Growing up, Tony DiBenedetto experienced firsthand what the common phrase “it takes a village” really means.
At a young age, DiBenedetto found himself, essentially, caring for himself. When others his age were planning for homecoming he was couchsurfing, grateful for a place to sleep.
He was, what he describes, a little “rough around the edges.” Understandably so.
Thanks to some notable people who entered at different stages in his life, he says that the community was his family.
It’s fairly easy to draw the conclusion that DiBenedetto’s most recent passion project, Think Big for Kids, is something born from his own experience and a way to come to terms with some of his own traumas.
Think Big for Kids is a nonprofit that helps underprivileged youth discover untapped potential through three programming pillars: career exploration, mentoring and job readiness and job placement.
The former CEO of Tribridge, a major technology company in Tampa which sold in 2017 for $165 million, now has more time for giving back and he has big plans to expand the reach of the mission with Think Big for Kids going national, launching in Dallas, Atlanta and Chicago this fall.
ONCE UPON A TIME IN BROOKLYN
DiBenedetto was born to parents who weren’t even truly adults themselves at the time. He says his mother had an addiction to drugs and his father wasn’t around.
He was raised, mostly, by his grandparents in Brooklyn, New York during his early life and he had a particularly close bond with his grandmother.
“My grandmother was a traditional, Italian grandmother,” DiBenedetto says. “She was the heart and soul of the whole family. I always feel when someone says to me ‘you have a good heart,’ that is from my grandmother.”
It’s important to note, this was not the trendy, hipster-filled Brooklyn that might come to mind today. It was enveloped in crime and drugs.
“When you’re a kid, you’re in the situation you’re in. You don’t know any differently,” he says, acknowledging his working-class childhood.
A domestic violence incident at the family’s home, when DiBenedetto was about 8, led to the family relocating to Fort Lauderdale. About four years following the move to Florida, DiBenedetto was rocked by the death of his grandmother. Recalling the memory visibly makes DiBenedetto emotional.
“My grandmother was my mom,” he says. “To be honest with you, up to that point, I would have said I had a great childhood. We were poor and my grandfather did odd jobs, even after we moved to Fort Lauderdale. We got our hair cut at Kmart, wore crappy clothes and, at times, we were on welfare and food stamps. I was just never embarrassed by it.”
DiBenedetto’s grandmother was the glue that held the family together and after she died, drug deals and other dangerous activities quickly became the norm at home. It was clear his grandfather, and other relatives, weren’t capable of parenting.
From the age of 12 into young adulthood, DiBenedetto lived with more than a dozen different people. One person was named “John.” DiBenedetto leaves his last name out purposely to protect his privacy.
It was the summer between seventh and eighth grades.
“I agreed to cook for him, so my early cooking interests, besides my grandmother teaching me how, was cooking for him as my rent,” he says. “It wasn’t an ultimatum. But it was good because he gave me a responsibility.”
“He told me, ‘You don’t have to be like your family,’” DiBenedetto recalls. “He also said, ‘Look, you’re a really smart kid. You’re good at math. You should get into computers.’”
At the time, there were no computers in schools. It was 1977.
“The whole school knew I had no one at home looking out for me. I was a ward of the community, instead of the state. The principal knew, the guidance counselors knew. But I got good grades, I took tough classes and they let me not have a guardian. I would check myself into school. I answered for myself at a really young age. In a weird way, it was a great skill,” he says.
He lived with a lot of different people. Even in households that spoke Spanish and German, just to name a few.
“It shaped my ability to get along with pretty much any person and also being able to communicate with people differently,” he says. “I genuinely like people and I think it’s from living in all of these different places.”
Nearing the end of high school, DiBenedetto had a major moment that directly ties into his passion behind Think Big for Kids.
The high school awarded him multiple awards and scholarships, most of them small tokens of his achievements. But the big one was a scholarship from a local high school booster to attend Cornell University to play baseball.
He notes, while he never did end up attending Cornell, it was the intent behind the gesture that impacted him profoundly.
“That night, I vividly remember saying to myself, ‘wow look at what all these people have done for me. I must make sure to pay it back.’ It was an impactful night,” he says.
THE ROAD TO TAMPA
Entering his young adult years, DiBenedetto decided to go to Florida State University, a much more affordable option than out-of-state Cornell.
When he arrived, and was set to start taking classes, he learned that his scholarship fell through.
“So, I started working, which was a great thing,” he says. “I worked in the disabled student lab. My first week on campus I met a guy named Jeff Douglas, an African American guy, a quadriplegic. He was an unbelievable influence on me…he taught me a ton about people.”
It was hard to feel sorry for himself, and his own challenges, in the presence of someone like Douglas, DiBenedetto recalls.
“I remember feeling like there’s nothing that’s in my way,” he says.
DiBenedetto also met Pearl, another mother figure, who is still present in his life today.
“As much as there was all this abandonment from my family, I had people in the community pick me up along the way,” he says.
After college, DiBenedetto began working for Arthur Andersen, formerly one of the “Big 5” accounting firms, in the Tampa office. At a relatively young age of 32, he was named partner at the firm.
“But the whole time, wanting to start a company was nagging at me,” he says.
He did just that. He opened a pizza and bagel place in South Tampa.
“It was one of those moments where you realize you don’t know [expletive],” he says with a laugh. “I went and studied with this guy in Brooklyn to learn how to make a Brooklyn bagel. It’s all about the water. It’s always about the water.”
He ran that place for about a year, while working at Arthur Andersen.
“I learned two things out of that [experience]. One, you can always nail cost in any business. You can predict that. But the revenue, I was off by magnitudes,” he says. “The second thing I learned was about hiring people.”
He refers to the challenges in finding dependable people who you can rely on. The nights when a delivery worker didn’t show up meant DiBenedetto was running food to homes, only to have to be up and wearing his Arthur Andersen suit again in the morning.
He was killing himself, and it wasn’t worth it.
The next monumental moment he brings up is meeting Tom Wallace, managing partner at Florida Funders.
KISSING THE RING
DiBenedetto refers to Wallace as the “godfather of technology.”
He explains this fateful meeting with Wallace as going to kiss the ring and asking for money.
“I’m 32, and Tom knew me pretty well, but you know, it was a [gutsy] ask,” DiBenedetto says.
To hear him tell the story, it does sound like a scene from Goodfellas. Smoky restaurant, gentlemen gathered to discuss business, and make deals over bourbon and cigars.
“He reads the business plan and he’s like, ‘Look, I don’t know anything about Internet or CRM [customer relationship management].’ CRM wasn’t a popular term then, like it is today, it was 1997 or early 1998,” DiBenedetto says. “Then he says, ‘But I really believe in you.’ He takes out his checkbook and writes me a check for $300,000.”
That was the birth of Tribridge, which DiBenedetto established along with his two partners Brian Deming and Mike Herdegen.
In the first year of business, the company did $2 million in revenue and $300,000 in profit.
When the company sold in 2017, the company had grown to $175 million in revenue.
“There’s a certain element of just pure, stupid confidence,” DiBenedetto says of the journey of Tribridge. “I learned something about myself running the company. I didn’t know how empathetic I am. I started feeling in a way I didn’t imagine because I was responsible for [all these people].”
A PASSION PROJECT
These days, DiBenedetto spends about half of his time mentoring, and coaching, other CEOs and on boards, and the other half on Think Big for Kids.
“I’m probably working just as much as I was before, but it feels like I’m not working at all,” he says.
Think Big for Kids was a natural progression from the work DiBenedetto was already doing with the Boys and Girls Clubs of Tampa Bay.
For about 10 years, he spent time raising funds to set up computer labs, visiting clubs and sharing his story.
It was another epiphany moment that jarred the concept for taking his work a step further with creating his own nonprofit organization. He was at a club, giving his prepared story, trying to inspire a room full of teenagers who probably would have been anywhere else in the world, if they could.
“I thought I was doing great. It was like a moment of truth. I looked up and noticed I was only connecting with a small percent of the group. It was the kids with the good grades,” he recalls, noting, he felt an instant headache come on. “I stopped in the middle and said, ‘I’m not going to talk anymore.’ So, I started asking questions. ‘How many of you are going to college after high school? How many of you know what the SATs are?’ And out of the 400 kids, I was getting three or five hands going up. And I realized, I had only been helping the upper part of the population at that time—those that didn’t necessarily need my help as much as others.”
DiBenedetto left that meeting feeling like a failure. But he let it be the catalyst for a whole new approach to reaching underrepresented, or underprivileged, youths before they gave up on a world that seemed to move by without them.
He realized, he had to get to them sooner.
“A lot of the stuff we were doing was starting with high school kids. It was a little late,” he says. “I started talking to kids differently and I realized we needed to start in the sixth grade [with outreach].”
DiBenedetto met with Chris Letsos, who used to run the Boys and Girls Club of Tampa Bay to pitch his comprehensive program that would work with kids from sixth grade through to their first job. DiBenedetto offered to fund the entire program himself.
“He lit up,” DiBenedetto says. Letsos told him that, at that time, the Boys and Girls Club was trying to change its focus more on building careers, but they weren’t sure how to go about accomplishing that goal.
“I told him, ‘Look, I can break all the rules and work outside the system,” DiBenedetto says.
After a meeting with Jim Clark, the CEO of the Boys and Girls Club of America, DiBenedetto was given the green light to implement pilot programs to test his plan.
The first two Tampa schools to implement the Think Big for Kids program was Davis Middle School and Webb Middle School.
DiBenedetto called two other local business owners to get them on board with the plan. Brian Murphy of Reliaquest and Jody Haneke of Haneke Design.
“I thought they had the right heart for it,” DiBenedetto says. “They both said yes, which was awesome because it gave me a little bit of confidence, like OK, there’s something here.”
The organization really found its stride when DiBenedetto called up Amy Alley, previously the CEO of the Tampa Bay Technology Forum, to lead Think Big for Kids as the executive director.
“When she came on board, it really took off. We went from 10 clubs to all the clubs in Hillsborough and all of the clubs in Pinellas,” he says.
Now, the Think Big for Kids programs are going national with a presence in Dallas, Atlanta and Chicago.
“It’s only been four years since we got through those two pilot programs, and only 2½ years since Amy came on board … we’re already serving 2000 kids,” he says.
“We got through COVID great,” he says. “I’m shocked by how many people have resonated with helping our kids”
A full-circle moment, for certain, for DiBenedetto and his story. ♦
Tony’s Favorite Things
BASEBALL: A favorite memory of DiBenedetto’s is doing a fantasy camp in Yankee Stadium in 2008.
COOKING: During the quarantine of 2020, he created menus for his family and has saved them to this day.
TRAVEL: He owns a home in Vail, Colo., and spends a lot of time there with his family hiking and unwinding.