Michael Bennett grew up in a small two-bedroom home with nine people, where his father owned a junkyard and truck repair shop. From age 7, he cut grass and later packed boxes at the Old Tomato Sheds on Johns Island, learning the value of punctuality and hard work.

Bennett attended the University of South Carolina but left after two years to pursue his entrepreneurial journey. At 20 years old, he started renting bicycles and mopeds on Market Street, discovering he liked being his own boss. That bicycle rental business launched what would become 50 years in the hospitality industry.

Today, Bennett leads Bennett Hospitality with 1,300 employees worldwide, making him the largest local owner of hotels, restaurants and venues in Charleston. His Hotel Bennett has been listed as one of the finest hotels in the world by Conde Nast. With several hotels under construction and more developments in the pipeline, Bennett works with a small team of employees and family members.

“I don’t dwell on challenges, only opportunities,” Bennett said, reflecting on his approach to business and life.

Craig Brown leads Greenville Drive, a Minor League Baseball team and Single A affiliate of the Boston Red Sox. Before entering sports ownership, Brown spent 23 years as a key executive in the globalization of the advertising industry, most recently as president and chief operating officer of Bcom3 Group, the fourth largest advertising agency in the world.

Brown led the construction of Fluor Field, the Drive’s award-winning stadium, and serves as a founding board member of MiLB Enterprises, which oversees brand marketing for Minor League Baseball. His community involvement includes serving on the Greenville Health System’s Strategic Coordinating Organization Board, chairing the Advisory Board of the Medical Experience Academy and co-chairing the ACCELERATE! Greenville Initiative.

Brown also serves as senior vice chairman of the Hydrocephalus Association and on several boards at his alma mater, Michigan State University. In addition, he received the Order of the Palmetto in April 2025.

Hope Caldwell earned her Bachelor of Science in Hospitality Management from Johnson and Wales University before establishing herself as a leader in the hospitality and tourism industry. As Principal of KLH Group, Caldwell leads the 10-person firm with a focus on purpose-driven business practices.

Beyond her professional role, Caldwell co-founded Doors to Dream, an organization engaging underserved youth to activate their potential and gain access to opportunities. She also co-founded The Spokes Group in Charleston, which has provided over 1,500 bicycles to underprivileged children since 2012, raising between $15,000 and $35,000 annually.

As a board member for OneWorld Health, Caldwell led medical mission trips to Uganda, overseeing teams of 40 volunteers and coordinating with onsite partners to deliver sustainable healthcare to underserved communities.

“Don’t let perfection get in the way of excellence,” Caldwell said, describing advice that has shaped her approach to leadership.

An author, speaker and marathon runner, Caldwell has impacted 246,000 people through her various initiatives, embodying servant leadership across professional and philanthropic endeavors.

Retry

Tia Clark built her Charleston-based crabbing tour company on two decades of food and beverage industry experience, transforming local waterways into an educational adventure for residents and visitors alike. As CEO of Casual Crabbing with Tia, she leads a team of seven while serving on multiple environmental boards.

Clark’s commitment to marine conservation extends through her volunteer work with Charleston Waterkeepers, the Marine Advisory Committee for the South Carolina Department of Natural Resources, and The Good Catch sustainability board at the South Carolina Aquarium. She also serves on Airbnb’s Experience Host Advisory board.

Her industry leadership earned recognition in The Explorer’s Club’s EC50 class of 2025, highlighting 50 individuals changing the world. “I define success by the feeling I get waking up every day,” Clark said, noting her transition from restaurant management to entrepreneurship filled a professional void.

Clark’s career began at McDonald’s, where she learned teamwork fundamentals that shaped her hospitality approach. Beyond business, she’s an avid billiards player who once competed on an eight-ball pool league.

Heath Dillard leads VisitGrenvilleSC as president and CEO, bringing extensive hospitality and tourism expertise to South Carolina’s destination marketing. Dillard earned his Bachelor of Science in Business Administration from the College of Charleston and MBA from the University of North Carolina Charlotte.

His career began with manual labor for an electrical subcontractor, followed by minor league baseball operations where he gained broad business experience. This foundation shaped his multifaceted leadership approach.

As a Certified Destination Marketing Executive, Dillard currently serves on the Greenville Chamber of Commerce Board of Directors, Metropolitan Arts Council Board of Directors and Travel & Tourism Research Association International Board. He is a Leadership Charlotte Class 38 member and Riley Fellow at Furman University.

Under Dillard’s leadership, Greenville has secured notable achievements including hosting Top Chef Season 23, the inaugural Michelin Guide American South Ceremony and a three-year SEC Women’s Basketball Tournament contract extension through 2028. “Right is right, even if no one is doing it,” Dillard said, reflecting his guiding philosophy.

Rick Erwin began his restaurant industry career as a dishwasher at age 14, gaining firsthand experience in hospitality operations from the ground up. After dedicating 23 years to Ryan’s Family Steakhouses, he founded the Rick Erwin Dining Group in 2005, opening his first establishment, Rick Erwin’s West End Grille, in Greenville.

The upscale restaurant group has since expanded to operate seven eateries across South Carolina’s Upstate region, with locations spanning Greenville, Spartanburg and Clemson. The group’s diverse portfolio includes Rick Erwin’s West End Grille, Rick Erwin’s Greer, Rick Erwin’s Eastside, Rick Erwin’s Level 10, The Vista, Rick Erwin’s Clemson and Rick Erwin’s Nantucket Seafood.

Erwin’s establishments have earned multiple accolades, including the OpenTable Diners’ Choice designation and the Wine Spectator Award of Excellence, recognizing both service quality and culinary standards. The group launched its charitable initiative, Crab Cakes for a Cause, last year, demonstrating its ongoing commitment to community engagement alongside exceptional dining experiences throughout South Carolina.

Jeff Goldklang serves as owner and vice chairman of the Charleston RiverDogs, leading a sports entertainment organization with 90 employees. He earned a Bachelor of Arts in political science from the University of Rochester before beginning his career at Integrated Sports International, which was acquired by SFX Sports Group shortly after he joined. There he worked in the marketing division of a major sports agency representing NFL, MLB and NBA clients.

Goldklang’s leadership philosophy emphasizes creating an engaging workplace culture in the baseball industry. “Our employees work their butts off. We try to always make it as much fun as possible and allow them to enjoy the fact they work in baseball,” he said. The RiverDogs organization focuses on providing affordable family entertainment while maintaining high-quality production, food and hospitality services.

In 2025, the team received Major League Baseball’s Community Award, given to one minor league team among 120 franchises, and made the largest charitable cash donation of any minor league team at over $100,000.

Helen Hill has led the Charleston Area Convention and Visitors Bureau for 30 years, representing 849 member businesses and nine municipal governments in Charleston and Dorchester counties. Hill’s Charleston upbringing provided insights she applies to marketing the region as a destination. The bureau’s creative marketing programs have helped Charleston area accommodations achieve one of the highest success rates in the country.

Hill serves on the US Travel Association board and holds board positions with the Charleston County Aviation Authority and Southeastern Wildlife Exposition. She previously chaired the South Carolina Association of Tourism Regions and Southeast Tourism Society. Hill received the Fred Brinkman Award for Outstanding Tourism Leadership in South Carolina as the first woman and fourth person honored. Afar Magazine recently recognized her as a Vanguard of Travel.

Hill volunteers with Ashley Hall School and Clemson University, where she earned a Bachelor of Science in Parks, Recreation and Tourism Management. She lives downtown with her family and enjoys walking, biking and boating.

Starting as a shelf stocker at a Winn-Dixie Supermarket and teaching private trumpet lessons on the side, Matt Hollander has built a career he loves. Now, he has more than 35 years of industry expertise, working in convention centers, arenas, theaters, and amphitheaters. As the general manager of the Greenville Convention Center today, Hollander is described as a servant leader, where he’s responsible for the management, promotion and operations of the facility. He’s passionate about introducing Greenville to people looking for a conference, meeting, or event location.

Some of Hollander’s other professional experiences include direct leadership of a destination marketing organization and a sports commission, the oversight of design and construction of new venues, renovation and expansion of existing venues, and helping oversee ongoing capital improvement projects.

Away from work, Hollander was recently elected as the second vice chair of the International Association of Venue Managers (IAVM) board of directors. He also joins the board’s senior leadership team and has begun a four-year officer rotation to ultimately serve as chair of the board for the 2027–2028 term.