Entrepreneurial Legacies

Every entrepreneurial journey is shaped by defining moments. Some come through success. Others emerge through adversity. In this episode of  Entrepreneurial Legacies , we welcome Joie Chitwood, Executive Director of the 2026 Presidents Cup, for a conversation about leadership, resilience, and the lessons learned from navigating both triumph and failure. Drawing on a career spanning motorsports and...

In this episode of Entrepreneurial Legacies, we sit down with Dr. Kent Rhodes for a thoughtful conversation on family enterprise, leadership, and the responsibility that comes with building a lasting legacy. Drawing from decades of experience advising entrepreneurial families, Dr. Rhodes shares insight into how intentional communication, strong governance, and values-driven philanthropy can help f...

In this episode of Entrepreneurial Legacies , John Sleeting sits down with Caleb Breakey of Renowned Publishing to explore the power of storytelling, purpose, and the legacy we are building every day. Caleb shares his path from journalism to helping others uncover and own their personal narratives, and why doing so is often the catalyst for meaningful transformation. From reframing failure to embr...

In this episode of Entrepreneurial Legacies, we sit down with Jeff Wallace, President of the National Christian Foundation in Chicago, for a thoughtful conversation about generosity, purpose, and the ripple effect of small acts done faithfully over time. Jeff shares how a mindset of service shapes our approach to leadership, wealth, and everyday life. From the idea of improving just 1% each day to...

In this episode of Entrepreneurial Legacies , John Sleeting sits down with Kate Gardner for an honest and deeply personal conversation about inheriting wealth at a young age and the journey that followed. Kate opens up about navigating sudden wealth syndrome and with it, the emotional challenges, questions of identity, and the responsibilities that come with stewardship. Together, John and Kate ex...

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 ser...

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...

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...

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. Togethe...

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...

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...

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 emph...

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, t...

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 vie...

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,...

In this episode of Clear Conversations: Entrepreneurial Legacies, John Sleeting interviews Garry Krum, founder and chairman of Agora Consulting. Together, they delve into the strategic aspects of building, growing, and eventually transitioning a business.  With years of hands-on experience in mergers and acquisitions, Garry provides a practical and insightful perspective on how to prepare a compan...

In this episode of Clear Conversations: Entrepreneurial Legacies, host John Sleeting is joined by Joe Kuchta , a seasoned leader in the advertising and marketing space, to share his path from corporate life to entrepreneurial success. Joe reflects on the pivotal moment he left a stable role at a large corporation to join a smaller agency—an early leap that would ultimately lead to long-term growth...

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...

In this episode of Clear Conversations' Entrepreneurial Legacy Series, host John Sleeting sits down with Tim Lynn—entrepreneur, philanthropist, and founder of NIR Roof Care Inc.—to explore his extraordinary journey. As NIR celebrates its 45th anniversary, Lynn reflects on his path from high school dropout to building a thriving business. He offers deep insights into the principles that have shaped...

In this episode of Clear Conversations: Entrepreneurial Legacies , John Sleeting welcomes back John Chapman, Founder, and CEO of Clearwater Capital Partners, to discuss the firm's evolution and future vision. Chapman shares insights on Clearwater Capital's strategic growth, operational advancements, and unwavering commitment to excellence in wealth management.   The conversation explores the firm'...

As we welcome 2025, this special episode of Clear Conversations - Entrepreneurial Legacies offers a moment to reflect and refocus. Host John Sleeting is joined by Katie Berganske-Frank, Chief Revenue Officer at Clearwater Capital Partners and one of the primary forces behind the podcast's initial alignment and execution. Together, John and Katie explore the entrepreneurial spirit behind extraordin...

In this episode of Entrepreneurial Legacies, John Sleeting sits down with Valerie Hogan J.D., CFP ®, a wealth advisor in the Family Office practice at Clearwater Capital Partners and a professional with a truly diverse background. Valerie's journey spans from aspiring science student to practicing attorney and philanthropic advocate, culminating in her impactful work in wealth management. Drawing...

Join host John Sleeting as he welcomes Melissa Whitaker, founder and CEO of Melissa Whitaker International and co-author of two books (Beat the Curve and Pushing to the Front), to explore her holistic approach to consulting, centered on leadership, culture, wellness, and sales training. In this episode, Melissa shares her entrepreneurial journey, guided by bold faith, resilience, and a strong dete...

Join John Sleeting as he welcomes Jae Haas, a CEO and entrepreneur whose diverse business experience offers fresh insights into leadership and family business dynamics. Jae shares his journey from the telecommunications and railroad sectors to becoming a non-family member CEO at Transnational Payments. He reflects on his decision to join the family business, and the lessons learned in building a c...

In this episode of Clear Conversations: Entrepreneurial Legacies, John Sleeting sits down with David Saporta to explore the intersection of entrepreneurship, family business dynamics, and personal faith. David, who climbed the executive ladder at Road Ranger from CFO to CEO, shares his journey of running a significant enterprise while being intricately involved with the owner family. With a financ...