Julia Dougall, global music manager and creative entrepreneur, joins Stefan to talk about her journey from Jamaica to Cayman — and what it’s like managing internationally known artists, including Sean Paul.

They dive into the realities of working in a male-dominated industry, the role of emotional intelligence in business, and how Cayman’s creative community is evolving. Julia also shares why island life offers space to reset, refocus, and live more intentionally — especially in a post-COVID world.

Tim Rossiter joins Stefan to talk about his move from Australia to Cayman and the career shift that followed. After years in fund administration, Tim is exploring new ventures, from AI to education — and finding fresh purpose through community involvement.

They discuss what it’s like to step away from a long-standing role, the balance between work and wellbeing, and why Cayman’s lifestyle creates space to do both business and life differently.

Tara Neilsen, founder of Acts of Random Kindness (ARK), joins Michael Joseph to talk about the real — and often hidden — challenges facing families in Cayman. From homelessness to access to education, Tara shares what she’s seen on the ground, why ARK was created, and how kindness can lead to long-term change.

They also explore what community support really looks like, and why everyone has a role to play in breaking the cycle of poverty.