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Real Estate Pros · September 29, 2025 · 22 min listen

How to Set Realistic Expectations as a Real Estate Investor

With Armando Hassey

Show summary

In this episode of the Real Estate Grows podcast, Kristen interviews Armando Hassey, a seasoned investor and realtor from Florida. They discuss Armando’s journey into real estate, the importance of understanding market expectations, and the current landscape of the real estate market. Armando emphasizes the significance of building a strong network and learning from challenges faced in the industry. The conversation concludes with insights on community support and the importance of instinct in making investment decisions.

Key takeaways

  • Armando's core philosophy: there are no bad investments, only wrong expectations. The job is to match an asset to an investor's actual goals.
  • To set realistic expectations, ask why and how you're investing: extra cash, offsetting W-2 tax liability, or building long-term wealth. The answer determines what kind of deal fits you.
  • Real estate is a 'steady eddy' asset class, not a get-rich-quick vehicle like Bitcoin. You put the chips in play and let time do the work, but you also don't wake up to your asset being worth half overnight.
  • Separate residential from commercial, and even separate markets by zip code or side of the street, before analyzing what's happening in 'the market' as a whole.
  • Affordability today is driven by more than interest rates: property taxes, insurance, and HOA fees combined have nearly doubled the cost of owning in some cases, affecting investors, move-up buyers, and first-time buyers alike.
  • You don't need to be an expert in everything; you need to be an expert at identifying the right professionals (agent, attorney, accountant) and building relationships with them. Example given: a good accountant can flag real estate professional status and bonus depreciation on a short-term rental to save tens of thousands in taxes.
  • Find trusted professionals through podcasts and books consumed as audio during drive time, plus your existing network of contacts who can make referrals.
  • Have an attorney review contracts before funding a deal, not after. Armando and his wife funded a development where the developer tried to undersell the finished property to someone else for more money after years of funding it; earlier legal review wouldn't have prevented it but would have flagged the risk.

About Armando Hassey

Armando Hassey is an investor and licensed realtor based in Wellington, Florida. He started buying investment property with his wife around 2013 while running businesses in the equestrian world, and later got his real estate license after finding agents in his area too focused on big farm clients to serve his needs.

Listen to the audio

“There are no bad investments, in my opinion. There's just wrong expectations.”

Armando

“It's not a one time get rich situation. You're not buying Bitcoin and waking up in the morning and now it's... at the same time, you also are not going to wake up and now your Bitcoin is worth half.”

Armando

“We arrived to the Holy Land and we missed it by like a day or two.”

Armando
investor expectationsFlorida real estatebuilding a professional networkresidential vs commercial marketaffordabilityreal estate professional statusdue diligenceoff-market development deals

Questions answered in this episode

What's the biggest mistake real estate investors make, according to Armando Hassey?

He says there are no bad investments, only wrong expectations. Investors get into trouble when the asset they buy doesn't match what they actually need or want, and the fix is to clarify the why and how of an investment before buying.

How should investors think about today's affordability problem?

Armando says affordability is hitting everyone, investors, move-up buyers, and first-time buyers, and it's not just about interest rates. Property taxes, insurance, and HOA fees combined have made owning a home cost almost double what it did a short time ago.

Should real estate investors try to learn everything themselves?

No. Armando says you don't need to be an expert in every part of a deal, you need to be an expert at identifying the right people, like a real estate agent, attorney, or accountant, and building relationships with them. He gives the example of an accountant flagging real estate professional status and bonus depreciation on a short-term rental to save significant tax dollars.

How can new investors find reliable professionals to work with?

Armando suggests listening to real estate podcasts and audiobooks during drive time, since they often include contacts and links to professionals. He also recommends going through your existing network of contacts for referrals, since people who work in real estate are usually willing to connect you with others.

What happened when Armando funded an off-market development deal?

He and his wife funded the development of an off-market property, but the project was delayed for years, and when it was finally finished the developer tried to sell it to someone else for more money than the price he had already agreed to with them in contract. Armando says he should have had an attorney review the contract at the start to understand the risks going in.

Resources and links

Full transcript

Armando (00:00)

I think so. Yes. And what I see the biggest mistake with investors is there are no bad investments, in my opinion. There’s just wrong expectations. So when you have, when you really understand the expectations of the investor, then, you know, the job of the other side is to try to match an asset or a, you know, that matches those expectations. And as long as that is aligned,

Kristen (00:11)

Right.

Armando (00:26)

You know, people are always happy. The issue that I see is when those expectations are not aligned with that asset. And, you know, I think that’s the biggest mistakes things people do.

Kristen (00:29)

Right.

break.

Welcome back to the Real Estate Pros Podcast. I’m Kristen and I’m here with Armando Hassey, who is an investor and realtor out of Florida. Thank you for being here, Armando.

Armando (02:19)

Of course,

Kristen, thank you for having me.

Kristen (02:21)

Amazing. So you have a really well-rounded, you have well-rounded experience in the industry and I want to get into all of that. Let’s first start how you got into this industry to begin with.

Armando (02:30)

Sure. Yeah, well, I’ve always been an advocate for real estate. I always remember my grandma telling me, you know, buy your first house, buy your house. so since I was young, I had that little bit of idea in my head. And my background was more in the question world. So when I was growing up, I wanted to be in the Olympics and, you know, be an international question writer. And I’ve achieved some of those goals. But along the way, I

Kristen (02:53)

Yeah.

Armando (02:57)

I started investing in real estate. So I think our first investment property is when I met my wife. Well, now my wife. We were dating at the time and we bought a house. I think that was 2013.

Kristen (03:11)

Amazing.

So this was kind of like a side thing in the beginning.

Armando (03:14)

At the beginning, it was more of a side thing. Yes, it was like I was so focused on the horses and the riding, but I always had that real estate bug. Then I started a lot of different businesses around the question world, but we kept acquiring slowly another property and another property. then, yeah, right after COVID or around the COVID area, I wanted to do more, but I always depended on a real estate agent.

Right. And a lot of the area where, where I am at in Wellington, which is a question world, a lot of those real estate agents are so busy with bigger clients, you know, with big farms and big ticket. So, so they, felt they never put a lot of attention to my needs. Um, so I’m like, okay, I got to jump to, know, how can I, how can I do it? And so I decided to get my license and that way I was able to, you know, get in first place now. So I could go and see what properties are out there or, know, I could do it for myself.

Kristen (04:06)

Yeah.

Totally, I’m sure that just streamlined your whole operation, made it way more efficient.

Armando (04:14)

Correct. It made it a lot more efficient. I also like to, when I invest in something, I like to understand it. So I think the main thing is it made me focus on it and it made me put a lot of attention and make me read a lot of books and start to get knowledge. So I would say it’s not just the license what makes it, it happen. It’s more the license and then the desire to learn more, you know.

Kristen (04:38)

Absolutely, absolutely. And then, you you get to help so many people also. Like in your real estate journey with being an agent, you get to help other people acquire wealth and acquire equity.

Armando (04:50)

I think yeah, there’s a lot of different ways you can help people. know, from even having a friend, helping him get a good apartment, you know, for rent, or ⁓ find somebody that wants to invest and give him good advice on why you should not invest in that HOA or just open their eyes, To also have a family find a beautiful home for the next, you know.

Kristen (05:09)

for that.

Armando (05:15)

10 years of their life. So there’s a lot of different areas where you can help people.

Kristen (05:19)

Yeah, and I’m sure you being an investor yourself, when you come in contact with investors, you’re able to really help them because you understand kind what people are looking for.

Armando (06:16)

I think so. Yes. And what I see the biggest mistake with investors is there are no bad investments, in my opinion. There’s just wrong expectations. So when you have, when you really understand the expectations of the investor, then, you know, the job of the other side is to try to match an asset or a, you know, that matches those expectations. And as long as that is aligned,

Kristen (06:28)

Right.

Armando (06:43)

You know, people are always happy. The issue that I see is when those expectations are not aligned with that asset. And, you know, I think that’s the biggest mistakes things people do.

Kristen (06:45)

Right.

break.

What, like how do you even manage or develop your expectations? What do you think is practical and what do you think is too much?

Armando (07:03)

I think for me to manage the expectations is really going into why and how and the reason why are we investing or somebody is investing. Are you doing this because you have extra cash? Are you doing this because you want to offset some tax liability that you have? No, I see that with a lot of W-2 income earners. Are you doing this because you want to build wealth?

finding those reasons and a lot of the times we just need to ask ourselves the why and the how and then if you get those answered then I think it’s very easy to get some real expectations of what you’re looking for.

Kristen (07:40)

Right. Yeah. And I think it’s important because I think a lot of people, especially starting out and investing, they know they want to make money, but getting into that granular of why are you doing this? How are you doing this? What are the expectations? I think that a lot of times gets lost in the process.

Armando (07:58)

Yes, yes,

it gets lost and I think every course or every social media guy out there, they also sell you a dream, right? And they’re like, oh, financial independence and own real estate and you’re gonna, you know, having your yacht and your airplane and, you know, the time for yourself. And even that that is what we’re looking for in a way, it’s not that quickly.

It’s for me, I see it as a very steady eddy thing. And if you put the chips in play and you let the time, you know, do its thing and let those chips do what they’re supposed to do, then it’s very easy to get where you want to be. But it’s not a, you know, it’s not a one time get rich situation. You know, you’re not buying Bitcoin and waking up in the morning and now it’s, you know, now at the same time, it’s a very, I think it’s a very safe.

Kristen (08:38)

Yeah.

Armando (08:50)

asset class to invest because of those reasons. You also are not going to wake up and now your Bitcoin is worth half. So it kind of works both ways.

Kristen (08:58)

Yeah, and I would love for you to kind of expand on that and talk about just the market in general and what you’re seeing with it. I know there’s a lot of people, there’s a lot of information being thrown out and I think some people are a little cautious to enter the market right now and I would love your perspective on that.

Armando (09:13)

Yes, of course. mean, I think we hear it everywhere now. And there is one, I guess the main thing is to separate residential from commercial. And I think that’s the first mistake a lot of the people do is they put their real estate market in one big basket. And in reality, there are very different segments and different, even zip codes, right? Or sometimes even just in front of the street is a whole different market than on this side of the street.

really understanding that you have to separate real estate to exactly what type and location you’re talking about. think that is key. And then, you know, so after that, once you’ve, you know, identified what you’re talking about, then you can actually start analyzing, okay, what is happening in that market. Today,

Yes, affordability is, think, a huge issue, especially in the residential. So if we jump into the residential, affordability is affecting everybody. And it’s affecting investors, it’s affecting people that want to sell their house and buy a bigger one. It’s affecting new first-time home buyers. So I think across the board, we’re getting hit by affordability.

When you talk about affordability, it’s not just the interest rate, but it’s your property taxes, your insurance, your HOAs. When you do a whole picture, then all of a sudden, owning a house has almost doubled in just a few amount of time.

Kristen (11:13)

Absolutely, and you know you’re spot-on with the affordability being the biggest issue So even more reason if you have the means and the funds to get in the market. It’s probably a great time

Armando (11:24)

I think, yeah, as long as you have the right expectation, I do think it’s a great time. again, I think one thing we all forget is we don’t need to be experts in real estate about everything. There is a huge network of professional people that are there to help you. So I think the key is to being an expert in identifying those people.

And if you can make relationships with those people, then you definitely have the upper hand on finding a great investment for you. yeah, mean, whatever it is that you really, whether it’s a real estate agent or an attorney drafting some documents, maybe finding a seller finance situation or an accountant, right?

And if you have a great accountant that cares about you, they can tell you, hey, if you qualify for real estate professional status and you get a short term rental for a year, I can save you, you know, with the bonus depreciation, you know, $50,000 in your taxes. And you’re like, wow, why nobody has told me that. Right. And so don’t try to know everything. Try to find the people that do. And then you can you can jump.

really big step.

Kristen (12:38)

Yeah, I bet. I mean, I think that’s such great advice. And what’s your best, what are your best tips on finding the right people? I think that it’s kind of hard sometimes to find someone who’s, you know, really aligned with your own goals.

Armando (12:50)

I think that’s where your focus has to jump in and, you know, understanding what you want to do and say, hey, I need a good accountant. And I would suggest start listening to some great podcasts. For example, there’s amazing, amazing information out there. You know, start finding a few and it don’t have to be really hard books. Just, you know, and you don’t have to sacrifice your time. I always say you can.

you know, whether you’re driving your kids to school or to soccer, or you have a road trip, you just put the book on and, you know, make it an audio book and, and you’ll be amazed how much information there you find. And a lot of the times, they are all the links to reach out to those people. And then the other part is just the people that you know, I’m sure if you go through your Rolex of contacts,

You know, you’re like, that guy’s in real estate. I’m sure if you give him a call, he can direct you to some great referrals. So I think just grinding your network and your sphere of influence, and they’re out there and they’re eager to help, right? Because that’s what they do. And I think at that point, it’s just, can you find

Kristen (13:46)

Absolutely.

Armando (14:42)

I don’t want to say good one because maybe they’re all good. But can you find, know, then your job is finding the best one that works for you. No.

Kristen (14:49)

Right,

Definitely. And getting the right questions, being clear again on your goals and seeing if they align. And how important was that for you as you were starting your real estate investment journey? Like how did you navigate that? Did you have a community? Did you have mentors?

Armando (15:04)

I’ve had a lot of great advice, yes. Throughout my career, like I used to train clients on my horse career. And then I made a few of the people that I used to train or their husbands or their fathers or they were in the real estate world. So I certainly, you know, when I had all the knowledge that I acquired with the podcast and the books,

then at least I could follow up those conversations with somebody in the industry. So I certainly reach out to everybody and I still am, you know, I don’t want to say I’ve achieved it. No, I constantly I am looking who is there that is in the space and who can I learn from? yeah, I just you have to do it all the time.

Kristen (15:45)

So.

Absolutely, and I think that, you know, as you’re starting out, again with expectations, I think maybe there’s an expectation that it’s gonna be smooth and easy and everything’s gonna always work out. Can you talk about maybe a time where things didn’t go as planned and what you learned from it?

Armando (16:04)

Of course, yes. If you’re a real estate investor, unfortunately, you’ve had some of those experiences. And it comes with the territory. I give you, me and my wife, we located some off-market properties that were going to be developed. And this was a very interesting story because we

jumped into the development and we basically funded the development for somebody and in the process it not just got delayed the development but the person that was doing the development he tried to under sell the property to somebody else so it was a very unique situation because we were you know we were already funding this project for

years and then all of a sudden it got delivered, you know, finally. It’s like, we arrived to the Holy Land and we missed it by like a day or two. Sorry, we almost missed it by a day or two and he tried to undersell it to somebody else for more money than he had agreed to or sign a contract with us. So, you know, I tell people this was my thesis of real estate investments.

Kristen (16:46)

Wow.

you

Armando (17:09)

You know, and getting, I was able to find some great attorneys in the process and understanding how the public records and the liens and the clouding titles and we learned a lot in that project.

Kristen (17:23)

Absolutely, and how do you prevent that from happening again?

Armando (17:26)

You know, I should have had an attorney review the contracts at the very beginning and not that they would have changed it, you know, I think just because they would have opened my eyes to where the risks are, right? Kind of letting you know where the boogeyman can come in. And so at least you are prepared if it arrives, no? So I think just being a little bit more

Kristen (17:41)

again.

Armando (17:48)

Yeah, finding a little bit more of that knowledge to lean on.

Kristen (17:53)

Yeah,

and I think just being comfortable in the uncomfortable and expecting the unexpected I mean when you’re first starting out that’s not really a muscle you have but I think working that muscle makes it easier to bounce back every single time because some of the stuff is unavoidable sometimes stuff just happens Yeah

Armando (18:08)

Correct. Correct. And people are people, right?

And things change in life. And I think in real estate, it has big financial commitments. That’s the main thing, Yes, you can do it with a little bit of money, but at the same time, there are big commitments of money. So at the end, the bank is giving you the money or a hard lender or your family members or so.

Even that you can do it with not a lot of money, it represents a lot of money, right? And people’s lives change and projects go south and the contractors do mistakes or don’t show up and people screw people, you know, it’s just part of what happens. And I think it happens in everybody’s life. It’s just the scale is so less. I don’t want to say important, but you know, it represents a lot less.

not just financially but also emotionally. Like every time you go on a project or you invest a lot of time and energy and effort and maybe you had some arguments within it so you’re very invested in it. So when something goes bad, it kind of drags you with it.

Kristen (19:15)

Absolutely, absolutely. Well, you’ve given us such good advice on the market, navigating it, starting out in investment or real estate investing. Tell everyone where to find you and how to work with you.

Armando (19:26)

Well, you know, the best thing, I mean, I have a website is ahassey.me. you can find my information there, but you know, you can find me on social media as well. My Instagram or my Facebook. I can, I can give them to you if you want. but really the best thing is to give me a phone call or a text message. Right. I’m always with my phone. So I think that’s the easiest way. And, and I will love to help somebody that wants to.

start investing or if somebody is already an investor and we want to align minds and strategies, I would love to do that as well.

Kristen (19:56)

Yeah, yeah, that’s what I love about the community. It feels like people really genuinely want to help others.

Armando (20:02)

I believe so, you know, or that’s how I am. And, you know, I’m sure there’s somebody that not, and that’s where, okay, at the end, you, got to develop that instinct, no, as an investor or even in business, right? You just got to have that instinct of is this guy the right person for me or not?

Kristen (20:19)

Absolutely. Well, thank you so much. I mean, I encourage everyone to go check out Armando and you know, if you’re in the Florida area, please definitely reach out to him if you have real estate needs. Thank you so much for being here.

Armando (20:30)

No, thank you, Kristen. This has been a pleasure and yeah, I find it very, how can I say, thank you for basically for allowing me to do this.

Kristen (20:43)

Of course. Well, everybody, thank you so much for listening. We hope you learned a lot, got some inspiration, and we’ll see you back next time. Bye.

Armando (20:51)

Sounds good. Thank you, Kristen.

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