What Artists Have Taught Me About Local Business

William Glass
4 min readMar 2, 2017

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“SHADE” by Amber Vittoria (click image to see her AMAZING gallery!

Recently, I had a comedian on my podcast show who also happens to run window cleaning business. I was fascinated by the overlaps between the two worlds, and as our conversation stretched out to over an hour, I realized we were really getting into something.

Business owners don’t just need Guy Kawasaki (great as this book is). This is a human thing! And for business owners that want to connect with their neighbors, there’s a lot to learn by paying attention to all the things human beings do to connect with each other.

So I started digging into the lessons my artist friends have taught me that I think will serve me well as an entrepreneur in a local space. Here are my favs:

It’s Not Only What You Do; It’s How You Do It.

Of course, it’s good to size up competition. But it is easy to overreact, especially at the local level, to competition. If there ever was a bloated field, it’s art. Even so, great artists emerge and get seen. Great artists don’t just make use of a medium. They make it their own, each with a highly individualized way of seeing the world, the craft, themselves, and the relation between the three.

So, even though Pablo Picasso and Rembrandt are both painters, knowing that fact tells you almost nothing about what you get when you turn the corner into their galleries at the Met.

Of course, it’s good to have first-mover advantage and to claim an early stake in an emerging market or field. But art has been around at least as long as business. And if artists, amid all the tradition and all the contemporary noise can still get real differentiation if they’re good enough, that tells me there’s still room in the market for your unique vision. Even if you’re dumb enough to start an ad agency in 2016 and with almost no money.

If the field you desperately want to conquer is already full, that’s not necessarily an indication not to do it. It is, however, an invitation to master a field as fully as you are able, until you can stamp a character into it as unique as you are.

No Faking!

Getting serious with art means getting acquainted with yourself. It means learning — really learning — what your strengths and weaknesses are, where you should grow, and where you should realize you’re just not ever going to grow.

Almost every artist friend can tell me about a conversation, early on, where they got tired of politeness and asked somebody to really give them feedback that would hurt as long as it was true. Good artists know how to take that feedback and turn it into growth. That, in itself, is a talent.

Local business is as much art as science. It’s about serving people as customers you might well see at the game this weekend. Timing connections well, reaching out in the right way, with the right amount of energy and pressure for the right situation and time, is a talent. That’s to say nothing of actually delivering a great product, handling human resources, finance, etc. If you’ve got real talent, though, mistakes, challenges, and tough feedback are going to bring out the best in you.

If you don’t have it, that may hurt to learn. But sometimes the best thing you can do is move on. Either way, the noise of the market, like the noise of the art world, is a gift. It makes the barrier to entry high enough that fakers won’t stay in it that long.

Love Makes You Great.

Of course, there’s a modicum of talent any artist needs. But it’s love that keeps you at it long after it stopped being cute or a good conversation topic.

Walt Disney was rejected 302 times before finding funding for Walt Disney World. Colonel Sanders and his chicken recipe were turned away over a thousand times!

People tell stories like this often as a way to buck up people who are discouraged. Artist friends have taught me that the stories probably actually mean something entirely different.

They’re not about the rewards you might get if you persist. They’re about the kind of person who can’t do anything but persist. It’s what they do, because it’s what they love.

No amount of love for music will make me the singer my friend Ricky is. But love is what drove him to take his talent and turn it to greatness.

Likewise, it’s my love for healthy communities, for flourishing marketplaces, and for happy customers that drives me past every failure and discouragement.

I’m working my ass off, and even when it sucks, I’m doing what I love. What I can’t help but do.

I think that’s why, when I explain what it’s like to be an entrepreneur in the early days, it’s my artist friends who really understand what I’m saying.

What is the love that drives you past every disappointment? Would love to hear from you in the comments below or on Twitter.

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William Glass

Founder @ HeelFlip Media. Early stage entrepreneur. UF / Duke grad.