Meet Cloud Bobby

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The story below is from our September/October 2022 issue. For more stories like it, Subscribe Today. Thank you! 

Cloud Bobby left a successful career to pursue his passion. Now he’s one of Virginia’s top music photographers.

Roanoke-based shutterbug Cloud Bobby jostled left through the stage-center crowd as Rooster Walk Music & Arts Festival 2022 headliner Grace Potter & The Nocturnals kicked into a raucous encore. His fellow staff photographers pushed right, but he had a feeling.

“My gut was telling me she was about to do something wild and totally off script, and I just went with it,” says Bobby, 50.

Suddenly Potter pulled the mic from the stand, dashed left and launched herself into the air. Bobby was in perfect position to capture the moment. Colleagues pounced the instant he ducked into the press tent after the show.

“I was getting fist bumps, elbow daps, everybody was like, ‘Dude, you got the shot, you got the shot!’” says Bobby. “It blew me away — I mean these were guys and gals I admired and looked up to; like, serious professionals.”

It was a moment Bobby had been working toward since officially launching his music photography and videography business around 2017. By Rooster Walk he was established as one of the Roanoke area’s top music photographers and routinely shot for venues like the 5 Points Music Sanctuary, Elmwood Park’s summer music series, Martin’s Downtown Bar & Grill, the Jefferson Center and more.

“Bobby is an amazing photographer and consummate professional,” said 5 Points Music Sanctuary executive director Tyler Godsey in a statement. “His work speaks for itself, and we are incredibly grateful to have him on our team.”

Still, the praise from the Rooster Walk pros felt different.

“That’s when I knew I was really making it,” says Bobby. “I could finally say with confidence this wasn’t a midlife crisis, that switching careers to pursue my passion full-time had been the right move.” 

Bobby’s family relocated from Long Island to Roanoke around 1980. His love of visual art started with sketchbook doodles, progressed to paints and canvas, then found its outlet in street art.

“I got really into it,” says Bobby. He worked obsessively through his teens and early 20s, honing his craft and building recognition around a tag-name. Shows in noteworthy regional galleries followed.

“It was a great time in my life,” Bobby says. He was living with a band of musician friends. Though he didn’t play an instrument, he was inspired by the form’s emotional expressiveness and kineticism. “I started experimenting, trying to find ways to channel that feeling, that sense of movement and ephemerality into my art.”

Then circumstance intervened. Bobby’s girlfriend was pregnant. They married and Bobby used his carpentry skills to support his family. He built a successful construction business, had more kids, bought homes, took family vacations. Twenty years passed.

Then something happened. Bobby had been following advances in digital photography and was awed by the groundbreaking capabilities of programs like Adobe Photoshop. He became intrigued by boundary-pushing artists.

“I could see a lot of them were using techniques similar to what I’d used for my street art,” says Bobby. That overlap “piqued my interest and drew me in.”

He bought a drone on a whim and started spending evenings snapping aerial photos of forests, sunsets, wildlife and more. Critiquing the pics, he realized something was missing: Himself.

“There’s a big difference between a photo of a landscape and how it felt to be there experiencing the real thing,” says Bobby. He wanted his photos to capture the latter — and obsessed about it.

Bobby bought a pro-grade camera, computer, lenses and software. Soon he was spending all his free hours reading how-to books, watching online instructional videos and experimenting with taking and editing pictures. A work friend — who played with The Jared Stout Band and rising country music sensation Morgan Wade — discovered Bobby’s new hobby, and invited him to photograph some live shows.

The shoot brought an epiphany. Bobby loved how the band’s energy fed the crowd, and the crowd’s fed the band. He didn’t know the songs, but seemed to sense when a photographic moment was about to happen — one that could capture the euphoric joy of dancing in an audience of hundreds.

“It was amazing, I’d never experienced anything like it,” he said. “I was totally green, missing shots left and right. But I got close a few times, and that left me determined to get better. Everything inside me was screaming: ‘This is what you’re supposed to be doing!’”

Bobby went home, analyzed finances, drew up a budget and drafted a secret five-year plan to transition out of construction and into full-time photography.

“I was quiet about it because I didn’t want [friends and family] to think I was having some kind of midlife breakdown,” says Bobby, laughing. “They already thought I was crazy for devoting so much time to it, and I didn’t want to fuel their worries.”

He honed his craft photographing as many Jared Stout and Megan Wade shows as possible. He broke in with other bands by offering to help setup equipment in exchange for backstage passes to shoot the performance. Tagging photos of groups and venues on his social media channels led to paying gigs at local music havens like 5 Points, a nonprofit that donates proceeds to help children with hearing impairments and fight hearing loss.

Bobby’s reliability, aesthetic pizazz and ability to capture intimate musical moments awed managers — and inspired them to book him for steady work. For instance, Bobby is now on freelance retainer at, among others, 5 Points and the Jefferson Center. Word got out and offers trickled in from major regional festivals like Floyd Fest and LOCKN’.

Then came pandemic shutdowns. But Bobby refused to let them stop him. He partnered with Roanoke-based stage, sound and lights company, 81 productions, on a livestreaming concert series to help bands stay together and afloat during lockdown. The Space Shop Sessions featured groups like Virginia Electric, Jared Stout, Isaac Hadden Project and Half Moon Band. Bobby used them to level-up his videography skills and learn more about production.

“I’m a silver-linings kind of guy,” he says. “This was a way for us to help everyone stay sane, keep our chops up and bring people together in a time when we were further apart than we’d ever been.”

Bobby says business skyrocketed with the lifting of pandemic-related restrictions. He’s photographed Rooster Walk, Red Wing Roots Music Festival and is again booked at Floyd Fest, which averages daily attendances around 13,500. The success has left him dreaming of next steps: Buying an RV to work the national festival tour.

“People ask me, ‘Why on earth would you want to leave a successful career to do something crazy like this?’” says Bobby. “And I tell them, from the moment I picked up that camera and started taking pictures of bands, it’s all I’ve wanted to do. I’m addicted — it’s given me a sense of fulfillment I didn’t know was possible.”

Five years ago, Bobby didn’t think his business plan would really work. But now that it has?

“I bought the ticket,” he says. “So, I’m damn sure gonna’ take the ride!”

The story above is from our September/October 2022 issue. For more stories, subscribe today or view our FREE digital edition. Thank you for supporting local journalism!