TBBJ Article: Tony DiBenedetto’s mission to break the poverty cycle through career mentorship nonprofit

Tony DiBenedetto spent two decades building a major technology company in Tampa. But in 2016, just before the sale of Tribridge in 2017, he had an epiphany.

“I grew up in poverty and so as an adult, had been giving back in that community,” DiBenedetto said. “I was speaking at a Boys and Girls Club in Miami, [when] I realized the kinds of kids that we had been helping, both at [Tampa Bay Tech] and at Tribridge, had all been outspoken, good students. But the majority of the kids aren’t outspoken, they’re shy, or they think I’m only talking about tech jobs. Who’s helping them?”

Realizing that he’d have “a lot of time on [his] hands post-sale,” DiBenedetto said he wanted to use everything he’d done in the past to create a bigger program—one that helped young, underrepresented kids break the cycle.

“So many people … draw conclusions that somehow people choose [poverty] in a weird way or earn it,” DiBenedetto said. “We try to point out that kids that are born into poverty didn’t earn anything. They’re just born into poverty through the circumstances of their parents, and they’re really starting with one foot backward.”

After pitching the original deck to the Boys and Girls Clubs of America CEO, who suggested running a pilot program in Tampa, in the fall of 2017, two middle school clubs locally launched with 80 kids.

By early 2018 — after Tribridge sold as one of the largest privately-owned companies in Tampa Bay — DiBenedetto was self-funding five clubs to support 500 kids in what is now Think Big for Kids.

“We hired [Amy Alley, TBFK’s executive director] with 500 kids, with the idea we get to 2,000 kids by 2022,” DiBenedetto said. “Of course, now we’re at 8,000 kids. So, it’s been a home run.”

Officially launching in 2019, the nonprofit is designed to unlock underprivileged students’ potential through career exploration, mentorship and job readiness programs.

DiBenedetto said the name stems from an annual three-day seminar Tribridge held for employees globally to motivate them and encourage them to think bigger about “tri-bridging” their careers.

Breaking down impact

Guiding students through three key stages to prepare them for successful Think Big for Kids founder Tony Benedetto with a 2024 scholarship recipient. JAMES OSTRAND careers begins in middle school (grades 6-8), where students explore diverse career paths through presentations from local companies across various industries.

By the end of eighth grade, students are paired with a mentor who supports them throughout high school and beyond, where the job readiness and placement stage provide guidance until they secure their first job.

The organization expects to reach 10,000 kids later this year. The next goal? Honing in on impact.

“I think you’ll see us shift to really measuring how many of our kids have grown up and are earning a livable wage versus how many kids are still struggling,” DiBenedetto said. “I also think you’ll see our partner companies hiring more of our kids because they’ve now been through college or through tech school.”

The nonprofit, entering its sixth year in 2025, has locations in six other cities. Expansion began in 2021 in locations like Chicago and Atlanta, and DiBenedetto doesn’t rule out the possibility of more.

“We’ve been asked to take this internationally, in Europe and other places. I don’t think we’ll do that just because we have limited resources, but because we’ve been successful, people are willing to invest money,” DiBenedetto said. “We’re trying to grow responsibly, like I’ve been doing with other ventures, which is something that you’ll see the second half of the decade.”

Since launching the nonprofit, DiBenedetto has remained on the board. In 2022, he stepped back into the ring as CEO of Dallas-based Appspace.

“I initially was not intending to go back into a CEO role because I was really happy with board roles,” DiBenedetto said. “The balance is hard because I’m so passionate about the kids … but the investors in our company and the people in our company knew that this was important to me, and I wasn’t going to give up Think Big to take on the role as CEO.”

In February, DiBenedetto was announced as a Horatio Alger Award recipient. The award annually recognizes 12 individuals across the country who have overcome adversity to achieve success while demonstrating leadership, integrity and a commitment to philanthropy.

“[Think Big] is good for all of us. You don’t have to have the biggest part to be involved, it could just be about making your community better,” DiBenedetto said. “But part of being better is having stronger citizens that can do more and be more capable of taking care of themselves. Obviously, we have a bigger purpose than that, but it can be that simple.”

Check out the article here, written by Anjelica Rubin – Technology/Tampa Bay Inno reporter, Tampa Bay Business Journal.