Right off the bat, he was asked how he landed the Del McCoury Band to play on his eponymous debut album. It turned out Bentley and the bluegrass icons have been friends since he came to Nashville, and he was in fiddle player Jason Carter's wedding.
"In fact, the first time I really became aware of POLLSTAR was when they were on the cover," Bentley said. "Did you write that? Man, that was such a good article, such a great cover with them around that crap table."
Oh, stop it! In about 20 minutes.
"I was so excited for them, and they were excited about it because those are the guys I look up to as far as touring and keeping a busy schedule."
He's taken the Del McCoury Band's philosophy as his own. Along with supporting George Strait and Kenny Chesney this year, he's told his agency, William Morris, his goal is to do 150 dates in '04 - from colleges to dive bars.
Yes, he's going to the fairs, too, but he and WMA are working on making him a hard- ticket act.
Bentley had a recent hit with "What Was I Thinkin'" and has been touring non-stop since July. He did 24 shows in October and didn't see his Nashville home the following month. From July through December, he and his band played 80 times.
Bentley's story of an up-and-comer is not unusual for Nashville - on the surface, at least.
However, he is unique in his amount of business savvy. He is a Vanderbilt alum who kind of wandered into country music.
He came to Nashville in '95 (at the age of 19) from Phoenix and played three nights a week at various clubs. He was a regular at The Station Inn, even tending bar and cutting grass. One time, he got Vince Gill and Amy Grant to join him onstage at the Market Street Brewery.
After he arrived in Nashville, he interned at the Country Music Association and even answered phones at William Morris for a week while he roomed with Jay Williams - his future agent.
For a long time, his day job was at The Nashville Network, where he was paid to look through old video footage of performances for a miniseries called "A Century of Country."
Through it all, he developed an affinity for the smoky bars and the "band" mentality.
"In many country bands, the rest of the band dresses in black and they stand behind their monitor and they're out of the way, and they're kind of ignored. That's just never done anything for me as a fan or a player. ... It's my name on the marquee, but I think it's a lot more fun to watch a band."
To that effect, guitarist Rod Jansen and bass player Michelle Poe play side-by-side with Bentley. They've pulled the bus into many a small bar, knowing they wouldn't make much dough but would have a chance to win over 300 more fans and get a chance to cuss and have fun.
"We trade shows with Cross Canadian Ragweed. I love the places they play and the crowds they have. It's just a young crowd that hungers for music and loves to listen."
In true Nashville style, Bentley got his team together in reverse. He did everything from "a musician's standpoint" by first concentrating on the music then signing with Williams even before he had a record deal.
"The manager was the last person and I couldn't live without Scott (Kernahan) now. He was the last person but the most important person I have. It's such an important decision, your manager. He's booked a lot of country acts but he's more of a rock fan, and that's the approach I try to take with touring.
"I really love playing those smaller clubs and bars where there's a lot of younger kids drinking beer and pressing up against the bar with their beers and having a blast. It makes you feel like a rock star when you're just a country singer."
Bentley said it was Kernahan who helped him land the opening slot for the upcoming Strait gigs. According to Bentley, Strait (a fellow client of the Erv Woolsey Company) usually has a female country artist open but last year wasn't a good one for the ladies as far as radio play was concerned. Meanwhile, Kernahan kept mentioning that Bentley would complement Strait's music, and Strait was a fan of Bentley's record.
For most of the band, it will be their first taste of the arena circuit.
"[Dierks] thought outside the box in terms of how country artists normally tour and I was happy to be a part of that," Williams told POLLSTAR, stressing the hard-ticket strategy. "We went into Athens (Ga.) on a Monday night and almost sold out the (1,000-capacity) Georgia Theatre the first time. That's impressive for a new act - especially for a new country act with only one single, on a Monday night."
The agent said that although the year will be filled with the arena, fair/festival and club shows, nobody has forgotten the college crowd.
"None of this would be possible if the client wasn't as smart as Dierks is and allows those around him to develop the master plan," Williams said. "We can be flexible and go work Monday nights in a college market for lower dough, and Capitol's been great in helping us get the ball rolling early on."
The agent's acts skew slightly "left of center" when it comes to the Nashville formula.
Along with Bentley, he reps Gillian Welch, Nickel Creek and recently acquired Pinmonkey.
Williams said Bentley has listened to all of WMA's advice - except for keeping in a van.
With the ribbing out of the way, he admitted the country singer can afford the bus and - with the kind of dates he puts in - probably could use a home away from home.