My name is Alyssa O’Toole, and I’m the founder of Musicians Playground, an adult music school and community in Boston. Before launching the business, I was hustling through multiple jobs—teaching music lessons across the city, working as a CrossFit instructor, and more—all while chasing my dream.
With over 20 years of experience as a pianist, I knew music was my calling. In 2012, I began building what would become a unique space where adults could pursue their passion for music in a supportive and dynamic environment, eventually growing it into a $1M business.
I’m sharing my story to inspire fellow entrepreneurs and musicians like you to keep going, even when the path isn’t clear—because big dreams can start with small steps.
Building Musicians Playground from the Ground Up
When I started Musicians Playground, it was just me, my piano, and a vision. I was traveling to people’s homes offering private lessons, using whatever free hours I had to build something I knew the world needed—though I didn’t know then just how big it would become.
Today, Musicians Playground is a vibrant, brick-and-mortar community for over 200 music-loving adults in Boston. We specialize in music as a form of wellness, and we’re proud to be the first-ever gym for musicians.
Our 3,000 sq ft facility functions just like a fitness club—except instead of treadmills, we offer over 100 monthly group classes in piano, voice, and guitar, one-on-one lessons with expert instructors, and space for creative co-working and practice. We even partner with corporations to offer music-based wellness and host unforgettable team-building events.
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What Sparked Musicians Playground: My Passion for Music and People
The inspiration for Musicians Playground came from my own dual passions: athletics and music. I remember asking myself, Why isn’t there a place like a gym—but for musicians? I knew how much music impacted my mental, emotional, and physical health, and I believed others needed a space like this too—especially adults.
As we get older, play, connection, and creativity can slip through the cracks. We’re busy working, adulting, and navigating a world where apps and screens dominate our social lives. I spoke to so many people who loved music—whether they wanted to return to it after childhood, or always wished they’d had the chance to start. I knew I had to build a space where adults could explore music safely, joyfully, and socially—no judgment, no pressure.
How Musicians Playground Became a Community-Driven Music School for Adults
I didn’t start with funding or a business degree. I started with my savings, some hard-earned teaching experience, and a lot of hustle. In fact, for the first four years, I lived in the storage area of my business, and then a walk-in closet just to conserve resources and reinvest every dollar back into what I was building.
My initial strategy was to grow as organically as possible. I leaned into my natural love of people and connection, and I hosted events that brought students together. We rolled out group classes early, which helped us create a social experience around music. A coach once told me, People come for the content, but they stay for the community. I didn’t know it at the time, but I was already building that retention engine from the ground up.
By 2019, we were ready to scale—and we made our first big investment into paid marketing (primarily Google). That helped us drive enough volume to take a major leap: moving into a stunning new space in downtown Boston that was four times the cost of our previous location. It was terrifying—but necessary.
It forced me to get serious about becoming a real business owner. I gave myself a crash course MBA in operations, financial strategy, and leadership. No textbooks—just the real-world version, complete with 2am anxiety and high-stakes decision-making.
Lessons in Scaling a Purpose-Driven Business
There’s no one-size-fits-all playbook for getting to $1M in revenue, but here’s what I can tell you: the hardest parts weren’t about marketing or pricing. They were about support—first not having enough, then not having the right kind. It was about learning what to focus on, when, and for how long.
It was about understanding the economics of the business deeply: how to track, interpret, and act on data to make smarter decisions. And, perhaps hardest of all, it was about letting go—of systems, habits, or people that no longer aligned with the business as it evolved.
Growth is messy—especially when you’re running a people-centered business. You can’t scale cleanly without hitting friction. You just learn to move through it faster and with more ease and clarity.
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How Musicians Playground Reached $1M and Is Scaling Toward Monthly Recurring Revenue
We hit our first $1M in revenue a while ago, though I’m not exactly sure when it happened. But what I do know is that we’re now on track to hit $1M in monthly recurring revenue within the next 12–18 months—and that is the milestone I’m most proud of. It reflects a level of sophistication, consistency, and impact that I never would’ve imagined in those early days, sleeping behind a curtain in the studio just to keep the lights on.
It’s been made possible thanks to an incredible team and, more recently, the addition of my first formal business partner, David. With his background in consulting and operations, we’ve been able to level up our systems and strategy in a big way.
Advice I Have for Fellow Founders
If I had to boil my advice down, it would be this:
- Don’t stop. You’d be amazed what happens when you stay in the game one day longer—then do that for 10 years.
- Get the right support. Not just anyone who says they’re a coach. Someone who’s done what you’re trying to do. Results matter.
- Build slow if you need to. There’s no shame in building something brick by brick. I’ve had people tell me my model was “too slow” because it wasn’t a quick e-commerce flip or drop-shipping scheme. But here I am, years later, with a thriving company I love, real impact, and a possible exit one day worth far more than those short-term plays.
Your business should be aligned with you—your gifts, your passion, your purpose. Don’t let someone else’s values (money, speed, ego) distract you from your own.
Wrapping Up
The same lessons that helped me grow Musicians Playground from a storage closet to a seven-figure brand are the ones I now get to share through my work as a consultant for music studio owners and creative entrepreneurs around the world.
It’s incredibly fulfilling to not only serve the communities my business touches, but to help other founders create thriving communities of their own.So if any of this resonates—or if you’re looking for support from someone who’s truly walked the path—reach out—I’d love to help.
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