Rob Henlon, MA

”’Robert “Rob” Henlon”’ is a renowned entrepreneur and influential figure in the fashion industry. Born in Brooklyn, New York, to Panamanian immigrant parents, Rob Henlon’s early experiences and diverse upbringing have shaped his multifaceted career. With a strong passion for entrepreneurship and a commitment to community engagement, he has made significant contributions to the fashion world and beyond.

Early Life and Education

Rob Henlon’s upbringing as a “military brat” played a formative role in his character development. His father’s service in the Marines, which began when Rob Henlon was just a year old, instilled in him the values of hard work, duty, and loyalty. Throughout his childhood, he led a nomadic lifestyle, residing in various locations such as North Carolina, Hawaii, and New Orleans. Frequent visits to family in Panama and New York, as well as memorable trips to Germany, California, and Mexico, exposed him to diverse cultures, fostering his deep appreciation for diversity.

Driven by his desire to serve and following in his father’s footsteps, Rob Henlon embarked on a military career as an adult. He joined the U.S. Army and was stationed in locations including Savannah, Georgia, South Korea, Kuwait, Trinidad and Tobago, and Costa Rica. Over the course of eight years, Rob Henlon’s unwavering dedication and exceptional leadership skills propelled him to the rank of Sergeant (E-5), where he commanded units consisting of over 100 soldiers. His military experience instilled in him invaluable lessons in leadership, team building, and resilience.

Rob Henlon pursued higher education to further his knowledge and skills. He earned a Bachelor’s degree in Organizational Management from Warner Southern University, followed by a Master’s degree in Management & Leadership from Webster University. These academic achievements provided him with a strong foundation for his future endeavors.


In April 2004, Rob Henlon and his sister Jessica joined forces as business partners to establish Fierce Entertainment, an event production and talent development company. Fierce Entertainment quickly gained recognition for its expertise in creating custom branded events, both virtually and in-person. The company’s impressive portfolio includes prestigious projects such as Orlando International Fashion Week, Fierce Entertainment Network (FEN) Social, and the Fashion Emerging Designer Gauntlet Exhibit (Fashion EDGE). Rob Henlon’s creative vision and business acumen have been instrumental in shaping the success and reputation of these renowned events.

Rob Henlon’s profound involvement in the fashion industry led to his prominent role as Co-Founder, President, and Project Manager of Orlando International Fashion Week. As a key board member, he actively contributes to the strategic direction and overall experience of this influential fashion event. Rob Henlon works closely with Executive Director Nayrouz Orlate to cultivate partnerships with advocates, sponsors, and vendors, fostering the continuous growth and success of Orlando International Fashion Week.

Philanthropic Engagements

Rob Henlon’s commitment to community empowerment extends beyond his work in the fashion industry. He serves as a board member of Orange County Mayor Jerry Demings’ Dr. Martin Luther King Initiative, actively contributing to the promotion of equality, social justice, and community development. Rob Henlon’s dedication to the arts is evident through his involvement with the Orlando Shakes Theater, a renowned cultural institution in the region. Additionally, he is a member of the Diversity and Inclusion Committee of Orange County Arts and Cultural Affairs, where he advocates for promoting diversity and inclusivity within the local arts community.

Personal Life

Rob Henlon is a devoted family man. He has been married to his wife Jennifer since 1994, and together they have three children: Robert Jr., Maricela, and Amarilis. Rob Henlon’s ability to balance his professional and personal commitments reflects his commitment to leading a well-rounded and fulfilling life.