What really powers a legendary music career: luck or preparation? We sit down with an entertainment attorney whose five-decade journey runs from backstage nerves with a young Olivia Newton-John to helicopter clauses for Kenny Rogers, quiet rebuilding with Reba after tragedy, and complicated exits that still end in respect. Along the way he shows how trust-first relationships turn into durable deals, why the best counsel plans five to ten years ahead, and how to spot the moment when a flashy offer serves commissions over careers.

The stories move fast and cut deep. You’ll hear about staging leverage to win real contract value, navigating the delicate artist–manager–lawyer triangle, and drawing bright lines when a manager’s incentives collide with an artist’s future. We break down how legacy contracts still drag around breakage and packaging deductions, then collide with today’s internet uploads, streaming statements, and AI clones. He shares practical steps for protecting catalogs, from constant monitoring to decisive takedowns, and explains the gray zone no one foresaw: when an AI “new” master touches an old deal.

What stands out most is the humanity: 50 years of brother-sister rapport with Olivia, chameleon genius and honest breakups around Quincy Jones, and the steady hands who kept doors open—Conway Twitty, Jimmy Bowen, and others who believed before the ink dried. If you care about how artists actually build a life in music—contracts that age well, teams that align incentives, and careers that sustain both stage and family—this conversation is a field guide wrapped in unforgettable moments.

If this resonated, follow the show, share it with a friend, and leave a quick review so more listeners can find it. Got a question for a future episode or a story of your own? Send it our way at jfranzy.com and join the conversation.

Episode Links

• John Mason: https://www.johnmasonlaw.com/
• Crazy Lucky: https://www.johnmasonlaw.com/crazy-lucky-the-book
• Bob Bullock: https://jayfranze.com/episode28/

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