If you’ve worked in any facet of marketing over the last 15 years, you’re probably familiar with Gary Vaynerchuk’s robust content engine which produces 80-100 pieces of content per day.

This content machine is fueled by hardworking creators behind the scenes like Caleb Ralston. Caleb is a videographer from Washington whose passion for the creator economy and constant determination led him to a career with some of the biggest creators in business.

We sat down with Caleb on the Backstage Careers podcast to discuss his time working with Gary and his current role as the creative director for entrepreneurs Alex and Leila Hormozi. You’ll find the key takeaways from the podcast interview with Caleb below including how the GaryVee team produces so much content, how he’s taking the Hormozis to the next level, and his career advice for any eager videographers looking to work with major content creators.

Check out the full episode with all of Caleb’s experiences and takeaways on YouTube, or listen on Spotify or Apple Podcasts.

How being persistent landed him his big break

I read Gary's book Crush It when I was 15. Later in life, I was providing freelance video services and one of my best friends sent me Gary’s Instagram story saying they were looking for videographers.

I grabbed my phone and recorded a video on the spot to send to David Rock (Gary’s Executive Creative Director, known more commonly as DRock). I followed up probably 24 hours later with another video and then another one. I kept following up.

The way I went about it was very intentional and I've always kind of been this way.

In my first email to David, my opening line was, “this is definitely not my only time contacting you. I live, breathe, eat, and (no) sleep video. I'd love to learn how I can add value to the amazing VaynerMedia team.”

I made a page on my website (CalebRalston.com/DRock) where I had an opening video that was vertical, filmed on my phone. I laid out videos that I was proud of and could use as reference for my skill set. Then I put three references that I felt were applicable—one of my direct reports, my mentor who also was very heavy in the YouTube space, and my buddy who was a very prominent Instagram influencer.

Then I kept following up. There would be times where I would send an email and I wouldn't hear back. So, I would send a follow-up email with videos of me in my apartment tying my shoes while talking, or in my car driving and talking—basically mini vlogs.

My thought was, there's millions of better videographers than me. But I think I'm good at making people feel comfortable on camera filming because I have a fun personality to work with. And if I really believe that, I should show them that as a distinguishing factor.

I got the job two weeks later with PureWow (a Vayner company).

I was hired as a videographer/content creator. I viewed it as an amazing opportunity to work directly with the CEO and do something that he finds very valuable. I did everything I could to push myself really hard. I also really tried to get to know as many people in the company.

About once a month I would meet with David and just check in, give him updates, and ask for advice. Then about nine months in, I got a message from David saying that he and Andy Kak, the previous head of Team Gary, wanted to pull me onto their team.

Gary is always maximizing his time. If we were in transit and he's not on a call in the car, then he's responding to comments, reading Twitter, looking at the millions of texts, prioritizing things with our team. There's very little downtime. 

But the advantage I had coming into it was that I had been consuming Gary's content for nearly eight years before I started working with him. I had so much context and so many questions. Plus I'm very observant of little tweaks in somebody's body language when I'm filming them. I could see that he's writing a tweet and as soon as he finished, I had my moment. There's a millisecond where if I ask him a question, I'm gonna get his attention. So, I would wait for it and I had my questions ready. I tried to take advantage of any of those moments. 

When I was on the team, if you were a traveling videographer, you were doing more than just filming. It’s not required. He never asked. But the way I viewed it was taking on whatever I see as an inconvenience for him. If we were walking through the airport, I'd offer to roll his suitcase while I'm filming him. I'd be coordinating with his executive assistants as the boots on the ground to keep them updated on whether or not we were keeping to his calendar.

Initially, I was figuring out that cadence and trying to observe different areas where I could help in addition to filming. I have always believed that you have your core role, but if you're able to fill in extra areas, that’s a differentiator and a great way to stand out.

Lessons from Gary

Gary is an even better dude than you see in the content. There's a lot of cool stuff he does that he doesn't put out because he's not trying to brag, and that was a great confirmation that doing the right thing is crucial.

I learned from him to put the audience first when creating content and asking, “does this provide value to the audience?” If not, it's not really worth putting out. Really pay attention to what people are saying in general and take that to heart.

Plus the amount of times that I witnessed Gary in meetings with big brands coming up with some wild ideas on the fly is unreal. Before Team Gary, I would get flustered and angry if a manager would ask me to come up with ideas on the spot without time to prepare. After working with Gary, I actually now feel like those are some of my best ideas.

One tip from Gary that might be helpful for anyone looking to work with a creator is to map toward what they prefer or what you’re best at. Reverse engineer what you’re best at and build around that. Find out what they love to do or what they hate doing and build a system around that.

Pivoting to creative director for the Hormozis

Alex and Leila had been creating content that really was blowing up. They wanted to take it to the next level and hire a videographer. They're really good at taking high level concepts and making them understandable for an uneducated individual, like myself.

I wasn’t necessarily looking to take on another videographer position, I was looking to expand. So, thanks to mutual friends connecting us, they brought me on as the Creative Director to kind of go about building a media monster.

In the traditional sense, my role sets the tone for the creative and basically oversees it all from copy to visuals and everything in between. But I'm also looking at it too from the standpoint of long-term strategy. I'm not an expert strategist. I'm not ever gonna pretend that. But I think I have enough information and intuitive thinking to be dangerous and to work with other platform-specific strategy experts.

The goal is to build a team of creatives and strategists to help Alex and Leila to fulfill their mission of documenting world-class businesses.

I also love using my skill in creating content, specifically within video, to benefit peoples’ lives.

For example, Alex uses Twitter as an idea tester. If he has a thought, he puts it out as a tweet and gets immediate feedback on it. Leila's version of that is Instagram Stories. If you follow her closely, you'll notice that once or twice a week she’ll post a few tiles that are a little write-up. It's usually whatever she's feeling or whatever she's noticing.

I get excited talking about all of this because it's like basically just taking an orange and trying to get as much as you can out of it. It's something I very much got from Gary: How do we take this one thing and turn it into as many different things as possible?

Caleb’s advice for working with creators

To anyone looking to work with a creator, I would first figure out why you want to work for them. Are you trying to hone certain skills or are you trying to work for the person that you want to eventually be?

In my opinion, that determines the approach that you take in a world with minimal skills or previous experience.

If I was really early on, I would do what I call the ladder method. I would look at who do I want to be or who do I want to work for? Once you’ve found who you want to work for, identify the people that are a few rungs down the ladder. People that you’ll have an easier time accessing and showing you exist.

That's literally what I did. 

I decided in high school that I wanted to work in video. I was very passionate about the power lifting and bodybuilding space. My dad was a bodybuilder and I filmed a video with him, then I used that as an example to get work with the biggest name bodybuilder in Washington. Then I used that to work with a pretty prominent nationwide bodybuilder. At that point I had built a portfolio of enough work and had built a reputation that I could hit up very prominent individuals in that industry and work with them.

Lastly, start small. Don't get me wrong, I'm also down for reaching for the stars. But do both. Take things step by step and have big aspirations.

It's so cliche, but there’s that saying of, “luck is when opportunity meets preparation.” I genuinely believe in that. Don't shoot your shot too early with the person that you want to work for. Build up your skills and prepare in order to have a good chance when it’s time to shoot your big shot. That’s how I would go about it—aka it's what I did.

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Backstage Careers is a podcast that shines a light on the linchpins working behind the scenes with some of the biggest entrepreneurs and creators. Led by YouTube expert Jeremy Mary, it has featured the influential team members behind pro creators and entrepreneurs such as Airrack, GaryVee, MrBeast, Tim Ferriss, and more.