This Is Your Freestyle Blast #56

The Sound. The Style. The Memories.

Aug 15, 2026

There are certain things about Freestyle that are difficult to explain unless you’ve lived it.

It’s not just the music. It’s not just the concerts, the artists, or the fans. Somewhere along the way, Freestyle became connected to something much deeper, our memories, our friendships, our youth, and even the places we call home.

And sometimes, you don’t fully realize just how powerful that connection is until you step back and look at it from a different perspective. That’s exactly what happened to me recently.

In this month’s issue of The Blast, I’m sharing two articles that are very different from one another, but both made me stop and think about what Freestyle really means.

The first comes from a recent experience on the road, where we found ourselves doing two Florida shows back-to-back. Two different cities, two major shows, and two absolutely incredible nights. But somewhere between those two performances, I started noticing something about the people in those audiences that made me look at Freestyle a little differently.

I’ll tell you more about that in “Freestyle Family, Friends, Fans… Florida.”

The second article takes us in a completely different direction. We talk a lot about the music. The songs. The artists. The memories. But what about what we see?

Does a Freestyle artist actually have an image? And if that image isn’t clearly defined, is it too late to create one? Is image really that important to an artist’s career, especially after decades in the business?

Those are some of the questions I explore in “What Does Freestyle Look Like?”

I’m not giving you the answers here. You’ll have to read the stories and decide for yourself. Because when you really think about it, neither article is simply about what’s happening on the surface. They’re about where we came from, who we are, and how we continue to carry Freestyle forward.

So before you turn the page, I’ll leave you with two questions: What does Freestyle “feel” like to you? And… What does it look like?

I have a feeling the answers might be more connected than we realize. Now go ’head and enjoy Issue #56 of The Freestyle Blast Newsletter.

😏👉 Oh, and one more thing. The Freestyle Blast Newsletter will always be free. We don’t ask for donations, contributions, or tips. Instead, we ask for something even more valuable... your engagement.
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FREESTYLE IN FLORIDA
The Friends, The Fans, The Family!

There’s something different about it…

Or should I say, something familiar?

One of the cool things about what I do is that I get to wear a few hats.

I’m a manager and booking agent for some of Freestyle’s most respected artists, but I also take on the role of road manager. In other words, I don’t just help manage careers and book the shows, I often hit the road and experience those shows right alongside the artists.

That isn’t necessarily the norm. Many management companies hire dedicated road managers to travel with their artists and handle everything that comes with being on the road.

But I’ve always chosen to be there myself. Not with every artist I book, of course, but with a select few, Lil’ Suzy, Angel OCG, The Cover Girls, and, back in the day, S.A.L.

There are several reasons for that. Professionally, I want to make sure that the work I put into booking a show doesn’t end when the contract is signed. I want to see it through. I want to make sure the artist, the promoter, the production, and ultimately the fans get the experience they were promised.

But personally? I get to travel. Because of this career, I’ve had the opportunity to visit places I probably never would have otherwise. I’ve met people I may have never crossed paths with, and, honestly, some of my closest friendships were formed on the road.

It’s one of those unexpected gifts that comes with this crazy career. But there’s one place I’ve traveled to many times, not just for business, but throughout most of my life.

As a kid, Florida was the ultimate vacation destination. Disney World in Orlando. Busch Gardens in Tampa. South Beach in Miami. Daytona Beach. West Palm Beach. The Florida Keys. I even lived in Panama City Florida when I was around 14.

For generations of Americans, Florida has represented sunshine, escape, and a touch of paradise. But for those of us in Freestyle, Florida represents something else… Family!

For as long as I’ve been involved in this business, I’ve traveled to Florida for Freestyle events. I’ve seen this music performed in private parties, nightclubs, theaters, parks, amphitheaters, small pubs, and of course on the beach.

And now, thanks to promoters and concert companies such as Pacific Concert Group, Freestyle is filling some of the most magnificent arenas in the state.

This year, The Cover Girls had the opportunity to perform at two of them. On Friday, July 31, 2026, The Cover Girls joined an incredible lineup featuring Stevie B, Lisa Lisa, TKA, George LaMond, Judy Torres, Lisette Melendez, JJ Fad and the 69 Boyz at Orlando’s Kia Center, and the energy inside that building was absolutely amazing.

The fans showed up, and the artists definitely showed out. Then, the very next morning, we all climbed aboard the Freestyle Express bus and headed to Tampa, where we did it all over again, this time at the Yuengling Center.

Two cities. Two major venues. Two nights of Freestyle. And somewhere between those two shows, something became even more obvious to me. Florida’s Freestyle fans aren’t simply enjoying these concerts… They’re reliving them.

Now, the debate over where Freestyle originated has been going on for decades. I was born and raised in New York, so I can only speak from my own experience, and from that perspective, I’ve always believed Freestyle was born in NYC. But the story didn’t end there. Florida has long been a second home for New Yorkers.

For years, it was thought of as a retirement destination. But eventually, younger families began making the move too, searching for what they believed would be a better life. And if you’ve spent any real time in Florida, you know exactly what I mean.

You can’t walk ten steps without running into someone who says, “Yeah, I’m originally from New York.” And that brings me back to those concerts.

If I had to guess, I’d say at least 75% of the people in those crowds were original New Yorkers, and that’s what makes performing in Florida feel a little like home.

These aren’t simply fans coming out to hear songs they love. These are people coming together to revisit a wonderful part of their lives.

For a few hours, they get to go back. Back to the old neighborhood. Back to the clubs. Back to the friendships, to being young, and to a time when life was a little simpler with Freestyle as the soundtrack to their lives.

It feels less like a concert and more like a family reunion. And though the artists may be on stage, the memories are in the audience.

That’s the beautiful thing about Freestyle. The music doesn’t just remind us of where we came from… It takes us there.

And maybe that’s why performing in Florida feels so much different to so many of us. Because when we perform there, we’re not just entertaining the fans. In a strange kind of way, they’re entertaining us, too.

And for those who grew up in New York and found a second home in Florida, I bet they remind them that no matter how far they travel… a piece of home always comes along.

So thank you, Florida. Thank you for continuing to embrace this music. Thank you for keeping the memories alive. And thank you for making every visit feel a little less like a job, and more like coming home. We can’t wait to see you again.

How did you like this article? Did it resonate with you in anyway? If so, leave a comment below, we’d love to hear from you.

WHAT DOES FREESTYLE LOOK LIKE?

Like most artists, Freestyle artists take their look pretty seriously. And if you look closely, you’ll realize that their stage outfits are pretty intentional.

But could they be better?

No one can tell me that Freestyle artists don’t have style. Because they do. They really do.

Great music is, without a doubt, one of the most important ingredients in the success of a Freestyle artist. But that’s only half of the equation. The other half? Their image.

That’s right. Let’s take a look at some of the biggest superstars in the history of entertainment. Go all the way back to Elvis. Great music? Absolutely. But what about those outfits? They became part of who he was. You didn’t just hear Elvis, you saw Elvis.

And how ‘bout them Beatles? Their outfits may have been relatively simple, but what about the hair? Even that became part of their identity. And yes, hair counts too. Image is more than just clothing. It’s the entire package.

Let’s keep it going. Madonna. Michael Jackson. The Jackson 5. The Osmonds. Cyndi Lauper. Rick James. KISS. Prince. Lady Gaga. I could do this all day.

Different artists. Different genres. Completely different styles. But they all understood something incredibly important: Your image is without doubt part of your brand.

So with that said, let me ask you again… How important do you think an artist’s image is to their career? And more importantly, can we place Freestyle artists into that same category?

Are our Freestyle artists also playing the image game? And if not, should they? And is it too late?

Can changing or enhancing an artist’s image at this point have any impact at all on their career, positive or negative? I think it can.

Unfortunately, I’ve also seen posts from people who seem to have nothing better to do than criticize an artist’s outfit. But wait… Is that really what they’re doing?

Think about some of the artists I mentioned earlier. Do you think Michael Jackson, Prince, Madonna, Lady Gaga, or any of those other superstars ever received criticism about what they were wearing? Of course they did. But here’s the difference.

When those artists walked onto a stage, nobody questioned whether they were supposed to look different. They were artists. They were entertainers. They were supposed to stand out. And maybe that’s something worth thinking about when it comes to Freestyle.

I remember having a conversation with my wife, Angel, when we first started working together. At the time, we were trying to establish her as a solo artist because we had not yet reunited The Cover Girls. And part of that process meant having some conversations that can be a bit delicate. Especially when you’re talking about a woman’s wardrobe.

I remember giving her an analogy that, to this day, she’s never forgotten. I told her:

“If you can walk into a restaurant wearing the exact same outfit you performed in and nobody turns their head, then you dressed wrong for the stage.”

Now, let me clarify. I didn’t mean turning heads because someone thinks you’re attractive. I meant turning heads because something about you makes people stop and think: “Wow… who is that?”

So tell me. When you picture your favorite Freestyle artist, what do you see? Do you immediately recognize them? Can you picture what they wear? Do they have a particular style? Do they have something that makes them stand out?

And if you’re one of the many Freestyle artists most likely reading this article, I want to turn the question toward you.

What does YOUR image look like? When you walk through a restaurant in your show outfit, do people turn their heads? And if the answer is no, please don’t take that as criticism. Take it as an opportunity.

Because it’s never too late to evolve. Take some time and really look at yourself.

Go through those old stage photos. Look at the outfits you wore years ago. Look at what you’re wearing today. Then ask yourself:

“If this wasn’t me in this photograph, what would I think about this artist?”

What would you change? What would you keep? What could make it more memorable? What could make it more you?

And most importantly, what could make someone see you for the first time and immediately know… That’s the artist.

I want to be clear about something. I think our Freestyle artists are incredible.

I think they look amazing. I think they look youthful. I see the effort many of them put into their appearance, and I believe a lot of them are doing a fantastic job.

This isn’t about tearing anyone down. It’s about building our artists up.

Freestyle has survived for decades because of its music, its fans, and most importantly, the people who continue to carry it forward.

Our artists deserve to be seen as the stars they are. And sometimes, being a star means understanding that the audience doesn’t just hear you. They see you.

So to all of the Freestyle artists reading this…

Don’t be afraid to stand out. Don’t be afraid to evolve. Don’t be afraid to create an image that is uniquely yours. Because someday, someone may not remember exactly what song you performed… But they may remember exactly how you looked when you performed it.

And to the fans reading this, I’d genuinely love to hear your thoughts. Tell me what you think. But please, be thoughtful.

Remember, the artists you’re talking about are real people with real feelings. And if you’re a subscriber to the Freestyle Blast, then chances are you’re a Freestyle fan. And those are the voices I want to hear.

Because at the end of the day, this isn’t about judging our artists. It’s about celebrating them.

So tell me… what does Freestyle look like to you?