Tag: community impact
Thinking Differently with Philadelphia Union’s Jay Sugarman (Ep. 16)

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

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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 He explains how applying corporate finance logic to outdated real estate structures unlocked value, and how a development‑first, long‑term mindset transformed a professional soccer organization—proving that thoughtful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.

Key takeaways include:

  • How early life transitions fostered adaptability and strategic pattern recognition
  • Why contrarian thinking can surface opportunities 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

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About our Guest: 

Jay Sugarman is Chairman and Majority Owner of the Philadelphia Union and Union Sports & Entertainment.

Mr. Sugarman is also Chairman and Chief Executive Officer of iStar (NYSE:STAR), a leading commercial real estate company in the United States. iStar’s current $6 billion portfolio of real estate interests is located in most major markets throughout the United States and includes interests in office, industrial, multifamily, hotel, land and entertainment properties. Mr. Sugarman is also Founder, Chairman and CEO of Safehold (NYSE: SAFE), one of the fastest-growing REITs since its IPO in 2017. Safehold is revolutionizing commercial real estate ownership by reinventing and modernizing the ground lease industry, with an enterprise value approaching $5 billion.

Mr. Sugarman graduated summa cum laude from Princeton University, where he was nominated for valedictorian and received the Paul Volcker Award in Economics. He received his M.B.A. with high distinction from Harvard Business School, graduating as a Baker Scholar and recipient of the school’s academic prizes for both finance and marketing.

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Leading With Values and Vision with Rodger Levenson (Ep. 3)

Leading With Values and Vision with Rodger Levenson (Ep. 3)

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Leadership transitions often bring uncertainty, but with the right mindset, they can create opportunity and growth.

How do you step into bigger roles with confidence? How do mentorship, values, and community shape the journey of a leader?

In this episode of The Planning Perspectives Podcast, hosts Jamie Hopkins and Kate Duffy welcome Rodger Levenson, Chairman, President, and CEO of WSFS Financial Corporation. Rodger shares his career journey, the importance of mentorship, the challenges of saying no, and why community connection is central to WSFS’s culture.

Key takeaways:

  • How Rodger progressed from credit analyst to CEO, and the leadership lessons learned along the way
  • The importance of mentors and building meaningful peer relationships
  • Why learning to say “no” is essential for effective leadership
  • How business owners display resilience and adaptability in changing environments
  • Why connecting employees’ work to a greater purpose drives lasting impact in the community
  • And more!

Connect with Bryn Mawr Trust: 

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About Our Guest: 

Rodger Levenson is Chairman, President, and Chief Executive Officer of WSFS Financial Corporation and its primary subsidiary, WSFS Bank.

Rodger has been a member of the WSFS Executive Management team since joining the Company in 2006. He has held several leadership roles at WSFS, including Executive Vice President (EVP) and Chief Operating Officer from July 2017 to December 2018, EVP and Chief Corporate Development Officer from June 2016 to July 2017, interim EVP and Chief Financial Officer from April 2015 to June 2016, and EVP and Chief Commercial Banking Officer from November 2006 to April 2015.

He began his banking career in 1986 in Philadelphia at CoreStates Financial (now part of Wells Fargo), where he led several business units over 17 years.

An active member of the Greater Philadelphia and Delaware communities, Rodger lends his experience and expertise to several local not-for-profits while continuing to champion economic growth throughout the region. His community and civic service includes memberships on the U.S. Federal Reserve Board’s Federal Advisory Council (FAC), Delaware Prosperity Partnership Board of Directors, as well as the Board of Directors, Executive Committee, and CEO Council for Growth of The Chamber of Commerce for Greater Philadelphia. He also serves as a member of the Delaware Business Roundtable, Children’s Hospital of Philadelphia (CHOP) Corporate Council, and on the Executive Committee of the Satell Institute for Corporate Social Responsibility. Rodger previously served as Chairman of the Delaware Bankers Association as well as the United Way of Delaware Board of Directors.

In 2021, Rodger was the recipient of the American Jewish Committee (AJC) Philadelphia and Southern New Jersey’s Community Leadership Award. In 2022, Rodger was named Drexel University Business Leader of the Year.

A native of Broomall, Pa., Rodger earned a Master of Business Administration from Drexel University and a Bachelor of Business Administration in Finance from Temple University. He reinforced his leadership experiences with certifications from The Wharton School at the University of Pennsylvania, the Center for Creative Leadership, and Harvard Business School.

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