From Big Rigs to Big Deals Creating an Unstoppable Rise in Real Estate with Gabrielle Simmons

Transcript

[Jeune Ortiz]
Hello and welcome to the United Women in Real Estate Testing Podcast. My name is Jeune Ortiz, founder of REI Social and host of this wonderful podcast where I get to interview great women who are doing fantastic things in real estate. My next guest is Gabrielle Simmons.

[Gabrielle Simmons]
Hi Gabrielle, thanks for joining us. Hi, thank you so much for having me. I’m excited to be here.

[Jeune Ortiz]
Absolutely. Happy to have you here. So when we were just getting to know each other a little bit, you let me know that you were actually going to be traveling in a unique kind of way from where you are to your next destination.

Tell us a little bit more about this trucking company that you have and how you got started there.

[Gabrielle Simmons]
Yeah, actually that is what began my journey into real estate too. So I am in the process currently of buying a couple semi-trucks with some business partners of mine as well. And so I’m leaving my home here in Colorado, Colorado Springs, to go on the road and drive.

I do have a CDL and enjoy driving. I did that for a couple years. Let’s see, I got my CDL when I was 23 in 2017 and loved driving.

So I’m actually excited to get back out there now and do a little bit more driving. I’ll still be doing real estate, of course. That’s always going to be a thing, but I like getting out there to drive too and just see the country in a way that a lot of people never get to experience it.

[Jeune Ortiz]
Yeah, that’s really good.

[Gabrielle Simmons]
So from Colorado Springs, where are you headed? We’ll probably be picking up our trucks in Texas. And then it’s just a matter of getting loads.

So I have contacts with some brokers that I can contact directly and say, hey, find me a load out of Texas going to Pennsylvania, let’s say. And they’ll find me that. Or there’s also like a public board that I can look at and just book the loads on there based on what’s available.

So really just anywhere and everywhere is the answer to that. Where I’m going, anywhere and everywhere. How interesting.

How long are you on the road for this particular trip? It’s hard to say. So we’re in the process of building a large fleet so that we can get government contracts.

My business partners are disabled veterans. And because we have a disabled veteran owned company, we can go after set aside government contracts. And that’s the objective.

So we need to have like 10 trucks is the goal before we can really start competing for some of those contracts. So I’ll be going in one truck driving until we hire a driver for that truck. Then I’ll go.

We’ll buy another truck. I’ll drive that one until we get a driver and so on and so forth until we have our full fleet ready. So I’m thinking I’ll commit roughly six months to the process of being on the road and kind of back and forth.

[Jeune Ortiz]
OK, wow. So I think truck driving does have a lot of women who are actively participating as truck drivers.

[Gabrielle Simmons]
Right? Absolutely right. Yeah.

I want to say the latest statistic was like less than 20% of all truck drivers are women.

[Jeune Ortiz]
I’m not exactly sure what the statistic is. But I could venture a guess that we’re probably maybe 1% as well. Yeah.

Yeah. It’s great that you do this while you’re on the road. So tell me a little bit about what you invest in.

[Gabrielle Simmons]
Do you invest?

[Jeune Ortiz]
Are you able to do this remotely? I know a lot of people are listening. Probably wish that they could live the dream of doing real estate, but not having to be stuck in one geographic location to do it.

[Gabrielle Simmons]
Yeah. Yeah. That really is the best part about real estate.

I think is once we find our niche and we find what works, we can get to a position where we can have some geographical freedom to go wherever we want to go. So I invest in I do lots of different things. I’ll start with what I started with, which is wholesaling.

I went from being a full time truck driver to being a full time wholesaler and doing both. Initially, once I saw that I could wholesale and earn some decent income with that, I decided to come off of the semi truck and move back to Colorado. And, you know, start wholesaling full time.

That first year was pretty difficult. I when I moved back, I initially went and moved in with my mom and rented a bedroom, you know, and that was I love my mom, but nobody wants to live with their mom. And not that I had to, but it made sense, you know, financially to do that.

And I was able to quickly learn a lot about wholesaling and close several deals. In my first year, I closed over 15 deals. They were all very small deals.

And that was that was kind of a big learning experience for me, too, was realizing that what we might hear sometimes from people in the industry of closing 20,000, 30,000, 50,000 dollar deals isn’t an everyday thing. So I actually partnered up with a buyer, a dedicated buyer. And so I was able to shadow their operation and learn a lot about fix and flips and buying property subject to and rental properties.

So my second year, I got into coaching. I started a team where I would bring people in. They didn’t pay me anything.

They just would come and be with our team three times a week and learn from me in the wholesaling space, learn from the dedicated buyer I was working with their side of the flipping operations. And then I one of my students actually did Airbnb’s Airbnb arbitrage. And so we kind of did a trade where I would give him more coaching time and he would coach me on how to do the Airbnb arbitrage.

So I started doing that. And within a few months, I had several properties here around Colorado Springs doing Airbnb and midterm rentals. I quickly kind of pivoted one of my properties that wasn’t performing well as a short term rental into midterm rental.

[Jeune Ortiz]
OK, tell us more about what I’m sure there’s.

[Gabrielle Simmons]
I’m glad you said that because I was going to ask if I should get into that more. Midterm rental typically just means a property that’s rented on a month to month basis instead of a short term. Short term being 28 days or less.

Midterm is going to be more than that. It might be a three month or a six month agreement, but it’s typically a month to month agreement and oftentimes a furnished, fully furnished property, just like in the short term rental arena. So, yeah, actually, that I found to be the best investment strategy in my area.

Of the others.

[Jeune Ortiz]
And where is your way? I know, you know, you travel all over. So where do you invest?

[Gabrielle Simmons]
My backyard, Colorado Springs, Colorado. I have done some deals in other states as well. Just wholesale deals so far, although I do.

Well, that’s not true. I bought a house in Texas. I bought that one subject to and lost a lot of money, but I do intend to buy more properties in all states, really.

[Jeune Ortiz]
OK, OK. So how are you able to get money back? You’re getting in the truck driving.

Who knows where? And you’re going to you’re going to keep going because you have a partner. You have systems.

[Gabrielle Simmons]
No, just me.

[Jeune Ortiz]
Just you. OK, so then you must have great.

[Gabrielle Simmons]
Yeah. And I don’t do any like marketing anymore. So because of the platform I’ve built in my social media, I I get deals sent to me through Facebook and Instagram.

So I don’t really need a team anymore. But I’m also not looking to do a large, high scale of wholesale transactions or acquiring a lot more properties right now. I’m really taking things slower in the real estate space.

So I get a few referrals for deals every month organically through social media. But when I was, you know, operating at a higher level, I did have a marketing team of a. VA manager guy, several VA’s, you know, that were texting, cold calling, handling marketing, all of that.

[Jeune Ortiz]
OK, OK. So. So tell me your process that you’re doing.

[Gabrielle Simmons]
I just since I was started trucking, I just share a lot of personal and business stuff to my Facebook and Instagram. And it’s really worked. I was one of those people that was like, I hate social media, you know, and did not want that to be an important part of my business.

But then I kind of just embraced it and was like, well, let me let me give it a shot. Let me put some content out there. Let me post things about my personal life and my nieces and little sister that I adore.

And I don’t have kids, so they’re the closest thing for me. You know, let me post things about my personal life and my business and what I do and how I help people. And that has really just created an incredible opportunity to have people reach out to me with leads.

[Jeune Ortiz]
OK, OK.

[Gabrielle Simmons]
Motivated wholesalers. Definitely a lot of wholesalers, although most of those are not great deals that I’m that I’m then like, OK, guys, let’s let’s sit down. Let’s have a little coaching session real quick.

[Jeune Ortiz]
Right. Right.

[Gabrielle Simmons]
You’re not alone.

[Jeune Ortiz]
Yeah.

[Gabrielle Simmons]
And I get it, too, because I’ve been there. But mostly motivated sellers or people who are close to the motivated sellers, you know, might be their sister or cousin who’s my friend and then says, hey, you know, you should get in touch with my aunt because she could really use your help.

[Jeune Ortiz]
Fantastic. I love that you mentioned social support. I think what I like best is that you shared your life behind the scenes.

You know, you know, really person out in the world and behind that is the passion for helping people through real estate. Yeah. Always telling people who you really, really like.

It just turns a lot. They don’t want to know about, you know, constantly. You know, they want to know who you are.

[Gabrielle Simmons]
And how you’re helping people, like you said. Being relatable. Yeah, that’s the biggest thing, just being relatable.

[Jeune Ortiz]
Yeah.

[Gabrielle Simmons]
Yeah.

[Jeune Ortiz]
I love that. Yeah. All right.

[Gabrielle Simmons]
All right. I have done one burr, technically, with my ex-husband’s VA loan. We flipped it to hold.

That’s the only, well, and then the one in Texas. That was not intended to be a flip. I bought it subject to, and the intention was to keep it as my vacation home.

And that did not work out well. So I ended up flipping it and losing money, flipping that quickly. But otherwise, no, I’m not, I don’t consider myself a flipper.

[Jeune Ortiz]
Okay. Okay. You have a little bit of a projectile that didn’t go so great.

What would you say would be what you would consider one of the biggest failures?

[Gabrielle Simmons]
Definitely that. That deal, because to make a long story short, I didn’t do enough due diligence as the buyer, being out of state and being in a very small timeline to put it all together. I didn’t go and get additional bids for the foundation work that I should have.

And so what I thought was going to be a very small problem with the foundation ended up being over 50, 60 grand in work and way above my budget. Yeah. I do use private money lenders and use a private money lender to acquire that property.

And that was even outside of his budget at this point, because we were working on some other projects too. And it was just, we couldn’t make it work. So that definitely was a big failure, I would say on my part.

Aside from that, though, buying a property and doing what we all know that we’re not supposed to do. I wonder if you can guess what that is. The big thing we all know is they always say, don’t rent to family.

[Jeune Ortiz]
Yeah.

[Gabrielle Simmons]
That was actually financially, probably the biggest failure in purchasing a property and renting to family and helping take care of things at a much higher level than I should have.

[Jeune Ortiz]
That I just recently- Absolutely.

[Gabrielle Simmons]
Yeah. And so I had to have that tough conversation not too long ago. Actually, it was recently after a long time.

So another lesson learned for sure.

[Jeune Ortiz]
Okay. So lessons learned.

[Gabrielle Simmons]
I mean, we don’t know rent to family, right?

[Jeune Ortiz]
But then with the other deal, just more due diligence?

[Gabrielle Simmons]
Yeah, definitely more due diligence. And I think because I was looking at it like, it’s going to be my home. And the idea was to rent it as a Airbnb when I wasn’t there, because I love being in Colorado during spring and summer when the weather’s great.

Fall and winter, not my favorite. So the idea was to go down there to be in San Antonio during those months. And so I think because I was looking at it from a standpoint of like, this is home, it doesn’t need to be perfect.

I’m not trying to I wasn’t analyzing everything the way that I would if I was looking at it from a flip standpoint. Is this profitable on the back end? Yeah, definitely something I should have been doing is looking at the numbers differently.

[Jeune Ortiz]
Okay. How did you learn all this?

[Gabrielle Simmons]
What was your- So Google, started with Google when I was truck driving. And I was making really great money. I was 23 years old, owned my first business.

And as an owner operator with my own semi, I was making well over 100 grand a year and didn’t know what to do with it. I don’t come from a family of money or financially educated people as a whole. So I had no idea what to do with all this money.

I was taking trips to Dubai and flying my friends to Cuba and like, just blowing it. So I googled, you know, like, how to invest money in real estate. Because that’s just something I’ve heard.

I think we all have heard that, that the wealthy invest in real estate.

[Jeune Ortiz]
I came across- We’ve heard that a lot.

[Gabrielle Simmons]
Yeah. I came across Chris Krohn, who is an investor based out of Provo, Utah. And his thing at the time was just rental properties, acquiring rental properties.

And so I bought into his program. I paid a lot of money to become a platinum partner with his program and get access to his events and vaults that contained a bunch of, you know, recorded teachings and lots of great information. Still not exactly what I was looking for, though, because it didn’t help me, like, get my foot in the door, you know, to buy rental properties the way that it’s taught there.

You still need large lump sums of money to do so, which I didn’t quite have that much, you know, lump sums of money to buy rental properties, nor did I have the ability to qualify at the time because I just started a new business and, you know, qualifying for a bank loan, you need at least two years in the same same thing. So then that’s how I discovered wholesaling, you know, kind of going back to YouTube University, where I was watching Chris Crone’s videos. I started seeing things about wholesaling and really through YouTube University and BiggerPockets and, you know, these big platforms and websites and amazing podcasts like this one right here, I learned for the most part what wholesaling was and how to do it.

And then I learned how to do like how to buy property subject to I learned how to buy properties using seller financing. I bought several that way. And the Airbnb arbitrage just from people in my network that I offered my time to in some form or fashion, and they taught me, you know, the game, if you will, quickly, so I didn’t have to go back to buying into courses and mentorship to learn those things.

[Jeune Ortiz]
Yeah, I love that you have a strong network. That is so powerful and so important for investors, because I think a lot of investors feel like they have to do it all on their own. They’re afraid of a partner or their competitors, you know, and just spread so thin and trying to do everything that they can and get where they need to get.

Plus, as you said, it’s hard to be inverted in every every financing. And so if you build a network around that you that you learn from and that is just so powerful.

[Gabrielle Simmons]
Yeah. And with that, I’ll note that as a new investor, maybe we shouldn’t get so overwhelmed with the idea that like we always need to offer something. Yeah, you definitely should offer value of some sort.

Right. Nobody wants to be the hey, let me pick your brain for free kind of person. But I’ve seen a lot of my students who come to me and they’re afraid to build a network because they’re like, oh, I don’t know anything.

I don’t have anything. How can I how can I be of value to you? So I would just mention, you know, a couple of ways that any of the listeners can be a value one, you know, offer your time.

If you come across an investor who says, oh, yeah, I’m in the process of putting together an Airbnb. Oh, hey, I’m free this day, this time, whatever this block of time, I would be happy to come and help you set up, you know, setting up an Airbnb if they’re doing it themselves, which I do all mine myself. That’s a lot of work, putting together the furniture and all the staging and everything.

Just offer your labor to come help. Offer to make phone calls, offer to follow up on their calls, offer to get their coffee, you know, anything that you can do.

[Jeune Ortiz]
Yeah, yeah.

[Gabrielle Simmons]
Yeah. Yeah. Yeah.

[Jeune Ortiz]
Yeah. Right.

[Gabrielle Simmons]
Yeah. And like you said, bandit signs, that’s a, yeah, that’s a big one.

[Jeune Ortiz]
All right, so if someone wants to get involved in some of the same things, I know you’re very much self-taught, you put things together from a different person. What would be the kind of advice that you would give to somebody? Would you tell them to do the same thing, or would you recommend coaching or wouldn’t you?

[Gabrielle Simmons]
I feel like there weren’t as many resources when I was getting started in the wholesaling space that there are available now. So even, you know, not just talking about my courses and my coaching, there are lots of opportunities. There are lots of people who are coaching.

I do think that wholesaling is one of the best entry points to becoming a real estate investor. Even if you don’t stick with that route, I think pursuing the knowledge that you can get from wholesaling is very, very valuable no matter what strategy you choose to focus on. Yeah.

Yeah. So I do recommend coaching. I recommend not doing it on your own, especially wholesaling because you can get yourself in some trouble.

You can screw people over too. And that’s something that none of us want to do. But I recommend getting a coach and you don’t need to pay 10 grand to get one these days.

There are coaches that you can get in touch with and maybe you only talk for one hour a week. But if you dive in and you write your questions down and you’re very intentional, you can learn a lot, you know, during that time and not have to fork out a whole bunch of cash to do so. That’s what I recommend for sure.

[Jeune Ortiz]
That’s good. And you mentioned you had mentees. Do you understand that?

Is that part of your business?

[Gabrielle Simmons]
Yeah. So I no longer take on what I call exclusive mentees. So that’s like a much more in-depth program, higher cost.

I’m not currently accepting any exclusive mentees, but I do have my online courses that are, you know, pre-recorded courses that can be watched. And then with that comes, you know, a one hour one-on-one session with me and then access to my calendar to book, you know, periodic short phone calls. That’s the extent of my coaching opportunities that are out there and available right now.

[Jeune Ortiz]
Okay, so you are a coach.

[Gabrielle Simmons]
Yeah, yeah, I’ve, I’ve always done coaching. And even when I was in trucking, I was doing coaching, to some degree in just making YouTube videos. And I had my Calendly where people could book a private call with me and we could talk about it.

I don’t, I’m not a guru by any means, you know, I don’t, I don’t claim to know things that I don’t know. So in my coaching, I’m always just very transparent about like, you know, this is what I have done. This is what I have not done.

This is what I know. And you take this and go and make it bigger and better. You know, I do have about four years experience in the business as a whole and that and I’ve learned way more than I think a lot of people do because of how much I’ve built my network and mentored under other people who have been doing this as long as I’ve been alive.

So I’ve learned a lot in a short period of time. But really, my coaching is just to give guidance more so than like, it’s not the ticket to make you financially free. You got it.

You got to do the work to get there.

[Jeune Ortiz]
Absolutely. Anybody, anybody who’s going to be written is pulling themselves up and they’re going to be really good at it. So tell me, tell me where people can go to get their tickets.

[Gabrielle Simmons]
My website, Gabrielle-Simmons.com. Also, if Instagram is easier, my handle on Instagram is InvestorLadyG. And I do have all my links on there as well.

I do have a short, a mini course on Udemy. Think I’m saying that right? Yeah, I do have a mini course on there that’s about wholesaling.

Really, more so than anything, though, I encourage anybody who’s especially looking to get into the business or is already in real estate investing and wants to learn more. Definitely take a look at the creative finance course. Mine, somebody else’s, anyone’s, educate yourself on creative financing, because that is huge, especially in today’s market.

[Jeune Ortiz]
Yeah, yeah. So you have a lot going on. How do you stay motivated to come up with everything?

[Gabrielle Simmons]
I sleep a lot.

[Jeune Ortiz]
Reservations are important.

[Gabrielle Simmons]
And I really just, I have a passion for it. I’m naturally a workaholic. I think my mom is a workaholic.

I’ve kind of always been in that type of environment. We don’t know when to like, stop. And I don’t, I don’t have kids.

I’m single. So working, I get such a great sense of fulfillment from putting deals together and seeing businesses be profitable. So I just, I have such a passion for that.

It’s hard for me not to want to do it. But I also travel a lot. You know, I spoil myself with vacations.

And that keeps me going when I start to feel a little burnt out. Where’s your next trip? Costa Rica.

Oh, nice. Probably end of next month is what we’re looking at.

[Jeune Ortiz]
Okay, okay. So take a break. Take a quick trip.

[Gabrielle Simmons]
Yeah, because I think I’m gonna, we should have our trucks by the end of next week. And then I’m just going to drive every day until I go to Costa Rica. So three, four weeks of driving, and then take about a week off.

[Jeune Ortiz]
It sounds like you want to wake up. All right.

[Gabrielle Simmons]
All right. So I am, I just turned 29. I, my long term plan that I’m coming to the end of currently, it was a five year plan that I started when I was 25, to be retired by the time I’m 30.

So I have one year to and it’s a lot of pressure because I, I just like, I just kind of like, re did a lot of things in my business, you know, I got out of Airbnbs, and I’m, I’m looking to do more subject to use and midterm rental. So it kind of feels a little stressful, because I had a whole bunch. And then I’m like, pulling back to get heavy back into the market again.

So I have one year to get to where my passive income is at least $5,000 a month.

[Jeune Ortiz]
Okay.

[Gabrielle Simmons]
And I used to think like a lot of people may that we need 1020 grand a month to retire, or to be comfortable. And it’s definitely, you know, based on the individual, but my goal originally was 10 grand, I wanted to go hard in this full time until I could earn 10 grand a month passively. Now I’m like, five grand is really actually great, especially given my goals.

So for the next five to 10 years, my goals are to travel, I really just I want to travel, I will continue to be a resource for people in the real estate space with coaching. I’ll continue to do some wholesaling, I’ll continue to buy and hold, you know, maybe two or four properties every year. It won’t be at such a fast pace as what it has been.

But I want to travel the world and I want to go stay in places for like a month at a time. And live there, you know, be like a resident there. And probably start a YouTube channel and share that experience with the world and do that until I get bored, I guess.

[Jeune Ortiz]
And then you’ll maybe your plan. That’s fabulous. All right.

One last quick question, since you’re starting your business, what are you most grateful for?

[Gabrielle Simmons]
Oh, I’m so grateful for my time and the geographical freedom. It brings tears to my eyes often. When I think about, you know, just the freedom that being in real estate has earned me.

I mentioned my little sister, you know, she’s very heavily involved in sports. And she’s just crazy awesome kid. And so like, to have the freedom for her to say, Hey, sis, can you come pick me up from school and take me to this volleyball game?

Yep, I can I can do that. I can be there. There’s, there’s nothing tying me to an office, you know, or clocking into someone’s job.

I’m so grateful for that. You know, having family across the country that can say, Hey, you know, we’d love to have you come spend a week with us this summer, or this winter when and I can just say, Okay, you know, and I can still work, I can still earn an income and be anywhere. That is just the most incredible part of real estate investing.

It makes it all worth it.

[Jeune Ortiz]
I love I love that. It sounds like you’re living your dream.

[Gabrielle Simmons]
I don’t think so. I think we went over everything. I really enjoyed this, this podcast.

I can’t wait to see the other episodes as well. And thank you for having me. Absolutely.

[Jeune Ortiz]
It was a pleasure hearing you. And I hope to have you on the show again to see more of what you’re doing. Awesome.

[Gabrielle Simmons]
I look forward to it.

[Jeune Ortiz]
All right. Thank you for joining us on this episode. Remember to subscribe to the show on your favorite podcast app.

And if you want to know more information, visit unitedstatesrealestateinvestor.com for more podcasts and industry news.