, the co-founder and principal broker at CrestCore Realty, a market leading real estate firm that manages residential investment and rental properties in Memphis, Tennessee today and globally sometime in the near future, I’m pretty sure. We’ll see. We’ll have to find out from Douglas.

Since 2001, CrestCore has helped real estate investors purchase over a thousand properties and its management portfolio has grown to more than 2,500 residential properties in Memphis. In today’s episode, Douglas is going to share where most property managers go wrong when it comes to attracting and closing that coveted investor group. These folks that are repeat buyers. These folks that have a vision for where they want to go through real estate.

If you enjoy the show, head over to iTunes. Leave us a review. The more views that we get, the more exposure that we can receive which really just means better and better guests. Let’s go ahead and dive in.

Douglas, welcome to the show.

Douglas Skipworth: Hey Jordan, I’m so glad to be here. Thank you for having me.

Jordan Muela: Well Douglas, I just want to start off with your background because I really feel like that’s going to frame the issue of why it is that your business has been so effective at targeting investors. So walk me all the way back to your undergrad work at Vanderbilt. How did you see your career trajectory back then? Were you entrepreneurially minded at that point in your life?

Douglas Skipworth: Oh man, you’re starting way back. Yeah, my dad is a small business owner and he’s a portrait photographer so he had many studios across the southeast. I definitely have some of that. I know we’ll get to born or bred but have some of that in my blood. But no, coming out of school, I wasn’t exactly sure what my career path would look like. I didn’t have … It wasn’t etched in stone. I had a bunch of friends who knew they wanted to be a doctor or they wanted to be a lawyer right out. I did not have that luxury so I had to try a few things before I found my eventual life purpose.

Jordan Muela: Love it. So the journey that you took, that makes sense to me because when I look back at the places that you worked and the industries that you were in, the common theme that I’m seeing is a lot of size, a lot of scale, a lot of regulation, not necessarily the most entrepreneurial environment. So walk me through what you did immediately out of school, the first few jobs that you held.

Douglas Skipworth: Yeah, great. I went to work for a large commercial bank here in Memphis coming out of school in Nashville, staying in Tennessee. Because I wanted to see a lot of businesses, I wanted to understand. I knew numbers, finance accounting was the language of business so I wanted to familiarize myself with that. And then again, see some entrepreneurs in action. See some different industries, different size businesses from publicly traded companies all the way down to the mom and pops. And the bank allowed me to do that.
But I always found myself as I look back 20 plus, 25 years later, I always wanted to be on the other side of the table. I always wanted to be the one borrowing the money or growing the company. It just … I couldn’t help myself but get from the advisory role to the owner/operator role.

Jordan Muela: So as you moved through these first few roles, when did buying your own properties … Let me just cut straight to the chase here. When did you make your first deal in terms of buying a piece of real estate?

Douglas Skipworth: Yeah, with that I got a masters in accounting while I was at the bank and learned more about finance and investing. And then, started working in public accounting. Worked for EY, one of the big four accounting firms. Moved to New York City for a couple years and then had a chance to move back to Memphis to be an owner/operator working a small business, a real estate technology start up, kind of like a proprietary Zillow.
And so, as I was doing that I was learning a lot about residential real estate and I started jogging with a partner, a friend, a guy I met named Dan Butler. We moved into the same neighborhood and enjoyed exercising together. And he was buying real estate, residential property. Small apartments and small single family homes. And I was learning a lot, had that finance/accounting/investment background and so, it was at that point that I learned, hey, here’s where I could marry some industry knowledge with that desire to play in the finance accounting world. So I was able to make my first purchase on a single family home.

Jordan Muela: How did that go? Walk me through that first deal.

Douglas Skipworth: Oh man, it was awesome. I learned early … I don’t know where it came from. A lot of reading and observing, I guess, others but I knew that to succeed as a real estate investor you needed to know your values, you needed to find a lot of opportunities to look at, and then make some deals. I picked a neighborhood not far from my house that I could drive by and check out and really started trying to figure out what were market rents, what were the values for the homes, and just started looking. So once I knew those values, I just started looking for opportunities. I was looking on MLS, looking at for sale by owner, talking to a real estate agent, looking at anything online, people posting on Zillow, Craigslist, anything to find a property.
So I found one through the MLS. Made an offer on it, had a line of credit on my personal residence because that was back in the heyday that the bank gave me a line of credit because the value of my home had appreciated and there was some equity there and I was able to buy it on a line of credit, put a little rehab into it, get it rented, and then go refinance that out to get all my money back. And then rinse and repeat, if you will. That’s how I got my start which is exactly what Dan was doing on parallel tracks so we were just sharing with each other as we were doing it, encouraging each other, holding each other accountable.

Jordan Muela: All right. So you do that before CrestCore. You build up a bit of a portfolio. What was the trigger for you to decide to begin managing other people’s properties instead of just your own portfolio?

Douglas Skipworth: Yeah Jordan, Dan and I don’t throw darts at a board. We bet on sure things. Have you ever read Sun Tzu’s Art of War.

Jordan Muela: I sure have. Yeah.

Douglas Skipworth: Every battle is won before it is ever fought. Think about it.

Jordan Muela: Quoting it back to me. I love it.

Douglas Skipworth: I love that you start the show with that Gordan Gecko. That was one of my favorite movies. I hadn’t seen that in a long time.

Jordan Muela: It’s a classic.

Douglas Skipworth: But in all seriousness, I mean, Dan and I, we really do practice Warren Buffet’s two rules of investing. You know his two rules of investing?

Jordan Muela: I couldn’t quote them off the top of my head.

Douglas Skipworth: Okay. We’ll put them in the show notes but it’s rule number one is don’t lose money. Rule number two is don’t forget rule number one.

Jordan Muela: Sounds pretty foolproof.

Douglas Skipworth: Yeah, exactly. So as Dan and I were buying rental property, we were really doing that living that out, try not to lose money, try not to forget rule number one. We were investors but we had a W2 job. We both had full time jobs and we were doing our investing on the side. So we got to that point where we realized that we needed … because we were long term buy and hold investors, we knew we needed a long term property management solution. We also … So we kind of got these three things.
We knew we needed a long term property management solution. We knew we needed accountability to consistently get better in the property management. And then, thirdly, because we had our jobs and because we were growing a portfolio, we knew we needed some personnel and we needed some money to pay for that personnel. So third party management looked like that sure thing. It looked like a small experiment we could do to see if this would work. And so, we made a small bet on ourselves to build a property management company to take care of our own rentals by taking care of other people’s rentals.

Jordan Muela: And how many doors were you at at that time?

Douglas Skipworth: Man, we probably had 100ish on our … like together. Between yours, mine, and ours, Dan and I … And then, we cobbled together pretty quickly another 50ish from friends and family. So probably at 150 but we were doing it on our own. And we probably didn’t get … It was probably about 300 before we hired somebody to help us.

Jordan Muela: Got it. So would you describe yourself as having been pretty connected with the investor community at that point right out of the gate when you started CrestCore?

Douglas Skipworth: Yes. Yes and no. We were definitely not connected to the investor community when we started buying rental houses on our own but as we grew our own personal portfolio, we did get more and more connected. But we were never out marketing ourselves as providing services to other investors. We were more that kind of mutual exchange that you get from just sharing knowledge with other investors. Hey, do you have a deal for me. Maybe I’ve got a deal for you. Hey, how did you do this deal? Do you know a banker? Do you know an insurance agent? Do you know a closing attorney? Did you know a roofer? Do you know an electrician? You know, just working with others in the business, developing relationships.

Jordan Muela: Gosh, I love that. All that background to get to this. Can you describe for me what CrestCore sells? How would you articulate that?

Douglas Skipworth: That’s great. So CrestCore, on the property management side, we are providing hopefully a … What we’re shooting for is a hassle-free property management experience for both our clients, our renters, and our employees. So we’re trying to make it hassle-free for everybody. We’ve got about 600 clients, international and local, that buy property here in Memphis. About 2,500 plus units like you said.
But for us, there are a couple other offshoots off that which play into it. We might not really spend our time talking about today but it’s equally as affable on the sales and marketing side and that is our real estate brokerage which is investment property focused. So we don’t do traditional owner occupant brokerage. We do help investors buy, help investors sell, rental property. Mostly single family homes and small apartment complexes but dabble in 50-100 unit apartments if we can as well as little small commercial and then the maintenance company that takes care of all of our maintenance needs as well as some other property management companies in town.

Jordan Muela: Love it. So let’s break it down. The brokerage, is that all under … You mentioned property management, the brokerage, as well the maintenance company. Are these distinct entities? Is it all under CrestCore? Help me understand the structure.

Douglas Skipworth: Yeah, so ideally there are three different entities. Currently CrestCore Realty Property Manage … So CrestCore Realty is one entity and it’s got the brokerage and property management. And then, the maintenance company is called City Light Commercial Services and it is its own entity. At some point, brokerage and property management we would like to split. We actually have an entity called CrestCore Property Management LLC that we will graduate to but we’ve just got to put some things in place internally, accounting, personnel and such.

Jordan Muela: Got it. So in terms of the actual growth of the portfolio, is the bulk of that growth coming from the real estate transaction side of things as opposed to bringing on clients that … You know, bringing on somebody who has one single family property and is never going to buy another. What’s the profile or the makeup of your existing customers and where they came from?

Douglas Skipworth: Good question. It’s changed over time. Initially, it was word of mouth referral, friends and family of the investor. So our idea … We looked out … I mean, I love … You and I know each other and see each other at conferences and we’re big fans of LeadSimple. So I love what y’all are putting out. So one of the guys we follow is Ben White and his books and loved seeing him at PMPro and Adam.
So one of his books he talks about the five channels. You’ve had him on the show. We do the same thing. We call it three channels but they’re a little different. So we’ve always looked at it as there’s three ways to get property management clients. We can acquire a property management company. We can find new clients. Or we can grow with our existing clients.
And so we have always focused on growing with our existing clients. Haven’t acquired a property management company, haven’t spent as much time and effort trying to find new clients. We have spent all of our time and effort trying to grow with our existing client. And that is, bring somebody in who … educate, help, answer questions and walk them through how we personally went from zero units to 10 units to 20 units. Then help them go through that. And the brokerage is a key component for that to help them find deals, help them finance deals, help them partner with the right insurance company, the right closing attorney and work through that.
Now that’s not to say we don’t do that second channel which is find new clients. We are looking … We’ve done a lot more looking for new clients over the past couple years than we did initially because a lot of clients would find us. It’s gotten a little more competitive over the years and as property management has become more sophisticated. But we’ve grown with our existing clients and now, the brokerage has allowed us to find the new clients, if that makes sense.
So new clients come in … So there are websites out there like Bigger Pockets. It’s a great resource for buyers. Memphis is … I mean, we’re one of those things. Are we lucky or skilled? We would say we’re blessed to be in Memphis, Tennessee where a lot of investors want to buy property and so we get a lot of attention. Memphis gets a lot of attention. We attract a lot of inquiries because of that so we’re able to warm leads or … We kind of fish with a net instead of having to fish with a line because there’s so many fish out there.

Jordan Muela: I love it. So just to be clear. Are you describing the situation where that growth of growing with your existing clients, is that more like helping investors buy more properties or helping non-investor landlords become investors and embrace that investor mindset?

Douglas Skipworth: I would say the former of helping investors buy more property as opposed to converting an accidental landlord into a investor. We haven’t had a lot of, we have some, but the proponents of our portfolio is investors. People who want to buy rental property. Want to own one, two, five, ten properties as opposed to somebody who just got stuck with a house, someway, somehow couldn’t sell it or moving on. Yep.

Jordan Muela: So it’s really the brokerage that is drawing in these investors and then you’re working with them to grow their portfolios. Correct?

Douglas Skipworth: That is correct and then the second thing is we’re always what you alluded to earlier was we’ve built a lot of relationships in the marketplace being investors ourselves. Again with banks, with insurance agents, with closing attorneys and the like. And so they, when they have clients who express an interest in a property management service or buying a rental property or selling rental property, they send them our way. They refer that business to us. That relationship, that professional relationship has just been a goldmine for us as far as acquiring new business.

Jordan Muela: Okay, great. So how do you think that those people that are referring your business think about what you do on the brokerage side. Aside from the fact that they know, like, and trust you. How do you think that they think about the differentiating factor of CrestCore in terms of facilitating a purchase transaction as opposed to XYZ agent down the road?

Douglas Skipworth: Awesome question. So I think know, trust, and like is big. And I think the experience we have is really important because they know we’ve blazed that trail, so to speak. And we eat our own cooking and know what we’re talking about and they’re doing. But I would say, because we specialize in it and because we focus on it, we have more outlets. So for a buyer, we have more sources of leads for properties. We can find more opportunities than a regular agent can or a property management company that doesn’t help people buy.
Similarly, on the sales side, if somebody wants to sell a property, we’ve got more channels for them to sell their property. And we get it all the time and it’s because we have 600 plus clients that we get referred to help people sell their property because they know we’ve got the buyers. What was that, Willy Sutton, well why do you rob banks? Because that’s where the money is. Well, why don’t you send them to CrestCore because that’s where the buyers are. That’s where the investors are. That’s why they’re going to refer them to us.

Jordan Muela: Yeah, okay. I like it. So one of the reasons that I wanted to have you on this show was that I feel like there’s some situations where you get a piece of advice and you feel like maybe it’s not necessarily applicable. And in some ways, when I look at what you’ve done, how do you replicate a decade’s worth of actually being an investor in the market. You can’t. You can’t do that overnight. But the point is, or the principle is, that you are attracting more of what you are like and you made that decision early on. It sounds like maybe it wasn’t necessarily strategic. Early on, you just wanted to own some real estate and to experience that journey of wealthy creation through real estate. But the by-product of you living that was that you were able to attract other people who wanted to be in that same place.
So as a long game principle, that absolutely is something that people can reorient around. In a short term game, that’s not necessarily something that you can clone overnight. So thinking about the positioning of where you’re at in the market, you and I know that various property management companies view some or multiple parts of the business as being loss leaders, right? In the extreme example, property management is just a loss leader for maintenance, title, brokerage, whatever it may be.
If you were to look at the deals and the transactions that you were doing, let’s say that you were going sideways on the personal investing that you had been doing or even on the brokerage side of things. Do you think that that would have still justified what you were doing from a lead gen strategy or do you view that as really being core and the property management revenue as being additive? How do you think about the constituent parts of the business and what they contribute to your overall goals?

Douglas Skipworth: We definitely say that property management is our core business. So goes property management, so goes the whole enterprise. Brokerage can be doing great, helping people buy all day long or helping people sell if they need to. But if property management is sucking wind, we’re going to be in trouble. It’s the same with maintenance. On the flip side, if the property management company is executing well and doing the things it should be then it’s just the rising tide that lifts all boats. It’s the one that we orient around for sure.

Jordan Muela: Yeah, that makes sense. Really, what I want to explore with you, Douglas, is the relationship between the investing side of the business and property management. Because when we think about what most property management companies are selling, it really tends to be a stasis driven sort of thing. I have this asset and I don’t want anything bad to happen to it. I want it to grow but honestly, that’s largely in terms of the consumer perception a market condition based scenario. But I definitely want my downside protection there and it’s implicit in the word. Property management by nature the level of excitement or proactive effort that is going to be granted to just the name itself is low whereas if we’re flipping, we’re doing deals. That feels like more of a proactive sort of a thing.
So the challenge that I see is that so many property managers feel commodified when they talk to people. And the first question is well, what’s your price? And yet, there’s also that understanding of how they’re contributing to being commodified by virtue of not selling a better story. If the story is simply, I will maintain what you have and make sure that nothing bad happens to it, in many ways, it’s not a compelling story as compared to long term wealth creation through real estate.
In your opinion, why is it that more property management companies don’t sell and lean into that story in light of the fact that you have and you’ve seen the power that comes from it?

Douglas Skipworth: Oh man, that’s a great question. And it’s hard to speak, obviously, for other people, especially when you’ve got your mindset. I mean it’s easy to get caught up in the day to day as far as the property management business. It’s a hard business. You manage 200 units and just one thing goes wrong or just 1% of things go wrong, that’s still one issue you’re dealing with that could be a big deal. So it’s a lot of putting out fires and I think you get limited on your mindset.
If you’re not participating in NARPM or PMPro, or listening to your podcast or listening to some of the other stuff that’s out there or reading it, it can be very lonely and thinking that you’re … a lot of times is you hear somebody who joins something like NARPM to say, oh I found my people. I found somebody who speaks my language, who understands what I go through all day, every day. So if you’re out there alone, you maybe can get shortsighted and lose sight of the bigger picture of what this is.

Jordan Muela: Okay, that’s fair. So let’s explore that. Part of what I hear you saying is that it’s circumstantial and maybe if you had started a property management business first and not had the experience of investing, that maybe you’re saying that you might have gotten stuck there and not realized the power of going deep on that investor side. Is that kind of what I’m hearing?

Douglas Skipworth: I think that is one possibility for sure and something that I feel I’ve seen and witnessed locally in our marketplace here for sure. Go ahead.

Jordan Muela: Let’s just talk more about the power of that story. Ultimately, businesses are brands, they’re selling stories that consumers believe that they can participate in as a result of working with the brand. You’re selling wealth creation through real estate. Somebody else is selling the opportunity to basically just maintain what they have. When we say that that is what you are selling, what does that look like for you. Put legs on that. Is that content? Is that just mindset? Is that your ability to facilitate a phone call and speak the investor’s language pro forma? Walk me through what’s bound up in that that allows you to actually accomplish that.

Douglas Skipworth: That’s a really good question because that is what we feel the core of who we are. And part of it’s in our core values which integrity, personal responsibility, partnership, service, growth, and long term perspective. And so it’s kind of tied up into some of that’s in that investor mindset of partnerships, long term perspective, growth. And so we’re able to bring that to the table in those conversations. So yes, we kind of go back to that … A lot of times we go back to that Peter Drucker question of who’s your customer and what do they need? So who’s our customer and what do they need? And so, we again, try and revolve around that. And our customers are our investors and yes, they need their property managed but they need education. They need great service.
So that looks like continually improving our operations and customer service for them. I mean, we could spend a whole episode just talking about strategies and tactics around property management, the business, of running the business. But hen also, it’s a lot, as you mentioned, content Alex Osenenko over at FourandHalf, who you know well. He’s got a great framework that we borrowed for about where it’s content, reputation, and closing. So on the sales and marketing side. We’re trying to do all kinds of stuff to improve our reputation and generate content which makes the closings easier.
And so that … I know we’ve talked a little about this in the past but it’s anything from investor education with blog and videos, radio shows, investor events, attending conferences, trying to do speaking engagement, trying to participate in things like this so that then, that enhances our reputation as thought leaders in the industry which allows us to create content. And it just becomes that virtuous cycle that feeds each other and creates real value for our clients. Because at the end of the day, it’s again, who are our clients? What do they want? We’re trying to create stuff that they want.

Jordan Muela: Now, when you do that content creation, do you think of that as being more of a lead gen activity or do you think of that more of being a nurturing activity for existing customers to get them to that next step of making another purchase?

Douglas Skipworth: Oh man, initially we thought of it as a nurturing but we’ve realized it has a lot of lead gen benefits.

Jordan Muela: Got it.

Douglas Skipworth: But initially, it was how do we grow our existing … How do we grow with our existing clients? And how do we help them? What do they need? Education. What do they need? Comradery. What do they need? To know they’re not alone. To know what’s ahead. To know somebody’s been there and seen it and done it. And again, as we started doing that we realized wow, that’s creating some leads and a good way … Let’s be more intentional about that and we could create even more leads. As we’ve moved into that finding new clients as well as helping the existing clients grow.

Jordan Muela: All right. So, let’s talk about some types of content just to get into the weeds a minute for some of this stuff. I’m looking at your blog right now. Five Tips for First Time Landlords. Real Estate Investor Events and Education Podcasts. I believe that’s when you were on Alex’s podcast. Memphis vs. Las Vegas for Investment Property. Walk me … So these are just some random headlines of things you’ve produced in the past. What are specific types of content and what’s really worked well for you in terms of nurturing your existing clients and getting them motivated to make another purchase with you?

Douglas Skipworth: Yeah, so one that’s super fresh on my mind where we’re combining two, we did … as we’ve gone through this process journey together, we’re always trying to take nuggets and organize thoughts. And so we created some content years ago for ourselves but for our clients. To do lunch and learns, and boot camp stuff for locals. And we created just different little segments. Here’s the three ways appraisers appraise rental property, income approach, cost approach, sales comp approach. And we did a little section on that.
And then we did something on, here are the different ways to finance it through traditional financing or through a commercial bank or through a hard money lender or a private lender or seller financing. And we did these little segments. And we would teach those. Once we taught them, we packaged them up. Then we did some blog stuff on it and put it on our website. And now, the leader of our real estate brokerage, Dean Harris, runs … He has a local radio show. So he followed the NARPM model of getting sponsors, some of our closing attorneys, real estate, insurance agents, and now there’s to underwrite the show so it’s paid for that way and then he hosts the show. And then we get on and talk about these concepts. So I had the privilege to be on the show recently and got to go on and talk about, here are the three ways that an appraiser is going to look at a rental property to create an appraisal.
So we’re repackaging that. Putting it out there in different forms whether it’s video, whether it’s text, whether it’s classroom. To benefit our existing investors as well as to create content that a new investor will come in and say, “Oh, I’ve always wondered how appraisers are going to come up with my appraisal.” Or, “I’ve always wondered about the different ways to finance.” Or, “Okay, this makes sense. This answers my question.” Or, “This skims the surface enough that now I want to ask some more questions and they can walk me through this.”

Jordan Muela: Okay, so here’s what I like about what you’re describing. You’re forcing yourself to develop a stable of well thought through content. We both know that a one time blog post can feel very transactional, right?

Douglas Skipworth: Yep.

Jordan Muela: If the medium is a blog post, it’s easy to make it underwhelming just to check off a box. If the medium is an in person investor event, we’ve just raised the bar. You’re looking these people eyeball to eyeball and if you’re talking low value added nonsense it’s going to be awkward. So you use the medium of in person and then you took these various silos. So you compartmentalized self-contained pieces of value. You’ve given us a couple of different examples and when you went deep on that topically, it then created the opportunity for you to flesh that out and repackage it on other mediums whether that be a blog post on somebody else’s site, like what you’ve done with Fink Realty, or on the radio show, et cetera.
All of this ultimately though is really stemming from the fact that you’ve actually done it and you have first hand experience. And the moral conviction that you’re able to speak with is obviously going to be a lot more practical than somebody that’s learning this stuff from scratch. I love that framework. Walk me a little bit more through the radio show. How did that come about? What did that look like? Can you actually … can you prove any of this stuff works? I always love coming back to that, right? I mean, talk to me about the degree to which this is a faith-based proposition. Because at the end of the day, values are basically a faith-based proposition. It’s what you personally decided is important to you. And if it’s really an actual meaningful value, to some degree, it’s going to be divorced from any kind of demonstrable short term ROI.
So with content specifically, do you feel like you can … Are you doing analytics to track conversion, et cetera? Or is it more just a discipline that you’ve decided to commit to stemming from your values and how has radio worked for you in relation to that?

Douglas Skipworth: Yeah, and this time it’s the latter. It isn’t … We haven’t gotten to the point that we can quantify and run the analytics that we want to. I think that’s part of how we’re evolving over time from where we used to be, word of mouth, willpower, personality. We were going to get this and grow this business by our just strong desire. And now we’re trying to make it consistent. Make it process oriented and make it scalable.
And part of that is quantifying it and running the analytics around it. But to say that with the radio specifically as well as the other content, the radio again, we don’t account … and producing stuff ourselves … we don’t really account for our time. But we do account for the physical money out so with the radio show where we have to pay for radio time, as long as we get the sponsors to cover the cost, then it’s an investment of time we’re making but it’s creating content. It builds that reputation and it creates the content. It’s something we lead with as much as we can as a differentiator in the marketplace. We’ll say, “We might not be the very best but we are the most knowledgeable. We’ve got a radio show. Here’s some episodes that you might find interesting.” And we just lead with that as much as we can.

Jordan Muela: So it really goes back to that micro influence. When you go to a company’s website, within the first three seconds, you’ve made a lot of strong judgments that everything after that is being interpreted through. So if you roll up to an investor and you inform them that hey, guess what. I have a blog. Well, so what. Now on the other end of the extreme, I’ve got a book. And it’s a real book and it was published by a legit publishing house, New York Times bestseller. Somewhere in that spectrum, regardless of the content, the context radically informs what we choose to believe about that person and how it colors everything that happens afterward.
The other thing I like about content, and you could speak to this, is the discipline that it forces. For me, content is an extension of my values insomuch as I believe in serving, educating, and improving myself as being necessary to do that. So creating the content walks me through the exercise of learning and articulating myself and that is what I find to be the most powerful virtuous circle, right? It prevents mental laziness. It prevents an entitled mindset because you’re always having to get better to sharpen your blade. Do you feel like that as you’ve done more content creation, it’s sharpened your ability to articulate your value prop in a more explicitly focused sales conversation meaning moving from the video that you shot and getting back to having a sales conversation, do you feel there’s carryover in terms of the value creation?

Douglas Skipworth: No doubt. Yeah, not only in the sense does it give more succinct talking points instead of some rambling, kind of the framework. But if you’ve really been thoughtful about it and it’s really true, it’s a real benefit. Who was it? I think it was maybe when you had Victor Antonio on here and he was talking about bringing that market knowledge and teaching them something. And teaching the prospect. And so, you’re able to teach them something that they don’t know.
Because right now, and we talked a lot about this about PMPro, the consumer knows a lot. Your buyer knows a lot so it’s hard to … You can’t just regurgitate. You’ve got to be able to present new ideas. Things they haven’t thought about, things that you’ve learned through experience which anybody who’s been in the property management business for a year has learned more than most investor’s will ever know just by being in the trenches. And to share that experience, to have some talking points, to kind of tell, “Have you thought of this?” And that’s a lot … I know we’re not talking about closing per se but that’s a lot of how we get warm leads to the closing table and get them over the hump is through asking them questions and then sharing with them some of our horror stories. Or, oh we learned this. You want to avoid doing that. Or have you thought about this. This is a lesson learned the hard way. And just unpacking some of that. And again, some of that framework, the content gives us to talk through a lot of those points.

Jordan Muela: Love it. Totally makes sense to me. The last thing I wanted to ask you about this before we head to the rapid fire section of the interview is when you think about wealth creation through real estate, that story that you’re selling that’s been really effective for you to grow your business, where do you see future facing innovation and I specifically want to ask you about syndicating deals. Have you or have you ever considered syndicating deals say in the multi-family space and allowing your current customers to have the opportunity to have fractional ownership in some kind of a deal along those lines?

Douglas Skipworth: Yes, we’ve thought about it. Have never done it. Have a couple of investor clients who kind of do something like that but we want to be so buttoned up operationally before we go that route. And we’re getting closer and we’re excited about that as a possibility. And that’s one of the reasons we just so many opportunities to add value with that knowledge and the continually trying to sharpen the sword, like you said, continually personal development and learn that the sky’s the limit as far as what you want to make of it.

Jordan Muela: Are you doing any deal flow right now? Do you activity put deals in front of your existing stable of owners?

Douglas Skipworth: We do from the standpoint of our brokerage side looking for opportunities and then they know who is a red hot buyer or an active buyer or has money or look at a good deal. So they’re constantly, the brokerage side’s, constantly putting deals out there for our clients.

Jordan Muela: So the brokerage is really integrated with the management company in that regard.

Douglas Skipworth: 100%. Yes, absolutely.

Jordan Muela: Love that. I think that’s key. All right, well let’s move to the rapid fire section of the interview. I’m just going to ask questions that hopefully you’ve got a guttural response to. And the first question is what type of real estate transaction or deal structure will you never do again?

Douglas Skipworth: That’s a good question. Buying a property at foreclosure that we don’t have any experience in. We bought a commercial building at foreclosure. We had a ton of experience buying residential property at foreclosure and had no problem. Bought a commercial building at foreclosure. Didn’t really know what we were doing. Four years later we still have that commercial building and are trying to figure out what the heck we’re doing with it.

Jordan Muela: Okay, so it wasn’t so much the foreclosures but just the fact that you had less experience with commercial.

Douglas Skipworth: And getting out of your circle of competence or your area of expertise. That’s right. It was a small experiment but thankfully it wasn’t a huge bet. So, anyway.

Jordan Muela: Second question. How would you advise someone who is thinking about starting a property management business and debating whether or not to go solo or to take on a business partner?

Douglas Skipworth: Man, I couldn’t walk through life without a business partner personally but I think it’s kind of who you are. If you need that accountability, you need to share in the successes, you want somebody to celebrate with, you want somebody to commiserate with. You want somebody to shore up your weaknesses, somebody who you can maximize your strengths with, then that’s a great person … then you’re a great candidate for a partner. Finding a partner’s a harder thing but you might be a candidate for looking for a partnership if some of those things ring true for you.

Jordan Muela: Have you had any partner experiences that went south?

Douglas Skipworth: I’ve definitely had some partnership experiences that were more challenging than my current business partner, Dan Butler. He and I have had some relationships that have not been that great personally and then outside of our partnership, we’ve both had some things again. More challenging. Nothing disastrous. Nothing to scare us away from ever being a partner. You know, those people who have been …

Jordan Muela: Burned.

Douglas Skipworth: Been burned. And hey, I’m never going to date again, that kind of thing. So no, we love our partnership.

Jordan Muela: Love it. It’s been a positive experience for me as well. It’s definitely additive.
Who do you learn from currently?

Douglas Skipworth: Oh my goodness. I try and learn all day, every day from whomever. I read a ton. I love reading business how-tos and biographies. Especially business autobiographies. I love that. Love listening to podcasts whether it’s something like your show or things like How I Built This or Masters of Scale. Good shows out there. And then, learn from friends and colleagues. We’re part of a group called This Stitch which is like EO or some of these other. It’s a peer network. I learn a ton from those guys because they’re battling the same things we’re doing in different industries but same personnel issues, same client issues, same operational issues, same financing issues. It’s a good group to learn from. Learning all the time.

Jordan Muela: I like that. So you’re exposing yourself to learning well outside the realm of property management.

Douglas Skipworth: Yes. Absolutely.

Jordan Muela: How do you think about legacy in business, Douglas?

Douglas Skipworth: Oh man. I’m only 44, man. I hope to be doing this for 56 more years. I hope to be doing it till I’m 100 so I’ve got a long time to think about that. I think about it as just showing up and doing what you’re called to do day in, day out and leaving things better than you found them, whatever that will look like. Serving your clients well, serving your employees well, colleagues well.

Jordan Muela: I like it. I threw you a curve ball there, man.

Douglas Skipworth: You did, you did.

Jordan Muela: What one book has impacted you the most?

Douglas Skipworth: Oh man, outside the Bible. Man, I would probably say a good one for this group is Built to Last by Jim Collins. It was kind of a precursor to Good to Great but I just know a lot … It’s kind of foundational for how we’re building our business. Kind of talking about a legacy. You know, built to last, built around purpose and change. Purpose and change both at the same time.

Jordan Muela: Playing the long game. Yeah. That’s classic.
If you could do it all over again, what advice would you have given yourself at the beginning of your real estate career?

Douglas Skipworth: Oh man, so both on the … And this whole business career, even though we valued relationships so much, I don’t think you could overemphasize it.

Jordan Muela: I totally agree.

Douglas Skipworth: In the sense of the right hires, the right partners, like we just talked about. I mean, just surrounding yourself with the right people and being way more intentional about that. And not settling. Holding out and doing, even if it means doing more yourself until you’ve found the right, quote, partners, business partners, vendors suppliers, customers, clients, for sure.

Jordan Muela: Man, that is great. So what I’ve been thinking about recently is relationship versus productivity. And my experience has been that in business, a lot of times we view these two things as competing priorities. What we really want it productivity and we’re willing to embrace relationship as a proxy or medium for getting back to productivity. Culture for example. It’s considered soft skills. And some ways, it can be viewed as a secondary background sort of thing or a means to an end as opposed to the thing. And my view currently is that relationships in life and in business really is the main thing and productivity is really an extension and a byproduct of that as opposed to the other way around. What do you think?

Douglas Skipworth: Yep, 100%.

Jordan Muela: A lot of possibility wound up in getting the relationship piece right. Final question of the interview, are entrepreneurs born or bred?

Douglas Skipworth: Oh man, I’ve been waiting for this. Yes. So I’m going to answer like everybody else who’s been on the show. Both, but I’m going to give you a twist.

Jordan Muela: Flesh that out for me.

Douglas Skipworth: Here’s the twist. I view it like the parable of the talents from the New Testament. So in that parable, a master gives his servents, three different servents, talents. He gives one, one talent. One, two talents. And one, five talents. And then, he comes back. Two of the servents have maximized the talent and one has essentially squandered it. And so I kind of view it when you think of entrepreneurship, I think we’re all given a measure of entrepreneurship and then there’s the born part. And then it’s kind of the bred part that it’s up to us to maximize it or to live up to our potential. So that personal development we’re talking about.
Maybe looking at it in a different analogy is maybe like a professional athlete. Are you drafted in the first round? Are you drafted in the late rounds? And what do you make of that? Do you become an all star or hall of famer? Growing where you’re planted. I think it’s both but I think a lot of it depends on you nurturing your … what I would call your God given abilities.

Jordan Muela: Okay, I’m digging this. I’m hearing where you’re coming from on that there’s no doubt about it. So you’ll see folks that have tremendous, talent, quote/unquote, and squander it, right? And what’s interesting about the MENSA club or organization or geniuses and it very much does not correlate with life achievement, et cetera. And then, you’ve got folks that have really hard circumstances and have actually even just achieving a baseline modicum of success was a huge miracle of a victory for them in light of the circumstances that they were up against.
So I think that’s a pretty fair answer. I would give that two thumbs up for being a good answer and not a cop out. I appreciate you parsing the nuance.

Douglas Skipworth: Yeah, for sure.

Jordan Muela: So Douglas, if folks want to follow a little bit more about CrestCore. And specifically, if folks want to have the experience of an investor as it relates to experiencing your brand, what’s the best way to do that? Do you have a newsletter? Do you have an email list? How can they get in touch and follow what you’re up to?

Douglas Skipworth: Yeah, so part of where we are is trying to make this more than just cult of personality and trying to … so a lot will change over the next six months, 12 months to 24 months. But right now, it’s the standard places. Crestcore.com, LinkedIn, Facebook, Bigger Pockets. Anybody is welcome to come to Memphis to visit. We’re always attending the conferences whether it’s the PMPros or the NARPMs, we love to connect at those events as well. But connect with us. We love sharing with each other. There’s nothing better than to learn and learn from one another. So we’re big proponents of that.

Jordan Muela: Love it. Follow this guy online. Incredibly sharp and they just set a great standard for the trajectory of what’s possible in the industry by nailing this story. Get the story right, all things good will come from it. Don’t fight against the tide. That’s what I appreciate about what you’ve been doing with CrestCore. Thanks for coming on the show Let’s stay in touch, Douglas.

Douglas Skipworth: Yep, sounds great. Thanks Jordan.