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From Dead-End Jobs to $50K Months: Musicians Playground Featured in Entrepreneur Magazine

From Dead-End Jobs to $50K Months: Musicians Playground Featured in Entrepreneur Magazine

How a Boston music studio became a national success story by treating music like fitness
We’re thrilled to announce that Musicians Playground and our founder, Alyssa O’Toole, have been featured in Entrepreneur Magazine, one of the world’s leading business publications. The feature story, “She Started a Creative Side Hustle While Working ‘Dead-End’ Jobs — Then Grew It From $10,000 to Over $50,000 a Month,” highlights our journey from a grassroots music teaching business to a thriving community that’s revolutionizing how adults learn and experience music.

The Musicians Playground Story: Building a ‘Gym for Musicians’

What started in 2012 as a side hustle while juggling multiple jobs — from CrossFit instructor to Dunkin’ Donuts server — has grown into Boston’s premier music studio and community space. As Alyssa shared with Entrepreneur, the breakthrough came from a simple question: “Why don’t we treat music the way we treat exercise?”

This insight led to creating Musicians Playground as a gym-like environment for musicians, where adult hobbyists can take group classes in piano, voice, and guitar without the pressure of traditional music lessons. It’s a space where creativity, community, and joy take center stage.

Key Milestones Highlighted in Entrepreneur

The feature captures several pivotal moments in our journey:

  • Starting with zero marketing budget: Growing to $200,000 in revenue through word-of-mouth and community building alone
  • Taking the leap: Signing a $10,000/month lease in downtown Boston that forced rapid business evolution
  • Sustainable growth: Achieving 20% year-over-year growth with plans to reach $80,000 in monthly revenue
  • Future expansion: Preparing to open a second location by late 2026

Lessons Learned Along the Way

In the Entrepreneur interview, Alyssa shared candid insights about the challenges of turning a passion into a profitable business:

The Identity Shift

“Being a great teacher requires empathy, presence and creativity. Being a great owner requires leadership, systems thinking, financial literacy and the ability to make hard decisions — often at the expense of the very work you once loved doing.”

The Power of Community

The secret to our growth wasn’t just teaching music — it was creating transformation. We focused on helping people reconnect with play, creativity, confidence, and joy. This message became magnetic, attracting adults who craved a creative outlet in their busy lives.

Business Wisdom Hard-Won

One of the most valuable lessons shared was about that pivotal $10,000/month lease decision. While it seemed risky at the time, it forced a complete business transformation. As Alyssa noted, “That year, my mentor joked I gave myself an MBA — and honestly, he wasn’t wrong.”

What This Means for Our Community

This national recognition validates what our students and team members already know: Musicians Playground is more than just a music studio. We’re a movement that’s changing how adults engage with music and creativity.

For our students, this feature reinforces that you’re part of something special — a community that’s inspiring people across the country to pick up an instrument and rediscover the joy of playing music.

For aspiring musicians and entrepreneurs, our story proves that with passion, persistence, and the right approach, you can turn your creative dreams into reality.

Advice for Aspiring Entrepreneurs

The Entrepreneur feature included valuable advice for anyone looking to start their own creative business:

  1. Start with a real business plan – Even if it evolves, having a framework helps you make smarter decisions
  2. Find low-cost ways to start – We began in a live/work loft before committing to commercial space
  3. Track everything from the beginning – Understanding your numbers gives you a huge advantage
  4. Invest in technology early – The right systems create space to focus on what really matters

Looking Forward: The Next Chapter

As we celebrate this milestone, we’re more committed than ever to our mission of making music accessible, social, and joyful for adults. With plans for expansion and continued innovation in how we deliver music education, the best is yet to come.

We’re grateful to Entrepreneur Magazine for recognizing our story and to Money Makers newsletter for featuring us as an inspiring side hustle success story. Most importantly, we’re thankful to our incredible community of students, teachers, and supporters who make Musicians Playground what it is today.

Join Our Growing Community

Inspired by our story? Whether you’re looking to reconnect with music, find a creative outlet, or join a vibrant community of adult musicians, we’d love to welcome you to Musicians Playground.

Ready to start your musical journey?

Want to learn more about our entrepreneurial journey?

Musicians Playground is Boston’s premier music studio and community, offering group classes in piano, voice, and guitar for adult hobbyists, along with music-based team-building events. Founded in 2012, we’re on a mission to make music as accessible and social as going to the gym.

For media inquiries, please contact info@musiciansplayground.com