Obsession & the Artistic Entrepreneur

Without obsession, life is nothing. — John Waters

I obsess over things. Once an idea takes hold, I’m at its mercy. It can arrive in an instant but linger for a very long time, in some cases years and even decades. It can be an obscure hobby (beekeeping), a high-risk activity outside of mainstream ball sports (skateboarding), or it can be an idea for a problem to be solved. Problem solvers are often thought of as entrepreneurs, and they certainly can be, but we’re really talking about two wildly different personalities and skill sets. Yet obsession can give one a false sense of the other.

I mention this because I’ve been obsessively working on a particular problem for quite some time, and as you learn more you might think the time, energy, and money I’ve spent on it makes me an entrepreneur. That’s what I thought too, and I was very wrong. Entrepreneurs are (or should be) serious about things like determining if there’s actually a market for their solution, how to properly reach that market, and just maybe how much it will cost, both financially and more importantly in time. They would do that BEFORE diving into the work, and they’d be right to do so. But that’s not me, and when aiming that laser focus of obsession at a problem, I’ve learned I’m really only solving it for myself.

Project myopia can be a wonderful thing for personal projects where you’re effectively doing pro bono work for yourself. Expectations typically line up pretty well with results when they live in the same person’s head. Or to put it in marketing terms, you don’t have to sell yourself on the benefits of your own idea. Thing is, you DO have to eventually sell others on your idea if part of your plan involves it solving their problems too. For example, a mobile app with a comically ambitious scope. I’m talking about Muster, which is attempting to evolve the concept of an RSVP for the mobile age and in doing so change how we get together with each other in the real world. I’ve been working on it for nearly 15 years, which is slow by almost any standard but insanely slow for tech (the iPhone itself has only been around since 2007). But I’m patient, and stubborn. And I understand that to do just about anything meaningful in life, you must exhibit dogged perseverance and cultivate a certain love for the process of creation itself, with a bright line separating effort from outcome.

So with Muster think an extremely informal evite with a hint of messaging, calendar, a touch of Instagram, even a dash of Strava. I know in marketing you aren’t supposed to define yourself in terms of your peers or competitors but it’s often the simplest way to convey an idea, and zero-sum thinking is usually counter-productive in a world large enough for multiple ideas to co-exist and serve unique purposes. Besides, referencing “the competition” is small potatoes when it comes to Muster and ignoring marketing best practices. Anyway, the idea grew out of the need to distill the communication for getting together down to two possibilities: in or out. Other interesting features evolved over time but that’s still the core of the app: let’s get together, are you in or out?

Seems simple enough, right? I naively thought so too way back in 2010. Turns out there’s a lot of subtlety in event planning, even informal events like meeting up with friends for a coffee. How do people find each other in the app, cultivated friend lists like Facebook? If we’re meeting on Friday in Atlanta (EST) but I create the invitation on Wednesday while in Nashville (CST), what time zone is used? Do you show that time zone in the app? To both people? Is location required or should it be optional, maybe inferred from the title like “Grilling at Our House?” And what about notifications, iPhone and Android users coming together, privacy concerns, etc.? It started to become clear why no other mobile apps have succeeded in solving this ostensibly simple problem, and why most planning is still done with clunky text threads. Enter an obsessive guy with technical skills, a problem to solve, an over-abundance of optimism, and zero regard for proper entrepreneurial decision-making.

Years go by. Then a few more. Plenty of roadblocks surfaced, including a shuttered software development tool (Parse) and a pandemic, among other challenges…but all those design problems mentioned got solved, and many more were identified and solved as well. Not only that, but real-world usage led to several significant enhancements such as event messages and media, invitee groups, plus-ones, co-hosts, min/max attendees, and more. The idea evolved but I stuck to my guns in building the app I wanted, not the app I guessed the world needed. Sure, tons of testing was done with friends and family, not to mention Muster being both a lead sponsor and planning tool for the world’s largest backyard skateboard contest. But at the end of the day every major decision came down to “what do I personally want this app to do?”

And here we get to the real issue at hand. I’ve heard it said that if Bob Dylan hadn’t become one of the greatest songwriters in history, he’d be sitting on a sidewalk somewhere playing the exact same music. That’s an artist. An artist creates because they can’t not do it, and the best artists create for themselves, regardless of whether they ultimately sell their art or perform it to make a living. With art, success lies in the creation itself, not in how it’s received by others — Vincent Van Gogh only sold one painting in his lifetime!

Business is in many ways the opposite of art, where success is necessarily defined by others voting with their wallet for a product by trading goods or money. App-making is certainly a business, I mean apps are literally published in an app STORE. So it’s difficult to make the “apps are art” argument with a straight face. Yet there’s an artist inside this engineer who is dutifully committed to creating the ultimate real world social app purely for myself. And at the same time publish it in a store where others get to decide if it also provides any value to them.

The irony that this ruthlessly individualized app depends on others for business success isn’t lost on the artist in me, yet I can’t not create it. The resulting conflict is real, and the jury is still out on whether this particular marriage of technology and liberal arts ultimately delivers on that famous Steve Jobs insight. In the meantime, if you ever stumble across a guy on a sidewalk sitting on a skateboard with a laptop coding away, consider downloading his app and inviting him for a coffee. I’m in!

Muster is available now on the App Store, built by Stalefish Labs.