Robbie Wheeler is a Nashville-based creative director and photographer who partners with labels to oversee album rollouts — art direction, album covers, music videos, the whole package. He and Isaac had been in the same online creative circles for years without ever really talking, and this episode was their first real conversation. What followed covered a lot of ground: how Robbie’s college shutting down turned into a Nashville career, the photographers he looks up to and why, the love/hate relationship with social media, and the NYC photo book he’s been quietly building toward.
From iPhone 4 in Scotland to Creative Director in Nashville
Robbie didn’t set out to be in the music industry. He took his first real photos on a birthday trip to Scotland at 14 — iPhone 4, no plan, just walking around and shooting. The photos were bad. He still remembers it as the moment something clicked.
From there: high school in Nashville, a college acceptance in New York City, and then his school ran out of money and closed. The plan evaporated. He moved back to Nashville during COVID, bought his first real camera during a gap year, and started shooting seriously.
“I sort of had a camera when I was younger but never really picked one up — and then after that it was sort of my gap year, I took a gap year after high school, COVID hit, and I bought my first camera and yeah it sort of took off from there.”
Nashville turned out to be full of musicians who needed creative work. Robbie reached out through mutual friends, got introduced to more artists, and realized the opportunity was real. He didn’t plan to end up in the music world — it just made sense once he was inside it.
What a Music Creative Director Actually Does
The title “creative director” is vague from the outside. Robbie was clear about what it actually means: a label books him for an album, and from that point he owns the creative side. Album cover, music videos, mood boards, outfit selection — the look and feel of the entire project.
“I sort of represent the label as a creative director — they sort of book you for an album so I’ll sort of oversee the entire album process and that allows me to sort of not be as involved doing photo and video and I can more be involved in the planning and picking the right people to execute sort of a larger project.”
The artist he works with most closely is Thomas Day, a Nashville musician he described as a genuine collaborator — someone with a clear creative vision who communicates it well, which makes the work better and the whole process easier. They also just hang out. That friendship, Robbie said, is part of what makes the working relationship function.
One of the most telling moments in this section: for Thomas’s single “Come Home,” the cover they chose wasn’t a planned shot. It was a BTS photo — Robbie caught Thomas catching his breath after sprinting behind a van, light hitting him at exactly the right angle.
“The shot that we chose for that cover was just like a random BTS photo where I think he was like catching his breath after running behind a van and the lighting just like hit him perfectly.”
The accidents are often the best frames.
The Photographers Robbie Wheeler Looks Up To
The conversation went deep into the photography world Robbie came up in — film, street work, YouTube channels that document the process as much as the output.
Joe Greer came up first and came up often. Robbie has two of his books — Lay of the Land, which he got from a cousin with a damaged copy, and a signed copy of New York City I Love You that Joe handed him directly a few weeks before this recording when Robbie drove down to pick it up. Isaac has the Joe Greer lesson from Moment — three hours of photography knowledge filmed in the Grand Tetons. Neither of them came away with a list of rules. That wasn’t the point.
Willem Verbeek made both their lists unprompted — the kind of photographer so dedicated to the craft that just watching his process on YouTube is worth the time. Samuel Elkins for color and light. Corey Wolfenbarger out of Knoxville, who posts rarely but always lands when he does.
Robbie pushed back a little on being compared to Joe Greer — not defensively, but with a real point. He’d been shooting streets for years before he ever heard the name, and a lot of that early work looked similar simply because that’s what street photography looks like. The comparison is easy from the outside and usually comes from people not deep enough in to see the differences.
“I feel like my work is different enough — especially because how are you gonna copy or imitate someone who’s style is so unique?”
Social Media, the Group Chat, and the Clubhouse Connection
Robbie described his relationship with social media as love/hate, and the love side was specific: not reach or follower counts, but the connections it produced. His biggest clients came through Instagram — not from a post going viral, but from being visibly present and consistent enough that the right people found him.
“I have made a ton of connections through social media that have been super helpful — some of my biggest clients and people who have sort of kept coming back, I met through Instagram.”
He and Isaac are both in the same group chat of creatives, a thread that traces back to Clubhouse during COVID. Robbie stumbled into a photography room one day, got invited to speak on a panel about creative success by Jack Gillespie, and met the group of people who are now some of his closest connections. Jack and Robbie have since hung out in Nashville and New York.
The group chat functions, they both agreed, as a layer of social proof. You encounter someone new in the creative space, check who they’re connected to, and if the right people are already cool with them it changes how you approach the relationship. Community as background verification.
The Independent Contractor Reality
The hardest part of working independently, Robbie said, isn’t the busy stretches — it’s the in-between ones.
“The days that you just don’t have a ton of stuff to do — you sort of have knocked out all your work and you’re sort of waiting for that next event that you have on the calendar.”
His answer to those days: send emails. Not elaborate pitches — just short notes to artists he wants to work with, letting them know he’s available. Sometimes nothing comes back. Sometimes it turns into something like the charlieonnafriday and Tate McRae shows in New York and Nashville, both of which came from a single email to a manager.
“If you don’t reach out there’s zero percent chance that you’re gonna hear from them so you might as well take a risk.”
The longer game is the NYC photo book. After a year and a half of shooting streets during school — thousands of frames — Robbie had about 50 photos he considered book-worthy. He knew he needed more, and that he’d probably need to move back to the city eventually to finish it properly. For now, Nashville is the season he’s in.
“I never wanted to leave New York and I would love to end up there again — but I think for this season it’s been great.”
Isaac made the same kind of connection happen in real life with Josh Horton back in episode 10 — showed up in Ames, met in person for the first time, made a short about it. The through-line is the same: the real moments tend to come from just making contact.
Key Takeaways
- The accidents are often the best frames. The album cover Robbie is proudest of was a BTS photo nobody planned. Shoot everything — you won’t know which frame matters until later.
- Creative direction is mostly planning, not shooting. The visible output is the photo or video, but most of the week is mood boards, emails, and figuring out what the project is trying to say.
- Be consistently present in your creative community. Robbie’s biggest clients didn’t come from viral posts — they came from being genuinely visible and available over time.
- Cold emails fill the gaps. When the calendar goes quiet, send notes to artists you’d like to work with. Zero chance of hearing back if you don’t reach out.
- Shoot in the season you’re in. Nashville wasn’t the plan, the photo book isn’t finished, but Robbie is building toward both by making the most of wherever he is right now.
- Be transparent about your process. On AI edits, on film versus digital — the truth comes out eventually. Being honest about your work upfront costs you nothing.
Follow Robbie on Instagram. Connect with Isaac at isaacjarnagin.com.
