George O’Brien on Growing Your Real Estate Portfolio By Starting Early – EP 235

The Fastest Way To Build A Six Or Even… Seven Figure Real Estate EMPIRE! 

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If you’ve been thinking about making the plunge into real estate investing, then you’ll definitely want to hear the wisdom from today’s guest, George O’Brien. After 6 short years as a real estate investor, he’s already retired and is living life on his terms. 

George got his start in residential real estate and smaller multifamily deals and then quickly pivoted to larger multifamily properties after closing on 40 deals in a two year period. With his background in construction, he was able to do a lot of the work himself early on until he was able to grow his team. 

He attributes a lot of his success to investing in smaller deals, which allowed him to forge strong relationships with like-minded investors, and build trust with the banks and his community. 

In this conversation, you’ll learn the steps George took to quickly grow his portfolio, how to invest in real estate no matter where it’s located, and why the best path to success is starting early!

Key Takeaways with George O'Brien

  • The importance of getting started early as a real estate investor. The sooner the better.
  • What it takes to successfully pivot from residential investing to multifamily properties.
  • Why it’s okay to focus on smaller investments and properties that are under 75 units and how these properties were the foundation for his portfolio.
  • Why George prefers the direct to seller route to find new deals.
  • For a successful partnership, align yourself with like-minded people.
  • The importance of doing your due diligence, especially when you’re making cold calls with people you’re not familiar with.
  • Always be ready to capitalize on deals and make sure that you have the resources ready to go so that you don’t risk ever losing a deal.
  • How to live where you want and invest where it makes sense.
  • Be wary of working with family and who you choose to partner with as it’s much harder to end a relationship then to start one.
  • How you can showcase your talents and attract outside investors.


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Josh Cantwell: So, hey there, guys, welcome back to Accelerated Real Estate Investor with Josh Cantwell. Today, I am interviewing a relatively new friend of mine. His name is George O’Brien. He’s the owner and CEO of He was an accomplished senior executive for the YMCA. A lot of the guys would have grown up going to the Y to swim and play basketball. He was an executive at the Y and he took his expertise being a senior executive and used that to begin investing in real estate at 36 years old. Today, he’s 41 years old. He’s fully retired from his portfolio. He owns over 400 units of multifamily. He has experience in spearheading those strategic initiatives in the YMCA and working with multiple people, some of the skill sets that he’s used to focusing on building his portfolio and being a leader of a team of partners, of contractors, of vendors, of community leaders for brokers and private investors to help him build a bigger, stronger community, and a bigger, better portfolio.


Today, with George, we’re going to talk about a few things. Number 1, we’re going to talk about what it takes to convert from residential investing to multifamily and how to acquire your first multifamily property. Number 2, we’re going to talk about why it’s okay to focus on deals that are smaller, why it’s okay to focus on deals that are under 75 units, and why that’s an easy place to build wealth going direct to seller. We’re going to talk about George’s favorite strategy to find deals, which is direct to seller, number 3. Number 4, we’re going to talk about why George wishes he started earlier. He mentioned this several times in the interview, “I wish I’d started earlier. I wish I’d started earlier. I wish I’d started earlier.” You’re going to hear that.


And lastly, number 5, you’re going to hear about George and his concept of live where you want and invest where it makes sense. And George is going to tell you about his journey of relocating from Pittsburgh to the beaches of Florida and how he’s able to raise his family and go to the beach nearly every day. George actually tells the story about how he’s able to walk to the beach. He knows exactly how many steps it takes. It takes exactly 51 steps for him to go from his front door to the beach and how he was able to retire at a very young 41 years old. You’re going to love this interview on Accelerated Real Estate Investor with me and George O’Brien. Here we go.




Josh Cantwell: So, hey, George, listen, I’m so excited to have you on Accelerated Real Estate Investor. Thanks so much for jumping on the show.


George O’Brien: Yeah, thanks for having us. 


Josh Cantwell: Hey, listen, George, I always like to, especially when I meet a new guest, somebody that I’m introduced to, refer to, like you, and have you on the show to talk about your investing strategies, I’m always curious to see what people are up to right now in today’s market, a project that they’re working on, their latest and greatest investment. So, tell us a little bit more about what you have cooking.


George O’Brien: Yeah, so typically, I’ve been staying in the multifamily small commercial, jumping into something outside of our comfort zone where we have a 97-unit RV park under contract here in Florida. Super excited about that. It’s the first one in our portfolio, and the third in my partner’s portfolio, doing a cash-out refi. It’s one of our business models. We’re going to cash out, refi, and it’ll reduce our monthly mortgage payment and give us about $600,000 of resources to reinvest in some other markets and other real estates. And I have about 110 units under contract to close here in the next two months across three different deals.  Yeah, so we’re busy.


Josh Cantwell: Nice. Fantastic stuff. That’s exciting. I know, George, your focus has been on the smaller multifamily stuff, stuff we talked about before we started recording, anywhere from two units to really 40 units, kind of a sweet spot in that 20 to 25-unit range, but I know you’re also looking at some larger assets, but you guys had a lot of success with the smaller apartments, smaller multifamily. Tell us a little bit about that. Tell us a little bit more about how you got into it. Has it always been the focus? Or were you doing other residential investments first and then started buying some cash flow deals? And I guess, I should hear this from your perspective because there’s a lot of people in our audience who are probably trying to make the same exact pivot. They’re trying to go from raising investments, maybe SFR or single-family into their first 20-unit or their first 40-unit or their first 14-unit. So, tell us a little bit more about your transition.


George O’Brien: Yeah, I mean, we knew real estate was always an avenue we wanted to explore. And the barriers to entry were the cash and the resources to be able to get in. So, we pulled some equity out of our home and bought a total of 6 units and kind of did the work ourselves and sweat equity and then built that up and got a good rapport in the market and a good, strong brand with the banks. And we’ve just continued to know that, although we weren’t taking down a 20 or 30 or 40-unit, we were buying in an area that we could get 30 or 40 units total within a six-month period, all within the same block or within a couple of blocks.


So, we’ve seen a lot of gentrification with that. And then that also allowed us to showcase our talents and what we’re able to do and then also bringing in some outside investors. And then that’s when we were really, truly able to scale because I stepped back and reflected a few years ago, we had 40 deals that closed within a two-year period of time, and the average unit per close was four units. And so, if I do another 20 closings in the next year or two and I average 15, 20, 30 units per closing, that’s where really where you’re going to make generational wealth, be able to really set up your family and your generations to come.


Josh Cantwell: Got it. What did you learn, George, by doing those smaller deals? What are some of the things that you think on the smaller deals, the four units, the eight-unit, the 10-unit deals, the two-unit deals that still apply to the larger deals, even though you’re already getting bigger, you’re making offers of larger portfolios now? What are some of the lessons that you learned from the smaller things that you think transition regardless of the size of the deal?


George O’Brien: Yeah, I mean, you can’t do it yourself. That’s one of the biggest things. You need to align yourself to other like-minded individuals that have the same vision and passion for real estate, and don’t bring everybody in. If you’re a strong underwriter, don’t bring in three other people that are strong underwriters. Bring other people that have different skillsets and areas of expertise because that’s really how you can truly grow and scale. And right now, I don’t even look at underwriting. One of my partners does that. I really look at the asset itself and the structural integrity of the building, what the CapEx is going to look like to improve it, all those sorts of things.


So, really, if you want to do this by yourself, you’re never really going to get to the point where you’re going to have hundred-plus, thousand-plus stores. And if you’re okay with that, that’s fine, but identify that’s your business plan and stick to it, whereas if you want to really grow and you want to grow with good people and you don’t mind having a beer with somebody, but you don’t want to get in a deal with anybody that you can’t necessarily have a good conversation with. I tell everybody all the time, don’t be in a hurry to get into a partnership because it’s like a marriage, very easy they get into it, but it’s extremely expensive to get out of it.


Josh Cantwell: Yeah.


George O’Brien: So, align yourself with the right like-minded people, and you’ll have a good time.


Josh Cantwell: I like good partnerships and I like beer. So, we’re on the right path there. So, George, from your perspective, again, you have somebody else focus on underwriting. You’re focused more on the asset. Describe to our audience a little bit, who are some of the players, like who are the people, not necessarily people, but what are the positions, in your opinion, in a successful partnership and commercial multifamily that need– when you have to have somebody sitting with its property management, CapEx, etc., what are some of the key positions in your mind that if you’re not going to do it all, people that you have to align yourself with, and what do they need to be the expert at to make sure that you’re covering all your bases?


George O’Brien: Yeah, obviously, you need to have strong legal, a strong accounting, someone who has an underwriting experience, someone who is a good networker, someone who can go out there, find deals, find other investors who want to get part of the deal, someone that’s an extrovert. And it’s okay to have a couple of introverts in the deal, someone who has strong background in construction and CapEx, property management, but it’s nice things, too. And I say those things, there are six to eight different skill sets there. You don’t have to have eight people in it as part of your partnership. You can say, you can have two or three that have a general understanding of all those, but then you farm that out and contract that out with strong people that you trust. So, that’s one thing that a couple of partners of mine, they form partnerships in those eight people. It’s tough to get a lot of things done when there are eight people that are all equal leaders within a group. You want to have a nice core group that all have similar knowledge, but also know what they know, and I know what they don’t know. And then you hire or contract that out to make sure you can fulfill the obligation of that LLC and that property.


Josh Cantwell: Yep, I like that. Yeah, in our business, I handle all the cap raise. I’ve got some partners that do it kind of as a side hustle, but it’s my job, it’s my responsibility. I also handle all the underwriting because I want to make sure that the deals that we’re buying, that they’ve got my stamp of approval. I’m the CEO, I’m the majority shareholder. If we’re signing on, and you kind of bridge that, we have to personally guarantee it. That’s my ass that’s on the line. So, I want to make sure. So, those are the two things that I do.


And then, my partner Tyler really focuses on acquisitions. He’s networking with brokers, networking with wholesalers, looking at off-market deals, looking at student partnership deals that we have, as well as direct-to-seller deals for acquisitions, but then he also is basically the asset manager who oversees our property managers. We use third-party property managers for everything. And we self-managed for a while, but that’s Tyler’s swim lane. And then Glenn’s swim lane for us, Glenn is really our Chief Strategy Officer. He oversees our CapEx division, so he sits above our VP of construction, but Glenn’s also a numbers geek, like an AppFolio, PNL, balance sheet. What’s going on with CapEx? Where are we spending our money looking for blind spots and things like that?


And then, like you said, George, we farm out our CPA and our CFO. CFO is not a partner, but he does have some equity in a few deals, but he’s not a major partner. And he’s really a silent partner, but he’s our CFO and does all the marketing, I mean, all the accounting, but then we’ve got separate staff for marketing, separate staff for operations that are just staff, that are not partners. So, I agree with you on that, man. It’s just about finding what makes works for you.


George O’Brien: Right.


Josh Cantwell: George, help us understand. So, your first couple of multifamilies that you guys did, where you guys kind of caught the itch, you’re like real estate’s the thing. I love this just as much or more than my regular day job. What did that look like for you? Like when did you catch the action, really find some passion for real estate? And what were your first couple of deals like?


George O’Brien: Yeah, I mean, the normal 80-20, from a loan perspective. And again, we bought things in a distressed manner and we went in and did a lot of work. I have a construction background. I was a foreman for a large construction company, so again, called in a lot of favors and did a lot of the work ourselves. And then just from there, I like to see in the finished product, one, you know you’re adding value to this asset. And the thing that I always really enjoyed was the people that you’re now able to make a difference and provide really nice housing to these individuals in the same breath, make a good bit of money off of it.


And now, that’s continued year after year. Now, we’ve only been doing this for five years. And we started with a couple of units. Now, we’re just shy of 400 while we’re still working W-2 and raising a family of four. One of the things I love now is we’re doing a lot of third parties and bringing other investors in, and they’re telling us stories that now, they don’t have to work as hard, they don’t have to have a second job, and they’re able to focus on their family and focus on their major career. Knowing that they’re working with us, they know the integrity we have where they see the results. And now, they just continue to come back, refer family, and it’s just really expedited our growth in the last 18 months, so seeing that and hearing those testimonies of how we’re changing other people’s lives while still maintaining having a strong asset that we’re taking care of, but then also providing great housing for individuals.


Josh Cantwell: Nice. I love it. George, describe for us a recent feel like pick up either duplex or a fourplex or a 20-unit. What does it look like for you? How do you guys structure it? How do you fund it? How do you syndicate it if you’re syndicating with other investors? What’s your all-in number? And what do you think it’s going to stabilize out at? Maybe you just pick a deal, kind of walk through that entire deal, how you acquired it, what it’s going to stabilize out at, the income, structure, partnership. Take us through one of your most recent favorites.


George O’Brien: Yeah. One recently that we– back in ‘18, we had a five-unit on a contract. The owners were in pretty rough shape. They had deferred taxes and they were in a pretty rough financial spot. We had this five-unit on the contract. It’s the first JV deal that we had. Everything else, my wife and I were buying with our own cash, brought this partnership in. I have a philosophy. It’s better to have a percentage of something than a hundred percent of nothing. So, I brought some partners in. As we were going through that sale, that purchase, the sellers reached out, “Hey, we have a 16-unit.” And they wanted to sell. So, we bought the 16-unit off-market for $600,000. My father and I bought it, rented around 550. We stabilized it, put about $100,000 thousand into it. It appraised a year and a half later for $1.3 million.


Josh Cantwell: Nice.


George O’Brien: And so, their average rents there are 875. It’s a cash cow for us. It provides him at 62 years old, retirement income for as long as he needs. And it’s a legacy gift from him to our kids, which is great. A very similar concept. We have a 13-unit right across from our office under contract, half-million dollars. We’re doing seller financing on $100,000 of it. We’re going to get a banknote for 80-20, a promissory note after the fact. So, essentially, we’re getting into this deal without any out-of-pocket cash, which is great. Rents are six and a quarter. The rents are going to go up to 850 without having to put any CapEx in. So, that’ll be a screaming deal. We’ll refinance that out. And then we have a 21-unit on the contract that we’re actually buying the LLC versus buying the physical property because we’re trying to be mindful of the tax changes that would happen if you would buy the physical property versus buying the LLC.


So, a couple of smaller multis, we’ve kind of navigate through one good case statement of what can be done. We did a cash-out refi on that. We got all of our money back from the improvements and the money to close, and then other things that we’re finding off-market in creative ways to get it done without having to put a lot of cash in or increase your expenses.


Josh Cantwell: Nice. I love it. Love it. George, along the way, with these smaller multis, which, by the way, I love it. I’ve got a real close friend of mine. His name is Jack. We’ve got 164-unit together, but Jack also has a bunch of 20 units and 25 units and 35 units and 16 units and little old properties that have built up his portfolio now to the point where he can easily buy 100-unit or 200-unit on his own, but he started very, very similar to what you did. I’m curious now, that you’ve done some number of those smaller deals, what are some of the good decisions that you think you made? What were some of the positive things that have come out of that? And then after you answer that question, I’ll ask you, what are some things that you learned, some challenges that you faced, or some things you do different? So, let’s start with the good news. What are some of the positives? What are some of the lessons from the smaller deals, again, that you think worked well, that will translate into some of these larger deals as you do those?


George O’Brien: Yeah. I mean, the smaller deals in that that we form these relationships with other investors who are like-minded, that we both or we all have a similar vision of what we were looking for and how we want it to impact our family and our portfolio. And we all just divide and conquer. They keep a shared Google doc that we all assign to each other, all have tasks. We’ll probably have eight to ten of those and over 150 units closed by the end of this year. And if it was just me, I’d probably have 25.


Josh Cantwell: Right.


George O’Brien: And you bring as many people to the table. Don’t get too many people in the deal, don’t know the deadweight. Everybody takes an equal share, but I wish I would have done that five years ago.


Josh Cantwell: Nice.


George O’Brien: But in the last 18 months, it’s really opened my eyes that I really like the group we’re working with. We’re adding a few people here and there, depending on the deal, depending what’s their interest in X, Y, and Z, the locations. So, I would say the biggest thing is just the relationships and the partnerships we’ve built because we’re just scratching the surface of what we’re going to be attacking here in the near future.


Josh Cantwell: Got it. Love it. And what would have been some challenges? Have there been some things that stand out? You’re like man, we hit a brick wall on that one, or man, I really got my teeth kicked in here, but we learned a lot. Everybody has kind of a deal or two like that. Tell us about some of the lessons you’ve learned along the way.


George O’Brien: Yeah, I would say two things. Early on, we raised the money to bring the property to close, and maybe a couple of bucks for CapEx, and we didn’t raise all the money for CapEx. We’re going to subsidize the CapEx for the operations. And that doesn’t necessarily happen because you get in and something happens that you didn’t anticipate for. So, we were pulling a lot of our personal resources and doing cash calls with the other investors, luckily, either family members or close friends so that wasn’t as uncomfortable, but as we work with folks we don’t have a relationship that close with, we’re going to want to make sure we do our due diligence and make sure not only the cash had closed, but also the cash to fund all the capital improvements is raised up in front.


And the other thing is like we just started doing off-market cold calling and skip tracing and in the last six months, and if we would have done that three years ago, we could have bought four or five times what we’re currently getting. We just lost a 36-unit, 1.7 was the offer, 1.6 was the list price. We ended the winning bid with 1.8. There’s a lot of big firms and agencies out of the Pittsburgh market. We’re based out of the Western PA market. We’re seeing a lot of the larger corporations that are coming in, and they have the money to throw at it because it still makes sense that 1.8, 1.9, even 2. And so, if we would have gotten to those sellers before it hit the MLS or broker’s hands, we would have done much better. We’re kicking ourselves for not focusing on those larger assets and then some of the smaller multis.


Josh Cantwell: Got it. Are there any pointers, George, that you would give our audience regarding doing that direct-to-seller marketing? What’s worked for you guys regarding the cold calling, maybe doing some mailers, looking for rent signs, or for sale signs or signs of distress to go direct to the seller?


George O’Brien: Yeah, I think you get a good database of those properties. We’re searching the larger parcels. We’re able to look things up by the parcels and the multis and then the years of ownership. And you’re able to typically find those and make those calls and know just because don’t get discouraged, know that just because they’re not returning your call right away, they have it. Of the six deals that we’ve done off-market, four of them called us back months after we had the initial conversation. People, if you are out of the area, make sure you have a local phone number because a lot of people won’t answer from out of the area. And the phone number, that’s one thing that a lot of people have said that they’ve identified us as a local investor and they really wanted to sell us to somebody local or somebody outside of the area.


And again, just be ready to capitalize, make sure you have the capital raise, and you’re ready to pull the trigger because you can’t go in and act like a big player and get these things on a contract and not be able to have the resources. That’s one thing I made sure as we were getting a lot of these things on a contract, make all these calls and listen. This is great that we’re getting these things on a contract, but we need to make sure that we have the ability to get these things closed and get them financed.


Josh Cantwell: Yeah. I got involved in a huge deal, a $70 million deal. It’s got $100 million stabilized value, 552 units in Houston because my buddy Shane, who is one of my partners, was way short of money about a week before a closing, called me with eight days left after his third extension and was about to lose 650 grand in earnest money. It was like, “Dude, I’m short.” “Alright, dude.” So, raised the million and a half within eight days, and we got across the goal line, so.


George O’Brien: That’s great.


Josh Cantwell: I don’t like those situations, and deals can still get down at the last minute, which we’ve proven, but certainly makes things uncomfortable for everyone. But absolutely, yeah, I mean, keep making sure they have the cash to close early, kind of soft commitments from investors early. And then when you have that deal, you’re in the underwriting phase, underwrite, make the offer, got some soft commitments already. People warmed up. And then once you get through due diligence, while you’re doing due diligence, that 30 days is the best time to really warm up all the investors, do a webinar, and have people committed because once your 30 days is off and your money goes hard, you want to know that you have a very high likelihood of recruiting all the capital to close. That’s how we typically do it. Awesome stuff.


So, George, I’m curious, before we were getting ready to turn the record button on, you had mentioned that you recently moved to Florida under the concept or the philosophy of your live where you want to live and invest where it makes sense. Tell our audience a little bit more about that and how you pull that off in your business, in your personal life.


George O’Brien: Yeah. So, my wife and I both had executive-level positions, W-2 earners, and we knew eventually we’d like to be able to relocate our family to Florida. We have some family here on the Atlantic side. And we came down and we knew we were close to be able to do that, but initially, we thought it was going to be a vacation rental and Airbnb and then come down, stay in our own place. And we got to the point where I knew I was able to retire and said, you know what, I think I’m leaving a lot of money on the table by not being full-time real estate professional. And so, we pulled the trigger.


And we identified Tampa, Jacksonville, and Orlando as the markets, obviously, because they’re strong markets for investing when it will be somewhat close to those regions and also have the ability to jump back and get up the Western PA quickly on a nonstop flight. We decided, based on how we were performing as a property management company but also our portfolio, that we were going to do it. And she was going to work remotely, and I was going to do the same. And we knew we had a strong team already in place up in PA and we did it. The kids are all in elementary school, and it’s been just the best. It’s a game-changer, and all the stressors you have in your life and to be able to walk out the front door and get to the beach within 51 steps, it’s a game-changer. It really is.


Josh Cantwell: You won exactly.


George O’Brien: We did, man.


Josh Cantwell: It pays it off, but more than once, I can tell.


George O’Brien: Yeah.


Josh Cantwell: Fifty-one steps to the beach.


George O’Brien: So, just set a goal. I had a screensaver on my phone of myself and our kids when they were a little bit younger and up in New Jersey. We go there every year for a vacation. And those just to remind me every morning while I’m getting up, while I’m hustling, while I’m working at midnight, why am I doing these things on a Saturday? It’s because I wanted a different life for our family. And now, I change that screensaver because I’ve accomplished it. Now, I have something else.


Josh Cantwell: Yes, yes, yes. I’m interested to see what’s on the screensaver next. Maybe something else a little bit even more exotic, which is fantastic. Good for you, man.


George O’Brien: Yeah.


Josh Cantwell: So, George, help me understand the first deal. Let’s go back now a little bit further to your start. You had a W-2 job. You got the itch for real estate. Like, what’s the first deal look like? It’s probably a little bit nerve-racking getting into the game, but you knew that real estate offered a lot as far as appreciation, depreciation, cash flow, equity, blah, blah, blah. What really got you into it? What was your passion for it? What was your draw to it? And what was the first deal like?


George O’Brien: Yeah, the first deal, I talked to the realtor who I really like. She was a young real estate agent and she hustled for us to finance our family home, and I told her I was looking at an off-market deal, and it was pretty distressed. There’s a three-unit. And we sat down, she talked about goals, identified what we were looking for, what kind of cash we had to be able to get into the market. And she found us an off-market deal that was, again, a little rough, but I had a stabilized tenant on one side, and the other side needed some work. So, I knew. Hey, at least, I have the cash flow on the one side to cover the note while I fix up the other side, and then I can stabilize and go back and forth. So, that’s pretty much the model we’ve had.


You buy a place, make sure it’s occupied so you have the cash flow to come in to pay your note, use your personal resources to fix up the other side, reestablish some market, and then either asset tenant to bump over to the finished side or let them know that we’re going to raise our rents 20%, probably 20% below what market should be, but hey, we need to get to you to this point. You’re more than welcome to stay or move over to the other side. And we’ve pretty much rinsed and repeated that up until a few years ago. Following the burn method, but I don’t even know what the burn method was. That was just something I was doing.


Josh Cantwell: Yeah.


George O’Brien: And then what we did is we…


Josh Cantwell: Like others that aim for it.


George O’Brien: Yeah, yeah. You refinanced it out, got lines of credit, the bank seeing what we were doing, take the banks into the properties and show them what we were doing, send them pictures, send them testimonials, and then they just really fell in love with us. So, a lot of the banks were doing 80-20 closings. They’d given me a line of credit based on the improved value. A lot of times that I was using that line of credit for funds to close on the deal, but you weren’t able to do that if you had a strong presence and strong relationship with that bank. And they’ve seen results.


Josh Cantwell: Nice. Love it. So, George, now that you’ve had success, 400 units. You’re still growing. You’re living in an amazing place, 51 steps exactly from the beach, and have a portfolio. I love the idea of the Pittsburgh portfolio or the Pennsylvania portfolio. We’re from Cleveland, and I love the Midwest, but for a lot of people who say, like, “Wow, George has made it.” When you think about that and you look back at your younger former self, you look and talk to some of our audience, maybe not quite reached the levels that you’re at, what kind of advice would you give to younger George? What kind of advice would you say, “Hey, man, this is just what you got to do. And these are a couple of mistakes that I made along the way. Don’t do this in your journey.” What would you kind of say to your younger former self?


George O’Brien: You definitely start earlier. There is a mentor of mine, that very first duplex I had bought. He had a five-unit down the road. I went as a secret shopper to see what the market was, what the competition looked like. Six months later, after I did that, I reached back out and let him know, “Hey, listen, I was actually just coming to check out the building.” And he goes, “I understand that because I was your age once, too.” And I said, and I asked him that question, “If there’s one thing you would have done differently?” He looked at me before I even finished my sentence. He goes, “I would have started earlier and have bought more.” And that right then just lit a fire.


And then, since then, that’s what I tell everybody. Start as early as you can, make sure you get educated first. And if you do bring people on, make sure those people are people that you trust and people that you want to be in a relationship with, again, because partnerships are easy to get into, but they’re extremely hard and challenging to get out of. Be mindful of working with family because there are always challenges with that and make sure you have a strong operating agreement if you do get in there with family.


And then, in 2019, I started investing in myself from a professional development standpoint and really learned. And from that point, we’ve grown by three times. And it’s because I was just doing things myself. And now, I got to that point where it takes more than just myself to do it. And getting into some of the bigger deals has really opened my eyes. And it’s networking. So, network, network, network, build relationships. Make sure you save that information so you can reach back out. Continue to engage the people you’ve met. Don’t just go get business cards at a conference and never reach out to people. We’ve all been there. We’ve all done that. Continue to develop a relationship because they’re lasting relationships that you, their kids hanging out together. They bring you a deal when they don’t even need to. I have a 51-unit on the contract. It’s a screaming three to one ratio from a cash flow standpoint. I could have taken it down myself, but I bring in two partners because I knew I wanted them to be part of it because I knew that that would pay for itself ten-fold. The one just got brought that 97 RV park in, and then we got another 100 units with the other individual. So, bring people into a deal because they’ll bring you tons of deals on the flip side too.


Josh Cantwell: Nice. Love it. So, George, we always wrap up with our guests with the final five, we call it, five quick questions, five fast answers. Are you ready for this?


George O’Brien: I’m ready. Let’s do it.


Josh Cantwell: Alright. So, your favorite way to find deals?


George O’Brien: Off-market.


Josh Cantwell: How off-market, like through what channel?


George O’Brien: Cold calling.


Josh Cantwell: Perfect. Love it. Favorite way to find capital for deals or fill up your capital stack?


George O’Brien: Just relationship. Continue to build relationships.


Josh Cantwell: Got it. What’s your favorite thing about moving to Florida and being 51 steps away from the beach?


George O’Brien: To see my kids in the ocean just about every day.


Josh Cantwell: That’s a kick ass, man. What’s your favorite piece of advice that you’ve ever been given?


George O’Brien: Work smarter, not harder.


Josh Cantwell: Love it. And when you want to get away from the business, get away from the hectic side of life, and being a dad and being in business with your father, where do you go? What do you do to decompress, to recharge, and to think?


George O’Brien: I just do whatever my kids want to do for the most part, whether it’s go to the arcade, ride bikes, take them and do drills with our oldest that’s here with us who is nine years old, and we were out doing drills, basketball. And I remember being a kid playing ball as well, and a basketball coach. I noticed your shirt there as well, because I’m the coach.


Josh Cantwell: Because I’m the coach, that’s why.


George O’Brien: That’s exactly what I’ve said to him the other day. “Why are we going to practice with my left hand, dad?” “Because I said so because I’m the coach.” Just engulfing myself because, again, we’ve all been there, W-2 working. Where we really engage with our kids while we’re thinking about all these other things? So, now, I have the ability, I can work and I grind, but when it’s time for the kids, I can decompress, just focus on them 100% and not think about anything else. I work when I want and I play when I want.


Josh Cantwell: Yeah, you’re probably just like me, like when you’re actually doing something you really enjoy, like being a family man and playing with the kids, probably when you have some of your very best business ideas because you’re not even thinking about business, right? So, your mind is free to float. And as you’re playing with your kids, and all of a sudden, it’s like, oh my God, one idea just pops in. And you like maybe take a quick note on your phone or something and then go back to playing with the kids and engaging with them. So, a couple more questions, George. This is a fun interview. What do you think is the best decision you’ve ever made?


George O’Brien: Getting into real estate and marrying my wife.


Josh Cantwell: Yes. Oh, yeah. Get into real estate and get married. And what do you think is maybe one of the biggest mistakes that you’ve made or one of the decisions that didn’t go your direction?


George O’Brien: I didn’t start early enough. I think we bought our first deal, 36. And we have a young man who works with us in our property management company at 22 years old. He was part of a three-unit deal, and I told him that same mistake. I wish I would have done this earlier. I want you to be able to retire when you’re in your 40s and then do what you want.


Josh Cantwell: Yeah, love it. Fantastic stuff, George. Listen, so people can reach you if they want to reach out, go to George, any other place or way that our audience can engage with you if they want to reach out?


George O’Brien: Yeah, we’re on Facebook. We’re on Instagram. That’s our property management site, but the biggest thing is we want to be able to tell our story, learn about what your listeners’ goals are, and if we can help. Again, we’re a little bit smaller trying to get into the smaller multis and some of the larger deals, but if there’s any way I can provide value to your listeners, I’d be happy to spend time with them and talk about their goals and how we can maybe help.


Josh Cantwell: That sounds great. George, thanks so much for joining us today on Accelerated Real Estate Investor.


George O’Brien: Thanks for having us.




Josh Cantwell: So, there you have it, guys. I hope you enjoyed that interview with George from I had a blast. He’s such a fun, you could tell, like fun-loving, family loving, family man, good time. I enjoyed that, getting to know George a little bit better. I wouldn’t be surprised if George and I do JV on a deal or do a deal together sometime soon in the Pittsburgh market. It’s just about two to two and a half hours from my market. So, George and I are in touch and communicating about some possible deals. Looking forward to that.


Also, I did want to announce that we are about to have our next Forever Passive Income Mastermind, so face-to-face mastermind. We do it three times a year. That is coming up here in about two months. That’s officially been scheduled in about two months from now. We will be having our next Forever Passive Income Mastermind. That mastermind is a coaching program and a mastermind group and a partnership program where I partner with students. We do student partnership deals all in the multifamily and apartment space. If you are interested in learning more about that and applying to be a member of the Forever Passive Income Mastermind program, go to SREC stands for my company’s Strategic Real Estate Coach. There you can apply, get on the phone with my team, see if you’re fit for the program, and get enrolled. It is not cheap. It is also very much worth it. If you’d like to come to our next face-to-face mastermind and meet up with me face to face, go there, apply. I hope you get accepted into the program, and we’ll see you at our next mastermind.


Also, don’t forget to subscribe. We release a new podcast weekly. Don’t forget to hit the subscribe button so you’d never miss another episode. And we’ll see you next time on Accelerated Real Estate Investor. Take care.

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