Bobby Souza’s pivot to real estate is all about scale, systems, and staying power

Bobby Souza didn’t grow up thinking about cap rates, occupancy targets, or the nuances of guest experience. In fact, before real estate, his world revolved around data science, SaaS leadership, and running high-performing analytics teams. But four years ago, something clicked: a blend of entrepreneurial itch, curiosity, and a growing awareness of the long-term potential in real estate.

“I didn’t learn about real estate or investing growing up,” Souza said. “But once I started looking into it, I realized I could apply my analytical mindset to something that could build real wealth.”

He entered the market the way many do, on the short-term rental side. But unlike the weekend hobbyists who flooded platforms like Airbnb during the pandemic, Souza approached it with discipline. Today, he runs a short-term rental management company focused on high-volume vacation markets like the Disney area and South Florida’s beaches. He’s spent the last three years building systems to deliver consistent service in one of hospitality’s most operationally intense niches.

“It’s one of the hardest real estate businesses to run,” Souza said. “You’re on the clock 24/7, and guest experience drives everything. But it’s taught me a ton about operations and about staying sharp.”

That experience now feeds into his work as Asset Manager at Gilberti Group, where Souza takes over properties post-acquisition to ensure they’re stabilized and well-run. He handles leasing, occupancy strategy, and operational execution. Equally, Souza plays a broader role in market research, early diligence, and relationship-building ahead of acquisitions.

He sees it as the perfect mix of structure and scale. “I love the group’s vision of scaling into multifamily and eventually boutique hotels,” he said. “Everyone brings something different to the table, but the work ethic is the same: roll up your sleeves, get things done.”

Souza’s combination of tech fluency and on-the-ground real estate experience is helping Gilberti Group stay agile in a market that’s shifted dramatically since the pandemic. Where once it was easy to list a unit and see profits roll in, now success in short-term rentals – and real estate more broadly –depends on strategy, systems, and execution.

“COVID brought this flood of new investors into the space,” he said. “But as barriers to entry rise and regulatory pressure builds, only the serious operators are sticking around.”

He’s especially bullish on South Florida, not just because of the demand drivers like Formula One, Inter Miami, and the region’s year-round appeal, but because of the untapped value in underused properties. Souza envisions a future where Gilberti Group redevelops older motels into unique boutique hotel assets that add character (and yield) to the local market.

“The opportunity to take a neglected building and turn it into something beautiful. That’s exciting,” he said. “And it’s already happening. You’re seeing people convert senior living homes into award-winning hotels. That’s the kind of creative, high-impact investing I want to be part of.”

For now, his focus is clear: meetups, masterminds, deal flow, and prep. The team is gearing up for its first acquisition, and Souza is ready to activate. “This is just the beginning,” he said.