How Italian Clothing, Trolleys in New York, Personalized Songs, and a Jetski Led to 3 Exits

Dave Pike is the Founder and former CEO of New York Trolley Company, an event transportation business serving New York City. A strategy and operations leader with 17 years of experience, Dave has built, scaled, and successfully sold three companies spanning apparel, transportation, and AI-powered personalized music. He is also the author of The New Startup and a mentor to early-stage founders through the Founder Institute. In this episode… Building a successful business is less about finding one perfect idea and more about testing, adapting, and knowing when to move on. Entrepreneurs who validate demand early, stay close to customers, and prepare for an eventual sale can make smarter decisions as they grow. What does it take to build, scale, and successfully exit multiple businesses? For serial entrepreneur and strategy and operations leader Dave Pike, the answer starts with testing an idea before investing too heavily in it. Across three successful businesses, that approach helped him learn what customers actually wanted, adjust his strategy, and grow with greater confidence instead of relying on assumptions. Dave carried that same mindset through each stage of entrepreneurship, using what he learned from the market to decide where to invest, when to adapt, and when it was time to sell. His experience proves that disciplined testing can become the foundation for smarter growth and stronger business decisions. In this episode of Growth + Exit, Heather Bennett talks with Dave Pike, Founder and former CEO of New York Trolley Company, about building, scaling, and selling businesses. Dave shares how to validate business ideas, identify the right customers, and prepare for a successful exit. He also discusses marketing lessons, due diligence, entrepreneurship, and the inspiration behind The New Startup.