Sam sits down with Jimmy Cundiff, a Southern-born former Hollywood agent who climbed from the William Morris mailroom to representing major talent and now works with Triumph Motorcycles to connect brand and entertainment culture.

They talk about the evolution of the entertainment industry, building trust in a business built on deals, and how authenticity and Southern roots carried Jimmy through decades in Los Angeles. From representing stars to introducing Triumph to the screen, Jimmy shares lessons on mentorship, integrity, and creative longevity.

Filmed live inside The Isle of Triumph during the 20th anniversary of Barber Vintage Fest.