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, who is 23 years his junior; the couple has an 8-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.”