Entrepreneurial Legacies

Hosted by Clearwater Capital Partners

Business EntrepreneurshipInterviews guests

Website RSS feed

Episodes

Latest episode

Aug 2026

Language

About the show

Welcome to Entrepreneurial Legacies, brought to you by Clearwater Capital Partners, a multi-family office and wealth management firm dedicated to inspiring and empowering clients to live with confidence, joy, and a spirit of abundance. Dive into the principles of financial stewardship, multigenerational wealth planning, and the evolving landscape of family office advisory, offering practical insight for investors, business owners, and families seeking long-term financial clarity. The Entrepreneurial Legacies series, hosted by John Sleeting, Managing Partner of Family Office Services at Clearwater Capital Partners, takes listeners behind the scenes of entrepreneurial families and business founders. Each episode explores real-world journeys that include launching new ventures, leadership challenges, scaling for growth, liquidity events, estate strategy, investment decision-making, philanthropy, and family governance. Through candid conversations and firsthand perspectives, listeners gain valuable insight into wealth management, legacy planning, and the pivotal decisions that shape successful families and individuals as they consider what comes next in their journeys.

Listen to episodes

47 recent

August 1, 20261 hr 19 min

Game Changers: Golftini's Brand Building Purpose with Susan Hess

In this episode of Entrepreneurial Legacies , we sit down with Susan Hess, Founder and CEO of Golftini, to explore what it takes to build a business rooted in resilience, purpose, and authenticity. What began as a simple solution to a problem on the golf course evolved into a nationally recognized apparel brand. Susan shares how she navigated launching a company during the 2008 financial crisis, the lessons she learned through adversity, and why staying true to her values has always been at the center of her leadership. The conversation extends beyond entrepreneurship into the personal principles that shape lasting success. From balancing family and business to embracing philanthropy and leading with empathy, Susan reflects on the decisions that have defined both her career and the legacy she hopes to leave behind. This episode explores an important question: How do entrepreneurs build something that endures while remaining grounded in the values that matter most? In this episode, you'll learn: • How identifying an unmet need can spark an entrepreneurial opportunity • Why resilience is often the defining characteristic of long-term success • How family, empathy, and authenticity shape stronger leadership • The role philanthropy plays in creating a legacy beyond business Whether you're building a business, leading a team, or defining your own legacy, this conversation offers practical insights and a thoughtful perspective on creating meaningful impact that extends far beyond success alone. 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 opinions and do not reflect the opinion of Clearwater Capital Partners. Ms. Hess is not a client of Clearwater Capital Partners. No compensation was provided to Ms. Hess in exchange for her participation or comments. Ms. Hess has no other material conflict of interest relating to her relationship with Clearwater Capital Partners.

July 1, 20261 hr 19 min

Game Changers: Golf, Motorsports, and Life Lessons with Joie Chitwood

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 professional golf, Joie reflects on the experiences that have shaped his leadership philosophy, the responsibility of carrying on a well-known family legacy while forging his own path, and why some of life's greatest opportunities begin with setbacks. Together, we explore the mindset required to lead through uncertainty, embrace change, and continue moving forward with purpose. Joie shares how challenges have become catalysts for growth and offers practical insights on leadership, perseverance, and creating lasting impact both personally and professionally. Whether you're building a business, leading a team, or navigating your own next chapter, this conversation serves as a reminder that legacy is not defined by perfection. It is built through resilience, character, and the willingness to keep learning. In this episode, we discuss: Why failure is often the foundation for future success Leading with resilience through uncertainty and change Honoring a family legacy while creating your own Leadership lessons from the worlds of motorsports and professional golf The parallels between competition, business, and long-term success Join us for a conversation that explores how our greatest challenges often become the experiences that define the legacy we leave behind. 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. Mr. Chitwood is not a client of Clearwater Capital Partners. No compensation was provided to Mr. Chitwood in exchange for his participation or comments. Mr. Chitwood has no other material conflict of interest relating to his relationship with Clearwater Capital Partners. Investment Advice offered through Clearwater Capital Partners, a Registered Investment Advisor.

June 1, 20261 hr 18 min

Philanthropic Legacies: Critical Planning & Intentionality with Dr. Kent Rhodes

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 families create impact that extends well beyond financial success. Together, we explore how aligning business decisions with family values can strengthen relationships, foster continuity, and shape future generations. Rather than focusing solely on growth or accumulation, this conversation encourages listeners to think more deeply about stewardship, purpose, and the long-term influence of the choices families make together. From navigating family dynamics to creating meaningful charitable initiatives, the episode offers a practical perspective for families seeking to lead with clarity and intention. This discussion asks an important question: how can families build enduring success while staying grounded in the values that matter most? In this episode, we discuss: The connection between family dynamics and business leadership Governance structures that support continuity across generations The role of philanthropy in strengthening family purpose and connection Building a legacy rooted in stewardship, intentionality, and impact Take a moment to reflect on the values shaping the legacy you hope to leave for generations to come. 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. Dr. Kent Rhodes is not a client of Clearwater Capital Partners. No compensation was provided to Dr. Rhodes in exchange for his participation or comments. Dr. Rhodes has no other material conflict of interest relating to his relationship with Clearwater Capital Partners. All opinions expressed by participants are solely their own opinions and do not reflect the opinion of Clearwater Capital Partners. Clearwater Capital Partners is not affiliated with The Family Business Consulting Group. Investment Advice offered through Clearwater Capital Partners, a Registered Investment Advisor.

May 1, 2026Episode 431 hr 30 min

Philanthropic Legacies: Integrating Your Life's Story with Caleb Breakey

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 embracing honest reflection, this conversation highlights how both defining moments and everyday experiences shape the impact we make. Together, they unpack the connection between storytelling and entrepreneurship, and how a clear understanding of your story influences leadership, decision-making, and generosity. Rather than striving for a polished version of success, Caleb makes the case for authenticity, growth, and living with intention. This episode is both an invitation and a challenge: what changes when you fully embrace your story and use it to serve others? In this episode: The role of storytelling in personal and professional growth Why failure is a critical part of a meaningful narrative How your story shapes leadership, legacy, and impact The connection between storytelling, generosity, and purpose 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. Caleb Breakey is not a client of Clearwater Capital Partners. No compensation was provided to Mr. Breakey in exchange for his participation or comments. Mr. Breakey has no other material conflict of interest relating to his 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.

April 1, 20261 hr 25 min

Philanthropic Legacies: The Art of Giving Wisely with Jeff Wallace

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 recognizing that even the smallest moments of generosity can create impact far beyond what we can see, this conversation explores how faith and intentional living influence the way we steward our time, talent, and treasure. Rather than chasing immediate returns or recognition, Jeff reminds us that lasting impact often begins with small, consistent choices to serve others well. Whether it is supporting a colleague, extending patience in a frustrating moment, or using our resources to bless others, those everyday decisions compound in powerful ways. This episode is both a reflection and a challenge: how might one small act of generosity today create a ripple effect tomorrow? In this episode, we discuss: The power of the 1% improvement mindset Why service is foundational to meaningful leadership How generosity can shape a lasting legacy Living intentionally with your time, talent, and treasure Take a moment to reflect on how one small act of kindness or generosity today could impact someone else's story. 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 Kevin Rochford are employees of Clearwater Capital Partners. Jeff Wallace is not a client of Clearwater Capital Partners. No compensation was provided to Mr. Wallace in exchange for his participation or comments. Mr. Wallace has no other material conflict of interest relating to his 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. Clearwater Capital Partners is not affiliated with the National Christian Foundation.

March 1, 20261 hr 18 min

Philanthropic Legacies: The Ascending Generation with Kate Gardner

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 explore the opportunities and pitfalls of inherited wealth, how families can approach legacy with intention, and why open communication is more important than most realize. They also discuss the role of faith, the impact of philanthropy, and how giving helped Kate find purpose and clarity in her own life. This conversation offers practical insights for families navigating generational wealth, while also providing a thoughtful reflection on what it truly means to steward resources responsibly. If you're interested in legacy planning, wealth stewardship, or the human side of financial conversations, this episode offers real-world wisdom and meaningful perspective. Title Referenced in this Episode: https://medium.com/@generosity_ny/biblical-framework-for-tithing-241ae887edfb 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. Kate Gardner is not a client of Clearwater Capital Partners. No compensation was provided to Ms. Gardner in exchange for her participation or comments. Ms. Gardner 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.

February 1, 2026Episode 21 hr 13 min

Choosing Clearwater Capital by Kevin Rochford

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 long-term alignment are central to effective wealth management today. Kevin also shares what led him to Clearwater Capital Partners, citing the firm's collaborative culture, nimble structure, and unwavering commitment to putting clients first. Throughout the conversation, the focus extends beyond performance to the role wealth plays in leadership, values, and legacy. This episode underscores the importance of thoughtful planning, clear perspective, and building strategies designed to support what matters most to families over time. 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 Kevin Rochford are employees of Clearwater Capital Partners. All opinions expressed by participants are solely their own opinion and do not reflect the opinion of Clearwater Capital Partners. John Sleeting sits on the Advisory Board for the Family Wealth Alliance (FWA). Clearwater Capital Partners is a member of the Family Wealth Alliance (FWA).

January 1, 2026Episode 11 hr 19 min

Private Market Participation & Portfolio Construction with Tyler Beachler

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 space often demands a more personalized approach. Tyler offers an inside look at what it truly takes to evaluate private market opportunities, from identifying top-tier managers to understanding the operational groundwork behind every investment. He walks listeners through Clearwater's private markets platform and the rigorous due diligence process that informs each decision. The conversation also touches on the growing movement to democratize private markets, the new risks that come with expanded access, and how strategies like secondary investments and co-investments are reshaping capital allocation. Throughout the episode, John and Tyler reinforce one core message. A thoughtful, tailored investment strategy built around long-term client goals matters far more than chasing the latest market trend. Disclosures: 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. A Qualified Purchaser is a specific designation under U.S. securities laws, defined in Section 2(a)(51) of the Investment Company Act of 1940 and is more stringent than that of an accredited investor. This status is intended to identify individuals or entities with sufficient wealth or investment sophistication to participate in certain high-risk or complex investment opportunities, such as private investments and hedge funds that rely on exemptions from registration under the Investment Company Act and otherwise unavailable to the general public. Qualified Purchasers are individuals or family-owned companies having $5 million or more in investments, such as stocks, bonds, and other securities, not including a primary residence. The Global Family Office Report can be found through UBS. Clearwater Capital Partners is not affiliated with UBS. John Sleeting and Tyler Beachler are employees of Clearwater Capital Partners. All opinions expressed by participants are solely their own opinion and do not reflect the opinion of Clearwater Capital Partners. John Sleeting sits on the Advisory Board for the Family Wealth Alliance (FWA). Clearwater Capital Partners is a member of the Family Wealth Alliance (FWA).

December 1, 2025Episode 121 hr 17 min

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

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 dialogue, and shared values can help prevent conflicts and strengthen relationships. They also explore how families can redefine success beyond mere financial wealth, focusing instead on purpose, relationships, and lasting impact. This episode provides a profound and honest examination of the human aspects of wealth, addressing what it takes to keep families grounded, united, and thriving 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. Gary Shunk is not a client of Clearwater Capital Partners. No compensation was provided to Mr. Shunk in exchange for his participation or comments. Mr. Shunk has no other material conflict of interest relating to his 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.

November 1, 2025Episode 111 hr 13 min

Family Governance: The Williams Group Bridging Generations with Amy Castoro

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.