Don’t Hire Your Friends Into Your Startup

You need resources quickly. Should you hire friends and family?

Joe Procopio
5 min readJun 16, 2022


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At what point does your employee become your friend and at what point does your friend become your employee?

This is one of my least favorite questions. And I get it more often than you’d think. Because it’s where a lot of startups fall apart for the worst possible reasons.

My own work history isn’t any different than most. One of my best friends in the world is someone I hired into my startup. And one of the worst enemies from my past is someone who hired me into their startup. I’ll probably make a few more enemies by the end of this post.

But that’s OK, because we probably weren’t friends to begin with. We just worked together.

Friends Versus Employees

A couple of weeks ago, Teaching Startup got a question from an entrepreneur who had just closed their first major B2B deal, and now needed to hire up quickly to meet the terms of that deal. Fortunately, money wasn’t an issue, as the customer had already paid, but time was very much of the essence.

So should he just hire his friends and former coworkers or what?

One of our advisors, Rachel, gave a crisp and thoughtful answer based on her experience hiring friends and family into her many companies, and she went into both the good and bad.

But I want to talk specifically about friends versus employees.

The problem with hiring your friends, family, even just former coworkers, is that you’re assuming, or even just hoping, that the dynamics from one relationship can translate into the dynamics required by the second relationship.

This never happens. And the determining factor in whether or not both relationships survive, personal and professional, depends on how ready you are for that problem to get ugly.

Never Say Never

OK, so as a rule I never hire my friends, but it’s a rule I’m ready to break for the right reasons and under extenuating circumstances. In those situations, I know I’m going to get burned, so it’s a rule like “Never get on the highway at 5:00 pm on a Friday.”



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at