June 24, 2023
Read time: 3 minutes

Most of us understand the importance of delegation.

We know that to reach the next frontier—in our career, business, family, etc—we need other people.

The most difficult part is finding the right people.

This is especially true for business owners looking to hire full-time operators.

In today’s issue, I’ll break down my process for finding talented leaders:

If you were forwarded this email, click the link below to join 3,200+ others receiving one actionable tip every Saturday to buy cash flow, build passive income, and diversify their net worth.

Defining “Operator”

For our purpose today, the Operator is the day-to-day, hands-on leader of the business.

General Manager, CEO, or Division Head—call it what you will.

As the owner, you hire this person to manage and grow your business.

Their economic interests are directly tied to the business’s success.

In return, you give them the power they need to make decisions and effectuate change.

Characteristics of an A+ Operator

The ideal candidate will be different for every business.

However, there are some common attributes to look for:

  • Equity Incented: the person has a high-impact role in their organization, but little to no equity or profit share. They crave more upside and embrace a higher level of accountability.
  • Risk Averse: the person is equally—or better yet, more—capable to run the business than you. However, their natural risk aversion prevents them from starting something on their own.
  • Driven: the person is highly motivated to be the #1 player in the business. They take pride in their craft. They want the pressure that comes with the lead role and are energized by the opportunity to build a team and define the culture.

When I’m looking for an Operator, these three items are non-negotiable.

I will not compromise on any of them.

By contrast, there are some common factors I’m willing to look past:

  • Limited Experience: Experience matters. But not as much as people think. A smart, driven, capable person can ramp up on most simple businesses quickly.
  • Age: I don’t need someone with grey hair. I have enough of it (I know it’s difficult to see in my headshot, but just ask my wife).

In short:

Hire the 27-year-old with something to prove rather than the complacent 55-year-old with 30 years of work experience.

How to Find A+ Operators

It’s true what they say:

A single A-player is worth ten B-players.

Here’s how you can find A-level talent (in order of effectiveness):

1. Your Network

There is significant value in hiring someone you already trust and respect.

I have mixed feelings about combining business and personal—so do others—but many of the people in your network aren’t going to be close friends.

They are more likely former colleagues or acquaintances.

A good exercise here is to scroll through your LinkedIn connections.

You want someone (1) motivated by equity, (2) naturally risk-averse, and (3) driven.

If you see a potential fit, reach out.

The opportunity to lead a company—and participate in its upside—is a gift.

Most will be grateful you even considered them.

They can always say “no”.

2. Customers

The people who work for your customers will understand your industry and what it takes to win new business.

Again, use LinkedIn and prioritize:

  • A history of consistent promotions
  • Stability of employment (long tenure)
  • People leadership (they run a team similar in size to your org)

Depending on your business, a sales or external role can be a big plus as well.

3. Training Grounds

There are a few career paths that attract highly motivated leaders.

A few examples:

  • Military
  • Athletics
  • Healthcare (eg. medical school)
  • Big 4 accounting (KPMG, Deloitte, PWC, EY)

These are demanding jobs that attract really strong talent (early in their career).

Someone with experience in these industries may want out.

They’ll take a lower guaranteed salary for more balance and equity upside.

Their learning curve might be steeper—but have patience.

4. Recruiters

If you strike out across the other three sources, you may consider hiring a recruiting firm.

They are expensive (fees = 30% of the candidate’s year 1 total comp), but their incentives are aligned with yours.

📚 Caught my eye:

A simple explanation of the benefits of tax loss harvesting


Not everyone is meant to be an entrepreneur.

That doesn’t make them any less valuable, talented, or capable.

Your job is to be the connector.

Connect a great business, with a great operator.

Then get out of their way.

See you next week,


Build Your Wealth

Join 4,000+ high earners receiving 1 actionable tip every Saturday morning to build their income and accelerate towards financial independence.