Venture Everywhere Podcast: Jennifer Mason with Anthony Dedousis
Anthony Dedousis, Founder and CEO of Revival Homes, catches up with Jennifer Mason, co-founder and CEO of TitleWise on episode 30: Riding the Title Wave.
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Episode 30 of Venture Everywhere is hosted by Anthony Dedousis, Founder and CEO of Revival Homes, a platform for homeowners building accessory dwelling units (ADUs), providing both marketplace services and lending options. Anthony chats with Jennifer Mason, Co-Founder and CEO of TitleWise, a digital platform designed for title abstractors. TitleWise's all-in-one platform streamlines workflows and automates traditional real estate title research tasks, boosting both speed and accuracy while reducing redundancy and costs. Anthony and Jennifer discuss the use of technology in modernizing title research and the real estate industry overall.
In this episode, you will hear:
How title insurance plays a crucial role in real estate transactions.
TitleWise's approach for integrating in-house and outsourced talent while upholding a robust company culture.
TitleWise’s transition from traditional methods and the importance of supporting title researchers while maintaining a human-centric approach in technology.
The challenges of aggregating public county records and dealing with diverse databases.
The value of having flexible tools for both online and on-site courthouse research.
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TRANSCRIPT
00:00:00 Jenny: Hi and welcome to the Everywhere podcast. We're a global community of founders and operators who've come together to support the next generation of builders. So the premise of the podcast is just that, founders interviewing other founders about the trials and tribulations of building a company. Hope you enjoy the episode.
00:00:21 Anthony: Hi, and welcome to Venture Everywhere, a podcast exploring the trials and tribulations of building a startup from zero to one. I'm your guest host today, Anthony Dedousis, and I'm founder and CEO of Revival Homes, a construction marketplace and lending platform for homeowners building accessory dwelling units.
00:00:41 Anthony: My guest today is Jennifer Mason, the founder of TitleWise, a company developing software designed for real estate title research services. Jennifer, welcome.
00:00:51 Jennifer: How is it going? I am so happy to be here.
00:00:54 Anthony: Doing great, Jennifer. Really glad to be talking to you. First thing on my mind, what is title and why do people buy title insurance? I mean, I vaguely know it is a real estate related thing, but explain it to me like I'm a five-year-old.
00:01:10 Jennifer: You know, it's an important question because a lot of people don't fully understand title and title insurance until they have a problem and they're forced to know what it is. But real estate title research and insurance impacts nearly every real estate transaction.
00:01:25 Jennifer: So if you're a homeowner or going to be a future homeowner, it is an important part of that transaction. So with title research, you have abstractors who use public land records to create reports for banks and settlement companies that compiles information like who owns the property, are the taxes paid.
00:01:45 Jennifer: And do other parties have interests by way of mortgages, liens, other agreements? We put all that information together so that the settlement company has that context as they prepare the deal for closing.
00:01:58 Anthony: Got it. So now where does TitleWise come in? Why is software for real estate title research services needed in this market?
00:02:06 Jennifer: Title research is a very special corner of the title and real estate industry because there is not really.. a few exceptions, there's really not a traditional title college degree or professional track that gets you the experience you often need. So you see a lot of experience in title research where it's family-owned companies.
00:02:29 Jennifer: My own title company is a third-generation firm founded in 1948. We regularly talk to potential customers who have 100-year-old companies. So it's an apprenticeship model that means that technology has maybe been stymied or not fully embraced because the people doing the work have done it the same way for a long time.
00:02:53 Jennifer: They are the boots on the ground when it comes to accessing those local records at their local and county courthouse. So when you have all that tradition built into this very important work model, sometimes adoption for change and new operations is slow to happen.
00:03:10 Jennifer: But whereas we're noticing that the entire real estate industry is becoming more technologically advanced, it is really important for this corner of our work to start taking a look at how can software tools keep us relevant and competitive in a changing market.
00:03:25 Anthony: Now that's interesting. You mentioned that your title company is a third generation business. I'd love to know more about that. Tell me how you became a title expert.
00:03:34 Jennifer: It is fun, but also classic, title story. So my husband, partner, co-founder, we actually met at work. We were title researchers for different companies, but we worked out of the same counties. So title researchers often spend the day in the courthouse with their competitors, but they're also your colleagues.
00:03:53 Jennifer: His company was Southern Indiana Abstract Company. His grandfather founded it in the '40s. His father served as the attorney, and now he's working as president. When I, after we got married, joined the company, we started to take a look at how these traditions were kind of impacting the way we were relating with our clients.
00:04:14 Jennifer: So we were still doing some handwritten worksheets. We had PDF files that were only saved by property address. We started to realize that even though we were considering ourselves modern title researchers, we still actually had a lot of the old school stuff that looked a lot like it did back in 1948.
00:04:33 Jennifer: And that's where we really kind of started to take a look at how does technology play out in a modern title company.
00:04:39 Anthony: So then where did you, I guess, evolve from doing title research in a traditional way towards having that kind of aha moment of, gee, maybe there's a software solution to be found here.
00:04:52 Jennifer: It started, I guess like a lot of ideas in our garage. We were talking about, oh, wouldn't it be nice if there was a way where we could, instead of writing this up and having to type it up later, could just do everything in one step, put our copies on the cloud, access our prior files from anywhere. And we just kind of started to sketch it out.
00:05:11 Jennifer: We found a local developer here in our Louisville area. We're based in Southern Indiana, close to the Louisville, Kentucky market. So we were able to find a software startup that could help us get that original vision brought to life. But it really was designed just for us and our clients. We launched TitleWise at our title company in 2019.
00:05:32 Jennifer: And just a year later, the pandemic hit, that real estate boom happened, and we were able to handle all of that increase in volume without any new hiring or outsourcing. And that's where we really started to take a look at how something that seemed kind of simple, and just for us, really could have bigger implications for how labor costs were impacting small and medium-sized independent title companies.
00:05:57 Anthony: Gotcha. So it sounds to me pretty fundamental to what you are doing is speeding up, aggregating, reducing some of the busy work, these trips to the county courthouse for title researchers. Have I got that roughly right?
00:06:12 Jennifer: That's it. And you can probably picture that it's really changing as more of these records are starting to go online. So my partner spends all day in one chair. It's like he can be four places at once because all of his counties are online.
00:06:27 Jennifer: I was still having to physically go down to my local courthouse every day. And we knew that our tool had to work for every scenario. When we look at how we're developing technology for these researchers, it's a hybrid case in most companies.
00:06:42 Jennifer: So they have in-house teams, they use outside vendors, some are physically going to the courthouse, some never have to leave their work from home situation. The commonality across all of them was that how do get that data from the courthouse into a technical workflow that doesn't disrupt the habits that they've already built.
00:07:05 Jennifer: And we knew that it had to be designed in a human-centric way that simulated the processes that they were so comfortable in, but did start to speed things up and cut out redundancy, cut out rekeying, a lot of waste that just really didn't need to be there.
00:07:20 Anthony: And so when you talk about title abstraction software, am I right to say that that's the core product?
00:07:27 Jennifer: Yes. Now, I think sometimes people hear abstraction software and they think click button, get title report, and it’ll the computers will prr, prr, you know put everything for you. For those of us in the weeds of this, we know that's actually very difficult because every county has a different database.
00:07:46 Jennifer: And you do want that human quality control, those QA checks along the way. So where TitleWise lives is between the researcher who is accessing those public records and the title examination or closing processor who is taking that finished report and clearing the title and preparing it for closing.
00:08:05 Jennifer: So TitleWise users have a portal where they are compiling their data in an easy way and they're creating beautiful reports without any actual work. So the computer is doing the processing but the human is still doing the thinking.
00:08:21 Anthony: Gotcha. I can tell you from personal experience of county tax assessor data sets, for our business Revival Homes, we're developing specialty financing for accessory dwelling units, ADUs, in addition to matching people to our network of trusted contractors.
00:08:40 Anthony: And part of the formula for creating specialty financing is being able to more accurately forecast what will an ADU add to the value of a home. It can be pretty significant, especially in housing constrained markets like Los Angeles, Orange County, Bay Area, San Diego.
00:08:56 Anthony: And so to build this model, we had to aggregate over 100,000 home sales in LA County. And the County Tax Assessor had this data and was willing to sell it to us at a pretty good price. But actually purchasing the data required me to go to the County Tax Assessor office on a Friday afternoon and pay cash in order to three days later get a link to a gigantic file on Dropbox.
00:09:26 Anthony: Then we tried to do the same thing in Orange County and it turned out that they were even less user friendly. We had to find the data from a third party source. And so when you started talking about stitching together multiple public county records, I started getting flashbacks to this whole undertaking.
00:09:42 Jennifer: That's it. You have described, I feel like the day in the life of a courthouse researcher. You take your laptop or your yellow legal pad from office to office to office. Sometimes the deputies working are, most of the time, I'd say super helpful, incredible civil servants who are there to provide information.
00:10:02 Jennifer: The same time, sometimes the technology they have means that there's not always access or you have to physically go into the courthouse. That makes it really hard to automate that retrieval process, which is why TitleWise kind of started to look at how do we empower the humans who are still having to physically be in charge of that data, but also use technology to make some generalizations and speed things up.
00:10:27 Jennifer: I'm curious when you guys are aggregating all that data and it comes to finding access to that bulk record purchasing, is that something that is impacting your working model? I know that's an activity or a conversation that's really evolving in real time these days.
00:10:44 Anthony: So we were able to take, I don't want to call it quick and dirty because that's not quite right, but let's call it an MVP type approach, where buying one enormous data set one time and sitting down with friends who are data science experts, do this kind of work for a living, helped us to get to quite high quality estimate.
00:11:07 Anthony: It's a point in time, but what it indicated to me is that, as we get this specialty financing to market and make use of the underwriting model, that indicates to me a clearer path for how do we refresh this with regularity? How do we get multiple counties to ingest data to the same place? How do we ensure that the model is living and breathing?
00:11:26 Anthony: Those are probably problems for another day. We have more fundamental problems to tackle right now. But you're right to say that this is something that defies easy scaling, but that there's value in going through the work to take something from zero to one.
00:11:41 Jennifer: That's fascinating. When we think about how we build these technologies that rely on data sources that we don't own, we'll never own, right? It's exciting to think about the potential and then also the dynamics of who are those stakeholders.
00:11:55 Jennifer: I'm on a work group right now where we're looking at how do business and government collaborate together to make policies that work for everybody. Governments, for example, want to make profits off of sharing this data they're maintaining. Businesses want to get it as affordably as possible so they can repurpose it for their clients.
00:12:14 Jennifer: And it seems county by county, state by state, the legislation that even dictates how much you can make that happen really varies widely. I just think it's such a live hot topic that's essential to anybody trying to build models and algorithms right now.
00:12:30 Anthony: So you think that for TitleWise, there's an opportunity to monetize from two different sets of customers, both these title research companies as well as local governments looking to license their data more effectively?
00:12:41 Jennifer: We definitely, at TitleWise, want to be supportive to the county. At TitleWise, yes, we definitely pay attention to how researchers and county governments interact. Those relationships are crucial. Often, researchers know the county systems just as well as the deputies that are employed there.
00:13:02 Jennifer: And we see those dynamics are very essential for collaboration for efficient workflows. When we look at how TitleWise profits, we definitely focus on how do we support the researchers in the work they're doing, whether it's physically in person, online, working from right across the street from your courthouse or across the world.
00:13:25 Jennifer: We know that settlement companies often have in-house research teams, but with the talent pipeline, we know title researchers are aging and retiring and leaving the field at a faster rate than new talent is coming in.
00:13:42 Jennifer: So there has been this kind of adjustment happening where title companies have a mix, some in-house, some outsourcing. Is the outsourcing a local company or someone in another country? And then do you need that local experience.
00:13:56 Jennifer: All these moving pieces are really influencing how I think software can help these companies troubleshoot when it's really about talent pipeline problem.
00:14:07 Anthony: Gotcha. So it's interesting that you mentioned the talent pipeline because one of the things that came to mind for me as I learned more about your business and background is that you set up shop in Southeast Indiana in the Louisville area. How have you plugged into local networks in order to find talent for your team? And have you had to look beyond the area in terms of remote teammates?
00:14:31 Jennifer: I like this question a lot. Growing a startup is a fragile thing. And we love our Indiana teammates who are located across the state, but we can convene at least monthly for real in-person work sessions. We think that's really important for cultivating the company culture and fresh ideas.
00:14:53 Jennifer: At the same time, we really value our in-house team members that are positioned across the globe. Our software engineers are based in Pakistan. The sales representative is in Jamaica and our customer service is in the Philippines.
00:15:06 Jennifer: We meet every day online, 7:30 ET, for early morning meetings for me. It's late night for them. And yet we still have this synergy and we get things done and we stay on schedule. So the technology has really enabled us to have a global team that's still fewer than 10.
00:15:25 Anthony: That's amazing. So you've been able to recruit English speaking talent from around the world and somehow make the stars align with the time zones. I think I recall is Indiana the state that has some counties on Central time and some on Eastern time?
00:15:37 Jennifer: It is. You're always terrified. Am I going to be an hour late or an hour early when I'm moving across Indiana?
00:15:44 Anthony: It's already hard to convene in multiple times since this adds another layer of 3D chess. How did you find and vet teammates who you've never met in person?
00:15:53 Jennifer: We were very fortunate. So TitleWise background, we were bootstrapping this until last year when we did some regional startup pitch competitions. We had a series of successes that gave us the capital, allowed us to bring in an experienced COO who had scaling experience and exits in his background.
00:16:15 Jennifer: With his network, he was able to help us find the in-house engineers who had already worked together. They had a dynamic. They had trust in his leadership. So that was one of those kind of serendipity points that we were very fortunate.
00:16:31 Jennifer: I think there are always maybe a few spots in a founder's career where you think, you don't like to think too hard about if that hadn't worked out exactly the way it did, because I don't have to worry about it. It did work out. So that networking, trusting our new leadership to help us build those connections was essential.
00:16:48 Jennifer: We've also worked really closely with our investors who are always there to guide and lend support, network, help. We found that the investor support has also been a unique access point for connecting with people that we would have otherwise never come across.
00:17:06 Anthony: That's interesting. You talk about the life of a startup moments on a knife's edge where things could break one way or the other and have very different ramifications. I mean, I've lived that myself with Revival Homes, I'll tell you.
00:17:17 Anthony: I'd love to know a little bit more about one of those moments where maybe you were really challenged and things ended up breaking your way and that that was a pivotal moment for the organization.
00:17:28 Jennifer: I think we're actually in one of those moments right now. We spent the better part of 2023 doing a lot of market research to really try to understand not just product market fit, but how do we find and serve our researchers.
00:17:44 Jennifer: Researchers often don't have websites or LinkedIn accounts. They are independents. In fact, our market segment is still 40% independents as opposed to businesses. We think consolidation will happen inevitably, but for now you still are kind of chasing down one or two person mom and pop shop.
00:18:04 Jennifer: Building that into a model had a lot of growing pains. And so when we were looking at how do we develop a sales program that meets those needs and is still scalable, it took a long time to line up those dominoes. But then finally you started to see you were tipping those dominoes and they were falling into place.
00:18:22 Jennifer: So we're now at this point where the dam is breaking, but there was that long, slow buildup that definitely caused a little stress, I'd say, around are we doing this right? Is this going to happen and fall into place? And then, yeah, the tumblers start to fall into place, but there's a little tension until it all comes together.
00:18:41 Anthony: Absolutely. I'm thinking of the slow burn, right?
00:18:44 Jennifer: Yes.
00:18:44 Anthony: I like thinking of it as your oil prospector in the Wild West, and you're drilling and drilling and drilling, and suddenly the ground starts shaking, right? It's like the payoff for that moment. It could take quite a long time.
00:18:56 Anthony: You've mentioned that your co-founder is also your husband and former colleague from your pre-TitleWise days. I'd love to know a little bit more about what is it like to work with him day to day? What are the pluses and how do you work through disagreements and keep some boundaries around not letting the business entirely take over your life.
00:19:16 Jennifer: It is so much fun working with Chris. We have a great dynamic. We know each other's boundaries very well, and I think we can read each other very well. When I first started working with him at the title company, he had all the experience. I spent about a year just learning and watching, and then slowly growing into my leadership role.
00:19:38 Jennifer: With TitleWise, we built it together from day one. So we really do feel like we can put our foreheads together, almost read each other's minds sometimes. That is very exciting and productive until it's not, right?
00:19:54 Jennifer: So I think sometimes our challenges are stepping away, talking to other people, getting outside perspectives, because we are so grounded in the same viewpoint. We share the same opinions. We sink on so many things.
00:20:11 Jennifer: Sometimes it's almost too homogenous and we need some outsiders to shake it up and give us something else and something fresh to think about.
00:20:19 Anthony: That's cool. I mean, my wife is, I call her our CEO, our Chief Encouragement Officer. She has an excellent mind for business. She's been at American Express for a long time. And so she can bring that outsider's perspective of, hey, this sounds great or hmm, I don't know, but yeah, I think to go to the next level and found a business with your life partner is definitely challenging. It sounds like it's very exciting too.
00:20:43 Jennifer: It is a lot of fun. Our personalities are also very different. Chris enjoys working alone. He likes supporting clients one-on-one. He takes a lot of satisfaction from small victories. When someone has that light bulb and they say, oh, this is going to make a big difference in my work, he will run on that steam for a month.
00:21:04 Jennifer: I alternatively love to be out and socializing and big team meetings and founder events, startup events. I love the energy and the people. So we have a very nice yin and yang dynamic when it comes to how we engage with others.
00:21:20 Anthony: Thunder and lightening, that sounds great. So what does success for TitleWise look like in your mind? If you're thinking ahead a couple of years, what does the business look like if the stars align?
00:21:34 Jennifer: Yes, I am very passionate about supporting title researchers in this changing economy. I know they face a lot of pressure from depressed prices, changing markets, different competitors. Success to TitleWise looks like supporting those workers to maintain competitiveness and relevance in a changing economy.
00:21:59 Jennifer: At the same time, we know that the changes are also, we're not going backwards, right? So for a TitleWise, success also means finding smart ways to increase automation. We want to keep moving forward with technology, but we're still keeping that human element always in place and in the forefront. I think success to TitleWise looks like scaling SaaS sales, but also really embracing the human element and always keeping that up front.
00:22:28 Anthony: That makes a lot of sense. It sounds like, you know, I've had advisors tell me about the need to have compassion for your clients to really put yourself in their shoes.
00:22:38 Anthony: And for us, I'll say our clients are not just our homeowner customers, it's also our rental property owner customers who want to put an ADU on the property, expand the income potential of the property. It's also our contractor partners.
00:22:52 Anthony: And in a way, I see some parallels where title researchers and home contractors, they have quite a lot in common in terms of there being an established way of doing things, but that it's starting to change. And sometimes there's, I'm not gonna call it resistance to new technology, but anything ranging from unfamiliarity or skepticism of new technology.
00:23:16 Anthony: And designing software that meets their needs, meets them where they are almost immediately makes their lives easier and more convenient in some way and leverages things that they're already doing, seems to be like a common formula for success.
00:23:29 Anthony: I think if I were going to sum that up in a word, the thinking of compassion for the customer, passion for the customer, how do I build something that makes them smile even is I think a really strong North star and a great way to define success beyond just pure business outcomes.
00:23:45 Jennifer: I'm so glad you say that and that you see that too. It's so fascinating to me in real estate. I don't know that it's always necessarily fear. Like you said, there's some skepticism. There have been people who have been actually burned by technology attempts before, and they have good reason to be doubtful.
00:24:02 Jennifer: But how do we get people to feel empowered to encourage their employees to take another look, to feel confident that when they are offering these solutions to their teams, that it's going to have the special sauce that they actually are counting on.
00:24:18 Jennifer: And I think you're right, that compassion, really understanding not just what their pain points are, but what's leading, what's underlying, how they got there is I think maybe the start of that success and how we start to make change and open acceptance for more technology and real estate.
00:24:34 Anthony: Yeah, I think you're absolutely right. I mean, quick story here. You talk about skepticism or making the user's life easier. We've debuted MVP software for our contractors to provide us with photos, videos, explanations of progress so far on the construction sites. So we've got contractors using this on five ADU projects right now.
00:24:57 Anthony: And sometimes we don't get updates. And you push and you nudge and you want to find out why. And it turns out that the MVP we built, you can upload photos one at a time. You have to do it in a specific way. And if the internet is not so great in the person's backyard, it's going to be pretty difficult to upload the photos.
00:25:18 Anthony: The other day I went to the home of this customer to go and take some photos and try the dog food myself, so to speak. And I said to myself, Jesus, this actually is pretty annoying. I get it why this guy doesn't want to do it this way and why he's just batch emailing me photos and then I'm matching them to the step in the construction project.
00:25:36 Anthony: And so the V2 is going to have batch uploading. It's going to have ability to save photos offline, things like that. And so, yeah, getting that sort of direct user feedback, even when it's not always what you want to hear or see is critical.
00:25:48 Jennifer: I am so glad you said that. When we tell people we designed TitleWise for abstractors, because we are abstractors, I don't know if that always resonates, but it’s true. We really care about this being user-friendly.
00:26:01 Jennifer: We want you to like using it. We've been handed down worksheets that didn't work for us in our own careers. So I think you're right. When we start from a place of empathy, understanding, the designs will be better.
00:26:12 Anthony: Yeah, I agree. Let's move things on to the speed round real quick.
00:26:18 Jennifer: Okay, fun.
00:26:19 Anthony: You got it. What is a book right now that you're reading or a podcast you're listening to that you really like?
00:26:25 Jennifer: Well, I use fiction as both an escape and a great source for important lessons. So right now I'm on an Ann Patchett kick burning through some of her novels and she's even coming to Louisville next month for the Kentucky Author Forum. So I'm just totally binging and geeking out on some Ann Patchett right now.
00:26:44 Anthony: I'm not familiar with her. What does she write about?
00:26:46 Jennifer: Oh, she's fun. Her most recent book was called Tom Lake. And I saw it in every airport when I was doing the conference circuit this year. But I feel like she does these neat character studies of beautiful New York spaces, they're smart people, their problems are human although not catastrophic. So it's really relatable storytelling.
00:27:09 Anthony: I love fiction as an escape from the day to day too, especially late at night or on the way to work and everything. I think being able to do that is not just fun, but necessary. If you could live anywhere in the world for one year, where would it be?
00:27:22 Jennifer: If I could live anywhere in the world, I would definitely go somewhere with a dry, warm climate. Maybe because it's wet and cold here in Southern Indiana right now, but I could do 24 hours of sunshine and thrive.
00:27:34 Anthony: Well, if you come to Los Angeles, you can have more than 24 hours of sunshine.
00:27:39 Jennifer: Might take you up on that.
00:27:41 Anthony: What's your favorite productivity hack?
00:27:43 Jennifer: My favorite productivity hack is having a notebook with me at all times. Scrap paper spaces in my calendar. I hate having a thought that was a brilliant thought, and I didn't write it down.
00:27:59 Jennifer: So I even keep a little TitleWise post-it stack in my car because a chicken scratch memo to yourself is so much better than it just being lost to the ethosphere. So yeah, I say always have something to write down that brilliant thought or it's gone.
00:28:13 Anthony: What happens if you have a good idea in the shower? I've had this problem myself.
00:28:17 Jennifer: I mad dash as soon as I'm dried off. I run and write that sucker down because it will be gone if I don't.
00:28:24 Anthony: I get it. I feel like such a grandpa, but I have the to-do list myself. I write things down in longhand, blue pen, legal pad, exactly the same as you do, I think. Just writing things down just makes it more real to me.
00:28:37 Jennifer: It's real and put it in a nice organized spot later, but just get it documented, darn it.
00:28:43 Anthony: That's right. And where can listeners find you?
00:28:47 Jennifer: You can always contact TitleWise through our website. It's www.titlewise.work. Not com, titlewise.work. And that's where you can contact us, learn more about our products, and we would love to see some traffic there because we are very excited to connect with more title settlement companies, their researchers, and their examiners.
00:29:09 Anthony: Well, I think that works as a great place to end things for today. It's been such a pleasure speaking to you, Jennifer. Thanks so much for making time to chat today.
00:29:18 Jennifer: The pleasure was all mine. Thanks to you.
00:29:21 Scott Harley: Thanks for joining us and hope you enjoyed today's episode. For those of you listening, you might also be interested to learn more about Everywhere. We're a first-check pre-seed fund that does exactly that, invests everywhere. We're a community of 500 founders and operators, and we've invested in over 250 companies around the globe. Find us at our website, Everywhere.VC, on LinkedIn, and through our regular founder spotlights on Substack. Be sure to subscribe, and we'll catch you on the next episode.