The Art of Succession · 2025-04-01 · 60 min
In this episode of The Art of Succession podcast, host Barrett Young interviews Tom Gledhill, a former business owner, broker, and author who has successfully built and scaled four businesses. Listeners gain valuable insights into business scaling, valuation, and exit planning from his decades of experience spanning from early technology adoption to sophisticated exit strategies. From Engineer to Software Entrepreneur Tom shares his journey from electrical engineer to software entrepreneur in the healthcare industry during the 1970s, when computers were still large and uncommon. His company developed administrative software for outpatient clinics, facing initial challenges selling technology to medical practices unfamiliar with computers. Tom describes overcoming the "selling a rifle to a caveman" challenge through persistent cold calling and building referrals. The introduction of the IBM PC in 1980 was transformative, allowing smaller practices to afford their networked systems. By focusing on recurring revenue through maintenance contracts and continuously improving their product based on customer feedback, they eventually grew to 3,000 clients across the Northeast.
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