Born to alcoholic parents, Stearns was diagnosed with dyslexia, failed fourth grade, and fathered a child at the age of fourteen. He graduated high school in the bottom ten percent of his class. By this time, he had developed a drinking habit that rivaled his parents, struggled with a quick temper, and found himself in jail more than a few nights along the way. Inspired by the promise of the American dream, Stearns took control of his destiny. He became the first person in his family to attend college and graduated with a degree in economics from Towson University. Motivated by stories of people who took risks and achieved their grandest ambitions, he boldly moved to California where he worked as a waiter and slept on the kitchen floor of a one-bedroom apartment that he shared with five other recent grads. All the while, Glenn continued to search for new opportunities to rise above his challenges and dared to live his best life.

In just under ten years and with no lending experience, Glenn formed his own mortgage company, Stearns Lending LLC, as well as a settlement company, Carriage Escrow. His settlement company soon became the largest HUD contractor in America. In 2002, Glenn's visionary success earned him Ernst and Young's "Entrepreneur of the Year" Award.