Luxury Commercial Real Estate in 2026: Aspen, Miami, Caribbean Deals

0:03 In this episode, we're talking to Kayla Mahoney, A broker at Ingle and Boker about untapped markets, how to spot unconventional opportunities, how to work with non traditional clients, and why boutique brokerage firms often have a structural advantage in 2026. So I'm really excited to have you on the show to talk. I want to get into it. Kayla, where are you seeing opportunity where others are not paying attention in 2026? As we see right now, there's a lot of larger companies that are getting into the Wellness space and there is a resurgence for people leaving Airbnb and going back to the more traditional hotels.

0:47 Because of this, in my existing relationships within the hospitality sector, my real estate practice really focuses in on that luxury regards. There's two ways in which I utilize untapped markets. First one is going to unconventional markets where there's a strong residential presence, a lack of commercial presence and a significant amount of growth. So the majority of my outreach for Q1 in 2026 is actually really honed in on looking at Caribbean hotels. I know that there's a lot of flags and a lot of concepts that really want to have their mark in the luxurious Caribbean islands. They're looking for these all inclusive resorts. There are also a significant amount of all inclusive resorts that are a little dated and with the right property improvement plan can really be activated. The reason why I love the Caribbean as a sub market to really immerse myself into is just because unfortunately the lack of resources and education in those markets. So I can come in and provide value with my ability to underwrite and analyze deals from what I've learned in CCIM. And then also, so that's like where I like to tap who I like to connect with more than anybody are residential Realtors, specifically high performing residential Realtors that are doing really well in their business. But the costs for them to go and acquire Costar Krexi and learn the local economics of each five sectors in real estate investing, it's just more worth than work than worth for them. So that's where I come in and I

2:22 actually reach out to a lot of residential Realtors to build referral partners. And I know that when I was working in Denver, which I still do have my practice in Denver, the amount of times I would talk to a residential realtor who would end up getting turned away from a commercial broker because of their lack of knowledge in the industry. And a lot of the times, especially these people who are taking care of clients with their multimillion dollar homes, 90% of multimillionaires make their money through real estate investing. So, you know, the lion's share of their buyers have a commercial real estate portfolio too. And by incentivizing them through a strong referral program, they're able to take over their entire portfolio. And from what I've learned from this is when you talk to those owners directly, there is so much more trust built in because they've already been helped and they had their agent perform on the most intimate investment that they will purchase in their current life, which is their house. So really just being a tool for residential agents and providing a strong referral incentive was actually how I got into the game and was really able to leverage my brokerage career without going more linear with how I transact. Wow.

3:31 You know, I also have a passion for Caribbean hospitality, but more on the consumer end. I got to work on my dad jokes. That was that was I'm sorry. Oh no. Man, I bet it. I mean, but wouldn't you rather be doing a showing at a high end hotel or wouldn't you much rather be doing a showing on a beach versus, you know, I'd walk into these MTV vet, but I would walk into these C Class warehouses in my tall ass heels. Like I had 4 inch heels when I started in commercial real estate in Denver, walking through like the industrial sludge and I was like, why am I not doing the same thing? Even nicer buildings.

4:12 Hey, and and that's a reason why I transported up to Aspen was because once you get to a level when it comes to luxury and income, people actually are afraid to approach these people. And I'm sure it's under farmed. And that's what we're talking about today is untapped markets, right? Where can you catch an edge for your time? Because the risk in 2026 isn't being wrong. It's being crowded. Kayla, how did you start working with unconventional clients? I suppose you answered that with your residential clients. Yes, that's just one facet of it. But the residential Realtors don't necessarily always have that clientele, but the ones that do, those are the ones I really, you know, flourish with helping. But how I really got into it was actually just from my own network previously.

5:08 I have some pretty deep connections within the hospitality space in Miami. And that really just kind of catapulted my career. And I remember when I was sitting in, you know, my previous firm trying to hit up downtown Denver retail, I realized I had no pieces to connect. And that's not a bad thing. There are plenty of brokers who are very well connected in the retail space, but when I'm spending my nights and weekends like and where I'm going and what I'm doing, I realized that I was in a different echelon and being in that world was really how I was able to activate those relationships.

5:51 Before real estate, I worked in the music industry as a graphic designer for a music magazine. From that, a lot of my friends have are now pretty high profile musicians that tour internationally. And there's always people that have this lure of access from connecting to creatives. And as a fellow creative who went into a more, I want to say conventional career path, I still have those life lasting friendships too, where I'm able to, you know, shine and provide some sort of value even before knowing them by getting on backstage at one of their favorite concerts. And then it's like, OK, that relationships built. We're able to hang out, we're able to build that trust and and eventually they just kind of come around.

6:37 Networking and strategic networking. Yes. It's going to be big. I know it just. Yeah. So you're obviously not. This is not a theory. This is navigation in progress. How do you? Spot. Markets that maybe others would have initially ignored. Just pay attention to what's happening in the world, really, and paying attention to where money is moving nowadays with how big we are and how we do have access to the entire world and our computer, you could really tap into local markets more than you ever were able to in the past. And I kind of just backtracked it if it's like, OK, where do I like to travel?

7:27 Who do I like to spend my time with? And most importantly, where am I seeing cranes without a CBRE? Where am I seeing cranes with no JLL signs surrounding me? Again, not that those bro bridges are bad, but because they have the institutional power, they already have the outreach in that market. And so when I'm on my travels now, I'll look to see what is emerging in that area. I think that's smart. And you know, I'm, I'm reminiscing. I was in the Caribbean last week and you're right, I didn't see a big Top Shop sign anywhere. It's so smart to like have those lenses even when you may not be working because that's where opportunity can be found.

8:15 Exactly. And when you are working, you should always be surrounded by people you know, like and trust and who are ultimately your friends. And so where you spend your time with your leisure should also be really where you focus your efforts in marketing and outreach because it makes the job less mundane. Also, what you would see a lot of the times in different markets, specifically within the Caribbean, because there's that lure for a vacation home. You will see luxury residential firms, but you will not see the commercial firms because there's not enough of a market share for them to put a driving force behind it. But in the residential realm, there is enough of a market share and there are a so many smart agents like internationally who are able to help you. And for them by being able to work on a development or a hotel or a retail center, not only is it helping their smaller communities, but they're also able to put themselves as the forefront as a preferred advisor there in commercial. And you can come in and collaborate with them as a referral partner to mostly mentor and also help get their deals to the closing line.

9:26 Huge. That's fine. That sounds like a win win for me. Yeah. And you know, I it's just, it's really interesting seeing with 2026, like we're starting to see more optimism. We're starting to see people understanding the rates and the economics and, and deals actually making sense. But the cost of construction is still astronomical. We do have major labor problems and granted those are all in every market as well, but for some communities that are looking to be incentivized with development and are looking to activate their tourism economy, you can come in and just help them.

10:10 That's interesting. So you know in 2026, I feel like people are starting to finally put out commercial real estate content online and experiment with new marketing techniques for brokerage. I wanted to see high level what you are finding to be your best and most creative marketing tactic in 2026 other brokers are not using today. Yeah. So for me, when I first got into commercial real estate, I didn't necessarily understand the industry of commercial real estate, but I understood social media for my previous work at music magazine.

10:52 So I initially started, I made an Instagram right away. I had Facebook, I was doing a little bit of TikTok, nowhere near to the amount of TikTok that you had. But then my accounts got hacked and it was kind of a mess. That said though, when I looked back at my social media, I was really only pulling tenant Rep deals and I think it was because of a mix of my content as well as my experience. So after that, about a year and a half ago when AI really started to make its way into the forefront, I ended up getting really into go high level and building out automated emails and automated text files. For me right now, the texting is actually worked the best because there aren't many brokers utilizing it and you are going in as another form of a cold call that's a direct contact. Like yes, I always believe call first or have a dialer call for you first just to make sure they hear a voice. They know you're not a robot because we do get text advertisements but not many Realtors just use automated text messages.

11:58 And I have a different funnel for each of my listings for outreach and I've been able for every listing to convert to buyers on average and it's really helped my business through. It's so ridiculously opportunistic and it's so crazy how the institutional brokerages don't want to foster the opportunity. And this is where as brokers and investors and any type of professional, in my opinion, we can lean in. And I think that them utilizing modern marketing tools is a really strong opportunity for brokerages that do to grow.

12:38 You know, one group that I see that super successful is science or Hearts. Granted, he's on Netflix, he has that publicity, but he's growing and he was very bullish on technology. And I think that that's a reason why he is in the position that he's in today, which is one of the top. Yeah, absolutely. Yeah. So why are non traditional clients frequently overlooked by these larger brokerage platforms? I think it's mostly just because of the inability for those brokerages to execute on a portfolio wide basis without implementing in referral partners because at the end of the day, brokers are extremely oversaturated industry. You can find a broker anywhere.

13:26 I mean, it took me like 3 weeks to get my real estate license. Like literally you could just do it in 150 hours, take a test and you're a realtor. And with the rise of reality TV and real estate, everybody sees the glamour that comes from that. And they're like, Oh my goodness, I can do this too. So you get a monstrous amount of agents that come in and they're looking for mentorship, partnership. So they end up going to a firm like CBRE, Marcus and Nollechhap JLL even in NAI and they're told, OK, you are going to be an expert in this market, you are going to be a master in this territory.

14:11 Anything else that is with outside of the parameters of this market in this territory, you're going to have to refer out to the brokerage that's in that respective section and you know, and that works on being truly the local expert. But I don't know a single portfolio owner that does not own assets if it's in multiple markets. I also don't know a single portfolio owner that only owns within. I'm just going to use Denver since we both lived in Denver. You know, I don't know a single portfolio owner that only owns multifamily or only owns office within one zip code of Denver proper. And and that's really what you're going to do is just be the best know everybody. So now you have 5 different agencies that operate on that caliber.

15:00 So there's probably 10 to 20 different players that these people are all talking to that are the same. And then when they say, OK, I have a multi family property in Aurora I need to offload, but I want to bring my capital down to North Carolina because I know that there's going to be a residential need due to the Toyota plants. And I know that Denver has a compressed cap rate. You end up having to go and refer that business out and you're referring it out ultimately to somebody you don't know because those firms are so large that that client might love you as an agent, but not love the person that they're referred to. And today with AI, the access that we have to data and the access that we have to information, putting listings live, etcetera.

15:47 Like, you really are working with a person because you know them, you like them, you trust them, and you're working with them for The Who they are, not what they know, even though what they know is essential. But if you're truly working in the brokerage industry, you can find 50 people that know just as much as IG or just as much as Aviva does. And granted, there's going to be some nuances because of what we focus in, but any agent who's a good agent is going to take the five extra minutes to go do that research for fourth meeting to seal the deal. The best clients are often the ones nobody else takes seriously early on.

16:28 Exactly. And the off market deal I'm working on with Aviva attacks that on the head and it's exactly what you're doing too. It's a luxury property in a luxury market. Nobody really cold calls in that market because they're afraid of the competition. They're afraid of this one family that's a developing family that's just going to crime and monopolize it. So they say why bother? But not every person within that some market likes that one family. So why don't you go in and beat their competition? I can't wait until in another five years when we do, well, hopefully we do another podcast before then.

17:10 But it'll be funny to just like look back at these and laugh and see how we grow. And it's it's fun. It is fun. I even look at racket what I was doing in 2021 on my Instagram and I still have some of them saved and it's like, hi, my name is Caleb Mahoney. Here are the five sectors of commercial real estate. And oh, fun fact, I love death metal. It's like it's like and they're like my all pink and it's not true. I love death metal and I was just learning the five sectors of CRE and I didn't know what else to talk about. With a failure rate of 90%, you're still standing so. Standing.

17:56 I'm still standing. And I actually got more engagement on those responses because it wasn't directly about my business, but it was about me as a person. And people work with you because of who you are. When they have technology that could blast their listings, do all the exposure. I mean, if they have basic, if the owners have basic negotiation skills, they can sell it on their own and save upward of six points if they're paying agents properly like they should. But they they don't want to deal with the headache and they really appreciate your service. They really appreciate your knowledge and they appreciate the fact that you make them feel special. Among things, but yes.

18:41 So aside from the fact that dealing with an institutional brokerage is like dealing with the mafia, why do you feel boutique brokerages are the future? I feel for me at least, a boutique brokerage is the future with my business because of the flexibility. My background is. How I learned everything in real estate today is through exchanging and with the exchangers I again another untapped resource. I would sit there every Wednesday for like 3 years with a bunch of gentlemen with the median age being 75 and these guys are talking about how they flipped a Persian rug and converted it into ground for a mobile Home Park.

19:26 And then to get funding, they ended up using their car that was owned free and clear as collateral and threw in a couple like gems that they had sitting around like raw rubies. And, and you know, I, I think that institutional brokerages do not have the flexibility to transact like that. And in today's world, in today's economics, when conventional financing or alternative financing does not work, you have to be able to get creative. And when you are told to be rigid and to be in your place, it essentially stifles your growth. You know, I know a lot of these large brokerages, they have their brokers come in, their brokers crush it. They do the best that they can do. They're an expert in their territory. They're an expert with the ownership. They do a fantastic job.

20:14 They know the market inside and out. And because of the amount of brokerage that they've done, they know how to invest when they go to like their brokerage head and they say, hey, like, I actually found this sweet deal. I'd like to go in as a partner. I will pay your Commission. I'll pay your brokerage fee upfront. I would like to use my Commission for a down payment and syndicate this asset. You're told, no, you cannot do that. And for me at least, the goal of being a broker is to become an owner, because by becoming an owner, you're able to build legacy wealth that lasts for generations. And if I'm told by my boss that I can do that for other people, but I cannot do that for myself with my relationships that I've built, done.

21:07 And I think more people are starting to realize that too. You don't have to force a transaction in a boutique brokerage. You have the freedom to choose the right ones. Absolutely and. Yeah. I was going to say, and it's really interesting right now seeing the acquisition with Compass because I believe that Compass is primarily a technology company. And I, I do see them trying to figure out a way to utilize technology to eliminate the role of an agent in order to collect more for their funds and then converting their agents into co-ops or giving them stock share something like that. You know, I can I can totally see that happening to try to demise the agent and you know, by by not providing flexibility with your clients as well as a personal relationship. You know, it could be a friendship, it could be a mentorship.

22:01 It could just be like, like me, I end up getting a lot of clients because they will see like a lot of drive that remind them of their daughters or see a lot of drive or, you know, have that relation because their kids are my age and they like to see that I hustle, which is I guess not something common in today's world. Young people are hustling. They just sit behind their computers and type away. So, you know, you don't really want to have a company that's going to stifle your own growth and your own freedom. No, that does not sound like a party I want to attend there. Are still a lot of people who make great money brokering in that trend, in that fashion, and I think that's fantastic.

22:43 But no, I don't want to go in as a junior broker, do 500 cold calls a week knowing that cold calling is dead, get maybe 3 responses. And no, after pounding the phones for a year and a half, I have a book of clientele that I could have made from using social media. My automated text messages in 10% of the time. Music to my ears and something I've been screaming from the mountain tops and enjoying the fruits of that labor for the last five years, so I'm right there with you. Yes. And you know, I was building my career at a time when TikTok was coming out. That's when I got into brokerage in 2021. So in my generation, we don't call.

23:26 Like, yes, you always hear the guys say just pick up the phone and call at all these conferences, just pick up the phone and dial them. And it's like I ignore when I don't know the caller ID because I get a bombardment of calls. It's overwhelming. I don't know why you're contacting me. If you leave a voicemail, I actually read the voicemail and I text back and I know that there's a generation that prefers the calls, but there's a generation that's coming in that refers the text messages. And I think that behavior, it's so important to understand the average person is not average. If you're doing that behavior, it's highly likely other people your age are doing that behavior. And Kayla, you couldn't convince me that our parents are not doing that because I, I think they are. I know people, I agree cold calling is dead. I agree that people have control now of who they answer the phone to, and they don't want to hear from brokers. We are in a new realm, a new reality, and it favors the bold, it favors the creative.

24:34 And if you're selling something as big as a hotel in the Caribbean, you better get creative with your marketing because the average marketing is not going to work. The average marketing is not going to work, but then also you need to come up with creative solutions as well because your buyer pool is really small that you could present it as a joint venture, you could present it as a Co-op. You could get in five fires. You can, I mean you can make the deal crypto if you really want to go crazy, creating your own coin as the currency and utilizing the appraised value of the asset as the, you know, backstop for it.

25:14 And so if you don't have those tools in your belt in order to transact, it makes it really difficult with inflation in order to have conventional financing pencil. You know, we see deals that are going between a six and seven cap and you see rates going for a six and seven cap. Cap rates do not include mortgages. So if you go in with an LTV, you know, 2030% down and you're paying your note with perfect credit at, you know, a 6.5%, but that asset in itself had a 6.5% of its return. That's a unless if you have a significant value add, that's a bad investment and most people do not realize that.

26:00 And you're like, wow, OK, A6 cap looks glamorous. Like what do I do with this? Like is there are there rents in here that I can bump up? Is there, you know, am I going to convert it into an owner user plan, implement a lease back? Like it's just it's just not feasible and I can go on for this forever. It's just not feasible. It's. Not a bad day. Yeah, you know, and it's, it's you're going to have a bad day trying to figure it out, but then shoot, you're also going to be upside down and potentially facing foreclosure. And, you know, sellers are still on another planet right now.

26:41 But of course they're going to be because it's like if I don't have a need to sell, why would I sell if it's not going to make the number I want when the market softening? So looking ahead, you want to get ahead in commercial real estate in 2026, where should we be focusing? We should be focusing in on being an educational resource utilizing technology and not have everything the full education. Make it super fun, make it super short, make it zesty. Don't be afraid to put a Rick and Morty post on your LinkedIn. Like I had a deal that closed in December strictly from LinkedIn. I had a client with a 10/31 need. There was nothing in their market. I found.

27:32 I put a Rick and Morty like show me what you got like late. You know what they do that and it's like, show me what you got. Not only was that, like, one of my top five highest engaging posts of that year, but within 60 days, I managed to close a $6.8 million deal off a LinkedIn reply and IT educational technology. But it wasn't the, you know, boring broker. Like, yeah, you see it all the time when you scroll through your social media where it's like the company's logo, the building. No, like, people engage more with pictures of you so you can post. Don't be afraid to post that personal selfie on a professional platform.

28:13 It just matters. What you write is the caption. I'm right there with you, yeah. And show, show yourself because at the end of the day, technology is going to take over, but those of who are really going to shine in this industry are those who are not afraid to be authentic. The next wave of success in real estate will not come from playing the same game better. It's going to come from playing a different game earlier. Exactly, and it's really interesting too, because for CRE data like costar, Loot Net, they're like the master gatekeepers of the data where you pay like $120.00 a listing to advertise it on Loot Net for the basic and $520 a month on Costar.

29:05 The reason why we provide value to these owners are because they don't want to spend that $800 a month just to have an understanding of the market. So for us agents to pay that money, understand what's happening within our local economics, and then just relay that information back to our respective clients and even higher on a social media public basis. You're going to get so much more to come in to you. At least I'd add so much more come in to me versus date keeping. 100% so if someone listening wants to explore untapped markets or techniques, what is step #1? Step number one is to analyze.

29:48 You figure out where you want to go, what you want to do. Because each of us, we are all individual when it comes down to it. And I know that there's going to be some things that I'm interested in that I know Aviva is not going to be interested in or my fellow Co worker. And then tap into where I go to enjoy those things. It can be an activity, it can be a, you know, I love shopping, OK, retail. But from there, then look into the local economics, but specifically the microeconomics and pay attention to the median incomes within those demographics. And really just try to find that sub pocket to activate. Like I love looking at like Aspen. I love looking at Napa.

30:34 I love looking at these treachery markets in regards to population that have a median income that surpass the city's median income. So like Arpin, Napa, like I definitely am very into some submarkets in the Carolinas right now. And it's it's just because they're making more money, so they have an appetite to invest. But brokerages are mostly focused in on larger cities because there's more activity. When I found Aspen commercialrealestate.com was available for sale in 2025 for $12.00 on GoDaddy, I about fell out of my chair. Then I got back in my chair and bought it immediately because I couldn't leave. That wasn't domain that was available. Yeah.

31:22 And it's, it's funny because it's like, wow, it's such a generic domain. It's also something that will crush it on SEO searches, like because people find what they need from a Google search now they're not finding what they need from somebody calling them. So it's like Google search it. Aspen Commercial Real Estate, you see Aviva, you know everybody's going to go to you as they should because you're fantastic. And then I went on to Instagram, Aspen commercial real estate available. I'm like, what is this? What is going on? And and that's the reality of commercial real estate and dealing with these markets. It's actually crazy how opportunistic it is. And I'm excited to play ball with you and by your side for the next, you know, at least a few decades. So wrap it up, Kayla.

32:10 In every market cycle, there are crowded paths and quiet paths. The crowded path feels safer, but the quiet ones often are where the opportunity lives. The brokers and investors Who Will Win in 2026 are the ones willing to look differently, serve differently, and build where others are not paying attention. I really appreciate your time today. Thank you so much for being on the show. Any last thoughts before we sign off? Thank you so much for having me. I'm going to insert my shameless plug here. You can reach out to me on LinkedIn. Kayla Mahoney. I work as a commercial real estate advisor primarily in luxury submarkets.

32:56 I'm transitioning from Denver to Miami right now to become a hospitality broker and really push that market further. Also, if you guys have any alternative financing that banks do not touch, I have access to ample amount of capital to deploy for bridge financing, construction financing, equipment leasing, you name it. My colleague has close to a billion dollars he needs to lend out this year, so I'm helping him sell. That's very nice of you to do that. I ask more. People. Just my arm. Yeah, if you need money, a girl, if you need money, if you need money and if you need a class real estate in the luxury market, hit me up. Kayla, you're awesome.

33:38 Appreciate you too. And for everybody listening, we'll see you next week.