So You Want To Hire An Operator?

So, you want to hire an operator for your business?


A good operator is the key to unlocking a lot of things in your business:

  • stability
  • new growth
  • happy customers

But most importantly…

An operator is the key to allowing you, as founder, to step back and chill out.

You know, all those other things that life has to offer?


It’s really hard to properly enjoy a 1981 Kopke Colheita on a warm summer evening when you’re worrying about a Zapier integration misfiring.

(Makes it tough to appreciate those gorgeous caramel-toffee tones.)

So we’re agreed…

Operator = good.

But you’ll need a A-Player, right?


Not so much.

What’s Wrong With Rockstars?


If my teaser from the intro did its job, you will have done a double-take.

Surely you need an A-Player to operate your precious business?

Well, in today’s newsletter, I’m going to argue that… no, you don’t.

In fact, searching for the proverbial “Rockstar” can cause you far more trouble than they’re worth.

Here’s the punchline:

Rather than looking for an experienced operator, I advocate hiring from within your audience.

And I’m going to spend the rest of the newsletter explaining why.

Here’s what I’ll assume about your business:

  • Founder-led online business
  • 6-7 figures in annual revenue
  • Have an audience & email list
  • You run the show (plus a handful of staff)

Hiring For The Right DNA

Conventional hiring wisdom says that you should find an experienced person who has successfully done this exact role many times before.

This is the proverbial “A-Player”.

Problem is, this kind of advice lacks context.

Sure, if you’re a public company with $100m divisions to run, or a high-growth startup spending other people’s money… then you probably should look for A-Players all day long.

Trouble is, you’re not running that kind of business, are you?

You’re running an online education business you’ve built from the ground up.

You help people.

You give a s***.

Your business is tied up in your identity.

For you, business is as much about living the good life as it is about your bank balance.

And you wouldn’t sacrifice ANY of the autonomy you enjoy for a few extra 000s on the bottom line.

This, my friend, is called “relevant context”!

So, what does this context tell you about hiring an operator?

It tells you that with any individual hire, there’s a higher-order priority you’re optimising for, which is:

“How do I maintain the business <> lifestyle equation that I’ve worked so hard to build?”

(Again, context matters.)

A-Players vs Audience Hires

OK, so why might an A-Player be the wrong hire?

With A-Players, you need to be aware what you’re getting into.

Real A-Players…

  • Aren’t applying for jobs, they’re headhunted. This makes them hard to find.
  • Aren’t interested in your business. They want high-status startups that come with equity incentives.
  • Anchor against tech salaries. You can’t afford that.
  • Are careerists. They’ll stay with you for 1-2 years before moving on to the next thing. (Ask any tech founder about this.)

For many online entrepreneurs or personal brands, injecting this kind of energy into your business can cause more harm than good.

“But if they grow your business, why wouldn’t you hire them?”

I’ll tell you why not…

Because there’s a better alternative.

Hiring from within your audience.

Hiring from you audience creates an entirely different dynamic that (I believe) allows for better, more sustainable, more aligned growth over the long-run.

Hiring A-Players is like taking those green powder supplements you hear about on a Tim Ferriss podcast ad…

Yeah, they’re probably good…

But you could just eat vegetables instead.

Sure, they take a while to prep, but which is the habit you’d rather take into your old age?

6 Reasons to Hire From Your Audience

Here’s why I like to hire from within my audience, and why I recommend you should turn to your audience to find your operator.

1. Familiarity with your brand

People in your audience understand you and your business.

If they are customers, they also understand how your products work from firsthand experience.

An operator with this knowledge will be able to represent your business faithfully at every touch point. This includes customers, but also includes team leadership.

Don’t underestimate the power of this, especially if you care about what you stand for.

2. Long-term hire

Someone from your audience who has the opportunity to work with you is doing it for the right reasons.

It’s not just another gig…

It’s probably the opportunity of a lifetime.

If you’re offering flexible remote work, this is even more the case. In my experience, these people end up, loving their work and can’t imagine quitting in a million years.

The value of long-term staff to your business is immense, and brings you huge stability on a personal level too.

Compare this to an A-Player who parachutes in for 18 months and then leaves again, I would take the long-term hire any day.

3. Your business ain’t that complicated

I know you’ve been told you need an exceptional talent with deep knowledge of online business… But do you really?

Most online businesses aren’t that complicated. If you need an operator, chances are what you really need is someone with a very systematic brain to come and bring order to the chaos.

There are plenty of highly organised, highly capable people who can do this.

You probably don’t need someone with a PhD from Facebook to run your online business.

In fact, a certain amount of inexperience isn’t necessarily a bad thing.

It can be far better to have a person with strong aptitude who can figure out the systems that work for you.

4.Pace of evolution

Businesses like ours tend to evolve slowly over time. It’s not a cutthroat, fast paced, start-up environment.

Developments can happen over years… Not months.

As such, an experienced A-Player who wants to be challenged and plans to be out the door in 18 months is like a sledgehammer for a nail – simply the wrong tool for the job.

Better to have someone who can grow and learn with the business over time

5. Cost base

One of the biggest mistakes that growing businesses make is to increase their cost base too quickly.

Given the role of time in the growth equation (as per the last point), it makes all the sense in the world to hire people on moderate salaries, who can keep the business on stable footing.

This also reduces the pressure on you to try and demonstrate a clear ROI.

6. Cultural fit

Even big corporations talk about cultural fit.

But in small businesses like ours, cultural fit is everything. The people who work on the business with you are like family.

A-Players can be extremely disruptive to your team culture, because of mismatched expectations, along with all the other points in this list.

This is probably something you have to experience in order to understand, but I’ll leave it here as food for thought!

How to hire from your audience

I won’t go into my full hiring process here, other than to make one very important point.

There is one thing above all you are looking for when hiring for any role…

But especially for a management role…


Skills and processes can be trained.

But aptitude is the character trait that governs whether they will go out and learn that stuff of their own volition.

I’m always skeptical of people who talk a good game.

More often than not, it’s hot air.

Aptitude rules supreme, and that’s why my hiring process always involves a practical task (given at the last minute with minimal time for prep), along with a 3-month “paid trial” period.

Basically, I want them to demonstrate they’re the right person… not tell me. (That’s the big weakness with the traditional interview process.)

Over 10 years of running, all my best hires have come from within my audience.

(It’s one of the invisible benefits of growing an audience online.)

I’ve always looked for aptitude above all.

In fact, my COO has been with StoryLearning for 8+ years, having initially bought one of my courses back in 2014.

He started off making PDFs for me… for free.

He ended up running the entire business.

In fact, we’ve grown the business together, and he understands it better than anyone else.

He’s also a great friend and I was at his wedding in Buenos Aires.

Now, call me old-fashioned…

But that’s the way I like business to be.

This is how to play the game at A-Level.

Because when you eventually learn the devastating truth about money… all you’re left with is the quality of the people around you.


To hire an operator for your business, you don’t need an A-Player.

You need an exceptionally organised “systems thinker” with high aptitude for learning new things.

There are many such people in this world.

And you almost certainly have a bunch of them on your list already.

The magic of sourcing such a person from your list is that they will come with a love for your brand, the desire to make you proud, and stick around for long enough to grow with your business for years.

That’s been my experience anyway.

Not saying it’s the only way to do things…

But at least you’ve now heard a contextualised take on the topic!

Until next time.



CASE STUDY: Blueprint Of A $10m Online Education Business:

  • Business model blueprint
  • Product ecosystem
  • Team structure
  • Evergreen sales strategy
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