Kaylin Goldstein

Kaylin Goldstein • From College to 100 million in Sales

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Today we spoke with top producer Kaylin Goldstein of The Goldstein Group. Kaylin started her real estate career directly out of college and has grown it to over 100 million in sales. She’s also built a successful team along the way. In our conversation she talks about how she grew her business as a relatively young broker, and how she’s mentored her teammates to become equally successful!

Kaylin can be reached at 312.909.1682 and kaylin@atproperties.com.

The Goldstein Group


D.J. Paris 0:13
Hello and welcome to another episode of Keeping it real podcast the only podcast made by real estate agents for real estate agents. My name is DJ, I am your host, at through the show a couple of quick announcements before we get on with our really fantastic interview with Kailyn Goldstein. Number one, this is episode 15. And as of this point, over 2000 of you have downloaded an episode of this podcast. So thank you for telling a friend. Thank you for sharing this with other brokers that you know that you think could benefit from listening to these interviews. Also, we have every month Carrie McCormack and I also do a Monday market minute, and she is taking your questions. So if you have questions or top producer, you can submit those through our website speaking of our website, which is keeping it real pod.com. Also, we’re on Facebook too. But on our website, you can find all of the episodes that we’ve ever done, as well as if you subscribed via iTunes or Google Play. There’ll be listed in your podcast app as well. And lastly, we are taking sponsorship opportunities per episode. So if you have a service that you think could benefit from getting into the ears of about 2000 brokers, you can reach out to us via our website, keeping it real pod.com or Facebook or Twitter any of the other ways you can reach us and say hey, I want to sponsor an episode. We’re going to be starting doing that here in the next week or two. So Thanks in advance and now on to the reason you are listening, our awesome interview with Kailyn Goldstein.

Hi, today on the show, we have Caitlin Goldstein. Caitlyn is a top 100 agent at properties and a top producer recognized by the Chicago Association of Realtors and at property since 2013. She’s a strong negotiator and has a vast knowledge of the Chicagoland market. Kailyn is from Peoria, as am I and I grew up around her family’s business and learned upon about entrepreneurship from a young age. She attended University of Iowa and received a BA in marketing. Upon graduation, she was recruited by a boutique real estate brokerage, and in 2010, she transitioned over to add properties, and now oversees her own team called the Goldstein group, and they have eight agents and over 100 million in sales. She enjoys helping new agents train and develop into future successful realtors. She has been featured in Chicago agent magazine and who’s who. And Kailyn resides in River North with her husband Garrett and their two golden doodles, Lolly and Lewis is that lab?

Kaylin Goldstein 3:05
That is a golden doodle. I have a regular and a mini

D.J. Paris 3:10
Awesome. Well, welcome to the show.

Kaylin Goldstein 3:12
Thank you so much. Very happy to be here.

D.J. Paris 3:15
You’re my very first Peoria person and I I could not be more excited because I so rarely get to talk to people from pure idea that I didn’t like go to high school with so and so. Do you go back for your reunions? That’s the first thing I have to ask.

Kaylin Goldstein 3:31
It’s a good question. So I was bad. And I missed the last one. I had an out of town client in. But I try and go back for Thanksgiving and the holidays and go to all my favorite restaurants. So usually a couple times a year, but um, I’ll try and make the next reunion.

D.J. Paris 3:47
Well, let’s let’s talk about your your business because you started, you know, you went you went to school in Iowa and then right out of school, it sounds like you went straight into real estate. So tell me a little bit about sort of why you did that. And how, how that how that, you know, was trying to build a business as a really young person.

Kaylin Goldstein 4:06
Yes. So very unique. You know, I started definitely at a young age. I had been interviewing with multiple companies, you know, they came to the campus and we met with all different sorts of companies. I mainly was interested in something in sales or marketing, which was kind of my background and college. Pharmacy sales was really big at the time, I interviewed to sell printers, kind of everything across the board. And then I met with a company called home Scout Realty and had a few interviews and I decided, you know, it’s something that sounded really interesting. I liked that, you know, it had that entrepreneurial background kind of make your own hours you’re responsible for your business. It kind of reminded me of growing up around my family’s company and that sort of thing. So, anyways, so I got the offer and I decided to take it and my parents were super supportive, they thought it would be a great field to get into. At that time I had started, I think it was summer of oh eight, and the market had kind of started to transition, you know, we were going downward market. So, you know, we did a lot of rentals, it was very focused on rentals, condo rentals, manage building rentals, and that sort of thing. Most of our leads came from Craigslist, so I was meeting people, you know, I had never met before. So, you know, it’s really interesting, I worked those leads, and it all went well. And then through the years, you know, those people started coming back to me, whether it was looking for another lease or looking to Now eventually by and referring their friends. So really kind of interesting how that all started. And then I decided to transition over to app properties in 2010, one of my other colleagues had just come over, and I really had always thought their marketing was so neat. So I came over in 2010. And I started working as an assistant for two top producers. So I had their business to, you know, to attend to, and then I was still working my own. So it was quite a bit.

D.J. Paris 6:20
Yeah, no, that’s so interesting. And also, you know, sort of, I guess, in 2008, the rental market was definitely for, at least for a new person entering the market, certainly, you know, the, probably the most lucrative area or the most active area of real estate, you know, because of the crash, and then also your age, everyone, you know, is renting anyway. So it sort of seems like, you know, ultimately, it was really sort of fortunate, because, as you said, as you, you know, build these relationships with renters, over time, they transit, some of them transitioned into purchasing. And I think that’s something brokers, oftentimes, new brokers in particular, oftentimes, sort of maybe forget, or easily overlooked is like, every buyer was probably a renter at one point. And it seems like that would be in particular, if you just don’t have, you know, 50 friends that are looking to buy and sell homes, the day you get your license, which of course nobody ever has, it’s a good opportunity just to sort of keep the ball rolling, while you’re building up, maybe those future opportunities. It sounds like that’s sort of how it worked for you.

Kaylin Goldstein 7:23
That’s correct. Yes. And I think that’s really well said, you know, I see it every day, I think one of the biggest things for these new agents is just building their business and having people you know, get to know that there are real turnout, whether they came, you know, straight from school, or most who came from a different career. And I think, you know, some people get discouraged, because it does take a while it takes a while to get going and to really work those leads. But, you know, I’m just so thankful how I started and building the rental business that I did, because it really transitioned well into people buying and now selling. So I always tell new agents, you know, on my team, or when we talk, it’s, it’s something to really consider, you know, rentals aren’t for everyone. I know, there’s some agents who just don’t want to do them. But I find you know, it’s, it’s a great way to meet people. And, you know, it’s it’s good income. So,

D.J. Paris 8:18
yeah, I agree. And certainly, in particular, if you’re a younger person, like you are entering the business, it just seems like that’s the, you know, sort of most obvious thing to do, because at least people you know, are likely doing it anyway. And, and the good news to about, you know, in other cities, it’s not quite this way. I know, in New York, oftentimes, the renter pays the Commission. In here in Chicago, of course, the the landlord does, or the management company, or certainly not the renter. And so it makes it you know, a really nice way to slide into real estate, where you’re able to work with with renters. You know, in the interim, while you’re building up your sales business, I think it’s very, very smart. And so talk about when you went in, because now you have your own team. And I find that so interesting, because you’re relatively young, for having this, you have a large team, or at least to me, it’s large. Talk about sort of that transition of how you went from just you to now having, you know, a bunch of people working with you.

Kaylin Goldstein 9:14
Yeah, so, um, you know, I stayed on for an assistant for probably a couple years, and then, you know, it got to be a lot working everyone’s business and helping out that sort of thing. I didn’t want to lose focus of my clients, you know, who are starting to look more to buy and then sell that sort of thing. So I decided to kind of take a step back, and I partnered with another app properties agent who’s terrific, and we kind of, you know, worked together for a while and had a smaller division. And then I decided to kind of we parted ways do our own thing, and I rebranded and so now I have terrific team members, my sister in law’s on my team, which is super fun, and she met a real Nice guy in real estate class, and then we have a few newbies who just started. So it’s just really neat. It’s nice to have the camaraderie to go to events together. And I just think it’s so helpful for new agents out there who, you know, you go to real estate class, you learn all these things. And then it’s kind of like college, you get out to the real world, and you have to find out what applies and learn the day to day things, from contracts, to inspections, to getting the deal to close. So I think it’s really been nice in that regard to kind of watch these new agents grow and see their business grow as well. Yeah,

D.J. Paris 10:37
no, I yeah, I can imagine that it is super rewarding. And you seems like you put a lot of time in with, with your team members, in particular, the newer ones? What are some of the suggestions you have for people who just, you know, have gotten their license? As far as how to go about marketing themselves? Or getting, making sure people know what they do? You know, what are some of the suggestions that you would say to somebody brand new?

Kaylin Goldstein 11:04
Yeah, so I think, you know, social media in this day, and age is so important. And I think it’s a great free way just to really, you know, create a presence and let people know that you transitioned. So I really stressed that, you know, just start, you know, working your social media. And also, we have something without properties where we can send out a blast. So sending that to, you know, all your emails of friends and family. starting to do some mailers, you know, that’s always great, I have one girl and I said, just take your wedding list and right, they’ll be there’s your clients right there to start with. So I think it’s just a matter of, you know, doing things that aren’t necessarily super expensive, right off the bat, like I if it were me, I wouldn’t go by a billboard right away. That sort of thing. And then I think, you know, also, I’ve had a lot of success of sending open houses, I’ve met some of my best clients that way over the years, so you know, something to see if that works. And, you know, see what works for you classes are great, especially just learning the different systems, there’s so many classes through the MLS now, just really getting the groundwork in place. So you can be as knowledgeable as possible and apply those things while you’re growing your business.

D.J. Paris 12:24
Ya know, I love I love all of that. It’s so interesting with open houses, because over the years, and at the firm I met, we have lots of brokers. And for years and years, everyone I talked to said a huge waste of time open houses. And then once in a while, I’d meet a broker who had joined our firm, and I would ask them, oh, how do you grow your business? Just, you know, I’d be asked a lot of those types of questions. I was curious. And once in a while, somebody would say open houses, and I’d say how are you? The only person have like, everyone else claims their huge waste of time. And yet there are people like yourself, who have had tremendous success with them. And I obviously not every open house is created equal, there certainly are ones that maybe you know, are going to produce better results. But I’ve always said to new brokers, if it was me, and I had no clients or I was not that busy, I would probably send out an email to certain other brokers at that firm. Hey, if anyone you know, here’s the area I kind of specialize in, and if anyone’s interested, you know, to, if anyone would like me to do an open house for their property, you know, give, you know, give me a call. And it is not it does not happen that often. And I’m always surprised. Because I think, you know, it can actually be helpful. Do you? Do you think there’s something you did differently to have more success with those?

Kaylin Goldstein 13:41
Yeah, you know, I think it’s just a matter of reading people. You know, as they come through, you’ll have some people who come through and they don’t want to be bothered at all. So I would say, you know, let those people go through follow up, if nothing comes from it, I wouldn’t get too down on yourself. But there’s other people who are really receptive. I work a lot with, you know, pocket listings and stuff coming on. So often what I’ll do is follow up and just say, hey, you know, if you’re not working with an agent, I’d be happy to set up a search for you. And I have access to off market properties as well. So I think just kind of leaving them with a little bit of intrigue helps us report and then you know, they’re, they don’t think you’re out to get them and sell them something right away. Because, you know, obviously, the leads you have are the warmer leads, such as your friends and family know that you’re out for their best interests. But people you meet on the street don’t necessarily have that same perception. So I think that’s definitely really important. And then you know, just building a relationship with those people I think if you’re able to find something different for them or be creative and not just do the same old thing every day by setting up a basic search, though value that and you know, those people become loyal. It goes back to to some of my rental clients when I first started, they just you know, they come back to when when they need to move, or they can refer a friend.

D.J. Paris 15:08
Yeah, no, that is so well said, and I have always thought, or recently in the last few years, I’ve thought this and tried to communicate it. And I think I’m right. And it’s might sound a little harsh, but I think it’s actually a good thing for, for brokers to hear is that I don’t think the public needs you to just set up an MLS search, they can find those properties, and oftentimes, they’re going to do it, and they are going to find those properties with or without your help. And in fact, even if you’re helping them, they’ve already found probably them anyway, because there’s a million ways to get to not necessarily get access to the properties, but certainly to see what’s available. So I think that in the past, it wasn’t as accessible years and years ago, where people really did need brokers to to find these properties. So I think what’s great about that is it takes a lot of the pressure off of the broker to only just be setting up, you know, these the searches is to be able to, like you said, be more creative. It’s like, Hey, by the way, I have some access to listings that you probably wouldn’t have access to. And I, you know, based on what you’re looking for, I’m going to do some deeper dives and get more creative. So you’re not just showing them the same things they’ve already seen on Zillow. I think that’s really, really smart. And I don’t know if you if you agree with that, that thought but that, you know, the access to sort of the information isn’t isn’t as locked, as it used to be, you know, people can can see properties, and then they are doing those searches, I think, but the broker gets to do everything else. And I think, and also, of course, finding properties. But I think there’s so much of the process that frees up time, I think for brokers to really get creative. I don’t know if you if you’ve had that experience or not. But

Kaylin Goldstein 16:52
yeah, definitely. I mean, it’s, it’s just amazing, you know, I think just doing things, you know, as differently as possible, but offering some value, you know, anyone can go click an agent online and find them. But I think just getting to know these people and offering something different. Whether it be you know, something, you know, about a particular building or a location, you know, for example, I always tell my clients, you know, if the property’s on the L That’s up to you. But you know, for resale, it’s definitely something to consider. And they go Oh, yeah, that’s a good point. So just, you know, putting the different pieces together and helping them make the best decision for the long term.

D.J. Paris 17:34
Yeah, definitely. And let’s talk about some of the sort of you do a lot of team building exercises, which I think are also probably really helpful in not just building up sort of team camaraderie, but also sort of the skill sets of the team. So you talked about, you have a sort of a program you run called fall in love with your neighborhood. Tell us a little bit about that.

Kaylin Goldstein 17:56
Yeah, so we just started that super fun, I thought it would be a great way to really jump into foul market here and do something different. So how we’re doing it is, every week, every other week, each team member on the team gets to pick a neighborhood, we’re kind of targeting the ones they live in. And then some of them are in the suburbs. So we’re filling in with you know, some of their favorite spots. And they get to choose, you know, something really neat about the neighborhood, something new, you know, something they wanted to try. So, for example, the first one, we went to a really cool restaurant in River North called barrio, and we all had some really good Mexican food. So that was really fun. And then this week coming up, we’re going to do cycle class in the west loop, which some of us aren’t the most athletic, including myself. So hopefully we make it through. But it’s really fun, you know, we we go we’ll do the classes or what have you, and then do lunch, and then we’ll post about it on Facebook. So it’s just another nice way, you know, to show our clients and our friends something else that we’re doing and experiencing in the city versus like just listed just sold the same old property stuff that they see on Facebook all the time.

D.J. Paris 19:13
Right, right. I think that’s I think that’s very true. And it also it it also tells a narrative of here’s here’s kind of instead of only Hey, we just listed and sold this property. Now Hey, look at here’s what here’s what we do. Here’s our personalities coming through and social media and I think one of the you know, one of the mistakes maybe brokers make is only saying just listed this property, check it out, you know, just sold this property. And those there’s nothing wrong with those posts. That’s great. But if you’re only doing that, I think it just it just the average person who’s your Facebook friend probably just glosses over it. If it’s not necessarily if they’re not in the market to buy or sell a home they might not really respond to that but they’ll respond to hey, we just went to an escape room with you know, this other members of my team and here’s some funny pictures and I think that’s that’s Actually, really. And also, it’s fun too. But I think from a social media perspective, it probably got gets more interesting engagement from from, you know, your prospects and clients, I would I would think,

Kaylin Goldstein 20:11
currently Yeah. And I think, you know, it’s fun for the team members, you know, we have two newer agents who are recently starting, and it’s a good way to get to know the personalities on the team. And I think that helps. And a lot of new agents, you know, they’re nervous, they’re, you know, either leaving careers or, you know, depending all different avenues where they’re coming from. So, I think it’s really a nice way just to kind of do something different from the thought of how am I going to get my next lead? And, you know, like, we spoke about, I think, on Facebook, you know, clients really like to see about our lives as agents and stuff like that. It’s, it’s fun to be able to relate and do things. And, you know, I It’s kind of like those shows Million Dollar Listing, I mean, I have more fun watching it and seeing what they’re doing on day to day versus sometimes, you know, the actual real estate stuff of it.

D.J. Paris 20:59
Yeah, and absolutely, one thing I did also want to mention is because you are currently rehabbing a house, with your husband, and talk about that experience, because I think that’s a really important experience. If if brokers ultimately are, you know, it gives them additional dimension and skill set, you’ll be able to, you know, share that information with future clients as well. And maybe you start working more more so with investors and developers, because you, you now have this experience. But taco, can you talk a little bit about that experience? And what that’s been like for you?

Kaylin Goldstein 21:35
Yes, so most importantly, we’re still married. No, it’s been good, we, we bought it not too long ago, and we’re rehabbing. So we’re redoing the BAS, the kitchen we tore out, we’re putting a new one in, and then we’re finishing off the basement. So it’s been really fun, you know, I love to pick finishes, I could have been an interior designer in my second life. But um, you know, it’s, it’s been really great to see what’s on trend and try and put that in there. We have plans to Airbnb, that property. You know, so we did a single family home and that way, you know, the neighbors won’t mind too much. So we’re really excited to oversee it. And I just think it’s a nice extension, you know, of what I do day to day. But with that said, you know, rehabbing or buying or selling I just think it’s it adds a lot of value to have gone through it. You know, buying is, is pretty straightforward. Obviously, there’s some ins and outs, but as a realtor, you know, you know, what you’re doing selling is is kind of an emotional process we did, we decided to sell one of our properties in the South Loop. And you know, I had put every fixture in there and picked out wallpaper paint everything and it was it was a little emotional. So you know, I think it’s really important as realtors to know what our clients go through. And it’s, it’s just a really stressful process, it can be not always, you know, you have your investors who aren’t as attached to their properties, but families who have, you know, had properties in their, in their family forever, it can be really stressful. So, I think that kind of helps and just to have a diverse pocket to offer to everyone.

D.J. Paris 23:23
Yeah, for sure. And I can ripple on that. Because we I had a condo that I sold, I’d done the same thing, put all the fixtures, that and all the finishes and, and everything over the years. And then when I went to sell it, and I knew I was pricing it more than it ought to event. And I did the classic mistake where I was just too emotionally attached to it, even though I knew there’s you know, and it wasn’t outrageously overpriced, it was just slightly overpriced. And I said, Oh, what we’ll see, you know, and I ran the comps and I still priced it above what I should have. And as a result, nothing happened for a few weeks. And I went okay, and it was like I knew better than to do that. And then ultimately ended up dropping the price and it sold, but it was like wow, if that if it can even affect me and I know better than now I know you know so much more about what the average seller goes through, you know, the emotional part of wanting to sell it for a certain price or because you have an emotional attachment or because you bought it at a certain price and you want you know there to be a certain amount of profit or, or whatever, but boy, I can certainly relate to, you know, to that experience. So much more now because, you know, I was sort of doing it to myself even

Kaylin Goldstein 24:36
definitely, and I think there’s just there’s more compassion that goes that goes into it not just there never was before but you know, I care about my clients so much but I think you know, just to help them understand where things need to be priced at and just understanding the process in general is is so important. And you know, even on the buyer side when when we go in and some of these properties needs to be redone. Some are overwhelmed And at the thought of what the price could be of redoing a bathroom or a kitchen, and others are just, you know, oh my gosh, how much time this is going to take. So I think that really adds value to be able to give not necessarily estimates, but a rough idea of how much money out of pocket and how long it could take just to kind of ease their concerns and see if they really can see themselves living in the property. Yeah, I

D.J. Paris 25:24
think that information is so valuable to consumers, buyers and sellers to be able to know or to ask their their broker, hey, you know, I was thinking about this, do you have any information about, you know, good, like, should I redo this kitchen? Should I not? And certainly, you can’t always tell them what they should or shouldn’t do. But you just being that knowledge source is so critical. Like, for example, I did not know that I could buy a property until at least a year after I could have bought a property because I didn’t have anyone that sat me down and told me I was renting this as a long time ago. And finally, somebody said, you should buy a property and I went, and I think I’m a relatively intelligent person. I went, Oh, I can’t do that. And they go, No, you probably can. And I go, No, no, no, no. I mean, I really didn’t understand how a mortgage worked. I mean, this was, you know, I was probably 30 At the time, and I really didn’t totally understand. And so I always think like, you know, there’s so much opportunity for brokers to educate their clients and, and somebody like me, I would have been way too embarrassed to ask like, how does the mortgage work? Thankfully, one of my friends who’s who’s a realtor said, you know, you can do this, and I was like, you’d have, you’ll have to explain that to me. And he did. And I went, Oh, my gosh, I literally had no idea. So I think you’re, you’re so right, about being able to, you know, provide that information to your clients. And this is also back to the rental thing, too. I mean, that’s a really specific example. But you know, if your clients are, if you have clients that are renters that are spending two grand a month, you know, on an apartment, they probably should be purchasing, or at least should know about what you know what it would take to do that. Obviously, you already know that, but let’s talk about I wanted to get to finish with this story that you had. This is so interesting. I’m not even totally sure I understand all of it. So I want to find out. So you, you were you were talking about or you’re you’re writing us about a Lincoln Square bungalow, that you had a couple purchase. And then there was some, as explained, like what happened at the walk through at the

Kaylin Goldstein 27:19
end? Yeah, so it’s super sweet couple. And we found this property had multiple offers, and we got it. And so it was so exciting at the walkthrough so crazy, you know, usually they leave the basic stuff, right, like the keys and the appliance manuals, that sort of thing. And they also we had found it was like a little cigarette canteen thing. And inside it had a treasure map. And it you know, you had your x and your little dots to go find the gold or the treasure or what have you. And I followed up with them. And I don’t think there was a treasure in the long run. But it’s just so funny that you know, you just find all these interesting things, what you see day to day on the showing, but you just never know what’s what’s you’re going to find. And these vintage properties are so cool. It was a vintage rehab to think you know, they’ve been around for 100 Some years and all the different families, you know, that have lived in them over this time. It’s pretty cool.

D.J. Paris 28:19
Ya know, super cool. So did the seller leave that cigarette? tid or it just showed up?

Kaylin Goldstein 28:25
You know, I think it was last this was a while ago now. So my memory is not the best, but I believe they left it and it was something that was there when they had bought as well. So it’s kind of one of those things that comes with the property.

D.J. Paris 28:39
Isn’t that wild? That is really, really funny. And so there was but there was no they were not. You were nobody was able to find a treasure.

Kaylin Goldstein 28:46
There was no treasure and I told him I said I think we should split this treasure if you find it but treasure lo and behold

D.J. Paris 28:54
that is a that is really that’s really funny. Well, let’s talk where if if any buyers and sellers or renters want to work with you? What’s the best way they should reach out to you?

Kaylin Goldstein 29:05
Yes, so I am always by myself. My cell is great 312-909-1682 and email caitlin@properties.com. And that’s

D.J. Paris 29:17
ka y li n and then also you can visit her on her website, which is Kailen goldstein.com, which, which has all your contact information as well. So thank you Kailyn it was such a pleasure speaking with you. I really appreciate your time and it’s some great suggestions for brokers who are looking to, you know, maybe who are newer in the business and definitely want to get ahead. But thank you so much.

Kaylin Goldstein 29:43
Thank you it was a wonderful time. Appreciate it.

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