1646 W Snow Ave Suite 10 Tampa, FL 33606

Tampa Bay Tech Leaders: Tony DiBenedetto, Technology Executive and Community Builder

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders

Tony DiBenedetto has been a pillar in the Tampa tech community for over 20 years. We’re thrilled we got the chance to interview him and catch up on what he’s doing post-Tribridge, including his work on various boards, and with Think Big For Kids.

On his career highlights

Roxanne Williams: You’re quite beloved in the Tampa tech community. One of the questions we ask everyone is, ‘who is someone that is doing something right in Tampa?’ and you’re mentioned quite a few times for your work at Tribridge. Considering you’ve had such a strong career, what are your highlights or your proudest accomplishments?

Tony DiBenedetto: When I saw the question, a few things popped into my head. One thing that I felt defined us was the culture of the company. I define culture as how people interact and behave: how do they behave when the lights aren’t on and the camera isn’t rolling?

The thing about Tribridge that I felt so connected to and that really epitomized the culture is the mission statement that we had for 20 years. It was so simple: to improve the lives of others by serving them.

It’s both an external message and an internal message.

Externally, our leaders and our people were always on boards in community organizations, and they were leaders in those organizations. We also helped clients with their businesses and we made them better.

Internally, the things we did for each other over that 20 years… You see people go from young people to mature adults and leaders. We had the geography of both the United States and a little bit in Europe, but you’d never know that. The way people connected – we even named our annual meeting Connect. We did a 3-day meeting every year with every single person in the company. Everybody kept saying it was too expensive, and I said we couldn’t afford not to do it, because it was the gel of the company.

The proud moments were just the smallest things. I remember one of our employees in Texas. His wife was diagnosed with cancer, and she passed away very quickly – within 3 months. 4 kids, she was a stay at home mom in Dallas. I remember how the whole company rallied behind the family and ultimately cooked meals every day for a month, and they gave him – collectively between other people’s vacation and the company matching – a year off to recuperate and focus on the kids. And this was people that were in Tampa, New York, California. We all rallied behind. That happened over and over again – with good things too, not always things of tragedy. But it was so defining the whole way. And it wound up defining even the business model.

When we decided to get into healthcare, we got into preventative health, and it was because there was a passion with one of our leaders. He felt like we were doing everything after the fact instead of trying to help people before they got sick. So, we actually built an app that connected all these IoT devices in a care plan to help people before they had a heart attack, that may be predisposed, to track everything in real-time with the healthcare provider.

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders - Legacy

The second big thing for me was a lot of people came to the company and left to become entrepreneurs. People would go, “Why would you celebrate people leaving?” Well, I love entrepreneurship, I love watching people take a risk and fail, and I love watching people take a risk and succeed. I like changing the game. In fact, I believe the whole economy of the United States is fueled by small businesses and the entrepreneurial community. Tampa changed so dramatically because of it. When people would come to me and say, “Hey, we’re leaving,” instead of that knee-jerk reaction of “Oh, what does that mean Tribridge?” the first reaction I – and others in Tribridge – had would be, “How can we help you?”

We probably had 20 or 30 people leave at some point and start their own company. There’s a cool feeling about that, and now that Tribridge got sold, there’s this legacy of companies out there that were former Tribridge people, and it feels like we’re continuing to contribute to the Tampa ecosystem.

Matt Vaughn: To tie into how important you put that weight on really holding yourself to the mission statement and a lot of–

Tony: We were very purposeful is the word I would use.

On purpose, culture, and passion

Matt: Yeah, purposeful. There are a lot of startups around Tampa Bay where they’re putting a focus on that. But there are also a lot of companies in the area that don’t really do much to be purposeful. What kind of advice can you give people trying to shape an organization into something like that, where culture and purpose take a strong forefront?

Tony: There’s no question that the fastest path to making things like that happen is getting buy-in from someone on the leadership team. If I was trying to start something like that, I would first walk the walk. I mean, if you’re going to be somebody that wants to define culture, then you’d better act that way. Otherwise, nobody’s going to take you seriously. There’s nothing real about talking but not doing.

The second thing would be – when I was young, I was fairly confident when it came to talking to people of authority. I would probably pretty quickly say to somebody on the leadership team, “Listen, I feel like I conduct myself a certain way. And, I think it defines a fair amount of us. I’d like us to take this on as a bigger platform than just some of us.”

I would pitch it to the leadership team to adopt with the business case. Some companies, if they’re not purposeful already, then they probably have some other motive to run the business. But I think I would try to make the business case of why this helps with the branding of the company or why it helps with client retention. The people in leadership positions may not be thinking that way, and even if they don’t 100% get there but still do it under the guise of ‘this is good for the success of the company,’ that’s still a good way to do it. I think once you’ve done that, good leaders will look at that and say, “I like what they’re doing and now they’ve proposed something.”

In 2019, it’s hard to ignore the voice of a team member. When we were doing this 20 years ago, we felt we were a real open company: very different, very employee-centric. Today, I don’t know that you could run a company and not have an open mind that listens to those types of things. You’re not going to get what you want every time. It could be that you do all that and they just reject that principle or that culture or whatever. In that case, my advice would be, go find a different place to work. Unemployment is low, and I believe workers are currently in the power position.

It’s not 1950 where the employer held all the cards. Today it’s the worker, and exercising that power and that right to work wherever you want to work is absolutely within reach. I would say at Tribridge, when we first started, it was all tech hiring – and then after that, it was all culture hiring. We can teach tech, but culture’s harder to teach because some of it is just DNA. If somebody doesn’t want to serve others, they’re not going to do it just because.

Service – I never knew what that word meant. I was about as ignorant as you could be graduating from college, but I worked at Arthur Andersen and we had a partner that would talk about that all the time. Actually, I remember looking the word up and thinking “Oh, this is cool. I feel this.” And once you feel it, you’re like, “I’m going to keep doing this.” And first you do it in charities and you do it in not-for-profits, but when the organization lets you do it and it becomes part of everything you do, there’s magic that happens.

I’ve always felt like you could take any team of people that were purposeful and mission-oriented and you could accomplish anything, because there’s a big difference between passion and drive, and people will talk about how you need to be driven, and there’s truth to that, but I’d much rather have passion. Drive is a means to an end – being pumped about the ‘what.’ Passion will get you through anything, and passion and purpose are so connected.

Full Stack Talent Tampa Bay Tech Leaders - Passion

When you’re feeling the purpose, your passion is high, you’ll knock any wall down, you’ll do anything because you have a real purpose to get somewhere. I think passion drives drive, but drive does not drive passion, if you follow me. I don’t care what the business is: dry cleaning, making tires, building technology, running the White House – it doesn’t matter. If you have passion, everything’s good. That’s where success comes from. It’s not about the book stuff, it’s not about strategy, it’s not about capital. Yes, you need all those things, they’re ingredients – but the secret sauce is what we’re talking about.

On Think Big For Kids

Roxanne: Think Big for Kids. Can you tell us what inspired you to start that organization?

Tony: Currently, Think Big for Kids is a program inside the Boys and Girls Club. It was started by several of us at Tribridge. I personally have been volunteering and doing things with the Boys and Girls Club for 30 years.

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders - Relate

So, volunteering time, we put computer labs in every Boys and Girls Club over about a 10-year period. We did that through Tampa Bay Tech when I was on that board. That evolved to Tribridge taking a position where we were helping the high school kids get ready for the workforce. We were doing this on a national basis, in other cities where Tribridge had offices, and one of the things I would do to participate is go from club to club and I’d tell my story. I came from a very rough beginning of my life and certainly economically depressed, lived in poverty my whole childhood, lived in 15 homes. In other words, I can relate to those kids.

I would go into a Boys and Girls Club, tell my story, and then kind of give them a path to where I thought they could have a productive post-high school life. I was doing this for a couple of years and thought we were doing great stuff until I was in South Florida and I was at a pretty impressive Boys and Girls Club. So I’m down there, and I have probably 100 teens at this club, and I remember being about two thirds through a 40-minute presentation, I’m pretty fiery, and I’m telling my story, how nobody cares you’re poor, nobody cares what your dad does. I get into this whole ‘take charge of your life, make good choices, here are the things you can do, here’s what’s in front of you’ thing and I look up, and I didn’t feel that smile that I had normally felt.

So, I stopped and I don’t know why it hit me, but I asked the question I probably should’ve asked the year prior: “How many of you in the room actually have a plan for after high school?” Of course, nobody raised their hand. I’m like, “Okay. Let me rephrase that. How many of you guys are going to college, how many of you guys are taking the SAT, how many are going to a tech school, how many are going to a junior college?” I was just trying to get a sense of career planning at this 15, 16, 17, 18 year old group. And out of the number of kids, 3 kids raised their hand.

I remember leaving feeling like, “What the hell have I been doing for the last 25 years?” I had been helping, but had I really made a difference? In essence, I was disappointed in me, disappointed in what Tribridge was impacting. My office was a big whiteboard – the whole office was painted so I could write on the walls – so I grabbed Jennie and I said, “We’re not leaving here until we can figure out a solution to this problem.”

We sat in there and debated what we were doing, and because we had been in the Boys and Girls Club for over 20 years, we had a really good idea what could work and not, and so we developed a plan called Think Big for Kids. This starts with kids in 6th, 7th, and 8th grade.

We had, in the past, been successful bringing companies in to get kids excited about different careers. This was all about exposure. Right now, in a number of Boys and Girls Clubs, I have about 10 or 12 anchor companies like ReliaQuest, Bank of America, old Tribridge now DXC, JDP Electric, Hillsborough County Sheriff’s Office, Haneke Design, Tampa General, etc. They come into our clubs and do a hands-on monthly showcase where they’re demonstrating what a career is like. Hands-on meaning building a way up, dissecting the body, building a security program, building a website.

We give the kids a journal and we track their interests. They take an interest assessment, not a skills assessment. This is all about opening the eyes of kids that maybe aren’t getting exposure to career paths, and we’re seeing kids light up. That is working in spades. We keep attracting more and more companies to it, we keep getting more and more kids in the program. In the summer before 9th grade, the kid gets a mentor, and that mentor then says, “What do you really want to do? You’ve been in the program for 3 years now.” “I want to be a nurse.” “Okay. Well let’s start talking about what classes you should be taking and what kind of grades you need and what does that looks like.” The mentors help those kids up until 10th or 11th grade, and then we start working on internships.

Full Stack Talent Tampa Bay Tech Leaders - Kids

You see where this is going. We start working on college education, then we start working on a job. The businesses included in this program have made a commitment of dollars, time at the showcases, mentors, and then ultimately giving jobs to these kids. It’s a full program to help kids, and when I am doing it, I can really resonate with these kids because I lived it and saw everything you could imagine that’s not right with growing up in these neighborhoods. I felt this empathy and this calling and then my other side of the brain said, “I do these presentations, I’m in these CEO groups, and they’re all complaining about talent, and they’re all thinking about offshore talent.”

I’m like, what about 30% of the population that’s in poverty that never goes to college? They never get formal training, they do jobs they don’t want to do. What about the ones that become criminals? What if we could get them before all that happens and create a part of the workforce that hasn’t been developed yet? This is a business model that can sustain and change not only the lives of the kids at the Boys and Girls Club but can change communities. I pitched it to the Boys and Girls Club and they loved it. I pitched it nationally and I pitched it locally and the people loved it.

The pilot that we’ve been doing for the last 2 years has been in Tampa, but the program will go national for sure. I don’t know what else to say about it other than it’s making a difference already. Even on our worst days where I think, “That was terrible,” I watch these kids light up and I go, what I think is terrible has just changed 10 kids in the room, the way they’re thinking about the future.

In 2019, we’ll do somewhere around 60 showcases. We’re talking about maybe 15 or 20 companies coming into the kids’ lives that they never even knew existed. When I’ve talked to some of the kids, I ask them what they like. I instantly try to tell them, “Just write down things you like to do. I love to solve a puzzle, I like to eat, I like girls, I like talking. Whatever, just write it all down.” Then we sit down with them and they take an assessment.

I remember this one kid early in the program that was like, “I just love food. Everything about food. But I don’t want to be a chef, so what could I really do?” I responded, “You could be a food critic, a food broker.” He’s like, “I didn’t even know those jobs existed.” The more I talked, the more that kid was lighting up and he’s like, “Oh my God.” He was a young boy, and he was so excited about something. I was tapping in, the same thing I was tapping into at Tribridge, to somebody’s passion. Find that passion early instead of waiting until it’s too late where you’re too far down the school path.

One of the things that encouraged me even years ago is, I meet these kids and they’re like, “I want to be a doctor.” “Great. You got good grades?” “No.” “Did you ever take a biology class?” “No.” “You can’t do what you’re saying because now you’re 17 and you missed it.” So, you catch them earlier – in 6th, 7th, and 8th grade – and you can put them with a mentor and find their passion and then direct it just a little bit. It’s amazing. That’s something that’s pretty important to me and others as well. Some of the other local CEOs have jumped all over this.

On his board involvement

Matt: The interest-based assessment versus the skills assessment, I think is so cool. And especially, to pair that with all the different tech companies, is awesome. For our next question: you’re currently a board member on many different organizations, including A-LIGN. Can you tell me what your involvement is with them as a board member, and about your involvement with the Tampa Bay WaVE?

Tony: I’ve been involved with the WaVE since its founding. Linda Olson and I have been friends for 24 years, so I’ve been involved with the WaVE in many capacities. I was a board chair 8 years ago. I love what it does for the community. It really is the premiere startup organization in Tampa Bay. My current position with them is Executive Entrepreneur-in-Residence.

Matt: The Richard Munassis and Steven Fiskes of the world.

Tony: Yeah. The way I look at it is, it’s a coaching role. You have these really early stage companies, some pre-revenue, and they’re looking for help and advice. I’m always wary of giving too much advice because what worked for me at a particular company at that point in time with the staff and resources that I had, won’t necessarily work for you. I’m glad to share the story, but you’ve got to find a way to apply what I’m saying and decide whether it even makes sense or not. So, I’m never offended. I run into some people who give advice and get mad because people don’t listen. I’m actually mad if they listen too much because it just doesn’t all work. So, what the role is, is really coaching. It’s about helping companies at the WaVE progress.

I have probably met with 20 or 30 companies this year. Some I meet with pretty regularly. Occasionally, I’ll join a board. Global Safety Management was one of the companies that I met through the WaVE and wound up investing in and joining the board. Other companies, I just meet on a more regular basis. Scott Conlon’s one of the guys I meet with. I don’t know if you guys know Scott.

Roxanne: That name is really familiar.

Matt: Which company?

Tony: MyArea Network. I mean, that company’s incredible. Super excited about that. I meet with them on a very regular basis. So, you wind up interacting with them, and sometimes it’s scheduled, and sometimes it’s “Hey, I have a very specific issue,” and I try to tell a story that’s related to it and like I said, usually they send me a note back, “It worked.” Or, “It didn’t work.” Or, “You’re an idiot.”

But in all cases, I kind of feel like I’m helping a tiny bit. I love that. I love doing stuff with the WaVE, love it, love it, love it in every way imaginable. We just put together a high-level advisory board too – not the normal corporate board – with a number of folks like Steve Raymond, Chuck Sikes, and Tom Wallace. We kicked that off recently to give the WaVE another sounding board on a strategic level.

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders - WaVE

The WaVE, to me, is necessary. Alex Sink is the current chair, and she’s dynamite, if you don’t know her. Linda’s been there forever. I feel like it’s one of those necessary parts of our ecosystem that’s feeding this whole area with new companies and helping them to the next stage.

Roxanne: What about A-LIGN?

Tony: So, A-LIGN is one of the companies – I think you guys have interviewed Scott before.

Roxanne: Yeah, he was one of our first!

Tony: Yeah! I’ve known Scott Price for probably 25 years, when I was at Arthur Andersen. He was at Arthur Andersen and our kids went to the same school for a while so we definitely know each other. And Scott’s done a great job building his company. They recently got funded by a private equity firm for some financing, FTV Capital.

Between FTV, Scott, and I, with the new relationship he had and my experience with both private equity and fast growth companies, all parties thought, man, this would be a good way for Scott to have a sounding board and somebody on the board that isn’t a private equity firm but that had been through it before. I’ve played this role before: really helping the CEO figure out that transition from small private board to a PE-backed board, and also help him on the journey from their current revenue level to greater than 100 million.

They’re growing fast and frankly, I’m not sure Scott really needs me, but I love him. He’s an impressive guy, and the business is doing well. I have a fiduciary responsibility as a board member. When I’m not doing that, I’m doing what I would call CEO coaching, like I’m doing at the WaVE, but on different problems. More what I would call high-class problems, like we’re growing really fast. It’s really good.

Matt: Good problems to have.

Tony: Yeah. Scott has the best problems.

Roxanne: You mentioned Arthur Andersen. That means you probably know Jeff Alagood and all the guys at–

Tony: Oh yeah, very well. Dave Romine. I’m friends with both of those guys, love AgileThought. I think you just did Jeff about a month or two ago.

Roxanne: He was probably my favorite one so far. He gave us a whole huge tour of the office, spent about 2 hours with us. We love him and his sea turtle story.

Tony: He is a solid community guy. It’s so obvious in all the stuff he does, and the same with the other guys here. So, I’m a big fan of theirs.

On his involvement in the tech community

Roxanne: Other than the WaVE right now, are you still involved with the tech community?

Tony: I am. I’m on the board of a number of tech companies. Global Safety Management, CCG Analytics, CFO Alliance. Additionally, I’m involved in a strategic advisory role with Tampa Bay Tech. And, I’m very involved with Florida Funders on the investment side, both as an investor but also just helping them as they grow, and very close with the leadership there. Tom Wallace was our seed capital in our business. I also spend some time with Rachel Fineman at the Israel business accelerator and I love what they’re doing there.

Talent in Tampa

Matt: Over your 19 years at Tribridge and your overall time in Tampa, have you noticed a positive shift in terms of the quality of your tech talent in the more recent years?

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders - Tech Talent

Tony: For me, I’ve been in the market for over 30 years, and we started Tampa Bay Tech almost 20 years ago now. It was a very small tech community here, very small. When I look at 20 years of growth, the number of companies that are doing tech, the number of entrepreneurs, the dollars of capital invested, the tech talent is 10 times what it once was. It’s crazy. People that were in middle school when I started Tribridge are now starting companies around tech.

I’m super bullish on Tampa in the tech world and probably have a different opinion than some of the area pundits on it. In truth, I think we’re much further along than people say. It’s more spread out here. There are a lot of things going on that go undetected and I don’t think we do a great job marketing. There’s a ton of tech talent here. And I also don’t think it matters. Look, I’m not one of those guys who thinks all the talent needs to live in one city. We had a company for 20 years that, yeah, we had a lot of people in Tampa, but we were getting talent everywhere in every state, and they were working as part of Tribridge.

If you build a great culture, people will want to work for you. And the way we all work today, it’s all distributed anyway. You don’t need to all be in the same room. There’s so much technology to help tech companies develop without being in the same room, so we continue to find our market by the geography of Tampa and saying there’s only X amount of talent here. Really? Well, why can’t we recruit outside of Hillsborough, Pinellas, and Pasco counties?

That’s a strange mindset to me because I’ve never thought that way. I think we really need to be continuing to attract talent to Tampa if we want them to live here. But why do we care where they live? We just want them working for companies that are headquartered here, where our entrepreneurs are. Let the tech talent be the world, let it be international, let it be in Israel, let it be in Russia, let it be in California, who cares?

Roxanne: The problem with that, and it might not even be a problem for some people, is that it goes both ways.

Tony: Yeah.

Roxanne: My partner is a Senior DevOps Engineer here. He used to work in Tampa but he got a job working for a company in New York making significantly more money than he was able to make in Tampa.

Tony: Well if we’re going to compete for tech talent on a global basis, we’re going to have to pay. I have no problem with that. That’s just part of the game.

Roxanne: And that is the one thing Tampa is lagging a little bit behind on the national average.

Tony: The wages? Yeah. You know better than I do. I’m not even going to debate that. However, in the whole time we had Tribridge, I never felt like we lacked talented technical resources. And inside of Tribridge, we had a software company, we had a cloud company, and we had a tech services company. We had every type of tech talent you might want to have, from cloud engineers to software developers to business functional analysts. And yeah, it was hard. I’m not saying it’s not hard to get talent, but that’s true for everybody.

In Cincinnati, Boston, and New York, everybody’s saying the same thing. So, to me, why would you not want to be part of this? This is awesome. It’s a growing tech community, it’s super tight, people around here respect each other. This is the most collaborative city, and the most entrepreneurial city I’ve ever been associated with. I’d rather live here, be part of this, than anywhere else. Why can’t we sell that to a young person that is getting involved in tech that wants to join a company?

Tony DiBenedetto - Full Stack Talent Tampa Bay Tech Leaders - Tampa

I think we’re terrible at marketing. We don’t market ourselves well as a community, but that’s changing. I think people like the folks at Synapse, Florida Funders, the WaVE, and TBT are doing a better job of that. The brand of the Bay area, not Tampa, but the Bay area, is not exactly what the reality is. So, I’d rather have that than the reverse. We just need to up the dollars and up the creativeness and start doing some smart things on advertising and branding our area.

I don’t know why we don’t brand around the concept of being one of the best tech entrepreneurial cities in the world. We are. We have to stop saying, “Well, we have to get to the same level as Austin and all these other tech hub cities.” They’re different. They have their own story. Our story is phenomenal. I don’t like the people that say, “We’re not this.” We’re Tampa Bay. Of course, we’re not this. We don’t want to be this. We want to be Tampa Bay.

What Tampa can improve

Matt: You said that you feel a little bit different with the state of where we are, so where do you hope to see us come through in the next couple of years? What are the places that you think we should improve, and short term goals we should set?

Tony: We still don’t have enough capital here. I mean, Florida Funders is doing great. But I want to see 10 Florida Funders. I still believe we’re missing early stage capital. Growth capital, you can get anywhere. If you’re a growth company that passes a certain stage, you’ll attract private equity venture firms from all over the world. I’m not worried about that. But the earlier stage stuff, we just don’t have enough capital. So, Florida Funders X10. That’s what I want to see.

The other thing I want to start seeing out of the class of companies that have started here in the last 10 years is a billion dollar company. I think we’re capable of it. When I look at what happened with myMatrixx, where he got, where Tribridge got, and where some of these other ones got. I’d like–

Roxanne: myMatrixx was 480 million?

Tony: That was the exit. I wasn’t even thinking exit, I was thinking revenue. To me, instead of companies even like Tribridge selling to a strategic, why are we not the strategic? Why are we not the destination of those companies? Be the acquirer, not the acquired. That will be a sign that things have shifted – when that company that buys those companies all over the world is headquartered here.

Words of wisdom for tech newbies

Roxanne: Do you have any advice for people looking to get into tech as a career? What’s something that a new grad could do to make themselves more attractive to companies? Especially the ones missing that crucial 2 to 4 years of experience.

Tony: Everything for me around life and job centers around the word passion. I’d go back to that since we talked about that already. My biggest piece of advice is find things you love to do. It’s ‘what am I personally passionate about and how do I create a career or a job that feeds that passion?’ After that, when you think about inside the world of tech because tech’s so ever-changing, it’s doing a good job of reading about what’s going on in AI or virtual reality or robotics or you name the tech discipline.

I think you’ve got to read a lot to see what’s even possible. Like we said with Think Big for Kids, for young adults, knowing all the possibilities is hard to do. It’s really reading and networking enough to go, “I didn’t even know that was possible.” And then, it’s all about investing the time and the learning.

Full Stack Talent Tampa Bay Tech Leaders - Learning

Once you know what you’re passionate about, once you know it’s possible, build your skills and your career by just being a lifelong learner. I’m still reading, learning, getting into new things. I’m 53, and I feel stupid still. Honestly, I don’t feel like I know anything. The more you can get exposed to things and talk to people and meet young people like you guys and go, “Oh, that’s pretty cool,” the better. Be that curious cat. When I meet people that are 25 or 30 years old and they’re not curious anymore, it’s such a turn off for me. I’m like, I don’t know anything, how the hell do you know anything? It just blows my mind. And sometimes that’s just personality type, but to me, I think you can force yourself to be more curious.

One city

Matt: Before we get to the last question, something I was curious about, outside of technology – what’s something you hope to see in the next couple of years? Maybe outside of even general business as far as the greater barrier of the Bay area.

Tony: One of the things we are progressing on is where it is Tampa, St. Pete, and it’s one. I still think of this as one place, Tampa Bay. When I drive over a bridge, I don’t think I’m in another place. I’d love to continue to see the progress that’s been laid by the prior mayors. And, I’d love to see us do more joint development things like when you talk about sports teams or when you talk about museums or whatever and just get rid of the competition and just really be a region.

Specifically, I’d like to elevate this area as a power region, because I think that’ll help all things. I’m a big fan of collaborative competitiveness. I like when people work together to figure something out versus false boundaries that we have with geography or ‘you work at this company, I work at this company.’ In fact, I worked very closely with a number of competitors for the last 20 years to learn the market and build products and be customers of other competitors. I just think that’s a more powerful way to go to market.

This whole area needs that next level. It starts with the people we vote for, whether it’s House of Representatives, whether it’s governors, whether it’s local mayors. I think we need to pick people that are more collaborative instead of trying to compete. And we should not let the Rays go anywhere, and we should support the Lightning. If you’re not a sports fan and you don’t realize the economic impact of a sports team, the profile that a sports team brings, the jobs that they create, the elevation of a city when you win a little bit as a sports team. It’s just, it changes the game.

Final thoughts

Roxanne: Last question! Anything exciting coming down the pipeline for yourself or any of your projects?

Tony: I like how much I’m doing in the community, I love the local scene. And, I love being in this coaching phase of my life for now. I’ve only been doing this for about 15 months, but right now, I would say I’ve never been happier as a person in my personal life and my work life. I’m not going to mess that up. Now, we know it’s going to happen, stuff happens. But for now, I feel like I’m on the right boat.

About Tony DiBenedetto:

A 30-year executive, serial entrepreneur and thought leader, Tony DiBenedetto is the former CEO of technology company Tribridge, where he led the strategic direction, development, and vision for 19 years. He also served as CEO of Concerto Cloud Services, a subsidiary of Tribridge. He is currently Executive Entrepreneur-in-Residence for Tampa Bay WaVE and on the board of several fast-growing companies.

Tony co-founded Tribridge in 1998 and led the company through the acquisition and integration of several companies, resulting in a compounded annual growth rate of over 40 percent each year. He was most recently recognized with the Community Dedication and Leadership Award by Tampa Bay Tech and named among the Top 25 Technology Disrupters in the country by CRN magazine.

Tony is the founder of Think Big for Kids, the premiere teen initiative of Boys & Girls Clubs of Tampa Bay. It helps underprivileged youth ages 12-18 discover their untapped potential by bringing them highly structured education, mentorship and career path development. Think Big for Kids partners with like-minded organizations representing diverse industries to reduce systemic poverty and prepare kids to excel in high-demand professions of the future workforce.

Roxanne Williams is the Marketing Director at Full Stack Talent, a technology staffing agency in Tampa, FL. Find her LinkedIn here.

Want to nominate a tech leader for us to interview? Fill out the form below!