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Posted By Megan Holmes


In many ways, Tony DiBenedetto's endeavors have been at the center of the gravitational pull that has made Tampa Bay what it is today, a thriving entrepreneurial ecosystem. As CEO of Tribridge, DiBenedetto was at the helm of building a multi-million dollar business that changed the story about what homegrown Tampa Bay companies could do. Now, alongside his numerous positions on boards of tech companies throughout the region, DiBenedetto has turned his attention to larger problems, like the shortage of tech talent and the opportunity gap for socio-economically disadvantaged kids. Connecting those two problems led him to founding Think Big For Kids, a nonprofit endeavor connecting kids to their very first jobs in Tampa Bay.

Years in St. Pete

since 1987.

Organizations involved in

Think Big for Kids, Tampa Bay Wave, Florida Funders. I’m on the boards of A-LIGN, CFO Alliances, CCG Analytics, My Area Network, and Global Safety Management.

What gets you out of bed every day?

Close to 15 years ago, there was a young lady that worked with us, her name was Cindy Rawls. She wanted me to come speak to the local rotary club of Lakeland. And I was like “What do you want me to talk about?” And she was like, “Just tell you’re story.” So I did. In the first 5 minutes I started telling my story, I was visibly crying. And I, for whatever reason, never had been emotional and never told my personal story. So after this event, what I realized that got me up in the morning is that I really love helping people. Once that clicked in my brain, I felt way more comfortable telling that story, but also felt comfortable about why I was here. I get really jazzed up when I feel like I can impact somebody else’s life in a positive way. That gets me up in the morning.

Why St. Pete?

*Tampa Bay.

I got a job at Arthur Anderson. I had never been – not one day – in Tampa or the bay area at all. I came originally for the job but the reason I stayed is way more complex than that. Raising a family here is phenomenal. For me, raising a family has been very easy and rewarding here. I’ve raised two girls here. But the business community here has really evolved into this super collaborative entrepreneurial place that you can not only start businesses but grow businesses into something special. And you’re not by yourself. It’s like one big community and people helping people remove obstacles to their success. That, to me, fits my whole purpose of being.

What is one habit that you keep?

Personal habit: Meditation. It’s funny because I remember having a lot of stress maybe 25 years ago so I went to a therapist, and they said, “What you really need to do is learn how to breathe.” So I started with that. And then over the years as the jobs got bigger, the stress got bigger, et cetera, people started saying, “You really should meditate.” Which is not a compliment on the surface … I started doing meditations online through an app and that really changed my whole mental profile. I really got better at handling the stress, better at taking myself as a high energy person and refocusing that energy. I try to meditate every day.

Business habit: Getting better is more important than being perfect. Sometimes you get around folks that are waiting to implement change or make a move when all of the ducks are aligned. My personality but also my witness to success on how this works is that I’ve found it much better to act on what you thought the right thing is and make continuous improvement. What I have found over time is getting people out of their own way and getting them to act and make improvements on a regular basis works.

Who are some people that influence you?

When I talk about how great Tampa Bay is, part of that is some of my influences are local. Of the people locally that have been hand in hand with me and have had a big influence and a material impact to my trajectory and my success, I’d start with Tom Wallace. Everything from his leadership, his thought process, the way he grew a company, his straight talk, his care for people. I felt myself gravitating towards a lot of things he was showing me, teaching me and everything I was witnessing of him. The other person I’d point to is George Gordon, who was with Tampa Bay Technology Forum. The thing I got out of George is leadership. The way he led people, the way he communicated leadership, the way he interacted with folks. Whatever they taught him in the Navy, he carried forward for many years after and passed it on to people like myself.

What is one piece of insight - a book, methodology, practice - that you would share with our readers?

Two books that I think have shaped the way I think and I’d like to pass forward. One is an old book called Good to Great, which I’m sure lots of people have read. The thing in Good to Great that was the most profound to me was get the right people on the bus, put the right people in the right seats, and get people off the bus that aren’t a good fit. It’s all about everybody being on board with what the vision is and everybody being able to row the boat together and produce together. More recently, there’s a guy named James Hunter who wrote a book called The Servant. What servant leadership turned out to be in this book and I think in others, is all about loving people. What happens is you build a culture of people that are givers and those people in turn give their best and work together to accomplish the mission.

What is one thing you wish you knew about your work 3 years ago?

“What is one thing you wish you would have known about Tribridge three years before you sold it?”

I’m not a big fan of regret so I can’t say that. But in terms of knowledge we’d all like to know what’s going to happen 3 years from now. I think the big thing is that the market shifted pretty dramatically to SAAS and Cloud. Which we thought was happening but it shifted even faster in the 3 years since I’ve sold Tribridge. That new set of economic conditions probably could have meant a different outcome for lots of people but also just changed the trajectory of the company. I also thought that Tribridge was going to grow to a billion dollars in revenue. We changed gears in the middle of our process to get new capital because we had a strategic buyer at the right time convince us this was the right path. I think if I knew what the next three years was going to be, we could have turned that offer down and taken a lesser offer, and taken a different path.

What’s next?

The real big thing for me in terms of what I want to spend more of my time on, is to help Think Big For Kids continue to grow and serve kids in the bay area that live in tough economic conditions with that transition from being a middle schooler to getting your first job. Today, we’re serving 750 kids in the bay area. Hope to be serving 2000 kids by 2022.

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