Best Mike Joseph and Stefan Prior Podcasts (2025)

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S1 E9: George Loutus on Cayman’s Real Estate Shifts and Starting Fresh 30:22

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5M ago30:22

30:22

George Loutus, founder of Hive Law, shares why he left a long career at Maples and Calder to launch a fully remote law firm — and how that decision aligned with changes he was seeing in Cayman’s real estate market. He and Stefan talk about the rise of high-end property, the impact of population growth, and how cost pressures are reshaping developme…

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S2 E1: Jude Holland on Career Pivots, Culture, and Doing Real Estate Differently 37:57

5M ago37:57

37:57

Jude Holland sits down with Michael Joseph to talk about her path from the corporate world into real estate — and how life in Cayman reshaped her approach to work and relationships. They explore the value of integrity, the reality of what it takes to build trust with clients, and why being authentic matters more than trying to “sell.” Jude also sha…

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S2 E2: Acts of Random Kindness, A Journey of Love with Tara Neilsen 47:19

5M ago47:19

47:19

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 suppo…

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S2 E3: From Fund Administration to AI Ventures with Tim Rossiter 46:14

5M ago46:14

46:14

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 …

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S2 E4: Julia Dougall on Navigating the Music Industry from Cayman 33:44

5M ago33:44

33:44

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…

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S1 E6: Chris Kirkconnell on Family, Retail, and the Future of Georgetown 27:04

5M ago27:04

27:04

Chris Kirkconnell, VP of Operations at Kirk Freeport, joins Stefan to talk about his family’s legacy in Cayman and how luxury retail has grown and adapted over the years. They cover the shift from tourist-driven sales to a stronger local market, the global demand for brands like Rolex, and how supply chains have changed post-COVID. Chris also share…

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S1 E7: Family Dynamics in Wealth Preservation with Bernadette Carey 20:25

5M ago20:25

20:25

Bernadette Carey, partner at Carey Olsen, joins Stefan to unpack the often misunderstood world of trusts and wealth management — and how it all plays out within families. They explore why trusts matter, how family offices work, and the shift in how the next generation is approaching wealth, sustainability, and legacy. Bernadette also shares her per…

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S1 E8: Residency by Investment: Opportunities and Challenges with Cline Glidden 49:59

5M ago49:59

49:59

Cline Glidden, counsellor at Ogier and former Minister of Tourism, joins Stefan to talk about how Cayman balances legal clarity, cultural diversity, and economic growth. They dig into residency by investment, why Cayman’s legal system attracts high net worth individuals, and how immigration shapes the island’s future. Cline also shares insight on p…

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S1 E3: Georgina Lockstab on Money, Mindset, and Planning for the Future 54:07

5M ago54:07

54:07

Georgina Lockstab, a financial planner and fiduciary, talks with Stefan about how we think about money — and why that mindset matters more than most people realise. They cover everything from building trust with clients, to how emotions shape financial decisions, and why having a “margin of safety” is key in both investing and life. Georgina also s…

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S1 E4: Ian Jamison on Inward Investment, Community, and Life in Cayman 32:37

5M ago32:37

32:37

Ian Jamison joins Stefan to talk about inward investment, real estate, and what really shapes the experience of living and working in Cayman. They explore what makes commercial real estate here different, how infrastructure and legislation are influencing the market, and why prioritizing people — not commissions — is good business. Ian also shares …

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S1 E5: Navigating Family Life and Education in Cayman with Sophie Taylor 32:19

5M ago32:19

32:19

Sophie Taylor shares her story of moving from the U.K. to Cayman — and what it’s really like to start fresh as a parent in a new place. She and Stefan talk about the pull of island life, the challenges of relocating with children, and how Cayman’s sense of safety and community made all the difference. They also explore her podcast Truth of Motherho…

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S1 E1: James Whitaker on Cayman’s Path to Sustainability 50:39

5M ago50:39

50:39

James Whitaker shares why he left finance to focus on sustainability — and what Cayman needs to do if it wants a more secure, renewable energy future. From outdated regulations to missed opportunities in solar, James breaks down the real challenges holding Cayman back. He also talks about the role of government, the need for transparency, and why e…

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S1 E2: From Wall Street to West Bay – Tim Fury’s Story 57:04

5M ago57:04

57:04

Tim Fury shares how he went from being Donald Trump’s driver to launching a global trading firm — and why he chose Cayman as the place to slow down and reset. He talks about the personal health scare that changed everything, the shift in priorities post-COVID, and what it really takes to build something meaningful here. From real estate to vlogging…

Mike Joseph And Stefan Prior Podcasts

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The Cayman Life

Mike Joseph and Stefan Prior

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S1 E9: George Loutus on Cayman’s Real Estate Shifts and Starting Fresh 30:22

1
S2 E1: Jude Holland on Career Pivots, Culture, and Doing Real Estate Differently 37:57

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S2 E2: Acts of Random Kindness, A Journey of Love with Tara Neilsen 47:19

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S2 E3: From Fund Administration to AI Ventures with Tim Rossiter 46:14

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S2 E4: Julia Dougall on Navigating the Music Industry from Cayman 33:44

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S1 E6: Chris Kirkconnell on Family, Retail, and the Future of Georgetown 27:04

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S1 E7: Family Dynamics in Wealth Preservation with Bernadette Carey 20:25

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S1 E8: Residency by Investment: Opportunities and Challenges with Cline Glidden 49:59

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S1 E3: Georgina Lockstab on Money, Mindset, and Planning for the Future 54:07

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S1 E4: Ian Jamison on Inward Investment, Community, and Life in Cayman 32:37

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S1 E5: Navigating Family Life and Education in Cayman with Sophie Taylor 32:19

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S1 E1: James Whitaker on Cayman’s Path to Sustainability 50:39

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S1 E2: From Wall Street to West Bay – Tim Fury’s Story 57:04