Jules Sobion: 20 Years Gambling on Carnival — Why Caesar’s Army Is Changing

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For 20 years, Jules Sobion has helped shape some of the Caribbean's most unforgettable Carnival experiences through Caesar's Army. But behind the sold-out events, spectacular productions and international success is a business he describes as “the casino.”

In this revealing conversation on The Corie Sheppard Podcast, Jules explains why producing events is such a high-stakes business, the challenges of building Caesar's Army, and why he's now preparing to take the brand in an entirely new direction.

🎧 THE CONVERSATION CONTINUES ON PATREON

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ABOUT THIS EPISODE

From the early days of Radioactive, Players and J3 to building Carnival experiences across Trinidad and Tobago, Barbados, Jamaica and beyond, Jules shares the remarkable journey behind one of the Caribbean's most recognizable entertainment brands.

He recalls the excitement of Rihanna attending one of his events, the international expansion that brought Caribbean culture to new audiences, and the difficult lessons learned from event failures, public criticism and changing consumer expectations.

But this conversation goes far beyond Carnival.

Jules opens up about his father, former Attorney General Keith Sobion, who became his first investor, mentor and greatest influence. He reflects on losing his father in 2008, the importance of family, and how becoming a father himself has changed his perspective on life, business and legacy.

Now, after two decades of building Caesar's Army, Jules shares his vision for a Caribbean Army — a movement aimed at taking Caribbean creativity, culture and experiences to the world.

IN THIS EPISODE:

• Why Jules describes the event business as a casino
• The financial risks behind Carnival's biggest parties
• The rise of Caesar's Army and its reputation for exclusivity
• What event promoters can learn from failure and public backlash
• Why Caesar's Army is evolving into a Caribbean Army
• Stories involving Rihanna, Usain Bolt and international Carnival experiences
• The early days of Radioactive, Players and Trinidad's party scene
• How Keith Sobion shaped his son's business philosophy
• Losing his father, finding purpose and embracing fatherhood
• The future of Caribbean culture on the global stage

The Corie Sheppard Podcast is a trusted space for meaningful, Caribbean-rooted conversations that connect generations, challenge norms and uplift our culture.

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