Growth can look exciting from the outside—but behind every new location, partnership, or expansion are tough calls, people challenges, and the constant pressure to get it right.

So how do you scale a business without losing the culture that made it successful in the first place? And what does it really take to build a company people want to grow with?

In this episode, Jamie Hopkins and Kate Duffy sit down with Sydney Grims, Director of Business Development at Fearless Restaurants, to unpack what it takes to expand a hospitality brand while staying true to its roots. Sydney shares how her family’s restaurant background shaped her leadership approach, why building the right operational systems became essential, and how Fearless navigates hiring, real estate decisions, branding, and thoughtful growth.

They also dive into women in leadership, community-building through the Fearless Femmes initiative, and why sometimes the smartest growth strategy is slowing down.

Key takeaways:

• Why protecting culture—not just chasing growth—is the foundation of long-term success
• How stronger systems and faster response times unlocked new operational opportunities
• What to look for in new markets, from real estate strategy to local demand signals
• How intentional, measured growth helps avoid burnout and build a company people want to be part of

Resources:

• Website: Alpha Bravo Canine

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 Sydney Grims:

• LinkedIn: Sydney Grims
• Website: Fearless Restaurants
• Instagram: @fearlessrestaurants
• Instagram: @sydneygrims

About our Guest:

Sydney Grims serves as Director of Development for Fearless Restaurants, where she oversees the strategic growth and evolution of the company’s 14-property hospitality portfolio. Working directly with the Founder and CEO of the family-owned business, she helps advance both vision and execution across the organization.

Her role spans all divisions of Fearless, including capital projects, talent acquisition, sales and marketing, operations, and culinary. She leads cross-functional teams to bring new concepts to life, strengthen existing properties, and align each initiative with the company’s standards for hospitality, culture, and long-term value.

From guiding major capital investments and development initiatives to building teams and refining operational performance, Sydney focuses on sustainable growth rooted in people, place, and purpose. She works closely with leaders across the organization to translate strategy into action, balancing creativity with discipline and innovation with operational excellence.

At the core of her work is a commitment to preserving the integrity of a family business while thoughtfully expanding its impact. She takes pride in building environments where teams thrive, guests feel genuinely welcomed, and Fearless continues to set the standard for distinctive dining and hospitality experiences.

Sydney attended Cornell’s School of Hotel Administration to prepare for her role in the family business and has worked with several premier hospitality organizations, including Hillstone Restaurant Group.

Banking is personal—money touches nearly every major life moment, from big milestones to unexpected challenges. When clients have a trusted advisor, financial planning, problem-solving, and growth feel more human and more connected.

In this episode of the Planning Perspectives Podcast, Jamie Hopkins and Kate Duffy speak with Shari Kruzinski, Executive Vice President and Chief Consumer Banking Officer at WSFS Bank, about her 37-year journey from floating teller to senior leadership. Shari shares how local banking builds trust through strong branch relationships, associate development, youth financial education, small business support, and a deep commitment to community through volunteerism, grants, and homebuyer programs.

Key points:

• Shari’s service-driven career journey and lasting connection to local banking
• Why branch teams matter during life events, fraud concerns, and major financial decisions
• How youth banking programs help build strong financial habits early
• Community impact through small business support, volunteerism, grants, and housing initiatives

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 Shari Kruzinski:

• LinkedIn: Shari Kruzinski
• Website: WSFS Bank

About our Guest:

Shari Kruzinski is Executive Vice President and Chief Consumer Banking Officer at WSFS Bank. Her career spans nearly 40 years in the banking industry, serving for over 35 years with WSFS.

In her current position, Ms. Kruzinski leads the Consumer Banking division. Prior to her current role, Ms. Kruzinski was Executive Vice President and Chief Customer Officer, leading Customer Experience and enterprise-wide Customer initiatives. As a seasoned people manager and expert in talent development, she oversaw the Bank’s retail offices, contact center, sales strategy, and operations. Previously, she was Senior Vice President and Regional Manager of WSFS Bank’s Southeastern Pennsylvania market. She led the Bank’s operations and consumer and small business banking in Chester, Delaware, and Montgomery Counties. As a senior executive, she led the division through numerous acquisitions. Ms. Kruzinski played a key role in developing Customer acquisition and retention strategies; Associate hiring and retention, corporate strategy formulation and execution; new market identification and expansion.

As a working mother of four, she has a deep commitment to fellow mothers and their children and devotes her talents to the March of Dimes, where she serves as Chair of the Eastern Pennsylvania, Delaware, and Southern NJ Market Board. In 2024, Shari also joined the Board of Partners in Outreach, a Chester County, Pennsylvania, nonprofit that focuses on closing literacy gaps.

Ms. Kruzinski was named 2018 Female Business Leader of the Year by the Chester County Chamber of Business & Industry. In 2020, she was recognized by the Philadelphia Business Journal and honored with the Women of Distinction award. She was named one of the Top 50 Women Leaders in Banking by Women We Admire in 2024.

Ms. Kruzinski attended Wilmington University and is a graduate of ABA Stonier Graduate School of Banking. She calls Kennett Square, PA home where she and her husband are raising their family.

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.