Commercial Real Estate Secrets

How ChatGPT Is Changing the Way We Do Real Estate Forever

• Aviva Sonenreich • Season 12 • Episode 114

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This week, I sit down with Topher Stephenson, Head of Operations at Aspire Commercial and author of Chat CRE News—the leading newsletter on AI and tech in commercial real estate. In this episode, Topher breaks down how ChatGPT is becoming a secret weapon for brokers, operators, and owners looking to save time and scale smarter.

What we cover:

  • How Topher uses ChatGPT to create bios, draft property descriptions, and even write drone video scripts
  • The difference between experimenting with AI and operationalizing it with custom GPTs
  • Why ChatGPT is ideal for CRE tasks like summarizing leases, analyzing zoning codes, and generating SEO-optimized content
  • What brokers need to know about integrating AI into their daily workflow
  • A behind-the-scenes look at how Aspire Commercial uses automation and ChatGPT to increase efficiency
  • Real talk: Can ChatGPT replace cold calls—or should it stay behind the scenes?


💡 If you're still wondering where to start with ChatGPT or how to move beyond basic prompts, this episode is your playbook.

Listen now to learn how ChatGPT is becoming a CRE pro’s most valuable tool.

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Aviva (00:00)
This week's Listener of the Week is Bama Mike. Mike, thank you so much for leaving us a five-star review. And for those of you listening, if you leave us a five-star review below, you might be next week's Listener of the Week. Week, week. This week on Commercial Real Estate Secrets, we have Topher Stephenson.

Topher is the head of operations at Aspire Commercial and the author of the chat CRE newsletter, the premier newsletter for AI in commercial real estate. Topher, thank you for being on the show today.

Topher (00:39)
Thank you so much for having me. I'm really happy to be here.

Aviva (00:42)
Yeah. So Topher for the listeners, who are you? What do you do? And how did we land here today on commercial real estate secrets?

Topher (00:51)
Great question. Great question. So my name is Topher Stevenson. I've been working in commercial real estate since about 2014 in kind of a variety of roles, you know, started out as a kind of commercial real estate marketing direction, then kind of morphed into, you know, commercial real estate marketing and in-house deal making. Eventually I was recruited to run management at a brokerage called the Boulos Company out of Maine and New Hampshire.

worked there about four years and eventually met a guy named Brandon Avedikian of Aspire Commercial on Twitter. And I guess it's called X now, but I still call it Twitter. We really, really hit it off. We were just kind of excited about all the same things, know, social media, AI and technology, and just decided that we had to kind of team up to move things forward and kind of make things happen. that's kind of the reader's digest version, but

it's, been a variety of roles can, you know, kind of what I do is kind of changed and shifted over the course of time. be it digital marketing or actually putting transactions together or running operations. A key piece of my role has always just been kind of staying ahead of the curve with technology and trying to solve everyday problems in commercial real estate using that technology. And so, you know, over the course of the past two years or so.

staying ahead of the curve became all about learning to leverage AI and just kind of figuring out how to put it to work in commercial real estate. obviously spend a great deal of time working on operations that aspire, but I spend also a good deal of time just kind of trying to stay ahead of the curve with all these different AI updates, trying to see which ones are actually relevant and applicable to commercial real estate and figuring out how to actually do something with them. So.

As you might've seen, I've put together a lot of content about that. I always try to be kind of tweeting different educational things and tips that people can use. I put a lot of that out through the chat CRE newsletter. I give presentations and teach classes on the topic, both digitally and throughout the country. And last two years have kind of been a whirlwind, but that kind of brings us up to now.

Aviva (03:12)
Well, it's crazy because I always say that in commercial real estate, like I feel like technology has maybe touched like one or 2 % of its capabilities in our business and we just have no idea what's coming and how it will impact our business. I think all, you know, it will be positive. It's like.

Of course we didn't see email coming, but like turns out it's a positive change in our, you most of the time. That's the time.

Topher (03:45)
To some extent.

I think some would argue emails become more of a curse than a gift, but yeah, absolutely.

Aviva (03:55)
But what is the most high value AI action you have seen in commercial real estate in your experience so far?

Topher (04:04)
Wow. That's a great question. I mean, I think it all kind of depends on who you are in commercial real estate, you know, kind of what is your role in commercial real estate? You know, like on the operation side, it's just kind of, all right, how do you, I guess we could start with more of like the marketing side, like the marketing side is kind of a layup, there's just hundreds of AI tools out here who could do, you know, that can help you execute some fantastic marketing, whether or not it's

brainstorming, know, writing the first draft of something so that you can make sure it's correct and add a human element, whether it's, you know, as I'm sure you've seen, taking a very long form YouTube video and then automatically chopping it up into a bunch of TikTok videos that automatically have the captions right in there. There's just so many ways to kind of apply it. so that that's kind of step one is just figuring out what tools are out there.

that you can actually use to save some time and figuring out how to apply them to what you do, be it commercial real estate or anything else. The next step is kind of customizing those tools to work for you. And that's where I think kind of the operational side comes in a little bit more. It's like, hey, if you can get ChatGPT to do something for you once, how can you customize it so that anytime you go to that particular instance of ChatGPT, it just knows what you want it to do?

Aviva (05:10)
Hmm.

Topher (05:26)
You know, maybe you have one that summarized leases for you, but you're tired of trying to remember the eight paragraph prompt to get it to summarize a lease. So you can customize one so that you just upload it. click the button and then you go. ⁓ and then the, think to me, the most impressive thing that I've seen people do is just start to kind of automate those things. It's like, Hey, you made a really cool custom GPT that knows you want a lease summary. How do you set it up so that you automatically get a lease?

and it just happens for you and you get sent the summary, know, that kind of thing. So it all kind of depends on what you want to do and you know, what are you wasting the majority of your time on? It's all impressive, you know, when it comes down to it, like it's, it's funny that we're already complaining like, man, I can't believe chat GPT can't do this yet. It's like complaining about wifi on a plane, you know, like it's amazing. Like the fact that it's doing these things are just incredible.

Aviva (06:06)
Hmph.

Topher (06:23)
You know, so it's hard for me to pick one thing, but I think when, once you figure out what, what can really save you time and you figure out how to automate it, that that's the most impressive thing that I'm seeing now.

Aviva (06:34)
I used to spend so much time digging in county assessor's websites, which county assessor websites are just for some reason, I find always terrible to navigate. And now if I want to find out

Topher (06:46)
Mm-hmm.

Aviva (06:51)
high level information about a property zoning. I will just put into chat GPT, tell me about, you know, Denver's UMX five zoning. And it'll shoot out a summary of that zoning. And then something really valuable is and it'll give me the link from the page as to exactly where they took this wording from. So now a 20 minute experience becomes a

Topher (07:02)
Mm-hmm.

Mm-hmm.

Right.

Aviva (07:20)
two minute experience where instead of spending the time searching for the information, you know, we have just saved so much time, instead of just clicking around. And now it's like, you can really dive in, you can be more efficient. I mean, in terms of, it's literally infinite the way that AI can help us in this business.

Topher (07:22)
Absolutely.

Mm-hmm.

Yeah

Yeah.

Aviva (07:51)
Do you find adoption for the average broker or owner? Are they hesitant? Are they excited? What do you see there?

Topher (08:03)
I see excitement, you know, which I think is kind of what excites me about AI and commercial real estate. Like people always kind of complain that, real estate, commercial real estate, so behind the times in technology. And part of that is not having the right tools that actually execute the right functions because it's a really niche business, know, yada, yada, yada. Part of it is lack of adoption and lack of excitement, but

With AI, it feels like everyone's excited. And just for the first time, that's part of what got me so interested in it. It feels like we have a chance. It just feels like we have a chance to not get left behind this time. So I see people excited about it. It's kind of hard for me to say, because usually the people I'm talking about it with are excited about it already. It's like, hey, you already have a ChatGPT account. You're already doing something cool.

I think the hardest part with adoption at this point is to some extent, some people have a lack of trust, but from what I've seen in CRE, that's a little less common. More people just kind of don't know where to start. like they just haven't really thought about yet, like, Hey, what are the capabilities that this can actually do consistently? And how can I use that to save time? So part of it is just thinking about what are those things,

What do you waste the majority of your time on? And it's like, all right, AI, most of them are chat bots. We all do a lot of writing, so is there anything where you spend a lot of time writing where maybe chat GPT could step in and give you the first draft, just kind of start it off for you so that you can clean it up afterwards. And after you...

see what it can do there. And after you realize that, I can upload a PDF and it can base its output and what it's going to write about based off that PDF, that just kind of starts really opening the doors and kind of illuminating in your mind, you know, kind of what it's capable of. I'd say that's the biggest thing is not lack of excitement. It's just kind of lack of people knowing where to start and what it actually can save them time.

Aviva (10:18)
It's so interesting. You know, some people have the argument that using chat GPT like takes the brain power out of your work. And, you know, my argument back at that is like, you're actually still thinking. You're just acting more efficiently in the way that you think and ultimately getting more high efficiency work done.

Topher (10:27)
Everything, yeah.

Mm-hmm.

Aviva (10:45)
something I love to do, you know, we need property descriptions, right? the more words the better because then we can achieve better SEO, yada, yada, yada. I love uploading a brochure into ChatGPT of the property and say, you know, whether I'm trying to list it, pitch it to a buyer,

Topher (10:45)
Yeah, absolutely.

Mm-hmm.

Exactly.

Mm-hmm.

Aviva (11:14)
give me a description of this property and why someone looking for a high credit tenant for, you know, X, why this deal works for them. And it, and then you upload, like you said, the PDF and in what, five, 10 seconds, I have, I have a coworker who is very,

Topher (11:26)
I love that.

Did the draft.

Aviva (11:40)
highly literate.

Topher (11:42)
Yeah. Yeah. And good at analyzing information. And so that, that's a really great example, right? You know, like when you're thinking about, okay, what's something that it can actually save me time on? Boom, writing property descriptions, you know, like what a layup. Everyone hates to do it. ..... hate to do it. They're sitting here going, all I have is an address. How am I going to write this property description?

Brokers hate to do it. think that's the administrative staff's job. So it's just something that always gets passed back and forth. So it's like, okay, AI can give you a really, really good start. And you provided a great example of, a property description. I'm going to upload some information that I have about it, and I'm going to ask it to spit out some sort of other information. Again, when you think about what is something that chat GPT can do for you.

to me it becomes, okay, how do I make a custom version of chat GPT so that every time I go to this custom version, it knows that this is exactly what I want to do. so you could have one for, Hey, you know, this is my custom version of chat GPT where I'm going to give you a property address, handful of bullet points, maybe a photo, cause it can analyze photos now, which is crazy.

And you're going to scan the internet, find as much information as you can, and then draft the description for me. And boom, puts that together for you. Then you could have another one, or you could probably tell the same one to do this. Okay, here's a brochure that I really, really like, or maybe it's my templated brochure. Now take that property description and just write the entire brochure. write the headline, write the bullet points, like the property description, put the contact information exactly how we normally style it. You know, put that in the bottom. Then you could.

have another one where you say, okay, you are my targeted tenant outreach bot. I'm going to upload this brochure that I just generated with this other custom GPT. Now I want you to draft customized emails or maybe a letter campaign, or it be a social media advertisement specifically targeting these four kinds of tenants. And it'll do that based off of examples that you've given to it. So again, it's.

It's just kind of thinking, okay, what, what is something that I could do to actually start saving time? Property descriptions is a great place to start. Then once you know what it can do, how do you kind of customize it so that you don't have to waste time trying to remember what exactly did I ask at that one time that I got the really, really good description. It just knows because you've already kind of told it that in the backend. And then once that's gone well, you can start to automate it.

Aviva (14:24)
I know brokers all want to have a robot that makes their cold calls and gets their listings. Is that coming? Is there a world where AI is genuinely doing our lead, lead gen or is that just, you need that human vibe?

Topher (14:32)
Mm-hmm.

I, we could do a whole podcast episode about this. So, A, you can do it. You know, there's tools and platforms out there. I think one is called Bland AI where you can set up these outbound call bots and give them a list and they'll start making those calls. A, you know, people barely want to get cold calls from brokers. They don't really want to get cold calls from a robot. You know, I'm being, I'm being a little facetious. I'm sure some people are out there

Aviva (14:48)
Hahaha

Topher (15:13)
who are making it work and doing some business with it. on the one hand, would that save a lot of time? Sure. On the other hand, on a long enough timeline that that's going to be one of the key things that are left that brokers are really, really good at that they'll be able to do way better than an AI. So, is there a place for AI?

calling machines in commercial real estate? I think there's probably a place for it. Does anybody wanna start receiving those calls? Like, do you wanna get them? No, probably not. You know, so that's a piece of it. is it doable? Yes. Just kind of feels a little gross. But, you know, is there a place for...

Aviva (15:54)
Yeah, yeah.

Topher (15:57)
using AI to really, really enable you to step up your prospecting game. Yeah. I think there's absolutely a place for that. I don't, I don't know if you've ever stumbled across a tool called terracotta, but I was able to, to interview or do a demo with, one of their co-founders, ⁓ Vincent the other day. And what an astounding platform, it's I, the people that had told me about it just told me that, Hey, it's a really, really good power dialer. You upload your list.

And it'll call people for you. And then if you connect to one, takes over your screen and all of a sudden you have the property info in front of you. You can talk about it, or you can use AI to leave them an AI generated voicemail, which already sounds pretty good. But then I met with them and he's like, oh yeah, they didn't even mention the best part. They've somehow figured out a way to automate this tedious process of I'm going to go to the assessor's website and I'm going to download a list of all the people that own all these office buildings.

And then, I'm going to try to look up the LLC that owns the office building and figure out who's associated with it. And then I'm going to go over to maybe zoom info or maybe I'll go to LinkedIn, or maybe I'll go to white pages or true people search and try to find that information. That's the worst, no one likes to do that. I've never really seen a technology platform that was really, really good at doing that for you. And they've somehow figured out a way to do that with AI. so,

Is there a world where you can just give AI a perfect list and it can do the calls for you? Yeah, it's probably out there. I don't love the idea, but most people don't even have that perfect list. But this platform, it can go build you that list. And there's going to be a bunch of numbers that are wrong, but you know, that's kind of okay. Cause the power dialer is just going to careen through that list, and then eventually you're going to get on the phone with someone who actually owns a property. So.

Aviva (17:31)
Hmm.

Topher (17:45)
I think there's a lot of elegant solutions that are starting to come online to help people leverage AI with business development. I'm almost hoping it doesn't take over that whole section of commercial real estate because I don't want to get those calls.

Aviva (18:01)
It's so funny, we own a portfolio of warehouses and I have the contact information in CoStar where a lot of brokers export lists and pound the pavement. I get the inbound because I like to hear what they have to say, what properties they're pursuing. I just find it fascinating.

Topher (18:06)
Mm-hmm.

Mm-hmm.

Sure.

Aviva (18:23)
I get the brokers who, who think that AI is just, ⁓ robots are to be making my calls. where do I sign up? Which is like, that's not really how that works. and the life that a broker brings to make a deal happen.

Topher (18:34)
Mm-hmm.

Aviva (18:45)
I don't think can be recreated through AI. But it's like you said, it's figuring out our efficiencies and maximizing them by creating GPTs and custom GPTs is the future of our business and whomever can figure out how to leverage the technology to optimize their time wins, which is fun.

Topher (18:45)
Mm-hmm.

I- yeah.

They're going to win.

Yeah. And, you know, I think it's, it's interesting. Hopefully I didn't get too down on an idea that you were really, really excited about. I think there's definitely ways that AI can help with, with, ⁓ business prospecting, you know, again, a lot of it comes back to your data. it's kind of interesting looking at an industry like commercial real estate versus, like a

Aviva (19:22)
No, no.

Topher (19:39)
a sales development team at a tech company. they feel very strongly that their data all needs to be correct in their CRM because they want to eliminate friction between making calls and actually getting in touch with these people. Most people in commercial real estate don't...

necessarily spend a lot of time on that, but are there ways to use AI to double check your database, make sure that these emails that you're sending thousands of emails out to are actually correct. And then if they're not correct enriching the data, yeah, there's starting to be tools available for that. I think AI is definitely going to help enable some people in commercial real estate.

be much more effective with their business development and actually putting deals together. But again, it all just kind of comes back to your business. Some companies don't even have a super robust database yet with a lot of wrong information. So it's like, that's probably not going to help them. But if you don't have any place to start, and you just want to start making some calls on properties, okay, Terracotta is probably a pretty cool solution for you because it's actually going to go start finding you those numbers. And then once those numbers...

Aviva (20:49)
Yeah.

Topher (20:50)
you actually kind of connect with somebody, all of a sudden you do have a correct phone number that you can put into your CRM. And eventually maybe a year later, you want to go back and use one of these AI tools to kind of, you know, do a sweep and make sure all the information's correct so that when you go to call them again with your power dialer, you know, you actually get in contact with that person.

Aviva (21:10)
So how are you using it at Aspire? Like talk to me about practical application of AI at Aspire.

Topher (21:21)
Absolutely. And so again, it all kind of comes back to like, what is actually going to help your business the most, you know? And that means a lot of things to a lot of different people and a lot of different companies. For us, we're a relatively small company and in some ways we're still a startup. You know, it's a very young company. It's less than two years old. And so when I first came on board with the company, coming right up on six months ago,

Aviva (21:29)
Hmm.

Yeah.

Topher (21:50)
You know, I was all amped up on AI, Brandon's all amped up on AI, we're going to do everything with AI. But you you very quickly realize like, okay, you got to pick your battles and figure out what's actually important to you. So we, we actually started by saying, okay, we're going to pump the brakes on AI for a second because we're a young company. We're working with a lot of overseas talent to do a lot of our operational tasks. A lot of them are very fresh to doing all of these tasks, or at least they were six months ago.

We don't have a lot of these processes written down for how is any of this actually supposed to happen? So we said, okay, first we're going to start with project management automation. know, so it was, I kind of lump AI and automation into similar buckets just cause it's, it all comes down to how are you leveraging technology? within a couple of months we said, okay, what, are the things that we're doing every single day? we're making brochures, we're making floor plans, we're sending invoices. Let's.

process and operationalize all those things. So it's when someone needs a new floor plan, they fill out a form in our project management software that automatically flows and notifies the person who has to create it. they say that, Hey, this is ready for review. It automatically notifies the broker over here that it's time to get reviewed. It is reviewed and it's ready to go and it's time to go on CoStar. So it notifies our guy who manages all of our listings for us. And, you know, so all that is to say, we decided, Hey, let's get started with.

automation not necessarily trying to do things with AI. But then from there, kind of quickly flowed into, again, all right, there's a bunch of things that we know AI could help with in our business, but how do we make it simple so that, again, when we go to use it, we're just not kind of recreating the wheel from scratch. So it came down to building out custom GPTs. And so I had a bunch of ideas. Brandon had a bunch of ideas.

Some of these are GPTs that we like barely use ever, but when we go to use them, it's like, that's so fantastic. You know, we have a new bio generator GPT for, Hey, we just, hired a 20 year broker. got to write a pretty good bio for her. I should say a really good bio for her. so, you know, she fills out a form. Here's a bunch of information. We pop that into the GPT. It has access to a bunch of other, you know, employee bios that we've created in the past.

Aviva (23:42)
Hmph.

Topher (24:05)
It just drafts a draft it for us. we fact check it. We make sure she gets eyes on it. She actually likes it. And boom, that thing that probably would have taken an hour or two hours of either previously Brandon's time or now my time, just took a couple of minutes. So, you know, we have those GPTs for social media posts. WE We have GPTs for again, something we're not using every single day, but Hey, we do a lot of, drone video marketing for our properties. So it's

drone guy is going to go out and get the drone videos, but we want to do a voiceover. Somebody's got to write that. it's kind of a painstaking process. So, Hey, here's our custom GPT where we can upload the brochure has all the information about the property. Now it just writes that voiceover for us. So again, I'm, kind of going in this order because again, I kind of go back to marketing is a good place to start just because there's so many ways you can use it to not just

Aviva (24:43)
Wow.

Topher (24:57)
stop working, but to do more, to add more value to make things easier than they were in the past. you know, we've gotten into more nitty gritty stuff as well. we have a gentleman in overseas who he reviews our leases and he creates our invoices for us, but he's was still fairly new to this process when I got to the company. And so all of these invoices need to be reviewed somehow. So we created.

created a custom GPT, you dump in some information from the lease, it'll ask you, hey, what's your commission percentage? Hey, what are your billable terms? Dumps out all the information that needs to be in this invoice. And then we automated it. So again, we kind of started by building out the project management system. Now these leases are automatically going into our project management database. And I essentially built a automation that says, hey, there's a new lease.

Aviva (25:29)
Wow.

crazy.

Topher (25:50)
we're going to run it through all of these steps through the cloud API, pull out all of this information and basically draft the same information for the invoice that we would have through cloud And I'm just going to get an email with that information so that I can double check it against to know what, our operations staff puts together. So all that is to say very boring ways, we're not using necessarily using AI for things that are

Aviva (26:14)
Yeah.

Topher (26:17)
Super exciting, but really the focus of a lot of what we're doing right now is, Hey, how do we become more efficient? Hey, how do we leverage AI to do things either that, no one necessarily has the time to do from scratch or doesn't have the time to dedicate enough to do it particularly well. And how do we kind of free up our time so that we can do the things that are really exciting, you know?

Aviva (26:37)
Hmm.

Topher (26:42)
That's just kind of a handful of ways, I could rattle off a bunch more, but, again, it all comes down to figuring out something that you can do customizing AI so it can kind of do it for you with very little instruction and then figuring out a way to automate it.

Aviva (26:55)
Do you do your automation with Zapier or?

Topher (26:59)
You can use Zapier and it's funny, I liked Zapier for a really long time. A gentleman reached out to me on X, the CEO of a company called Relay. And they're kind of like Zapier, they're kind of like Make, but they're just kind of a little more AI forward. So it's all kind of built towards, you know, leveraging AI in these, in these different steps. Whereas Zapier was kind of, it was already an automation platform. Now they're kind of tying in AI.

what's good about something like Zapier or make they've just been around longer. So they have more things that you can integrate, but I've been able to do some pretty cool things with a relay and by pretty cool, mean, extremely boring, but they save a lot of time.

Aviva (27:30)
Wow.

That's cool to me.

Topher (27:45)
Yeah.

Aviva (27:47)
What makes you happy with what you do every day in commercial real estate?

Topher (27:54)
makes me happy with what I do. Um, Hey, I just kind of fell in love with commercial real estate. just being involved in, I don't know something about it. It's just such a niche industry, all every role that I've been in, in commercial real estate, I've kind of loved for different reasons, but, as far as the operations side of things, I do kind of like looking at something that is kind of complex and trying to figure out how to make it simple. And so.

Aviva (28:01)
Let's go on.

Topher (28:21)
I love doing that within the world of commercial real estate. So I really enjoy that. And then on the AI side, I was talking with someone one day and again, the example of, Hey, you know, I uploaded a PDF to chat GPT and that just kind of unlocked in my mind, like all these things that you could get it to do. That's kind of, I think what I love about working on the AI side and kind of educating people about it.

is again, you might want to edit some of this out. I probably sound like a broken record, but it's what you can get out of it is so kind of nuanced based on who you are, what your company does and what you do and what you're focusing on right now. And being able to help people kind of find that one thing that just illuminates them and they think like, ⁓ my goodness, this could change everything. I really, really get a kick out of that. So that's kind of something I love about.

Aviva (29:02)
Yeah.

Hmph.

Topher (29:19)
on the AI side and just kind of educating people on it.

Aviva (29:23)
It's a cool industry,

commercial real estate. I think if you're young and curious like you are, opportunity is immense. And I suppose that's why we're here. So, Topher for the people, where can they find you, follow you, sign up for the newsletter, et cetera.

Topher (29:43)
Appreciate it. You can find me on X or Twitter, if you're old school like me, @ TopherNow. So T-O-P-H-E-R-N-O-W. And you can find my newsletter at Chatcrenews.com.

And I put out a lot of different content on LinkedIn and Twitter. But if you want just a once a month dose on updates on different AI tools and ways that you can actually apply them to commercial real estate, if you only want to see it once a month, definitely sign up for the newsletter. If you want to see it every couple of days, come find me on Twitter. And then once in a while, I post something on LinkedIn too.

Aviva (30:26)
Topher, thank you so much for being on the show. For all the listeners, chat, C-R-E news.com. And for everybody listening, we'll see you next week.


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