Your shoulders can feel heavy as a content entrepreneur.

After all, according to The Tilt’s research, the average time between launching a content business and making your first hire is almost 19 months. In that time, you are responsible for all the tasks necessary to create a successful operation.

But when you can (or are willing) to expand your ranks, what do you hire someone to do?

“Entrepreneurs are visionary thinkers, so they need to hire implementers,” says Kate Ertmann, founder of Kate Loves Math. “Even if you are a good implementer yourself and you gain some personal satisfaction since you’re really, really good at whatever that task may be, you’re going to become an efficiency bottleneck. In math, the word ‘bottleneck’ is used interchangeably with the word restriction in the world of optimization problems.” 

Kate’s first hire? A project manager. “Though I had had my own positive experiences being a project manager before I had my own business, I knew that an entrepreneur’s first few hires should take some weight off themselves,” she explains.

Cat Margulis​, host of the Passion Project podcast, author, and book coach, has taken a long time to hire someone because, as she admits, she’s “a bit of a control freak.” 

She’s in the process of hiring an assistant editor and project manager so she can serve more people. “I’m clear my zone of genius is in coaching on storytelling and consulting on content strategy,” Cat says.

Bestselling author and speaker Andrew Davis says his first hire was a full-time logistics and operations role. He needed them to handle the massive amount of travel, invoicing, and interactions required to run a successful speaking business.

​Rachel Smith​, founder of Rachel’s English, says she needed an all-around admin support role, though she found the first person she hired wasn’t a good fit and let them go.

Virtual assistants are a popular choice for a content entrepreneur’s first hire partly because job descriptions can vary widely.

Justin Moore​, founder of Creator Wizard, hired a virtual assistant to help curate his newsletter, saving him four to five hours a week. “I now try to spend as much of my time writing and recording videos, which are my areas of strength,” he says.

A virtual assistant was also the first hire for Austin L. Church​, author and founder of Freelance Cake. “Many pieces of a consulting or business coaching engagement are difficult to delegate, especially if the other person doesn’t have domain expertise,” he explains. “Buying back my time by delegating high-frequency, low-leverage tasks, such as inbox management, calendar management, and weekly newsletter setup, has enabled me to spend more time in my zone of genius and drive revenue.”

Christopher Mitchell​, founder of travelingmitch, went in the opposite direction and brought on a business partner. “I couldn’t imagine how much easier (and better) things got when I was no longer just working through things on my own,” he says.

While Michelle Martello​, founder of Minima Designs, doesn’t have a team now, she has hired assistants and junior programmers over the years. But she wouldn’t have made the same choice if she had been hiring today. 

“I would leverage AI for most of the same tasks. Instead, I would spend more on hiring expert accounting and advertising consultants who specialize in selling digital products,” Michelle says.

No matter what role you hire for, Kate says, you should take the time to hire people who have complementary strengths and characteristics different from your own. 

“You want your team to be in harmony as opposed to being in sync,” she says. “A mathematical requirement of a harmonic team is that each person’s contribution will reflect what makes them unique. Alternatively, if you build a team that’s all in sync, you’ll likely feel good in the short term … but long-term synchronization in a business does not equate to sustainability. 

“The only way to survive external change is to intentionally build flexibility within – and there’s no room for flexibility in synchronization.”

Helpful Resources:

Learn from expert presenters at Content Entrepreneur Expo (May 5-7, 2024).  Registration is now open!

About the author

Ann regularly combines words and strategy for B2B, B2C, and nonprofits, continuing to live up to her high school nickname, Editor Ann. An IABC Communicator of the Year and founder of G Force Communication, Ann coaches and trains professionals in all things content. Connect with her on LinkedIn and Twitter.