How New Investors Can Buy Their First Rental Property and Build a Portfolio

Alisha Gillooly (00:00)
if you have somebody that wants to invest, they need to know those certain things. They need to know, they need to dive in deep. They don’t just need to know the surface level. Does it look nice? This is not. They need to know, is this going to be a good investment for my money? You know?

Scott Bursey (01:46)
back to the Real Estate Pros podcast powered by Investor Fuel. I’m your host, Scott Bursey. Today, we are thrilled to welcome Alisha Gillooly of Wynd Real Estate, a pro who is mastering the strategic blueprint for single-family buy and hold investing. Alisha is bringing the high octane fuel of international system building, showing us how to move from zero to generating consistent returns with discipline acquisition. Get ready to download the playbook, Alisha

is in the studio. Alisha, welcome to the show.

Alisha Gillooly (02:21)
Thank you, Scott. Happy to be here.

Scott Bursey (02:24)
It

is just awesome having you here. And for our listeners who may not be familiar with your journey, please give us the front row seat and how your career ignited and where are you putting the fuel right now?

Alisha Gillooly (02:38)
Yes, so my career ignited about five years ago where I was actively starting to sell ⁓ real estate. But I actually have been doing and involved in real estate for about 15 years on the backside with family and stuff like that. ⁓ And my career really took off when I did a major sale about two and a half or so years ago with Rick Ross and Meek Mill.

⁓ And I really dove in ⁓ completely at that point. was totally invested. yep. And now I’m here ready to share my knowledge with everybody.

Scott Bursey (03:18)
Awesome, awesome. That’s impressive.

And what really caught my attention about you was the way that you’ve been able to focus purely on the buy and hold strategy in single family residential investing. know, demonstrating the essential discipline required to successfully structure deals and build a long-term portfolio right from the one to three year mark. That’s pure investor fuel.

Alisha Gillooly (03:42)
Yes.

Yes. Yes.

Scott Bursey (03:45)
And

it certainly is not easy. So let’s dive into what we call the lightning round here, Alisha. What is the strongest principle guiding your current buy and hold strategy in your view?

Alisha Gillooly (03:52)
Okay.

I would say number one is the knowledge. You need to have a good amount of knowledge about what you’re doing, what you’re trying to do, what goes into everything, and that way you can be as successful as you can.

Scott Bursey (04:17)
That clarity of purpose is essential. You know, it’s very important to be focused and have those systems in place. You know, let’s shift gears just a little bit here. What’s the biggest time sink or bottleneck challenge, if you will, in your process right now? Something that you’re trying to conquer.

Alisha Gillooly (04:22)
Yes.

Right.

Back to the knowledge, I’m trying to get more knowledgeable on the credit side of things, kind of like the initial process with buyers that want to invest and ⁓ whatever that looks like for them. ⁓ Them having a hard time getting approved for the loan or securing funds. So I’m trying to get more knowledgeable with that so I can help my clients the best I can.

Scott Bursey (05:52)
Every pro deals with friction, know, identifying and eliminating bottlenecks in deal flow or financing is, how you unlock true growth. And on that note, what is your vision for, for the, for the long game?

Alisha Gillooly (06:10)
My vision for the long game ⁓ for me is of course to have a lucrative business where I’m getting a lot of sales of course, but I want to invest into a few things. I want to get an apartment complex and I want to also get a duplex. The duplex is going to be my first investment. ⁓ That kind of goes back to my childhood when I was helping my father ⁓ in his investments.

⁓ I want to get a duplex and then I want to get an apartment complex. So that’s the long-term goal for me.

Scott Bursey (06:44)
That’s awesome. And we spoke a little bit prior to ⁓ the show today. ⁓ Maybe give us an origin of your upbringing as far as the family business.

Alisha Gillooly (06:57)
yeah, okay, so I am from Seattle, Washington, the West Coast, and I was big into real estate with my stepdad when I was younger. He owned about five properties, ⁓ houses, and we used to work on them together. He really taught me a lot about what goes into owning a house and having ⁓ renters and, you know, we used to…

We used to drive by, pick up the rent every month. But ⁓ we also used to do like the electric electrical work, know, changing toilets, pressure washing. It could be anything. We were working on the house to save some money. And then the long, in the long run, like right now I’m looking back and even me living in my house, I’m realizing having that knowledge and knowing what to do around the house and not always having to call somebody, it saves a lot of money. So I’m always going to refer back to having knowledge.

⁓ That really helped me, shaped me today.

Scott Bursey (07:58)
You know, that hands-on knowledge is so critical. It really is. And how are you using that in today’s world?

Alisha Gillooly (08:05)
Yeah.

So for today’s world, I would say when I have clients and I’m able to show them the house, I’m able to walk around and give a lot more knowledge than not to toot my own horn or rain on anybody else’s parade. I’m able to give a good amount of knowledge that a lot of realtors wouldn’t be able to get because they’re not into it as much as I feel like I am or I was. ⁓ So yeah, I would say that.

Scott Bursey (08:40)
that it sounds to me like that deeper level insight is what perhaps separates you. Absolutely. And that is unparalleled. Now it takes, you know, it takes that, that knowledge and that vision. And that’s really what separates the average agents from the, from the rock stars.

Alisha Gillooly (08:46)
Deeper level insight, perfect, yes. Yes. Yeah.

if you have somebody that wants to invest, they need to know those certain things. They need to know, they need to dive in deep. They don’t just need to know the surface level. Does it look nice? This is not. They need to know, is this going to be a good investment for my money? You know?

Scott Bursey (09:16)
Now, if somebody is listening and they’re thinking to themselves, hey, this is somebody that I really like and I might want to do business with. What would you like them to know first about your business?

Alisha Gillooly (09:30)
⁓ I want them to know that I am very, very proactive. you know, aside from me being able to just get the job done, I’m going to have them walking away with the knowledge and make them feel comfortable about their by. I’m going to be waiting on them hand and foot basically, you know, whatever they need, whatever we got to do to get through it. ⁓ I’m going to be there. So.

Scott Bursey (09:53)
It sounds to me like customer service is ⁓ one of your main focuses and I couldn’t agree more. Where’s the greatest overlook?

Alisha Gillooly (10:01)
Yeah, yeah, a lot of people

are scared. A lot of people are scared, you know? So having somebody that has, you know, number one, the knowledge and makes them feel comfortable and to where they’re walking away with some knowledge and happy about the buy again, you know, that’s, that’s, people need that.

Scott Bursey (10:51)
Absolutely. And we spoke of this as well prior to the show, but playing to win, not playing not to lose.

Alisha Gillooly (11:02)
Exactly.

Scott Bursey (11:04)
And where is the greatest

overlook opportunity for acquiring stable SFR rentals today in your view?

Alisha Gillooly (11:14)
say a big opportunity right now I would say to buy and hold and you know either put a tenant in there or you know maybe get a duplex and live in one side have a tenant living on the other side pay off the mortgage do it again be able to pay off that loan and move on to the next house maybe keep doing that or then buy your dream home so I would say to buy and hold and have something working for you right now

Scott Bursey (11:41)
That philosophy there really keeps you ahead of the curve. Now let’s rev up the engines here a little bit. What’s the biggest operational risk when managing your first few buy and hold assets?

Alisha Gillooly (11:48)
Yeah.

I would say the biggest risk of what I’ve seen is stuff happening that you never knew was going to happen. ⁓ Stuff breaks, stuff, the market crashes, this, that. There’s stuff that you aren’t going to know, but you just have to weigh your options and know when to just jump in and take the risk.

Scott Bursey (12:21)
Having proactive systems in place is so critical. It really is. And that is so important to be able to continue to scale. What is the single most important metric you use when analyzing an SFR property for long-term hold?

Alisha Gillooly (12:26)
Yeah.

Right.

Yeah.

I would just say I do a lot of research, FMLS, MLS, stuff like that, discuss with my brokerage. Yeah.

Scott Bursey (12:54)
Absolutely. What do you feel is the biggest opportunity out there right now in your markets? Now, I understand that you are in Georgia. Maybe you can expand on that just a little bit for us, Alisha.

Alisha Gillooly (13:10)
So some opportunities that are coming up that I know about, would say, what is it called? The World Cup is coming up. FIFA, I think, is coming here. I think it’s something like that. I would say if you have ⁓ a property right now, an extra property lying around or whatever, it’s time to put it on the market ⁓ for having a short-term lease right now. That’d be a good thing right now.

Scott Bursey (13:37)
Okay, yes. ⁓ Right there, that vision is on point. Okay, Alisha, it’s time for the money question. This is where you supply the high octane fuel for our pros. For our listeners who have done all the studying and planning, just like you, but still are stuck trying to secure their first high quality single family buy and hold property,

Alisha Gillooly (13:38)
Prices are going to go up for this, you know.

Okay.

Scott Bursey (14:04)
What is the best action they should take right now to secure that initial deal and ignite their portfolio?

Alisha Gillooly (14:13)
The action I would say is to put themselves out there, ⁓ to actually go through with everything. ⁓ As far as like realtor standpoint for their client, I would say for them to cross all their T’s and dot all their I’s and make sure that they have the funding, they have the knowledge and they go in for it. Yeah.

Scott Bursey (14:37)
Alisha, you just dropped a goldmine of value for our listeners. Thank you for that, but we can’t let you go yet. What additional advice could you give to our listeners today?

Alisha Gillooly (14:52)
So on the real estate side of things, would say if you’re trying to secure an investor, ⁓ really put yourself out there and show them that you have the knowledge and you can help them ⁓ get a return and ⁓ market yourself. Make sure that you let everybody know what you do and ⁓ just put yourself on the forefront. Nobody is going to know what you do until you let them know. So that’s the biggest thing to secure.

some deals.

Scott Bursey (15:23)
And it’s really

about serving others, isn’t it?

Alisha Gillooly (16:07)
It is. That’s the main thing. That’s the main thing is serving others, whatever that looks like.

Scott Bursey (16:10)
Absolutely.

And for our listeners who would like to follow your journey or collaborate with you, what’s the best way for them to reach you?

Alisha Gillooly (16:21)
They can reach me at [email protected] or they can reach me on social media @TheOfficialAG. Yep, that’s on Instagram and pretty much across all platforms.

Scott Bursey (16:34)
Alisha, this has been pure gold. Thank you for joining us today.

Alisha Gillooly (16:40)
Thank you so much, Scott. I appreciate it.

Scott Bursey (16:42)
And for our listeners, we appreciate each and every one of you. If you got value from today’s episode, please subscribe. We’ve got a lineup of exceptional guests, just like Alisha, who are making huge moves in the market. Until next time, keep your standards high and your vision clear. We’ll see you on the next episode, everyone.