Solo content creation doesn't work for every personality type. Some founders need someone who can push back and keep them on track.

Source: This concept comes from Caleb Ralston's consultation with Taki Moore. Caleb is the content strategist behind Gary Vee and the Hormozis for 16 years.

Casey Neistat could shoot solo. He'd disappear with a camera for hours and come back with finished vlogs. No one needed to tell him when to film, what to say, or when to stop. The creative process happened inside his head, and the output was consistent.

Most founders are not Casey Neistat.

The kinetic entrepreneur, the one with ideas firing in every direction, energy bouncing off the walls, and a dozen half-finished projects at any given moment, needs a different setup. They need a cowboy.

The Cowboy Role Explained

"You are a wild stallion," Caleb told Taki. "Every busy kinetic thinking entrepreneur needs a cowgirl or a cowboy."

The cowboy's job is to corral the energy. Not to suppress it, but to channel it into content that actually gets finished and published. This is someone who can say "we're doing this one" when the founder wants to pivot to a new idea. Someone who can say "this is going out" when the founder wants to trash a perfectly good video. Someone with enough rapport to push back without getting fired.

This role is distinct from a videographer, editor, or even creative director. Those are production roles. The cowboy is a management role: managing the founder's attention and commitment long enough to produce consistent content.

The most important qualification isn't creative skill, though that helps. It's the ability to have direct conversations with someone who probably isn't used to being told no.

Why Casey Neistat Could Shoot Solo (And You Probably Can't)

There's a personality type that can self-direct creative work. They have internal deadlines that feel as real as external ones. They can push through resistance without someone else applying pressure. They finish projects without accountability structures.

If that's you, you don't need a cowboy. Go make content.

But many founders, particularly the high-energy operators building businesses, don't have this trait. Their creativity is externally triggered. They're brilliant in meetings, on calls, in response to problems. Put them in a room alone with a camera and they freeze, or they ramble, or they film something they'll decide to scrap tomorrow.

This isn't a character flaw. It's a personality type, and it requires a different content production setup.

The solo creator model works for Casey Neistat because that's how his brain operates. Copying his process without having his brain produces frustration, inconsistency, and a growing backlog of unfollowed content plans.

Signs You Need a Content Director

You've probably already identified whether this applies to you, but here are the patterns:

You have dozens of video ideas but few published videos. The ideas come fast, but the follow-through gets stuck somewhere between "this would be great" and "this is actually done."

You second-guess content after it's filmed. The video seemed good during recording, but watching it back you're convinced it's not quite right. This isn't quality control; it's perfectionism preventing publication.

Your content output correlates with external deadlines. When there's a launch, an event, or some external forcing function, content gets made. When it's just "we should post more," nothing happens.

You're energized by collaboration, drained by isolation. The best content ideas come out of conversations, not solo brainstorming. Recording alone feels like work; recording with someone feels productive.

Your team tiptoes around feedback. If everyone's afraid to tell you that a video isn't working, you don't have a feedback loop. You need someone who can deliver honest takes without the relationship suffering.

If several of these resonate, solo content creation is probably working against your natural operating mode.

What to Look for in Your Cowboy

The role requires someone with unusual skill combinations.

Rapport with you specifically. They need to understand how you think, what triggers your resistance, and how to navigate your particular brand of stubbornness. This usually means someone who's been around long enough to have seen the patterns.

Willingness to push back. Many people will tell you your content is great. Few will tell you it's not working, or that you're overthinking it, or that you need to just publish the thing. The cowboy has to be willing to disagree.

Creative judgment. They need to know good from bad, not just agree with whatever you say. When they push back, it should be because they have a point, not just because they're contrarian.

Operational ability. The cowboy isn't just a sounding board. They need to actually move content through production. This means coordinating filming, managing editors, maintaining the calendar, and ensuring things get done.

Commitment to the role. This isn't a part-time gig or an occasional consultation. The cowboy needs to be around consistently enough to establish the accountability structure.

Trevor Odum, mentioned by Caleb as an example, filled this role by being someone who could have direct conversations and maintain consistent engagement with the creator. Not just executing tasks, but actively managing the creative process.

Hiring the Role

Some founders luck into this relationship. A team member who was hired for something else turns out to have the rapport and the judgment to take on the cowboy function. That's great if it happens, but you can also hire for it deliberately.

Look for content directors, not just videographers. The skillset is more about creative management than camera operation. Someone can be a brilliant DP and terrible at the interpersonal dynamics this role requires.

Consider hiring the cowboy as employee number one. Before you bring on editors, designers, or other production staff, you need the person who will actually make sure content happens. Everything else is downstream.

Test the push-back dynamic early. In interviews, ask candidates to critique something you've made. See how they handle the conversation. If they're too deferential, they won't be able to do the job when it matters.

Prioritize judgment over credentials. Someone who's worked with high-profile creators and knows what good looks like will likely outperform someone with an impressive resume but no feel for the dynamics involved.

The right cowboy pays for themselves quickly. The wrong one, or no one at all, means another year of inconsistent content and mounting frustration about a channel that could be working but isn't.