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Episode 324 – Jeff Dinter, CEO – Gravy
Episode 3245th July 2022 • The Real Estate Sessions • Bill Risser
00:00:00 00:32:55

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  If you want to find answers and succeed in the real estate industry, particularly regarding home ownership, you have to be willing to research and talk to people. How can you close deals and get consumers to feel confident about their home purchases? Join your host Bill Risser as he dives deep into a conversation with Jeff Dinter about driving that entrepreneurial spirit in the real estate space. Jeff is the CEO of Gravy and a serial entrepreneur with a thing for product design who spends most of his career solving problems in the real estate tech and fintech spaces. In this episode, he shares his knowledge on how to work with agents and lenders to build great connections. He also discusses mistakes he has seen throughout his career and explains the new bridge he has created that hasn’t existed before.


Jeff Dinter - CEO, Gravy

We go into the heartland of the country, St. Louis, Missouri, and we are going to chat with Jeff Dinter. He is the CEO of Gravy. There are over 100 million renters in this country. What Gravy does is guide them down that path to home ownership. It’s very interesting. We are going to have a lot of fun with this conversation. Enough of this stuff. Let’s get it going.


Jeff, welcome to the show. Thank you so much for having me. I was very excited to have you on. I get a lot of requests from podcast bookers, and generally, they are from motivational speakers or real estate investors who, somewhere in their life, were poor. I love it when I find people starting up companies doing things a little bit different. We are going to talk a lot about Gravy, your company, but I always like to start in the same place. You grew up in the Midwest, but it doesn’t get more Midwest than St. Louis, right? That’s right. It’s the spot in the middle of the Midwest. Do you still live there? Is your company there? Tell me why it’s so special for you. Why St. Louis? I was born and raised in St. Louis. I had a brief stint in Orlando, Florida, with my fiancée at that time but my wife now. For a few years, we ended up moving back, and it’s still here. Gravy is very remote-friendly, but our flag in the sand is here. We have got a handful. Our team is in St. Louis. It has always drawn me back for sure. There are probably two reasons that I’m still here. One, it’s family. I have got mine and my wife’s immediate family. They both live within ten minutes of our house. That was a plus and a big part of why we moved back from Orlando before we had a toddler. Now that we have a child, it’s free babysitting plus family time, so that’s an easy one. Two is the tech scene in St. Louis. It’s been growing more and more over the past decade or so. There are lots of great people, great minds thinking differently, and engineers. I love the environment here. I hear that a lot from a lot of different places around the country. I don’t know if it’s the time we are in, and with tech being so powerful. These little areas before were not considered Silicon Valley. You’ve got them all popping up all over the country. It’s a great point to your comment. It started on the coasts, and slowly but surely, the density came in and may not have the density of East or West Coast in St. Louis or Kansas City. The good news is that even if it’s smaller, the overall concept of thinking differently, getting folks that either want to build software or reimagine different things, the density, appetite to take risks and start businesses are there. It’s a cool combination of founders, but also people that make good early team members at startups are all here. I love it. My readers know I have this weird thing with sports. You can see it all around me. Can I assume Cardinals fan, or are you like some other people I know from St. Louis who got bushwhacked into being a Cubs fan somehow? I have got two answers for this. The first is I’m stereotypical from St. Louis, diehard Cardinals fan for life, not against the grain. Growing up, I’d be lying if I said it wasn’t part of growing up that by default, if you were a Cardinals fan, you were not a Cubs fan. There’s truth to that. My mom’s family, so my extended family, is in Springfield, Illinois. They are in the Illinois state closer to the center, and that’s a mixed bag. Some Cardinals and Cubs fans. We had got some cool bickering that happened from when I was growing up, but at the end of the day, Cardinals fan for life. [bctt tweet="At the end of the day, businesses are about solving problems and finding big problems that a lot of people care about. There are new opportunities and problems to solve." username="billrisser"] You got Yankees, Red Sox, Dodgers, Giants, but Cardinals and Cubs are right up there with them. I’m sure it’s been a lot more championships for the Cardinals and the Cubs in the last hundred years. You always got that. What’s cool is that even if it’s early in the season, mid-season, every series between the Cardinals and Cubs feels like post-season. That’s always fun. It’s great baseball. I don’t know how old you are. Have you forgiven the Rams? The short answer is yes. I grew up 100% going to some Rams games. I never got into football as much as being in a baseball town. Cardinals were a big Blues fan. I loved hockey. With the Rams, I have got no hardcore burn. If you ask the same question to my dad, I think he has a better answer because he’s got a little bit more thoughts around it. I love competitive sports in general, not knowing the outcome of an event and the suspense that goes with it. I love any sports event that goes to the last quarter, last period, or last minute. That’s what I love about it, so yes. I have forgiven the Rams. I still watch football. I’m a Chiefs fan, but I’m not rooting for the Rams anymore. That’s all I have got. You mentioned the Blues. I live in St. Petersburg. I’m right across the bay from Tampa. If you had to pick a team before this started, did you want to see the lining one another or were you rooting for the Avalanche to get one for many years? The Avalanche eliminated us. There’s the conference debate versus rooting for Patty Maroon is on Tampa. He’s a St. Louis boy. I have lots of friends who went to high school with him, I believe. I’m Tampa Bay here, for sure. I do think that Colorado is tough to beat right now. They didn’t plan so well. It could go either way, but Tampa has my vote for the series. Some work to do. It’s all about Vasilevskiy. If he can have a game like you had on Monday night, things will get better, and I will get out of this because a couple of people turned off their podcasts who don’t care about hockey. Let’s talk about you growing up. I’m going to assume you are pretty techie. I was going to know that’s the case that you were playing with computers and all about that. If you are fifteen years old, a sophomore in high school, what were you thinking about doing? I was a techie nerd growing up. My dad loves computers. I had the old-school HTML books lying around the house. I’m learning generally how to code. I was taking apart computers. With that said, I was created at the end of the day. Less technical, more creative. I liked computers. I ended up going the designer route and not the engineer route. I understand engineering, but I’m a designer at heart. When I was fifteen, I was dead set on being a rockstar at that time. I was listening to music. That was the other creative outlet. It’s playing music in high school bands. After high school, I played music for the next 5 or 6 years touring the country for the better half of the year of all United States and Canada. It was a huge part of me jumping into the world because being in an unsigned band is hard. It’s almost like starting a startup. Fifteen-year-old Jeff wanted to be a rock star. As you can tell, it didn’t pan out. Otherwise, we’d be talking about my greatest hits, but I have shifted to the tech world. Now I will take it. Now you open the door. What’s the instrument you played? [caption id="attachment_4339" align="aligncenter" width="600"]TRES 324 | Home Ownership Home Ownership: We were ultimately a platform that helped property managers better engage with and retain their mobile-first renters, so the modern renter lives on their phone.[/caption]   I played guitar and sang. Lead or rhythm? Rhythm guitar, lead singer. If you were to compare yourself to a band that even an old guy like me would know, who would you compare yourself to? What was the genre you were in? We were pop-punkish. Blink-182 is probably the closest one because I grew up a pop-punk kid. I played guitar and wrote a lot of songs. I was the manager at the end of the day to where it was all business for me. I wish I had had more fun. It was all business. I’m trying to get the product out the door and have my business hat on before I knew it, but it was a great chapter in my life. I made a lot of lifelong friends and had great experiences. You were the guy herding the cats sometimes and in rock and roll. It’s got to be that way. I was a dad. Yes. Now we know where this entrepreneurial spirit comes from. You’ve done a lot of different things, and as I look back and see your history, it’s a lot of PropTech and FinTech stuff. Why did you go that route? I honestly don’t know when I fell into both PropTech and financial tech verticals. If you look at it from an industry macro perspective, those two industries have experienced so much change and evolution in the past decades around embracing technology. A lot of very old-school best practices and status quo around how the finance industry worked with banking. The same with real estate. No matter what vertical you are looking at or sub-vertical within real estate, whether it’s commercial, residential, or home buying investor, everything has been touched. Every part of the flow has had technology touch it, pull it apart, and try to reimagine it. That’s what attracted me to it at the core. At the end of the day, it’s solving problems and finding big problems that a lot of people care about as the underlying piece because, by design, those industries have gotten shaken up a lot. It means new opportunities and problems to solve, which is what pulled me in. It’s one of your greatest hits. It would be TenantLoop. My question is, was this your first look at the rental space? What was that pain point? What were you solving there? I’m always curious about evolution. [bctt tweet="If you like the idea of real estate and helping people solve problems, you want to build a product that helps renters have a better experience." username="billrisser"] A quick backstory on TenantLoop. We were ultimately a platform that helped property managers better engage with and retain their mobile-first renters. The modern renter lives on their phone, and at that time, this TenantLoop started as me scratching my own itch. My wife and I had an apartment at that time, and we had a bad experience. A lot of the problems stemmed from communicating with our property manager and messages falling through the cracks to the maintenance team if we had an issue. Paying rent was very old school. All the things that go into a great renter experience. If you think about living in an apartment or a single-family home, they were bad there. It made me look at the industry of, “Is there a better way to do this?” We had a bad experience. We didn’t renew the lease. We moved, even though we didn’t want to. The TenantLoop hypothesis was happy renters. They were new leases and I would have been one of them from that business hat. That was my first jump into real estate. I’ve always liked the concept of real estate. I didn’t know where I fit in. I wanted to build a product that helped renters have a better experience, and that’s what we did. It was acquired. Congratulations. That’s the goal of most people that are in that entrepreneurial spirit, but I also imagine it takes you out of the game for a little while. You probably had to hang around a little bit. Did you always know there was going to be a part 2, 4, 5, or 7, wherever you are at? Everyone knew there would be a next chapter. Myself, the acquiring company, my family, everyone knew. That was my first W-2 job. After the acquisition, we joined as part of that deal to keep building what we were building. What’s unique about that is that TenantLoop was at a pretty early stage. Honestly, our team knew there was a lot more work to do around the mission that we set out to do to reimagine this resident experience. We were excited to stay on. We kept building it and what’s cool is that it went from us having a few thousand renters on the platform after the acquisition, $2 million. It was a huge jump, and for us, that type of alignment with Buildium which is part of RealPage. That was acquired. They knew property management software very well, which is accounting, leasing, and a lot of the fundamentals of running a business. They had some tools around the TenantLoop concept, but we ultimately became their mobile bet, and we got to keep building that product, which was a great experience. That mobile-first is amazing, the ability to have the mindset. I think the mindset comes from a little bit of how you live your life. You are not lugging laptops around most times, only when you got to get the heavy lifting done. That’s obviously a big powerful part of what you did. I appreciate it and those fundamentals. The writing was on the wall that mobile was coming to real estate, particularly for renters. A lot of renters were interacting with their property manager on an old-school web portal at that time, and that’s not how you think of the peace of mind. The whole goal of that company was to enable property managers to give their customers peace of mind while they are renting with it. If something does pop up, because it will, it’s going to get resolved with the least effort and stress possible. We didn’t believe they had the right tools to do that from a mobile-first perspective. You’ve been a part of a lot of startups throughout your career. You joined up with others where yours. Are there some common mistakes that you see made? Especially now, I would consider you probably have mentor status for some people. There might be some people who find you and have questions. What do you tell them? I can say I have learned the hard way on many lessons here. To your first point, I’m very fortunate to be involved in a number of startups, some that which I played the founder role. Others that I was the lead product designer for very early-stage companies. I wasn’t the founder. The founders had domain expertise. They were the ones putting everything on the line to go solve the problem that they loved. I was leading design to figure out what that application looked like, felt like, and how we applied their hypothesis to a product. That’s what I loved, but what’s cool is both of those buckets get you exposed to so many different challenges that companies that are trying to do new things encounter. That’s both an opportunity and a risk. The two that come to mind for me are 1) I will call it Founder Tunnel Vision, and then 2) The art of delegation. Founder tunnel vision, this is why the magic happens. It’s when founders see something that no one else sees. They have a vision of how to solve a problem in a different and meaningful way, but that doesn’t mean you should be closed off to feedback along the way. That could be as simple as early idea validation to make sure that your potential customer cares about that problem as much as you do or making sure that it’s not isolated or too specific of a problem you are solving. Also, once you launch that feedback loop of getting feedback from consumers, that may not always be the feedback you’d want to hear, but ultimately for great ideas to win, make sure you are open to getting that feedback and incorporating it. That doesn’t mean you can’t have the product company perspective of like, “You won’t know this or won’t understand it until you see it and we are going to build it so you understand it. [caption id="attachment_4340" align="aligncenter" width="600"]TRES 324 | Home Ownership Home Ownership: Magic happens when founders see something that no one else sees. They have a vision of how to solve a problem differently and meaningfully.[/caption]   You don’t have to lose that big bet, but getting the feedback and the feedback from consumers, customers, and partners is important. At the end of the day, you can’t do everything. Find people that are very good at what they do and build your team from there, and I have learned that the hard way because I’m a doer. I like getting through the to-do lists, but a startup launching or a growth stage company that maybe has new initiatives. It’s always relevant to make sure you’ve got the right people in the seats to do the job and prioritize ruthlessly because the to-do list will never get shorter. I think it’s just important. Something we have not perfected, but we practice at Gravy the best we can. I love your use of the word ruthlessly. It’s the same with the company I’m with now. There’s no just cruising along. It’s got to be everyone’s in working in the same direction or focused on the same thing. We are all moving there as fast as we can. We know because of the band experience, that’s your doer part. My bad, we didn’t get the name of the band. You got to throw that out there. You haven’t heard of it. One is called Lowercase. The other one was called The Vanity Affair, which was a spin on the magazine title. Hoping that people thought they had heard of us before. It’s a really bad idea. It worked, I guess. That’s where eighteen-year-old kids for you make business decisions. I’m glad I went back to that question. That’s great. Let’s get into what Gravy does. There are a lot of companies that help people beat out cash offers. Debbie is out there. I think they are helping renters become owners, but all these companies like Ribbon, Orchard, Flyhomes and Knock. They are not what you do, but they are all doing the same thing. Did you find a lot of companies? There had to be some that were doing close to what you were doing. What was that vision? What led you down the path with Gravy? From a macro lens, the awesome thing here and you touched on it is there have never been more new companies that are trying to reimagine parts of the home...