Send us Fan Mail

What happens when a chance conversation leads to one of Cape Cod's most unique new businesses?

In this episode of Monkey Business Radio, Chris Collins and Dennis "Bobby Downspout" Siggins sit down with Bill Russell, founder of Island Pickle in Mashpee. What began as a vision for Cape Cod's first dedicated indoor pickleball facility has quickly evolved into something much bigger—a destination built around community, entertainment, great food, and unforgettable experiences.

Bill shares how three decades in the corporate world, combined with years in the restaurant industry, prepared him to take a leap into entrepreneurship. Together, the conversation explores what it takes to launch a 37,000-square-foot startup, the importance of branding and marketing, learning from early mistakes, and why the best businesses never stop evolving.

Along the way, you'll hear discussions about building a regional brand, creating customer experiences that keep people coming back, and why successful entrepreneurs are willing to adapt their vision as they grow.

Whether you're a business owner, an aspiring entrepreneur, or simply someone who enjoys hearing the stories behind successful local businesses, this episode is packed with practical insights and inspiration.

In this episode:

• The story behind Island Pickle and its unexpected beginnings
• Why entrepreneurship is often built on opportunity and preparation
• Branding, marketing, and building awareness from day one
• Creating a destination instead of just another business
• Lessons learned during the first year of a major startup
• The power of community in building a lasting business