Episode 301 – Preparing Advisors for the AI Era at Future Proof Citywide with Chris Cherry

Chris Cherry, Head of Partnerships at Future Proof, joins us to talk about Future Proof Citywide and how it expands on the Future Proof Festival model by moving into Miami Beach, allowing the event to grow beyond the Festival’s 5,000-person limit while keeping the same outdoor, relaxed, anti-conference feel. Citywide also introduces a rotating theme structure — Invest, Build, Grow, and Live — with AI as the central focus for 2025, reflecting how quickly it’s becoming part of industry conversations.

Chris highlights why Citywide delivers real ROI: the breakthrough meeting program, where attendees pre-select and schedule high-quality matches rather than relying on chance encounters. Those curated meetings have led to major client wins and even career-changing outcomes. New this year is a 20,000-square-foot AI Playground, expanded partner activations across Miami Beach, and returning experiences like the women’s lounge. Chris hopes attendees leave with confidence in using AI — and a clear sense that stepping into these conversations is no longer optional.

Resources: Future Proof

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