How Alyssa O'Toole Turned 'Dead-End' Jobs Into a Thriving $50K+/Month Creative Music Studio

From Hustle to Harmony: The Birth of Musicians Playground

When Alyssa O'Toole began her journey, she shuffled through an exhausting patchwork of jobs, from teaching $20 music lessons across town to brewing coffee at Dunkin' Donuts and stepping in as a CrossFit instructor. With a business degree in hand but little clear direction, she poured her energy into learning, earning, and, most importantly, creating the foundation for something uniquely hers. From dawn to dusk, Alyssa’s schedule was a blur—yet underneath it all was a dream she refused to set aside: building a space where adults could rediscover the magic of music.

The spark came when she connected the worlds of fitness and music in her mind. Why wasn’t there a 'gym' model for music—an environment built around regular social practice and self-betterment, free from performance anxiety? That simple question became the seed for Musicians Playground. In 2012, working out of a live/work Boston loft to keep costs down, Alyssa took a leap and began assembling her dream from scratch.

Bootstrap Beginnings: Grassroots Growth & Community First

With no startup capital or marketing budget, every growth tactic had to count. Alyssa poured herself into perfecting each lesson. Word-of-mouth buzz and genuine testimonials powered the earliest growth. Instead of focusing on just teaching scales, she guided students to rediscover creativity, confidence, and joy, reframing her offer as transformative, not transactional. Whenever possible, she hosted social gatherings for members, sparking a community spirit that turned clients into ambassadors. Partnerships with schools fizzled, but student events flourished, bringing new faces and new energy.

By the time she committed to a $10,000/month commercial lease in 2019, Musicians Playground was generating $200,000 in annual revenue—yet she still hadn't spent a dollar on paid ads. Instead, the foundation was trust, experience, and a carefully shaped message that resonated deeply with her target audience.

Scaling and Struggles: Lessons in Leadership and Letting Go

Entrepreneurship is its own form of education. Alyssa learned the hard way that being a superb musician or teacher doesn’t guarantee success as a business owner. Leadership demanded new skills: hiring, systems, finance, marketing, and making tough choices. A major challenge arose when she took on a massive lease without a full grasp of business fundamentals. The situation quickly transformed into a hands-on MBA, teaching her everything from profit and loss management to understanding marketing ROI. Those mistakes and late nights, though daunting, were the crucible in which Musicians Playground’s success was forged.

Today, Alyssa credits her business partner (who later joined, bringing consulting expertise) for helping fortify the company's systems and strategy. What started as her side hustle is now a thriving team effort with strategic plans to open a second Boston location in the near future.

Revenue, Resilience & Real Results

Since its earliest days, Musicians Playground has used a membership-based model, offering predictable monthly recurring revenue. Modest at first, revenue grew steadily: from $2,000 per month as a solo act, then $10,000, $20,000, and ultimately $50,000+ per month as the team and offerings expanded. Now, the studio is targeting $80,000 monthly revenue within the next year—a remarkable feat for a business rooted in creativity and connection.

What energizes Alyssa most isn’t just the numbers—it's seeing adults transform through music, community, and the confidence her studio inspires. Every risk, stumble, and small victory blends together into a living masterpiece—distinctly her own.

Advice for Aspiring Founders

Alyssa’s playbook is both practical and heartfelt. Future founders should begin with a business plan, test ideas in low-risk ways before committing to heavy expenses, and track critical numbers from day one. Investing in the right technology and staying close to your customer base are essential. When it comes to mentors and agencies, she stresses the importance of choosing those with real, relevant experience. And emotionally, she advises learning to separate your self-worth from your business’s ups and downs—a lesson that took her years to internalize.

Though her path was far from direct—and often felt as if she was inventing it mid-flight—Alyssa O'Toole’s journey is proof-positive that grit, creativity, and a relentless commitment to community can transform a side hustle into a sustainable, flourishing business.