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The Real Estate Addicts (REA) podcast is a must-listen for anyone interested in real estate development, investment, construction and entrepreneurship. Each episode dives into a wide range of industry topics and features conversations with savvy, successful entrepreneurs who candidly share their career paths, challenges, breakthroughs, and the stories behind the remarkable companies they’ve built. Expect big personalities, thoughtful insights, and conversations that both educate and inspire.
Co-hosted by Ray Hurteau, Dan Rubin (Instagram: @rhinvestgroup), and Marc Savatsky (Instagram: @choose_boston)
Follow the Real Estate Addicts Podcast on YouTube: @RealEstateAddicts
00:08
You're so literal sometimes. All the time. Welcome to... Gosh. All the way, All the way, This is what I deal with, Guys, are the microphones recording? Are we live? We're here. Welcome, everybody. Let's do it. Welcome, welcome. Welcome to the Real Estate Addicts Podcast. We're here with your host, Marc Savatsky Choose Boston. Dan Rubin RH Investment Group. Ray Hurteau, same company. And joining us today is our guest, Caleb Wursten, here with Goodstander. Excellent. Is that microphone okay?
00:37
I think so. Yeah, you're getting there. angle it up a tiny bit. Perfect. Well, welcome to the podcast. Welcome to the union. Caleb is our newest member over at the U. Beautiful. U, oh, now it's Tell us what you were telling us earlier about when you were looking for a office in Boston. How did you find the union? Yeah, so in the Claude code browser, I was like, where should the founder of goodstander.com work out of in Boston? And the number one hit was
01:07
The union. Doing something, right? There's search engine optimization and now there's like AI optimization. Like it's a whole new field. So I'm glad we're doing something right. Yeah. I asking if you have yourself all over Reddit. Like I I heard that's a thing now. You just create your own Reddit posts and say best, best coworking space in Boston. Shout out to Shom Shukla who's my partner in the business and he does all the technology stuff. like this is happening. I don't really understand it, but funny story is Shom had Manus write an email for him recently.
01:37
And it signed it, it's named Sean, Sean Shukla. It signed it Sean Patel. Just because like, it's like a little racist. Like it just has to guess what the next word is. You know, that's basically how LLMs work is, uh, predictive. And so we put Patel after Sean, just because.
01:56
because Patel is the smith of the... You think that he's used it enough where it kind of knows him by now. You would, but I guess, I don't know. Well, let's get back to Caleb here. So that was an unpaid, unsolicited event. That's the real deal, how you found the union. Yeah. Beautiful. So today, first day in Boston, moving out from the Berkshires, first day at the union. Within 30 minutes of being at the union, an insurance broker invites me into his team meeting where I meet his team.
02:25
and they want to learn about the company. So immediate sort of value being delivered. This is totally unprompted by the way. I just met Mark a few minutes ago. Anyone can be a guest folks. Anyone can be a guest. we go. True story, there having a coffee and I was like, wait, just save this. We're doing a podcast in 25 minutes. This is really interesting. So I texted these guys and here we are. And I've been following Mark on LinkedIn for I think over a year. Thanks man. Yeah.
02:54
And then we didn't say you liked it, dude. It is actually good though. But yeah, and then a couple hours later, we're having this conversation and now it's 1.30, two o'clock, you know, day one. Hell yeah. Welcome to Boston. Yeah. Well, typical experience here. long were you Berkshires for? I was there for a year and a half. Okay. So I was...
03:18
Prior to that, I was working on Nantucket and I was doing affordable housing. They were trying to solve the housing crisis on the island. How do you do affordable housing on the It's kind of the canary in the coal mine of what the housing crisis is going to look like. A brief aside, but it's employee housing and we call it the Nantucket shuffle where you're living in a benefactor's-
03:42
spare bedroom for a few months and then sort of moving along. But anyway, yeah, I moved out to the Berkshires to redevelop North Adams, which is one of sort of the original American Rust Belt towns. It was challenged after textile, textiles moved and then electric manufacturing left. Interesting. Yes. So you got to tighten it. going to keep it. So it's going to throw you off.
04:11
So textiles, Rust Belt City, you're in North Adams after- It's like, what, an hour and a half outside Boston? Yeah, two hours. Two hours, okay. How, so has it kind of give us a little history on, you said Rust Belt, but like, is it up and coming? Has it started to get redeveloped? Is it like prime birch years? Are you- Trendy? Airbnb-ing, like what's the deal with North Adams? Yeah, so I went on a road trip throughout New England looking for a market.
04:40
because I had some capital to work with and I wanted to find the place that I thought was going to most rapidly appreciate. I was up in Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and I went all in on North Adams because it has two things going for it. It's a cashflow Ohio style market with nine, 10, 11 caps, is
05:08
impossible to find elsewhere in Massachusetts. Doesn't exist. The only, essentially the only. Maybe like Springfield and Holyoke and like the bottom of the barrel type cities. Yeah. So you can buy cash flowing buildings. And then it also has the appreciation story, which is it's 10 minutes from Williams College, which is one of the top universities in the country. The Williamstown, which is a 10 minute drive away has doubled the property values and their faculty.
05:38
are priced out of the town. So they're now buying properties in North Adams. And so you have both the, and you can also look at the data, but you're seeing that rapid appreciation in recent years in North Adams. So it's both a value, priced value with the appreciation story. That's pretty cool. It's awesome. So are you buying?
05:59
Primarily multi-family. just going to go look at some real estate north out of single family, multi-family, both Airbnb. We had Willie on and he's doing Airbnb. I don't know. It was the second home that he bought that he's also using as a rental. But I don't know where in Berkshire. Regardless, I love the thesis. I think it's super interesting. I go to Taurus Welcome a lot. They should sponsor us. We should pitch them because I've mentioned it's like a super cool, like Howard Johnson updated.
06:28
and now rents for, suckers like me for like $800 a night. That's like what they do with like the verb. Verb or verb. That was a hojo. It was? It was. And now it's all trendy and they have air streams and DJs. Sushi restaurant. So your thesis is affordable housing though. what are you, what's your play there? Short term housing, no? short term. Workforce. I've had different.
06:54
lives in real estate. So yeah, the affordable housing, I write about affordable housing and I'm sort of involved a little bit in that area, but this was traditional. But this was traditional real estate investing and development. So one of the buildings is all short-term rental. So it was vacant. There was one tenant, found them a new apartment, and then the entire three units are short-term rental.
07:22
The most recent building I did is a four unit long-term rental uh with purchased added bunch of value and then released most of the building. Cool. Short-term rental as Airbnb, Verbo, that type of thing? Yeah, the three unit building is all short-term and then the four units long-term. Have you ever done short-term rental before? That was my first. I I self-manage it. I still manage it now and respond to messages.
07:48
giving more cash to the main cleaner and my girlfriend to kind of like offload that as I build this tech company. Yeah. What uh do you like short term or long term better? Since you have both kind of in the same town. Well, you know, it's very contextual. I think in North Adams. uh
08:07
short term because of the long term tenant, the risks that come with this long term tenant population, maybe similar to like a new Bedford, where there's, they're just elevated eviction rates. They're elevated uh tenant problems that you're dealing with in this market. It's a good transition here. So this is where our conversation went next. Just the idea that
08:36
Massachusetts is a fairly hostile environment politically in terms of like the new legal ah laws, excuse me, ah for landlords and tenants. And so you're sort of working on a solution to that overarching problem. Yeah. So I was happily redeveloping North Adams and like, was like, you know, this is my career now. I'm going to.
09:02
accumulate these buildings and then bring outside investment from Boston to North Adams and manage the properties. Then I started having tenant issues. I'm going through an eviction now, I just signed an affidavit for serving a notice. I realized that
09:26
There are so, there's such a large surface area of risk as a landlord in Massachusetts. I'm sure many people here and in the audience can relate to that. And I, I've realized that my tenants knew the game better than I did. You know, they're getting free legal aid. They're, they're now using AI to identify all of the, the loopholes. so landlords in Massachusetts are now getting hit on two.
09:51
on both ends, the state is becoming more restrictive with security deposits and all sorts of penance rights. We just narrowly avoided this imminent rent control. And tenants are getting more educated and more weaponized with access to AI. And I was losing sleep over this eviction and identifying all of the areas where I was exposed.
10:20
And so that's why I started building Good Standard. Is it a simple like non-payment issue or is it some other kind of situation, if you don't mind me asking? Yeah, well, the one is non-payment. And then there's another which is not in a formal uh dispute, but a very informed tenant strategically submits uh building department complaints to set themselves up for... uh
10:49
retaliation protection. Can I give you a piece of advice? Yes, please. Respond to every one of those and be super open, overly communicative and transparent. Not as, you know, not as any kind of way to like one up the tenant, but just to show that you're not some person that's not going to respond. Because I've had issues where the tenants will say, oh, you know, you've got this issue in the building and I'm going to talk to the health department. I'm like, great, let's talk to the health department together. Like, let's see if there's an actual issue. Because sometimes they kind of overblow.
11:17
what situation to sort of do what you're saying. And I'm not implying that good people do that, but sometimes that happens and uh it's a way to mitigate it. And I completely agree with you. So you found out that, you know, apparently, you know, according to Ayanna Pressley though, there's too many, ah there's not enough tenant protections. Tenants here are being thrown out on the street overnight. That's not necessarily the case, is it? No, not at all. And what you just said is, is something all
11:47
of the landlords in Massachusetts need to hear and that's what we're integrating into Goodstander. It's reviewing all of your messages before you send it. It is flagging risks from messages and maintenance requests coming in from the tenants. And I've talked to tenants about the platform too. And at first they're hesitant because it's giving legal aid to landlords, but it's actually great for tenants because it is nudging landlords to do the right thing.
12:15
get the heat on in 24 hours to fix the water leak because all of these things do create the risk of counterclaims down the line. is it a, forgive me, I haven't looked at the tool, but is it like property management meets AI meets legal? how would you define the tool in terms of where it belongs kind of in a landlord's
12:44
Tech stack. Tech stack, I guess, yeah. Yeah, it is property, it's a property management system. I call it a landlord operating system. So it is a property management platform that integrates legal guidance into the daily operations. And so for example, we have a risk radar which is scanning your entire portfolio, including the messages and maintenance.
13:13
ah and flagging the highest risk items that you need to deal with. We're creating the leases, the notices to quit, the court report. So if there is an issue, you create the court report and that's doing the 10 hours of discovery that your real estate attorney would be doing. So you've now just saved 10 hours of legal hours because it has accumulated all of the relevant text, video clips, we're integrating blank cameras. So it's an extremely comprehensive.
13:42
Report, you just hand your lawyer and now you're ready to go with the eviction. what I like about that is it starts my challenge often with any dispute is like if you knew where this was going to go, you would be so much more prepared once you got there. But these things never just automatically like, hey, in six months, I'm going to take this action, file this complaint, and that leads to this. And then I have to go back through hundreds and thousands of emails over the course of months or even years and reassemble that whole case.
14:12
That's true of change orders. That's true of tenant disputes. is that what it does? It aggregates in real time. like all communications. Everything. Between tenant, landlord in one platform. And then if you have issues, you can easily export everything. Exactly. It's as if you had a Massachusetts real estate lawyer sitting next to you, looking at every single thing you have ever done.
14:42
with a tenant, with a building, with a unit, and at a click giving you the report that you need based on the issue. If it's non-payment, if it's uh non-renewal, any issue that's happening, is coordinating the data set to the use case. Can I ask you kind of a... Sure. I don't know. I don't want to ask weird questions, but...
15:10
Go weird. Come on, let's go. weird, but I don't wanna like try to like, tattoo, but- Go for it, Are you nervous that you're giving legal advice to landlords and that's like, you're not an attorney? And if something happens, then a landlord could sue you. This is something that we're thinking a lot about and we're talking to a lot of Massachusetts real estate attorneys about this. I'm running it only on my units until we have definitive, until we feel really confident that we're not legally exposed.
15:40
So yeah, for sure, you know, before we let other property managers and landlords use the tool, we're going to confidently, you know, have protection for ourselves. I would imagine you'll have obviously terms of service, disclaimers, that sort of thing. Before you just send this to the court, maybe have your attorney look at it, but you're still saving the prep hours maybe. don't know. Yeah. sort of thing. I want to dial in on one thing that you said and correct me if I didn't hear it right.
16:09
It will also review messages before you send it to make sure you don't say something that not potentially could harm you, but that may not be in the fairest light in terms of the intent. So it's going to review messages before an email or a text or something before you send it and maybe flag a keyword or something like that. Yeah. So in the Composer, so there's messaging in the platform like iMessage. And as you're typing the...
16:37
model is running what you're typing against every local state and federal law relevant to landlords. And it's giving you an indication, looks good, high risk, here's the law that this uh potentially violates, here's the issue with what you just said. And so that we feel pretty good about in terms of legal risk. There's a feature that is high risk for us.
17:05
which is the suggested reply where the landlord clicks the button and it types out what should be said because then it's, you know, we're trying to figure out is that the company good standard saying that. ah So we don't know if we're going to go live with a suggested reply button, but we like the review of what the landlord is typing. That's interesting. Yeah, I was going to say, mean, it's it's to Mark's point, it's tough because when you're having, you know,
17:33
essentially these are relationships, right? Every tenant, every resident there, it's a relationship and you want to put your best foot forward. And sometimes it can bite you in the ass if you're like, oh, you know, I'll take a look at this thing or yeah, I know that's an issue. And um not even if it's intended to go that way or whatnot, but I do find it very, very interesting. And I will give you an example of something where I had to kind of, I did use AI on my end to just make sure I was covering my ass. um
18:02
was returning security deposits. had some people move out. So end of the month, always busy. And we're processing invoices and this, that, and the other thing. And it's funny, the MAR, Massachusetts Association of Realtor, standard lease, says you can, if you hire an attorney or pay an attorney to enforce any part of the lease, that is something that you can charge and deduct. Whereas Massachusetts security deposit law says absolutely not. There's only three things you can deduct.
18:30
So I find it interesting that a standard boilerplate legal document put out by an association of realtors conflicts with Massachusetts security deposit law, but it did save me from an erroneous deduction. are the three things you can deduct? ah Obviously damages, any back rent, and ah I forget the third, but it's like, it's this, this, or this. And that's it. I hear you on that concern. I think that is something interesting to balance too, is like the way that you communicate with your tenants because
18:59
You know, you will get a bad Apple who's going to try to take advantage of a situation, but some people may be on the line of like, they can be great tenants or you can push them to a place and it, they might respond to how you communicate. if the stuff you're sending is fairly legally sounding and, like almost offensive and posture, then maybe they feel like they need to also act in this act the same in, kind. I don't know that's sort of a dynamic that.
19:29
I tried to avoid. Yeah, I know what you're saying. Like you don't want every communication to be like a formal letter. I'm very casual with communication and try to be friendly in that regard. And 99 % of the time it's fine, but it's that 1 % that will chew up like 99 % of your time. I mean, I'm sure there's a dial that you can use that I say like, make this affable and friendly, but also keep me protected from saying stupid things. Like your tool, as you were explaining it, I was thinking about my brokerage too.
19:57
and how much I'd like to have my agents, especially who do rental listings. Like you just know you're getting set up sometimes these texts come in. It's like, hi, I'm a elderly in a wheelchair and I have a newborn baby on the way. Is this unit available? I'm on section eight and look forward to your reply. And you're just like, holy shit. anything I say. the ESA and the 14 reasonable calculations. Yeah.
20:26
You can't not reply either. That's also like, yeah, you're to be very careful. So anyway, if you, if you have one for a brokerage, a spin-off, I'm interested. you developing this yourself or is your background in tech? What's your background? Yeah, I come from a real estate and tech background. I've done tech startups. I've done other real estate tech startups. Uh, and so I'm doing a lot of the development myself. I have a senior engineer that's reviewing the code. You can also build. Claude agents to.
20:56
on a loop review your code for bugs. uh So you can do a lot of the quality control yourself and you don't have to be technical. I I took one coding class in college and then just taught myself very basic things, but it's really unnecessary now. And I think it's to be seen how exactly CTOs fit into startups. I'm kind of negotiating that now, definitely as an advisor with advisor level equity, but
21:27
We're kind of figuring out if a co-founder level is still necessary as a CTO. So to answer your question, yeah, I'm doing most of the programming myself with Claude with reviews from Claude and from a senior engineer and similar with the legal too. Working with Claude for the legal and then having that reviewed and uh that's been for the pilot sufficient and then when we roll out,
21:56
That's when we, need sort of this bigger stamp set of approval from a master's law firm standing behind it and either a full CTO or, you know, additional testing. Makes sense. Awesome. Seems cool. Do guys mind if I give a quick shout out to our sponsor here? Not at all. All right. Well, thank them very much. Yeah. Our official sponsor, DrewTex Windows. When, let me start this again.
22:24
Ah, you botched it. I'm just adhering to the headlights. All right, redo. Listen, I think as far as performance and durability and value, Drutex Windows, I like to say we're not just paid spokesmen, we're also customers and clients. And between the three of us, we've installed Drutex Windows European Tilt and Turn, very high performing windows in over 200 units around Massachusetts. you know, look forward to work with them on the next one and the one after that. So if you'd like to get in touch, shoot us a DM.
22:53
or visit their website. also put a link in the show notes as well. Thanks, absolutely. Caleb, any other thoughts here, ways folks can get in touch with you? Learn more about the tool. Yeah. Is there a release date anticipated? We have a live demo in landing page at goodstandard.com. Like Good Standing, but ER. And feel free to reach out to me at caleb at goodstander.com.
23:22
And thanks for having me guys. Thanks everyone. Thanks, Caleb, for joining us. And thanks for doing something that can potentially add tons of value for operators and housing providers. So appreciate it. Amen. Yeah. Thank you for listening, reviewing, reading, subscribing, and we'll catch you on the next episode. See you. Later.