Newsworthy Topics

Thinking Differently with Philadelphia Union’s Jay Sugarman (Ep. 16)

Jamie Hopkins, Esq., LLM, CFP®, ChFC®, CLU®, RICP®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

Kate Duffy, FBS®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

April 27, 2026

2 min read

Winning by Thinking Differently

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What does it take to think differently—and still win? In this episode, Jamie Hopkins and Kate Duffy sit down with Jay Sugarman, Principal Owner of the Philadelphia Union and Chairman and CEO of Safehold to explore how unconventional thinking has defined his career. Jay reflects on how frequent change early in life built resilience, sharpened pattern recognition, and shaped a disciplined, principles‑driven approach to decision‑making.

From real estate to professional sports, Jay shares how challenging consensus thinking can reveal opportunity. He explains how applying corporate finance logic to outdated real estate structures unlocked value, and how a development‑first, long‑term mindset transformed a professional soccer organization—proving that thoughtful innovation often outperforms convention.

Highlights from the conversation include:

How early life transitions fostered adaptability and strategic pattern recognition
Why contrarian thinking can surface opportunity during periods of market or industry change
How rethinking legacy structures in real estate led to meaningful innovation
Why investing in talent development and systems can drive sustainable success

Jamie Hopkins, Esq., LLM, CFP®, ChFC®, CLU®, RICP®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

Jamie Hopkins oversees the private wealth management group’s financial advice strategies and growth initiatives, along with leading the institutional and personal trust businesses. He joined the company in 2023.

Kate Duffy, FBS®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

Kate Duffy collaborates with clients to provide wealth management strategies, financial planning, and investment advice. She joined the company in 2024.

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