What is your favorite thing about Tampa?
Being a military kid, I grew up living in a lot of different places, but I really love the neighborhood feel. Tampa is a growing city and a developing city, but it still has that small-town feel to it. I knew more of my neighbors after living here for two weeks than I did six years living in San Diego. I knew two people in my neighborhood [in San Diego] who I think lived in the same house. I move here and there’s people coming up to my door, introducing their kids, bringing over some food, just normal Southern hospitality-type stuff. You can’t put a price tag on that. I never felt like they were bugging me though. It’s really just the size of the town, the speed of the city. It’s very comfortable for us.
If you had an unlimited shopping spree at one store, what store would that be?
I don’t know, I do all my shopping online [laughs]. I use Trunk Club. They ship you a variety of stuff, it’s not just one brand. They use a lot of different vendors, so that’s been super convenient. You can go through the site, see what you’re interested in, select it, and then they send it to you. Whatever you don’t like you put back in the box and send it back. They only charge you for what you keep, so it’s pretty convenient.
What is your favorite accessory item?
It would have to probably be my watches. I don’t have a huge collection, but there’s not many times [I’m not wearing one]. Whether it’s an athletic watch or a fashion watch, and whether I’m doing something nice or traveling, I rarely leave the house without a watch on.
What is the trend you are least into these days?
The super long T-shirts – those shirts that go down to your knees. There’s a difference between a long-line shirt and mid-thigh. There are kids walking around with long-line shirts down to their knees. It’s a dress!
Do you have any guilty pleasure foods?
Oh, for sure. I’m a foodie. I’m a big time foodie. I do try to, obviously, do everything in moderation, but I have a weakness for tacos.
If you were to send me to a taco place where would that be and what should I order?
Cask Social Kitchen, I have to send you to Cask [Editor’s note: Jackson is a partner at Cask]. We actually just started Taco Mondays because everyone does Taco Tuesdays. We have this whole branding thing that says, “Why wait ‘til Tuesday?” Our chefs have done a really good job with our tacos, but there are so many places. There’s a place near Cheval [Golf and Athletic Club] called Mekenita Mexican Grille. There’s plenty in South Tampa – like Catrina’s right on South MacDill Avenue. I like the hole-in-the-wall spots that aren’t really commercialized. I like the places that are more authentic.
Outside of the restaurants that you have ownership in, what is your favorite local restaurant?
I’d probably say Ulele and Del Frisco’s Grille. Kona Grill as well. Kona has the best happy hour. It’s really affordable, and you get some great food there. Also Cappy’s Pizza.
Finish this sentence: I can’t go to bed unless I…
Set my alarm. I have to make sure I don’t sleep in. My body’s on a clock, especially during the season. The last thing I do before bed is check the alarm to make sure I wake up.
How would you describe your personal style?
I would say casual. I’m more into comfort that I am fashion. I want things to be nice and to fit me well, but I’m definitely into comfort. If I can wear some nice shorts, a tank top, and flip flops, that’s kind of my thing with all the warm weather we get. When I do get dressed up, I want things to be masculine but not too dry. I like wearing warm, comfortable fabrics.
What are five things you could never live without?
Family is number one. My phone. I can’t act like I’m not going to need that – I’m an Android guy. Car. I like cars. I don’t have a collection or anything, I just have two vehicles, but I do like cars. I spend a lot of time looking at cars online when I’m bored. The fourth thing would be AmazonSmile [a program where Amazon donates a portion of the price of your purchase to charity]. And, finally, my DVR. I watch everything recorded.
What’s your favorite TV show at the moment?
I’m a “Game of Thrones” guy. I watch a lot of HGTV. I like to do a lot of handiwork around the house. I spend a lot of time at Lowe’s. They know me by name. I love doing little projects like that, stuff in my yard, in the house or with the kids.
What is your social media app of choice?
Twitter, just because of the fact that you get more links to real news stories than you do on Instagram. Instagram is fun because it’s all pictures, but my favorite is Twitter because I follow so many different things, especially what’s going on in the city. I follow a lot of news channels and finance channels.
What do you do when you get a day off?
Family time, first and foremost. I’m an entrepreneur, and I have a few businesses locally – I’m a partner here at Ferg’s Live. I’m also an owner-partner in Cask Social Kitchen on South Howard Avenue. I own a real estate company over on Henderson. I’m not going in and working six or seven hours a day, but we have team meetings, and I think it’s important for me to stay involved and keep a pule for what’s going on. It’s nice for them to see that I care. I get reports and emails whether I show up or not, so I keep track of the business, but it’s nice to go in there and get in the mix.
Do you have a favorite local event or festival?
Gasparilla Music Festival. I love Curtis Hixon Park. I think it’s a great venue. I also like the Hyde Park Fresh Market on the first Sunday of every month, we go to that all the time.
What’s on your playlist?
I listen to country, I listen to EDM, hip-hop. When I’m relaxing or cruising on long drives, I like to listen to old school R&B. So you’ll find a lot of different things on my phone.
You travel a lot. What’s your favorite city to visit and why?
I like New York. Whenever we get a chance to go up and play, it’s a one-of-a-kind city. Just to see the energy all day and night – it’s non-stop. It’s literally a city that doesn’t sleep. I feel like, when I’m there, there’s so much energy, so many cultures. Chinatown, Little Italy, SoHo, TriBeCa – there’s so many little niches in that city. You get so many different pieces of the world in one place.
Do you have any weird hidden talents?
I can ride a bicycle backwards. My grandfather taught me that when I was seven or eight years old. I have a strong memory, as far as recall goes. I can hear a song once or twice and pretty much pick up the lyrics or see a movie one time and be able to pick up quotes from it. My recall memory helped me a lot in school. That’s probably why I did so well. I could read a chapter and pull it all right back out for the test.
What did winning the NFL Honors Salute to Service Award mean to you?
Oh it’s humbling, for us to be such a young foundation – going on four years old now – it’s a pretty big recognition. For me, it’s about bringing awareness to our causes, having people really think about the families, how deployments affect them, how the kids are, about their mental and physical health and their education. We really focus on ways to get involved with that.
I couldn’t do it without a great staff, a great team of board members and awesome volunteers that help our programs. We’re very organic. It’s about activity. All our programs I’m involved in personally. I’m out there selling T-shirts, shaking hands, doing stuff. You can check on our website [jacksoninaction83.org] for all the events we do, from the baby showers to our reading program. The Buccaneers have been so supportive by allowing us to do tours once a month with kids in grades three through five who come if they’re showing progress in their literacy and things like that, so it’s a lot of fun.
What inspires you the most?
I would have to say I’m motivated by opportunity and how fortunate I am and not just taking that for granted. I grew up doing a lot of work with less fortunate people at the Salvation Army [and other similar places]. My dad and I would go out and do work on the weekends for charity events, cleanups, things like that.
Whether it’s kids overseas or third world countries or even in the town you live in, you see people struggling. Taking advantage of my opportunities and how blessed I’ve been to have had a great family and structure growing up and a good education [is important to me]. [I’m] building a legacy for my own children, showing them what it means to live a full life and be successful but also humble and socially conscious about the world around us.