People often assume that if an artist is available, all you have to do is make a phone call, agree on a fee, and they’re on a plane to South Florida. If only it worked that way.

Here’s a little insider secret...

An agent has one primary job: to get the best possible deal for their client. That’s exactly what they’re supposed to do. Their responsibility is to maximize income, secure favorable terms, and make sure their client is spending their time where it makes the most financial and professional sense. I genuinely respect that because, if I were the artist, I’d want someone doing the same for me.

But that also means they don’t just look at the dollar amount on the offer.

They look at where the artist is the day before. They look at where they’re going next. They look at airfare, hotels, ground transportation, production costs, lost opportunities, and whether accepting your offer prevents them from taking another engagement.

One of the biggest factors is routing.

Let’s say an artist is performing in Orlando on Friday and Atlanta on Sunday. Suddenly, a Saturday night in South Florida makes a lot of sense. The flights are already happening, the travel costs are lower, and everyone wins.

Now imagine asking that same artist to fly from New York to Fort Lauderdale for one performance and then fly right back home. Even if the performance fee is exactly the same, the overall cost can be thousands of dollars higher. That’s why you’ll often hear presenters talk about finding “fill-in dates” or “routable dates.” Those dates can literally be the difference between landing an artist and having to pass.

It’s also why some shows seem to come together overnight. Sometimes we’ve been working on an artist for months, and then another booking suddenly appears nearby. Everything lines up, and within a day or two, a deal gets done.

At Gray Box Theater, my philosophy has never been to simply book talent.

I want to build relationships.

I want artists, agents, managers, musicians, and their teams to leave saying, “That was one of the best experiences we’ve had.”

That means treating people well, communicating clearly, running a professional venue, paying people on time, and creating an environment where they genuinely want to come back. Those relationships matter, and over time they make all the difference.

Besides... who doesn’t want to spend a few days in beautiful South Florida during the winter? ☀️🌴

Speaking of relationships, I hope you’ll join us this Monday from 6:00–8:00 p.m. at Hunters for our Gray Box Theater happy hour. We’ll also have a card for everyone to sign that we’ll be sending along with flowers to Rosie O’Donnell in celebration of the opening of her new one-woman show, which I’ll be attending on the 25th.

Whether Rosie ever performs at Gray Box Theater or not, I want her to know she has an entire community in South Florida that appreciates her incredible career and is cheering her on. And who knows... maybe one day those relationships will bring her to our stage.

I hope to see you Monday!

As Gray Box continues to grow, so has the number of stories worth telling.

That’s why we’re making a change.

Going forward, many of these updates will be shared here on Substack. This gives us a better place to tell the stories behind the performances, introduce you to the incredible artists we work with, celebrate our volunteers and supporters, share our victories (and yes, sometimes our setbacks), and give you a genuine behind-the-scenes look at what it takes to build a theater that belongs to the community.

Don’t worry, we’ll still send important announcements and ticket information by email. But if you’ve ever wondered what happens between opening nights, this is where you’ll find it.

Thank you for joining us on this adventure. We’re glad you’re here.

Three Ways to Be Part of What We’re Building

When we first opened the doors to Gray Box Theater, our goal wasn’t simply to create another performance venue. We wanted to create a place where people could gather, connect, laugh, think, and experience authentic stories together.

Every week that vision becomes a little more real.

As we head into the second half of summer, I wanted to share a few exciting updates and invite you to be part of what’s coming next.

🍸 Join Us This Monday @ Hunters Nightclub!

Some of our best ideas don’t happen in board meetings.

They happen over a drink.

They happen in conversations before a show.

They happen when someone says, “Have you ever thought about...”

That’s exactly why we’re hosting our first Behind the Curtain Community Happy Hour.

📍 Hunters Nightclub – Wilton Manors
📅 Monday, July 20
🕕 6:00 PM – 8:00 PM

This isn’t a fundraiser. It isn’t a formal presentation.

It’s simply an opportunity for us to spend time together.

Meet the Gray Box team, chat with the people behind our programming, share ideas for future performances, ask questions, tell us what you’ve loved, and what you’d like to see next.

We’ll also have our community survey available, and thanks to our friends at Hunters, your first drink is on the house when you complete it.

Whether you’ve attended one performance or twenty, we’d love to see you there.

🎬 One Night Only: Inside the Oasis

On Monday, July 27, Gray Box Theater will host a special screening of Inside the Oasis.

Many people know The Oasis as one of South Florida’s most iconic gathering places.

Far fewer know the remarkable story behind it.

This documentary celebrates not only a legendary venue, but the people, friendships, and history that made it such an important part of our community.

Events like this remind us that theater isn’t just about what’s happening on stage. Sometimes it’s about preserving history, sharing memories, and bringing people together around stories that deserve to be told.

I hope you’ll join us for what promises to be a meaningful evening.

Tickets are only $10 ($12.45 with the fee) and available here.

🗽 Broadway Bound!

One announcement has exceeded every expectation we had.

Our inaugural Broadway Weekend in New York City now has 24 people signed up!

When we first announced the trip, I honestly hoped we’d have enough interest to make it happen.

Instead, we’re assembling an incredible group of theater lovers who will experience Broadway together, enjoy behind-the-scenes experiences, meet artists, and create memories that simply aren’t possible from a theater seat alone.

Something tells me this may become one of Gray Box’s newest traditions.

You have until July 31 to register here.

Building More Than a Theater

People often ask me what success looks like.

Yes, sold-out performances are wonderful.

But success is also watching strangers become friends in our lobby.

It’s seeing local artists discover a home.

It’s hearing someone say, “I never imagined Wilton Manors would have something like this.”

Every show, every volunteer, every donor, every audience member, and every conversation helps us build something much larger than a theater.

We’re building a community.

Thank you for believing in Gray Box Theater and for being part of this journey from the very beginning.

I hope to see many of you at Hunters on Sunday, at Inside the Oasis on July 27, and perhaps even walking through Times Square with us this fall.

After all...

The best stories happen behind the curtain.