The Most Important Question To Ask Your Customers

Lessons learned building my startup to help other startups

Joe Procopio
7 min readAug 15, 2022
image by diana grytsku

I’ve built over a dozen B2C and B2B startups over the last two decades, including two right now — one VC-backed high-growth company and my own bootstrapped project. One common thread across all of these companies is this inescapable fact:

If you want to learn about what your company needs to do to be successful, you have to look deep into the magic mirror that is your customer base, and ask some hard questions.

That’s what I did last month, and here’s what I discovered.

But first, a little context

Just over two years ago, I founded Teaching Startup as a project startup to fill the gap between the “free” startup advice posts I write and the crazy money I get paid as a formal advisor.

Teaching Startup fills that gap with expert answers — based on actual questions from working entrepreneurs — with over 300 answers in the database, ready for when you have a question. And if the question isn’t there, you can ask your own, and then that answer gets added too.

It’s a nice virtuous cycle, and thus, it’s a startup that helps startup founders do their startup. That’s an important statement when we talk…



Joe Procopio

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