How To Hire 50 Awesome People Into Your Startup

By the time you get to 20 it should be a breeze

Joe Procopio


image by yanalya on freepik

Hiring is hard. When you’re a startup — with no track record, scant funds, and less than top-of-line resources and benefits — it’s usually a nightmare.

Thus, many startups never make it out of the “solopreneur” stage — a one-person show. There’s nothing wrong with that, of course. But if you’ve got billion-dollar valuation dreams, or heck, even if you just want the slightest chance of an exit at some point, well, I probably won’t be the first to tell you that you can’t do it alone.

I’ve been down the growth startup hiring path many times, several as a self-funded founder, and even more as a founding stage executive at a VC-backed company. The truth is, while money makes the hiring process easier, it doesn’t make any of the decisions easier, and it doesn’t guarantee hiring success.

That said, I’ve been lucky enough to have hired some of the most brilliant and extraordinary talent during my 20+ year career as an entrepreneur.

I’ve also worked with a few bozos, because we all make mistakes.

The first hire is the hardest

While we’re here, let’s get this misconception out of the way up front. No one works for free. Ever. If a company is offering less than competitive compensation for any hire, whether that’s employee #1 or employee #50, the difference will need to be made up in equity. If it isn’t (and sometimes even when it is), you’re not going to get the full effort — and thus the full value — from that employee.

Also, despite how the math might look, two startup employees working part-time do not equal one startup employee who is all in. They usually equal one startup employee working part-time, because it’s a total pain to get results out of part-timers. Because it’s their second job. Or their third.

Let’s face facts here. Money is always the primary decision factor. So unless you land some seed investment, enough to provide at least a year or more of fully-loaded salary for your first hire, plus whatever other expenses you’ll generate over that time, you’re going to have to pay for that hire out-of-pocket or with revenue. And that revenue is…



Joe Procopio

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