Fearless Growth in Hospitality: Building Without Losing Your Culture with Sydney Grims (Ep. 18)
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:
Connect with Bryn Mawr Trust:
- 833-973-7633
- LinkedIn: Bryn Mawr Trust
- Website: Bryn Mawr Trust
Connect with Kate Duffy:
Connect with 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.
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