Tony DiBenedetto

Tony DiBenedetto has come a long way from his beginning, but his story reveals the power of resilience and self-reliance in the face of difficult circumstances. His mother was a teenager and drug addict when he was born in Brooklyn in 1965. “My mother was too young for motherhood and she hung out with the wrong crowd,” DiBenedetto says. “She just couldn’t handle her situation.”

DiBenedetto’s Sicilian immigrant grandparents took over his care when he was two years old. “My mother was the oldest of their children. She became involved with a criminal element and one day, when I was nearly eight, the front of our house was sprayed with bullets. That night, my grandfather took us out of the house. We didn’t tell anyone we were leaving or where we were going. We moved to Fort Lauderdale, Florida, but my mother stayed in Brooklyn.”

DiBenedetto’s grandparents were poor. His grandfather, who only had a third-grade education, did manual labor. His grandmother became his main source of support. She was loving and he fondly remembers the Italian cooking lessons she gave him. “My grandmother was grounded,” he says. “She had a big heart and was very generous. We had no money, but every Sunday we had a house full of people for a simple dinner. She never turned anyone away.”

When DiBenedetto was 12, his grandmother had a fatal heart attack. “That’s when my world really changed,” he says. “My grandfather became disoriented and unable to keep me. I lived with my mother for a month, but nothing had changed with her. She was still a heavy drug user and involved with criminals. It was common for police to be at our house. I knew I couldn’t stay, so that’s when I decided to go live with a friend.”

DiBenedetto spent a summer with John Lillie, who was a mechanic. “He was a long-time family friend. John let me sleep on his couch, and in return I cooked for him. I was only there for a few months, but John had a significant influence on my life. He was the first person to tell me I didn’t have to let my circumstances dictate my life. He often told me I was smart. John was a confidence builder.”

For the next year, DiBenedetto’s grandfather rallied enough for him to live with him again, but by the ninth grade, he left his grandson and moved to Pennsylvania. From that point until his high school graduation, DiBenedetto lived as a drifter. He slept on couches, he shared space in a garage, and he lived with high school friends’ families. By the time he was a senior, he believes he lived in 15 different homes. “I lived in very diverse neighborhoods,” he says. “I was constantly having to adjust to different situations.”

During his senior year, DiBenedetto’s guidance counselors nominated him for a number of college scholarships. “These were local scholarships that altogether amounted to only $500, but I was very grateful for them. I told myself to remember the generosity of others. The people I stayed with throughout my high school years were mostly poor, but they shared their space with me. It all meant so much to me, and I knew that as soon as I was able, I would find ways to help others.”

DiBenedetto was thrilled when an anonymous donor gave him a full ride scholarship. He was accepted at Florida State University (FSU), but within days of moving into his dorm, he was told that the donor could no longer honor his commitment. Undeterred by this bad news, DiBenedetto knew that he would work his way through the problem—just as he had always done in the past. “I knew the playbook,” he says. “You work hard and you move forward.”

DiBenedetto took a work study job, where at the Career Center he met his next mentor, Pearly Rosier. “During my high school years, I was exposed to many different families but I was never parented. I was pretty aggressive with authority, but Pearly taught me what I should’ve learned when I was a kid. She taught me manners and was a coach for how to be successful in life. My grades as a freshman were poor because I was working 40 to 50 hours a week. Pearly taught me to respect myself and my education.”

DiBenedetto learned to balance his work with his studies, which quickly improved his grades. His work at the Career Center resulted in his development of a groundbreaking software application to monitor companies recruiting college students. In 1987, DiBenedetto graduated with a degree in business management information systems and was recruited by Arthur Andersen.

By the time he was 33, DiBenedetto became one of the firm’s youngest partners. He enjoyed his work, but after 10 years, he felt it was time to start a company of his own. In 1998, DiBenedetto co-founded Tribridge, a Tampa Bay-based technology company, where he served as CEO until its sale in 2017. By then, the company had nearly 1,000 employees across North America and Europe and annual sales of $175 million.

During his career as a CEO, DiBenedetto discovered he enjoyed advising other new start-up CEOs. “I make a better coach than player,” he says. “After selling my company, I joined several tech boards and spent a lot of time giving advice to young entrepreneurs.”

Today, DiBenedetto serves as chairman and CEO of Appspace, a workplace experience platform that specializes in connecting people, places and spaces. He leads strategic direction and drives the overall vision for the global organization. More than one-third of Fortune 500 companies use Appspace software solutions for their distributed global workforces.

DiBenedetto is also the founder and chair of Think Big for Kids, a national nonprofit with a mission to break the cycle of poverty by providing middle and high school students with career exploration, mentorship, job readiness, and placement to excel in today’s workforce. Since its inception in 2016, Think Big for Kids has helped more than 8,000 young people set and achieve their post-high school goals. “I always wanted to give back to the community that gave so much help to me,” he says. “I think I’m doing that with this program.”

DiBenedetto is the recipient of numerous leadership awards, including the Ernst & Young Florida Entrepreneur of the Year® Award in Technology and induction into the FSU College of Business Hall of Fame. He was also recognized with the Community Dedication and Leadership Award by Tampa Bay Tech. He was named Philanthropist of the Year by Tampa Bay Business & Wealth magazine, and Tampa Bay Business Journal voted him to the Power 100 List for three consecutive years and most recently as a Legend in the Business Community for his enduring impact.

In 2024, DiBenedetto made a $1 million endowment to his alma mater, Florida State University’s College of Business, to support first-generation college students. He is involved in many community organizations, including the Boys & Girls Clubs, United Way Suncoast, Tampa Bay Tech, and Tampa Bay Wave.

DiBenedetto had a challenging childhood, but he has become comfortable with sharing his story—especially with the young participants of his Think Big for Kids program. “I think my story taught me some important life lessons,” he says. “When I give advice to young people who are faced with adversity, I tell them they need to be purposeful about their life. They have to decide what they want and then they have to be relentless about pursuing that dream. If it’s something that requires education, then get the education. I also think it’s important to help others. Be the one who volunteers, be the one who listens, and be the one who tries to understand. The third part of my advice is to never stop trying to improve yourself. Be a lifelong learner.”

Surprised and humbled by his Horatio Alger Award, DiBenedetto says, “The Association is creating a path of hope for young people who don’t think they have a way forward. By sharing stories like mine with them, we are telling them that in America there is always hope. There is always a way forward. It takes hard work and determination, but the dream is there for all of us. You just have to believe in yourself.”