How to Choose Real Estate Investments That Match Your Personality

Christopher Angelo (00:00)

honestly, if I get something, I probably never even sell. Like, I don’t even believe in selling anymore. Every house that I sold, I regretted at some point. And every house I didn’t buy when I could’ve, I regretted it.

That’s why it’s like if I see something I like it, I want I could buy it. I’m buying it.

If I like something, I have a good eye for it to go up in value, I feel like. So that’s why I don’t even second guess it anymore. If I like it.

It’s a good location, the vibes are right, I’ll buy it and I’ll just hold onto it.

Micah Johnson (02:06)

Hey, everyone. Welcome to the Real Estate Pros podcast. I’m your host, Micah Johnson. And today I’m speaking with Christopher Angelo, who’s been making some serious moves in the short term rental space for quite some time now. Christopher, welcome in, man. Glad to have you.

Christopher Angelo (02:19)

I’m glad to be here. Thanks for having me on the show.

Micah Johnson (02:22)

Absolutely, man. I’m excited for today’s talk. think our listeners are going to take away some valuable information. We had some good conversations in our pre-call recording. I’m pumped to unpack. So let’s dive in there. For someone that may not know you yet, what’s your main focus right now and what markets you currently operate in?

Christopher Angelo (02:40)

Well, mostly United States right now I have a few different Airbnb’s in on the East Coast and I want to work on making them more destination Airbnb’s short-term rentals maybe up to a month sometimes but essentially that’s my main focus although I do have I guess a sub a second focus which also just

adding different bigger properties, multi-families under in a portfolio just for cash flow.

Micah Johnson (03:13)

Gotcha. So a long-term hold concept and then some short-term rentals for things going on right now. Now, what is it about short-term rentals that interested you? Why that particular asset class?

Christopher Angelo (03:24)

Well, in the beginning, this is when Airbnb just became, you know, like just started. It was probably like 10 years ago and I was just renting to either normal people or college kids and there was this gap. There was this big gap during the summertime and during the holidays where the kids would go back.

Micah Johnson (03:48)

Got you.

Christopher Angelo (03:48)

you know, home

and they wouldn’t be there and they didn’t want to pay rent. So I’m like, OK, what is this Airbnb thing? So I started renting on Airbnb and it was like it was like in the beginning it was like 10 times or five times, five to 10 times as much in that month just from renting on Airbnb. It was like crazy. And I was like I was going overboard with like renting by the room, renting the whole place like.

Micah Johnson (04:08)

Wow.

Christopher Angelo (04:15)

whatever way I could put it to like cashflow on every property that I had access to. So that’s kind of like what I did in the beginning of Airbnb. ⁓ and I started using the app as I traveled, right? So now I got to see how it was to live like a local in this country, in that country, in this area. And I’m like,

Micah Johnson (04:27)

Man, good.

Christopher Angelo (04:40)

And this is really cool. So I really support the app. Like I love Airbnb and the life I’ve been able to live because of Airbnb.

Micah Johnson (05:38)

It revolutionized the way we move around the whole globe, man. It was a powerful creation that also created a great platform for real estate investors to start capitalizing on a market that no one had really thought about before. There was like word of mouth vacation rentals, other different things to do it, but truly bringing a concept to life of you don’t have to stay in hotel. You can actually enjoy the local area, see what it’s like to be there, actually feel the vibe of the city, not just be a tourist in it.

And it does, it revolutionizes this thing. And you’re in a very particular one that you’re interested in, which is that particular, the destination Airbnb, where there’s a whole experience that you’re trying to build in one of those. What led you down that route? What lights you up in that project?

Christopher Angelo (06:07)

for sure.

I guess it’s just kind of an expansion of when you go somewhere, right? You know, what places, what’s the hot spot like restaurant or like coffee shop or tea shop? You know, say for example, I never knew I liked tea that much. Like coffee is okay, but like there’s this amazing tea spot and they have a bunch of them in Asheville. I don’t know if you’re familiar with Asheville. It’s called Dobra.

Micah Johnson (06:29)

Mmm.

OK. Yeah.

Christopher Angelo (06:53)

And I just, I love the environment. They make the tea. Like I have my favorite tea maker. I’m not sure what to call her or something. And she just makes it like perfect every time. I know if she’s there, it’s going to be like the best tea. And it’s like, it’s like a black tea. So then I have an amazing, like very smooth focus and I could work for a few hours and be like extremely productive.

and it’s just a little bit of tea and a great vibe, you know? And that’s like something like, if you like tea, like that’s something that you should experience as a local in that area, you know? So that’s kind of like stuff like that. It’s a little bit bridge. It’s not just staying there. It’s like, okay, what are the coolest spots that maybe I like in that area that I would recommend to someone?

Micah Johnson (07:35)

Gotcha.

Right, it’s way more experiential driven. The actual what it’s, not just come stay, but while you’re here, this is the experience you’re trying to create for somebody where they walk away from the trip with that fullness, that memory, the desire to come back, that feeling of actually connecting with the place you’re going to, not just watching it from the outside.

Christopher Angelo (07:54)

Mm-hmm.

Okay.

Exactly. Yeah. Airbnb kind of like started, they have the experience tab. I haven’t really messed around with that because I’m not sure if it’s too connected with like the actual hosts in that area or something like that. But ⁓ I’m still testing it out. It’s still more of a experiment type thing that I had an idea that I was like, OK, let’s let’s do it. So.

Micah Johnson (08:44)

Gotcha. Well, what led you to real estate to begin with? You said you’ve been in it about 15 years now,

Christopher Angelo (09:25)

That’s a good question. Well, there was a property next door for sale and I had a college fund at the time. My mom’s like, oh, if you don’t buy it, I’ll get it. So I was like, all right. So I put pretty much all my money into that property and instead of like using it for college and then just started like I had this thing, you I had this house that I really never lived in that long. Like maybe here and there I stayed for a few nights, but

Then I was like, all right, how can I make money from it? And that’s kind of like how it happened. pretty much. Pretty much.

Micah Johnson (10:01)

One thing led to another, man. That’s the nature of estate. I love hearing how people

get into it. I was talking to a lady earlier. She was 17 and bought her, actually her mom gave her a house and that’s what led her to it was, okay, I’ll let someone live in this house and then I’ll let them rent it out. And then like it leads you into this, wait a second, there’s a lot I can do in this industry. And one of the things I enjoyed about our pre-talk is,

Christopher Angelo (10:13)

⁓ good.

Micah Johnson (10:26)

One, you’re doing it in a way where you’re not losing yourself. There’s an artist side to you that we’ve talked about this other section where real estate is very effective in letting you be that real person, even in doing the work that you’re trying to do. What value have you found there just for yourself and then able to share it with other people?

Christopher Angelo (10:45)

⁓ I think it’s the, cause like Airbnb doesn’t tell you how your house has to look. They don’t tell you how you can decorate it. They don’t tell you this and that. It’s more of a like, you have the you have the power of being able to like decide what it looks like inside the interior design, like ⁓ how the check-in process is, that kind of stuff.

Micah Johnson (10:52)

Hmm.

Christopher Angelo (11:15)

I, it was very difficult for me to ⁓ have a job where everything was preset. Just because I’m a very creative and expressive person. So it allows me to, to do that with Airbnb. So that’s, that’s.

Micah Johnson (11:32)

Which again, man,

it lines up with real estate in general. One thing I like to say a lot on this show is finding your way inside the industry. Real estate’s a big umbrella. There’s room for you to be exactly who you are and still use one of the most powerful tools in America to guarantee cashflow, generational wealth, to make sure you’re living, able to live that life that you’re trying to live.

What’s been some things you’ve done along the way that have helped you stay consistent and remain disciplined and in the game?

Christopher Angelo (12:02)

don’t think I really, I really, you mean like not getting away from real estate?

Micah Johnson (12:07)

Right, yeah, like what’s kept you coming around?

Christopher Angelo (12:08)

I don’t know, just,

it was just, it just worked for me. Like, I don’t know, I just never had an idea to get rid of it or anything like that. Like now,

honestly, if I get something, I probably never even sell. Like, I don’t even believe in selling anymore. Like after this, I sold a few houses. Every house that I sold, I regretted at some point. And every house I didn’t buy when I could’ve, I regretted it.

That’s why it’s like if I see something I like it, I want I could buy it. I’m buying it. You know, it’s like it. I mean, this goes back to when I was younger, too. So I don’t know if you heard of you know about the Pokemon Charizard card. The first edition one. So it’s worth, I don’t know, between 100, 200, 300000 depending on the grading. But there was one at the local shop for sale.

and I wanted to pull it from a pack and I pulled one from a pack, not first edition, but I should have bought that first edition one and I was like obsessed about it. I’m talking about like every day I’m thinking about it and I always use that first. If I like something, I have a good eye for it to go up in value, I feel like. So that’s why I don’t even second guess it anymore. If I like it.

It’s a good location, the vibes are right, I’ll buy it and I’ll just hold onto it.

know? Cause it’s a good thing. Like people try to tell me to sell my car like after it got a certain mileage and I’m just like, I’m not selling them. Like, I’m just sorry. Sorry if like you want someone to buy them, you don’t want me to have them or something. You know? Like I’m just, I want to keep it. Like I just want to keep it. So that’s kind of how I approach it.

Micah Johnson (13:57)

Right.

And again, you’re more of a collector. You’re creating the experience that you want to create using whatever medium that you feel like using. Again, another thing I love about real estate, it leaves your autonomy in place, right? There’s smart ways to do it. Make sure your numbers pencil. Don’t take risks that knock you out of the game. But at the same time, don’t become boring unless that’s what you’re trying to be, right? If that’s the business you’re trying to build or

Christopher Angelo (14:02)

Exactly.

Micah Johnson (14:26)

make it sure

Christopher Angelo (14:26)

boring.

Micah Johnson (14:27)

it lines up with what it is that you’re trying to do. Because heck, right now you’re not even at home right now. You’re out in Arizona checking out something else.

Christopher Angelo (14:35)

Yeah, exactly.

Yeah. Yeah, I haven’t been home in a while, honestly. I’ve been checking across ⁓ properties all across, you know, United States for a few months, actually. I’ve just been kind of shopping, seeing how the economy is going, how the people are in the town, and seeing if it’s a good long-term play, that kind of thing.

Micah Johnson (14:38)

Right, man, leave it.

And that’s something I want to shine a light on real quick for everybody out there. What you’re describing isn’t being willy nilly, isn’t like being random. It’s being intentional. You’re actually putting the time in to go to the places to see one, is this where somewhere I’d even want to own a property? Is this what I’m looking for? Is this that vibe that’s, there’s a vision that you have in your mind that you’re making sure things fit that vision so that you don’t get distracted out into stuff that I don’t want to do. Cause

It’s easy for investors to be like, okay, there’s a deal I’ll buy it just because I just want to buy a deal versus I want to buy a very specific deal. What’s that deal that I want to go buy, man, and good job on getting out there and putting yourself in the places where it’s not just based on nothing. It’s real boots on the ground, eyes on the property. This is something I actually want to do. And in the end, that lines up a lot with your collector’s personality.

Christopher Angelo (16:19)

and

Mmm.

Micah Johnson (16:41)

Right? Where it’s

more about the vibe, more about the property itself, more about the vision for it than just about cashflow and just about the numbers that it’s going to do. It will do those things. Yes. But it has to check this other box too.

Christopher Angelo (16:56)

Yeah, I realized that ⁓ investing is very personal. Right. People ask me, what should I sometimes they ask me, what should I invest in? Should I do real estate or should I buy some stocks? Or because I was also in the crypto a little bit back in the in the booming days, more of like the booming days. And I would trade crypto. I wasn’t much of a hodler. You know, I would do more of like swing trading. That’s what I realized, because like, I don’t know, I

Micah Johnson (17:01)

Mmm.

Christopher Angelo (17:25)

I guess because it’s only been around for that it hasn’t been around that long and also stock market hasn’t actually been around that that long. Like in terms of the span of humanity, you know what I mean? But yeah, but land and property like, you know, that it’s it’s better. It’s been around. I mean, maybe they changed the rules a little bit here and there. There could be a rule flip where it could ruin the entire U.S. economy if they just like.

Micah Johnson (17:37)

Right, great scheme of things. Yeah.

Christopher Angelo (17:54)

decided to take all the property. You know what I mean? Hopefully that doesn’t happen, but that’s possible.

Micah Johnson (18:01)

Durgan,

got an uproar on that one. I guarantee that. ⁓

Christopher Angelo (18:08)

But I’m like, I’m taking that risk because I feel like, I don’t know that that’s what makes most sense to me as an investor. So when someone I don’t say, hey, do what I do. Like if someone’s like, what should you should do this? Right. I’m like, well, you have to figure out what kind of investment suits your personality. You know, so that’s that’s kind of the thing.

Micah Johnson (18:32)

And it’s some of the best advice you could give them, honestly, because why you’re doing this business, what the whole point of it is, what the life you’re trying to create, all of that leans into the kind of investing that you should do. And it might be all three of those, right? You can stocks, crypto, and real estate if you want to, but it’s so unique to you. What appetite for risks do you have? What, in the words of Mark Manson, that book, Subtle Art of Not Giving, I don’t think I’m supposed to say the F word on this show, but the Subtle Art Not Giving,

No matter what you choose, you’re choosing its problems to not it’s good things. So be coherent of that. Be be aware of the fact that all the things you’re picking are going to come with the problems as well. And you can choose those. And that’s where it gets super personal. Is that the result? Me? It’s not as are these the problems you want to solve each day? Like for you, Airbnb’s the booking and the turning and all the different little things that have to happen routinely to make it go.

Those are all things you’re choosing. And it’s probably not the parts you like the most, but in the end, most of it is what you like. There’s always the sections we don’t like. For me, I try to keep it 80-20. If I enjoy 80 % of the process, then I will give up 20 % for the parts that just kind of, ⁓ not my favorite. But when it starts drifting further than that, hold on. This is not the life I’m trying to lead here. I’m not wanting to be stressed out all day. I’m not wanting to think about this particular thing all the time.

Christopher Angelo (19:40)

Thank you.

Gotcha.

Micah Johnson (20:00)

So how do I recreate, reset my life up to again, get back on that track? And when you’re planning that from the beginning, when you’re thinking about starting with the end in mind, now we can reverse engineer. That makes it where this becomes doable. If that’s the way you are, then here’s a possibility for you and here’s the step before that and here’s a step before that. There you go, let’s go. Now we can get some.

Christopher Angelo (20:14)

Thanks.

Micah Johnson (20:24)

Christopher, man, I appreciate your time today, your story, your perspective. I love speaking with folks that are, they’re doing it their way. And I couldn’t encourage folks to do that more. Get out there, meet people in the industry, connect with them, but don’t lose yourself in the process. There’s, I’m all for borrowing strategies and borrowing techniques, but the one thing that’s different in all of this is the person that’s doing it. No one can take your why, no one can take.

all the reasons behind what it is you’re doing, what you’re doing. So don’t trade them in. They’re important, very important, especially to you and your life. And something I think about is when all I have is a story to tell and I can’t do anything else, what do I want to say I did? That’s what matters to me. OK, when that’s it, when all I got are stories left to tell, because I’ve hopefully made it to being old and just sitting there with a bunch of grandkids hanging out. This is what grandpa did.

This is what I actually did. I don’t want to have to make anything up. I want it to be good stories at the end. So again, man, thanks for joining us today. If someone’s following along and you’ve been, they’ve been listening out there and they want to find out more about you possibly follow along with what you’re doing. What’s the best way to find you?

Christopher Angelo (21:29)

If you like to come.

I would say follow my Instagram. It’s Christopher, C-H-R-I-S-T-O-P-H-E-R dot Angelo A-N-G-E-L-O. ⁓

Micah Johnson (21:47)

Excellent, excellent. Thanks for sharing that. We’ll make sure that’s in the show notes for you out there watching and listening. Thanks for tuning in today. Again, Christopher, appreciate you being here. I think we need more people in the space doing it like you’re doing it. One of my favorite quotes, you’re not trading your truth for membership. You’re not losing yourself in the process. You’re building a real business that lines up with the life you want. And that creates happiness, man. That’s where it’s at in my opinion. So for those out there, thanks for joining us today.

Christopher Angelo (22:07)

for sure.

Micah Johnson (22:12)

If you got value out of today’s episode, please like this episode, share it with someone else you think you get value out of it. Please don’t forget to subscribe to our podcast. We appreciate everybody that joins us along the way. We’ve got more conversations coming up with operators, just like Christopher, who out there building a real business that supports the life they actually want to live. So thanks for joining us. We’ll see you on the next episode.