By: Alexandra Perez
Monica Challingsworth has always believed in creating environments where people can thrive. As the co-founder and president of Eustress and Demeter, her journey from uncertainty to success in the hospitality industry reflects her determination to redefine leadership. Guided by her mother’s advice to “have faith in yourself,” Challingsworth has transformed challenges into opportunities, fostering innovation, community, and mentorship. Her story is a powerful reminder that leadership is more about serving others than achieving personal success.
Intense challenges marked the early days of Eustress and Demeter. “Every day was either the greatest day of my life or the worst day of my life,” Challingsworth recalls. Juggling fears, finances, and responsibilities, she focused on ensuring that her business decisions reflected integrity and purpose. “We wanted to give people a better environment to work within,” she explains. This desire became the foundation of her company’s ethos: making better decisions for clients and employees.
Challingsworth’s leadership philosophy emphasizes collaboration and empathy. She believes that fostering loyalty within a team starts with valuing individuals as people, not just workers. “If they don’t feel valued, they might always be looking over their shoulder,” she reflects. Decisions at Eustress and Demeter are made collectively, considering what’s ideal for the team and their clients. For Challingsworth, leadership isn’t about asserting authority—it’s about shared purpose and mutual respect.
Her groundbreaking hospitality-concept, Dink and Dine, exemplifies this philosophy. Combining pickleball with elevated dining, Dink and Dine is more than an “eatertainment” venue—a community hub that fosters connection. “It’s about creating spaces where everyone feels respected,” she shares. From providing a comfortable break area for delivery drivers to offering college book stipends for team members, Dink and Dine sets a new standard for hospitality. The concept is a testament to Challingsworth’s ability to integrate innovation with care, ensuring that every detail contributes to a culture of inclusion and respect.
Challingsworth’s commitment to building better workplaces stems from her own experiences. During her tenure at Seasons 52, she was initially met with resistance from the local community but turned the situation around through relentless relationship-building. “I had a goal to collect 50 business cards daily,” she laughs. Her efforts paid off, and the experience taught her the value of persistence and engaging with the community.
Mentorship has also played a significant role in her journey. Guided by her mother’s unwavering support and the tough-love guidance of her business mentor, Helen Lao, Challingsworth has developed a leadership style that balances compassion with accountability. Her mother’s mantra, “You’re the only person who can fall into a pile of mud and come out shining,” constantly reminds her of her resilience. “I trust myself implicitly to make the right choices,” she shares, crediting her mentors for helping her find her voice and strength.
As a mentor herself, Challingsworth is dedicated to empowering women in the hospitality industry. Through initiatives like the Gleam Network, she helps mentees navigate challenges, find their voice, and align their decisions with their values. “It’s about creating a safe space for vulnerability,” she explains, emphasizing the importance of collaborative growth over competition. Her approach reflects her belief that leadership is about uplifting others and creating opportunities for collective success.
At Eustress and Demeter, Challingsworth has redefined what it means to connect with customers. She believes that emotional connections are built through intentional moments of care. “People want to feel seen, valued, and understood,” she explains. Whether remembering a customer’s favorite dish or crafting an unforgettable event, her approach is rooted in authenticity and storytelling. These elements inspire loyalty and set a new benchmark for customer engagement in the hospitality industry.
Looking ahead, Challingsworth has ambitious goals. Over the next five years, she plans to expand Eustress and Demeter’s impact, creating programs that combine sustainability with profitability. “Real innovation happens when growth and responsibility go hand in hand,” she states. Her vision includes mentoring the next wave of leaders and designing strategies that bring joy and meaning back to hospitality. For her, success is about leaving a legacy that uplifts both businesses and the lives they touch.
Monica Challingsworth’s journey is a testament to the power of resilience, empathy, and purposeful leadership. From transforming doubt into determination to mentoring the next generation, she has redefined success as balancing personal growth and collective impact. Her story inspires others to lead with integrity, embrace challenges, and create spaces where everyone can thrive.
Published by Charlie N.
