Scaling Up: From Rock Bottom To Real Estate Success With David Olds

Join us for a riveting episode as David Olds, host of The David Olds Podcast, shares his transformative journey from a modest start in real estate to becoming a successful investor. David recounts his early days in Boston, his unexpected entry into the real estate market, and the challenges he faced during the 2008 housing crisis. Discover how sheer determination, a bit of desperation, and creative problem-solving led him to success in Chattanooga. This episode is packed with candid stories, practical insights, and the gritty realities of building a real estate empire from scratch. Tune in for an inspiring tale of perseverance and innovation in the face of adversity!

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Scaling Up: From Rock Bottom To Real Estate Success With David Olds

This is the show where we talk about how you can live your vision and love your life. Our guest is going to do exactly that in a way that helps you run your real estate business without having to deal with the transaction coordination on the end. His name is David Olds, but before I bring him on, I wanted to mention how much I appreciate you for coming back to tune in to our show. Anything you can do to share it, like it, give us five-star reviews on whatever platform you’re finding us on, or if you’re going to TheGenerationsOfWealth.com and follow us there, that’s fantastic.

Also, if you’re looking for a place to build your network and take your business and your life to the next level, we are looking for a few qualified people to join the Circle of Trust. The mastermind that I host and run. If that’s something of interest to you, go to REICOT.com, and answer a few quick questions. We’ll jump on a call and we’ll see if it’s a fit. Now, onto the show.

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Mr. David Olds, I can’t tell you how much I appreciate you coming on the show. If you wouldn’t mind, give everybody a little bit of background about who you are. We met not too long ago, but you have your own podcast, which is the David Olds Podcast. I was a guest on your show. I am happy to have you on the show. Tell us a little bit about yourself.

Thanks for having me. I don’t feel like I’ve got this super crazy story. I wasn’t on drugs. I always said that if I could do maybe a little cocaine or meth, it would thin me right out. I’d be as skinny as you, but getting off of it would be the problem. That’s always going to be the issue. I fell backward into real estate a little bit. Growing up in Boston, my parents were big house fixers. They own their house. They were doing remodeling and stuff on their own house, working in the yard, and doing that stuff, which as a kid, you hated.

The one thing I would always say was, “When I grow up, I’m not going to make my kids do any of this stuff.” It’s because we had an acre almost on the New Hampshire border. It feels like all you do is ever rake leaves. I hated it. My dad put an addition on and I’m hanging drywall. I was miserable about all of those things. What do most of us do? We grew up and became our parents.

David Olds’ Journey Into Real Estate Investing

I got married in 2002 to my wife at the time and we bought a house. What’s the first thing we did? We tore out the carpet and put it in laminate. We took out a slider and we put in French doors. We did all the things to update it because I was working for a home improvement company, it was Scotty’s Hardware, but very similar to Home Depot at the time.

I sold that two years later and made $50,000. I was like, “This is great.” I didn’t have to pay taxes on it because I had lived in the property and it was homesteaded. I thought to myself, “This is cool. Let’s do this again.” I did it again. I did this to another house. We bought an ugly house in a beautiful neighborhood and sold that one about 30 months later and made almost $100,000. I’m like, “I need to figure this out.”

I remember I was at the airport waiting for someone to come in, leaning in the bookstore on the shelf, flipping through books, and came across the most cliché thing ever, Rich Dad Poor Dad. Almost every investor started the same way, so I’m reading that. I’m like, “This is a great book. This makes perfect sense to me.” That was how I got started. At the very end of the book, Kiyosaki says, “Go find a real estate meetup or REIA,” or something like that. I found one in Orlando and got super involved. This was back before YouTube and great podcasts like this. All the ways that we could get information back then were the REIA or a book that you’d buy at the library. That was how you learned about real estate.

I got involved there. I went to all the classes. I bought mentoring and coaching. I did everything I could. My wife and I both still worked full-time jobs then. The only thing that we could do was keep buying and selling houses and fixing them up. We’d not only buy one to live in, but we’d buy one to go ahead, fix up, and resell. We did that through the next maybe 3, 4, or 5 years until 2008. The market is starting to slow down.

Adapting Strategies And Overcoming Challenges

We didn’t know it was going to crash like it crashed but we felt that there was a little bit of a slowdown coming. I bought my last house in Deltona, Florida. Let me tell you about this house. It’s a three-bedroom two-bath brick ranch house in central Florida. They’re all the same. On the day I bought it, it was a probate deal. I got it for $97,000. Let me ask you if you think this is a good deal. I bought it for $97,000. One block over two blocks down, an identical house, with a left-hand garage and everything. An Identical house was sold for $214,000.

For $97,000, you’re like, “That’s a deal.” I bought it in maybe August and we knew we were going to move someplace. We’d been looking at other cities. We wanted to invest in other cities, and then we decided we were going to move, which was Chattanooga, Tennessee. This is our last deal. It’s like musical chairs. It’s the last chair we’re going to sit in. We’re going to make some money, and we’re going to get out of town.

We closed on it in August. We were fixing it up. Back then, I was younger, with more energy, and skinnier. I was scraping the seal and putting down the tile. I made my kitchen cabinets. I put them together out of the box. I made my own countertops. I did all the things. I finished it in early November, and I called my realtor Shayna. I’m like, “I’m all done with this house.” She’s like, “Great, but it’s the holidays. Nobody buys a house. I don’t want to list it and get you a bunch of days on the market. Let’s list it in January.”

I’m like, “Perfect. No problem.” She comes over on January 2nd or 3rd. She walks in and she’s like, “You did a great job.” I’m like, “I know.” She’s like, “It looks beautiful.” I’m like, “I know. It’s great.” I said, “What do you think we could sell it for?” She sits down. This was 2009. Facebook barely is invented. She flips open this notebook with lots of pages. She was flipping back and forth. “This one is sold for this.” I’m like, “What can we sell it for?” She’s like, “Probably $147,000.”

I’m like, “Wait a minute. One block over was $214,000.” “Yeah. That was six months ago.” That was pretty hard to accept. At the time, I consider myself a new investor. I’d probably only done 12 or 14 deals. I’m like, “Shayna, my house is nicer. My house is better. Those were foreclosures. You could see the pictures. People had abandoned them in the middle of the night and they were selling for $120,000 or $130,000.” She’s like, “Yeah, but that’s what’s on the market right now.”

I was shell shock sitting there. $50,000 had gone. All those houses I’ve been remodeling, we put them on the market and they’d sell easily within 30 days. This was a new little conundrum. I’m like, “I’d already given my job notice.” I was planning on leaving in six months one way or the other. I thought I was the most magnanimous SOB that’s ever watched the face of the earth. I’m like, “I’ll do it for $155,000. I can have $50,000 in my pocket, I can live with that.”

She’s like, “Okay.” I’m like, “Do you think that’ll do it?” She’s like, “I don’t know,” because she was a listing agent. They don’t care. They want to put their sign in the yard and out they go. $155,000, $154,000, or whatever it was. There was not a single call in the month of January. At the time, I had teenage boys. I don’t know if you’ve ever sold a house where you got kids or you’re cleaning the house. Every day it has to be clean because you think that’s the day someone is going to come by and look at your house. There was nothing.

In February, I’m like, “What should we do?” We’re not nervous yet, but I’m like, “This is out of the ordinary.” She’s like, “You need to lower the price.” I’m like, “Do you think $147,000 is a number?” “No.” I’m like, “What do you mean?” You told me $147,000 was a number.” “Yeah. That was last month.” I’m like, “What should it be now?” She’s like, “I don’t know. Maybe $139,000.” This is how fast the market was falling. I’m like, “No. I’ll do $147,000 and that will get it because my house is fully remodeled. It’s beautiful.” Another month. There were a couple of calls, but not even a showing. Now, I’m at the end of February and I’ve told my job I’m leaving. I’m like, “This is crazy.”

I called her back in March and I’m like, “I got to sell this house. What do we have to do?” She’s like, “If you want to sell it, probably $125,000.” I’m like, “I’m not going to make any money by the time this is done. I’m going to make nothing. I can’t do that. That’s dumb.” Also because I had been to all the REIAs, gone to classes, and done all the things, I’m like, “I can sell this on owner financing. I’ll do a lease option.” I went out. I bought a bunch of signs. I hand-wrote them, “No banks needed. The owner will finance. $5,000 down.”

I put out a bunch of those signs and still, it was a struggle. Finally, in May, I found a person who I liked. This is a nurse who had a job but couldn’t qualify for a loan. She gave me $5,000 down. I was leasing it to her. I was making $12 cash. That was how we left Florida to come to Tennessee with $5,000. It was me, my wife, our two boys, three fat dogs, and my brother because he was going to come up and work with us. He’s eleven years younger than me.

That’s how he came to Tennessee. I had been going back and forth. My brother was staying up here. We had bought one duplex sub-to by taking over a mortgage. We were getting ready to buy this other house. You probably bought a lot of houses and sometimes when you walk through one and you haven’t seen it for 1.5 months or 2 months, your memory gets a little fuzzy of what that house was because you look at so many.

I hadn’t seen this house in six weeks. It was in East Lake, an area of Chattanooga, which is not the best area. Even when I contracted, I didn’t think that was where I was going to move. It worked out that it was the house that we had so that was where we were going to move up to. We drive 577 miles in two cars, a moving van, kids, dogs, and the whole thing. It’s a horrendous day.

We get to Chattanooga in time to go to the title company and pay for the closing out of my $5,000. That’s what I’ve got because my wife had been laid off months before. We go to this house. I pull in and I’m like, “What a shithole. This place is bad.” It had been empty for probably a year because the guy we bought it from got married. That’s why he didn’t need two houses. It’s on the side of Missionary Ridge, the floors were a little uneven. It was a 1900s house with no air conditioning.

One of the poles was out so half the electricity wasn’t working. One of the doors didn’t close tight so there’s a mouse running through. It was terrible. Everybody is exhausted and cranky. Everything we could do was pull two mattresses out of the truck and throw them on the ground with an oscillating fan. I’m going to tell you, I laid there that night and I’m like, “What on earth have I done?”

I could have found another job in Florida. I had this great house that we had remodeled in a beautiful neighborhood and I left all of that to come to Chattanooga to do real estate and I’m in this house. I cried myself to sleep that night. It was the worst thing ever. I’m like, “What a terrible husband, father, all the things.” I was like, “How do you uproot your family and come to this place and with this terrible house?” I remember I’ve never felt so low in my life. I was like, “What a horrible decision I’ve made.”

Did you say that was August?

June was when we moved. I bought it in August. It took me until May of the next year to sell it and then it was June, which is hot.

You’re in a house with no air conditioning and a fan in June. I was in Tennessee a few weeks ago in June and it was miserable. You were a terrible husband and father for sure.

I’m going to tell you, I was. I’ve never claimed to be the best guy, but this is like, “What am I doing? This is stupid.” You wake up the next day though and I’m like, “We’re going to figure this out. I’m going to go get some blank bandit signs. I’m going to go put out signs and say we buy houses. I’m going to figure this out. There’s going to be a way. You have to make money. You have a wife, two boys, and three fat dogs. There has to be a way to do this. I look back at it now and I see those memes on Facebook like, “Burn the boats. Burn the bridge behind you,” and I’m like, “Don’t do that if you have a family and kids.” It’s dumb. It’s incredibly dangerous and irresponsible. Luckily, it worked out for us, but it could have gone horribly wrong too.

There’s something to be said for having your back against the wall. You had no option then to succeed versus people who are comfortable, “Maybe I’ll work today. Maybe I won’t work today on my real estate business.” You didn’t have a choice. I had the same struggles when 2007 kicked my ass and took our entire portfolio. It was the same thing.

What was interesting is when I was in Orlando, I took a bunch of wholesaling classes and people laugh when I tell them this now. They don’t believe it. I couldn’t make wholesaling work in Florida, which is crazy because there are so many buyers, but it was because I had a job making $90,000 a year back then. My wife had a job probably making $45,000 or $50,000. We were good plus we were flipping a couple of houses a year. We didn’t have to make it work, whereas up here and now, I’ve wholesaled probably 1,500 to 1,600 houses. When we got here, I had to find a way to make it work. There was no other option.

I attribute a lot of our success to sheer desperation and being too dumb to quit. I know that this works. I’ve seen a million people wholesale. I’ve seen the checks. I know that the process works. I have to believe in that enough and I’m desperate. My kids want new shoes to go to school in September and my wife surely likes to have some food to cook. That first summer was a little bit tough.

To replace $140,000 of income takes a lot of wholesaling back then.

They were $5,000, $6,000, or $8,000 deals.

That’s what I was going to say. We weren’t cutting $50,000 wholesale checks back in 2008 and 2009.

No. I remember some people would talk about a $20,000 check. You would double close. It was huge back then. In our first year, we ended up doing almost 30 deals in the first full calendar year. We came out the gate hustling but I think our average was 5,400 or 5,600. It wasn’t a ton. We had to do a lot of deals. The thing that made us successful is real estate was the first thing I thought about in the morning when I woke up. It was the only thing I did during the day and it was the last thing I thought about when I went to bed.

We did some family stuff on the weekends. I took the kids hiking and swimming in the rivers and things because we were too broke to go to any amusement parks. Every single Friday night, we went out and put out at least 100 bandit signs. During the week, it was driving for dollars. My wife was sending out handwritten postcards because we couldn’t afford to buy postage from anybody. It was handwritten yellow letters. We bootstrapped this thing from nothing and wielded it into existence.

This is amazing because that’s what probably built camaraderie and the bond with you, your kids, and your wife. There is stress and probably some shouting once in a while but it is true. My seventeen-year-old daughter hand-writes our letters right now. She wants to be involved in a business. I said, “That’s great. You start in a mail room.” That’s how it goes. You don’t go to the top of the food chain because you have the same last name. It doesn’t work that way.

Building Bonds And Wealth

One of my kids, when we were rehabbing, loved tearing stuff apart and helping me do the physical stuff. The other one wanted no real part of it. He wanted to be playing on his little Game Boy and stuff. That’s how we got started. Originally, when we had the idea of coming to Chattanooga, we wanted to buy multifamilies and apartments like everybody else but if you go back, banks were not lending money. Nobody was lending money. They were very interested in taking properties back. That was their thing. Getting the properties they took back off the books.

I couldn’t use banks. Also, I couldn’t rehab anymore because what do you do with a rehab house? You sell it to an end buyer. Nobody was buying. Obama had to do the $8,000 credit to get people to start buying houses again. That wasn’t an option. I’m like, “We’ll wholesale. We’ll do this.” Even within our wholesaling business, we’re going out and we’re talking to people. I would come to you and let’s say you had this house and you wanted $80,000, but my cash offer is $60,000 because that’s how things were back then.

We did some sub-to deals. If I knew what I knew now or I knew where the market was going to go out, I would have bought 1,000 sub-tos. I was never worried about buying negative equity. That didn’t bother me too much or being at zero equity but I always wanted to make sure that it would cashflow or that I was sure I could get the thing to cashflow. I’m going out and talking to people. They want $80,000 and I want to offer them $60,000. They’re like, “But my mortgage is $75,000,” so they couldn’t take those offers. That was frustrating. I was going out to a lot of appointments where that was happening.

One day, it hit me because every so often I’d come across somebody who owns something free and clear. I’m like, “If they could all be free and clear, that’d be great. They may not like my offer, but at least they could accept it.” I remembered way back in the day in Orlando when I was at one of the million marketing courses or whatever I went through. They talked about the percentage of houses that are owned free and clear in the United States. Do you have any idea what the percentage is? Most people don’t.

At that time, it was probably close to 50% to 60%.

It’s been pretty steady for the last twenty years. It’s anywhere between 38% and 42%. It’s been very consistent. You guess higher than most people. I’m like, “40%. That’s a lot of people. Why don’t I do mailings to those people?” We’re still putting out bandit signs. We’re going to get some other stuff but like, “Why don’t I mail to those people?” It’s because I’m getting tired of being rejected. I feel like I’m wasting my time. That’s what we did. We started pulling free and clear lists.

The number’s still the same. I looked it up. First American keeps great stats on this. I started talking to more people who own their properties free and clear, which is a lot of landlords. I’d go out and I’d talk to them like, “I know you want $80,000 but I’ve got $60, 000.” My closing percentage went up. Naturally, people could accept what I was offering but then I started thinking about a little bit more. If you’re a good negotiator and I know you are, 1 out of 10 is good.

If you talk to 10 people and you get 1, you’re a freaking rockstar. One out of eight, you are in the Hall of Fame. That’s great, 1 out of 10 but my brain goes, “What about the other nine?” I know it’s great, but still, what about the other nine? I started asking the question. I would make my offer, especially when I knew it was free and clear and landlords. I love to do this with landlords. I’d be like, “Are you sure, Derek?” It’s a cash offer. It’s what your house qualifies for all those things. “Okay, I can’t do that. I like to buy these for cash. I buy them and be done with it but let me ask you a question. Do you need all the money at once?”

Once I figured that out, the long delay was because I was too nervous to ask. Imagine asking your first girl out. It takes a while to get it out but I realized that having that long delay and it being the first time I’d ever thought about it, it helped me build a lot of rapport. Sometimes they would say yes, sometimes they would say no but what it did was it gave me another bite at the apple on those nine because you know if it’s free and clear before you go over there.

There was a ton more to how we’d position the conversation, especially if it was a landlord. What started happening is, “I don’t know. What are you thinking?” That opened up a ton of doors and that’s how we bought over 100 properties in five years all with owner financing. How we created our real wealth was that way of doing those deals. My positioning because I was about 40 at the time. I remember always growing up in my life the whole time, “I’m going to retire when I’m 50.” Now, I’m 52. Still have not retired but my thought process was how do I get to the end as quickly as I can? That came from a great mentor of mine who taught us that.

Every time I looked at these properties, because I had a good wholesaling business where we were making $100,000, $200,000, or $300,000 a year over time or we got up to those amounts, I didn’t necessarily need the cashflow. For the people who are tuning in, when you’re working out on an owner carry or owner finance deal with a seller, you can make whatever terms you want. It doesn’t have to be 30 years. It doesn’t have to be 8%. It could be 1% for five years. It’s whatever term you two agree to.

What I was trying to do is I’m like, “I wanted to retire when I was 50 so I wanted everything paid off.” I’m like, “That’s not realistic.” Some of these deals are cashflow positive. Twenty was the shortest I could shrink them down to. Some were 5, 10, and 12. There was a variety but the most I would ever go, if I couldn’t make it work in a twenty-year term, I was not going to buy it because I wanted to be done for sure by the time I was 60.

What happened is over these years, sometimes it was one property or sometimes it was ten properties. One time, it was 27 doors that I bought for almost $1.1 million but I was able to make a deal where it was zero down $1.125 million, or something like that, a 4% interest rate. I put it on a seventeen-year term. Why? It’s because I was 43 at the time. I refused to go past age 60 because I didn’t want to be doing houses and fixing toilets and water heaters until I was 70. That was how I approached all these things. There’s a horizon. I’ve got a definite end date. I want to get these things done. If I can squeeze, compress, and accelerate the amortization enough, then I will buy this deal. We got good at buying those types of deals.

Revisiting Seller Financing Deals

Do you ever go back after you have the seller financing transactions and try for a second bite at the apple?

Yeah.

Can you talk about that? The people who know me know that I do that, but let’s talk about that a little bit.

The thing that I do regret is that I sold a bunch of these properties over the years. I had this one in North Chattanooga, which is an expensive area. I bought this property for $25,000 or $30,0000 maybe. I don’t even remember what it was. I bought it for something ridiculously cheap. It was close to being paid off. It was maybe a 10 or 12-year term. I had a tenant in it the whole time, and she finally moved out and it was a wreck. At that time, I did not have the money to put in $100,000 because now it had to be remodeled nicely.

I went ahead and put it on the market and it sold for $147,000 to $149,000. It’s in my course. I can’t remember. I was going to walk with $120,000. I remember the girl’s name was Sarah Stanfield or something like that. I’ve got a closing date already and the title company’s like, “I need a payoff.” I’m like, “Great.” I emailed because we didn’t talk. She did everything through email. I’m like, “Good news. I came across a little bit of money. I’d love to be able to cash you out.” Let’s say I owed her $21,000. I’m like, “I got $16,000. I can pay you out right now if you’re interested.”

She almost instantly emails me back and I’ve never had this happen before, “I would love it if you paid me off.” She knew the exact amount like she had the amortization pinned to her wall. “You owe me $22,374.62 and that’s what I’ll be willing to accept.” I’m like, “Okay. Fair enough,” but lots of times we would go back and do that. “I’ve come to a little bit of money. I’d love to pay you off if I could.” It worked all but once. I wasn’t trying to give them a 50% haircut, but if I could take $5,000, $6,000, or $10,000 off depending on how much I owed, fantastic. It’s like a little short sale for owner carry deal.

What people don’t realize is at the time you bought the house, they were emotionally attached to the house. Months or years later, they’re used to getting the payments, but their life might change when the chunk of money makes sense and they take a discount. If they don’t, who cares? You keep making the same payment. You have nothing to lose by asking.

You’re right. That $400, $800, $1,000 a month or whatever you’re paying them, and then all of a sudden you call them and say, “I can give you $48,000.” They’re like, “Oh.” It’s a great strategy.

From Wholesaling To Transaction Coordination

You segue from there and you started your easy REI closings. Talk about that because that’s a big part of your life right now.

What I was doing then was I was wholesaling. We were buying the rentals. As the market shifted in 2014 and 2015, we went back into rehabbing. We did a lot of rehabs over the next couple of years. I had shifted probably to 80% rehabbing and 20% wholesale. I brought in a young kid who graduated from college. He is super smart. His name was Justin. I brought him in and we cranked the wholesaling business back up so that we were dominating Chattanooga.

I had another guy come in who wanted to be a partner, and he had left his job in finance or something. I’m like, “Great.” Now, there are essentially four of us. It was him, Justin, my wife, and me. When you start chopping the pie up in force, it gets to be small. I’m like, “Maybe we’ll start virtual wholesaling,” which wasn’t even a term then. We’re like, “We’ll go to Birmingham,” and some other local cities. That’s how we started our nationwide wholesaling, which eventually got us up to 115 markets across the country.

We were big nationwide wholesalers. I also started doing some coaching mainly on the disposition side. I was very heavy on the second half of the business. I had a partner. Two of them handled the front side, and I handled the back. I got good at finding title companies, solving title problems, and all of the struggles that I see people having. From being in different masterminds, I became the go-to person for solving those kinds of things because when you do something for ten years, you get some experience, even if it’s by accident.

One of the things when we were running our wholesale business that happened. The room I was sitting in was our transaction coordinator’s room. I’m doing a lot of JV deals too. I had a call one day from this guy. His name was Mario. Normally, if you do JV deals with somebody, they’re going to do 2 or 3 deals, and then you’ll never see them again because they’re like, “I got some money now. I’m going to hire my own dispo person.”

Mario is this kid from Alaska, and he was doing deals in Macon, Georgia, which was weird. He called me one day and we were talking. I’m like, “Mario, let me ask a question. We’ve done twelve deals with you or something. Normally, people go off and do their own thing but why do you keep coming back? I enjoy getting half the deal. That’s great.” He’s like, “One, my English isn’t that great.” He was a little nervous on the phone, but you deal with the title company too. I don’t like dealing with them. I don’t like solving all the title issues.”

I’m like, “That’s interesting.” I was at this mastermind and they were talking about all the title issues that people were having because this is when virtual wholesaling exploded. I was down there with probably some of the biggest wholesalers in the country. It dawned on me that there are a lot of services in our industry. Certainly, marketing, bookkeeping, property management, and all those things, but nobody helps people close their deals.

Most coaches are like, “Just find a title company and they’ll do everything for you,” which is not the truth. In the end, it’s the investor who’s chasing down trust documents and death certificates. If you’re doing that, what are you not doing? Talking to sellers, and buyers, and making money. I thought, “If we could find an effective way to do that as a service for people,” because we’re already doing it for our JV partners, “Would that help people? Would that be a benefit? Could we make money doing that?”

I talked to one of my friends, Corey Geary. He is one of the first people to bring out renovations to everybody. He’s like, “That’s the dumbest idea I’ve ever heard.” I’m like, “What do you mean it’s dumb?” He is like, “Transactions are like brain damage.” I’m like, “I know. I think we can help people with that. We’re good at it. I already had a team of coordinators. I was good at it. They’re good at it. I think we could do this. Maybe we could get 10 or 15 clients and we could turn this into a little business.”

It exploded. Now, we have a couple of hundred clients. We have eighteen coordinators in our office here. It keeps growing. We’re interviewing new coordinators every single day to bring them into our team because we realized it is a thing that people need and they don’t love it. Nobody read Rich Dad Poor Dad to get into investing to figure out what a monument of title is. Nobody loves tracking down a mortgage release on a bank that’s gone out of business and all of those things.

Nobody wants to deal with fourteen heirs. Two of them are out of the country and one is in jail. Most people don’t know how to do that kind of stuff. That’s the niche that we filled in real estate. We stopped our wholesaling. We stopped our coaching. We’ve converted our whole office. It’s a 6,000 square foot here in Chattanooga, and we’re about to move to a 14,000 square foot. We run the largest transaction coordination company in the country.

It’s amazing what you wished for and now it may even get a little bit bigger than what you ever wanted.

Once we decided we were going to do this, I was always very intentional about what the end looked like. We own two title companies now. One’s a partnership with Investorlift and one’s our own internal title company. The reason we started a title company is because I was dealing with all these files. In 2023, we did over 2,200 files. In 2024, we’ll do close to 4,000. It’s a lot. We deal with a lot of files. Even though we have 400 title companies who are our partners across the country, it’s like doing a JV deal. Nobody cares as much about your stuff as you do.

We swing a big stick in the title business, but it’s still getting people to work on our speed for our clients is tough. We looked at it and we said, “Why don’t we open our own title company, and then at least we have complete control over the deal? We can run it through as fast as possible.” Now, we’re licensed in Florida, Texas, Arizona, Tennessee, and Kentucky. I think North Carolina is next. We’re rolling out of the biggest states volume-wise that we see that we have a need for. Eventually, we’ll be probably in the top 20 or 30 states.

That’s specific to your title company but what about the easy closing services? Is that nationwide or what does that look like?

Our transactions company is nationwide and that was very intentional too. Being a transaction coordinator, not near the amount of licensing that a title company is, but I knew two things. One is if I’m dealing with you and you’re in West Virginia, you could get a deal in Maryland. You could get a deal in New Jersey. You could get a deal in Ohio. We knew that we couldn’t start and be in some of the states. We knew that we had to be in all the states, which was a challenge. I’ll tell you. There are lots of different states out there like attorney states, escrow states, and abstract states. Every state feels like they do something a little bit different.

Even beyond that, 3,100 counties love to do shit a little bit differently. We knew from day one we were going to do deals in all 50 states and then the other thing was that real investors do different types of deals. We couldn’t be whole wholesale deals. We knew we had to be wholesale, novation, sub-to, notes, wraps, owner finance, lease option, and whatever types of deals because that was what I did.

As an investor, I did real deals so I always approached this business from that point of view. In the beginning, I thought I was starting it for me and some of my friends. We always had those as core values and guidelines of every state, every transaction type, all of our coordinators are going to be certified by me and my team. they have to prove that they understand how to do all these deals before we’ll put them on the phone.

The other thing as I looked at it, I was like, “If I was the client and I want to trust the transactions company with my deal because these are big deals. This is life-changing money, $30,000, $40,000, $50,000, and $100,000. We’ve got one that’s about to close. It’ll be our biggest of the year. It’s $240,000. I wanted to make sure that our coordinators cared as much as our clients did. What we did is we put them on a blended pay system where they get a salary plus a little commission every time a deal closes.

What that does is incentivize all of our coordinators to push and make sure that these deals are getting over the line. I always tell people, “One, you’ll have better control with us. We’re going to get more of your deals closed.” Can we get them all closed? Absolutely not. There are some that are such a rat’s nest that it’s going to be three years in probate and it’s a $2,000 assignment fee. I’d be like, “I don’t know that the juice is worth the squeeze here, but if you want it, we’ll keep working on it.” Sometimes you can’t get them closed. You get a seller that decides I’m not going to sign anything and nobody can force them to do that. It’s been wildly successful.

From my own experience, I don’t keep track anymore. I’ve closed thousands of deals in 21 years. It’s interesting now trying to remember some of the addresses from even a few years ago but the thing that I’ve experienced is I’ve dealt with a lot of title companies. I have relationships with a couple that are good. They’ll bend over backward. They’ll solve all those problems but when I’m forced to deal, especially when I was in the lending business.

Simplifying Transactions

We had a hard money lending company that my former business partner still runs but deals with all of these different counties and title companies. We were lending statewide in the state of Wisconsin. What does that look like? How does a new client come in and work with you with their transactions?

We do something unique. We’ve looked at what other people have charged. There’s nobody that had ever done it and still hasn’t done it scaled out like we do, but there are small regional people. Some realtor offices have one coordinator that might handle 3 or 4 agents. We looked at what other people were charging and the lowest person out there charges $849 but if you go into some of the Facebook groups, like the sub-to group, some of those coordinators will be $1,500, $1,600, or $1,800 for a deal.

I looked at that and I’m like, “That’s crazy,” because a deal’s a deal. I get it. Some are going to be more complicated than others, but we’re going to treat them all like one deal. I said, “We’ll charge less and we’ll do this at scale,” but the problem is that most people don’t realize is almost 40%, and sometimes 50% of deals never close. What happens for us is you send us a contract, I’m like, “We have to go to work immediately.”

It’s going to come to us. We’re going to assign it to one coordinator. That coordinator’s going to be assigned to that deal until the end. We’re going to get it to the right title company in West Virginia that does novations that we know we’ll close this deal but then we’re going to jump on the phone and we’re going to call your seller. “Mrs. Smith, this is Claudia. I’m working with Derek on your deal over here at 123 Main Street. I’m going to be your point of contact from here to closing.”

That’s because I want you out. I want you to go do your thing. Go get your next deal or go sell your deal. Get out of the weeds and go do the stuff that makes money in your business. We’ve also got this five-page intake document. “Mrs. Smith, I need to ask you some questions for the title company so I can get you paid as quickly as possible.” That list tells us where the problems are and what we need to start to fix. Who else is on the deed? Is there bankruptcy, foreclosure, or liens? Is it a mobile home? All those types of things.

However, the reason I have to go do that so quickly is because I have to assume you’re going to assign this deal tomorrow but we know up to 50% of deals may die. Fifty percent of the time, we’re working for free and that sucks. It’s hard to get a coordinator to work for you. As fun of an office as we have, nobody wants to work for free, and they’re also not going to want to do your deals if you keep sending those types over. We looked at that and I’m like, “The only option is one, I can send you a cancellation fee,” and that sucks because you had your $40,000 deal not closed, and I’m going to send you a cancellation fee of $300, which is what everybody else does.

I talked to a mentor and I’m like, “What can we do?” He is like, “Why don’t you make it like a magazine subscription where you could do so many deals per month? Do it for them even a little bit cheaper that way you don’t have to charge them a cancellation fee because you have recurring revenue and you know that they’re going to stay a client. That worked out amazingly. People love that. Our base level right now for 1 to 5 contracts is $1,997 a month, which is less than $2,000. If you were to do five deals, it’s $400 a deal, which is half the price, of anybody else. Also, you’re not going to have any cancellation fees. There is none of that stuff.

That’s the model that we went to. It works well. Our clients love it. The other thing that we do that I’ve been talking about for a few years, and a lot of people have started to adopt it is we’ll teach all of our clients how to put a transaction fee into their selling contract. What they’ll do is they’ll pass that charge on to their end buyer. I got this out of a mastermind too years ago. It was a little different usage but basically where the basic idea came from.

Most of our clients will do a $750 transaction fee. Some do $999, which is crazy but if you did five deals and let’s say you did a $999 transaction fee, you’re going to make an additional $5,000 but you’re only paying me too. What happened? You’ve taken the worst part of your business that you hate and you’ve turned it into a profit center, which is great. I’ve got some people that charge the seller and the buyer and are making $8,000. It can be an incredible profit center and you don’t have to interview, hire, run ads, train, manage, and do all that stuff and you can have the best team in the country closing your deals for you. It’s an absolute no-brainer.

The Challenge of In-House Operations

I love that and I will tell you that we do all of ours in-house and it’s a pain in the ass. I have staff and employees so I’m not necessarily the one that has to, but I still have to be the point man. I still have to worry about, “Did this get done or not get done?”

Somebody goes out. They’re sick, they quit, or they have a baby. Now, you’ve got to replace them. Whereas with us, I’ve got eighteen of them here. I’ll switch one in for one in for another one and it’s seamless to our clients.

Are they all in-house in your building? Don’t you have virtual?

I don’t allow virtual. Everybody is in the office, which is hard because finding good quality people that have real estate experience in a town of 300,000 people, we’ve got them all. That’s me. I’m an old guy. I like people being in the office, but even our people appreciate it because if somebody’s got a problem, we’re set up into teams. Someone’s like, “I’ve never done a foreclosure in Indianapolis. Suzy has done it. Here’s exactly how you do it.” You don’t get that kind of teamwork in Slack and Zoom. It’s not going to happen. We like everybody being in the office.

I’m that way too. Most of my staff is virtual, but I require them, even when we have a meeting, I want everybody’s cameras on because it drives me crazy when it’s not personal enough or you know somebody is not paying attention.

That’s the worst thing. I try to tell that to people when I’m doing Zoom. I’ll go into a big coaching group and we’ll come in and talk about whatever. I’m like, “Guys, turn your cameras on. The speaker gets energy from seeing that you’re paying attention.” It’s so hard to look at a camera and talk into that camera and see names on a screen. It’s terrible.

I can talk to you for hours and hours. I want to be respectful of your time as well. What’s one question that I should have asked you that I didn’t?

I think why those 40% to 50% of the deals don’t close. What I think it comes down to is a lot of people’s acquisition process is a little bit loosey-goosey where people aren’t asking the right questions like, “Who is on the title?” I’m not saying you have to do a deep background check, but I see a lot of these deals where they don’t realize that it’s one of the nine heirs who are trying to sell this house. They are looking it up on PropStream and they’re like, “John and Susie Smith,” but they’re talking to Bob. “Who is John and Susie?” “They’re my parents. They passed away.” “Are you the authorized person to sell the house?”

On the title side, I see a lot of lack of questions that are answered there or asked there. Also on the acquisition side, I think 50% of those deals don’t close. They don’t close because they’re at the wrong price because some acquisitions guy or gal is so interested in getting that contract signed that they’re not paying attention to something like, “How’s the kitchen?” “The kitchen’s great,” and they move right on. “Tell me about it.”

Had they told them about it and learned that it was stained plywood cabinets with a laminate top with the middle band around it that had been like, “We’re probably going to have to budget $30,000 or $20,000 here to replace this kitchen and they wouldn’t have offered as much. Those are probably the two places that I see and unfortunately, a lot of it is on the acquisition side and putting bad deals under contract.

That’s what I was going to mention. It’s uneducated or inexperienced people that you don’t know what you don’t know. We’re not sitting here judging anybody, but it’s a fact. When you go through enough of those issues and challenges as you and I have over the last twenty-plus years, it does become second nature. We’ve seen the end of the movie so many times that the cliffhanger is not a cliffhanger for us but for many people, they don’t know that they should have asked more questions.

It’s not like you and I came out of the womb knowing that we needed to ask these questions. No. We screwed up enough.

We got our asses kicked.

“I couldn’t sell this house because the repairs were worse than I thought. I didn’t ask good questions. Let me start asking better questions.” You can go do 100 deals and lose 50 of them or you can hire a coach and somebody that can shortcut that process for you. You’re going to learn one way or the other and you’re going to pay one way or the other. It’s going to either be tens of thousands of dollars in lost deals or you can hire a coach for a fraction of the price that has done these things that can give you that kind of shortcut to the second floor.

Education is never free. I don’t care what anybody does. I know how many millions I’ve lost when the markets crash and everything else. My education, I’m sure I could have paid for Harvard many times over if I was smart enough to go to Harvard, but it’s led us to where we are now. You’ve got easy REI closings because of what you went through. I’m leading Generations of Wealth because of what I went through and if we hadn’t, nobody would even know who we are. If we would’ve quit or if you wouldn’t have spent that agonizing night on a mattress in the heat of June in Chattanooga. That’s what I think is a blessing now.

I don’t ever regret any of the decisions that we made or any of the things that we went through. It’s part of your story. It’s a thing that makes you who you are. I don’t think that’s a good idea. I think it’s great to learn from it like, “I’m not going to do that again. That was dumb.” It’s all part of the journey.

If anybody wants to work with Dave and his team, go to TheGenerationsOfWealth.com/transactions. I know from our previous episode that we recorded and the time we spend now, I look forward to getting to know you more. Honestly, I think I’m going to end up being a client because I don’t like the transaction bit.

I tell people I run the biggest company in the country, and I wouldn’t want to do it every day. I love helping our team solve problems, but it’s a grind to do it every single day. If you’re going to do one deal a month, it’s not a big deal. You can certainly do that. You don’t need us but if you’re going to get to 2 or 3 deals and you want to scale, that’s who our ideal client is. We’ve seen it over and over again.

They come in doing 1, 2, 3 deals, and six months later, they are doing 5, 6, 7. We had one client. This is far to the extreme, but he came in doing $97,000 a month, which is an incredible number. Three months later, he was up to $750,000 because he had his whole team instead of his dispo and acquisitions people trying to do transactions. Now, they were focused on getting deals and the growth was amazing.

David, I can’t tell you how much I appreciate your time. We’ve been going for quite a while now. As I said, we could keep going. I have no doubt about that but any last comments or words as we wrap?

I appreciate you having me on. I’d love to come back again and talk about some more stuff whether it be marketing, wholesaling, or whatever you want to chop it up about. I don’t have time to do a lot of mentoring and coaching anymore so I do love to try to get back on podcasts and events and speak where I can. I am always happy to do it.

We appreciate you coming. For everyone, thanks for tuning in. This is an honor for me to get to spend time with people like David and bring his knowledge and his experience to you. Come back next week for another great episode. Please go out anywhere you’re tuning in to this, share it, and like it. Give us all the five-star reviews you can. Help us grow our network and go live with your vision. Love your life. See you on the next one.

Important Links

• Reicot.com
• Gowvoyage.com
• TheGenerationsOfWealth.com/fbgroups
• TheGenerationsOfWealth.com/transactions
• TheGenerationsOfWealth.com/YTChannel
• TheGenerationsOfWealth.com/Instagram

About David Olds

David Olds is a seasoned and successful real estate investor based in Chattanooga, Tennessee.

With a passion for real estate that began in 2002, David and his wife unknowingly purchased their first home, which turned out to be a foreclosure. Little did they know that this fortuitous event would be the catalyst for their journey into the world of real estate investing.

Building on his expertise and success in real estate investing, David founded ezREIclosings, a nationwide virtual Transaction Coordination Company that serves investors and wholesalers. At ezREIclosings, the team specializes in handling complex title problems, streamlining the closing process, and taking the burden of tedious administrative tasks and paperwork off the shoulders of investors.

This allows investors to focus on their core business activities.By providing top-notch transaction coordination services, ezREIclosings not only facilitates more deals but also empowers real estate professionals to generate more revenue and attain greater freedom in their businesses. ezREIclosings also helps investors offset their transaction coordination expenses and turn them into a profit center.

With a focus on excellence, a wealth of experience, and a genuine desire to help others succeed, David Olds continues to be a driving force in the real estate investing community.

His contributions to the industry and commitment to his clients have solidified his reputation as a leader and innovator in the field of real estate investment and transaction coordination.