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Entrepreneurial Legacies: Daily Summaries Delivered
by Clearwater Capital Partners
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
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- 1 weeks ago1h 18m
Health Management: Harper Health Concierge Care with Dr. Will Harper
In this episode of Entrepreneurial Legacies, John Sleeting sits down with Dr. Will Harper, founder of Harper Health, to explore how concierge medicine is reshaping the patient experience through personalized care, lasting relationships, and a more holistic view of health. Drawing on his experience at the University of Chicago and his journey to founding Harper Health, Dr. Harper shares what inspired him to challenge the traditional healthcare model and create a practice centered on giving patients the time, attention, and individualized care they deserve. Together, John and Dr. Harper discuss the importance of looking beyond immediate symptoms to consider the whole person, including the mind, body, and spirit. The conversation also explores the realities of building a medical practice, navigating an evolving healthcare landscape, and incorporating technology without losing the human connection at the heart of medicine. Throughout the episode, Dr. Harper reflects on the value of intentional decision-making, consistency, and discipline in pursuing long-term goals, drawing meaningful parallels between the principles of personalized healthcare and wealth stewardship. 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, tax, or medical 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. Dr. Harper is not a client of Clearwater Capital Partners. No compensation was provided to Dr. Harper in exchange for his participation or comments. Employees of Clearwater Capital Partners are Dr. Harper's patients. Dr. Harper 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.
- Oct 1, 20261h 14m
Health Management: Proactive Longevity Precision with Dr. Anand Patel
In this episode of Entrepreneurial Legacies, John Sleeting sits down with Dr. Anand Patel, Founder, CEO, and practicing lead physician at LV8 Health, to explore a different way of thinking about health, longevity, and the role we play in shaping our future. Kicking off a new mini-series on health management, John and Dr. Patel explore the parallels between managing your health and managing your wealth: both require intentionality, planning, personalization, and a willingness to invest today in the life you hope to live tomorrow. Dr. Patel shares his journey from practicing within a large healthcare system to building a more personalized model of care rooted in prevention, precision, and long-term thinking. The conversation also explores his perspective on Medicine 3.0 and the shift from reactive healthcare toward a more proactive understanding of the individual. In this episode, we discuss: • Rethinking healthcare: Why Dr. Patel believes the traditional healthcare model can lose sight of the individual, and what opportunities exist to create a more personalized doctor-patient relationship. • Medicine 3.0: The evolution from traditional, evidence-based medicine toward a model centered on prevention, hyper-personalization, precision, and understanding the individual patient. • Health as an investment: How thinking about health as a long-term investment can change the way we allocate our time, resources, and attention, much like we approach financial capital. • The "perfect Tuesday" at 80: Why Dr. Patel starts with a simple but powerful question about what a person wants their life to look like decades from now, and how today's habits can help make that future possible. • Agency in your health: Why patients should not simply accept the healthcare system as it is, and how individuals can take a more active role in understanding their options, asking better questions, and making informed decisions. • The role of AI: How artificial intelligence can serve as a tool and thought partner for patients and families as they seek to understand their health better, while recognizing the importance of professional wisdom and judgment. • Wisdom, experience, and mentorship: Why knowledge alone is not enough, how wisdom develops through experience, and why surrounding yourself with people who have walked the path before you can accelerate your own learning. At its heart, this conversation looks beyond the immediate moment and asks a larger question:
- Sep 1, 20261h 21m
Game Changers: Changing The Game from Business to Nonprofit Leadership with John Aiello
In this episode of Entrepreneurial Legacies, we sit down with John Aiello for a thoughtful conversation on entrepreneurship, faith, purpose, and the lasting impact we create through the lives of others. John shares the story of founding and growing a pioneering cloud software company, from navigating financial uncertainty to recognizing a real market need and building a business around it. His journey offers a candid look at the perseverance, conviction, and adaptability required to build something meaningful when the path forward is anything but certain. But this conversation goes beyond the traditional measures of entrepreneurial success. John reflects on his transition from building a business to pursuing ministry, and how that experience reshaped his understanding of purpose, influence, and what it means to build a life of significance. At the heart of the conversation is a powerful perspective on legacy: what we build matters, but so does who we build into. This conversation explores the intersection of business, faith, philanthropy, and personal growth, and the ways investing in people can create an impact that extends far beyond a company or career. The episode invites entrepreneurs to consider a deeper question: What are you building, who are you investing in, and what will remain because you were here? In this episode, we discuss: • Building and growing a pioneering cloud software company • Navigating financial uncertainty and the realities of entrepreneurship • Recognizing market needs and building with purpose • The intersection of faith, business, and personal growth • Investing in people as a meaningful measure of legacy • The role of philanthropy in creating lasting impact • Redefining success beyond business and financial achievement Take a moment to consider not only what you are building, but who you are building into and the legacy you want to 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 opinions and do not reflect the opinion of Clearwater Capital Partners. Mr. Aiello is not a client of Clearwater Capital Partners. No compensation was provided to Mr. Aiello in exchange for his participation or comments. Mr. Aiello has no other material conflict of interest relating to his relationship with Clearwater Capital Partners. Clearwater Capital Partners is not affiliated with www.openthebible.org<span style
- Aug 1, 20261h 19m
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.
- Jul 1, 20261h 19m
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.
- Jun 1, 20261h 18m
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, 20261h 30m
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.
- Apr 1, 20261h 25m
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.
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About Entrepreneurial Legacies
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
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