When to Start Hiring

Hey y’all — let’s talk about hiring.

First, I’m hiring!

I’m looking for two people to report directly to me. To apply or refer someone, just email me. I’ll give you $1,000 if I hire someone you introduce me to.

The two roles are:

• Social Media Manager (for Megaphone’s ghostwriting agency)

• Account Executive (for Founding Journey + more brands)

Second, and more broadly relevant, when should you pull the trigger on hiring?

This is a surprisingly short list.

Most startups hire people for bad reasons. Maybe they feel like they have to, or that a larger headcount is a sign the company is successful. False.

I’ve kept my team lean over the last two years, after over-hiring at my last startup, so I’ve seen both sides of this.

Here are 5 reasons to hire, and 1 caveat:

When to Start Hiring

You’re at (or Near) PMF

The ideal case, of course, is that you’ve been able to hold off on needing to hire anyone until you hit PMF.

Not only does this keep burn to a minimum, it also removes all of the complexity that comes with hiring people. You can just be a maker for as long as possible, before needing to be a manager too.

This is only possible if the founding team can do everything, both in terms of skillset and bandwidth.

Further down the road, you should still hold the same principle — ideally you’re hiring at times growth accelerates.

A good question to ask yourself as you read the rest of these is whether or not you could find a way to not need to hire, despite one or more of these being true, and wait for this ideal case to be true instead.

After You’ve Done It Yourself

It’s worth doing most things first yourself so that you can:

• Better define the role for the person you eventually hire

• Provide them both an accurate northstar and more specific guidance

• Confirm if you really do need to hire someone for this yet

This is more useful for first-time founders, but can apply even on your second or third company (especially if there are areas you’ve never led before, but now will have to).

You Realize a Critical Skillset is Missing

Probably the best reason to hire pre-PMF is because you realized that your founding team does not have a specific skillset that is mission-critical to the success of the company.

It’s fair to wonder how this could even happen in the first place, but there are legitimate reasons (the most common two are after a pivot or a member of the founding team leaves). Other times you just hit a bottleneck you failed to anticipate and, ironically, to solve it you need to slow down more to spend time hiring.

The important point here though is that you must be honest with yourself about this. It’s all too easy to delude yourself into lowering your bar for what “mission-critical” actually is — don’t let yourself do this.

They Will More than Pay for Themselves

Revenue-generating roles are the easiest to justify, especially if you haven’t raised money yet (or don’t plan to).

Will they add more than 2x in revenue what you’ll pay them per month?

If the answer’s yes, it’s worth considering. I say 2x because if it’s less than that the managerial overhead isn’t worth breaking even on.

You Just Raised a Bunch of Money

I hesitated to include this, because raising money doesn’t necessarily mean you should go spend it on a bunch of hires.

But, chances are you raised that money with a specific plan, and that plan likely includes making a few key hires.

So it’s sort of a self-fulfilling prophecy.

But make sure it’s enough money to justify the hires. I’ve seen companies that only raised a few hundred thousand dollars go out and add people whose combined salaries are more than they just raised. That’s either extreme confidence or… something else.

One Caveat

Just because you shouldn’t be making hires doesn’t mean you shouldn’t be hiring.

That sounds weird but it’s true.

Always be accepting applications, taking some meetings with interesting people, and engaging your network about how things are going.

Some people may scoff at this but it’ll mean you can more easily pull the right people in when the time comes, quickly.

This is particularly true for generalists.

At a startup everyone has to be generalist sometimes. So they’re good people to know hire. But you should only bring them in when you have a specific role that, hopefully, will interest them and they’ll be a fit for.

How We Can Help

Advertise in my newsletter to get in front of 70,000+ founders.