We’re excited to introduce you to the always interesting and insightful Stephen Grybowski. We hope you’ll enjoy our conversation with Stephen below.

Stephen, thanks for taking the time to share your stories with us today How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? We’d love to hear the backstory the illustrates how you grew the firm

When we started The Rock and Roll Playhouse, the goal was simple: to create a space where families could experience live music together, introducing children to the magic of iconic artists like The Beatles, Bob Marley, and the Grateful Dead. What began as a series of small shows at Brooklyn Bowl quickly grew into a national program, but that growth came with its share of twists, challenges, and valuable lessons.

The music industry, like many others, is built strongly on relationships. We’ve been very lucky in that our founder, Peter Shapiro, happens to be one of the most beloved men in the music industry. His connections and reputation opened countless doors for us, from securing iconic venues to collaborating with talented artists.

That said, scaling wasn’t just about adding more shows and more venues; it was about growing our musical community. Early on, we recognized that parents wanted more than just entertainment—they wanted meaningful experiences with their children. We leaned into this by curating interactive, engaging elements during performances and forming strong partnerships with like-minded venues and organizations. Venues loved the idea of daytime, family-friendly programming when their rooms were usually dark, that brought new audiences into their spaces and this synergy became a cornerstone of our expansion strategy.

Expanding beyond New York was exciting but not without hurdles. Finding the right venues, hiring local talent, and maintaining quality across all shows required meticulous attention to detail. On any given weekend we might have 15 to 20 shows in just as many states, with full bands and MCs working for us at each. It’s a massive undertaking to keep everything organized. We have also learned to pilot smaller, one-off events in new cities before committing to a full calendar of shows to make sure every aspect of our show works in the market.

Scaling The Rock and Roll Playhouse wasn’t a straight line, but rather a series of experiments, adjustments, and a relentless focus on what mattered most: connecting families through music.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m Stephen Grybowski, and my career has been dedicated to creating spaces and moments where music and community come alive. I’ve been fortunate to work at the intersection of live events, marketing, and mission-driven projects that connect people through shared experiences.

I started in the music industry with an interest in grassroots marketing and event coordination roles, driven by a love for live music and the way it brings people together. Over the years, I’ve grown into leadership positions across some of the most iconic brands and events in the industry. Currently, I serve as the Senior Director of Marketing and Family Programming at Dayglo Presents, overseeing marketing for projects like The Bearsville Theatre and Relix Media Group, while also acting as the Executive Director of The Rock and Roll Playhouse.

What I bring to the table is a knack for scaling ideas into national brands. For instance I’ve helped transform The Rock and Roll Playhouse from a small program of family-friendly concerts into a beloved, nationwide phenomenon. From curating interactive family music experiences to crafting marketing strategies, my focus has always been on creating opportunities for connection and joy.

One of my proudest achievements is co-founding Backline, a nonprofit dedicated to providing mental health and wellness resources to those in the music industry. Backline was born out of a recognition that the music community faces unique challenges—from the pressures of touring to the instability of freelance work—and that mental health support tailored to these experiences was critically needed. Through Backline, we’ve created a space where artists, crew members, and industry professionals can access counseling, peer support, and wellness programs designed to address their specific needs. Seeing how the organization has grown and the lives it has touched has been one of the most rewarding experiences of my life.

Have you ever had to pivot?

When the COVID-19 pandemic forced live music venues to close, The Rock and Roll Playhouse faced the challenge of keeping our mission alive: bringing families together through the power of music. With in-person events on hold, we quickly pivoted to livestreaming concerts through a series we called Live From The Playroom, creating a new way for families to connect and enjoy music from the safety of their homes.

This pivot not only kept our community engaged but also opened the door to incredible collaborations with artists who were similarly stuck indoors. Our livestream series featured memorable performances from an amazing lineup of musicians, including The Revivalists, The Wood Brothers, The String Cheese Incident, and so many more. Their participation brought new energy and excitement to our programming, while also showcasing the power of music to unite us even in isolation.

How’d you meet your business partner?

My journey with Peter began in the fall of 2012, when I started as a Marketing intern for Relix Media Group, which is where I first encountered Peter Shapiro. From the moment I started, I knew I was going to intern for as long as it took to earn a role working for Peter in some capacity—and I’ve never looked back. What started as a simple internship evolved into a career filled with exciting collaborations and impactful projects that I truly could never have dreamed of when looking back.

Contact Info:

• Website: https://therockandrollplayhouse.com
• Linkedin: https://www.linkedin.com/in/sgrybowski/