Knock down obstacles

When Tony DiBenedetto was 19, he didn't even know what an entrepreneur was.

But he was intrigued by the concept when a friend started a business importing Brazilian art to Tallahassee during college. Plus, he figured owning a business was the only way to accumulate enough wealth to own his favorite baseball team: the New York Yankees.

Today, DiBenedetto is one of the most celebrated executives in Tampa. The company he founded in 1998, Tribridge, has grown to $170 million in revenue in 2016. The company's market share in cloud computing software and services, along with its top-tier work integrating Microsoft Dynamics, catapulted it to the national stage in recent years. That effort culminated in a July acquisition, when DXC Technology, a $7.6 billion publicly traded IT services company, bought Tribridge. The company is now called Tribridge, a DXC Technology Co.

DiBenedetto, 52, is a mentor and unofficial counselor to several high-powered tech executives in the region. He recently sat down with the Business Observer to talk about his career and what's next after Tribridge. Edited excerpts:

Rough patch: DiBenedetto calls his childhood “checkered.” His mother was a heavy drug user. He jumped from home to home in poor neighborhoods. He lived with his grandparents for a bit, with a Spanish-speaking family for a little while and with a German family for some time. “I wasn't a ward of the state, I was an adopted child of the community,” he says.

With a lot of his family members spending time in jail, “it's something you can run toward or away,” DiBenedetto says.

Education is what led him on the right track. In high school, he says he was lucky to have people bring him under their wing. “The system pushed me through,” he says.

Entrepreneurial start: Though he worked for 11 years at consulting firm Arthur Andersen, DiBenedetto knew he wanted to start his own business.

Before they married, he had a long talk with his future wife, Shannon. He warned her: “You have to understand something about me — there's no way I'm staying at Andersen. I want to take a lot of risk, and there's a good chance I'll bankrupt us,” he recalls. “You have to be ready for a roller coaster.”

Then DiBenedetto met Tom Wallace, now a Tampa-based investor in multiple tech companies. Wallace, says DiBenedetto, was the reason he became an entrepreneur. “I worked for one of the best consulting companies in the world and I was a young partner,” DiBenedetto says. “Tom gave me the push off the ledge. Not just the capital, but the confidence.”

Wallace says DiBenedetto “had the desire to do something, and he had energy, the smarts and the tenacity.”

DiBenedetto and his co-founders walked into a meeting with Wallace pitching an idea for a new software. Wallace told them they should really focus on what they already knew — IT services. The partners agreed, and Wallace wrote a check on the spot. Says DiBenedetto: “We got the money first and wrote the business plan later.”

Growing Tribridge: One year into starting Tribridge, DiBenedetto says they had the “best worst meeting ever.”

The subject? Bottled vs. filtered water.

“We're never doing this again,” DiBenedetto says. As co-founders of the startup, DiBenedetto, Mike Herdegen and Brian Deming wanted to share everything. But after the “best worst meeting ever,” they decided they needed to divide and conquer.

They determined their individual talent. “It let us put our foot on the gas and really take advantage of our strengths,” DiBenedetto says. Herdegen focused on technology, Deming on operations and DiBenedetto on strategy and sales.

Though Tribridge started as an IT services company, DiBenedetto says it eventually became painful to scale. “As a pure project services company, you eat what you hunt,” he says. A decade into it, in 2008, the company was at $15 million in sales — with zero recurring revenue.

That's when the founders decided to add products, starting Tribridge's cloud and software businesses. “That gave us more hypergrowth,” says DiBenedetto. Today, 40% of the company's $170 million in annual revenue is recurring.

Best decision: DiBenedetto credits the company's success to building a document of guiding principles, along with Tribridge's first business plan.

Those guiding principles morphed into the company's culture, he says, including maintaining an entrepreneurial spirit; setting guidelines for how they treat people; having a servant leadership style; and building a company with honesty and integrity.

DiBenedetto had all managers read “The Servant,” by James Hunter, a book he considers the greatest leadership book ever written. He asked the managers to adopt the servant leadership management style.

The company adopted a giving mentality gleaned from Adam Brand's “Give and Take.” It's counterintuitive to his upbringing and industry, which aren't touch-feely, but DiBenedetto says a key lesson he has learned from those books, and growing Tribridge, is success is about how he treats people. “The business thrived on it,” he says.

Keep the spirit: Launching new products and services allowed DiBenedetto to continue to doing all things entrepreneur —“rocket fuel for my brain,” he says

“I have a very heavy foot driving — you have to go fast, take market share and not waste time,” DiBenedetto says.

Even as the company grew and was subsequently sold, he felt empowered to be even more entrepreneurial and assertive in the marketplace because he had more resources. “I never put myself in a role where I felt I had to do the operations,” he says.

Schedule time: DiBenedetto schedules downtime “to sit in the office or go for a drive and think,” he says. “I put it on my calendar.”

He says any person who runs a company or a division has to do that because they are always busy and need time to let their mind clear and ideas flow.

Idea man: The place where DiBenedetto gets his best ideas? The shower.

He typically takes a quick shower, but sometimes his mind wanders and he starts to think. “It's like I blackout,” he says. Something a customer said a few days earlier will “swirl around” and he'll “germinate on it,” thinking, “'Why don't I fix that problem for all customers?'”

It might be 15 minutes later and he won't remember if he used shampoo.

Give back: Voicing his opinion is one of DiBenedetto's strengths, says Brian Murphy, CEO of Tampa-based cybersecurity firm Reliaquest. “It takes some confidence, a belief and some tact,” says Murphy, a friend who has also leaned on DiBenedetto for advice in growing and running Reliaquest.

DiBenedetto's advice, says Murphy, is never insulting and always something new and of value. “When (DiBenedetto is) talking about what's worked for him,” says Murphy, “he's the one you have to listen to; he's done it to scale.”

Wallace, a managing partner at Florida Funders, says DiBenedetto is the most giving person he's met in his career. “Not only giving back to the community in terms of generosity,” Wallace says, “but also in time and commitment and not expecting anything in return.”

A big example: DiBenedetto started a charity, Think Big for Kids, that encourages local executives to serve as mentors to fifth- and sixth-graders at the Boys and Girls Club.

Pride and joy: Watching his employees grow has been more rewarding than anything he could have imagined, DiBenedetto says. He's seen his people get married, watched them have children and watched them leave and start their own companies.

“I really love watching people blossom either here or somewhere else — that really makes me tick,” he says. “I get a better kick out of that than a customer experience or an award.”

Wallace says DiBenedetto never puts himself first, “almost to a detriment ... It's always what's the best for the company, what's best for the team, not about what's best for Tony.”

Happy days: DiBenedetto's passions are cooking, hiking, baseball and spending time with family. The best times are when he can combine his passions, he says. For example he enjoys cooking with his 6-year-old daughter in matching aprons with the name of their “restaurant,” Recipes.

He also loves taking trips out west to go for 6- to 8-mile hikes with his wife. “There's something about connecting with the Earth — it clears your brain,” he says. “No cell coverage, no people. I have lots of noise in the day-to-day from social issues to business.”

When he's out hiking, he let's all of that go. “Your heart's beating,” he says, “and water is running, and you can feel the connection.”

Next up: DiBenedetto's job now is to integrate Tribridge into DXC and help with cloud and Microsoft services in North America.

It's a shift to not being the No. 1 guy. “I might have ideas I'll have to pass on to others, I have to be OK with that,” he says. “It will be different; I won't be the CEO.”

And owning a professional sports team? It remains a goal. He realizes it's almost economically impossible, but DiBenedetto is the epitome of never-say-never.

“I off the charts love baseball,” he says, adding he'd be OK with being a part of a group that owns a franchise. “It's serious — but not at the front of my brain.”