Month: October 2026
Building a Legacy: Family, Leadership & Life Beyond the Phillies with Rubén Amaro Jr. (Ep. 29)

Building a Legacy: Family, Leadership & Life Beyond the Phillies with Rubén Amaro Jr. (Ep. 29)

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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: 

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Connect with Rubén Amaro Jr.: 

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.

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Special Needs Trust Planning for Families with Sheila Gibson (Ep. 28)

Special Needs Trust Planning for Families with Sheila Gibson (Ep. 28)

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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: 

Connect with Kate Duffy: 

Connect with Jamie Hopkins: 

Connect with Sheila Gibson: 

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. 

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