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    Matt Silk lived the entrepreneur's dream: he hustled and built his startup in San Francisco, scaled it, and sold it. He moved to Austin and took his entrepreneur experience and used it to start angel investing and real estate investing locally. Here's how he did it and what he looks for in his investments.




    Thomas: So today I'm excited to have Matt Silk on the show. Matt has been a longtime customer, advocate, and advisor to Rocket Dollar. Matt has an incredibly interesting story has been a successful tech entrepreneur, who sold his business just over two years ago, and has now made the transition to a real estate fund manager and angel investor. Matt, thanks so much for being on the show. I'm excited to have you here. Every time you come on and you do webinars with us, and you've given us some great testimonials, and done some great video work. I'm excited to have you here for the podcast now.Matt, there's a ton I want to touch on. But let's take it back to the very beginning. Tell us a little bit about how your career began, how you got into entrepreneurship, and what led you to the business that you ultimately sold.

    Matt Silk: So I grew up in an entrepreneurial family, and I knew in the back of my mind that I'd always start my own company. I didn't know what that company was going to be and after college, went out to California, got a couple of jobs in the tech industry to get some experience, and then a buddy of mine and I started talking in 2004/2005. And we saw an opportunity in marketing technology that we thought was a natural progression, whereas everyone was taking email marketing in-house. Mobile communications didn't seem to have a real plan, and we were very early hindsight 20/20. We were very early in the mobile messaging industry. But our hypothesis back in 2004/2005, was there's going to be an online tool, to help you build a list and talk to your customers over the mobile channel. And we started with SMS, that was the workhorse back then. It was the only option to communicate over the mobile channel. But that's what we started with.

    So our original hypothesis was, you need to talk to your customers and build a mobile engagement channel, and we started with that. And over 12 years, our passion project turned into a real company, and we ended up building several different channels. After SMS there was MMS, and Wallet, and Push, and Beacons, and all different confusing technologies to the marketer, that we tried to make unconfused, and make it easy, and a self-service platform with a great services team, to help them optimize that channel and figure out, how do I engage with my customers over this great new supercomputer, that you're walking around with, in your pocket?

    Thomas: Well, and that's amazing. I think it's very rare for entrepreneurs to be one of one, right? Even though you started in 2004/2005 like you just mentioned, for you guys to have gone 10 or 12 years with the same project, and been successful is pretty outstanding. I think nowadays you hear about entrepreneurs that start a company, and then two years if it's not going exactly the way they want it to go, they switch to something else, and then they switch to something else. But how did you hang on, or go through the pain for 10 or 12 years? And when did you know that you had a real business, that was going to be successful?

    Matt Silk: So luckily, as you say, and it's probably not luck, it's more just grinding it out over the years, our original hypothesis was still valid from the day we started to the day we finished. But we never had a pivot, but we had some narrowing. So in the beginning, we knew customers or businesses are going to want to communicate with their customers. But we didn't know the exact business model. We didn't know if this was going to be a consumer play, a business play. So there were a lot of things that got refined over that 12-year process. One of the first major tipping points for us that we had to figure out is, can we be on the consumer side or the business side, or can we play both?

    We started the company in San Francisco. Right around the corner from us, was a little company called Twitter. They focused on the consumer side. So at one point at our early days, we had some ideas that we'd have a consumer destination, where you'd buy your keyword, like your name on shared short code, and you'd set up your list, and you'd go to a website and you'd find caller list. It's essentially what Twitter did, and they took it in a different direction, but not that much difference in the days when it was just mobile messaging over a shortcode.

    So at one point, we sat down with the company, and we looked at our funding strategy, and we talked to the company about, where do we want to go? What do we want to do? And we kind of mapped out a world where we focus on the consumer side, we focus on the business side, or we tried to do both and the company as a whole made a decision. We wanted to be a business service. We were going to build an enterprise set of tools because we thought that was a better strategy to build a business, that we knew we could grow at X percent per year, get X number of customers, charged X number of dollars, and build a smart business. So we decided on that.

    Then I'd say the next thing that we figured out over time is, what price point do you want to play in? So as the company grew we tried to figure out, what price points made sense? Do we want to focus on an SMB customer? Did we want to focus on a local business? Did we want to focus on a mid-market? Or did we want to go after those enterprise larger deals? We had to figure that out, and we ended up deciding to focus on the enterprise side. And then even further, we had to narrow things and figure out within that enterprise sale, which segments we want to go after because we couldn't be experts in everything. Over time, we had enough retail customers that we knew that was a segment. There was a natural place to build a massive list and communicate at scale with your customers.

    Then the other big segment that we went after was restaurants. So it ended up being, once we were a mature company, that there are two main segments. Because we were a platform play, we could work with anyone in any segment. So we weren't confined to only talking to those segments. But from a BD and marketing standpoint, we had to pick our battles and become experts. Because I, myself, I was the BD team. So I was going out to conferences, and I couldn't be on the road every single day. I had to pick which conferences because conferences are expensive.

    You're going after the enterprise, you got to spend money, you got to sponsor shows, you got to get up on stage and look like the thought leader and the expert. So I can only be the expert in so many different segments. So once we were mature, it was really like two segments. So that's how ... Even though it seems like we were incredibly focused from day one, it was at a very high level that we were focused, things narrowed and over 12 years, we kind of found our way.

    Thomas: Because I think that every startup and every young company goes through that, how much of that finding your way was you reacting to what the market was telling you, versus you building the company that you wanted or sort of channeling your expertise, and your experience, and your vision?

    Matt Silk: I mean, there was probably a little bit of both. I don't think there was a very clear, like, "We're going to hit this milestone, and then we're going to make this decision point." I'd say most of those decision points that I just went through, or the market telling us, or our funding telling us we had to figure out something new, or we had to tweak and focus. So it was probably pretty organic, and we're probably a pretty unique story that we were a 12-year-old startup. I mean, at scale, we grew the company to $12 million in revenue. We were 35 people. So we still felt like a startup, we tried to keep that culture.

    So most of those learnings along the way, were probably organic with, there was a vision of what we wanted to do which never changed if we want to help people connect with their customers and engage over the mobile channel, but the rest of the stuff we learned over time, and we made a ton of mistakes, hindsight is 20/20, we tried all different segments. But we slowly figured out what segments we want to play, and what price points made sense. How do we serve these customers, while we're also dealing with all the external factors that we can't control, about new technology that comes into the space, lawsuits, changes in government, communications, class action lawsuits? I mentioned any number of things that came out of that field, that we had to evaluate and figure out, how does this affect our strategy and what we're doing?

    Thomas: Right. Yeah, and it's so interesting for us too at Rocket Dollar, it's you can control what you can control, but then there's what you can't control and then there's what you don't know, right? And so, it's a lot that you don't have power over, but you can just do your best to prepare for different things. I want to hit on two things. One is culture and how you built culture, and what kind of culture you guys had. And the other is mistakes. But let's talk about culture first. When you were building your team, what were you looking for? And what was important to you in the team that you were building, and the culture that you guys had? And how seriously did you take culture?

    Matt Silk: I mean, I think it's critical. The most important thing you can do at a young company when you're in startup mode is to find good people. Because there's a lot of great ideas out there, there's a lot of great markets, there's a lot of bad markets, but finding people who are in it to win it with you that you trust, and you want to work with, and you want to be around, is the key to success. So in the early days, we were generally recruiting people that we knew from other jobs. Some of the first people that came aboard, were people who worked with me at E-Trade.

    I went and grabbed an engineer that I liked. I grabbed my product guy from my team. I grabbed a designer that I knew. So I would say the first wave of people were all kind of insiders, that knew about the company before we were starting, that we're involved in those coffee shop meetings, and trying to figure out is this a real idea or not? After that, the next wave of hires, we did start posting job descriptions, but most of the people we found over time from our network. So the bulk of the people was working our networks and not posting job descriptions, not talking to recruiters. Because we were a pretty small team, it wasn't all that hard to fill the positions within our network. So I think people are probably the most important thing that has to do with culture.

    Probably the next thing is just having a shared vision, and helping people understand, what are you trying to do? And why are we trying to do it? So making sure your employees understand, why did the company start? What are we trying to accomplish? Where do we want to be? And kind of laying out those goals for people is really important because you want them to feel like they're a part of something bigger. Comp drives behavior, so you have to make sure your comp programs are set up for success. But people have to believe in the vision. If people don't believe in what they're doing, then it's just a job.

    So as much as you can do to convince people that they're joining something bigger than just a job, and finding those people that believe in what you're doing, and they're excited about what they're doing, whether it's because they're working with their buddies that they always wanted to build something with, or they're working on a mission of building this technology platform. I think you have to find something about the job, something about the people, that makes it bigger than a job. If you can do that, the rest of the word culture is pretty easy. It's not just about having beer and coffee in the office and having a happy hour, it's about being with people you want to hang out with and want to spend time. Because, when it gets tough and you have to work till 2:00 in the morning to fix that bug or get that extra feature in to close that big deal, you need to be in the trenches with people that you want to be in the trenches with.
    Thomas: Right. Yeah, and I think that's something that we've also been very lucky at Rocket Dollar is that our networks, just being in Austin, we're big enough to be able to pull together a really good team. I think we're 18 now.

    It also helps that Henry is practically the mayor of Austin.

    Thomas: Right. Yeah. He and Josh Bear are probably like the two tech mayors. There are a few notable ones, but it's amazing how many people that man knows. The other thing that I wanted to ask you about is, tell us a little bit about some of the mistakes that you guys made along the way. I mean, everybody's sort of sees the end product and it's a successful exit, but tell us about some of the mistakes that you couldn't have seen or that looking back, you're like, "I can't believe that that happened, or we did that," and what you learned from it, and how you sort of moved forward.

    Matt Silk: I mean, I'd say our biggest challenge over the years was our financing strategy. I think in the beginning, we tried not to take a ton of VC dollars, we tried to bootstrap it, and we tried to keep as much equity in-house as we could for the employees, for the founders. But it was certainly a challenge that, if you don't have a solid fundraising strategy and you're not capitalized properly, it can be really difficult to do things. I'm saying something fairly obvious, but when you're in the grind, when you're building the company, sometimes those things don't always work out well. The market may not be supporting you, or you might not have thought through everything that you need to because you also don't know a lot of the things that you didn't know.

    In 2005, I knew nothing compared to what I knew in 2012 when we hit our stride, and we were just focusing on scaling the company. That was a long time and a lot of learnings, and financing along the way. So that's probably the biggest thing that I think we did wrong. I don't know that we could have done it differently, but in looking back, when I sit down with some of the entrepreneurs that I'm working with and doing some angel investments, I try to think through, what is our funding strategy, and at least put together a clear plan to say, "We're going to raise this much to get to this milestone. Then we're going to do this, then we're going to do that." And try to think through what is the three to five-year plan, so at least we have a blueprint that we're working towards. I don't think we had a very clear blueprint, and we were probably young, dumb entrepreneurs, who believed that "We can get money. We can do whatever we need to do when we need to do it."

    So I'm a lot more methodical in my angel investing now when I sit down with investors ... I mean, when I sit down with entrepreneurs and try to get them focused on, "Where are you going to be, and how are you going to get there?" Everyone says, "Oh, I want to raise my series A. I want to do this, I want to do that." But it's like, "Okay, what do you need to do to get there? What is the ARR milestone you have to hit? What is the number of locations that you need to hit? What is the number of consumers you need to hit?" So really asking those tough questions, because of the pain that I went through, I'm pretty well equipped to ask those questions, and help that early-stage entrepreneur at least have a better blueprint of, how do I get to success?

    Thomas: Right. Having those metrics and having those milestones that you need to hit to raise that round that you want can also provide some clarity that maybe you didn't have before. And so they're not bad things. They might be tough questions because it might make you question your business model or your idea or your market fit, but having that clarity also allows you to work towards something very tangible, very clear, which I think is valuable. I've got one more question about Waterfall, which was the name of your company? When did you decide that to sell, was it totally out of left field, or did you know that you were ready to exit and move on? Talk to me a little bit about how that process went down.

    Matt Silk: Yeah. I would say our first five or so years, we were surviving. We were finding enough customers, finding enough money to get through some challenges. I mean, we had to live through social media marketing, we had to live through the mobile app craze before we had a seat at the table, and marketers were allocating budget to mobile, nevermind mobile messages, mobile in general. So the first five years, the first half of our life, was really difficult. We stayed lean and mean, we still stayed on point, but that was challenging. Then we had the next wave where we finally had a seat at the table. We didn't have to convince people that mobile was a thing that they needed to invest in, we needed to just fight for our share of the mobile budget. So we kind of had our next phase from 2010 on.

    At that point, a couple of years into that I recall around 2012, we knew we needed to scale and grow. That's where we started to run into some challenges that, it was almost like what we were doing, it wasn't sexy and cool anymore. Because it had been so many years, there were so many new, flashy, cool technologies within the mobile space. So I don't want to say we weren't investable at that point, but it was a much tougher investment conversation with the VC market. So we were at a crossroads of, how do we grow and scale and do what we want to do, now that we have a solid business, we've learned everything, we've made all the mistakes that we can make, but we're also not sexy and cool anymore?

    So we thought, looking at some of our competitors and getting to scale, growing inorganically rather than organically, was probably our best strategy. We ended up buying two of our competitors, smaller deals, they were a little bit distressed, and we grew the company that way. Once we had done that, and we had integrated them into our platform, into our culture, into our plan, we thought, "Okay, this makes a lot of sense. There are enough companies out there that have half a million thousand customers, a small basis that we can probably go acquire, that we can grow the company. While we are still growing organically, growing inorganically doing M&A, basically a roll-up strategy within our space makes a lot of sense."

    So instead of going out and raising another venture round, we started talking to venture debt guys, or growth equity guys, about raising a round to go acquire a bunch of customers, because we had to get to real scale and had to grow the company. Because even we got the company to 12 million in revenue, that's still a rounding error in the marketing tech stack, so we knew we had to get to scale one way or another. Otherwise, this is a lifestyle business. We had already raised venture money, so it couldn't be a lifestyle business. So we had to grow and scale.

    When we started talking to later stage guys about the roll-up strategy, we weren't all that excited about some of the offers that we got to get that war chest, to go out and buy a lot more companies. So we either had to figure out how to get comfortable with those multiples that we were getting, or we needed to push into someone else's roll-up strategy. We ended up getting a good offer from someone who'd already bought two companies in our space to be a part of their story. In our hearts, we knew that we were just not a big enough piece of the marketing tech consideration, that we either needed to get to scale on our own, or needed to be part of someone else's scale story.

    So we ended up selling. I'd say we very seriously started switching gears is probably beginning of 2017 from, "Let's go raise our war chest," to, "Maybe we should consider being part of someone else's roll-up strategy." We ended up consummating that deal in July of 2017. So we sold to a company coincidentally here in Austin. I had moved to Austin in 2010 to grow and scale the company, and it just coincidentally worked out that a player called Upland Software here in town had bought two companies in our space, they made us a nice offer, and we did the deal in July of '17.

    Thomas: Very cool. That went pretty fast from when you guys decided to, from amassing your war chest and pursuing the strategy that ultimately got you acquired in someone else's story-

    Matt Silk: We may have had some of those conversations along the way.

    Thomas: Right. For sure. I mean, no decision is made that quickly. I'm sure you guys were talking about it for a while. Tell me about what happened after the acquisition. Did you stay on? Did you exit? Tell me a little bit about what happened then.

    Matt Silk: Yeah. I stuck around for about six months, and then I consulted for a little while after that. Upland is a great company, they're doing great things, but it wasn't for me. I'm still entrepreneurial at heart. I still wanted to do things on my own. So once I had helped transition the business over, we parted ways on good terms. And then I started focusing on what I wanted to do when I grew up. So I mean, that's really how we got to today where I've been splitting my time between building a real estate investment fund and doing angel investments. So I kind of took my barbell strategy of asset allocation, and I have my very safe real estate investments. And then I have my swinging for the fences on my angel investing and early-stage tech investing, That's what I've been doing for the last couple years, and I'm having the time of my life, and trying to figure out if I can do this for the next 20 years as my job.

    Thomas: We'll hit on both of those points, but let's start with real estate. So you exited, and how did you know that you wanted to be a real estate investor, and why real estate specifically?

    Matt Silk: So I had been in Austin for 10 years as a cash strapped entrepreneur, and I'd seen so much happen in Austin, all of these flipping shows that you see on HDTV, like I was here, during the heyday when those were just starting. I mean, now they're crazy. You can't turn on the TV without seeing a flipping show now. But that was just kind of getting going. Austin was a hotbed amongst a few other communities around the US where that activity was happening and hustling and bustling, and the Austin real estate market has grown significantly over the last 12 years. There's a long debate as to what's going to happen for the next 10 years.

    But I had seen that, and so many people I knew were part of that real estate growth and explosion, whether it was flippers, or agents, or investors. So I knew real estate was something that I wanted to do, within real estate, I didn't know what exactly I wanted to do. So I tried a few different things and looked at a bunch of different strategies, and I ended up going with building a small real estate fund to invest in single family homes and condos, because I wanted that safe place to park my money. So it was really amongst that part of that asset allocation strategy. I knew I wanted to be really aggressive on the angel side, and we will talk about that in a minute, but high risk, high reward on the angel investment. So I wanted something to balance that out by being very safe.

    And so we landed on single family homes and condos. We decided to focus on the Austin area because we fundamentally believed that Austin was going to continue growing for many, many years. I started talking to friends, colleagues, past investors, about what I wanted to do with my personal money. It wasn't as much about like building a fund. I don't think I set out in 2017 or 2018 to start a fund. I basically said, "I want to invest the money that I was able to take off the table." A bunch of people said, "Oh, we want to ride along." So I ended up just organically morphing into, "Oh, well, why don't I start a small fund?" So my first fund was a couple million dollars. We bought eight properties. We'll call that the proof of concept. So we deployed that in 2018.

    We were buying in all different places, buying from wholesalers, buying off of MLS. We were generally renovating those properties. So I was competing with the flippers on the buy side. But we decided to do a long term buy and hold strategy. So we were basically renovating them and holding them in our portfolio, and the way we structured the fund, it's a long term buy and hold strategy. So my investors are basically parking some money. Instead of putting it into an index fund or a mutual fund, they're parking some money in real estate here in Austin, and I am their fund manager. Once a quarter, I give them an update on what's going on which nothing's really going on other than we collected rent, we spent a little bit on maintenance. So it's a real set it and forget it strategy of single family homes, condos in the Austin area, that you're going to forget about for 10 years, call it. And then we'll figure out, are we ready to sell or do we want to keep this going for another five or 10 years?

    Thomas: Right. And now, this year in June, I think you mentioned earlier before we started recording, you closed on your second fund.

    Matt Silk: Mm-hmm

    Thomas: And same strategy?

    Matt Silk: Decided to do the same strategy. We decided that the Austin market is still growing significantly as more and more people come from California like myself, the cliché, the California tech company that came to Austin. That keeps happening every day. So we fundamentally, even though the market has grown for the last 12 years, we think there's a lot of growth left. And yeah, there could be a pullback, there could be a correction, but we think Austin is, I don't won't to say recession proof but, it's not going to be hit as bad as some other cities. It could have a 10% correction a 15% correction, but in two years, we think it's going to recover and keep going. Because it's still such a great place to grow and scale your tech company. To me, that's the biggest driver.

    We think Austin is going to continue to grow. So we decided for our next fund we're going to continue doing the exact same thing that we're doing, and we're going to do it a little bit bigger. So the second fund, we raised $5 million in equity, we layered debt on top of that, so we were going to stick with single family homes and condos, starter homes in the 200 to 250 is our primary target. So it'll be 20 homes in equity and then we'll layer on another 10 to 20 homes in debt after the fact on the portfolio.

    Thomas: So you guys are going to have 30 to 35 homes in your portfolio. Do you guys have a property management company that you contract or do you guys do it in-house? Or how do you manage that many properties?

    Matt Silk: So my wife and I started the company together. She is a real estate agent, and she's also doing the property management for our book of business. So we're not managing properties for other portfolios. So we're not advertising property management, but right now we're doing the property management in-house. A year from now, two years from now, I don't know if we'll continue to do that in-house, but right now we're doing basically everything in-house. So we're basically this a private read for our investors. I tell people like, "Think of this as real estate in a box. I'm your fund manager. I am your investor relations. I am your finance and accounting. My wife is our agents and our property management company. So you know who's touching everything to do with this transaction."

    A couple of years from now, like I said, we'll probably look at every piece of this and decide what do we want to keep in-house? What makes sense for us personally? But, we're building this thing for scale. But we're not really sure how much we're going to scale it, we'll kind of take it milestone by milestone. But right now we're laser focused and building fund two, which is going to be 30 to 40 properties.

    Thomas: Have you guys even started considering what fund three might look like?

    Matt Silk: Not really. We started aggressively buying in July. We're already 10 homes into that buying side. So right now we're juggling more than enough. Because we tend to buy three or four homes at a time, get them renovated, get them on the market, get them rented out, and then we kind of do the next batch. So we're 10 in for the next year, so we probably have our hands full. Somewhere along the way, I'll start thinking about what's next. So unsure yet if we'll stick with the exact same strategy and do it again with another Toronto Capital, or if we'll try something else, or maybe I shift gears and focus more on the tech investment side. We'll see. So right now we're focused on that, and we'll see what's next six months from now.

    Thomas: Yeah. Well, I'm excited. I mean, we'll be here so I'm excited to see what that looks like. And let's shift a little bit to the angel investing side. I mean, obviously, a lot of entrepreneurs exit their companies and immediately want to get on the other side of the table, and want to be angel investors because as entrepreneurs, we've seen how angel investing can impact your portfolio. What segment specifically did you look for when you started angel investing? I mean, obviously, Rocket Dollar is more of a fintech play, but your background is more in the marketing software world. What specific industry or what do you look for in angel investments?

    Matt Silk: Yeah. So I actually came from the fintech world before I got into marketing technology. So I have a good number of years at E-Trade, six years on the brokerage product management team. So I'm a product guy at heart. That's really my background coming from fintech. That's where I say I cut my teeth. Six years at E-Trade felt like a 30 year career in fintech. So I had a lot of expertise on SAS software, fintech. And then obviously, we started the company in marketing technology, so built up that expertise. And then within the marketing technology world, the two segments that we really focused on were retail tech and restaurant tech. So those are probably the three segments that I feel most comfortable evaluating a deal. So I tend to look for deals and spaces that I know and can understand, and can add value. Because I'm not dealing with a billion dollar investment fund, I have to decide where I want to place my bets, where I want to put money to work.

    I'd say even more importantly, where do I want to spend my time? I mean, I look at my angel investing, because right now I'm investing on my own book, I'm not doing it as a fund. My time is probably my biggest limiting factor because I can only make so many investments, and I look at my angel investments as my job without having a job. I get to work as hard as I want to work for those entrepreneurs, and help them work on this stuff. But at the end of the day, it's their company to drive. I'm an advisor, an investor, or a board member, whatever it may be, but I can only do that with so many companies at a given time. So I evaluate deals as they come. I try to find spaces that I'm going to enjoy and I can add some value, and I'm going to have some fun, because I'm trying to avoid getting a job. If I can do that, it would be great.

    Thomas: Right. Well, and we know ... I mean, what you said is absolutely true in our case, as one of our first angel investors at Rocket Dollar. I love that I can just text you or call you, or send you an email, and I've got a response in a few minutes, and you've done some wonderful things for us. We really appreciate it and I'm sure all of your companies in your portfolio, appreciate it as well.

    Matt Silk: Glad I can help, any time.

    Thomas: Apart from Rocket Dollar, what is your most exciting investment that you've made, that you think has a lot of potential?

    Matt Silk: So I was kind of walking you through some of the segments that I've been focused on, but then all of a sudden, I became a real estate investor. So then I had a new segment that I got to play in, which is now called proptech, property tech. So the real estate world has been really, as it explodes on the investment side, you also have so many different, really interesting plays in the technology supporting the real estate growth side. And I think over the next five to 10 years, you're going to see some incredible consolidation, disintermediation, fragmentation that's going to be fixed. Because there's so many pieces of the real estate transaction, but there's an absolute mess today, that is really hard on everybody involved, on the consumer, on the buyer, the seller, the lender, the appraiser, you name it.

    There's a company coming up that's gotten funded in the last two or three years, to try to fix every one of those pieces, and there's so many different strategies that play. You have iBuyers coming in. So how are iBuyers going to compete with the regular market? And how are Joe consumer, who wants to buy his house that has a contingent offer because he's got to sell his house, competing against the iBuyers? There's companies that are trying to solve that problem. So proptech is a new one that I can add to the list. So I have four segments that I'm looking at.

    So given my breath, and I'm sure a month from now, I'll have a new segment that I'm thinking about because I'll see a good deal that I just like, and I can be opportunistic because I'm deciding on my own what I want to invest in ... So now I forget what the question was.

    Thomas: What you are excited about?

    Matt Silk: Yeah. So I'd say right now, the two companies that I'm probably most excited about, I have a company in the restaurant tech space called One Dine, that I invested in their angel rounds. They spun out of a restaurant technology or analytics play called Marketing Vitals. They're up in Dallas. They are solving the problem of tableside ordering and payment, and I think they have a really interesting way that they're attacking it, where they're not forcing a company to rip out their existing POS, which is ... Restaurants, especially on the larger side with multiple locations have so much invested, and it's a multi million dollar project to change that POS.

    So these guys are layering on top of the POS, and bringing all of these great new tools to help that server, or help the consumer directly engage and place their order, and make the payments and really speed along that transaction. So I'm really excited about that. There's a number of competitors brewing, but I think these guys have a really good head start on the market, because they came out of the restaurant space. They're very close with the restaurant analytics company that they spun out of, so I think they're going to do great things. So I'm excited about One Dine in the restaurant space. And then I'll mention one other on the real estate side.

    One of the companies that I very recently invested in, real early stage company called Likely.AI. What Likely.AI is doing, is they are crunching all the data in the real estate industry, and trying to predict when a house is going to list for sale. So they are selling into at agent's teams, brokers and also the lender side, and trying to narrow down in any given county, out of that hundreds of thousands of potential homes, instead of trying to talk to 100,000 people and convince them, "Hey, it's time to refire, it's time to get alone, or it's time to list your house," they're trying to narrow down by predicting which houses are likely sellers.

    So the lead generation industry is always a challenging one. There's always someone playing, but I think these guys have really added a technology layer to it, and they're adding a lot of value and helping either the lending side or the agents, now they're focusing really, instead of arming you with a machine gun, or arming you with a sniper rifle and giving you specific targets. So I'm excited to see what they do over the next couple years.

    Thomas: Yeah, and that's fascinating on the real estate tech side. What did you call it? Prodtech?

    Matt Silk: Proptech.

    Thomas: Proptech. Okay, got it. Yeah, because I mean, even on Instagram, I get advertised because I'm on real estate websites all the time. Because of what we do at Rocket Dollar, I get advertised portfolio management, property management, the Airbnb. There are so many strategies for real estate that are from the investing side, from the management side, from the sheer amount of paperwork that's happening. I think it's a really exciting space for everyone, whatever side of the coin you're on, and for a lot of our customers that are real estate investors.

    Thomas: I think that ... I mean, we don't even need to plug Rocket Dollar right now, but for our customers that are investing heavily in real estate, and managing properties, and flipping, and rehabbing, this is all really exciting stuff because real estate for a long time has been kind of an old boys club, that deals were done over steak and bottle of wine, and it was hard to break in. And now with all these disruptors, it's going to make it easier for everybody to participate. I think that's really exciting.

    But Matt, is there anything else that we need to hit on today? What else should we share, that you think would be exciting, that you think our listeners would be interested in? Any parting pieces of advice? And how can people get in touch with you if they want to?
    Matt Silk: Yeah, so TMW Capital, Thomas, Mary, William, capital.com, is my website. If you hit that contact us form it's going to come to me, because the company is very small. But yeah, I'd love to chat with anyone that is either in the real estate space and looking to invest, or if you have an interesting technology, and think I might be able to add some value as an investor or advisor, happy to chat anytime. I don't think about that as a job. I just enjoy having those conversations with entrepreneurs. So I do it probably three or four times a day and that keeps me going. So feel free to reach out to me directly at tmwcapital.com.

    In terms of parting gifts or parting thoughts, I would just say to entrepreneurs that are out there, figure out where you want to be and map out that blueprint on how to get there. You're not going to know everything, you're not going to have everything. Figure it out and life is going to come at you, and throw 100 hurdles in your way. But if you're serious about getting your company off the ground, just map out a plan and do your best to hit those milestones, and really chop down those hurdles as they come in front of you.

    On the real estate side, it's going to be an interesting ride over the next few years. Because like I said, there's that new category proptech that's really ... That term I don't think has been around for too long. I think that's the last couple years. But there's an incubator in New York focused on just proptech. There's a bunch of funds out there that have made five or 10 investments, that I've seen in Silicon Valley. There's a fund here at Live Oak, that's made a couple big investments in the real estate space. So I think you're going to see so much hustle and bustle, and activity in real estate and proptech, to really open up the market to a much broader base. As you're saying, it's no longer the old boys club. There are ways for someone to get involved in commercial real estate, in residential real estate, in funds, in the tools around it. So it's going to be an interesting fun ride over the next few years.

    Thomas: Fantastic. Well, Matt, thanks again for being here, and we'll talk soon again.

    Matt Silk: Sounds good. Thank you Thomas.

    Topics: Real Estate, startups, podcast

    Published on December 18 2019