Revitalizing a Town & Running Multiple Businesses - Jena Dennis' Story

Hometown Jax brings you the inspiring stories of Jacksonville’s entrepreneurs, innovators, and community leaders. Hosted by Jason Kindler and Aaron Bacus, this podcast dives deep into the challenges and triumphs of local business owners who are shaping the city's future. Whether you’re a business enthusiast, a Jacksonville native, or just looking for motivation, Hometown Jax is your go-to source for real stories of perseverance and success.

In this episode, Jason sits down with Jena Dennis, a sixth-generation Jacksonville native and the powerhouse behind multiple thriving businesses. From running a real estate brokerage to managing estate sales, auto brokerage, and even a federal firearms dealership, Jena does it all. But her passion for revitalizing the historic town of Hastings is what truly sets her apart. She shares her journey of transforming nearly half the town, the lessons she’s learned as an entrepreneur, and how she balances business and family. If you want to hear an incredible story of vision, resilience, and community impact, this episode is a must-watch!

Transcript

00;00;00;00 - 00;00;14;29
Unknown
Where are your hosts, Aaron Backus and Jason Kindler? We like to sit down with our guests to hear their journey, their challenges, and how they impact the local community. So grab a seat. Tune in and let's get inspired by Jacksonville's everyday workforce. Welcome to Hometown Jacks.

00;00;15;01 - 00;00;36;04
Unknown
Hometown Jax podcast. We are here with Jenna Dennis and I am so excited because today I can tell you we did not prep, we did not do any prep. I know a little bit about your story. I know that, there's there's probably a lot I don't know. So I can't wait to can't wait to dive in with you.

00;00;37;08 - 00;00;56;29
Unknown
So this is a, a podcast all about people of Jacksonville. So, tell us a little bit. Are you from Jacksonville? Are you born and raised? Yeah, I'm six generation, six Asians. Yeah. Are you the only person that's six generations? I don't know, I don't know how rare that is, but like, a lot of people are like, well, you're I'm a Florida native.

00;00;56;29 - 00;01;18;00
Unknown
Well, I'm actually a Jacksonville, Florida native, so. Wow. Yeah, I bet I would maybe do some research on that that you got to be one. Yeah. Right. So, tell us a little bit about your, tell us a little about you. So you obviously grew up here. Tell us a little bit about what you've seen in, in Jacksonville.

00;01;18;00 - 00;01;20;08
Unknown
I mean, it's it's definitely grown, right?

00;01;20;08 - 00;01;36;04
Unknown
Yeah, it's grown a lot. I mean, I was born in the 80s and, you know, looking at it now as opposed to back then, it's totally different. You know, every time I go into a new area, I feel like there's some kind of new development or something new going on. So it's it's bittersweet.

00;01;36;06 - 00;01;44;04
Unknown
You know, everyone thinks just because I'm a real estate broker, that I love development. But there's something to be said for, you know, this quaint small town feel.

00;01;44;04 - 00;01;55;16
Unknown
It's. Yeah. So, that's how I, you know, we, we kind of know each other and, is on the real estate side. So you, tell us a little bit about that.

00;01;55;16 - 00;01;57;19
Unknown
You own you own a real estate brokerage?

00;01;57;19 - 00;02;09;09
Unknown
We do. My husband and I own Great Expectations Realty. And we cover all of northeast Florida area. And we've had it for, gosh, since 2017.

00;02;09;09 - 00;02;23;06
Unknown
Got it. So, yeah. So just because I know a little bit tell I tell me one other thing that you're and I want to get to all of it, but tell me one of the things I mean, I know you do real estate, but what else do you do?

00;02;23;09 - 00;02;46;00
Unknown
So our business motto is we can sell your home or business and everything in it. And, yeah, what that means is we are licensed in a lot of different facets. So we're a licensed auction, an estate company. We're a licensed auto broker where it licensed federal firearms dealer and a licensed real estate broker. So literally everything in anything and everything.

00;02;46;03 - 00;03;07;26
Unknown
Okay, so I love us because the attorneys, we're a one stop shop. Yeah, we can pretty much take an entire situation, whether it's a divorce or someone's passed away or it's a re, you know, reorganization of a business. And we can handle every single asset they have. So. Wow. So let's start with the, let's start with the let's start with firearms.

00;03;07;29 - 00;03;31;06
Unknown
Yeah. So tell me a little bit about that. Oh the guys always want to. Yeah I know right okay. Right. Yeah. So we got our federal firearms license probably ten plus years ago. And, you know, I came across a lot of estates where they'd have large collections. And I felt it was important to really be an expert in the industry and know what I'm doing and handle them, you know, by law.

00;03;31;19 - 00;03;51;23
Unknown
So we decided to get our license, and it's been great. We mostly do secondary market, you know, collections or estates or, you know, if someone's wanting to sell a few. I don't do a lot of one off. It's just a lot of work and time. Sure. Transfers if you're not doing a large bulk amount. But it's been great.

00;03;51;26 - 00;04;18;12
Unknown
That's amazing. The other thing you said was the auction. Tell me a little bit about that. So, so I've been doing auctions and estate sales for a really long time. That's actually kind of what started all the businesses is I had a little antique store in early 2000 and got it. Okay. Had a lot of fun, but I would have a lot of people come to me and say, okay, you know, I want to sell this.

00;04;18;12 - 00;04;35;21
Unknown
Or they'd come to me and ask me if I'd buy some of their stuff. And, you know, we just saw a need for it in our community and decided to do estate sales. And next thing you know, I was getting my auctioneers license and expanding my antique store and it just kind of exploded. One day I woke up.

00;04;35;22 - 00;04;56;16
Unknown
Wow. I was like, I was doing 15 different things. So, so on the on the auction side. So is it do you do the auctions is you and your husband who who does the auctions. So I am a licensed auctioneer, but so is my husband and so is my brother. Okay. So it's definitely a family ordeal. Gotcha.

00;04;56;16 - 00;05;16;23
Unknown
I always preferred to do more of the business end of it and let the guys do the calling. You know, I growing up. And Amanda will tell you, I was, like, painfully shy. I was kind of a quiet introvert. So coming into myself as I, you know, became more mature and became an adult and whatnot, I really had to, like, push myself to be an extrovert.

00;05;16;23 - 00;05;37;18
Unknown
And so interesting. It was a slow start getting into the auction world. You know, it took me a couple. I mean, that's like the opposite of an introvert. I know that's that's the opposite. So let's let's go down that path a little bit because, you know, obviously we have, you know, our viewers, a lot of of business owners, a lot of, you know, people that are in in business.

00;05;37;20 - 00;05;59;09
Unknown
I personally I tend to be an introvert first. And I've learned how to be an extrovert. So how does one, not to the auctioneer side, not to that extent, but how do how how did that journey go like so you were shy growing up. Yeah. Did you teach yourself or just kind of come one day? It was baptism by fire.

00;05;59;10 - 00;06;15;27
Unknown
Really? Sure. Yeah, I, I in college, I remember one of my professors telling me I was kind of quiet and soft spoken, and she said, you're never going to make it in business. As a woman. You're too soft spoken. You need to protect your voice. And she just kind of like, gave me a smack in the face.

00;06;16;00 - 00;06;33;03
Unknown
And I was, you know, that always resonated with me. If anything, I think it pissed me off. And, you know, I was going to I'm sure I'm going to turn right to do the opposite of what she said. And I originally got my auctioneers license thinking I would hire someone for calling. I just wanted to own the business.

00;06;33;03 - 00;06;54;22
Unknown
Yeah, that was the part that excited me. Well, you go to try to hire an auctioneer and it was expensive as a new business owner. You know, I was starting with nothing and I was like, it's pretty much me, you know, I've got to do this. Church trial by fire. Yeah, true. Trial by fire. My first auction, I remember I was mortified and I was sitting up on this stage.

00;06;54;22 - 00;07;14;19
Unknown
There were a couple hundred people in the crowd and you could hear my voice shaking. Oh, wow. And I knew people could, like, I was physically shaking. I was so, like, nervous. So about 20 minutes into it, I forgot that I was scared and I just found my groove and it was like, for going and going and I think, you know, for maybe a year.

00;07;14;19 - 00;07;37;11
Unknown
I was a little anxious about it, but now it's like it's old hat. I just it's like I flip a switch and I'm on. So can you flip that switch now? I can't. Oh my goodness. I was hoping you would say this cell though. What about this. All right. This is a this is a money sign with little dangling legs.

00;07;37;26 - 00;07;55;21
Unknown
Very rare. Definitely rare. It it may be a one of one kind. I believe it's missing a piece right here, but it's an it. It's an antique. Okay. All right, all right, so I got to hear this. Tell me what you do. Well, I mean, it's kind of hard when you don't have a crown to interact with, so you're going to have to bid for me.

00;07;55;28 - 00;08;18;03
Unknown
Okay. But, you know, I'll just. What do you think this is worth? This money symbol. Oh. What is it? 5000. Oh. Let's go. 5000. Here we go. Ladies and gentlemen, we have this beautiful money symbol started out. How about a $5,000 bidding bid at 5000 bid 5000. How about 2000 and go 2000? And anybody at 2000?

00;08;18;10 - 00;08;39;26
Unknown
I've got 1000. How about to hit a bid to. I'm at 1000. Bid 2000 and 2003 thousand. We're at 3000. 3000. Bid for I'm at 3000 bid for. So I'm. Oh my goodness that's so good. So I don't do like the cattle auction chant where, you know, you can really speed up. I mostly sell like art and antiques and, you know, cars, things like that.

00;08;39;26 - 00;08;57;23
Unknown
So we intentionally slow our chant down a little bit. Got it so people can hear us. But, you know, I have a friend of mine, Steve, who is the manager of our brokerage. He's an auctioneer as well. Oh, and he can, like, spit it out. He's like a cattle auctioneer. It's amazing. That's amazing. Great job. That's that.

00;08;57;23 - 00;09;21;07
Unknown
That was cool. That was cool. I that's definitely I, I definitely can't do that. You can with practice. I can with practice. Oh man. So that's pretty cool. So estate sales and and tell me about the auto brokerage. What what is the auto part. Yeah. So we got our auto license. Same reason, you know, people just coming to us.

00;09;21;07 - 00;09;48;13
Unknown
And it was a part of a lot of estates. So, we decided to get our license and then really branched out when we were contacted by Saint John's County. And we started doing all of their surplus assets. So we sell, and we do it for a couple other counties and municipalities as well. We do City of Palatka and basically what we do is anytime they have what we call rolling stock, which is a titled vehicle, it can be a truck, a trailer or a bulldozer.

00;09;48;15 - 00;10;09;25
Unknown
You know, whatever we run it through auction and we do these surplus auctions usually 2 or 3 times a year. So that's primarily what we use our auto brokerage for. And of very, very if we're doing an estate and someone's got a car, it allows you to sell that as well. That's that's one stop. Yeah, man. Truly. That's amazing.

00;10;12;15 - 00;10;35;08
Unknown
I know, I know a little bit. I'm just going to. I'm mean, what else are you doing? Well, I am right now. We have a lot going on in Hastings. Okay. Seems to me like what we're getting a lot of media for lately. My husband and I used to own a building in Springfield, downtown Jacksonville, and, if you're familiar with re threaded or.

00;10;35;11 - 00;11;01;29
Unknown
Yeah, absolutely. So re threaded, but what we call the compound from us. And when they did, we had to move our business to a new location. So we were looking all over and we found a beautiful historic building in Hastings, Florida. Okay. And Hastings is right outside of Saint Augustine. We purchased this building, and one thing led to another, and we ended up buying a lot of buildings in that community.

00;11;02;12 - 00;11;24;05
Unknown
People joke like you bought half the town, but we really did almost buy half the town. And we've been so blessed because we've had such amazing community support. And that's we've been. Yeah, we've been renovating these buildings one at a time. Yeah. And getting new businesses to move into town. And since then, we've also sold several buildings for customers on the street.

00;11;24;05 - 00;11;51;04
Unknown
And truly in two years, we've been able to help through. We started a nonprofit. Yeah. It's called Hastings Main Street. Okay. And we have completely redeveloped this community. And, you know, we're working on the economic redevelopment. The historical structures are all getting renovations. It's really become a passion project. So I can I could tell your face was like, yeah, light up, I love it.

00;11;51;04 - 00;12;10;00
Unknown
That's amazing. Yeah. I don't know anyone that's that's done that. Yeah. It's it's been so rewarding, adding I tell you, like I get so much joy from it. And it's, it started out as, you know, a real estate investment. Yeah. It turned into so much more like so many people in that community. I feel like they're family. That's awesome.

00;12;10;04 - 00;12;37;16
Unknown
Yeah. So the, the, the people that live in Hastings, I mean, they gonna love you, right? I hope so, oh, yeah. I mean, you know, I did see, you know, one of the buildings I like, it's. Yeah. Before and after it. I mean it's completely, completely different. It's amazing. It's cool. It's really neat because we're helping a lot of other business owners in the community recognize and achieve their dreams of opening a business and starting a business.

00;12;37;16 - 00;13;03;06
Unknown
And, my husband and I apparently lost our minds and decided one of the buildings we were going to turn into an event venue. Okay, so we are also in our free time, opening an event venue which will be will hold weddings, corporate events. Sounds like you have a lot of free to go. Well, now that I've given up sleeping right, it's working out, so.

00;13;03;08 - 00;13;26;19
Unknown
That's so good. What what? I mean, I just, I this is amazing. Like, that's that's so much so much going on in, in your life. What, any other projects that you have. No, no. Any of the things that you've done that are I mean, I just I mean, those are kind of those are the big ones keep me busy that my babies I have three amazing kids.

00;13;26;20 - 00;13;47;12
Unknown
Okay. Yeah. And my husband and I really try to raise them super involved in our businesses. So, you know, each of them has their own company and they're all on payroll and they work. They work with us. And how are your kids? So my oldest is 11 okay. My middle is nine and my baby is seven. Oh my goodness.

00;13;47;12 - 00;14;12;12
Unknown
Yeah. So it's been fun. That is real. That is real world. I mean firsthand like experience education it's been that's incredible. All of it. And we really that's for us. That's what Hastings has become is kind of a legacy project because we're not in it to flip any of these properties, like we're invested long term, and we're growing and building what we consider our family's legacy.

00;14;12;12 - 00;14;33;05
Unknown
And one day I want my kids to take it over and, you know, learn all the aspects of being a business owner, you know, from cleaning toilets to all the way up to. So it's fun. That's Jenna, that's a I mean, you you that's an amazing story. Amazing story. I mean, that's and I know you're continuing on with that.

00;14;34;04 - 00;14;54;02
Unknown
Gosh, I think as people, you know, get older, myself included, it's like, you know, you you work, you do things. But what you said with legacy, I think that's such an important, important piece of it. Yeah. It's something that definitely on, you know, I've thought about recently and it's like, okay, well, this this is all good.

00;14;54;02 - 00;15;19;04
Unknown
But you know what does that look like for, for for the future? Yeah. One of our goals, we just, in our free time, we, we just started doing, travel agency. So my husband is, is now officially an Expedia travel agent. So now we're adding travel. Now it's Travel Weekly. Trish, this is a I mean well let me tell you why.

00;15;19;04 - 00;15;39;27
Unknown
So we love to travel and our long term goal once everything is you know up and running and the renovations are done, all of these buildings will be passive income. So and that's one of the things that is I'm really passionate about is setting up my customers in real estate for long term success. And most of the time that's through passive income opportunities.

00;15;39;29 - 00;16;00;24
Unknown
So I preach hard in big about that. But once we've achieved that goal and we're at a point where we can, you know, step away, our goal is to travel with the family and take them all over the world and, you know, do kind of some travel blogs with the kids. So by adding the travel dining, I'm sure there will be a business behind that.

00;16;00;26 - 00;16;21;25
Unknown
You like it? Yeah, I could see it, I totally it we just got all of our LLCs lined up and you know, we're branching out into the travel industry now. Wow. That's amazing. So on the, where where where do you guys usually travel? So we mostly have state stateside. Yeah. This summer we're going to Europe for a month.

00;16;21;26 - 00;16;40;00
Unknown
Oh, cool. Yeah. And we're going to go, you know, we're going to start out in Ireland and we're traveling with some dear friends that are from Ireland. And then, we're going to pop over to Paris and travel all over Europe for a couple months and then pop over to Switzerland to see my husband's brother. And that's so cool.

00;16;40;01 - 00;17;03;12
Unknown
Yeah, well, I mean, speaking of that, I mean, the entrepreneur side, like most people can't pick up and go for a month. Yeah. So that's what I kind of set yourself up that way. Yeah. I've been blessed with an incredible team. I have, two full time ladies that work with me, that one of them is my T.C., and the other one is my executive assistant, and I couldn't do what I'm doing without the two of them.

00;17;03;12 - 00;17;28;06
Unknown
Yeah. You know, they are amazing. They not only bring me joy and keep me stable, but they support me in so many ways. So it's great. I can work from anywhere. And that's what I love about this industry. That's amazing. Teamwork, makes the dream work. It does. It really does. It really does. So I, I've been by your, broker shop several times throughout the years.

00;17;28;08 - 00;17;49;24
Unknown
I have to ask. There's a giraffe outside a life size. There is a life sized giraffe. And you're in in for our viewers, the, You're in Saint Augustine. What? What studio? Right at the corner of King in the US. One king in us. One. So next time, King us one or you're in Saint Augustine, you got to go by King in U.S one.

00;17;49;24 - 00;18;06;03
Unknown
Tell me about this giraffe. I've never heard the story. I just know I'm like, oh, there's the giraffe. It's it's not as exciting as one would think, but I, I have always loved giraffes. Okay. And I told my husband one day I want a live one, a real one. And I'm not joking when I say that I will have.

00;18;06;03 - 00;18;23;06
Unknown
I know you'll have a real dream like I will. Just knowing a little bit of your story, I'm like, yeah, you'll definitely have a dream and I'll tie into that in a minute. I'll tell you why. But first, to answer your question about why the giraffe. So people have always bought me like, giraffe stuff and like little like, it's just been a thing.

00;18;23;10 - 00;18;44;14
Unknown
And one day, like, a month after Covid hit, we were all in lockdown and it was like everyone was so morose. And it was an intense time. Yeah, it was really mentally. There was a lot going on, so I was shopping online and I see this lifesize giant like elephant and I'm like, I wonder if they have this in giraffe.

00;18;44;16 - 00;19;03;22
Unknown
Oh, so I started googling and next thing you know, I found a lifesize giraffe and I, my husband is so good natured. He puts up with all my antics. And I went home that night and I'm like, honey, I love you. I bought a giraffe. And he's like, didn't know where to go with that. I made it over live.

00;19;03;25 - 00;19;27;03
Unknown
Yeah. Didn't know it. First plane. Well, the challenge was we are on the busiest intersection in Saint Augustine, and the semi truck delivering the live side draft couldn't get into our driveway because it would take the power lines out. So we called. I have a friend that was at the police department. We called and we got a police escort to shut down us one.

00;19;27;05 - 00;19;47;17
Unknown
It's like the busiest intersection to. Yeah, and they did. They did it. Everybody and people were honking as we pulled this massive giraffe. There were six grown men like trying to pull this thing out of the semi. And I have videos you would just die. It was so funny. It's so funny. But it was so fun. And the reason I did it was it just gave people a reason to smile.

00;19;47;17 - 00;20;05;20
Unknown
Like we decorate them for holidays. And, you know, during the summer, he gets a rubber duck float. That's cool. It's just it's just a whimsical like, oh, look at the giraffe. Okay, so there is, it's there's a there's a story behind it. So, so there's a story behind it. And I love that you I love that you decorate it.

00;20;05;20 - 00;20;27;14
Unknown
Yeah. So it's tie in. I'll tell you why I'm getting a real draft soon. Soon. So we have our our office is about 6000ft². It's a huge building. And obviously, like, we don't need the whole space. So I rented out the back portion of the building to that new capybara cafe that just opened in Saint John's County.

00;20;27;14 - 00;20;44;23
Unknown
Yep. Did you hear about I hear, I heard, so it's amazing if you've ever wanted to. Oh, that's me. And like she has the first time I heard about a capybara right now to tell us what a capybara I had to Google it, I did too. It was like, what the heck's a Cappy bar? I thought she was saying Kookaburra.

00;20;44;26 - 00;21;05;24
Unknown
Yeah, this woman calls me. She's like, hey, I'm interested in running your space. And I thought she was saying kookaburra. So I finally google Cappy Bar and it's a giant rodent. It's like this massive. She's laughing. It's this massive rodent. And it's like it's fuzzy and, you know, it's like got bristly fur, but they're cute. I mean, truly, they are cute.

00;21;05;26 - 00;21;28;15
Unknown
So she's like, I'm going to open a capybara cafe. And I'm like, okay. And I Google it. And yeah. So she owns an exotic pet rescue. And interesting. Yeah. She has this amazing rescue in Hastings, Florida. And, we became friends, and she has the license for me to get a life sized drop. So we've been collaborating.

00;21;28;18 - 00;21;48;19
Unknown
Her husband and my husband are, like, trying to keep us away from each other because we're just. So she has all these amazing animals. So we've been talking about how much acreage do you need for a giraffe? And, you know, setting out our plan. So one day we will have a giraffe. I know you will. I mean, the and now you know, the person that can actually know, right.

00;21;48;21 - 00;22;11;10
Unknown
Facilitate this. And then meantime, I get to play with capybaras and other. She has a skunk. She has, Gosh, she's got one of those mini kangaroos. She's a mini kangaroo. It's amazing. If we carry it around in this, it's it's in her house or. No, it's in the building. In my office. Oh my goodness. Yeah. And she's okay.

00;22;11;10 - 00;22;31;22
Unknown
I got a kill baby albino armadillo. That is adorable. I want to come see. But now I really want to get. You need to come see me. All right. I got raccoons, like, depending on the day, you never know what it's going to be like crawling across the back office. I didn't, I knew a couple of your projects and things like that, but I did not know where this was going to go.

00;22;31;24 - 00;22;52;28
Unknown
And it went. It went so much, so much like the I that's that's never know. You never know. That's amazing. You live a very interesting, exciting life. Well thank you. Yeah. You do. Yeah you do. And you're very successful. And I think, you know, just knowing a little bit, I'd know a little bit on the real estate side.

00;22;53;19 - 00;23;19;05
Unknown
I know people that work with you. Absolutely. They love you. You know, and that's. I know that's your reputation. And I'm sure that all of your other businesses and everything like that follow. Oh. Thank you. Yeah, I appreciate that very much. It's been fun getting to know you a little bit. Yeah. So I, I just wanted to, you know, again, do you have anything else you want to talk about?

00;23;19;05 - 00;23;52;17
Unknown
Do you have anything and anything else? I think, I mean, I feel like we've talked. Okay, okay. Yeah, I mean, that's that's a lot. We have, you know, we have a lot of guests on that. You know, it's it's pretty narrow, focused. This is you. Do you do it all? So, we, we definitely, you know, for anyone who's who's watching, if if you have the auction side, the real estate side, if you want to go pet some, that some animals, I will sell you a house and let you pet our capybaras and sell every.

00;23;52;17 - 00;24;14;20
Unknown
And sell everything else. Tell us your tell us your tagline again. So we're at, GE Realty, our Great Expectations Realty, and it's Jenna Dennis. So you'll sell the house. We can sell the house, the business and everything in it. Everything in it. That's so good. Yeah. Thank you for coming on. I appreciate it. And, and we'll, we'll definitely talk soon.

00;24;14;20 - 00;24;19;07
Unknown
And I'm coming. I'm coming to see everything. All right? Sounds good. All right. Awesome. Thanks, Jenna. Take care.

00;24;19;07 - 00;24;33;13
Unknown
The Hometown Jack's podcast is recorded and produced by First Coast Mortgage Funding. Located in the heart of Jacksonville. Do you want to be our next guest? Visit our website at Hometown Jack's podcast.com. We can't wait to hear your story.