If there’s one thing I’ve learned over the years, it’s that it never hurts to ask. Case in point: a few weeks back I got an assignment from The New York Enterprise Report to photograph A&M/Octone CEO James Diener for the cover of the March issue. I’ve been shooting bands for years, but I don’t think I’ve ever taken a portrait of the people behind the artists I love.

After spending a half hour scouting out Diener’s office for a good portrait spot, we settled on taking his photo in front of a guitar against a very colorful blue wall. The shot would be “safe” and it included a musical element, which works well with what the subject does. Only one problem—the guitar was a three-quarter scale axe, which while sentimental to Deiner wasn’t exactly cover material.

So we headed off to his home to select another guitar from his massive collection. “Wow, nice butterscotch Telecaster you have there Mr. Diener,” I prattled trying not to let him notice the drool coming down my chin. “Why that’s a Fender Broadcaster—it came before the Tele and only a handful exist,” he corrected me and hopefully didn’t see me faint.

We went back to the office with a slick Les Paul that was probably worth more than me (stunning flame-top) and proceeded to knock out the shot I had tested earlier with my fabulous art director Tony Gamino. I actually like Tony’s portrait a tiny bit more, but it might be a tad bit too edgy.

During the shoot, James mentioned that he was a magician. I asked, in passing, if we could do a shot for the inside spread at his house while he’s doing some sort of card trick. To my shock, he canceled an appointment and told me to pack up my lights and head back to his place.

A few minutes later I’m in his condo taking the portrait below with only one flash firing through an umbrella (camera left). He made some calls, I photographed him doing a slight of hand card trick, and away we went. Sadly, the photo was held from the magazine because his magic hobby wasn’t included in the piece. That said, I still had a really fun time capturing the head of a major record label in his personal environment and got to prattle endlessly about my love for Iron Maiden and D-Generation with someone who actually knows what I’m talking about.