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 He explains how applying corporate finance logic to outdated real estate structures unlocked value, and how a development‑first, long‑term mindset transformed a professional soccer organization—proving that thoughtful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

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 Jay Sugarman:

• Website: Philadelphia Union
• Website: Safehold

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.

Strong businesses are not just built on strategy; they are shaped by relationships, trust, and shared experiences.

What happens when leadership, family, and growth all intersect? And how do you balance speed, alignment, and long-term vision without losing what matters most?

In this episode, Jamie Hopkins and Kate Duffy interview Eric Faggioli, President of Delaware Valley Paving, about scaling a family-run business while maintaining strong personal relationships. He shares how alignment and trust drive decision-making, why early exposure to hard work shapes leadership, and how he navigated stepping into leadership after personal loss.

The conversation also explores building teams from within, improving service to stand out, and expanding operations nationwide through partnerships and systems.

Key takeaways:

• How prioritizing alignment and trust over top talent can reduce friction and improve long-term execution
• Why maintaining friendships within family businesses helps prevent conflict and strengthens collaboration
• How early exposure to physically demanding work builds resilience and long-term perspective
• The role of service differentiation and small improvements in creating meaningful client experiences
• How scaling nationally requires strong subcontractor networks, systems, and consistent execution

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 Eric Faggioli:

• LinkedIn: Eric Faggioli
• Website: Delaware Valley Companies
• Instagram: @delawarevalleypaving
• YouTube: Delaware Valley Paving

About our Guest:

Eric Faggioli is the CEO of Delaware Valley Companies, the parent organization of Delaware Valley Paving and its expanding family of businesses. This includes the company’s core Paving division, its National Construction operations, its Excavation business, and its growing real estate Development company. As a leader of a third-generation organization headquartered in Philadelphia, PA, Eric brings a unique blend of hands-on experience and long-term vision to every facet of the enterprise.

Having grown up in the paving business, Eric developed an early appreciation for strong relationships, dependable service, and uncompromising craftsmanship. From childhood through adulthood, he worked in every area of the company, gaining practical insight that now shapes his leadership approach. Over the past decade, Eric has played a pivotal role in expanding Delaware Valley Companies’ capabilities and strengthening its reputation nationwide. Under his guidance, the organization has opened new locations, broadened its service offerings, and advanced a comprehensive 10-year strategic plan designed to elevate performance, scalability, and client experience across all business units.

What drives Eric most is developing exceptional leaders and building systems and processes that will stand the test of time. With that mindset, Eric leads Delaware Valley Companies and its expanding divisions with a focus on sustainable growth, strong leadership development, and long-term success.

**Note: The guest featured in this episode is a current client of our organization and did not receive any compensation for their participation in the program.**

Giving is often seen as something reserved for the wealthy, but the truth is far more personal and accessible.

How do you decide where your money, time, and energy can truly make a difference? And how can you feel confident that your contributions are creating real impact?

In this episode, Jamie Hopkins and Kate Duffy are joined by Elizabeth Wagner, Senior Vice President and Director of Endowments, Foundations, and Charitable Giving at Bryn Mawr Trust, to explore how individuals at any income level can approach philanthropy with intention. They break down how to evaluate charities, align giving with personal values, and use practical strategies like QCDs and tracking donations.

The conversation also highlights the role of volunteering, family influence, and simple habits that help donors stay organized and effective.

Key takeaways:

• How donors can assess if a charity is effective by reviewing leadership, impact reporting, and firsthand experience

• Why volunteering provides insight into how organizations operate and how funds are actually used

• A simple notes app strategy to track donations, receipts, and giving habits throughout the year

• How QCDs and tax strategies can help increase charitable giving without increasing out-of-pocket costs

• Why aligning giving with personal values and early family influences shapes long term philanthropic habits

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 Elizabeth Wagner:

• LinkedIn: Elizabeth Wagner

About our Guest:

As a connector and advisor to nonprofits and philanthropists, Elizabeth Wagner helps organizations build the long-term financial sustainability their missions deserve while guiding donors toward meaningful impact. She leads the endowment, foundation, and charitable practice at Bryn Mawr Trust, supporting organizations with solutions that strengthen their work today and prepare them for future growth and challenges.

Elizabeth believes every organization should clearly define the role of each asset and use it intentionally to support its mission. She works closely with boards and leadership teams, sharing best practices around investment policy statements, institutional asset allocation, planned giving, and more. She is especially passionate about donor-advised funds, complex gifts, multigenerational giving, and engaging the next generation of philanthropic leaders early.