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Dentley grew to respect his father, a well-liked man but one of few words. He owes his relentlessly optimistic and unfailingly sunny disposition to his mother, Loretta June Dentley. He inherited the gift of gab from her, too. “Oh, we’re clones,” James says. This is not to suggest that he didn’t struggle through hard times or bouts of self-doubt. Back in Chicago in his mid-20s, Dentley contracted a skin disease that left behind scar tissue and made the hair on the back of his scalp fall out. Then he got a blood infection that left him in excruciating pain for years. “I wanted to die,” he says. “I wanted to kill myself.” The nightclub he owned was failing and he spent all his time and money trying to keep the doors open. He hated it. The stress broke his first marriage up. He was separated from his daughter, Paris. “That was one of the times I learned the key lessons about perseverance, endurance, faith, hope, and how to be able to move past the perceived pains because it gave me a story to tell and it took me to another part of my life,” Dentley says. “It taught me not to quit, not to give up, and not to try to take the easy way out.”

After he divorced, he needed a fresh start. He shuttered the club and his other Chi-town businesses and moved to Atlanta. It wound up being the best thing he ever did. It sure didn’t start out that way, though. Soon after arriving in Georgia, in 1994, Dentley began working for a fledgling telecommunications company called ACN whose aim was to compete with giants such as AT&T and Sprint by offering lower long-distance rates. He was asked to prepare an oral presentation due in two weeks. He was scared stiff. “I went home and practiced every night, every day,” he says. “Three o’clock in the morning, I’m talking to doorknobs. I’m sweating bullets.”

The combination of work ethic and natural charisma he’d displayed his whole life paid off; Dentley crushed his first public speaking assignment with a preview of the same easy and engaging style that has won over countless audiences across the globe in the decades since. In that way, he never looked back. Still, lasting success in Atlanta was elusive at first. Once again, Dentley saw the adversity as an opportunity to grow. “The first time I ever had to sleep in my car, I remember putting my little comforter over my head with everything that I own in the backseat, and I said, ‘I’m going get rich,’ ” Dentley says. “I just looked at it like Viktor Frankl in Man’s Search for Meaning. You see two men both trapped behind prison bars. One man saw the mud, the other man saw the stars. I chose in that moment to see the stars and said, ‘OK, I tried every way I can to become successful. Maybe this is the road.’ I kept an upbeat attitude.”

At the same time, Dentley kept thinking about the story that ACN’s co-founders, twin brothers Mike and Tony Cupisz, recited often, about how they were homeless at 24 and millionaires by 28. “I understood that in those testing times – and I was told that I would be tested – that I had a choice I could make in that moment. What would I see when everything is going bad? What can I see? Who could I become in those moments?” They were questions he needed to answer on his own. As tight as he was with his mother and three sisters, Dentley communicated with them solely via mail in 1994 – a year that turned out to be something of a pivotal one for him. He didn’t dare call out of fear that he’d spill the fact that he was couch-surfing at colleagues’ apartments on nights when he couldn’t afford to pay the $35 for a night at the Red Roof Inn. “When I was going through the toughest times, they would have saved me as they’ve always saved me,” he says. “I didn’t need to be saved. I needed to grow up and take responsibility.” While he knew his family would insist on wiring him some cash, there was another reason he didn’t call home. As much as the Dentleys provided a loving and safe space, they were nothing if not practical. They would’ve implored James, ever the dreamer, to stop chasing fame and fortune and go get a steady, boring, regular job. Dentley wanted no part of that conversation. He didn’t want a normal life. He wanted an exceptional one. “There had to be more,” he says. “I think that was really it.”

Other challenges would emerge along the way. His second marriage also ended in divorce, one of the few regrets Dentley says he has. He did a stint in rehab in the early 2000s for alcohol dependence, a particularly painful low point. Over time, though, he was able to detect a pattern. He realized that if he was struggling in one particular area of his life, it was only a matter of time until it seeped into others and threw him off his axis entirely. It’s how he identified as “The 5 Frequencies of High Performance” — a blueprint for personal success that would become the title of one of his best-selling books. It gives readers tools they can use to bring their spirit, mindset, physical body, relationships, and financial stability into alignment. Dentley learned those lessons the hard way. He hopes others can learn from how he responded to his own setbacks. “He was always a hard-working guy and an extremely good communicator who was good at anything he did,” says former NBA All-Star Mark Aguirre, a fellow Chicagoan and a close friend of Dentley’s since the late 1970s. “But the biggest part of his story that sticks out to me is the way he transformed his ability from helping himself to helping others. He’s unselfish with his talent.”

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Tom Chesser

Tom Chesser is the owner of Rise Up Media and Marketing. He has a featured show Rise Up Radio, an online broadcasting podcast. He is a credited contributing writer for Small Business Trendsetters, Business Innovators Magazine, and host for Business Innovators Radio. He has his own Authority Agency in San Antonio Texas serving all of Texas & beyond. Tom is a Top-Performing Professional in the Media and Marketing industry with over 30 years of experience.