How to Start Real Estate Investing With the End in Mind | Cheryl LaTray’s Wealth Strategy

Cheryl LaTray (00:00)
If you’ve got a realtor that you’re loyal to that you will work exclusively with, they will go to bat so hard

for

you that you’ll get some of the best deals. So I have a couple of clients that have made hundreds and hundreds of thousands of dollars because I know that they’re loyal and I’m loyal to them and I go find the best deals and try and create that wealth for them.

Michelle Kesil (01:52)
Hey everybody, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil and today I’m joined by someone I’m looking forward to chatting with, Cheryl LaTray who is a real estate investor, broker, as well as a investor herself, working primarily with flips and Airbnb. So excited to have you here today, Cheryl.

Cheryl LaTray (02:15)
I appreciate that. Thank you so much.

Michelle Kesil (02:18)
Awesome, let’s dive in. First off, for those who are not yet familiar with you and your work, can you share what your main focus is?

Cheryl LaTray (02:26)
I that. I do joke around that I actually play real life monopoly, right? I love the idea of creating wealth in real estate. And so my focus is doing that in a handful of ways. It is both flipping that’s not as robust right now. ⁓ I also do Airbnb’s ⁓ as you mentioned, and I work as a regular real estate agent as well, helping investors create real estate and wealth.

Michelle Kesil (02:56)
Awesome. And so how did you get started in the specific niche of working with investors? Like what made you want to go in that direction?

Cheryl LaTray (03:05)
I was actually a stay-home mom and I was buying and selling houses and I was young, was in my early 20s doing that and was very excited with you could create residual income with rental properties and began to grow that, began to acquire some houses and

years into that, probably four years into that, I did get divorced and I decided to use real estate as a way to have a full-time career and completely replace my husband’s income with Residual Income.

Michelle Kesil (03:44)
And which markets do you operate in?

Cheryl LaTray (03:48)
So in the Greater Rochester area, there’s about eight counties that I serve as an agent, an Airbnb host. ⁓ I also have Sarasota, Florida, and I have North Augusta in South Carolina.

Michelle Kesil (04:06)
Awesome. And what do you feel have been some of the main keys that have made the biggest difference in allowing your business to grow and run successfully?

Cheryl LaTray (04:16)
So one of the reasons that I have houses in those other areas is I’m a mom of seven.

And the kids are now in their 30s and adults. And I had said to them when they were young, if you go somewhere, I’m actually going to follow you and get a house. I have a son in Sarasota, so I house in Sarasota, again, one for my daughter in South Carolina. And then six of the seven kids, I have a house very, very close to them. And I would think, and so one of the driving forces was family. ⁓ Children have all participated in flips. They all know how to flip houses.

well. They’re all doing the same thing that I’m doing where they’re creating wealth in real estate as well. So part of the success was more trying to bring the family into what I was doing and growing it from there.

Michelle Kesil (05:12)
Awesome. And so how did you learn how like the ins and outs of investing and flipping and rentals?

Cheryl LaTray (06:09)
⁓ I literally do blame playing Monopoly as a kid on the idea that wait a minute, can buy, four houses, get a hotel and the rents just keep going up. Wait a minute. It was just pretty exciting. I literally ⁓ really appreciate that game. So.

That’s kind how it started. Bought the first few houses, again, early 20s. And some things I learned the hard way. I didn’t have somebody ahead of me, kind of showing me it wasn’t something my family was doing. ⁓ Very much would read as much as I could. And I’ve definitely read four.

almost 400 books on it ⁓ and I now have probably spent a few hundred thousand dollars on mentors as well. But the biggest teacher is trying. I would absolutely ⁓ hop in, try and then if it didn’t work, adjust. One of the things that I often say is some of the biggest opportunities and successes come out of some of biggest goofs. An example would be we had a house that had a problem with an Airbnb and I was

crushed I was like oh no what’s going to happen here and instead what we did was went in the direction a brand new concept we did minimum of 30 days and as a result it just went incredibly well so where I spent about a week and a half like oh my world’s crashing it ended up becoming an amazing direction and I’ve actually taken most of my houses in the direction of what we call midterm rentals.

Michelle Kesil (07:46)
Yeah, amazing. And why do you feel that that specific like asset class of midterm rentals is more suited for like the way things are working for you?

Cheryl LaTray (07:59)
So I’ll use an example. I had a house for about three years. It was a very well done Airbnb. We had an 86 % occupancy, ⁓ 15 turns within a month. so at first blush, it had all the success, right? Great numbers, ⁓ great turns, all that kind of stuff.

took a minute and did a really hard deep dive. So what is the management platform? What are the cleaners? What are all the supplies? Like a really hard deep dive and found that I was really only making a couple of hundred dollars a month on this property. And it was a huge amount of work. we’re cleaning it 15 times and know, restyling, all of it, all that goes into all of that. And I decided to honor reservations, but I wanted this to, I wanted to try this as this midterm 30 day and did that. and right now we have somebody who’s staying in it for six months.

It’s an insured loss and where I was making $150 to $200 a month on it, I now make a couple thousand dollars a month and I don’t have to turn it so many times. I don’t have to do as many repairs. I don’t have to restock it. And so it was just such a breath of fresh air that I went, I decided to go in that direction on a much larger scale.

Michelle Kesil (09:13)
Awesome. And so what are you most focused on solving or scaling to next for your business?

Cheryl LaTray (09:21)
I totally want to do more of this midterm. This is, like I said, it’s working with a part of it, and I’m going to say maybe 40 % of it, is working with the insured losses when people need a house because something has happened. That is very much something we’re focusing on. ⁓ But people coming into the area needing to explore, needing something for a few months, or where you’ve got grandma and grandpa coming and staying for a couple of months. doing this midterm really has been, that’s what I’m focused on, really trying to grow that.

you

Michelle Kesil (09:53)
awesome. And so you’ve also done a lot of fix and flips. Can you share what that’s journey been like as an investor doing them?

Cheryl LaTray (10:36)
⁓ So I joke around I can tell you all what not to do because I didn’t hit it on 160 flips. Yeah one of the biggest things to realize with that is that time is your enemy and you have to

Michelle Kesil (10:40)
tour.

Cheryl LaTray (10:52)
you have to move really quickly with them. ⁓ I had a situation where I had too many flips going at one time. I actually had a boating accident and then I came off of focus for a little bit and everything snowballed. This is where time was just absolutely running against me. And time eats up the profits faster than almost any of the other different expenses. So one of the biggest things to do is to accurately pace your time to be successful.

with flipping and not to do too many and get spread too thin and then that becomes a really difficult cash flow management issue as well.

Michelle Kesil (11:32)
Yeah, absolutely. What advice would you give to investors that are maybe just getting started or early in their career?

Cheryl LaTray (11:41)
I’ll start with the end in mind. know, because I do a mentorship and I show people how to create, no two designs are the same. Everybody has a different set of skills. Everybody has different circumstances around them and most have different goals. So ⁓ what I have…

said to people doing that or what advice I would give is start with the end of mind. What do want things to look like five, 10 years from now and go backwards and re-engineer it? What I have found, you’re to have the same foreclosure, you’re to have the same rental property, you’re the same Airbnb, but if your end goal is different, it’s going to look different to all three people. So very much having a very articulated, here’s what my goal is planned, going backwards, creating a decision model, and now you’re looking at properties and you

and say yes, no, yes, no, much easier because you know where you’re going.

Michelle Kesil (12:38)
Yeah, absolutely. And what has been like your process for finding the best suited properties?

Cheryl LaTray (12:47)
⁓ So.

One of the I say to investors is when they’re getting started is find a small area first and know it really, really well. Right? And the same applies when you’re an agent trying to learn an area. You go into an area and you dig in. You watch those sales. You go and look at the houses. You really dig in, become familiar with, if this flipper did that, they started at, what they do to, where did it end at, and become very, very familiar with a very small area. From there, what happens is the little odd opportunity

shows up. And I find some of the best deals are not the ones with the big red flag. I am a foreclosure, hey, you know. And when it gets to a foreclosure, it’s gone through, here in New York, years of situations. So it’s gone through quite a bit in order to get to the place where it’s a foreclosure. So people are like, oh, I’m just going go buy some foreclosures. If you take and know a market really, really well and own that you are an investor in that market and you make it known that you’re looking for properties in that market, you will find

find those best deals. If you learn the different techniques and tools of either renting or flipping or any of them in that small area and you become then good with that tool, then you can go to the bigger areas. Now you can do that same thing in a broader area. You’ve learned what to look for. You’ve learned how to find a deal as well. really digging in and then watching this odd listing that came up that, it shouldn’t be listed at that price because you’re so familiar with it.

⁓ is one of the secret things I think about finding properties because it isn’t just get on an MLS listing. And something else that I find as a real estate agent that helps investors, can’t tell you how many times an investor will come over and say, I’ve given, you know, I’ve talked to five, 10 different realtors. I’ve told them what I’m looking for and the person that bring me the deal, I’ll work with them. Little do they know that’s not how they get the best deals.

If you’ve got a realtor that you’re loyal to that you will work exclusively with, they will go to bat so hard

for

you that you’ll get some of the best deals. So I have a couple of clients that have made hundreds and hundreds of thousands of dollars because I know that they’re loyal and I’m loyal to them and I go find the best deals and try and create that wealth for them.

And I know that they’re not going and saying that to five, ten other people, hey just bring me a if you’ve got one. I’ve seen that now for the foreclosure agent I started in 2012 so you know 14 years of watching investors still think that’s the best way to get

the best deals. Agents aren’t motivated, they’ll get you a good deal when you’re loyal to them.

Michelle Kesil (15:23)
Yeah, absolutely. That’s good advice. Do you have any other advice from investors? Yeah, from like the agent side.

Cheryl LaTray (16:11)
So buy from an investor. I’m watching agents that don’t understand, they don’t know, they don’t know how to do a review on a property.

If you’re an investor, work with an agent who specializes or who does investments. So when I had gotten started, again, for four years, I was just buying and selling my own. I wasn’t trying to be an agent. And I had people coming and saying, whatever you’re doing, go do that for me, because this is great. This is pretty cool. And so by practicing what I preach, doing it, that skill set is a big asset to the agents, to the investors that I work with. So I would say to an investor, work with an agent who practices

is what they preach and you’re going to think you’re competing. It’s not the same. It’s really not. create an alliance, work with a skilled agent, you can make magic happen. It’s pretty fun.

Michelle Kesil (17:08)
Yeah, amazing. And so what are you most excited about as far as any opportunities that you see in the real estate industry right now?

Cheryl LaTray (17:21)
Technically what I’m most excited about is, as I mentioned, my family, right? So I want my family to be able to go create that next generation of wealth and…

them to learn from my mistakes. I want them to grow with the resources I have. And so I’m still wanting to be family focused and making that happen for family. That’s what gets me excited. It’ll be navigating trends for the rest of our life, if I can, I guess they say teach them how to fish.

that would be what I’m excited about.

Michelle Kesil (18:06)
Awesome. And so when investors work with you, are you typically like helping them find properties in the New York area?

Cheryl LaTray (18:16)
So yes, currently I’m in the Greater Rochester area. Like I said, I started to buy a little bit in North Augusta, down in South Carolina, playing with that a little bit. yes, mostly I’m in the Greater Rochester, but I do Syracuse and Buffalo as well.

Michelle Kesil (18:34)
Awesome. And so how do your clients find you? it through like referrals or networking? Like what’s your strategy there?

Cheryl LaTray (18:41)
So I did have my first big listing. It was a beautiful historic home. when the person spoke, were, they came as a, how do I say this one? It was a referral from 30 years ago. They were my first listing many years ago, and now they’re parents.

house was available, but there was multiple siblings. each sibling kind of had a realtor. And the one making the decision put us all through ChatGPT and said, okay, who’s the best realtor? And he said, I got to tell you what ChatGPT said about you. It was mind blowing. was pretty exciting. I did just sell that property for 40,000 over list price. was a gorgeous, historic, very unique property. ⁓

So I got my first ChatGPT referral there, which is pretty cool. Cheryl.Latrey at huntrealestate.com is one of the easiest ways you can find me as well. But I started to put together a mentorship. So 2006, I started teaching classes on how to mostly then it was specifically flipping. And we’ve kind of progressed from that to just all the modalities that are available. So I now do mentorships. It’s called Freedom by Design.

Michelle Kesil (19:59)
Amazing, and what does that look like?

Cheryl LaTray (20:02)
That is a one year mentorship. I get my hands dirty. We go hard into all of it. It is.

all the details. is what is your best entity right down to what you’re financing, what is your income tax strategy, know 30-year wealth is created by the money you don’t pay in taxes, right? You’re paying 28 % and you can save some of that. So we go into tax strategy, we go into finding the houses and really digging in. So it’s for one year being fully invested helping them.

and all the resources that I have open up as well. That’s a limited pool because it is pretty hands-on.

Michelle Kesil (20:47)
Yeah, amazing. And that’s helping people like with like newer investors that are just getting started.

Cheryl LaTray (20:55)
Yeah.

Yep. There’s a little bit of a range. So some that have zero experience like, I really want to get into this. I read and hear about it and, know, help me avoid doing some things wrong. So we start there, but then we’ve got, or I have some that are experienced. one of my favorite to work with a whole collection of properties and what he is finding is, getting a little bit older, doesn’t really want to have to do all the repairs anymore and is found he’s making now a lot more money.

⁓ migrating over into being the hard money lender. And so it’s been a five, six year transition out of owning, still own some, but out of that into, hey, my wealth is not created by carrying mortgages for people that are gonna be flipping. So it’s a full range.

Michelle Kesil (21:45)
Yeah.

Yeah, amazing. That makes sense. Thanks for sharing all of that. And before we begin to wrap up here, if someone wants to reach out, connect and learn more about what you’re up to, where can people find you and connect with you?

Cheryl LaTray (22:00)
As I mentioned, Cheryl.LaTray @ HuntRealEstate.com is one of the best and easiest ways to do that. ⁓ that would be FreedomByDesign.com.

Michelle Kesil (22:15)
We’ll appreciate your time and your story. Thank you for being here.

Cheryl LaTray (22:18)
Thank you. Have fun. Thank you so much.

Michelle Kesil (22:21)
Of course. And for the listeners tuning in, if you got value, make sure you have subscribed. We’ve got more conversations with operators like Cheryl who are building real businesses and we will see you all on our next episode.