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In this conversation, Dawn Fleming shares her remarkable journey from a career in law to becoming a successful real estate investor, particularly in foreign markets. She discusses her experiences during the 2008 financial crisis, her decision to sail away from her troubles, and her eventual investment in Isla Mujeres, Mexico. Dawn emphasizes the importance of seizing opportunities and adapting to changing circumstances in both life and business.

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Investor Fuel Show Transcript:

John Harcar (00:01.76)
All right. Hey, guys. Welcome back to our show. I’m your host, John Harcar, and I’m here today with Dawn Fleming. And what we’re going to talk with Dawn today about is besides journey and business in the real estate, we’re going to talk about foreign markets and why she made a switch. Remember, guys, at Investor Fuel, we help real estate investors, service providers, I mean, all real estate entrepreneurs, 2 to 5X their business. We help provide the tools, the resources in the community to scale and grow.

Dawn Fleming (00:13.71)
Thank

Dawn Fleming (00:25.998)
Yeah.

John Harcar (00:30.26)
your business, which in turn helps live the life that you want to live. So Don, welcome to our show.

Dawn Fleming (00:36.268)
Thanks for having me, John. Pleasure to be here.

John Harcar (00:38.496)
Yeah, and I’m excited to talk about foreign markets. I got some friends that do some investing down in Mexico. But before we talk about that, tell us a little bit about you, your background in business and real estate and what brought you to today.

Dawn Fleming (00:52.846)
Sure, well, I’m actually coming to you from my hometown of Minneapolis, Minnesota. The last three summers we’ve been snowbirds, but been living full time in Mexico for the last eight years. I left the snowy country in my late 20s and moved to Orange County. And my husband was a physician, ended up doing medical school there. I was in real estate.

John Harcar (01:00.416)
Awesome.

Dawn Fleming (01:17.528)
Here in Minneapolis, I continued that career in Orange County. I was a mortgage broker there. I had done property management, loan servicing, even listed and sold a few houses on a part-time basis just to get them through medical school. And then in a moment of insanity, I decided to go to law school. And the reason for the insanity was my husband, who was a psychiatrist.

John Harcar (01:36.01)
We a freeze up.

Dawn Fleming (01:46.69)
said he didn’t want to be married anymore. So it was basically high school, college, medical school, residency, see ya. You heard that story before. So I’m like, okay, don’t want to do girls’ day because I was tired of the roller coaster, right? I mean, just I’m like, when you got a six figure income earner spouse, it’s one thing, but when you’re single on straight commission, I was like, I got to find a better gig. So I went to law school, I actually had the

John Harcar (01:52.732)
Wow. Yeah.

Dawn Fleming (02:11.306)
incredible opportunity to do international business transactions. worked on, I like doing deals. I like that part of real estate. And so I got into international trade was blossoming in the mid nineties. So I actually went to work for one of my former professors. did engineering, procurement and construction contracts in the mining industry. So I actually worked on

John Harcar (02:19.786)
Okay.

Dawn Fleming (02:34.702)
20 million to $2 billion mining facilities and traveled around the world making deals. And it was cool till the price of gold went under $300 an ounce. Hard to

John Harcar (02:46.7)
Mmm. Yeah. Gosh, think if you bought it back then and you’re holding onto it.

Dawn Fleming (02:52.14)
I didn’t know what I didn’t know, right? So anyway, I went to the firm, which sucked, and I did securities law long enough to know I never wanted to be a securities lawyer. And then I ended up in sole practice by myself after I got fired, pretty much for not wearing pantyhose, but that’s a whole nother story. won’t. I have nice legs. yeah, that’s a story.

John Harcar (02:54.368)
We all say that.

John Harcar (03:16.192)
Yeah, that seems like a long- that’s a whole nother podcast.

Dawn Fleming (03:21.568)
But anyway, so I really didn’t want to be a sole practitioner just because of the stress, the liability, accounts receivable, all that stuff. And so I ended up hooking up with what was then prepaid legal back in the day, now known as Legal Shield. And I just basically was throwaway clients. People think you’re an attorney, they think you know everything. So they’re calling me about divorces and DUIs and bankruptcies and landlord tenants and all this stuff. Like, can I make a corporation for you or, you know, draft some contracts? So

Anyway, it was a good gig. made, you know, 500,000 bucks part-time, just referring business. I couldn’t help. And then my girlfriend asked me to go to their convention in Las Vegas. Now I’m not a gambler back. I don’t know. I guess they still smoke there, but you know, there’s pornography all over the sidewalk. It’s dirty. It’s nasty. I’m like, I don’t want to go to Vegas. And she’s like, come on. It’ll be fun. That trip changed my life because the keynote speaker that year was a gentleman by the name of Robert Kiyosaki. And.

John Harcar (04:08.192)
No.

Dawn Fleming (04:20.47)
What I heard that day rocked my world. I remember sitting there in this big stadium and thinking to myself, my God, I’m an S. How did I get to be an S? I really never wanted to be an S. Nobody told me. Why didn’t somebody tell me? And I realized I I’d recruited about 80 people, just other attorneys really who, you I said, Hey, if you, know you get business that you can’t help, you know, send them to me. I got a way to help them.

John Harcar (04:36.32)
Mm.

Dawn Fleming (04:49.934)
I said, you know because I told her I said listen, I’m not going to any of those meetings. I’m not shaking the tambourine I’m not shaving my head. I’m not you know drinking the Kool-Aid. So that was in April and I I said, you know, I Know practicing law is never gonna give me the life of my dreams. I’m a business attorney I know there’s other ways to make money. I got to find me a better one and I had this business that I just done on the

John Harcar (04:57.76)
Hahaha

John Harcar (05:14.133)
Mm-hmm.

Dawn Fleming (05:18.112)
you know, basically not really effortlessly. And so I’m like, well, I wonder if I really tried because he talked about a B quadrant business business included network marketing. I was like, you know, I wonder if I could do this. I really didn’t think that that was kind of going to be my gig. But I went for it and ended up closing my practice the end of that year by the end of September, replaced my income my first year. And I did employee benefits. Actually, I was going into companies and sharing the service. And then, of course, we know what happened in 2008. Bottom fell out of the market.

And a lot of my companies were closing their doors, massive layoffs. The way they paid their commission, it was a one-year advance. And they only had to keep it for a month, right? So I ended up in what we affectionately referred to as charge back hell. I worked for free for six months trying to get back to zero. And I said, I can’t do this anymore. Meanwhile, I had taken my cute little house in Orange County and

John Harcar (06:06.847)
Mm.

Dawn Fleming (06:13.016)
tapped the equity, I bought two more rental properties, because that’s what Robert said to do, right? Hey, I get some of this passive cash flow coming in. And then my husband and I had the opportunity to buy a business. So quarter million bucks went to this business was actually another downline, big, big, massive downline I had a chance to buy into. And then we were going to sell our house the following year. So I was in 2006. Then all this other stuff happened. And then

John Harcar (06:17.41)
That’s what Robert said. Yeah, yeah, yeah, exactly.

Dawn Fleming (06:42.67)
we realized like all of sudden the value, right? I tapped the equity, my house was worth $725,000 and the two houses I bought were about two and a quarter each. And so I suddenly found myself with, you know, what used to be $1.1, $1.2 million worth of real estate, worth less than $600,000. Okay.

John Harcar (07:04.906)
yeah, say less than half.

Dawn Fleming (07:07.048)
And I couldn’t sell it. We were gonna sell, go to Florida. We were burned out on the concrete jungle, LA. I had nothing keeping me there. Tom’s kids were grown and gone. Meanwhile, we bought a big sailboat in 2006, because we were living large. We were making good money, know? Life was good. And we said, well, you know, we hung on for two years. I tried making calls. Nobody wanted to talk to me. Bank of America transferred me 10 times, one time.

John Harcar (07:20.478)
Right. Yeah.

Dawn Fleming (07:33.772)
because the $10 an hour employees would find out I’m an attorney and nobody wanted to talk to me. after two years, really painful years, we said, screw it, we’re out of here. Jumped on the sailboat, like three houses in foreclosure, sailed all the way through the Panama Canal, relocated to Panama City, Florida. had sold a lot of stuff, but moved our stuff into storage, a couple of cars. And we checked out for six months, sailed down the coast of Mexico.

John Harcar (07:38.496)
Mm-hmm.

Dawn Fleming (08:02.638)
really just said, I don’t care. I mean, you get to a point in life, John, where things are out of your control. What do you do? I talk about that in Claim Your Dream Life. like, sometimes you just got to leap and hope the net appears. And that’s really what we did. didn’t really. Tom was 60. He did high-end surveillance projects. I mean, we’re talking Port of LA, Long Beach.

John Harcar (08:18.569)
Mm-hmm.

Dawn Fleming (08:29.804)
Dallas Fort Worth Airport, the White House, big, big infrared security. The governments went broke. So all of his projects got, he was a subcontractor to larger firms, but everything kept getting pushed off to the right. He went from go away when you answer the phone to the phone stopped ringing. And so that went away. The Florida houses, the musical chairs stopped, right? And all the flippers flooded the,

John Harcar (08:34.112)
She is, right?

Dawn Fleming (08:58.752)
rental market. So I bought them right, you know, don’t kill the cow, right, get the milk, don’t kill the cow. So I bought them for cash flow, went from $1,200 a month to barely could rent them for nine. You know, couldn’t I mean, it was was really serious. And I had no idea why I had no idea why no no idea. So we cruise around, we stop in Isla Mujeres, which I had been going to little if your listeners don’t know, it’s a lovely little

John Harcar (08:59.902)
Hmm.

Dawn Fleming (09:27.182)
Caribbean Island off the coast of Cancun. I used to say it’s an 18 minute ferry ride and a world away from Cancun, but Cancun has arrived. It now gets 25 to 30,000 visitors a day on an island that’s probably three miles long. So why I don’t live there anymore, one reason. But anyway, we stopped there and I really, it felt like home. I’m like, we got to go to Florida, like all our shits in Panama City. Like we can’t stay here, we got to go.

John Harcar (09:41.224)
Yeah. Wow, that’s incredible.

Hahaha

Dawn Fleming (09:56.878)
So we kept going, we got up there. We’d pull into Panama City Marina, you know, where’s the marching bands, the bloons? Like we just finished this 5,000 mile journey. Well, we didn’t know a soul, know, nobody knew about our trip. So we just got in there on St. Patty’s Day, went and had a green beer and came back and said, wow, that was cool. And then the next day a man came home from work and my husband’s never met a stranger. So he starts chatting with this guy, Donnie.

John Harcar (10:10.154)
Right, right, right.

John Harcar (10:14.464)
Fun.

Dawn Fleming (10:25.646)
And he’s like, Donnie, what are you doing? He goes, well, I’m electrician at the local shipyard. He goes, there’s a shipyard. Because he was like, you know, I love you, dear, but we’ve been spending 24-7 together. I think I might go get a job at Home Depot. Because he’s 60. I’m 50 at this point. And nobody’s hiring in California, 60 years old. Like, you’re done. Nobody wants to talk to you. And he hasn’t had a job in 25 years. He’s been self-employed. So this whole job thing was like, OK, I don’t know how this is going to work.

John Harcar (10:35.782)
Right, right, time for a little break.

John Harcar (10:44.552)
Yeah, right. Right.

Dawn Fleming (10:53.186)
But he says, well, yeah, actually we’re really busy. What do you do? He goes, well, I’m an engineer. He goes, are you an electrical engineer? And he’s like, yeah, actually I am. He’s like, you need to talk to my brother-in-law. He’s my boss. So that week his brother-in-law comes over, interviews Tom over a beer on the dock and says, yeah, we got too many Indians, not enough chiefs. If you had your own company, 25, 30 employees, we need supervisors. So he ends up getting hired.

John Harcar (11:10.368)
So cool.

Dawn Fleming (11:20.194)
He spends about four months in the yard and pretty soon he’s designing 300 foot platform service vessels for the oil industry. so meanwhile, meanwhile back at the ranch, I’m practicing law representing myself, trying to figure out why I still own these three houses in foreclosure because I was certain they would all be taken and gone during our trip. Well, I had a very smart real estate agent, fortunately, and she said, Dawn,

John Harcar (11:29.182)
Wow.

John Harcar (11:43.615)
Right.

Dawn Fleming (11:50.306)
just rent them out, keep the money. Cause you can’t just like start making payments again. You have to do all the arrearages too, right? Just keep the money and they’re not going to foreclose on you. She goes, you have no equity in those houses. They’re occupied. They’re watering the lawns there. You you’re cutting the grass, you’re maintaining the houses. Cause if you remember, like people were stripping houses and you know, they were going after all the people that had a lot of equity. I had no equity. So she’s like, you’re low man.

John Harcar (11:55.712)
Sure, you have to catch it up.

John Harcar (12:12.82)
Yeah, yeah.

Dawn Fleming (12:19.47)
Like they’re not gonna, and sure enough, by God, that’s what happened. And in fact, one of them, I get back, there’s a FedEx envelope waiting for me. It come in like the week before we were down in Fort Myers, comes in from Bank of America, because it’s all countrywide loans, right? And I open it up and it says, sign here, send us $800. We’ll bring your loan current. We’ll give you 5 % fixed rate. We’ll knock $40,000 off the principal. No interest, no payments.

John Harcar (12:19.946)
Yeah, they don’t want you.

John Harcar (12:47.398)
Whoa.

Dawn Fleming (12:49.25)
just pay us when you sell it. go, okay. And so I signed it on 40 grand. Yeah, the other was at 5%. And I had one of those icky, neg-am, know, liar loans kind of thing. And so it was bad. So I go, okay, that’s cool. So I sign it, I send it in. That one’s taken care of. And then the other one, and so I’m looking, I mean, we’re in debt, like, you know, Tom’s, you know,

John Harcar (12:52.274)
No interest, no payments.

Cool. Right.

Dawn Fleming (13:18.254)
We were just, were way below zero. And so I call a bankruptcy attorney and panhandle and I go, hey dude, I go, maybe I can fire. I had never been late on a payment in anything my entire life. I was almost 50 years old and it was killing me that my credit was bad. So I go, can I do a chapter 13? I’ll pay it back. I just need some time, renegotiate, whatever. He’s like, no, if it’s over a million, you can’t do that. I’m like, okay.

John Harcar (13:33.482)
Yeah.

Dawn Fleming (13:47.278)
And he says, by the way, this other house, did you know there’s a hearing coming up? This is in about October, November. I think it was about November. He goes, you know there’s a hearing coming up on your other house? I go, no. He goes, yeah. And I got the notice next day. So the court in Florida will close a case, sua sponte, on its own accord, if there’s no activity after 10 months. So it was a hearing to dismiss the case. And I’m like.

there was a motion for summary judgment in October, was pretty much the day we left almost California, and they dropped it like a hot potato and nobody did anything. I go, that’s weird. Why didn’t they foreclose? Well, if you remember, 60 Minutes came out, RoboSigning, all that stuff, all the fraud in the mortgage industry. Turns out the reason they gave me such a sweet deal was my foreclosure attorney for the bank

John Harcar (14:29.045)
Yeah.

John Harcar (14:35.946)
Mmm.

Dawn Fleming (14:44.086)
was disbarred for running an illegal foreclosure mill. There was a robo-signed assignment. They would have never been able to foreclose on that house. Did they disclose that? no. And then the other one, same thing. Basically, the named partner of the law firm forged an assignment on the courthouse steps, went in and filed the lawsuit. And so they saw what was happening. They’re like, we’re out. And so it was…

John Harcar (14:55.359)
Hmm.

John Harcar (15:08.736)
Jeez. Wow.

Dawn Fleming (15:11.31)
So every day, Tom’s coming home from the shipyard and I’m going, honey, you’re never gonna believe what I found out today. Like, this is fucking, oh my gosh, it was incredible. So long story short, we did a short sale on the Orange County House. I still have the one with the 5 % interest rate. And then the other one I ended up, I had it for like 10 years.

John Harcar (15:17.28)
A new story every day.

That’s so fun.

Dawn Fleming (15:37.398)
and did a cash for keys eventually. could have taken, my attorney actually was married to a Pell attorney. He would have taken it all the way. And I was like, you know, some, I put 25 grand down on this property. Sometimes you got to know when to fold them. Cause if I had lost that lawsuit, like they could have come after me for all the back payments and everything. So I walked away from that. But at any rate, so we lived in Panama city for two years, kind of rebuild.

John Harcar (15:55.786)
Yeah, yeah.

Dawn Fleming (16:03.572)
had the opportunity to, we lost the other business that I had invested for a quarter, a quarter million dollars into that. That was a long story. Well, the gentleman that I partnered with to buy that book of business ended up leaving the company and they terminated him. And so took his, his down. I said, and I was a silent partner. Nobody knew we, was a corporation. So I contacted him and said, Hey, by the way, if you want to terminate him, that’s fine. But I also own this business. So you should give it to me.

John Harcar (16:09.696)
What happened?

Dawn Fleming (16:33.41)
And they basically said, Pound San, go talk to your partner. And I didn’t have the money to hire an attorney or anything. But the good news is he went to, the reason he left is he went to a new company that was a startup in 2011 that was in the anti-aging space, did $100 million its first full year in business. And so Tom and I made over a million bucks in six years on a part-time basis with this other company.

John Harcar (16:39.466)
Sure.

Dawn Fleming (17:01.966)
And part of it was because I was positioned properly on a startup. So we dug out, we moved to Southern California because they use the words wind chill in the winter weather forecast in the panhandle. I don’t know if you’re aware of this. I thought Florida was warm and the first winter wasn’t too bad, but the second winter it was in the thirties. And I said, I am not digging this. So.

John Harcar (17:02.24)
That’s awesome.

Dawn Fleming (17:26.038)
We actually, New Year’s weekend, Tom had some time off. We went down to Fort Myers. It’s like 4th of July weekend. Everybody’s on the beach. I’m like, no, this is more like what I’m talking about. our lease was up in May. We ended up moving to Punta Gorda, which is about a half hour north of Fort Myers. And we lived there for four years, just kind of living.

Living large, we belonged to the yacht club. We got involved with competitive tennis the first time in our lives, played golf. Life was good and rented this beautiful waterfront home with our big sailboat out in front and a little Sea Ray powerboat for cruising around. we were kind of ready. By 2015, we were ready to buy again. And I said, okay, let’s look. So we started looking at property all the way from Sarasota, Bradenton to Naples.

John Harcar (17:59.207)
Wow.

Dawn Fleming (18:21.75)
everything we looked at was a million bucks and the taxes about eight grand a month for waterfront property, hurricane insurance, even back then. All right, so you’re talking a grand a month before you ever even think about a mortgage. And we kind of want to go cruising anyways. So it’s like, okay, we’re going to buy a big waterfront home to only be there half a year. I’m not feeling it. I go, let’s go to Isla because we had been going there. He’d been going with me.

John Harcar (18:37.726)
Hmm.

Dawn Fleming (18:50.414)
The network marketing companies love to go to Cancun for incentive trips. They’re usually about four days. That’s not long enough. You’re coming from California. So I go to Isla. My girlfriend turned me on to Isla Mujeres in 92. It’s changed a lot. It’s still beautiful, but it’s changed a lot. we looked at, we kept an eye on the market. You know, we’re all like always looking at the new condo complexes that were coming in, you know, watched kind of the growth. So I went down there in 2015, met with a friend of mine.

John Harcar (18:56.064)
Hmm?

Dawn Fleming (19:18.638)
who owns the number one restaurant on the island. I met him in 92, he was a bartender on the beach. Kind of fun to see somebody grow into that. But we sat down over beer and I said, Sergio, talk to me about the island. He goes, well, first of all, goes, don’t buy condo. He said, too many rules, people don’t like it, the homeowners fees keep going up. I would stay away from condos. He said, but there’s a shortage of three and four bedroom homes on the island. So if you’re gonna buy something, buy a house.

John Harcar (19:25.088)
Mmm, yeah, that’s cool.

Dawn Fleming (19:48.162)
I go, okay, so we go meet with the realtor. We found one that we really liked, made an offer, and it was contingent to financing. Because we had about, how about 150,000 in a, like a tax favorable, not pre-tax, was after-tax dollars, retirement account.

But it wasn’t doing much, you know, it was like kind of this sad, slow growing nest egg. I’m like, you know, and the company had changed hands. It was kind of some shady stuff going on. I was like, I think we should get it out of there. So we needed seller financing, which is a good way to buy foreign real estate. So we made an offer. Turns out the only thing I can find is 16%.

John Harcar (20:35.424)
Mm.

Dawn Fleming (20:36.758)
Now, my husband liked the house. said, honey, the numbers don’t work. I’m sorry, because this is an income property. This is not a house for us. not talking, we have no idea, no plans to move down there. think it’s strictly a way to diversify our income, because I didn’t like having all my eggs in one basket. I saw that movie before and I didn’t, we lost that business overnight. So I said, we got to diversify. So we backed out.

John Harcar (20:46.226)
Right.

Dawn Fleming (21:04.224)
And I said, no, we can’t do this. And then that was about Thanksgiving. I get a call in February from the real estate agent. She says, hey, there’s another house been on the market for a year. It is in a much better location, closer to the beach, which has now become the number one beach in all of Mexico in some circles or some news articles. And the seller has agreed to financing at 6%. I go, okay.

She said, come on down. You can stay there for free if you end up buying it otherwise, you know, so we go down there. We look at it. Now, first of all, I take one look at it. It’s Kelly green and yellow. I’m a Minnesota Vikings fan. It’s painted green babe hackers cover. This is not a good start. I’m like, this is ugly. So I go in and it has some design flaws, which is why one of the reasons it was, but it was only four years old and

John Harcar (21:46.368)
Mmm.

John Harcar (21:50.248)
It’s been a Green Bay Packers fan. How funny.

Dawn Fleming (22:01.922)
It was on a double Caribbean oceanfront lot.

John Harcar (22:05.748)
Wow, awesome.

Dawn Fleming (22:07.52)
And so I said, got some questions and it was the number one builder on the island was what guy who built it. said, it didn’t have a proper pool. had a little puddle for a pool. One of the reasons the rents weren’t higher. So I met with the builder and I said, can we put in a pool? I said, can it, it was, was, it was two level, two bedroom, two bath, first level, zero lot line. So, you know, no, no yard or anything like that.

just the two houses next door. But it had a second floor that was, it had a studio unit that was set way back on the lot. And then it had this huge wasted space patio. And it was like, what are you gonna have a disco party here? Why are we so far back on the lot? I said, can you, is it strong enough as a foundation sound to be able to go up, to expand the second level? Yes. I go, okay, what about,

the third level, because from the rooftop you could actually see the Bay of Cancun.

John Harcar (23:10.08)
Right. Hey, Don, Don, I had to cut it a little bit short, we’re a little past the time. Time flies when you having fun, right? If there’s folks out there that maybe want to talk to you about your experience and some of the stuff you shared, mean, how, is the best way that they’ll be able to get back in touch with you?

Dawn Fleming (23:15.594)
okay.

Dawn Fleming (23:27.182)
Sure, best way would probably be to check out my YouTube channel, which is Midlife in Paradise. And specifically, I have a video that I created that is called How I Found a Dream Home that Funded My Retirement. Because we basically tripled the value of this property and created a multiple six-figure income stream, turned it into a boutique hotel.

John Harcar (23:53.076)
That would be a great thing that we should have talked about before. But hey.

Dawn Fleming (23:56.782)
I’m sorry, I thought you guys said an hour. This was gonna be an hour.

John Harcar (24:00.882)
No, these are no 15, 20 minutes is usually are the time where we where we do these podcasts. But that’s OK. I mean, you shared a lot of good stuff and I appreciate you coming on here, guys. Hope you enjoyed this and you know, we’ll see you guys on the next one. Cheers.

Dawn Fleming (24:07.405)
Okay.

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