Show Summary

Veteran real estate investors know how to plan for different real estate cycles, and win during both up and down markets. It’s often a change in strategy that allows you to not only survive, but thrive during different real estate cycles. Joe Calloway joins us today to share his knowledge and experiences of investing in real estate during different cycles. If you’re building a business that can stand the test of time, you need to understand the information that Joe shares today…don’t miss this FlipNerd Expert Interview!

Highlights of this show

  • Meet Joe Calloway, successful Pittsburgh based real estate investor.
  • Learn as Joe shares his experiences and knowledge on how to build a successful real estate investing business that thrives in both good and bad markets.
  • Join the conversation on giving back to your community, and learn how Joe and his team are making a difference in Pittsburgh.

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Listen to the Audio Version of this Episode

FlipNerd Show Transcript:

Mike: Hey, everyone. It’s Mike Hambright with Welcome back for another Expert Interview show where I interview guests from across the real estate investing industry to help you learn and grow and hopefully inspire you.
One more plug for the upcoming REI Power Summit, which is going to be one of the largest online real estate investing events ever. It’s 100% virtual. We have over 50 great speakers. You’ve heard me say this a bunch of times if you watch this show. So check out REI Power It’s coming up real soon by the time you’re hearing this.
For today’s show, I’m excited to have Joe Calloway with us. He’s a Pittsburgh-based investor that is really focused on revitalizing the very city that he grew up in in some parts of town that a lot of investors just stay away from. So he’s gone from purchasing his first house, really just getting started not that many years ago to being one of the largest property owners in Pittsburgh with over 350 rental units. Joe really has an incredible story that he’s going to share with us here today and I’m excited that he’s here.
He has a long-term strategy. What we were talking about before we started the show is how you need to ride out different markets. Right now we’re in a hotter market than it has been in the past. It really takes having been through multiple cycles to really have the wisdom and know how to play those cycles. It’s not that you stop investing when the cycle changes or when the market changes. You just find a way to do things differently and try to anticipate your next step. That’s how you stay in this game for a long time and really build some wealth.
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We’d also like to thank Specialized IRA Services, National Real Estate Insurance Group and
Please note the views and opinions expressed by the individuals in this program do not necessarily reflect those of or any of its partners, advertisers or affiliates. Please consult professionals before making any investment or tax decisions, as real estate investing can be risky.
Hey, Joe, welcome to the show.
Joe: Hey. Thanks for having me.
Mike: Yeah. Glad you’re going to be here. Not that you’re going to be here. You are here.
Joe: In the flesh.
Mike: Thank you for being here. I’m excited to talk about this topic today. I told you literally just a little bit ago before we started I was on the phone with somebody that was questioning whether somebody that I know that wants to get started in investing that was kind of questioning should they even get started right now because the market’s too hot and it’s impossible to make money. I said some of the same things you’re going to teach us today. You just do things differently. Like in some markets, you may hold more. In some markets, you may focus on wholesaling more. Some markets you may just hoard houses because you want to rehab them and you know the market is about to turn and you can make a lot of money.
It’s interesting to me how . . . I’ve only been an investor for seven or eight years myself, but having been through a down and an up cycle now, I see some of the older sage folks that have been around for a long time and how they’re playing the market or how they’re sitting on the sidelines, kind of ebbing and flowing with market changes. That’s kind of the sign of how to be in this business for a long time, right?
Joe: Definitely. I’ve been in it since the early 2000s. I was a young man in the Navy trying to learn the game. I went through an up cycle, a down cycle and another up cycle. Frankly, I’m preparing for the next down cycle because that’s the best time to make your money in this industry, buy low, sell high. However, most investors are looking to get into the market when they read in “Parade” Magazine or some other nationally publicized periodical that real estate is hot. If “Time” Magazine is telling you that real estate is hot, you’re probably about a few years too late.
Mike: It’s true. The great thing is in a down market, and this is why we did so well in the market from 2008 to 2011, everybody that we were talking to, people that were selling houses to us, you saw it on their face. They’re hearing on the news how bad the market is and they were just dumping their houses. They’re like, “Oh man, I hear how bad it is. It just keeps getting worse.” We were like, “Yeah, if the media says it’s real bad out there, it must be.” To be counter-cyclical is a good thing.
Joe: Yeah. I think even from a smaller perspective when you’re buying in the hottest neighborhood in Pittsburgh, East Liberty is all the craze right now, and it was in “Parade” Magazine. If that’s not a publication in your Sunday newspaper, it’s like the same one they interview Garth Brooks. “Garth Brooks is breaking up with Trish Yearwood and by the way, East Liberty is hot.” Like, don’t buy there. It’s too late. So many people are flooding to that side of the city.
I’m on the other side buying much closer to city center and it’s just because I know these neighborhoods are positioned not now but in a couple years to come up. So I’m buying for a fraction of what people are buying across the city. So even on a smaller level, then you’re looking at the cycles that are happening in the bigger picture and you’ve got to be very careful when things are heating up if you’re going to jump into this game and start pulling triggers.
Mike: Absolutely. Joe, before we talk about this too much, tell us your background. You’ve got a great story and I want you to share it with everybody.
Joe: Yeah. I started investing . . . I was actually overseas. I got a reenlistment bonus around the September 11th timeframe. I was in the Navy overseas. I reenlisted. They were offering some pretty nice bonuses for an enlisted military man at that point in the Navy. I took about $20,000. I had a family member who wanted to buy a house in Missouri. I had never been to Missouri. To a 20-year-old kid with $20,000 in his pocket who came from humble beginnings, that $20,000 was more money than I could ever imagine having, let alone being able to drop it all on an investment property.
So, I did that. It turned out to be very bad. The family member was not scrupulous and did not play fair. But, luckily, I got my money back. It sparked a button to say, “Hey, if I’m going to do this, I need to educate myself.” I started reading a lot of books. At this time, the market was extremely hot, 2004-ish there were tons of courses and content out there. I attended them, learned them, educated myself and I took that money and jumped right back in.
At this point, I came back to the states in Pittsburgh and I bought the house across the street from my mom’s house where I grew up and I fixed that with my own hands, learning how to do it, asking buddies for help and bought the next one and the next one and eventually built a smaller portfolio of about 30 units and put myself back in school through the GI Bill, got an MBA.
At that point, I swore off working for the man ever again. I was an entrepreneur. But then a baby was on the way. It sounds real good when the man offers you about $65,000 a year, you have a baby on the way. As you know, flipping houses early on isn’t always as fancy as it seems. So I took a job in commercial real estate. It was one of the most enlightening portions of my career as far as learning how the big boys play and how they analyze markets and what they do. I learned a lot from some of my mentors to this day who are in commercial real estate.
So what I did is I ended up leaving that company. I took all the strategies that they used in commercial real estate and I applied them to residential real estate, raising capital, watching market cycles go up and down, how you manage a portfolio, economies of scale, the bigger strategies work great doing these smaller investments, but the difference was I was able to compete in the housing market. But when I’m going for a multimillion-dollar shopping center, the big boys were pushing me out of the way.
Mike: Right. There are a lot of great lessons you can learn from the institutional side and applying that to the residential side. A lot of residential investors, not to take and potshots at anybody, but they’re just not as sophisticated. They don’t really think about it as much like a business as the commercial guys do, especially if you’re trying to raise capital and things like that, right?
Joe: Yeah. But if you can apply those lessons, you can really, really make an impact. That’s what we did. We quickly grew. After I got out of that over the next five years, that’s when we became the number one home buyer by transaction in Pittsburgh for two years’ running. We buy a significant portion and we have a very nice portfolio.
We have some institutional investors who give us capital, which is pretty rare. We buy houses, like institutional investors aren’t calling the signs on telephone poles. When they understand what we do is extremely profitable, they really like it.
Mike: Yeah. Well, Joe, talk a little bit about the fact that you’re revitalizing the area you grew up. I know that happens. I live in an area 1,000 miles from where I grew up and it’s never really struck me to go back and kind of give back. That sounds bad that I don’t want to give back to the community I grew up in. That’s a wonderful thing and it just hasn’t been part of my core investing business and I think it’s an awesome thing. I really want to hear more about why you do that and what that means to you, I guess.
Joe: The office that we’re sitting in, I grew up about a mile away from here. I grew up in an area called Knoxville or Mt. Oliver in the Pittsburgh area. It’s still a depressed area, but we’re working our way that direction, pushing the success that we brought to this area called Allentown. One of the things that I always want to do is bring something back to my community. Growing up and not having things and understanding what it’s like to not have a lunch or not have these things, you see these kids and you relate to them, “I have it now.”
I’m doing pretty good for myself. What do you do after a certain threshold? I’m never going to be the guy with a Lamborghini my garage. That’s a depreciating asset that I never want to be a part of. So what do you do? There’s nothing more fulfilling. I don’t care if someone gives you the keys to a Lamborghini. There’s nothing more fulfilling than buying turkeys for multiple hundreds of people on Thanksgiving in the community you were raised in, the same turkeys that were probably given to my mother when we were at a small apartment building.
So, it gives a great . . . it’s a selfish . . . giving is selfish. If you want a high, go out there and make a difference in someone’s life. The other side . . . let’s talk about the profitable side of giving, most of the positive press we get is not because we’re a real estate developer. As you know, real estate developers are not usually looked at nicely in the press. We do a good job as a real estate developer and we’re responsible and we do a good job. We’re extremely profitable. But we also do a lot of good stuff for the community. So the community backs us just as well as our investors back us and, therefore, the press likes us. Hey, that’s not a bad commercial when someone’s saying, “Hey, Joe, you aren’t just a greedy real estate developer. You’re a good real estate developer with a higher purpose.”
Mike: Yeah. We do a lot to give back in other ways, I guess, charitably. My wife is very active. But recently we were involved with a Habitat for Humanity-type thing. It was a different organization. It was kind of Homes for Heroes, giving a house to a veteran.
Actually, I don’t do work in my own houses at all. But I was out with a paintbrush. My wife and my son were out there. There was just something about it that just felt really good to do something for somebody else that is the type of physical activity that I don’t even do on my own home. But it just felt good to just do that. I commend you for that. That’s awesome.
Joe: Yeah. I’m slapping the boots back on this weekend to do a community cleanup with a bunch of University of Pittsburgh students that are doing their community service element of their grade. So we’re getting 80 of them up here and I’m going to lead a team of students and hopefully teach them how to work hard.
Mike: Yeah. That’s awesome. Well, let’s talk a little bit about market cycles and maybe just share some lessons of how you look at things and what you do and maybe try to educate us in the process.
Joe: I think if you’re an investor . . . here’s a question I’m sure you get all the time. What are you? A flipper, a renter, a double flip-back wholesaler or whatever the popular trend is?
I love when that gets asked to me. I used to be uncomfortable. Now I love it and I go, “The last one, I don’t even know what that is. But what I am is an investor.” If I can buy a cow low and sell a cow high, I’m going to be a cow investor. I think when people ask me that question, I’ve been a buy, hold, rent for the last three years. Now I’m selling a lot of that portfolio off because now we’re in a better market for that.
So now people are rushing to flip. But what are they doing? Now they’re buying high and selling higher. But I bought low, waited two years and now I’m going to sell high. Just following these cycles and doing what the crowd is not doing makes you multiple times more money. So you follow these cycles. They’re not projectable if you’re trying to time the market day by day in the stock market.
But in the real estate market, we know since longer than you and I have been alive, every seven years it goes up or down plus or minus two. Sometimes it extends. Sometimes it contracts. But for the most part, you can follow these indicators and they can tell you that you should be either buying and holding or flipping or wholesaling. You should be doing that in a time that allows you to make the most profit, not when everyone else is doing it.
Mike: Yeah. And we were talking a little bit beforehand about a lot of the . . . I guess maybe give some advice to the wholesaler-type folks that are out there. There are a lot of wholesalers. I’m not knocking wholesalers. I’ve got some great friends that are big time wholesalers. But you can never stop buying.
Joe: No.
Mike: If you’re not holding, you’re not building wealth and so you can never stop working. It’s this hamster wheel of you’ve got to keep doing the same thing every day, which is how a lot of people start. But maybe talk how people can transition into being more strategic from just wholesaling if that’s what they’re doing or even just rehabbing if they’re just straight rehabbing everything.
Joe: Yeah. I always say you’re selling off the cow. I’m using a lot of cows in this interview. But you’re selling off the cow every time you flip a house. I’ve flipped a lot of houses and I still flip and wholesale to this day. I do a lot of it right now because the market is good for that in Pittsburgh. However, every house I’ve sold, I can’t think of one that I’m like, “I’m glad I sold it at that time.” If I would have held it for another five, 10 years, it would have kept producing that cash flow.
I came in this business to flip houses and get rich quick. I wanted to make $50,000 in three months and do it every three months and I’d have been fine. However, what happened was the market crashed on me on my fourth house when I was going to flip it and I had rented it for $1,300 a month. I was making about $300 a month–big pain at that point. But that house I still own and I rent that for $1,800 a month. I have about four more years on that mortgage and it’s about a $250,000 house. So, the end of the day, I’m in that house for about $110,000.
So, at the end of the day, if you hold these things longer, they’re going to keep producing that cash. We were talking about how we have these other ventures and we like to do these other things, whether it be charitable, whether it’s other businesses. Without my rental portfolio giving me that paycheck every month, I could never ever do that. I’d be in the rat race, the same rat race I got out of when I was working in the commercial real estate world.
Mike: Absolutely. There’s something nice for all businesses. But you hear sometimes in a gambling scenario where people are, “Now I’m just playing with the house’s money.” I don’t want to compare what we do to gambling necessarily. But I would say we have a rental portfolio that’s not as large as yours, but we could live off our rental portfolio and almost nothing is paid off at this point.
So it’s a nice thing to know, “Hey, I’m covered here and everything else I’m doing, I can take more risk. I can try more things. I can work less if I want to. I can do whatever I want because I’m covered over here.” That’s such a good feeling as a small business owner for sure.
Joe: Yeah. Here’s something that I always look at and I think the viewers and listeners can think about is those houses that I’m making $300 a month off of, $300 a month isn’t going to pay my bills. Now, you multiply that by my portfolio. We don’t make $300 on all of them, obviously. It’s less than that. But if you multiply any number in there that’s from $50 to $300 and some we make even more, multiply that by 300 and I think we’re approaching 350 at this point. Multiply and that’s a big number.
Now, I also pay my mortgages in that. So, in 10 to 15 years I take shorter notes from the bank because I want to be . . . I’m 35 years old. I want to be in my 40s and I want everything to be paid off.
In finance school when, I was getting my MBA, they say if you can borrow at a lower cost of capital, if the bank will give you a lower rate, you take it and you reinvest. But guess what? When you have a couple kids and you kind of want to breathe and you want to relax, having no notes on your portfolio and the cash just comes in, at that point, I can lower my rents by 50%.
So it gives you a lot of security by being a long-term thinker, especially as you get older and the flipping stuff starts becoming, “I flip this one. What’s next?” It will never end. Flip, make those big chunks, but don’ forget to keep a couple of those in the kitty that keeps paying you every single month.
Mike: Yeah. I know some people that in the last market downturn had relatively large rental portfolios and they just got a call one day from banks saying, “We’re pulling your line. You need to get these things paid off in 90 days or we’re going to take them,” basically.
Even people that have a lot of equity, it turns out . . . I don’t want to say the banks are bad guys, but they’re probably more likely to foreclose on something that has 50% loan to value than something that has 95% loan to value because there’s equity there for them to get their bait back. It makes sense, I guess.
Joe: We’re having a problem now with . . . banks won’t do anything but adjustable rates because no one knows where the market is going to go. So we do them because we have to continue to refinance with our strategy. We borrow money from wealthy individuals or institutions. Then we refinance once we’re done with the rehab and it’s rented. So we have to refinance. We have a lot of arms. That’s a scary thing. We like to be conservative. We only take as much debt as we need to pay that investor back. We can always take more.
We do a good job rehabbing and the appraisal comes out nice, usually, but we never get greedy because in that first downturn, 2008, almost hands down every one of my buddies, except for about two or three, a couple of them have been on your show, weathered that storm. Most of them went under. And the good ones, the key principle was, “I’m going to be conservative. I’m not going to get greedy. I’m going to make money, but I’m not going to get greedy and suck every ounce of equity out of these properties.”
Mike: Yeah. Absolutely. Well, how do you kind of predict markets? I know that it’s easy to say, “Hey, there are seven to 10-year market cycles.” But there’s a lot of money that’s made on those fringes, whether you get out a little bit early and you’re glad you did because things went to hell in a handbasket afterward, but if you get out too early you can miss a year or two of some really good time. So how do you stay conservative but make sure you don’t miss out on too many opportunities?
Joe: I think one of the best things is just watching what’s happening. If people are making irrational decisions, if people are paying the cap rates and someone is paying 3% cap rate on a Starbucks and you can get a government bond that’s bigger than that, that doesn’t make sense. That’s irrational. So irrational behavior can happen.
Now, if you see people wholesaling houses and they have a line up at your local REIA and there’s a line of people who are jumping on the deal and competitive bidding situations, if might be getting a little too hot if that’s every single deal. So I think watching the behaviors is a key example. And I think reading . . . don’t just read real estate stuff. Read stuff from Wall Street. I’m the furthest guy from academic.
We have a phrase from Pittsburgh called “yins” and my wife when I met her forced me to stop saying yins. So for me, yins are a [inaudible 00:21:22] who is not an academic, but force yourself to read some of this boring stuff from “The Economist” and they’ll give you a lot of relevant information. It might not be totally relevant, but if there’s a cycle in the oil and gas market and there’s a cycle in this and a cycle in that, it’s going to affect everything. So reach out and start digesting some of this more boring stuff about the actual global and local and regional economies.
Mike: Right. Any advice, Joe, for people that are . . . because a lot of real estate investors, you know this, they’re individuals, they’re lone wolves, they’re kind of by themselves. When you start to do more volume, you have a company. You’re surrounded by people that are likeminded. But a lot of folks are just individuals that don’t have access to other people and they tend to stay away from each other because they view them as their competition or whatever it might be.
A lot of these things, they become a lot more clear, I think, when people talk about them in a group. People share their ideas, you start to formulate what you believe to be true, but it’s hard to do that if it’s all just in your own mind and you can’t banter and stuff. Any advice to the smaller guys out there, the independents that don’t have the same resources that you do maybe?
Joe: If you’re watching this and you see Mike or me as competition, stop it. This is a big market and we’re big boys in this market, but we’re still little, tiny gnats in relation to the bigger picture. Even in Pittsburgh, I’m a small, small piece of the pie. There’s so much to go around.
So reach out to your peers, start asking people. Everyone knows an accountant, a lawyer, a guy in a different field. Ask them what they think and reach out to them and say, “How do you feel about the economy?” Just because they’re saying, “I’m an accountant and my clients are really contracting and they’re not expanding and watching their tax returns. They’re kind of stagnant.” Those are all good indicators that something might be happening. Or, “I saw this real estate company grow at 15 times last year.” That can also be equally as bad depending on where you think the economy is.
So if you’re not talking to everyone around you as a friend . . . and share your stories too. I’m an open book. People say, “How do you finance all this stuff?” “Here’s how I do it.” “Who are your investors?” I share my investors with people. Because I share, they share. I have all this community around me who will help me. If I’m down, I’ve helped enough people that they will come and lift me back up. So make sure you’re open and sharing.
Mike: That’s awesome. That’s good. I agree with that. I think early on, I was probably like a lot of people and I was more closed off to everything. But I realized, one, it’s a real lonely business if you live like that. But, two, I agree. I think most people are very open and willing to share and collaborate on stuff. It’s too big of a business to not do that. So I agree.
Joe: You’re doing it the best, man. You’re bringing the best stories to everyone.
Mike: Yeah. So where do you think . . . in terms of a cycle, you said early on that you’re preparing for a down market. So what are you going to do differently? Let’s say the market starts to trend down substantially and I don’t want to say crashes, but contracts a fair bit. What will you do differently? What would your next move be?
Joe: When I was in commercial real estate, I kind of watched the market crash in that realm. Then I was trying to get into the bigger boy picture and I saw all these deals that I couldn’t pay for because I didn’t have any money at that point.
So as I see the same thing happening again, I’m taking a lot of my assets right now as the market is high, selling them, hoarding cash, keeping my investors close to me so they know when I have to call them for the money call and I want to take some of these bigger deals, shopping centers, office buildings, and I want to make sure when those guys get hit, I’m the guy in there and I’m the knight in shining armor willing to pick these deals up cheap.
So we’re going to watch this downturn and we’re going to be buying lower-priced assets. If it’s not commercial, then we’ll jump right back into what our core competency is and we’ll go right back into a portfolio accumulation and buy more and more single-family rentals.
Mike: Sure. Any kind of advice to share for the financing side? I know in the last cycle, in my experience, a lot of people got hurt because they had one or two sources of financing and it just got yanked away. So I think a lot of people that I know that got hurt in that downturn that are still in the game have realized, “Man, I need to have a lot more sources of financing that are more stable so that I can kind of weather those storms.” But any advice on that front?
Joe: Financing is probably what I see as our greatest asset, not even our portfolio. We have a lot of investors who are very loyal to us. If you have an investor, treat them fair, pay them, make sure they get their money and then they will be loyal to you longer. If something goes down, at least you have another chance to sit in front of them and say, “I need more money,” and they’ll listen to you. Treat them fairly. I think diversify, even if you have one big . . . our initial funder, he gave us about $1 million and he controlled us and that was horrible. It didn’t feel good. He told us what to do. We were basically running our company with his money.
And then we diversified and now we have multiple investors with us, including this person. And this person is a great friend. It’s nice to have multiple sources so you don’t have to put up with someone pushing you around. So make sure you diversify and reach out and if you’re raising capital, I think the number one rule of raising capital is if you don’t ask for money, no one will ever give it to you. A lot of people think what we do is extremely interesting. It’s extremely profitable. They want to be in it.
You might be the person who can get them in the game without having to do the hard work, so just ask. It could be a Thanksgiving dinner or at a Halloween party. You have so many people around you that have money. They want you, but they’re not going to come out and say, “Hey, can I give you $50,000,” if they don’t know what you do. So ask. Just ask.
Mike: Yeah. And I think what you’re doing is . . . I’m not sure how big of a role this plays, but it seems like it would be a good thing and I’m not sure you’re doing it for these reasons, but you have a great story. You’re revitalizing the area you grew up in. You’re trying to make a difference in your community. That’s something people want to be a part of, whether it’s financing or not. So I would encourage . . . I’m not an expert at raising private money, but I’m pretty good at common sensical stuff.
I think that there are a lot of people out there, there’s a lot of money on the sidelines right now that doesn’t want to invest in the market that likes the type of stuff that we do. They want to be a part of something that is going to change their community or just kind of impact the neighborhoods they live in.
Joe: Yeah. Definitely. Sell that story. The story when I was first starting out when I was 23 was I was just pumped up about it. I came in. I asked the only two rich people I knew with a lot of energy. They saw it in my face. They knew I loved it. They said, “Hey, here’s $30,000. If you lose it, make sure you still come by for Christmas dinner.”
Mike: Yeah. That’s cool.
Joe: So show that passion when you’re asking for this money and I think people will see it whether you’re an older, sophisticated investor or you’re a newbie and you just want to get in the game.
Mike: Awesome. Well, Joe, any kind of final words of wisdom? We talked mainly about market cycles, but anything we talked about today? We have a couple more minutes here. Any final words of wisdom?
Joe: One, action, action, action. Analysis paralysis, I see it stunt so many people. They always say, “Who’s my guru? Who’s this person? Who’s that person?” Everyone can be my guru. I still listen to stuff online. I still take courses. I want as much knowledge as possible. But do not let knowledge stand in your way of action. The best lessons are by doing. I would say to make sure the capital raising is extremely important and watch these market cycles. Watch them and don’t do what the herd is doing because you will not make money and you will eventually get burned.
Mike: Awesome. Well, Joe, thanks for spending time with us today. I definitely appreciate you being here.
Joe: Great, man. Thanks for having me. I really appreciate it.
Mike: Hey, if folks want to learn more about you or some of the work you’re doing, where would they go? Where should they go?
Joe: They can follow me on Facebook at Joe Calloway, Re360 is my company. They can Google that. RE360 LLC is our Facebook page and we’re on Twitter and all that fancy stuff as well. So Google it, RE360 in Pittsburgh and we’ll come up.
Mike: Awesome. Joe, thanks again for being here today. I wish you all the best.
Joe: Thank you.
Mike: Have a good day.
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