The Artist as Founder, the Founder as Artist

When I first left the arts world for the startup world, one of the things I loved about the change was that in the latter, it’s much easier to know how you’re doing. As an artist, there’s a constant tension between expressing your vision and pleasing your audience, and the most commercially successful work is rarely considered the best. In the business world, those two factors are much more closely correlated. It’s at least theoretically possible to write the Great American Novel that no one ever reads. But you obviously didn’t start the Great American Company if no one ever bought your product.

As a fiction writer I often struggled with the fact that audience feedback would sometimes pull my work away from what I’d originally been trying to create. It was tempting to think “fuck what they say; I’m doing what I want,” and I often did. I don’t think that kind of response is necessarily illegitimate, but I was never sure I was making the right call.

When I became a startup founder, that ambiguity disappeared. As Marc Andreessen once said, “the market pulls the product out of the startup”: if the vast majority of your customers want you to change your product in a certain way, you should probably do what they want, regardless of how it differs from your original idea. This rule isn’t absolute, and the truest visionaries are capable of reaching below the surface to understand what their customers are really asking for (“If I’d asked my customers what they wanted, they would have said a faster horse”), but the general principle stands. The lone builder toiling fruitlessly on a product no one wants is a hundred times more likely to be a fool than a genius.

At first, I found the clarity the market provided to be a relief. But eventually I found something in it wanting. Building a great product takes real skill, but when you’re deep in the creation process, it doesn’t always feel that way. If the market is indeed pulling the product out of you, you sometimes feel less like a creator and more like a mere conduit. Perhaps that’s why you see pretentious entrepreneurs self-describing as artists far more than you see the reverse.

As I’ve gotten older and become at least theoretically more confident in myself, I’ve started to feel more comfortable creating without the guardrails market feedback provides. And I’ve learned to listen to a different kind of feedback that’s harder to tap into, but just as valuable: the kind that comes from within. When I’m writing something that’s really working, I can usually feel it. Or at least, I think can.

A Not So Simple Story

Of course, like all things, the product-art division is more of a spectrum than a binary. Games like Journey, or tools like The Most Dangerous Writing App, are somewhere in the middle; so too are the books of James Patterson, whose factory-like process for putting them out includes a team of employees who do most of the actual writing.

Every creator has to think about where on this continuum they fall. I’ve written before about how with this newsletter, I’m intentionally pursuing my own whims at the expense of creating something that might be more broadly appealing. By eschewing a simple pitch for what this newsletter is “about,” and by not providing my readers with any obvious practical value, I’m almost certainly slowing my audience growth. To some extent I view it as a challenge: if a great writer can make any topic interesting, then if I keep writing about whatever I want, I’ll have no choice but to either lose all my readers or become great. 

Call Me By Your Noun

I’ve used the term “artist” throughout this piece because I couldn’t come up with a better one, but the truth is I would never actually call myself an artist. That word feels way too self-aggrandizing, with its implicit assumption that these weekly newsletters qualify as art. I didn’t like calling myself an entrepreneur either—I was just a guy who happened to be building a company—but now that those days are firmly in the rear-view mirror, I’m more comfortable describing myself as having been one.

Perhaps I’m just searching for a middle ground. My adolescence in the arts world taught me to make something beautiful; my young adulthood in the startup world taught me to make something useful. I’m not sure my writing is either, yet. But hopefully one day it’ll be both.

Yours in hoping no one sees through my technique of using section headings to make a few different ideas seem more interconnected than they actually are,