Side Hustle Spotlight: Alyssa O’Toole and Musicians Playground

In the bustling city of Boston, Alyssa O’Toole has carved out a unique niche in the music education landscape. As the founder of Musicians Playground, a music studio designed like a gym for musicians, she offers adult hobbyists group classes in piano, voice, and guitar, alongside music-based team-building events. O’Toole’s journey is a testament to the power of passion, perseverance, and innovative thinking.

The Journey Begins: From Gig to Vision

Before launching Musicians Playground in 2012, Alyssa O’Toole was juggling multiple jobs to make ends meet. From teaching music lessons across the city to working as a CrossFit instructor and even serving coffee at Dunkin’ Donuts, her hustle was relentless. "I was doing anything and everything to get by," she recalls. This diverse experience, while sometimes daunting, equipped her with invaluable skills in grit, people management, and real-world problem-solving.

O’Toole’s inspiration for her side hustle stemmed from her lifelong love of music and teaching. With over 20 years of piano experience, she envisioned a space where adults could engage with music in a relaxed, social environment—similar to a gym for fitness enthusiasts. This idea blossomed into Musicians Playground, a community that emphasizes creativity, joy, and connection.

Laying the Groundwork: Initial Steps to Success

Launching Musicians Playground required strategic grassroots marketing. O’Toole focused on delivering exceptional experiences to her clients, believing that word-of-mouth would be her strongest ally. "People talk about things that make them feel good," she explains. By framing her offerings around transformation rather than mere instruction, she attracted a community eager for a creative outlet.

Early on, O’Toole experimented with partnerships but found that hosting social events for her students was the most effective way to build community. These gatherings fostered a sense of belonging and encouraged students to return, often bringing friends along. This organic growth laid the foundation for her business, which eventually expanded to include more teachers and services.

Learning Through Challenges: Navigating the Business Landscape

O’Toole’s journey was not without its challenges. One significant hurdle was the decision to sign a commercial lease that tripled her rent. Despite warnings from her advisor, she felt compelled to take the leap for growth. This experience forced her to develop a deeper understanding of business operations, financial literacy, and the importance of making informed decisions.

Reflecting on her early days, O’Toole wishes she had been more selective with the coaches and consultants she worked with. "I spent a lot of money on people who didn’t understand my industry," she admits. This realization has shaped her approach to mentorship and collaboration, emphasizing the importance of finding experts who align with her vision.

The Growth Trajectory: From Side Hustle to Sustainable Business

Musicians Playground has seen impressive growth since its inception. Initially earning a few thousand dollars a month, O’Toole’s business model focused on monthly recurring revenue (MRR), which provided stability as she expanded her offerings. Over time, her revenue climbed steadily, reaching $50,000 per month and beyond.

Today, Musicians Playground averages about 20% year-over-year growth, with plans to cross the $80,000 monthly revenue mark within the next 12 to 16 months. O’Toole attributes this success to her partnership with a business consultant who has helped strengthen their systems and operations.

The Joy of Entrepreneurship: What Keeps O’Toole Motivated

For O’Toole, the most rewarding aspect of running Musicians Playground is witnessing her vision come to life. "Every decision I make feels like another brushstroke on a decade-long masterpiece," she shares. The dynamic nature of entrepreneurship keeps her engaged, as each day presents new challenges and opportunities for growth.

Advice for Aspiring Entrepreneurs

Alyssa O’Toole’s journey offers valuable lessons for anyone considering a side hustle. Here are her top pieces of advice:

Create a Business Plan: Start with a solid business plan that outlines your vision, pricing model, target market, and growth strategy. This framework will guide your decisions and help you seek focused support.

Start Low-Cost: Look for creative, low-cost ways to launch your business. O’Toole began Musicians Playground from a live/work loft, allowing her to grow organically before committing to a commercial lease.

Track Everything: From the beginning, keep a close eye on your revenue, expenses, and customer metrics. Understanding your numbers early gives you a significant advantage.

Invest in Technology: Utilize tools that streamline your operations, such as financial software and customer relationship management systems. These technologies can save time and provide insights into your business performance.

Balance Heart and Structure: Building a business requires both passion and a solid structure. The sooner you establish both, the smoother your entrepreneurial journey will be.

Conclusion

Alyssa O’Toole’s story is a powerful reminder that with determination, creativity, and a willingness to learn, anyone can turn their passion into a thriving business. Musicians Playground stands as a beacon for adult musicians seeking community and growth, proving that the intersection of passion and entrepreneurship can lead to extraordinary outcomes. Whether you’re considering a side hustle or looking to scale your existing business, O’Toole’s insights provide a roadmap for success.