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Beyond the Listing with Anna Fiascone and Natalie Ryan

Entrepreneurial Legacies

Release Date: 04/01/2025

Choosing Clearwater Capital by Kevin Rochford show art Choosing Clearwater Capital by Kevin Rochford

Entrepreneurial Legacies

In this episode of Entrepreneurial Legacies, John Sleeting sits down with Kevin Rochford for a thoughtful discussion on modern wealth management, legacy planning, and the evolving nature of client relationships. Drawing on decades of experience across global markets, family advisory work, and military service, Kevin shares how those experiences shaped a disciplined, values-driven approach to serving families.   John and Kevin explore the industry’s shift away from large institutional models toward more personalized, relationship-focused advice, and why trust, access, and...

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Private Market Participation & Portfolio Construction with Tyler Beachler show art Private Market Participation & Portfolio Construction with Tyler Beachler

Entrepreneurial Legacies

In this episode of Clear Conversations, John Sleeting sits down with Tyler Beachler, Deputy Chief Investment Strategist at Clearwater Capital, for a clear, practical introduction to the world of private markets. Building on earlier conversations about the entrepreneurial life cycle, they explore how business owners navigate the startup, growth, and maturity phases and the legal, tax, and financial planning considerations that matter most at each stage. John and Tyler also unpack how private market investing differs from the public markets many investors know well, and why success in this...

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Family Governance: The Psychology of Inter-Generational Wealth with Gary Shunk show art Family Governance: The Psychology of Inter-Generational Wealth with Gary Shunk

Entrepreneurial Legacies

In this episode of Entrepreneurial Legacies, John Sleeting sits down with Gary Shunk from Aligned Family, a prominent voice in wealth psychology. They discuss the intricate connections between money, family, and identity. The conversation delves into what occurs when families experience significant wealth transitions and highlights the importance of communication and connection in navigating these changes.   Gary shares insights gained from decades of experience working with families facing complex dynamics around inheritance and legacy. He and John emphasize that family meetings, open...

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Family Governance:  The Williams Group Bridging Generations with Amy Castoro show art Family Governance: The Williams Group Bridging Generations with Amy Castoro

Entrepreneurial Legacies

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...

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Family Governance: How Families Thrive Across Generations with Kirby Rosplock show art Family Governance: How Families Thrive Across Generations with Kirby Rosplock

Entrepreneurial Legacies

What does it take to build a family legacy that lasts? 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...

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Crypto Decoded: DeFi, Tokens & Beyond with Hunter Sims show art Crypto Decoded: DeFi, Tokens & Beyond with Hunter Sims

Entrepreneurial Legacies

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...

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M&A An Investment Banker's Perspective with Chris Geyer show art M&A An Investment Banker's Perspective with Chris Geyer

Entrepreneurial Legacies

In this episode of Entrepreneurial Legacies, John Sleeting sits down with Chris Geyer of Hennepin Partners to unpack the often-complex world of investment banking and mergers & acquisitions (M&A). Chris shares his professional journey, from his early days in the industry to his current role, and how those experiences have shaped his thoughtful, relationship-driven approach to deals today. He emphasizes the value of strategic planning, trust-building, and preparation in driving successful outcomes.   Together, Chris and John walk through the key steps of selling a business,...

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Clearwater's 5th Annual Charity Supercar Show show art Clearwater's 5th Annual Charity Supercar Show

Entrepreneurial Legacies

Join host John Sleeting for a special edition of Entrepreneurial Legacies, celebrating the people, stories, and purpose behind Clearwater’s 5th Annual Charity Supercar Show. In this episode, we spotlight the true power of community through conversations with passionate entrepreneurs, generous sponsors, and the inspiring beneficiaries this event supports. Driven by passion and inspired by giving, this episode offers a behind-the-scenes look at how one event drives real impact and why it matters. Episode Highlights: 0:0:38 - Greg Davis & John Chapman, Clearwater Capital Partners 0:15:38 -...

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M&A and Who We Become in the Process with Jeff Haanen show art M&A and Who We Become in the Process with Jeff Haanen

Entrepreneurial Legacies

In this episode of Clear Conversations, John Sleeting sits down with Jeff Haanen for an insightful discussion about the challenges business owners face during major transitions, particularly during mergers and acquisitions. Drawing from his personal and professional experiences, including his departure from the Denver Institute for Faith and Work, Jeff shares how this pivotal moment shaped his views on calling, identity, and leadership. Together, John and Jeff explore the often-overlooked emotional aspects of selling or transitioning a business. Jeff brings a unique perspective, influenced by...

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M&A From the Boardroom with Kip Pendleton show art M&A From the Boardroom with Kip Pendleton

Entrepreneurial Legacies

In this episode of Clear Conversations: Entrepreneurial Legacies, John Sleeting is joined by Kip Pendleton, an experienced leader in agriculture and mergers and acquisitions, for a candid discussion about what it takes to grow, optimize, and transition a business. Drawing on his recent work with Cox Family Holdings, Kip guides listeners through how strategic planning, thoughtful board structures, and the right external advisors can shape a company's future. During their conversation, John and Kip delve into the key ingredients that drive successful M&A work, particularly in the context of...

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In this episode of Entrepreneurial Legacies, John Sleeting sits down with Anna Fiascone and Natalie Ryan, two powerhouse luxury real estate agents serving Chicagoland’s western suburbs. With impressive professional backgrounds—Anna in law and Natalie in marketing and advertising—they joined forces in the real estate world to build a thriving, equal partnership.
Their conversation delves into the art of understanding diverse client needs, crafting tailored strategies, and navigating an ever-evolving real estate landscape amid national regulatory shifts. Anna and Natalie offer a wealth of insight into the nuances of luxury real estate, from the importance of adaptability to the strategic thinking required to stay ahead in a competitive market. 
Beyond business, this episode explores how professional success is shaped by personal passion, community engagement, and ethical business practices. Anna and Natalie share how their philanthropic efforts intertwine with their careers, strengthening both their professional impact and their legacy. As the discussion unfolds, listeners can gain valuable perspectives on market trends, the intricacies of high-end real estate transactions, and the lasting power of strong client-agent relationships. 
Disclosure:
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.
Investment Advice offered through Clearwater Capital Partners, a Registered Investment Advisor