Jay Roberts of Prosper Group: 5 Questions

Developer Jay Roberts is making a splash in South Florida. 

The CEO of Miami-based Prosper Group recently closed on a $50 million site along the Miami River in the city’s Brickell district. The 1-acre site includes 66 Southwest Sixth Street and 625 Southwest First Avenue, along with about 300 feet of river frontage.

Before he embarked on a career as a real estate developer, Roberts worked on Wall Street. Among the large deals he worked on was the $2.6 billion initial public offering of Paramount Group Real Estate Investment Trust.

As he builds his real estate portfolio, Roberts also is curating a social media following through his podcast, “The Long Game,” and his 175,000 followers on Instagram.

The following conversation has been edited for length and clarity.

Commercial Observer: You’re pretty new to South Florida. What are you working on?

Jay Roberts: We have currently a $2.8 billion pipeline – three projects in Miami and one in Tampa. We focus on waterfront, best-in-class development sites. We’re not looking to bite off more than we can chew, and we just want to execute what’s in front of us. 

We just closed on a site on the Miami River for $50 million to build a luxury high-rise, and then we have a second commercial building coming that we haven’t announced, but it’s a two-phase project. We’re looking for the cream-of-the-crop sites. 

My background is investment banking and finance. I worked on Wall Street at Bank of America Merrill Lynch. One of my superpowers is raising capital, identifying sites, structuring joint ventures and doing deals.

What spurred your transition from Wall Street to real estate development?

I moved to Miami and there was so much real estate development happening here. I met a developer, Dan Kodsi, in 2019. We started doing some work together and he said, “Jay, we could use a New York or finance person to raise capital, and you have that experience and you manage a lot of people.” Having New York finance relationships and experience was an asset to focus down here in Miami.

I moved to Tampa in 2022. I saw Bill Gates and Jeff Vinnick investing $4 billion to create a new Downtown Tampa called Water Street. I assembled the first city block development around that time in 2022, right near Water Street, and then I brought in a co-developer to develop the first condo-hotel in Tampa. 

Then in 2023, I moved back to Miami and started looking at development sites on the water.

Since you mentioned that $50 million site on the Miami River, what are your plans for that property?

We’re planning a residential luxury high-rise – about 60 stories, 181 units right on the Miami River, right outside of Brickell City Centre. We have some announcements coming. 

We can’t announce pricing yet. We have over 80 consultants working on this project, from our design architect, our civil engineers, our structural engineers, our MEP consultants, our sales team, and our development partners.

How are you using social media and your podcast to accomplish your development goals?

I started in social media by providing data and educational value to followers. I started with 5,000 followers in March of 2025 and have grown to 186,000 followers. And since then, we’ve had over 32 million views in that time frame. 

I have three rules when creating content. No. 1 is if it’s cringy, don’t do that type of content. The second rule is, don’t create any kind of ego-driven, attention-seeking content. No flashy cars, things like that. And No. 3 is to educate and provide value to the audience. It’s worked well. We got a lot of traction.

We’re using this to educate the market, provide transparency and build goodwill and trust in the market, and really build relationships. We’re doing brand deals and partnerships with investors.

In the past, those types of relationships – with investors, for instance – wouldn’t have come through through social media. They would have come through word of mouth or industry conferences or some kind of face-to-face interactions as opposed to social media.

Right, right. This is sort of the new age, the new versus the old way and old business style. People are spending so much time on social media, from young people to older people, that it’s a good sort of free marketing to provide that value and utilize the platforms.

Jeff Ostrowski can be reached at jostrowski@commercialobserver.com.