Even the Best Startup Leaders Have This Weakness, This Is How I Fight It

Some strategic skills are more critical to success than tactical skills

Joe Procopio
5 min readMay 9, 2022


image by fabrikasimf on freepik

Entrepreneurs are flawed animals.

There’s got to be something wrong with anyone who willfully jumps at the chance to make less money to work harder with no recognition.

But in all seriousness, even us entrepreneurs who are most comfortable in the skin we’ve chosen know that we’re playing a role that often requires us to be really good at a lot of different things, all the time. To me, that’s a challenge and even a joy — waking up on any given day and not knowing if I’m going to have to be a salesperson or a marketer or a coder or the boss that day. Or all of them.

But here’s a secret that no one tells you about being a successful entrepreneur: You not only have to be good at a lot of diverse tactical skills, you need to be better than most at a lot of strategic skills too.

And there’s one soft skill that I still suck at — even after 20+ years of founding and leading companies. And I’m not alone. I see this take leaders down repeatedly.

Why Strategic Skills Are Critical To Startup Success

The good news is that you don’t have to be an advanced technologist plus a financial wizard plus a sales guru plus a hiring machine all at once to run a successful company.

Take software development, for example. I was an OK coder, better than average. But in startup, when I reach the end of my usefulness writing code, I can just go find a technical co-founder or a CTO to fill my gaps

What I do think I’m very good at are the strategic programming skills, like pattern recognition and creative problem solving.

Those strategic coding skills actually worked against me in the corporate world. If someone told me to code something to spec, and I found a better way to do it, I’d just do it my way. And then I’d get in trouble for it (not a team player, doesn’t follow directions).

But in startup, finding better ways to do things is rewarded — with customers, revenue, and market share.



Joe Procopio

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