Interview

Jason Matthews, based in Tampa, Florida, is a real estate investor and developer with over three decades of experience. Through 16 Redington Development LLC, he builds four-thousand-square-foot luxury beach homes designed for short-term rentals, with a specific focus on group bookings

At his first Board of Advisors engagement, Matthews productized his real estate model, generating $1.8 million in sales while partnering with a senior advisor with experience from a $200 million exit. That momentum led him to step into a chairman-level relationship, working more closely with leadership as he continues to scale.

His model is simple but intentional. Large-format homes, built for scale, designed to accommodate weddings, corporate events, and multi-family stays. Behind the model is a combination of discipline, lived experience, and a long-term perspective shaped by both athletics and business.

We sat down with Jason at Board of Advisors to understand the path that led him here and what continues to drive his work.

Q: Take us back to the beginning. What shaped your mindset around business early on?

As a kid, I already had my own business. My grandparents were both entrepreneurs. My grandfather was the first African American to have a car dealership license in California. He had a small lot in East Oakland, selling Cadillacs. My grandmother was a seamstress and sold dresses to women in the neighborhood.

I helped both of them. From my grandmother, I learned customer service. She turned her garage into a dress shop, and I would bring dresses out to customers and earn tips. From my grandfather, I learned speed math. He would have me add everything up on the spot, and you better not be wrong.

I always wanted to make money, so I worked with them as much as I could.

Q: You mentioned having your own business as a kid. What did that look like?

I used to pull my neighbors’ garbage cans to the curb on trash day and make money that way. Then I had what I call my best business mistake.
During the recycling boom in Los Angeles, I tried to scale a can collection business. I went door to door, collected about twenty-five or thirty bags of aluminum cans, and thought I was going to make real money. When we got them weighed, it came out to about three dollars and seventy-eight cents.

I shut that business down before we even got home.

Q: How did sports influence that way you approach business today?

Sports taught me teamwork, discipline, and how to deal with things that are out of my control.

I have been involved in youth development for almost forty years, and I believe sports teach real life.

You learn how to deal with adversity. You learn how to manage situations where things are not fair and still perform. That carries directly into business.

“You learn how to deal with adversity. You learn how to manage situations where things are not fair and still perform.”

Q: You had a strong basketball career. What did that experience give you beyond the game?

My dad put me in sports early, and I started playing basketball at fourteen. I became a top sixty player in high school and had over a hundred Division One scholarship offers. I went to the University of Pittsburgh, got my economics degree, and scored over eighteen hundred points. I am sixth all-time in scoring there and still hold Big East and NCAA shooting records.

But I was never the best player on my team. I played with guys who went on to win NBA championships. That keeps you realistic.

More than anything, it built mental toughness. Growing up in Los Angeles, you had to develop that early. You are exposed to things at a young age that force you to learn emotional control. That mental discipline is what I carry into business.

“I always had a dual path. I told myself that if I did not make it to the NBA within two years, I would move on.”

Q: After basketball, you moved into finance. How did that transition happen?

I always had a dual path. I told myself that if I did not make it to the NBA within two years, I would move on.

I tried out for NBA teams like the Lakers and the Bucks, played overseas in the Philippines, and then transitioned into finance. I became a licensed financial planner. I had also been exposed to the capital markets earlier through internships with my brother’s friend, who was an investment banker.

Q: What made you pivot from finance into real estate?

My wealthiest clients. I saw what they were doing in real estate and how they were building wealth. They were generating strong returns and putting money back into their families and future.

I realized I was on the wrong side of that equation. That is what pushed me to make the move.

Q: Tell us about 16 Redington Development, LLC and what you are building today.

We are in the short-term rental space. It is a family business with my wife and our three kids.

We build luxury beach homes, about four thousand square feet, typically with six bathrooms and designed to sleep ten people. The key difference is that we focus on group bookings.

We can combine multiple homes to accommodate larger groups. Weddings, family reunions, corporate events, and even university fundraising events. Right before this interview, we had an inquiry from a college looking to use our homes for fundraising.

That is what makes us different. We are built for that type of demand.

Q: Where does the project currently stand?

We have three homes completed, three under construction, and thirty to build. We will likely sell about twenty-five and hold eleven as long-term assets.

We already have permits in place, and we work with a builder who completes forty to forty-five of these homes annually in Pinellas County.

Right now, I am focused on raising equity. The structure allows investors to receive returns and potentially have their capital returned through construction loan refinancing rather than waiting for a full property sale. The timeline is typically twelve to fifteen months.

Q: What is the deeper purpose behind what you are building?

My son Brandon. He has mild autism, and basketball has been his way of connecting with the world.

He worked hard, made his team, and eventually became a team captain in high school. That was a very special moment.

Through a connection with Orlando Antigua, who played at Pittsburgh after me, Brandon became a team manager at the University of South Florida. Our whole family moved from Pittsburgh to Tampa so he could pursue that opportunity.

He has been part of the program, traveling with teams and building relationships across college basketball.

“We want to show parents that there is no reason to isolate a child with autism. There is opportunity there. The business supports that vision.”

Q: How does that connect to your long-term vision?

The long-term goal is to build him his own basketball training facility in Tampa. A place where players he has connected with can train. Some are in the NBA, some play overseas.

We also keep his life public intentionally. We want to show parents that there is no reason to isolate a child with autism. There is an opportunity there.
The business supports that vision.

Q: What is the best way for people to reach you?

I am very accessible. No gatekeeper. You can visit our website at 16redington.com or reach out to me directly. I will respond.