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Tony DiBenedetto serves up uncensored wisdom at Startup Week Tampa Bay

Megan Holmes

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Tony DiBenedetto (left) Rich Heruska (right). Photo by Megan Holmes.

Last year, Startup Week Tampa Bay brought in Gary Vaynerchuk, media mogul and best-selling author with 1.81 million Twitter followers at last count. He brought the hype, and thousands of people turned out to see him for an electrifying talk on the state of entrepreneurship. In fact, one of my very first pieces for the Catalyst was written that night. You can read my piece,The Evangelism of Gary Vee, here.

This year, Startup Week is a different product. They didn’t have the big name draw of Gary Vee, but instead compiled thoughtfully-curated, intimate panels and local influencers to share their success stories at scale. In perhaps the most anticipated speaker of the week, Tony DiBenedetto, they gave us someone arguably more compelling and relatable than the half-man, half-brand Gary Vaynerchuk. (Although the jury’s still out on who threw around more f-bombs.) 

Thursday night, we heard from DiBenedetto, co-founder of Tribridge, the Tampa tech company that sold for nearly $160 million in 2017. DiBenedetto gave an unfettered and uncensored fireside chat on failure, persistence, and leading with great culture, at Armature Works in Tampa.

DiBenedetto cut straight into the start of his entrepreneurial journey, the story of his first entrepreneurial endeavor and failure – A Taste of New York – in the early ’90s. At 24, DiBenedetto was a young IT/tech consultant at Arthur Andersen living in Tampa. He was hungry for opportunity – and pizza from his native city of Brooklyn, New York.

“We were going through the George H.W. Bush recession, so of course my smart idea in a recession was to go into retail,” laughed DiBenedetto. With zero retail knowledge and even less experience in the kitchen, DiBenedetto came away with a few important takeaways. He lost about $50,000 (twice his yearly salary at the time), learned how to make pizza and bagels, and vowed never to invest in retail again.

His ‘Come to Jesus Moment,’ he says, was when he was an “Arthur Andersen consultant, tech consultant by day and delivering pizza by night.” A run-in with a client helped him realize that he wasn’t quite living the life he wanted.

“I showed up at this guy’s door and he’s kind of looking at me like, ‘Man, you look familiar,” DiBenedetto explained. “And I realized he was a client that I was billing like $200 an hour in the daytime – and at night I’m the pizza guy delivering his pizza.”

Unlike most stories of failure, there was no down time for licking wounds and pity parties for DiBenedetto. He attributes it to a “strange sense of either confidence, forgetfulness, stubbornness – some weird thing that makes me hard to live with, I think.”

“But from an entrepreneurial perspective, I don’t think it phased me at all,” he mused. “I just thought, ‘Man I’m never doing this again.’ But I was walking away with a lot of value. Not green value, but a lot of other colors. Vomit and everything else,” he laughed.

That sense of “dumb confidence” has gotten DiBenedetto through good times and bad – even a particularly spotty childhood. DiBenedetto was born in Brooklyn during a period of pervasive drug use in New York City. His mother was a heroin user for much of her life, his father absent. He was raised by his grandparents from the time he was a year old until his grandmother’s traumatic death when he was 12.

After bouncing around from house to house for two years, DiBenedetto began supporting himself at 14, using fake identification and a pseudonym (Tony Russo) to begin working as an adult.

That persistence, dumb confidence, or short memory – whatever you’d like to call it – is part of what makes a good entrepreneur, DiBenedetto said. The important thing is knowing which voices to listen to.

Tom Wallace, now the managing partner of Florida Funders, was one of the right voices for DiBenedetto. When Tribridge was not yet a twinkle in the eyes of the three co-founders, they pitched Wallace on a CRM platform similar to what Salesforce would later become.

While he declined their $3 million pitch, he told them – three young Arthur Andersen consultants at the time – to stick with what they knew (IT) and let customers dictate the need for a CRM later. He believed in them so much, he wrote a check on the spot for $300,000. They listened.

“We left that day feeling on top of the world,” DiBenedetto recalled. “Tom literally pushed us off the ledge and we built the business plan for Tribridge after that.

“The funny thing is, the business plan is horrible. If I circulated that plan to any of you, you’d be like ‘my business plan is 50 times better than this piece of crap.’ But the thing that I think turned out to be genius wasn’t the strategy or the number of offices we were going to open or the services. It was that we spent more of the plan thinking about how we were going to treat people.” 

Tribridge has long been celebrated for its exceptional culture, but it is probably best known for its $160 million sale to DXC Technology, a multi-billion dollar IT services company, in 2017. That sale made Tribridge an undeniable Tampa Bay success story, and brought DiBenedetto to further prominence as a tech influencer. DiBenedetto acknowledged that he’s often credited with the company’s success, despite co-founding the company with fellow entrepreneurs Brian Deming and Mike Herdegen.

“I’m kind of like the David Lee Roth of Van Halen,” DiBenedetto joked. “If you guys know about how that band was constructed, David Lee Roth was not a decision maker. He was the front man but he got kicked out of the band like three times.”

The fully-fledged story of DiBenedetto, unfiltered and nonegoic, comes at a time when Tampa Bay’s tech ecosystem is taking off: more capital is coming in than ever before, and second and third generation entrepreneurs are building companies throughout the region. Self-described as both straight-talking and verbose, DiBenedetto could be the influencer Tampa Bay needs to build and tell our own story.

“I hate that we always compare ourselves,” DiBenedetto said. “That’s the worst thing we could ever do. Does anybody here want to be Austin, or the Valley or New York? Why would we want to be that? I want to be Tampa Bay.”

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