By Char Ravelo

Spencer, Sophia and Mark Gregory in Italy. Contributed photo

Imagine a young boy at summer camp each year and taking notice of the leaders around him. He grows up realizing their contributions in creating, organizing, and operating the camp, as well as training the future leaders. Impressed by their positive impacts, this young man decides to follow in their footsteps. Showing eagerness, he is given responsibilities and soon is leading groups within the camp.

After college he joins corporate America. He lands a job at Intuit in 1990, where he is selected by his colleagues to collaborate with the president and CEO in revising the company’s vision, mission and operating values. Those extraordinary founders were awe-inspiring role models.

Fast forward to today on Kaua‘i, where a small and mighty IT company has a fearless, caring, employee-centered, honest and forthright entrepreneur and CEO, Mark Gregory of IT Kaua‘i.

Mark has a servant leadership style with his staff as the top priority. Similar to camp, he strives to create a positive environment for his employees to perform at their optimum, making sure they have everything they need to be successful. “We celebrate wins and discuss losses, acknowledge accomplishments, and encourage growth in one another,” Mark said.

Mark developed his style from both positive and negative experiences with bosses and colleagues. “Everyone is your mentor, but not everyone knows it. Gold nuggets are not always found in a great manager, boss, or colleague. You can learn just as much from negative experiences and sometimes more. We’d all rather learn from positive experiences but that’s not how life is.”

With a shortage of seasoned IT techs on Kaua‘i, Mark pivoted to hiring qualified and trustworthy individuals though relatively new to the industry. A natural teacher, he mentored them from the ground up to become independent. To hear “I got this or I’ll take that” on the floor means success. His mantra is, “Only seek out win-win situations. If one person loses, everyone loses.”

Along with empowering role models in his corner, Mark has unwavering faith and trust that things will work out. As chaotic as life gets, he finds a calm in this inner knowing.

Mark Gregory. Contributed photo

Entrepreneurs take a special kind of risk. In a Forbes article, researcher Sally Caird calls it “calculated risk taking” and describes it this way: “Calculated risk-taking is operationally defined as the ability to deal with incomplete information and act on a risky option, that requires skill, to actualize challenging but realistic goals.”

Successful entrepreneurs are experienced calculated risk takers, and they take leaps of faith to move their businesses forward. Mark does this daily as he legacy builds with his employees and his two children who also grew up in the business. Like his inspiring mentors, he hopes to lead by example in encouraging others to trust themselves and leap towards their aspirations.

What gets him up in the morning? Mark replied, “The smell of brewing coffee, actually, I am excited for Mondays because it is a fresh start on a new week.”

His favorite quote is: “Slow is smooth and smooth is fast.” — Navy Seals

  • Char Ravelo is the Executive Director of Leadership Kaua‘i, and can be contacted at or (808) 246-8727.






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