Community Highlights: Meet Joe Costello of Onstage Entertainment Group, LLC

Today we’d like to introduce you to Joe Costello.

Hi Joe, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I grew up in the hospitality business. My father owned a sizable restaurant in Port Ewen, a small town a couple hours north of New York City. What made our location special was timing and geography, we were right on Route 9W, which at the time was the only road running north and south between New York City and the Catskills. During the golden age of the Borscht Belt, this stretch of road was bustling with travelers heading to the hundreds of resorts, hotels, and bungalow colonies that catered to families escaping the city.

As a kid running around that restaurant, I didn’t realize I was getting an education. We had live bands every weekend for special events and weddings, and I was absorbing everything, how to read a room, understanding acoustics, learning what works when you’re combining hospitality with entertainment. My father was an incredible tenor sax player, but I was mesmerized by the drummers. That became my instrument, and I played throughout my childhood, all through college at SUNY Fredonia’s School of Music, and later in jazz and blues clubs around NYC.

I’ve always been an entrepreneur. I started and ran three successful businesses that had nothing to do with music, but in 2013, everything came full circle when I founded Onstage Entertainment Group.

The lightbulb moment happened while I was performing seven nights a week around the Phoenix valley. My band landed a coveted residency at The Montelucia Resort & Spa every Friday and Saturday night. As we grew in popularity and started booking corporate events and out-of-town weddings, I faced a problem: how could we keep our residency when we had to be somewhere else?

That’s when it clicked. If I could make our absence seamless and painless for The Montelucia’s management, we could keep the residency and take higher-paying gigs. I knew exactly what made us successful at that resort, the dress code, the load-in procedure that didn’t disturb dinner guests, the volume levels, the song selections that worked for their diverse clientele. I could find the perfect replacement band because I understood every detail that mattered.

That was the birth of Onstage.

Other resorts started calling, asking me to provide the perfect entertainment for their specific venues. Our resort clientele grew rapidly, and we were off to the races. But what really transformed our business model was when Destination Management Companies (DMCs) would bring their corporate clients for site visits, walk through one of our resort properties, and see our entertainers performing. Suddenly, doors opened to the corporate events world.

What started as a music entertainment company evolved into a one-stop solution for all things entertainment.

Today, we have over 900 entertainment options on our roster from across the country, and we supply entertainment in all the major destination markets, Las Vegas, Orlando, Chicago, New York City, San Diego, Phoenix, San Francisco, Nashville, Atlanta, Dallas, New Orleans, Washington DC, Boston, Denver, Miami, and Los Angeles.

We’ll continue to put down roots in new cities as we expand across the US, and as our clientele grows, working on events overseas is the next logical step. That kid watching drummers in his father’s restaurant never imagined he’d build a national entertainment company, but looking back, every piece of the puzzle was preparing me for exactly this.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Has it been smooth? Not even close. Building this business has been one of the most challenging things I’ve ever done.

In the beginning, the biggest hurdle was credibility. I was asking high-end resorts and corporate clients to trust me with their most important events: weddings, galas, executive retreats. One bad band, one unprofessional performer, and I could lose everything I’d built. The weight of that responsibility was enormous, especially in those early years when every gig felt make-or-break.

Quality control became an obsession. When you’re managing hundreds of entertainers across multiple cities, you can’t be everywhere at once. I’ve had bands show up in jeans when the dress code was formal. I’ve had musicians who couldn’t read the room and played way too loud. I’ve dealt with no-shows, equipment failures, and personality conflicts. Each mistake felt personal because my name was on it.

The financial side was brutal too. Entertainment is a cash-flow nightmare: you’re paying performers immediately while waiting 30, 60, sometimes 90 days to get paid by clients. There were months in the early years when I wasn’t sure how I’d make payroll. I remember lying awake at night doing mental math, figuring out which bills could wait and which couldn’t.

Scaling nationally brought a whole new set of problems. Thank God for the internet and live video footage, because I personally vet every single performer on our roster, regardless of what city they’re in. But building relationships with venues remotely? That’s a different challenge entirely. It required countless phone calls, site visits when possible, and learning to build trust from a distance.

And then COVID hit. Our entire business model, live entertainment at in-person events, vanished overnight. Watching everything we’d built go dark was devastating. But it also forced us to innovate, pivot, and come back stronger.

Every challenge taught me something. Every failure made our systems better. The struggles weren’t smooth, but they shaped who we are as a company today.

Alright, so let’s switch gears a bit and talk business. What should we know?
Onstage Entertainment Group is a full-service entertainment company specializing in corporate events, destination weddings, and luxury resort entertainment. We’re not just a booking agency; we’re a complete entertainment solution that handles everything from initial consultation to day-of-event coordination.

Here’s what sets us apart: I personally vet every single entertainer on our roster. Every one. With over 900 entertainment options spanning musicians, DJs, specialty acts, and performers across the country, that’s no small task. But it matters because I’m not just looking at their talent; I’m evaluating professionalism, punctuality, how they dress, how they interact with clients, and whether they understand the nuances of high-end events. I can watch their live performances online, review their setlists, and assess whether they’ll be the right fit for our clients’ specific needs.

My background gives us a unique edge. I grew up in the hospitality business and spent years performing professionally, so I understand both sides of the equation. I know what venue managers need, what event planners are looking for, and what makes a performance successful. It’s not just about great music; it’s about reading the room, understanding acoustics, respecting load-in procedures, maintaining appropriate volume levels, and seamlessly adapting to the energy of an event.

We operate in all the major destination markets: Las Vegas, Orlando, Chicago, New York City, San Diego, Phoenix, San Francisco, Nashville, Atlanta, Dallas, New Orleans, Washington DC, Boston, Denver, Miami, and Los Angeles. But we’re not a faceless national company. Every client gets personalized service, and every event is treated like it’s the most important one we’ve ever done.

What am I most proud of? Our reputation. We work with some of the country’s top Destination Management Companies and luxury resorts because they know when they book through Onstage, everything will be handled flawlessly. No surprises, no drama, just exceptional entertainment delivered professionally. Our clients return to us year after year, and that loyalty means everything.

We’ve also evolved beyond just music. We now provide everything from string quartets and jazz trios to celebrity impersonators, aerialists, magicians, and interactive entertainment. If a client can dream it, we can deliver it.

But here’s what I really want people to know: we’re not just vendors. We’re partners. When you work with Onstage, you’re working with someone who genuinely cares about making your event unforgettable. I’ve been on stage. I’ve managed venues. I know what’s at stake. And I’ll move heaven and earth to make sure every detail is perfect.

Any advice for finding a mentor or networking in general?
Honestly? I never had a traditional mentor in the way most people think of one. But looking back, I had something just as valuable: I was surrounded by people I could learn from if I paid attention.

Growing up in my father’s restaurant, I watched him navigate the hospitality business every single day. I saw how he handled difficult customers, how he built relationships with regulars, how he managed staff. I didn’t realize it at the time, but I was absorbing lessons that would shape how I run my business today. So my first piece of advice is this: don’t overlook the people already in your life. Parents, bosses, colleagues… observe how they handle challenges and what makes them successful.

When I was performing seven nights a week, I treated every venue manager, every event planner, and every hotel director as someone I could learn from. I asked questions. Why did this room have better acoustics? What made one event flow smoothly while another felt chaotic? What did they wish bands understood better? Those conversations weren’t just networking; they were education. And many of those people became advocates for my business when I started Onstage.

Here’s what has worked for me in networking: be genuinely helpful without expecting anything in return. When I started finding replacement bands for The Montelucia, I wasn’t thinking about building a company. I was solving a problem for people I respected. That authenticity created trust, and trust created opportunity.

Join industry organizations. Attend conferences. But here’s the key: don’t just collect business cards. Have real conversations. Remember what people tell you about their challenges. Follow up. Be the person who adds value to their network, not just someone looking to extract value from it.

And if you’re looking for mentorship, be specific about what you need help with. Don’t just ask someone to “be your mentor.” Ask if they’d be willing to grab coffee and give you advice on a specific challenge you’re facing. Respect their time. Come prepared with thoughtful questions. Most successful people are willing to help someone who’s serious and respectful of their expertise.

The entertainment and events industry is built on relationships. Your reputation is everything. Show up on time, do what you say you’ll do, and treat every interaction like it matters, because it does. The stage manager you help out today might be the events director at a major resort tomorrow.

Finally, don’t be afraid to reach out to people you admire. The worst they can say is no, and you’d be surprised how many people are willing to share their knowledge with someone who’s genuinely hungry to learn.

Contact Info:

• Website: https://osegllc.com
• Instagram: https://www.instagram.com/osegllc/
• Facebook: https://www.facebook.com/osegllc
• LinkedIn: https://www.linkedin.com/in/ceo-joe-costello/
• Twitter: https://x.com/OSEGLLC
• Youtube: https://www.youtube.com/@osegllc

Image Credits
Jo Ellen Verna Portrait