Only about a decade ago, Jackson Wigger (@jacksonsvisuals) was filming stop-motion Lego movies on a VHS camera and editing them in Windows Movie Maker. Now he’s flying hundreds of times a year shooting video projects for the Super Bowl, Coachella, Lyrical Lemonade, major music festivals, touring artists, and some of the biggest entertainment brands in the world. On this episode of the Eleven Percent Podcast, Jackson broke down the full story behind how he built his career, what the reality of the freelance creator lifestyle actually looks like, and why most creatives still aren’t hungry enough to succeed.
One of the most interesting parts of Jackson’s story is how unplanned a lot of it actually was. He started by making short films with friends, filming dirt biking videos, trampoline edits, and random summer compilations during high school. Instead of obsessing over views or trying to “go viral,” he focused on making videos constantly and improving every single week. During COVID, he said he was filming literally everything with his friends just to get repetitions in, color grading, editing, camera movement, pacing, storytelling. That consistency eventually led him into the Chicago hip-hop scene where he began dm-ing smaller artists and offering to shoot free recap videos just to get experience and network. That free work eventually snowballed into working with Lyrical Lemonade and eventually catching the attention of Cole Bennett himself after Jackson made an overnight recap video for Summer Smash 2019.
The craziest part is how many of the opportunities came from simply overdelivering. Jackson explained that after filming Summer Smash as basically just a kid with a camera, he stayed up overnight editing the recap immediately while everyone else was sleeping. Cole Bennett ended up seeing the edit, texting him directly, and asking him to work on official recap content. From there, bigger opportunities started stacking fast. Eventually he was working festivals like Lollapalooza, directing music videos, and filming massive live events. But one thing he kept emphasizing throughout the conversation was that none of this happened because he waited until he was “ready.” Most of the time he felt completely underqualified. Even now, after shooting five Super Bowls, he still sometimes questions how he ended up in those rooms. His mindset is basically: if you got invited into the room, there’s probably a reason for it.
We also talked a lot about the less glamorous side of the creator industry that people usually don’t post online. Jackson said the nonstop travel sounds cool on paper — private jets, backstage access, luxury dinners, but most people never see the exhaustion behind it. He talked about sleeping four hours a night during tour runs, waking up confused in hotel rooms because he forgot what city he was even in, and having to instantly switch between “high-pressure production mode” and normal life back at home. One of the wildest stories was him directing a The Chainsmokers music video where an entire town lost power mid-shoot, restaurants shut down, their boat rental got canceled, and the whole production nearly collapsed in real time. Hearing stories like that honestly reminds you how much freelance production work is really just problem-solving under pressure.
Probably the biggest takeaway from the whole conversation was Jackson’s mindset around hunger and consistency. He said most creatives get comfortable too fast. They post a few videos, try outreach for a month, don’t instantly blow up, and stop. Meanwhile the people who actually make it are usually the ones filming every day, editing every day, studying references every day, and continuously putting themselves into uncomfortable situations. He talked about setting unrealistic goals on purpose because even missing those goals usually still pushes you way farther than playing safe ever would. That mentality is honestly what separates a hobbyist from someone who actually builds a career in this industry.
🎥 Watch the full podcast episode here:
Watch on YouTube
🚀 Edit event recap videos 10x faster with AI:
AutoEdit Event Recap Mode