Dylan Van Leuven was a full-time freelance videographer based in Oskaloosa, Iowa, doing work for Kelderman Manufacturing and real estate clients across Southern Iowa. Isaac had gotten to know Dylan through Johnny Jarnagin, who had been collaborating with Dylan for a while, and the episode covered how a high school video class turned into a full-time career, what it was like to film Aaron Lewis riding motorcycles through the South Dakota mountains, and why real estate work made Dylan a better editor.
Kelderman and the Aaron Lewis Truck Build
Kelderman Manufacturing is an Oskaloosa-based truck modification shop — known primarily for the air ride systems they install that let trucks lower at the push of a button, but also doing custom bumpers, monster hooks, and farm equipment. When Dylan came on board about three years before the episode, he was doing youth sports and small local videos. Kelderman took a chance.
The content operation had grown since then. Dylan shot and edited everything — Instagram reels, TikTok, long-form YouTube walkaround videos where owner Jeff would walk through a build and explain what they’d done. He’d also helped bring on a marketing person to handle posting, which freed him to stay focused on the creative side.
“I kind of just want to stay in my lane — just create videos. Now my role is more so just create the videos, do what I want to do, and then send it off.”
The most memorable shoot came through an Aaron Lewis truck build. Lewis, the lead singer of Staind and now a solo country artist, had spent years tracking down a pristine vintage square body truck, put somewhere between $200,000 and $300,000 into restoring it, then brought it to Kelderman for air ride. Dylan went to Nashville with Jeff to pick it up, attended a VIP event, and met Lewis on his tour bus. Months later, Jeff’s South Dakota cabin near Mount Rushmore happened to overlap with a Lewis concert nearby. Dylan spent the week riding side-by-sides through the mountains, got to drive Jeff’s Hellcat on his own, and filmed Lewis and others on motorcycles through the hills while hanging out the side of the car.
“If you’d have told me a year ago I’d be out here… this was such a beautiful day in the spring hanging outside of the Hellcat taking video of this artist.”
The Kelderman relationship had given Dylan something to build everything else around — consistent enough to go full-time, flexible enough to leave room for other work.
How Dylan Van Leuven Got Started
Dylan’s path into video started with a high school video production class he joined because a friend told him it was an easy A. He stayed because he actually liked it — specifically, that he liked editing more than shooting. He spent free periods and time after school at the computers, pulling clips of his favorite sports teams from YouTube and cutting them together just to see what he could make.
“I’d hated using cameras — I hated shooting stuff. But I loved editing.”
Senior year, after his football season ended, some teammates asked if someone could throw together a quick highlight reel. Dylan said sure. Two months and hundreds of hours later he had an hour-and-twenty-minute film — interviews with seniors and coaches, every game, the whole season documented in a way nobody had done for that school before. The group chat still had the link. Years later he still got messages from guys who’d sat back down and watched it through.
He went to William Penn University in Oskaloosa for a year and a half, studying video. But what he’d built on his own was already ahead of what was being taught. When Kelderman started asking him to shoot for them while he was still in school, he had his reason to leave.
“I was kind of finding a reason to leave college — I was like, sure, I’m just going to go all in on this.”
He’d also been playing football his whole life. After William Penn he played briefly on arena football teams in Kansas and Michigan before settling into a semi-pro team in Newton, Iowa — once-a-week practice, mid-twenties to middle-age guys showing up purely because they still loved the game.
Real Estate, Weddings, and Pricing Up
Alongside Kelderman, Dylan had started doing real estate video work — mostly farmland and hunting properties that were primarily drone footage, plus a growing number of houses, which were more interesting to edit. The work was steady, paid well, and had an unexpected benefit.
“Real estate is kind of fun in a way — it’s not as exciting of a video to edit, there’s nothing flashy about it. But it is a simpler edit and it also pays pretty well.”
What real estate did for his craft was sharpen composition. The shots had to be thought through. Transitions had to vary or the whole video felt repetitive. Nothing flashy — no lightning bolt effects, no hard cuts for hype’s sake. That discipline carried over to everything else: go back to a sports edit and suddenly you’re second-guessing every effect that doesn’t need to be there. Brian Pollari had talked about building a whole media company around real estate video for the same reasons — consistent demand, clean work that builds real editing instincts.
Wedding work was a different calculation. Dylan was good at it — a recent wedding he’d shot with Johnny Jarnagin was some of the best work he’d done — but the mental load was real. Five days of anticipation, days of processing after. The strategy going forward was simple: fewer weddings, higher prices.
“I’d love to be able to just jack my prices up and do like five weddings for like $5,000 — rather than being stuck doing ten or twenty at like $1,000 or $2,000.”
The Creative vs. Business Tension
The question that surfaced mid-episode was whether Dylan saw himself as more of a creative or a businessman. He leaned creative, but admitted he’d been feeling the drift.
“I see more creativity in my older stuff when I was doing it more so like for fun. Whereas now I’m doing everything for work and it’s kind of almost like a machine trying to just knock out videos.”
Sitting with Johnny watching old footage had made that clear. The early work was rougher, but it had something. He wanted to get that back — and recognized that handing off posting to a marketing person had been part of the same instinct. Not a business move first. A move to protect the part of the work that actually mattered.
Small-Town Iowa, Gear, and What’s Next
One of the threads running through the episode was the small-town market angle. Oskaloosa has about 12,000 people, and Dylan’s view was that smaller markets were more opportunity than limitation for anyone actually willing to show up consistently.
“I think people are always afraid to be in a smaller area just because of the lack of opportunities — and I’m like no, you can take that area over easily.”
Iowa more broadly had more going on than most people realized. More talented creatives were coming up — including Reed, a high school photographer in Oskaloosa who’d helped on a wedding shoot and surprised Dylan with how good he was. And on the demand side, there were plenty of companies across the state that needed consistent media and didn’t have anyone in-house to produce it.
On gear, Dylan had been running the Sony a7 III and was happy with it. The next move was a 10-bit system — likely the A7S3 — for better color work as the real estate side grew. The bigger shift lately had been around lighting. A friend deep into Aputure equipment had reframed how Dylan thought about it: start by making the room completely dark, then build the light from scratch.
“More than ever I’ve just kind of — it’s been nice not having to think about gear at all. I have the stuff where I can shoot decent stuff.”
The longer goal was a studio, multiple ongoing clients, and other people helping with shoots and edits. The infrastructure was starting to come together. Three years with Kelderman, consistent real estate work, weddings on his own terms. He’d gotten there the same way he’d gotten everything else — by showing up before he was ready, and not stopping.
“I could say I’m better now but I definitely wasn’t the best when I started out — it’s just because I showed up. Availability is the best ability.”
Key Takeaways
- Showing up beats skill level early on. Dylan got and kept the Kelderman gig before he was at his best — showing up every week built the trust that made it last.
- Small markets are easier to own than they look. A town of 12,000 is a real opportunity for someone willing to take it seriously and build consistently.
- Real estate video sharpens your craft. The composition and seamless transitions required for property work carry over to everything else you shoot.
- Stay in your creative lane. Handing off posting freed Dylan to focus on the part of the job that actually mattered — and the work got better for it.
- Price weddings to protect your energy. Fewer high-priced weddings beats a full calendar of budget jobs — the mental cost is the same either way.
- Lighting is its own discipline. Building light from a dark room produces results that pointing a key light at your subject never will.
Follow Dylan on Instagram. Connect with Isaac at isaacjarnagin.com.
