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Nathan Barry

3 problems creators face when scaling up a team

Published 4 months ago • 3 min read

Hey Reader,

At some point in the growth of your creator business, you come up against the upper limits of what you’re able to accomplish on your own.

This is when many people hire a team.

While the first few employees free you up, as the team grows, so does the demand on your time. What a lot of creators find is things start to quickly spiral out of control.

Matt D’Avella shared his experience with this in a recent video:

video preview

What started as a love for his craft turned into managing people, responding to emails, getting on dozens of calls per week, and a crippling stress that manifested as a tightness in his chest.

His life went from doing things he “wanted to do” to things he “had to do”.

Work was no longer fun, it was a dread.

Yet some creators are able to scale up a team just fine and have it work well for them. Ali Abdaal is one such example featured in a short segment of Matt’s video.

But even Ali explains that process was difficult for him:

“For me, scaling the business has been worth it. But I have not enjoyed the process of hiring and managing employees. The place I’ve gotten to now is I don’t actually manage anyone [other than my general manager].”

I see creators face three common problems when scaling up a team (continued after the break):


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1. You hate managing a team

The motivation for hiring a team is so that you can do more of what you love. But what often ends up happening is you become a manager.

The time you spent creating now goes toward people management, emails, and meetings. Your job changes entirely.

Your new job doesn’t excite you and sucks the joy out of your work. You start to miss doing things solo, but now you have the massive burden of feeling responsible for people you care about and their livelihoods.

Either you need to actually love managing people or, like Ali, aim to make it to a point where you have someone who manages people for you. Be aware that the journey to that point can be difficult and exhausting.

2. Revenue doesn’t stick around

This is a really difficult one. You encounter some success, things are growing, and you build a team on the assumption things will continue to go well.

But then the market shifts, lead sources dry up, and platforms change their algorithms.

You’ve spent money, and hired people, assuming the revenue would keep coming in, but old sources have dried up.

What would you do if you had to reinvent your business? Or pivot to new ways of generating revenue? The more diversified your income sources, the better your position to weather any fluctuations.

3. The business gets too complex

When you’re doing things solo, you can make changes and adapt quickly to find what works. But what works at a small scale doesn’t necessarily work at a larger scale.

A small airplane doesn’t take much energy to stay off the ground. But the bigger the plane, the more complex the systems needed to keep it in the air.

With a big team, it’s not just that you have to spend more money. You may find that your plane just doesn’t naturally fly anymore.

Look for examples of your model working at a bigger scale.


If this topic sounds interesting to you, check out the podcast conversation I had with Grant Baldwin and Bryan Harris below:


video preview

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What is the biggest struggle you face with scaling up a team?

Hit reply and let me know!

—Nathan

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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