How To Hire 50 Awesome People Into Your Startup

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

Joe Procopio
6 min readSep 29, 2022
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



Joe Procopio

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