Episode 382 - Matthew Simpson, co-Founder - LoLo

00:00:00 - Matthew Simpson

And so that began the initial discussion for what is now Lolo, which is, how can we help them stay top of mind with an item of value, with something meaningful and local, with a write up, with pictures. Just something that monthly goes out in an automated way.

00:00:20 - Bill Risser

You're listening to the real estate sessions, and I'm your host, Bill Risser. With nearly 25 years the real estate business, I love to interview industry leaders, up and comers, and really anyone with a story to tell. It's the stories that led my guests to a career in the real estate world that drives me into my 9th year and nearly 400 episodes of the podcast. And now, I hope you enjoy the next journey. Hi everybody. Welcome to episode 382 of the Real Estate Sessions podcast. As always, thank you so much for tuning in. Thank you so much for telling a friend. Today we're going to talk to another real estate entrepreneur. His name is Matthew Simpson. He is the co founder of Lolo. Lolo is a relationship retention tool. They curate a local gift of the month to help agents stay in touch with their sphere at a really affordable price. It's such a cool tool. It really lets these local businesses kind of shine instead of the big box brands that are always kind of used a lot by agents. So let's get this thing going. And by the way, we'll talk a little bit of ACC basketball too, so stick around if you're into that. Let's get it going. Matthew, welcome to the podcast.

00:01:25 - Matthew Simpson

Thanks for having me, Bill.

00:01:26 - Bill Risser

This is going to be a lot of know you and I met, we'll call it on the circuit, on the booth circuit, at the real estate events, hanging out. And many times we ended up pretty close together. And I love what you're doing with Lolo. We're going to get deep into that as well. But yeah, it's just going to be a lot of fun.

00:01:45 - Matthew Simpson

Today brings me back to throwing some postcards at you a little bit while you were on a call. I don't have any of those to throw at you.

00:01:53 - Bill Risser

Yeah, good. We're about 1000 miles away, right? 800 maybe. That helps a lot. So I know you're based in the Nashville area, right? Are you a native of Tennessee? Are you a Nashville native?

00:02:04 - Matthew Simpson

I am. I would say I was born in North Carolina, but it was only because my dad was in North Carolina for school and so we moved back when I was two and a half, so grew up all the way through high school in Nashville.

00:02:18 - Bill Risser

So I've been to Nashville twice. Once was way back in the day when I was working for the Padres. There was a business meeting I got to attend. I think the predators were in their first couple of years. I don't think they'd been around a long time, went to a Predators game, saw where the Titans play. They were building it. So that should put in your mind about the time frame I'm talking about. This is in the 90s, right? Late ninety s. And my second trip was recently for a conference and, man, Broadway and that whole area downtown and the riverfront. And I'm sure for someone who's grown up there, it's just kind of like, yeah, I'll take you down there. If someone comes to town, do you hang out down there yourself? I'm just curious, is downtown a part of your life?

00:03:02 - Matthew Simpson

Not really. I would say I go down there to go to Predators games, Titans games, and when a friend who's in town really wants to go down and see it, but other than know, it's become a little bit like a Mardi gras every. There's the streets are full, the bars are packed. It's a great experience for someone who's in town for a conference or an event or just to have fun, but not your everyday night on the town. For someone who lives here, it feels.

00:03:34 - Bill Risser

Like living there is much like living in Vegas, right? There's a whole community of people that live there and work there and do their thing, but they're just not going near the strip for the most part. Right.

00:03:43 - Matthew Simpson

As much as I spend time in Vegas, I would say that's a great analogy. Know, there's a lot of people that would say they live in Vegas and haven't been to the strip in months or even longer.

00:03:55 - Bill Risser

Yeah. Let me ask you this. Your favorite part of living in the Nashville area, growing up there and living there. And maybe to add to that, what's the biggest misconception about. We'll call it Music City USA.

00:04:07 - Matthew Simpson

Well, when I think about what was so special about growing up in Nashville and then comparing it to mean it was always the people. The people were just so kind, thoughtful, welcoming, just a really community centric vibe. And as it's grown, we've had a lot of people from a lot of different places move in, and some of that has changed a little bit. But I still think you would hear a lot of people that really enjoy the community aspect of Nashville and the kind of feeling that the people provide to each other. I think it's also because there was a very unique groups of people. There's the musician community, there's the business community, the healthcare community, and all of these kind of respected each other. I don't think you find what you would find in some markets, like in LA or something, where there's a very celebrity aspect to things. At least when I was growing know, I knew or met different people in the music industry and it wasn't much like you'd bother them or do anything, it was just like another person. And I think that was probably nice for people in the music industry and one of the reasons they've continued to grow and be respected in this community.

00:05:18 - Bill Risser

You mentioned, you already mentioned the titans and the think, I know you're a big sports guy, right? I mean, so it's got to be great to have those teams. Actually, I think you remember Terry from a couple of the conferences, and we actually went to a Nashville sounds game at that conference we were at. So you got minor league aa baseball there as and I was looking it up and I don't follow MLS enough to have known this, but you've got an MLS team there, Nashville SC. So it's pretty cool. You got just about everything in the college world. You got Vanderbilt, which is an SEC school, but seems like their sports levels never really kind of up to snuff with the rest of the conference.

00:06:01 - Matthew Simpson

Well, growing up, there were none of these pro teams here, so Vanderbilt was the ticket. When I was a kid, my grandfather went to Vanderbilt, played basketball at Vanderbilt. I was ingrained in Vanderbilt as a kid. There really weren't many other options. And David Lipscomb, which is another university, my dad went there and my know, that was what we grew up going to and they had a good basketball team and that was kind of what we cheered for. They've always had a little bit of trouble in the football world and I think it will continue to be that way. It's a tough ticket in the SEC. It's hard to be a Vanderbilt fan. I think you always hear people say that, but it's a great school and so there's a lot of awesome people who went there and live here and try and support them as much as they can. But it is easier now to be a Predators fan or a Titans fan or a Nashville SC fan or a.

00:06:58 - Bill Risser

So, you know, we've had a few the in different cities around the country, and I know that you played basketball growing up. You're a hoops guy, you played some major college basketball, yet you didn't go to Vanderbilt. I want to know what your grandpa had to say and then where did you end up going? Let's share that with.

00:07:20 - Matthew Simpson

Know. As I said, I was born in North Carolina and so growing up I was actually watched the ACC a lot. My dad had done some residency at North Carolina UNC, so I was a Targill fan, but just paid attention to North Carolina schools and always felt like I would like to go back over to Carolina. And so I ended up going to Wake Forest University for college and just had the good fortune, honestly, of joining a team that Tim Duncan came in with me in that freshman class and really the rest is history because he wasn't highly recruited but turned into one of the best players. You know, we had a great team for a few years and as I was telling you earlier, I didn't get to play much, but I got a great seat to a lot of great games. Unfortunately got injured my sophomore year and then kind of never really. I was scraping to get to the level to be able to play to begin with, but after my injury, it was a little hard to really recover. But great experience all the way around, great teams. We won the ACC championship twice.

00:08:25 - Bill Risser

Tim Duncan's got the reputation of just being one of the know, just one of the coolest know that's played in the NBA. You got to hang out with him in college. I'm just going to assume that's who Tim Duncan was.

00:08:37 - Matthew Simpson

Yes, that's. That's who he mean. He was very shy. Honestly, when we first got to wake Forest, he was younger than everybody else, started school a little early and came from the islands, so there's not a lot of connection to us university system or experience. So he and I were really close freshman year as he got to know everybody and just such a nice guy and always thoughtful and pretty much the Persona. You see, he's not looking for attention ever.

00:09:07 - Bill Risser

Yeah, that's cool. Seems rare in today's sports world to come across. That's very cool.

00:09:15 - Matthew Simpson

If it was in today's world, I would say he would not have a Instagram account, he wouldn't have Snapchat account, he wouldn't be someone who's blowing up Twitter. He would be silent, working hard, let his game do the talk.

00:09:30 - Bill Risser

That's great. So I have to ask you this question, because growing up in San Diego, I adopted a team on the east coast. You have to pick somebody, and for me it was the early 80s. Mike Jaminsky, Ernie Banks. It was Duke, which I take a ton of grief for nowadays because they're not well liked. Who was on those Duke teams, obviously, that you beat out for the ACC championship back then?

00:09:57 - Matthew Simpson

Yeah, I mean, I think when my freshman year, they had a great team. We beat them at Duke, but that was the final years of Grand Hill and those guys, and then it was basically Woja houseke, and they kind of had a downturn for a few years. Coach K. Took a year off during that time, and so we did really well against Duke. The whole to. I'm not sure I want to say this out loud, but I think we did not lose at Duke during that time. So we've probably lost at Duke almost every time since then. They just had a little bit of a downturn during that window.

00:10:37 - Bill Risser

All right, good. Wake Forest, a private school, really well known on the education side. What were you going there? What were you studying as you were there as well?

00:10:45 - Matthew Simpson

Well, I started actually with a mathematical economics major, and back then it was really, I just looked at what was the classwork that I enjoyed, which I really liked, math and what paid well as a graduate. And I got into that program and decided that while I liked math, I didn't like math as much as some other people who were actually much better at math than I was. And so I shifted to just a business degree and got a degree in business.

00:11:20 - Bill Risser

What were you thinking of doing then with that degree as you were leaving? Because I know where you end up. Right? You're heavy in the development of software. We're going to talk about all that. But what was the first thing out of school?

00:11:32 - Matthew Simpson

Well, I was always interested in what was happening with technology. There was plenty of friends of mine and one of the guys I ended up going in business with who just played on computers and liked to code and liked to learn things on computers while we were at school. I wasn't necessarily that. I just was fascinated by it, but honestly, I was just looking for a job that felt comfortable and felt like a actually did. I got an internship with Pfizer after my junior year and worked for Pfizer this summer between my junior and senior year and had a company car and a full paid job. And it was a real position that was designed to then transition into a regular role afterwards. But I realized during that time that there was a lot of excessive paperwork back then, spreadsheets and documenting everything that you do for each layer of management that you had to report to. And it felt like it was not the kind of fit for me. While I really liked the people I worked with, I thought they were great. I just didn't really feel like that was going to be a fit for me, as most people that know me know that I tend to not be as enamored by authority over what I'm doing. I like to kind of find my own path. And so when I went back to school, I only had a semester left anyway. And I did the semester and then moved to Aspen, Colorado, worked for Aspen Ski company, kind of tried to figure out what I was going to do. It was awesome. Got a lot of skiing in love, Colorado, and then formed a business while I was there. Basically a design business ad agency. And really, the rest is history. I never went to another interview.

00:13:14 - Bill Risser

I was going to say, the entrepreneur runs deep in you. You want to create your own things, and that's great. Let's talk about then some of the things as you kind of progress through the 2000s. Right? Let's go there. And I look at it this way. For someone like you, who's got the business savvy, you want to create your own opportunities, it seems to me that it's all about identifying where a problem is for consumers or a problem for some industry and then coming up with a solution. Is that pretty safe? Is that kind of what you and your partner do?

00:13:48 - Matthew Simpson

For sure. And I would take it all the way back to that ad agency I mentioned, the design agency. What happened in the late 90s was we were doing a lot of print, radio, that type of ad, and people started saying, hey, I need a web presence. So even though everybody was on 56k modems and it wasn't really conducive to a great experience, everybody felt like they needed to have something. And so we started doing a lot of websites, and I taught myself how to just do basic HTML, some design, and we started getting into that space. And as it progressed, we found more and more clients. And that's what ultimately transitioned me into getting a lot more into the tech side of things. As I spun off from that design agency into a company with two of my wake forest grad friends that was really focused on simply building software solutions that were web based for anyone that needed them.

00:14:50 - Matthew Simpson

I had met a guy as the ad agency when we were working with a client in Nashville. We were trying to get them as a client. I played golf with him randomly, just had a public course, got paired with him, told him about what we were talking about doing with taking traditional goods and putting them online, and he said, man, that sounds awesome for us.

00:15:12 - Matthew Simpson

We have all these things in our warehouse we'd love to sell. I'll get back with you. Let's do something. And so nothing ever happened there. And fast forward probably a year in advance of that I got hurt, had to have surgery. I'm laying in the hospital pre op with, I'm getting the iv for the anesthesia to go into surgery, and I hear this voice through the curtain next to me and it was completely recognizable as the guy who I had played golf with like a year before. And we started chatting through the curtain and he was like, man, I've been meaning to call you, just hasn't gotten around to it. Please call me after surgery. So we both had our surgeries. After the surgery, I call him, we reconnect.

00:15:58 - Matthew Simpson

It's a big distributor in Nashville. We do a deal to solve their problem, which was taking all of the products they had that they could sell online, building them into a web based business to sell and ship direct out of their warehouse. And so that was the initial impetus to roll off the business from the ad agency, start a new one with two guys, friends of mine from Wake Forest. It was self funding because we did a deal with them to pay for it, to build the site, to build the application.

00:16:28 - Matthew Simpson

And then we built a lot of applications in order to service that, that we could then sell software as a service to other companies. And that company was called six Train Technologies. We began working for another company with another company, shared an office with them in Atlanta called Member Clicks. We merged with member clicks because we were providing all the form builder tools for member clicks. And then member clicks grew and grew. And then we were solving really the association management space software as a service to run a membership, any membership that was out there, and all the forms that are needed for that, and then that ultimately was acquired and I moved on to start pursuing what we're working on today through various failures to get to the point where we are now.

00:17:18 - Matthew Simpson

And I think if I was to look back at a lot of the things that shaped when businesses have been most successful, if you can find someone who has a specific need and go address that need, and that need allows for enough money to be paid to solve it, that's where you really want to focus your efforts.

00:17:41 - Matthew Simpson

Because those businesses have worked best for me versus the ones where I thought I had an idea that someone else needed and I could make something that sounded really cool because we did a really cool product that we launched. It called Path Crosser, that me and Clark, my partner, launched south by Southwest in 2011. It was awesome, but it was basically to show you where you cross paths with people using location data that was check in data from apps like Foursquare and Facebook and some other apps. It was really fun. We had a party with Questlove playing at the south by Southwest. We had lots of hey, this is awesome. Everybody's going to use it. A lot of people download the app. No monetization strategy. It was fun, but didn't really have a business behind it.

00:18:30 - Matthew Simpson

So you learn from those failures, you learn from making mistakes, from trying to follow ideas versus following demand. And over time, I think that one of the things I was afraid of as a younger person was failing all the time. I try and prevent that or try and hide that. And then the encouragement I would give to anybody who's getting started right now is welcome. The first failures, because the second you get those failures, the things that you learn from them can be applied to every single thing you do as you go forward and will definitely give you an advantage and lead to success.

00:19:12 - Bill Risser

Have you done any mentoring for younger guys or girls coming out of college, or have you ever thought about doing that?

00:19:19 - Matthew Simpson

I've thought about it, but I've done a little bit lightly just here and there, but not to the level that I think someday I might consider doing. It's always been that I'm chasing whatever is going on that day with these different businesses, and I haven't had the time and the resources to do it the way that I feel like would be the most useful. I've been on the board of a couple of different companies, tried to help in their initial startup, but nothing more than that.

00:19:53 - Bill Risser

Let's get to the world of real estate. So how does that enter the picture.

00:19:57 - Matthew Simpson

For, you know, that's also a great example of what I just said, which is Clark and I had an idea for Lolo. It was designed to be a rewards app with the mission of local people supporting local independent businesses. It was designed to know after a period of time where there had been a lot of companies that had really come out with discount coupons, half off coupons, a lot of the things that were designed to drive traffic to businesses but not necessarily benefit them wholly.

00:20:33 - Matthew Simpson

It was kind of, hey, here's some people, but we're going to take a lot of this revenue and we thought, can we create something that's more sustainable for local independent businesses that gives them a competitive, not even advantage, but just level the playing field with a lot of the big box stores, the big chains, and a lot of the companies have rolled up companies and have large marketing budgets. How can we help preserve and keep the local vibe alive in each community? Because that's what's so unique. It's like I talked about with Nashville we launched it in Asheville, North Carolina, and there's such a unique local vibe there. And when you go to different communities around the world and you experience their local businesses, that's what makes them unique, that's what makes them special. That's what we want to preserve. And it creates that community feel for both the visitors, but also the people who live there.

00:21:24 - Matthew Simpson

They have something that's special to them. So the initial Lolo app, we went and got local independent businesses to join our program and say that they would kick back some discount into the program. We went to Mastercard, Visa and Amex and got them to. We facilitated where an independent consumer like yourself could put your credit card in Lolo, register it, and then when you spent at these local vendors, you would earn local dollars back. So you would be a loyal local, you would get local dollars in your app. You could then spend that Lodo on any of the rewards that those local businesses made available, like a late and a pastry at a coffee shop, a candle at a boutique, something that was tangible, meaningful, that you could use your dollars, local dollars that you've earned to reward yourself and support the local business, because everything was keeping it within the network.

00:22:26 - Matthew Simpson

It was a great experiment. It was a great experience. We learned a lot. We grew the business, we got a lot of users, but we really, at the end of the day, didn't have a great monetization strategy because we were counting on the local vendors to pay for. And so we know, is this sustainable long term? But again, we had certain points you take a turn, and we had a local brokerage in Asheville, North Carolina, Beverly Hanks, and we had a meeting with them.

00:22:57 - Matthew Simpson

They were doing each month, they're sending out a little something to their sphere. All of the agents were sending an email with a little suggestion of something to do a discount to their sphere of influence, their network of people. But they didn't really like it. It wasn't know. Sometimes the discounts weren't so good. It was something know needed to be improved on.

00:23:22 - Matthew Simpson

And so they asked us, hey, could we just buy some of the things that are in your local network, these rewards? Can you buy the stuff that people can buy with Lodo? Can we buy and then send them out? And so that began the initial discussion for what is now Lolo, which is, how can we help them stay top of mind with an item of value, with something meaningful and local, with a write up, with pictures, just something that monthly goes out in an automated way and keeps them connected with their clients contacts, referral partners, anybody that they want to build their sales network around.

00:23:56 - Matthew Simpson

And so we did an alpha group with Beverly Hanks, honed it, figured out how to send emails, then send text messages, then give them the data that they wanted to see. And they were our first client. We ran that for a year and then began to expand outside of there. We're now in 250 different markets around North America.

00:24:15 - Bill Risser

The actual curating of the local businesses. We've had long conversations, you and I, about that. There's some work to be done there, correct?

00:24:25 - Matthew Simpson

Yes. I would say this has been a business that started as more of a technology business that has really morphed into a curation business with people getting information, connections with the local community, and then being able to provide that at scale to people. But that is our main core competency. I mean, we now have a team of people that curate gifts, and it's an important part of it because the gifts need to be meaningful, they need to be relevant, they need to be at great spots, they need to be local and feel local. And that's the differentiator that we have and that we provide to agents. And it's something that can consistently go out at a very low cost and keep you top of mind and get opened, especially in a time when there's so much noise, so many people sending so many different spam emails. This gives you something that you can support and you have content that you can talk about with all of your sphere of influence.

00:25:27 - Bill Risser

Right? You've talked about this before. I've heard you say this many times to agents who come up to you to talk about Lolo. It doesn't really matter if they redeem it, right? It just doesn't matter because it's the idea that you're sending this to them every month, correct?

00:25:43 - Matthew Simpson

Well, and I would say for the local businesses, we want a certain level of redemption, and luckily we get redemption. But the main goal for the sender, the typical agent speaking in the real estate world, they're looking to have something that keeps them visible, top of mind, every month with anyone that could refer them business or use them again. And there's a lot of options out there that can be costly, time consuming, difficult to execute. We try to create something that is very seamless. They just put their contacts in and then they trust that a thoughtful, meaningful message with a gift is going out from their email, with their branding each month. And so we're trying to take down all those barriers and give them that value. And when people get these gifts in the email and text they open them. They want to see what it is. It's local to them, so it's meaningful. It may be a business they haven't seen before or learned about. They can learn something new about a local independent business. And so the agent is providing inherent value. They're providing information and they're providing a gift each month in an email. And so that creates high engagement. Now they can also take it and redeem it, and that's a large part of what happens. But the first layer of what's the value to the agent is simply that being top of mind. And it's the thought that counts. Someone opens something, they go, oh, wow, that was nice. That was thoughtful. The psychology of receiving something that was given to you creates a very positive response and makes people feel good. And that's really what we deliver.

00:27:23 - Bill Risser

A little dopamine hit. Always good, right?

00:27:26 - Matthew Simpson

Yeah.

00:27:26 - Bill Risser

What's next for lolo? Is there something you're looking at that you can talk? Know, sometimes I ask this question and people, you know, we're doing some things.

00:27:35 - Matthew Simpson

Well, I think know a lot of the things that people that are in the industry know that we're going to be doing. So it's not really so much a surprise, but it's just making every bit of this more accessible via a lot of other products. So that whether you use a CRM of some type, whether you're building your own application, whether you're using social channels and you want to integrate some component of what we do to automate, adding people to your list and sending gifts, I think our next vision is mainly just making this more and more accessible and making the feedback loops better so that you learn, hey, when I put someone in, this is what happened. This is how many times they opened it, this is when they redeemed it. Then I can be more educated in how I trigger new gifts or new messaging or new calls. Just understanding your network of people, if you're in sales, understanding when they're more likely to buy, makes it more fertile ground for you to make your outreach. So everything that we're doing is going to be designed to help all the software that's out there and the AI buzwords that are going on, all the tools that are designed to try and create more and more relevant content, we're going to try and plug in everywhere that we can to make that better. And then I think parts of that will also be allowing different cadence descending of gifts, maybe different types of gifts, maybe different things around that, but it'll always revolve around staying with our mission of supporting locally owned independent businesses and providing tools to make sure they have a level playing field with all the big box stores and big brands.

00:29:23 - Bill Risser

I'm watching the clock here. I'm going to go ahead and give you the final question here. Now, you're not a realtor. I don't think you've really had any experience in that side of the place, but you've been around them for a long time now. And so in your opinion, what one piece of advice would you give a new agent? Just getting started.

00:29:42 - Matthew Simpson

Well, I'm going to be biased in this because my knowledge is really around sales. And when you're thinking about long term sales cycles that have large ticket items that are infrequent purchases, I would say focus on relationships, focus on your network. And from day one as a new agent, do not be afraid to reach out and begin building your sphere of influence. I think the thing I see mostly with any sales job is that people will allow fear to take over and prevent them from doing something. Fear of rejection when they make a phone call, fear of failure when they go to an appointment. And at the end of the day, each one of those failures, like I said earlier, is so valuable. If I look back and think about had I prevented myself from failing at something, would it have been an improvement in my career? And I would say absolutely not. In fact, I wish I had failed faster. And the faster I fail more I learn about what I need to do to succeed. And the only way I can think to tell a new agent to get started is focus on relationships. Because over know if they really want to be in it for a long haul. They've got to start with making those relationships, proving they can do something and then working referrals from there because I believe that's the best way to build a long term foundation for the business.

00:31:25 - Bill Risser

That's awesome. Matthew, if somebody wants to reach out to you, what's the best way for them to get in touch with you or with Lolo?

00:31:32 - Matthew Simpson

I would say go to joinlo.com. Anybody can always email me at matthew@joinlo.com.

00:31:39 - Bill Risser

This has been great. I knew I would get some things out of there that I hadn't heard before, which is very cool. I really love what you're doing. I've talked to a lot of different people about what you're doing and said you got to call these people. You got to understand how affordable and powerful this tool could be. I think you've done fantastic work. So congratulations on that and thanks so much for your time today.

00:32:03 - Matthew Simpson

Thanks for having me. Enjoy at it.

00:32:05 - Bill Risser

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