305: Client Case Study: Real Estate Investing Through The Great Recession with Sean Carroll

This show is produced by the Hartman Media Company.

For more information and links to all our great podcasts, visit hartmanmedia.com.

Welcome to the AIPIS show for accredited income property investment specialists and those who aspire to be. If you're a real estate, mortgage or financial professional, this is the place for you. We'll explore innovative investment analysis, sales marketing and income generating strategies for the most historically proven wealth creator income property. Learn from the experts as they show you how to build a better business and a better life.

It's my pleasure to welcome one of our clients to the show. Has been a client for years, overcame some challenges, did a great job of it, and is now on the path to to financial freedom. His name is Sean Carroll. He's a New York City based professional actor and entrepreneur. He's got over 15 years experience in several industries. After losing nearly every penny during the Great Recession, he built a top producing real estate sales team in one of the toughest real estate markets in history by becoming the local expert on short sales. So we all know about short sales. We've talked about that before. He had some innovative strategies that he shared via his BL and his online marketing strategies. Later, after starting and growing his business consulting company and digital marketing agency, he made a major career shift to become a little poorer.

Yes, we'll get to that. He decided to follow his passion of becoming a professional musical theater actor. Sean brought his entrepreneurial skill set to his acting career and in just a few years he has been fortunate to appear in dozens of musicals in New York City, in regional theaters across the country. He continues to invest in real estate and is excited to be launching his new podcast for creative artists and entrepreneurs in early 2020. Sean, how you doing? Welcome to the show. How are you doing?

Great, Jason, thanks for having me on. It's always good to chat with you.

Yeah, you were a client and then I think you saw somewhere on social media that I happen to be in New York City or I talked about it on the podcast and we kind of connected then and have been talking ever since. And when you said you lost every penny during the Great Recession, what were you doing back then? And like we're talking what, 2007, 2008 maybe?

Yeah, we went through a Chapter 13 bankruptcy in 2008 where we restructured hundreds of thousands of dollars of debt and lost some properties and I was a schoolteacher for about eight years and.

And when you say we, you mean you and your wife Tanya, right?

My wife Tanya and I, yeah, we've been together a long Time. And I'm proud to say we navigated that. It was one of the toughest periods of our life, but we came out the other side. At the time I was teaching. I was a high school choir director for eight years. I had a good, stable job, great benefits, great salary. And I decided to get my real estate license like a lot of people in 2004 when the market was, you know, charging red hot. And I was going to do it part time because some friends of mine, we're doing, you know, a deal or two over the summer and just making five or ten extra thousand dollars. And that was originally how it started. And then I made a sale in like the first week. And I. That was like the worst thing that probably could have happened because I thought, well, this is an easy business. Yeah. And literally what happened, Jason? I was on floor time at the office, and you probably remember floor time.

You know, so what that. What that means is, is just for the people that don't know, that's like at a real estate office or a, you know, any, like a car dealership or whatever, right? You sit and you just answer the phones and do kind of clerical work for the hope of getting what's going to own as an up call.

And that's.

That's the client who wants to buy the big multimillion dollar property or sell it. And, you know, you might get it. So, yeah, you were doing floor time. And what happened?

The market was so hot that the phone rang. A client called on a newspaper ad for one of our listings that shows you a little bit about how what was like back then. And she wanted to see this property. It was a $570,000 property. I showed it to her, she bought it. We wrote a contract. It closed 60 days later. And I made my 3% on that deal. And I thought, well, this is the best business ever. And so I actually resigned from my teaching job at the end of that year and decided I was going to do this full time. And while that was happening, my wife and I also started buying properties in Florida on pure speculation. We found some condominiums in Daytona beach, and I bought a property there. We actually, the first one we bought with 20% down. We paid 300,000 for it. And 10 months later, I sold it for 380,000. Like, that's kind of how the market went. So I thought I was a genius. And unfortunately, I duplicated that behavior over and over. And when the market shifted and the rents weren't there to cover these massive mortgages, we had including our primary residence. We were in this spiral where I was using credit cards to keep up. And I actually remember the day I took a cash advance check to the bank to actually have enough money in my account to pay my mortgage on one of the investment properties. And you can imagine, Jason, it was like a downward spiral from there. And when I say we lost nearly every penny, I remember the day my cell phone got shut off. And I had a business at the time and I had a merchant account. So I remember using, even if I should say this on a podcast, but I used my own merchant account to run a credit card of my own so that I would have enough money in my account to turn my phone back on. Like, that's how bad it got.

Yeah, that's. That's something. So you went through a really tough time. Yes, it's. You know, the old saying I always like to think of is everybody's a genius in a bull market. And, you know, you can get away with that stuff for a while, like, you know, buying houses on credit cards or, you know, sort of financing your life when everything's going up, but eventually things correct and what goes up must come down, right?

Yeah. And when we had that success or initial success because of the market conditions, I mean, we're talking for. I was 28 years old at the time, and I was seeing these, these profits on sales of $100,000, $120,000. And so I'm thinking, wow, like, so naturally, when you do one now you the next one I want to leverage even more. And that behavior, it's just not fundamentally sound behavior. And at the time, I remember the thinking for all of us at the time, because I know there was a lot of very smart people who got burned or burned themselves. And the thinking was, well, when the market starts to shift, we can always sell. And what unfortunately happened, as you know, is the market shifted so quickly that there was no way to sell these properties and get out from under them without taking massive losses. And being several hundred thousand dollars underwater, I never even imagined that worst case scenario, I thought, well, I'll just sell if soften up. And unfortunately, so highly levered, you couldn't.

Do it when the market disappears. And it can disappear rather quickly. Now, granted, it did not disappear nearly as quickly as the stock market evaporated and other markets, but real estate certainly got hurt a lot faster. And you were buying like high rise condos or what were you buying?

Our investment market at the time was Daytona beach, and we bought the first property was a Two bedroom, two bath oceanfront condo that we were planning to rent, sort of like on what. Then there was no Airbnb. Then the online vacation rental business was just kind of starting and so we were going to do that. And unfortunately I didn't read my condominium bylaws that said you can't rent short term. So the association forced me to go long term. And then we bought another two bedroom condo. And then the deal that actually broke the camel's back, if you will, was sight unseen. I purchased a $500,000 four bedroom, three bath house with 5% down. And I asked the seller to give me $15,000 in closing costs so that I would have to come up with even less cash.

Right, right. Yeah.

That property rented. Get this, Jason, the market rent on that $500,000 property was thirteen hundred and fifty dollars. And somehow Sean thought that was a good deal.

Isn't that funny? Well, Sean, I wish you would have met me sooner.

You and me both, man. Like I still say this to this day, I had the right, like I was in the right industry, like I had the right asset. My philosophy was, was flawed. And certainly the type of property I was buying and the area I was buying was flawed.

Right, right. Yeah. No, I understand. And you know, it takes a lot to come on a show like this and share that with the audience. So thank you. I really want to honor you for doing that because what we're all about is, you know, having our listeners learn from my mistakes, having them learn from mistakes and experiences of other people. And it's really great that you're doing that. So thank you for sharing that. Now, you were not a real estate agent at that point, were you, Sean?

I was actually. I just wasn't making any sales. Okay, got it. As you read in my bio, so I got my license in 2004. We started acquiring a lot of these properties in 2005 and 6. I remember it was about August, September, right around this time of year 2006, that in that part of the market or in the country, the market tanked pretty quick. And so I was an agent. But my thought was I was going to be the next. I was going to own everything on that island. Right. So I just kept buying. And I wasn't focused on my real estate business until after we got. I remember sitting in front of the bankruptcy judge and the judge saying, you better figure out a way to bring in some income, Mr. Carroll. And that's when I really decided to double down and learn the real estate business and figure out what market could I carve out as a realtor to really generate sales in the market conditions that we had? And that's how I got into the short sale specialty that you mentioned in my bio.

Yeah, and that was a good idea. The market definitely needed that. It's interesting how I changed my view of that, because I remember in the 90s, in the mid-90s, when I was a traditional real estate agent in Orange County, California, and I was doing short sales for other clients, and, you know, I really, you know, didn't like that. I just saw these people who had lived in their homes for a year or two years. They were living there for free. For free. They hadn't made a payment in a year or two. And then they stayed there even longer while their house was on the market. And after I listed it, and then the lender would reduce the loan balance. I remember, I think on one of mine, the lender reduced the loan balance by like $70,000. And I remember I had a couple of properties and, you know, I was in Orange County. I didn't know any better back then. I thought I was an investor. I was really just a speculator. And, you know, they didn't really make sense the day I bought them. So I was kind of carrying them and I was, like, suffering. And here these people were getting off the hook, and it really bugged me, you know. But then kind of one of the seminal moments was I was talking to a guy that I actually interviewed on my show. He said, look, Jason, you got to stop having such an issue with this. The deal everybody signs up for when they get a mortgage is this deal. Here it is. The deal is, I will pay the loan or I will return the collateral to you, one or the other. Some people opt to just give them the collateral. It wasn't true really, in the 90s as much, but, boy, it sure was true in the Great recession in the 2000s, when the banks, they were the ones. Well, the whole. Not just the banks, but the whole cartel, the whole system was responsible for inflating the asset prices in general. And, you know, I interviewed the guy who wrote the article for Rolling Stone magazine about Goldman Sachs, and it was called the Great Bubble Machine. He was on this podcast before, and it's just amazing how the system does that. And I swear, you know, we can get as conspiratorial as anybody wants, but they basically do it to inflate asset values and let all of us little people pay for that inflation of those values as things run up where they just Run beyond the point of common sense. And then they go and take them back through foreclosure or repossession after that. And then they've dinged up everybody's credit score. And then they charge people higher interest rates during the recovery period.

It's a vicious cycle.

And then they run it up again. Yeah, it's such a scam. And when you see this, when you back up from the picture of history, you know, you back up and you stop looking at the brushstrokes on the painting and you start looking at the whole painting, the big picture, the forest rather than through the trees. Right. You see that they do this over and over. It's like every 10 years it's the same story. Now, sometimes it's more or less pronounced than it is other times, but it's the same basic deal. Incredible.

Sure, for sure. And to your point, this was a tough, emotional time. Not just because we were losing a lot of money, but I remember really battling with my own conscience about my own properties and negotiating with the banks. And, you know, because I'm thinking, well, I agreed to pay this money back. And it never dawned on me that in the case of a real estate loan especially, you know, that is the deal is that, hey, you're lending on this asset and it's a business transaction. And so I had to shift my mindset that this is a business transaction. This is not about my character anymore. Like, yes, I did some stupid stuff.

Was it really that stupid in the context of the environment at the time? I mean, every. Everybody and every action needs to be judged by the context in which it occurs.

That's very true.

Yeah.

I explained my thinking at the time was, well, I can always sell this asset and nobody, even though the loans we were doing and the behavior was probably far more reckless than anything I'd ever do. Again, the deal was, is that okay, well, could anyone, or did I foresee, I'm sure some people did, that I could purchase an asset for $500,000 and a week later it could be worth 250 or $300,000. Because that's exactly what happens.

Well, that's the stay away from condos. And I mean, stay away from. Exactly. High rise condos.

Yeah.

Those are always just so frozen.

Those in cyclical markets especially. I mean, that market was hot, hot, hot. And then it just froze. And the first place we bought, the gentleman that bought it from us when we sold it still lives there. What he paid for it. And this was he. We sold it to him in 2006. This was. That one actually worked. He still is $70,000 underwater from what he paid for us in 2006. So. And he's living there, so he probably doesn't care because he can afford the mortgage apparently. But I just like, wow, he. We're talking.

You're saddled. You're saddled with such high HOA fees and those deals are just too risky. There's too much control that someone else has over you. So, okay, so you learned that lesson. Good. Thank you for sharing it all. And then you got on the train of the short term rental properties, or, sorry, the long term rental properties. This sort of sensible, you know, bread and butter, boring single family homes. When did you start listening to my podcast, Sean?

I think it was around 2013, Jason, because I know it was around then because we were still paying back on our bankruptcy settlement.

I remember listening to you going, gosh, I'd love to do this, but I can't get any mortgages right now. I remember listening to you on the treadmill going, this makes so much more sense. I just remember thinking, I can't wait until we pay off this bankruptcy so that we can once again start investing. Because at the time, all of our focus was just pay that debt to back.

Right, right, right. And when you say you were on the treadmill, you were literally on the treadmill at the gym, right?

I was, I was. And I was actually, I was living in Scottsdale, Arizona at the time. I remember I was at the UFit gym right there on Scottsdale, whatever it is, Scottsdale Road. And listening to you explain this concept of buy, you know, properties that make sense the day you buy them. And I thought, yeah, that's what I. That makes a lot more sense than what I was trying to do.

Right, exactly, exactly. So, Sean, you got into the traditional long term buy and hold rentals. You had some challenges there. You overcame them, and you are really a very tenacious person. I feel that I'm that way. And, you know, I thank my mother for instilling it into me. You know, I would always hear her wagging her finger at me when I was a kid, saying exactly this, Jason, finish the job. Finish the job. And, you know, so that kind of stuck with me. And I've always been a sort of finish the job believer. What makes you so persistent, Shawn? What in your character has got you thinking that you just need to kind of stick with things through thick and thin?

I think some of it was my upbringing as well, like my father. Just, you know, no matter what show up? And I just watched him. And, you know, that was a message that I received loud and clear. Some of it, frankly, Jason, is stubbornness. And I actually just did a video the other day about as I'm revisiting this idea of quitting. And sometimes I think I would be better served to quit some things that are not helping me in the big picture of life.

You know, like, that's a fair statement. Yeah. You know, being too persistent can actually be a liability for sure.

Yeah. Like sometimes you need to sell something or release a property or. And in this case, you know what it was. I just believe, when I believe in the big picture, I can be incredibly patient. Like, so I really believe with every cell in my body in the model of buying holding solid residential real estate. So I know that. I just know it to be so true that in those moments where I have those emotional reactions. And Sarah, my investment counselor, can tell you on our voxer chats, there are plenty of times in the past where I said, that's it, Sarah. I'm selling it all. And she' say, okay, well, you know, you're feeling that way right now at this moment. You know, like, okay, like, you can do that, or, you know, you're having a tough day right now with the property, and this will pass, and next month the rent will come in. And so I just know through experience, I've learned enough about the model too, in this case to just hang in there. And I know that, you know, the phrase that runs through my mind is, this too shall pass. And in my acting career, it's the same way. Like, I truly believe that I. I've known this for a lot of years, even when I wasn't in the business. I truly believe that I have what it take to win in this industry. And so when I have that conviction or that belief, and there's a lot, and the evidence is there to support it, I will never quit that thing unless you're going to have to chase me out of it. But to your point, sometimes there have been plenty of moments, whether it be with stocks or businesses I was involved in or relationships I was involved in, where it's like, I'm going to stick it out and then I end up hurting myself more in the process. So I think becoming aware of the differences where I'm at right now in my life, like, just paying closer attention. But real estate, I'm not going anywhere. In fact, I'm looking to explore, expand my portfolio still, even with all the challenges and I've had Challenges is a soft way to put it. For sure. It's been there was some downright miserable.

I heard someone say, I was at a conference and I heard him say, you know, stop calling things problems. Call them challenges, because it makes you greet it with, you know, a different perspective. Right. You greet it with, hey, this is a challenge. I'm just going to deal with it and overcome it. You know, if you call it a problem, it's like, oh, it's a problem. You know, so. Yeah. And I mean, certainly like in your acting career, I mean, talk about a rejection business, right?

You know, much. Yeah, yeah, it's. You know what's frustrating too, sometimes as an actor is we don't always. We seldom get feedback as to why we didn't book the job. Every once in a while, you'll get someone that'll give you that feedback where they'll say, hey, you know, we went with somebody because of this. And almost always the reason I don't book a job or any actor doesn't book a job has nothing to do with how talented you are, are. So that can be incredibly frustrating where you just keep showing up, showing up, showing up, and you don't even really know what's going on behind the scenes.

At least with real estate, the market and the behavior of the properties, the performance of the properties, I'm at least getting feedback so that I can course correct a little easier. With acting, it's a little different. That's why I hire coaches in acting, because they can see things in what I'm doing that I can't see. Come to think of it, now that I'm saying it out loud, that's kind of the role Sarah plays as an investment counselor for me, is she can objectively look at something that I'm right in the middle of and kind of call balls and strikes, to use a baseball term, instead of. She's not emotional when she's giving me suggestions or advice, whereas when I'm in it, it's a lot harder to see.

Sure, yeah, that's definitely true. Now, last year, you and Tonya, your wife, came to our Venture Alliance Mastermind meeting in New York City. Of course, you live there, and it was great that you guys could attend that. You know, tell us a little bit more about, like, having a coach and constantly educating yourself. And you, you seem like you're very engaged in wanting to learn more and, you know, be coached. I mean, some people aren't coachable. Right? That's true. But you're the kind of the opposite Tell us about that.

Well, going back to the challenges I had back in the Great Recession, looking back on that now, I am so grateful for having gone through all of that, because that's where I learned so much about what shapes the decisions I make today and what I learned. Probably the biggest takeaway that I had from that period in my life was how I don't have all the answers in life. I'm not omnipotent. I am not the expert on everything. And when there's an area. That's how I built my real estate business back then was I sought out someone. I was desperate, and I sought out someone who was doing really well. And that person, without charging me any money, just took me under their wing and taught me not only how to do that business, but how to study, how to learn in business, how to look at someone who is successful and not copy what they're doing, but look at the principles they're using. That's where I learned all of that and that I got so excited by the results I was getting back then that it just stuck. And I started going to more conferences and I started to invest in myself. And now, looking at that, maybe almost 15 years later, I still do that. The difference now is that, as I've seen especially the coaching industry blow up into what it is now, I'm just much more careful in who I take advice from, because one thing I've learned is that I want to learn from people who are actually doing the thing that I'm trying to do versus, you know, everybody's got an opinion on something. Right. But I just love. And I love. I love the feeling that I get when I see myself, like, I kind of look at myself growing and I look at, you know, I journal a lot, Jason, so I'm able to go back and read what was on my mind three years ago. And it gives me a good sense of fulfillment to see that growth. And so it just fuels me to do it more, you know, every single day.

Yeah, that's really good. That's really good. Well, hey, Sean, we got to wrap it up. You know, are there any tools or apps or tips that you want to share with our investors? You know, things that have just helped you? We talked a lot about Mindset, but are there any specific, you know, apps, tools, technologies, or just organizational techniques or anything you want to share like that?

Yeah, I've got a couple quick ones. First of all, and this is not just because it's your software, but I highly recommend the property tracker tool if you're not using property tracker, use something where you can look at the actual real numbers of what your assets, what your portfolio is doing. Because in, in those moments where you have days like I had, one of the things that kept me on track was to go back and look at the actual performance of the property and that includes the full performance of the property. So property tracker is one a general tip would be in any market that you're in, even if you are more of a hands off investor and you're choosing to go the route of property managers and kind of letting them do most of the heavy lifting. What I would say about that is in every market that you're in and one job that I think every investor should do is to have on standby, like whether it's a contractor, a handyman, someone on the ground there in that market who you can build a relationship with multiple people. Because property managers, while some of them are good, you will suck, you will overpay and get, you know, I mean I just had a job in one of my properties that the estimates coming from the manager were 4,000, $5,000. My licensed contractor that I met through a referral did the same job for under $2,000. So we're talking about unbelievable savings.

Yeah, it's just ridiculous. And by the way, we didn't even get to talk about that. But you know, self management, you're now self managing I think all of your properties or just some of them.

Just some of them. And I take what's called a hybrid approach. Like I'm on a lower scale of the, like one of the managers I have, like there's different pricing depending upon how much you do. So I do more for some of those and so I pay way less in fees. They handle some of the, you know, the day to day stuff. But like in terms of if there's repairs, I'm doing more of that. And as I expand my portfolio, especially as I'm looking at some new construction stuff that hopefully will have some less maintenance, I'm looking at self managing those just because I anticipate that those are going to be a lot easier to run. But yeah, it saved me a ton to get on the phone. Even though I'm a busy guy, like all of us, that half hour or one hour that I spend getting estimates on my own or making a few phone calls is well worth the 2,500 or $3,000 I would save, you know, in some of those, those maintenance jobs. So I go back and forth with it sometimes. Jason, I don't want to deal with it and I just, I don't want the phone to ring. But then when I see sometimes the savings I go, well. And the speed too. Speed is the other thing. Like my handyman was in there in 48 hours and had the job done.

Yeah, you really do. When you self manage I think you just provide a better service, a better experience for your tenants, you know.

I agree. Yeah, she was very happy and she, she was very cooperative with him. They were texting back and forth. I didn't even have to get involved once I called him and gave him her information and let her know that he was going to be in touch. The two of them worked it all out and I got sent pictures and I almost was surprised at how easy it was.

Yeah, right. And a lot of times the tenants, they just do a lot of your work for you. You know, they coordinate appointments. I mean I've had tenants in my self managed properties where they're calling around getting estimates for me. They'll say, and I've shared this, some of this stuff on the show over the years where they all say, you know, this one guy came over and I just thought the guy was overpriced and not that good. So I'm gonna call around and find some other people for us. You know, they view it like you're on the same team, you know, not like your opponents. And the property managers always set it up like your opponents. I mean the tenants, they just want a nice place to live. You know, I think you can give it to them better if you self manage and deal with them directly. It's just a lot easier than people think. But you do have to have a local contractor, some local contacts and we can help you do that on the show and you know, at our events, network with our other clients and stuff who are doing it. So. So yeah, good stuff. Sean, any other apps or tools or.

Technology, I mean this is going to sound really basic, but using the Google suite of products, especially Google Docs, where like if my wife and I, or if you have business partners or anybody else that you're investing with, or in the case of my contractor, being able to share in real time on the web in a folder that we can all see what's going on with the repair, what's going on with the property and what I love about those is they're absolutely free. So you can use the Google spreadsheets, you can use the Google document where you can have a running document. And it also keeps me in control of seeing who was in there when, like, it gives a lot of accountability. And again, it sounds so simple because it's not like this hot new real estate. Yeah. I get saved me so many times from just being able to go in there. When I'm on my phone waiting for a train, I can go into the Google suite and, you know, see that my contractor uploaded a photo of what needs to be done. You can keep it really simple like that. I'm sure there's some tools out there. But that has saved me so much time.

Yeah, absolutely. Good stuff. Well, Sean, thank you so much for sharing your experiences. And you know, this is. It's almost like a rags to riches story here. We're hearing from you kind of.

Yeah, yeah. I still feel like I'm on the path for sure and there's a lot more wealth that I want to grow and things I want to do. But I'll tell you, it's. When I think back to where we were and what both of us, my wife and I both have done to be where we are today, it almost like if you'd have told me this is where we were headed 10 years ago or what, I would have told you you were nuts. Because I could not. I couldn't have imagined we'd ever be able to buy real estate again or that I'd ever want to, you know, here we are with. With several properties later and we're still. We're still chugging along.

Good for you. Thank you so much for joining us today and happy investing. I will talk to you later.

Thanks, Jason.

Thank you so much for listening. Please be sure to subscribe so that you don't miss any episodes. Be sure to check out this show's specific website and our general website, hartmanmedia.com for appropriate disclaimers and terms of service. Remember that guest opinions are their own, and if you require specific legal or tax advice or advice in any other specialized area, please consult an appropriate professional. And we also very much appreciate you reviewing the show. Please go to itunes or Stitcher Radio or whatever platform you're using and write a review for the show. We would very much appreciate that. And be sure to make it official and subscribe so you do not miss any episodes. We look forward to seeing you on the next episode.