Just days shy of his 20th birthday two decades ago, Cadillac Jack arrived in Atlanta from Myrtle Beach, S.C with a job plenty of jocks coveted: a night job at big-time country station Kicks 101.5 for a very respectable (at least for radio back then) $25,000 a year salary.
But the young Cadillac splurged on a brand new four-door Suzuki Sidekick and a Post apartment rental, quickly saddling himself with a $600 a month rent and $500 a month car payment. That didn't leave much left over.
"I was perpetually broke, eating waffles morning, lunch and dinner," he said. "I'd scrounge for a McDonald's value meal coupon."
He was hungry to learn as well, quickly gaining the respect of his bosses, who gave him room to grow in stature and salary. Last week, just as his 40th birthday passed, he signed a new multi-year contract to stay on as morning co-host of Kicks that pays far better than $25,000 a year.
Over two wrenching decades for radio where consolidation and competition has made the business significantly more cutthroat and corporate, Caddy (as he's known to listeners) has survived three owners, an array of bosses and three different time slots - including a stint on sister station Y106 in the late 1990s.
He's a true rarity in a business notorious for instability.
His secret? "Take direction," Caddy said. "There are so many people who are smarter than I am. I don't have all the answers. I never will be the smartest guy in the room. I need coaching. I need good direction."
In other words, he's humble. He isn't apt to pull a diva-like move. He's adaptable to change. He has no qualms playing nine or 10 songs an hour and not hogging the mic. The music, he says, speaks for the station.
Legendary jock Moby, a mentor and former Kicks morning host, summarized Caddy's appeal thusly: "He plays well with others. Me? Not so much."
As a personality, Caddy will never be the loudest guy on the airwaves. He may not be packed with schtick-filled aphorisms. But he emotes a certain comfortable, easy-going relatability.
"He knows the music. He knows his listeners," said Rhubarb Jones, the former Eagle morning host and now a teacher and fundraiser at Kennesaw State University. "He's grounded. His wife Donna and his kids keep him grounded. He works his tail off. And he has plenty of years ahead of him."
"Caddy still loves what he does and has a tremendous sense of pride to see it done well," added his boss Greg Frey, who runs Kicks for Atlanta-based Cumulus Media. "Caddy’s best trait is his preparation. He’s constantly taking in information, from things in the news to pop culture to Nashville to things people are saying on line in the bank. He’s able to take all that info and put it through the filter of 'what’s important to the audience.' He takes the content and presents it each morning in a fun, conversational way."
While he's very real on the air, his name is very fake. A Myrtle Beach radio programmer bestowed "Cadillac Jack" upon him and unlike, say, John Mellencamp, he was game.
"Call me anything you want," Caddy said. "Just give me a job!"
He will answer to his born name as well: William Choate, which sounds more like an English professor than a radio jock. And on air, he's paired with a woman with a fictitious radio name as well: Dallas McCade. "Dallas and I joke about it on air," he said. "I'll call her Karen. She'll call me William."
And you'll never hear him utter "Don't you know who I am?" He's handed his phone number to fans: "I'll call them back. I'll text them back. We don't think we're above them."
Although he knows about two decades have passed, time references are not his strength. He's not even sure what year he started at the station: he said it was either 1993 or 1994. (Based on his age, it's more likely he began at Kicks in 1993.) He couldn't even remember when he took over mornings at Kicks. (That I know: May, 2006. Here's the blog entry I wrote about Cadillac's rise seven years ago.)
He does remember what he did. For instance, he recalls being so young his first year at Kicks, he wasn't allowed to do promotions at bars because he wasn't legal to sip a PBR. "I had to do Home Depots and Advance Auto Part remotes," he said.
His night show was dubbed "Cryin', Lovin' and Leavin' " featuring gobs of ballads by the likes of John Michael Montgomery, Reba McEntire and Travis Tritt. "We took lots of phone requests," he said, "especially collect calls from state prisons."
He moved to sister country station Y106 around 2006 with a coveted afternoon slot there. "He always sounded older than his age," which helped give him gain credibility, Jones said.
In 2000, Caddy transitioned to afternoons at Kicks when Y106 became older-skewing Eagle. He enjoyed the regular hours, especially as his family grew. (He now has three kids, ages 14, 9 and 7.).
But after Kicks got rid of Moby in 2002, management struggled to find a viable morning show. Remember Bandy & Bailey? Or the blink-and-you-missed-it tenure of Craig Cornett?
Management coaxed Caddy to give mornings a chance. His agent at the time Norm Schrutt said Kicks needed a familiar face in the mornings and he convinced Cadillac that it was a smart career move, despite the lousy hours. "Stations are bult on foundations," Schrutt said. "The morning show is a foundation. Besides that, it pays more."
Caddy said he likes to be in control of things and as a solo jock, that was easy. "I'm an alpha guy," he said. "I admit that. I am partly OCD. I like things a certain way. It was an adjustment period to work with a partner. You can get sidetracked in a group or team. But that ultimately can be better than you planned."
Caddy quickly adjusted to the rhythms of morning radio. But he'll never get used to the lack of sleep. (Few morning hosts ever do.)
"You always have red eyes," Caddy said. "You're always tired, always cranky, looking for your next nap. I go to bed before my kids do. It's always a challenge, especially during the summer."
While his morning numbers haven't been as strong as they were a year ago (especially among 25 to 54 year olds), he doesn't obsess over them. "I could not be happier with what we hear every day," he said. "Kicks is on track."
He also pays zero attention to rival 94.9/The Bull, which has a morning show that features Kristen Gates, his former on-air partner from 2006 to 2009. (He said she was the first person to text him congrats last week after news came out about his contract.)
He has only two presets on his radio: Kicks and All News 106.7. He even sent me a photo to prove it. And his 30-minute drive to and from his home in Milton is frequently enveloped in... silence. "I need the time, especially going home, to process what we did. How could we have done it better? What went well? People has this misconception you only work from 5 to 10. That's not true. I work all day."
He'll jot notes down on his iPhone or read through Tweets, always fishing for material.
"Every morning at 10, I get a brand new blank canvas," he said. "It's my job to figure it out what I want to paint, what I need for supplies. It's my job to walk in and be ready."