From Wall Street to Miami's Waterfront: Jay Roberts' Vision for Prosper Group

Jay Roberts didn’t just pivot into real estate development—he engineered his way in, layering decades of finance expertise with an innate instinct for placemaking. Now the founder of Prosper Group, Roberts is quickly becoming one of the most influential names reshaping Florida’s urban landscape, from Brickell to North Bay Village to downtown Tampa. His formula? Prime areas (preferably on the water), wellness-centric design, and an unwavering obsession with best-in-class locations.

“I’ve been in real estate for 19 years,” Roberts told Traded. “I started in college, interning at a commercial brokerage, then worked with the number one multifamily investment sales team in California. After my MBA at NYU, I joined Bank of America Merrill Lynch’s real estate investment banking group, doing M&As and IPOs for REITs. That’s where I cut my teeth.”

But the leap from finance to development didn’t happen overnight. Roberts built one of the largest Airbnb startups in the country, managing 2,000 units across ten states. In 2020, he relocated to Miami and began making strategic moves, working with heavyweights such as Related Group, CIM Group, and Russell Galbut. He was also brought onto Dan Kodsi’s team at Royal Palm Companies to help finance Legacy at Miami Worldcenter.

Now, his first major development, in partnership with Arc Realty, is already making waves. Hotel ORA, located in downtown Tampa, is a 622-unit waterfront condo hotel that’s sold over $130 million in just five months and is projected to hit $600 million in total sellout. “That was a full city block I assembled myself,” Roberts explained. “It’s the first true condo hotel in Tampa and a signal of where that market is going.”

Prime Real Estate, Health-First Design

From the start, Roberts has been relentlessly focused on location. Whether in Brickell or North Bay Village, his mantra is clear: “Start with the site. I only go after 10 out of 10 locations.”

Take 1040 S. Miami Avenue, a future Prosper development that sits in the heart of Brickell. “We’re building what we hope will be the healthiest residential building in Miami,” Roberts said. That’s not just marketing spin. Prosper is incorporating fitness and wellness programming far beyond a standard condo gym—think IV therapy rooms, red light therapy, cryotherapy, high-end saunas, steam rooms, and fully blackout bedrooms optimized for circadian rhythms.

“Health is the new wealth,” he said. “People want to live longer, live better. That’s what we’re designing for.”

It’s a philosophy that tracks with Roberts’ own lifestyle. At 40, he says his biological age is 24—a result of following longevity pioneers like Bryan Johnson and participating in Miami’s “Don’t Die” summits and biohacking events. He’s building that same ethos into his developments, down to temperature-controlled rooms for deep sleep.

Prosper’s Riverside project, on the Miami River, will be a signature statement of that blend: water access, luxury, and proximity to high vibrational energy. “We’re building five private yacht slips, 158 residences, a rooftop restaurant, and waterfront office space—all across from Brickell City Centre, but tucked away from the congestion,” Roberts noted.

A New Chapter for North Bay Village

One of the most buzzed-about moves in Roberts’ portfolio is his entry into North Bay Village, a quiet, centrally located island that’s rapidly emerging as Miami’s next development frontier. For Roberts, it evokes comparisons to other now-iconic neighborhoods that underwent dramatic transformations.

“I see North Bay Village following in the footsteps of Bay Harbor and South of Fifth,” he said. “It’s one of the last islands to be developed. We have the chance to create something truly peaceful and special there—waterfront island living, but still connected.”

As an enclave with expansive water views, close proximity to the mainland, and limited remaining parcels, the area is poised for a major design-led renaissance. And Roberts is positioning Prosper to be one of the early movers shaping that narrative.

Off-Market Strategy: Playing the Long Game

Prosper’s 1040 S Miami Ave. site in Brickell, came with its own backstory—and it encapsulates how Roberts approaches acquisitions. Previously under contract to become a Virgin Hotel and Residences, the site was considered one of the area’s most coveted parcels. But it never traded hands—until Roberts stepped in.

“I actually reconnected with the owner by chance,” Roberts recalled. “I popped into a liquor store with my trainer on a Saturday, asked if the owner, Jeff, had sold the site. They said no. I made the call, and the rest unfolded from there.”

Roberts had originally met Jeff Chen, the owner, in 2019 while building his startup. Fast forward to Q1 2024, and that casual conversation in a liquor store turned into a signed deal. “We called the broker, flew to meet Jeff, and restarted the dialogue. With prime off-market deals, it’s no secret who owns what—what matters is building trust.”

That philosophy is baked into how Roberts operates. “I’m transparent with my process—what I can and can’t do. I communicate clearly. These contracts often stretch a year or more, so communication and rapport with sellers are critical.”

Even after signing, Roberts stays hands-on. “I was just in New York meeting with Jeff. For me, it’s about aligning incentives so the seller, the development, and the vision all benefit.”

It’s a patient, people-first strategy that’s not just helping him secure marquee sites—it’s helping him build long-term relationships and a reputation as one of Florida’s most trusted emerging developers.

Tampa & Beyond: A Statewide Vision

While Miami remains Prosper’s home base, Roberts is increasingly eyeing other Florida markets like Fort Lauderdale, West Palm Beach, and Tampa. The Tampa market, he says, has matured rapidly thanks to Jeff Vinik and Bill Gates’ $4 billion Water Street development, which anchored a walkable, live-work-play downtown that didn’t exist just five years ago.

“Tampa is calmer, less international, but growing in affluence. It’s attracting people from the Midwest who want a different pace but still crave luxury,” he said.

Despite the sharp increase in ultra-luxury developments across Florida, Roberts believes the trend is more about feasibility than exclusivity. “It’s not that developers only want to build luxury. It’s that the economics of development—the land, construction, financing—often make it the only viable option,” he explained.

What’s Next for Prosper Group?

With four active developments, over 1,300 units, and $2.6 billion in projected sellout, Roberts is keeping his team focused and lean. “We’re taking it day by day, making sure we don’t bite off more than we can chew,” he said. “Our goal is to deliver world-class experiences with world-class partners.”

And as a founder who came from finance, he has advice for others looking to do the same.

“Start by mastering your market. Be trustworthy. Know zoning, know the community, know construction. Everyone in Miami knows everyone—your reputation will precede you.”

As Prosper Group continues to push the boundaries of health, luxury, and waterfront lifestyle, Roberts is positioning himself as a developer not just of buildings, but of how people live in the future.