This legendary entrepreneur is about to launch a groundbreaking streaming platform. Here is the story of his life
South Side of Chicago, 1966. Eight-year-old James Dentley, one of four children being raised by a single mom in one of the most dangerous neighborhoods in the United States, is playing with his friend, Skip, in the alley behind their houses. More specifically, they’re playing with Skip’s father’s gun. Skip points the weapon at his buddy’s face. He’s joking, but James doesn’t think it’s funny. “Stop, stop, put it down,” he says. Skip obliges. As he does, the gun somehow discharges. The bullet misses them. The boys are unhurt. They are lucky. But for Dentley, the time hasn’t faded the memory of that too-close call moment. “When I reflect on that,” he says today, “I always ask myself, ‘Why am I here?’ There’s got to be a reason I’m here.”
Now 63, there is no question that Dr. James Dentley has left his mark on the world. He’s a philanthropist, a renowned businessman, success coach, and motivational speaker who counts billionaires, celebrities, and thought leaders among his wide circle of personal friends.
Total Life Changes, his mentoring and life coaching business, has improved people’s lives across the globe. Not only has Dentley become fabulously rich himself, he’s helped others achieve financial freedom beyond what they ever thought possible, creating 84 millionaires through his various endeavors in network marketing. His industry-leading public speaking boot camp, Inspired2Speak, continues to produce superstar orators. And he’s got a lot more planned, too — not the least of which is JD3 Media, a multimedia platform that will provide a vehicle for speakers, thought leaders, life coaches, entrepreneurs, and artists to showcase their talents and empower them like never before by giving them control of the content they produce in a way that traditional social media platforms haven’t. It’s exactly the sort of outside-the-box idea that has defined Dentley’s life and made his story an inspiring one.
On the surface, at least, Dentley was born into a nearly impossible situation. There was no shortage of potential pitfalls growing up in his area of the Windy City. Plenty of good kids from the South Side never make it out at all. It didn’t help that young James was a risk-taker determined to live life to the fullest. He and his friends would routinely climb to the top of buildings and trees just to one-up each other, risking death or severe injury every time. He’d stubbornly walk the 30 blocks to and from elementary school through 10 different gang territories, so he could keep the pocket change his mom had given him for the bus.
His parents divorced at 4, and while he still saw his father occasionally during his childhood, their split was more like an earthquake to young James. The aftershocks rippled well into his teenage years. “I had a lot of resentment towards him then,” Dentley says of his dad. Hard as his mother worked to make ends meet, sometimes she couldn’t. But while there may have been a lack of money in the Dentley home, there was never a shortage of laughter and affection. “My mother taught us to think and love,” he says.
His mom remarried twice; both of his stepfathers treated him well, and eventually, he grew to love them, too. Whenever it was possible, his mom made sure her kids were exposed to the wider world and all the beautiful things it had to offer. “She did a really good job of making sure she sent us to piano lessons, she would take us to plays,” Dentley says. One Christmas, when they couldn’t afford to buy presents for each other, the kids made gifts instead. To this day, Dentley and his older sister remember it as their favorite Christmas.
Still, James didn’t much like being broke. And with his father out of the picture, he also felt an obligation to provide for the four women in his life. So, from a tender age, he did anything and everything he could to make a buck. He’d rake leaves in the fall and shovel snow during Chicago’s bitter winters. By age 10, he was taking two city buses to get to a part-time custodial job to help earn extra money for the family.
Clearly, this was a bright and ambitious kid. But Dentley had little interest in school beyond doing just enough to earn passing grades. He had a gregarious personality, but he was also self-conscious about the pimples on his face. Throughout his formative years, his self-confidence ebbed and flowed. That began to change as adulthood approached. He got a job at a Church’s Fried Chicken when he was 17. Around the same time, he also became something of a local celebrity. “I could just dance,” he laughs. “I would work a full-time job at Church’s Chicken. I had money. I had a car. I would go on the other side of town and go to the discos and I would just tear it up. Saturday Night Fever – I lived that.” He’d enter and win dance competitions, making more than enough money to pay his bills. But his dancing wasn’t the only thing that made him stand out. “When I would go there, usually there weren’t a lot of African Americans, sometimes none,” he says. “I knew that there was racism but I didn’t really have a lot of those issues. I got along with everybody.” That ability to connect with people from other walks of life would serve him well later on, too.
When Dentley turned 18, he was promoted to general manager of the restaurant – the youngest GM of a Church’s franchise in the entire country. He was soon snapped up by another chain and moved to Texas, eventually landing in rural Midland-Odessa, of Friday Night Lights fame. For a young Black man from the big city, the culture shock could’ve proved insurmountable. Rather than be intimidated, Dentley embraced the challenge. “I had the best time of my life in Midland-Odessa,” he says. “I realized that I had the ability to be able to work and get along and build relationships with people, no matter what they looked like. I understood that people were people and everybody basically wanted the same things. And that when you smile at people, normally they smile back.”
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.”
Dentley has also been rewarded handsomely for it. If he never works another day in his life (which he has no intention of doing) he says he’ll be able to live comfortably for another three decades at least (which he absolutely plans on doing). He’s used his voice, his optimism, his authenticity — his sheer force of will — to make the world a better place. It hasn’t gone unnoticed. “He always gave back,” says friend and fellow philanthropist Dr. Florence Alexander, who in 2017 was given the President’s Lifetime Achievement Award by Barack Obama in recognition of her community service.
“James Dentley is genuine — he loves people and people love him,” says Kevin Harrington, one of the original panelists on the hit TV show Shark Tank. “He started from absolutely nothing and he has dedicated his life to serving others and inspiring people to have the best life they can possibly have.”
“James is probably one of the most humble guys you’ll meet,” says noted business guru Bill Walsh, another longtime friend. “There’s so many speakers and trainers and coaches today who have two personas: there’s the one that that’s onstage where they think they walk on water, that they’re the greatest thing ever. And they treat people like that. That’s not James. James doesn’t change. “The guy you see on stage is the same guy in real life.”
Life is good these days for Dentley. He married his third wife, Dr. Kara Scott Dentley and the couple has an 10-year-old son. But he’s also had to overcome long odds and plenty of sadness to get to this point. He has endured the loss of his mother, father, his first wife, and stepfather. Each represented its own crushing loss. “My stepfather always believed in me,” he said of his mother’s third husband, a fiercely proud man Dentley would carry to the bathroom when he was dying of lung cancer. Their bond had been formed decades earlier, during Dentley’s formative years. James, loyal as they come, never forgot. “He would talk to me about how, as a Black man in America, I was going to have to operate and understand that we don’t own anything, so you have to be able to deal with people who don’t look like you,” Dentley said. “He prepared me.”
The passing of his mother was the hardest one of all. Even then, she took care of the kids. “She planned her own funeral,” Dentley says. “There’s nothing anybody had to do.” The string of tragedies only brought the siblings closer. “We never fight. We don’t argue. We don’t even disagree,” Dentley says. “We just support each other.”
Dentley knows how lucky he is. He knows he could’ve died in that alley as a kid. Looked at that way, it’s not hard to see how he might view his whole life as a bonus, a game he’s playing with house money. It also means that whatever the future holds, Dentley will continue to control the one thing he can: his attitude. “What I try to share with people through my story is that no matter what you’re going through, there’s a bigger picture and you’ll impact lives because everyone is a great example or a terrible reminder,” he says. “Who are you going to become going through hardships? I chose with intention, two things: That I always try to become better. But I also chose to love people.”
Nobody gets to pick the circumstances they’re born into, of course. You only get to decide how to respond.
“I’ve been happy every day for 20 years,” Dentley adds. “I don’t have bad days, I don’t have up and down, they’re just days. I can be in pain, but I’m still happy. Because I can choose that.”
