The Legendary Leaders Podcast · 2026-05-12 · 1h 10m
What if the success you spent three decades building disappeared overnight - and the hardest part wasn't the money, but knowing who you were without it? In this honest, unhurried episode of Legendary Leaders, host Cathleen O'Sullivan is joined by Scott Proposki - photographer, entrepreneur, author, and business coach based in Boston, Massachusetts. For nearly three decades, Scott built one of the most recognisable event photography businesses in North America: 52 people, eight-figure revenue, and a client list that included National Geographic, the White House, Sports Illustrated, and the NFL. Then 2020 arrived, and almost overnight, it was gone. Scott and Cathleen explore what it really costs to stop being the craftsperson and become the CEO, why growing fast can quietly hollow out the thing you loved, how depression after business loss is a grief that doesn't get enough airtime, and what a single conversation with a coach unlocked in his next chapter.
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