How Startup Leaders Become Quick Experts At All the Skills

If your startup is lacking experience at a certain skill, don’t do the thing most entrepreneurs do

Joe Procopio
4 min readMay 12, 2022


image by pikisuperstar on freepik

This is another one of those questions that I get from entrepreneurs quite often. It’s also a paradox I struggle with myself, even after two decades being an entrepreneur with multiple successes and failures.

How do you efficiently fill the gaps for the skills your startup doesn’t have?

The funny thing is — that’s rarely how the question comes to me. And I understand that. I mean, if you’re going to be an entrepreneur or a startup leader, and attempt something no one has ever done before, you’re going to need a pretty strong ego. That same ego is going to stop you from putting a hand up and saying:

“I suck at this skill. What do I do about that?”

Here’s what you do.

Should You Hire a Professional?

The question about filling skill gaps almost always drops in my lap disguised as another question, specifically, a strategic hiring question.

In other words, when the startup doesn’t have in-house resources to get to the next level — maybe software development, maybe sales, maybe accounting, whatever — they decide they need to bring in a pro, but they don’t have the available funds to do so.

Then I get that question: How do we pull that off?

Last week I got one of these questions from a startup CEO: When is the right time to seek professional design for their app?

The app is still in MVP, but it’s already generating revenue and adding customers at a good clip. While the CEO didn’t see any evidence of the “rudimentary” (his words) design turning away potential customers, he felt like it was only a matter of time before their ugly app began to stunt growth.

He’s not wrong. But from everything I could see, it wasn’t time to press the (expensive) panic button and bring in design professionals. Not yet. His product worked. It did what it was supposed to do. It solved customer problems.



Joe Procopio

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