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Each week, I reflect on lessons learned growing my Personal Holding Company — the good, the ugly, and everything in-between in raw, unfiltered, free-form writing.

When You Should Hire an Operator

Last week, I posted about the time when one of my operators at my Personal Holding Company turned on me:

The biggest pain point in a Personal Holding Company is knowing when, where, and how to hire an operator to run your business.

Today, I’ll cover when you should hire an operator.

Let’s dig in…

Art, Not Science

This is an art, not a science.

There isn’t a perfect time.

It’s a balance of intuition, your interest, your own time, your company’s finances, among many other variables.

However, it is important to start thinking about hiring an operator as soon as possible so you can shape your company to run without you.

When you start a business, you should always be the operator. If you acquire a new business, you should quickly ramp up your knowledge to be the operator.

Why is this so important?

It’s your new baby and it needs to survive.

You should know the business inside out in case something happens and you need to step in.

After you survive the early stages, you can start identifying what you’re looking for in an operator.

This process is important because if you bring in an operator too early, they may not have the skill sets you need.

For example, the operator for my company UrbanEDC.com was plugged into the everyday carry community with strong relationships with makers and vendors. This was a huge boost for us as we grew over the past 2-3 years. I wouldn’t have known how important this position was until I understood the market.

It’s critical to understand that who you bring in at the early stage may not be who you need at a later stage.

In other words, you may need to re-evaluate the market and see if the needs of your business to grow to the next level needs a different type of operator.

Companies do this frequently, replacing CEOs when they feel the company has outgrown the skillsets of a particular CEO.

You, as the business owner, should be aware of changing market conditions and respond accordingly.

The best operators will adapt to the changing market and learn the skills to grow into the next phases of the company. But these operators are A-Level operators and difficult to find.

If you do find them, make sure you have an attractive compensation plan for them. Trust me, it’s worth it!

Hope this was helpful!

See you next week. ✌🏼

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