What does it take to navigate success, setbacks, and career transitions at the highest level? Jamie Hopkins and Kate Duffy sit down with former Phillies General Manager Rubén Amaro Jr. for a conversation about family, leadership, resilience, and the lessons that shape a lasting legacy.

Amaro reflects on his family’s remarkable baseball journey, from his father’s path from Cuba to the Major Leagues to the values of perseverance, education, and hard work that have guided multiple generations. He discusses the realities of leadership, learning to manage former teammates, developing new skills, and the mentors who helped shape his approach to leading people and organizations.

Along the way, Amaro offers insights on handling adversity, building confidence through setbacks, and creating opportunities for the next generation. Whether you’re leading a team, navigating a career change, or thinking about the legacy you want to leave behind, this episode delivers timeless lessons on growth, leadership, and purpose.

Rubén discusses:

• Why negotiation was the skill he most needed to develop, and how a boss who gave him autonomy helped him build it
• How he learned to stop measuring his worth by daily results and handle setbacks differently later in his career
• Why separating himself from teammates who were close friends was the hardest part of moving into the front office

Connect with Bryn Mawr Trust:

• 833-973-7633
• LinkedIn: Bryn Mawr Trust
• Website: Bryn Mawr Trust

Connect with Kate Duffy:

• LinkedIn: Kate Duffy

Connect with Jamie Hopkins:

• LinkedIn: Jamie Hopkins

Connect with Rubén Amaro Jr.:

• LinkedIn: Ruben Amaro, Jr.
• Website: Philadelphia Phillies

About our Guest:

Rubén Amaro Jr. is a former Major League Baseball player, Philadelphia Phillies general manager, and coach whose career has spanned the field and front office. A Philadelphia native and Stanford University graduate, he comes from a baseball family that includes his father, Rubén Amaro Sr., and grandfather, Santos Amaro. After his playing career, he became the Phillies’ assistant general manager and later led the club as general manager. His experiences have shaped his perspective on mentorship, leadership, changing careers, and the importance of education and family.

Planning for a loved one with special needs can raise difficult questions about benefits, inheritance, caregiving, and what happens when family members are no longer able to provide support.

In this episode, Kate Duffy speaks with Sheila Gibson, Senior Wealth Advisor at Bryn Mawr Trust, about special needs trusts and guardianships. They explain how a properly structured trust can preserve assets while supporting access to means-tested government benefits. Sheila also covers trustee responsibilities, letters of intent, inheritance planning, family involvement, documentation, and the importance of building a team that understands a beneficiary’s individual needs.

Sheila discusses:

• How special needs trusts can preserve assets while supporting access to means-tested government benefits
• Why leaving an inheritance directly to a beneficiary may unintentionally affect eligibility for public benefits
• How trustees can use trust assets for therapies, equipment, recreation, transportation, and other personal needs
• How families, wealth advisors, trustees, and trust and estate attorneys can coordinate long-term planning

Connect with Bryn Mawr Trust:

• 833-973-7633
• LinkedIn: Bryn Mawr Trust
• Website: Bryn Mawr Trust

Connect with Kate Duffy:

• LinkedIn: Kate Duffy

Connect with Jamie Hopkins:

• LinkedIn: Jamie Hopkins

Connect with Sheila Gibson:

• LinkedIn: Sheila Gibson
• SGibson@bmt.com

About our Guest:

Sheila Gibson is a Senior Wealth Advisor with Bryn Mawr Trust who specializes in special needs trusts and guardianships. She works with individuals and families to help them think through the financial and personal considerations involved in caring for a loved one with special needs, including trust planning, government benefits, trustee responsibilities, inheritance decisions, and long-term care needs. Sheila brings more than three decades of experience to these conversations and emphasizes the importance of coordination among families, caregivers, wealth advisors, and trust and estate attorneys.

Building a successful business is one thing. Building one that endures for decades is another. In this episode of the Planning Perspectives Podcast, Jamie Hopkins and Kate Duffy sit down with Chris Bailey, Founder and CEO of Bailey Brand Consulting, to discuss the principles that have helped his firm thrive since 1985. From leadership and mentorship to brand strategy, client trust, and navigating technological change, Chris shares lessons learned from nearly four decades of helping organizations create lasting value.

Key Takeaways:

• Why successful leaders balance short-term results with a long-term vision
• How mentorship, trusted advisors, and strong relationships can guide critical business decisions
• Why understanding your organization’s “why” is essential for sustained growth and culture
• How trust, authenticity, and customer experience contribute to brand value and loyalty
• What business leaders should consider as AI and technology reshape marketing and consumer expectations
• Why bigger isn’t always better—and how deep client relationships can create a competitive advantage
• How convenience and experience are influencing consumer behavior and business strategy today
• And more.

Whether you’re a business owner, investor, or leader looking to build something that lasts, this conversation offers practical insights on growth, brand value, and creating an organization that stands the test of time.

Connect with Bryn Mawr Trust:

• 833-973-7633
• LinkedIn: Bryn Mawr Trust
• Website: Bryn Mawr Trust

Connect with Kate Duffy:

• LinkedIn: Kate Duffy

Connect with Jamie Hopkins:

• LinkedIn: Jamie Hopkins

Connect with Chris Bailey:

• LinkedIn: Chris Bailey