Thinking big: Alumni Hall of Famer gives $1 million to create endowment for first-generation students

Take it from a Florida State University luminary who has thoroughly known hardship:

When you maintain confidence and support, you can reset yourself and redirect yourself. You can transform your world and even your words.

Abandonment becomes achievement. Violence becomes benevolence. Adversity becomes university. And gloom becomes bloom.

This is the story of Tony DiBenedetto.

DiBenedetto rose from the depths of a turbulent childhood, including homelessness before he reached his teens, to become the first person in his family to graduate from high school. He then earned a college degree: a bachelor’s in management information systems from the FSU College of Business in 1987.

Now a Tampa-based technology executive, entrepreneur, philanthropist and college Alumni Hall of Fame member, DiBenedetto continues to make FSU a beneficiary of his giving and his emphasis on students who need a lift.

“What a story of perseverance, achievement and giving back,” said Michael Hartline, dean of the College of Business. “I’ve known Tony for a long time, and his personal and professional accomplishments continue to amaze me. His vision and generosity leave us all deeply grateful.”

DiBenedetto recently gifted the college $1 million to create the Think Big Endowment Fund, which will support first-generation students, including those who, like him, entered college with little money and direction. 

The fund will provide funding and resources to pursue professional-development opportunities, including networking events, workshops, conferences, internships and study-abroad trips – ever-essential activities for launching rewarding careers in business. The fund also will help those students develop the tools and skills they need to flourish, as he has.

DiBenedetto serves as chairman and CEO of Appspace, an award-winning workspace platform that serves more than 2,700 global businesses and some 12 million employees. He previously co-founded and led, as CEO, another technology company, Tribridge, which specialized in software services and cloud solutions. He lives in Tampa with his wife, Shannon, who earned MIS and accounting degrees from FSU, and their two daughters.

DiBenedetto said his latest gift stemmed from conversations with Hartline about new ways to help the college. His gift launches the fund, and he hopes its existence encourages others to contribute as well.

“That's why I'm calling it the ‘Think Big Endowment,’” he said. “It’s not about me. It’s about the students. How can we think bigger for students who are coming to the university with fewer resources and less preparedness?”

DiBenedetto made the gift in the spirit of Think Big for Kids, a nonprofit organization he founded in 2016. The organization boasts a mission to break the cycle of poverty by providing career exploration, mentorship, skills development and job readiness to middle and high school students. DiBenedetto said he got the Think Big idea while working with teens at Boys & Girls Clubs and observed in them a lack of career awareness and preparation for life after high school.

His previous gifts to FSU include an investment to create the Tony DiBenedetto Computer-Assisted Career Guidance Lab in the university’s Career Center, where he worked as a student. He credits the center for helping him transition from college to professional life.

For the U-turn he pulled off in his life journey, he credits a series of “sliding-door moments” and “all the people who helped me through them.”

They include grandparents who protected him, a family friend who took him in and inspired him and, at FSU, a mother figure who embraced him and showed him how to flourish.

‘A weird juxtaposition’

Born in Brooklyn, N.Y., Anthony “Tony” DiBenedetto experienced instability from infancy. He tells his story like so:

His mother gave birth to him and his younger brother before she turned 20, and his father left the family before he turned 2. His mother met another man and became entangled in drug use and trouble.

That prompted his maternal grandparents, immigrants from Sicily, to take him and his brother away from their mother. His grandmother took care of the home. His grandfather drove a cab, worked on a garbage truck and did odd jobs where he could. They had little money and a houseful of children, including their own. Over the years, their relationship with DiBenedetto’s mother and especially her boyfriend grew tense, escalating into an unthinkably violent act of intimidation against the family.

Although no one was hurt, the incident inspired the grandparents to begin a new life for their children and grandchildren. They moved the family as far away as they could, to Fort Lauderdale, Florida. DiBenedetto was 8 at the time.

Four years later, his grandmother passed away, and his grandfather could no longer take care of him and his brother. His brother went one way, and he went another: anywhere he could find a place to sleep. He stayed with friends and, for a time in high school, an uncle who dealt drugs, which heightened his sense of instability.

“It was a weird juxtaposition to go to school and be around good kids and good families and then, on and off, live in this culture of drug-dealing,” DiBenedetto said. “It was bizarre because it was never consistent – three months of living around bad stuff, and then three months of good, and then you live in this other place, and then you live in your car for a while.”

He played baseball at Fort Lauderdale High School and relished the discipline and belonging. In the classroom, he excelled in math, exuded confidence and demonstrated an outgoing, though unrefined, personality. He never doubted his ability to do well in school and life.

“I always believed in me,” he said.

Others believed in him, too. DiBenedetto pointed to a time when he was in seventh grade and moved in with a family friend. As part of the agreement, he paid no rent but did all the cooking. The day came when the family friend changed DiBenedetto’s life trajectory. 

“He told me, ‘Anthony, you’re not like them,’” DiBenedetto said, referring to family influences. “‘You’re different. You’re smart, and you can do something with that: education.’ This was the first time I understood, ‘There’s a choice here.’”

The family friend reminded DiBenedetto of his ability in math and showed him photos of a computer that NASA had used to get rockets and humans to the moon. This marked, in the mid-1970s, DiBenedetto’s introduction to computers, which immediately fascinated him.

He set his sights on college. And he aimed high.

‘He touched my heart’

DiBenedetto arrived at FSU in 1983 in a car that barely ran and with a personal roughness to match it. He got a job as a student assistant in the FSU Career Center and introduced himself to a woman named Pearly Rosier, who worked as a budget manager in the university’s Division of Student Affairs. 

They began a relationship that both likened to a parent and a son. “I was like a mother hen,” Rosier said. 

DiBenedetto would share stories about his family and life, and Rosier would listen and give direction. They clicked because they shared a love for people and memories of family dysfunction. Rosier also respected DiBenedetto’s energy and responsibility: He worked additional odd jobs, including as a restaurant server, to get himself through school.

“He touched my heart because I understood where he was coming from,” said Rosier, who retired in 2007 after 35 years at FSU. “I was someone he could come talk to when he needed to talk, when he needed to blow off steam.”

Rosier recalled a time when DiBenedetto expressed frustration over repeatedly getting ticketed for parking his car in front of campus garbage bins, despite “no parking” signs.

“I explained to him to obey the rules,” she said. “’Obey the rules, and you won’t get a ticket.’”

Actions carried consequences, she would emphasize. And words did, too.

“I had this chip on my shoulder, and she just coached me all the time about the right thing to say and when to say it,” DiBenedetto recalled. “How to stand up for myself but not be as aggressive, how to use better language and how to express my emotions. It was really a mothering.”

Rosier noted that DiBenedetto created a first for Student Affairs: a software application that tracked companies recruiting college students. That helped usher in the digital age for the university and foreshadowed a distinguished career in technology for DiBenedetto.

And DiBenedetto would never forget Rosier. About two years after he graduated, he called her with an invitation to his wedding. When she arrived for the reception, she asked him where she was going to sit.

“He said, ‘What do you mean where are you going to sit?’” Rosier said. “He said, ‘You’re going to sit with me and my bride at the head table.’ And it was beautiful.”

‘For me, it’s personal’

After earning his MIS degree from the College of Business, DiBenedetto took a job as an information technology consultant at Arthur Andersen, then accepted a role in a new business-consulting division at the company. In the meantime, he launched two businesses: a truck leasing company and a pizza and bagel restaurant.

In 1998, after 11 years at Arthur Andersen, DiBenedetto and colleagues Brian Deming and fellow alumnus Mike Herdegen (B.S. Hospitality Management ’85; MBA ’91) started Tribridge, a technology consulting firm that became one of the fastest-growing privately held companies in the U.S. The company became a multiple winner of Microsoft’s “partner of the year” and made the Seminole 100 list of companies owned or led by FSU alumni.

DiBenedetto led the sale of Tribridge in 2017. He remained active in other ventures and became CEO at Appspace in 2022 after serving as chair of the company’s board of directors since 2020.

Recent awards include three straight years in the Tampa Bay Business Journal’s Power 100. That publication also has declared him a “legend in the Tampa Bay Business community.” Previous awards included the Tampa Bay Technology Forum’s Member of the Year and, for his work at Tribridge, a CRN Magazine Technology Disrupter of the Year.

DiBenedetto says he has hired scores of FSU students over the past three decades and will continue to do so. For that, he cites his “affection for the university,” as he does for his gifts to FSU and the College of Business.

“For me, it's personal,” he said. “In addition to high school, I got so much at FSU from so many people.”

He recalled scholarships he received only because his guidance counselor and others took the time to help him apply for them.

“I remember this feeling of gratitude,” DiBenedetto said about his experience at FSU. “And I remember saying to myself: I’m going to pay this back.”

He says his Think Big Endowment Fund will remain a hallmark of his continued work and support of his alma mater. 

And as he continues to build Think Big for Kids, he’s preparing to launch Think Bigger Productions, a media company also dedicated to breaking the cycle of poverty for children. 

Call it another compelling chapter in the story of Tony DiBenedetto.

-- Pete Reinwald