15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall

In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jason Pearsall, CEO of Club Caddie Holdings, about his evolution from startup founder to a private equity-backed business leader. Jason shares his lessons from two successful exits, the pivotal shifts in his golf technology business, and the art of balancing data with instinct. Jason shares his take on the importance of defining your ideal customer profile and a focus on due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but finding partners aligned with long-term goals while transforming traditional industries with technology.