Billy McFarland joins Due To My Role to walk through his most aggressive idea yet... a live-streamed jet-ski expedition from Utila, Honduras to Venezuela, departing shortly after the Super Bowl and expected to take 17 days coast-to-coast.

The plan is simple and insane: beat Wall Street to Margarita Island by jet ski, acquire beachfront land before institutional capital arrives, host a high-profile “freedom concert,” drive attention and value, then sell the land at a premium. Three seats are offered at $250,000 each, with a 58-foot chase boat, medical crew, and film team following the entire journey, all streamed live.

PE Guy presses McFarland on the obvious questions: risk, legality, safety, and whether this is vision or repetition. McFarland doesn’t dodge it. He openly acknowledges pirates, narcos, rogue governments, and the fact that his safety “is not guaranteed” — arguing that risk is the leverage.

Beyond Venezuela, the conversation goes deeper. McFarland talks candidly about serving four years in prison, joking that parts of it felt like a “forced vacation”, a rare pause from work while also explaining how incarceration reshaped his tolerance for fear, reputation damage, and public opinion.

Most importantly, he outlines a clear pivot away from nightlife and one-off festivals. Festivals, he says, are marketing tools not the endgame. The real ambition is hospitality: permanent hotels in places like Utila or Venezuela, smaller curated groups, and productizing his ability to connect brands with talent at scale. He also discusses efforts to buy back the Fyre brand and reframe it around owned assets instead of spectacle.

This episode isn’t about rewriting history. It’s about what happens after the penalty box — when reputation is damaged, capital is skeptical, and the only way forward is risk, attention, and relentless motion.

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