Family Office

In this episode of “Clear Conversations: Entrepreneurial Legacies,” John Sleeting sits down with Amy Castoro, President of The Williams Group, to explore what it truly takes to prepare families for a successful wealth transition.

Amy shares insights from her years of experience working with ultra-high-net-worth families, highlighting the emotional and relational aspects of legacy planning. Together, she and John delve into the deeper dimensions of family wealth, trust, communication, and personal growth, illustrating how these elements contribute to a family’s long-term success beyond financial strategy alone. The conversation introduces the concept of the “wisdom economy,” where wisdom, not just knowledge, becomes essential for guiding families in an era increasingly driven by AI and rapid change. Amy outlines The Williams Group’s five-step process for navigating wealth transitions, stressing that lasting success begins with strong relationships and shared purpose. Through compelling stories and practical advice, this episode provides families and advisors with a roadmap for fostering unity, enhancing understanding, and passing on more than just money; it emphasizes the importance of preserving meaning, values, and connection across generations. This podcast is for informational purposes only and should not be regarded as personalized investment advice or relied upon for investment decisions and is not intended to provide legal or tax advice. John Sleeting is an employee of Clearwater Capital Partners. Amy Castoro is not a client of Clearwater Capital Partners. No compensation was provided to Mrs. Castoro in exchange for her participation or comments. Mrs. Castoro has no other material conflict of interest relating to her relationship with Clearwater Capital Partners. All opinions expressed by participants are solely their own opinion and do not reflect the opinion of Clearwater Capital Partners. Mark Phillips, Roy Williams, Kirby Rosplock, and Tom Livergood are not clients of Clearwater Capital Partners. The Williams Group, 11 Tribes Ventures, Bridging Generations, written by Roy Williams and Amy Castoro, and the Next Gen Leaders Institute are not affiliated with Clearwater Capital Partners. Clearwater Capital Partners is a member firm of the Family Wealth Alliance. John Sleeting is on the Advisory Board for the Family Wealth Alliance.

In this episode of Entrepreneurial Legacies, host John Sleeting sits down with Dr. Kirby Rosplock, PhD, Founder & CEO of Tamarind Partners and Tamarind Learning, to unpack the complexities of managing wealth across generations.

Born into a complex and enterprising fourth-generation family, heirs to the legacy of Babcock Lumber Company, Kirby brings lived experience as an inheritor, board member, fiduciary, and operator. Her family’s historic stewardship includes preserving over 73,000 acres of Babcock Ranch, the largest single land preservation agreement in Florida’s history. That background fuels her mission today: helping families not just preserve their wealth but steward it with purpose. A recognized innovator, educator, and trusted advisor, Kirby founded Tamarind Partners in 2014, a consultancy that has been honored as Best Family Office Management Consultancy and Best Family Wealth Counseling by the Family Wealth Report. In 2020, she launched Tamarind Learning, an award-winning online platform designed to close one of the most overlooked gaps in family wealth: education. Tamarind Learning equips beneficiaries, future stewards, and advisors with practical, hands-on knowledge across both the technical and human dimensions of legacy management, empowering families to understand, engage with, and help preserve their wealth across generations. Throughout her career, including more than a decade as head of R&D at a prominent multi-family office, Kirby has become a globally sought-after speaker, author, and thought leader in the family wealth and governance space. Her insights have been featured in Tharawat Magazine, Family Business Magazine, and across leading industry platforms. She also serves as Dean of Family Office at the Purposeful Planning Institute and on faculty at the Family Office Real Estate Institute. In this conversation, Kirby shares practical tools and hard-earned wisdom: from family councils and constitutions to philanthropy and tailored education. She emphasizes the importance of intentionality, adaptability, and participation in strengthening not just assets, but relationships. It’s a deep dive into what it means to steward wealth with purpose and how modern families can shape legacies that endure. This podcast is for informational purposes only and should not be regarded as personalized investment advice or relied upon for investment decisions and is not intended to provide legal or tax advice. John Sleeting is an employee of Clearwater Capital Partners. All opinions expressed by participants are solely their own opinion and do not reflect the opinion of Clearwater Capital Partners. Dr. Rosplock is not a client of Clearwater Capital Partners. No compensation was provided to Dr. Rosplock in exchange for her participation or comments. Dr. Rosplock has no other material conflict of interest relating to her relationship with Clearwater Capital Partners.

In this episode of Entrepreneurial Legacies, John Sleeting sits down with Hunter Sims, Associate Director at the Cambridge Centre for Alternative Finance (CCAF) at the University of Cambridge Judge Business School.

Hunter works at the forefront of financial innovation, focusing on how digital assets, policy, and regulation intersect to shape the future of global finance. At CCAF, he collaborates with policymakers, industry leaders, and academics to advance research that informs evidence-based regulation and drives the sustainable development of new financial systems. Together, John and Hunter explore the rapid evolution of the financial industry in the era of blockchain and decentralized finance. From the fundamentals of the digital-asset ecosystem to the roles of Bitcoin, Ethereum, tokenization, and stablecoins, their conversation unpacks how technology is transforming money and markets. They also examine the challenges of regulation, the uncertainty around (or surrounding) global adoption, and what these shifts could mean for businesses navigating this fast-changing space. Packed with insights on FinTech, open banking, and DeFi, this episode highlights how innovation, research, and policy are converging to create new opportunities in the global financial system. Episode Overview:
This episode discusses the fundamentals of digital assets, the rise of cryptocurrency and tokenization, the impact of decentralized finance (DeFi), regulatory challenges, and the role of institutions like the Cambridge Centre for Alternative Finance in shaping the future of money. This podcast is for informational purposes only and should not be regarded as personalized investment advice or relied upon for investment decisions and is not intended to provide legal or tax advice. John Sleeting and Hunter Sims are employees of Clearwater Capital Partners. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Clearwater Capital Partners.