Why I Chose Real Estate—and Why My Friends Said, “It’s About Time”

For years, real estate was a part of my life without ever really being my profession.

I bought homes, invested in properties, followed markets, and paid attention to what was happening in Florida because Florida has always been home to me.  I’m a fourth-generation Floridian, so I’ve watched this state change, grow, reinvent itself, and attract people from all over the country.  But the real connection for me was never just the property.

It was always the people.

I Became a Sounding Board Before I Became an Advisor

Over the years, friends and colleagues would call me when they were thinking about making a move, looking at an investment, considering Florida, or simply trying to figure out whether something made sense.  They’d ask me what I was hearing, what I thought of a particular area, whether I knew someone they should speak with, or whether I thought an opportunity was worth pursuing.  In a lot of ways, I became a sounding board long before I ever became licensed. I didn’t think much about it at the time.  It was just what you do when people trust your judgment.

“In a lot of ways, I became a sounding board long before I ever became licensed.”

Different Worlds. The Same Principles.

My career had already taken me through a lot of different worlds.  I spent years in national marketing, photography, branding, film production, talent management, public relations, and business development.  I worked around entertainers, athletes, executives, agents, managers, producers, media companies, and people who were used to operating at a very high level.  In those environments, you learn pretty quickly that access only gets you so far. Everybody knows somebody.

What matters is whether people trust you when something important is on the line.

Producing a film is probably a good example.  On paper, you’re making a movie.  In reality, you’re managing personalities, contracts, schedules, budgets, talent, representatives, production teams, investors, and about fifty things that can go sideways before lunch.  You learn how to read a room.  You learn when to push, when to listen, when to solve the problem quietly, and when somebody simply needs to know that you’ve got it handled.  Those lessons stayed with me. 

The same was true in talent management and marketing.

Whether I was working with a national brand, developing talent, dealing with an agency, coordinating a media appearance, or putting together a production, the work always came back to relationships.  I’ve been fortunate to build relationships that have lasted for decades, and I take a lot of pride in that.  Some started in business and became friendships. Some started as friendships and eventually led to business.

Either way, there was always an understanding that if I put my name behind something, I was going to stand behind it.

“Access only gets you so far. What matters is whether people trust you when something important is on the line.”

When Real Estate Started Making Sense

That is really where real estate started making sense for me.  Friends would call and say, “Lou, keep your ears open for me.”  Or, “I’m thinking about Florida. Where would you look?”  Or, “I’ve got a friend who wants to buy down there. Who should they talk to?”  Those conversations became more frequent, particularly as more people I knew in California, New York, Chicago, and other major markets began looking at Florida differently.  They weren’t just coming down for a weekend anymore.

They were thinking about residences, second homes, businesses, investments, taxes, lifestyle, and where they wanted to spend the next chapter of their lives.

I understood why they were looking here.  But I also understood them.  That mattered.  People who have spent their careers in entertainment, sports, business, or other high-performance environments generally don’t want to be sold to.  They want good information.  They want someone who can get to the point.  They want discretion.  They want to know who is actually paying attention, who can make the right call, and who is going to handle the details without creating ten more things for them to manage.  That is the part of real estate that interested me.

Before the Listings

I wasn’t looking to become the guy who sends you twenty listings and asks which kitchen you like best.  There are plenty of people who can do that.  I was interested in becoming the person you call before you even know exactly what you want to do.  The person you can say, “Here’s what I’m thinking,” and know that the conversation is going to be thoughtful, private, and useful.

“I wanted to become the person you call before you even know exactly what you want to do.”

Eventually, enough friends told me I was in the wrong business that I started listening.  My answer was always, “Which one?” because, to be fair, I had been in a few.  But they had a point.  The common denominator through almost everything I had done professionally was the same skill set that good real estate representation requires:

Relationships. Judgment. Negotiation. Coordination. Communication.

And the ability to keep complicated situations moving without making them feel complicated to the client.

Why The Sage Team

That realization ultimately led me to The Sage Team Private Office.  

What appealed to me about The Sage Team was that the approach felt familiar.  The relationship comes first.  The transaction matters, obviously, but the transaction is not the relationship.  The objective is to understand what the client is trying to accomplish and then build the right strategy and resources around that objective.  That might be a primary residence in Tampa, a second home in Palm Beach, a new construction opportunity, an investment, a relocation, or a property somebody already owns and is considering selling.  Sometimes it may simply start with a conversation about whether Florida even makes sense.  The Sage Team gives me something I wanted before I made this move: depth behind the relationship.

I can bring the people, perspective, and trust I have spent years developing, while working alongside an experienced real estate team with the strategy, market intelligence, negotiation, operational support, technology, and transaction management required to deliver at a very high level.  That combination matters to me because the people in my world are accustomed to having strong teams around them.  An athlete has an agent, a business manager, an attorney, a financial advisor, maybe a publicist.  An entertainer may have an entirely different team, but the principle is the same.  Nobody at that level expects one person to know everything.  They expect the right person to know how to assemble the right people, get accurate information, protect the objective, and keep everyone moving in the same direction.

That is how I see my role in real estate.

It’s About Time

So when people ask me why I chose this business, the truth is that it doesn’t really feel like I suddenly chose real estate.  It feels more like real estate finally gave a home to a lot of the things I had already been doing for years:

Listening. Making connections. Evaluating opportunities. Solving problems. Managing relationships. Helping people make important decisions.

And when I finally told some of my longtime friends that I had made the move, I heard the same response more than once.

“It’s about time.”

They were probably right.

Lou Maggio
Real Estate Executive | Strategic Relationships
The Sage Team Private Office