5 to 50: Financial Strategies for Growing Companies · 2025-09-09 · 39 min
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 perspective on the importance of defining your ideal customer profile and the value of due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but about finding partners aligned with long-term goals while transforming traditional industries with technology.
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