Joe Dorsey, Founder of Checkbox Media: Somewhere Out There and Real Travel Storytelling

I submitted because I truly believed in the work. It took a different approach—using real client travel photography, no stock, and bringing it to life with AI in a way that preserved authenticity. Winning is both rewarding and validating, and it’s meaningful to see that the industry recognizes and appreciates that direction.

“Somewhere Out There” is built entirely from real trips planned by Jess.Travel—no stock footage, no influencers, and no fabricated locations. AI was used as a post-production tool to introduce motion and depth, while preserving the authenticity of the original photography.

The intent was to show that a travel brand can be visually compelling without compromising honesty, and that authenticity itself can be a powerful creative direction.

Authenticity was the core of the piece. Most travel content relies on stock footage or polished influencer clips that feel disconnected from the actual experience. This video takes a different approach—while it appears cinematic through AI-driven motion, every frame comes from real places visited by real Jess.Travel clients. That combination is rare.

The biggest challenge was getting the AI animation to feel subtle rather than gimmicky. There’s a fine line between motion that enhances the atmosphere and motion that draws attention to itself. It took several iterations to reach a point where the movement felt natural—subtle enough that you might need to watch it twice to realize the images aren’t video.

I’m looking forward to having more conversations with travel brands that want something beyond generic content. There’s a real opportunity for video that is both credible and visually compelling, and this work shows that Checkbox can deliver that. It also helps Jess. Travel stand out in a crowded space where many agencies look the same online.

My wife, Jess, has been very pleased with the result, which means a great deal. Viewers tend to pause and engage with the piece, which was exactly the intention. We’ve also received inquiries from other travel professionals interested in how it was produced.

Start with a genuine idea. Instead of aiming to create something “award-worthy,” focus on making something truthful. When the concept is strong and the execution is honest, the work naturally holds up under scrutiny.

It’s also important to consider niche categories. While “Video – Travel” is competitive, its specificity can be a strategic advantage compared to broader, more saturated fields.

AI is a tool, not a replacement for judgment. The best work in the coming years will come from those who know when to use it and when to leave it aside. Clients are becoming more adept at recognizing the difference between thoughtful use of AI and work that relies on it too heavily.

If you’ve created something you’re proud of, submit it. The worst outcome is that you gain insight into how your work is perceived. The best outcome is that you win and have something meaningful to point to. Either way, the experience is worthwhile.

Stop chasing what worked for someone else. The work that stands out is usually the work that didn’t follow a template.

Jess. She built the travel business from the ground up, and every image in the video exists because of the experiences she creates for her clients. I simply brought those moments to life.

Real photos from real trips, brought to life through AI—demonstrating that a travel brand can be cinematic without sacrificing authenticity.

We’re currently developing additional branded content for Jess.Travel, including a full commercial. On the Checkbox side, we’re also expanding our work with corporate clients into the podcast space.