By Alexandra Perez
Monica Challingsworth, the dynamic co-founder and president of Eustress and Demeter, has made it her mission to challenge traditional notions of leadership and hospitality. Over the past eight years, her innovative approach has transformed businesses, inspired individuals, and redefined the purpose of leading with purpose. By combining her entrepreneurial spirit with a deep commitment to mentorship and community, Challingsworth continues to raise the bar in an industry often described as grueling and thankless.
Challingsworth’s career trajectory is a study of resilience. When she and her colleagues were laid off after their company was acquired, she initially expected to return to the traditional workforce. Instead, a series of referrals and consulting opportunities paved the way for Eustress and Demeter. “We never really planned to do this,” she admits, but the challenges they faced early on only strengthened her resolve. For Challingsworth, each obstacle became an opportunity to create something better—for her team, her clients, and the industry.
The belief that hospitality is about human connection is at the core of her work. Eustress and Demeter focus on building emotional bridges between businesses and their customers, crafting experiences that leave lasting impressions. “People want to feel seen and valued,” Challingsworth emphasizes. This philosophy has shaped every aspect of her company, from training programs to client strategies. It’s not just about boosting revenue; it’s about creating meaningful connections that resonate.
Her passion for innovation shines through in her latest venture, Dink and Dine. Designed as an “eatertainment” destination combining pickleball courts with high-quality food and beverage options, Dink and Dine is a testament to Challingsworth’s ability to think outside the box. The concept prioritizes accessibility and inclusivity, addressing the challenges faced by players and enthusiasts in traditional pickleball spaces. “We want everyone to feel welcome,” she explains, pointing to initiatives like open courts for newcomers and community events that encourage engagement.
Challingsworth’s dedication to people extends beyond customers and clients—it’s deeply rooted in her leadership style. At Dink and Dine, her approach to team-building emphasizes understanding and supporting employees as individuals. From offering college book stipends to creating comfortable break areas, she ensures that her team members feel valued and empowered. “If you take care of your team, they’ll take care of your business,” she says. This people-first philosophy has become a cornerstone of her success.
Significant milestones have also defined her journey. Winning the Century City Chamber Champion award remains one of her proudest achievements. At the time, she was the youngest recipient and the fastest to earn the honor, a testament to her relentless work ethic and community engagement. “I set out to be the biggest champion of the chamber,” she recalls. Through hosting events, building relationships, and immersing herself in the community, Challingsworth demonstrated the power of perseverance and the importance of collaboration.
Mentorship has been another defining element of her career. Guided by her mother’s advice to “have faith in yourself” and the tough-love mentorship of Helen Lao, Challingsworth has learned the value of balancing compassion with accountability. These lessons have not only shaped her as a leader but also inspired her to mentor others. Through initiatives like the Gleam Network, she helps young professionals—particularly women—navigate the challenges of the hospitality industry. “It’s about creating safe spaces for growth and vulnerability,” she explains.
In an industry that often prioritizes profit over people, Challingsworth’s approach is refreshingly different. She believes that sustainability and innovation are essential for long-term success. At Eustress and Demeter, she integrates these principles into every project, ensuring that clients’ growth is not only profitable but also responsible. “Real innovation happens when growth and responsibility go hand in hand,” she asserts. This mindset positions her as a trailblazer, pushing the boundaries of what’s possible in hospitality.
Looking ahead, Challingsworth’s vision for the future is ambitious yet grounded. She plans to expand the impact of Eustress and Demeter, mentor the next wave of leaders, and continue reshaping the hospitality landscape. Her ultimate goal is to create systems and strategies that not only drive revenue but also bring meaning and joy back to the industry. “Hospitality is about connection and transformation,” she says. “That’s what I want to be a part of.”
Monica Challingsworth’s story is one of perseverance, innovation, and a relentless commitment to others. From building groundbreaking concepts to mentoring future leaders, she has redefined what it means to succeed in hospitality. Her journey serves as an inspiration for anyone looking to lead with purpose, proving that true success is about creating a positive impact—one connection at a time.
Published by Charlie N.
