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.

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