Ug. I’ve always hated that phrase. Recently I figured out why.
To me it’s always came off as a smug comment implying the speaker knows just what it’s like and understands your pain. It’s usually followed up with something like “I was employee #7 once and I was VP development and VP QA!”
Yeah. How can people live like that? Unfathomable.
Real entrepreneurs don’t talk about hats, but why not? Why do I recoil at this attempt at empathy?
I think it’s because in real (bootstrapped) start-ups there’s no such thing as hats, titles, or departments. If you don’t realize that development, marketing, sales, and even accounting are all inextricably linked, you’ll probably fail. You can’t make decisions about any one in isolation. You’re learning how to sell, what to build, what to charge, who will buy, all at the same time. You’re never even thinking in categories like “Marketing” and “Development.”
So I think my disdain comes from the implication that “many hats” proves the speaker “knows just what it’s like,” when in fact the very idea shows you have no idea what it’s like.
People like that will always be employee #7, never employee #1. (Or really employee #0, since everyone I know who has created a successful bootstrapped company paid themselves last, long after other people were hired on, long after profitability.)
Which is fine! But the experience gap is bigger than they think.