On Failure

1 December, 2008

The following is the personal statement I submitted today as part of my application to NYU ITP. If accepted, I would start at ITP next fall. The prompt for the essay was: "Tell us about your biggest failure." With so many startups big and small closing their doors or altering their strategies to suit more difficult times, I thought my answer to that question might be of interest to an audience broader than just the ITP admissions committee. Enjoy.

Five slides into my presentation, the VC stopped me:

"We've seen your deck. You sent it to us. Let's just talk."

It was a reasonable request--not rejection, necessarily. Still, my mind flashed to the weeks I'd spent that summer crafting my pitch, carefully composing the slides, working with more experienced mentors to shape the argument. I recalled the hours I'd spent practicing the delivery, stumbling over the script in my silent room until, with Fourth of July fireworks going off outside my window, my awkwardness dissolved in favor of a kind of automatic competence.

In the process of practicing it, I'd come to believe our pitch absolutely. The music industry was hopelessly out of its depth in the roiling sea of a newly decentralized online media. They were drowning in influential blogs, mortally threatened by monopolistic distribution cabals and peer-to-peer file-sharing pirates. Our search and metadata detection technology was like the accurate clocks that solved the longitude problem: it would give them precise knowledge of their music's online position so they could reach their marketing objectives without hitting quite so many hazards.

In working so hard to become convincing, I'd convinced myself. The challenges these big conglomerates and famous bands faced were serious and important. Our solution was urgently needed.

Later, at the wood-paneled bar next door to the firm's chic office, my partners and I reviewed the carnage. Over the course of an hour-long argument, we'd gotten the VCs to grant most of our major premises. They believed our technology could do what we said it could; they'd been impressed by the demo. Then what was the problem? How had we ended up sitting here glumly eating chichi fried foods when we should have been celebrating?

It was the math that killed us. They simply didn't believe the music industry was a big enough market, they said. Even if we captured every potential customer we couldn't possibly make enough money to get them the "ten ex" return on investment they demanded. They'd done the math and the math was unassailable.

So we sat, trading morbid jokes and concealed glances across the bar to where the VCs drank dark, expensive beer and tried to keep the greasy food off their white-cuffed shirts. But even as we mocked the absurdity of their slavish adherence to their rigid formula we were internalizing their critique. We hadn't seen the technology as a product that needed to be sold to masses of users, but rather as an idea whose obvious rightness would obviate any obstacles. In the face of their math, this view seemed hopelessly naive.

We started brainstorming, running through every money-making scheme our technology could power. And before too long our voices rose in excitement. We'd found a new business plan, one that could withstand the math. We egged each other on into a new round of of optimism. I could already see the outline of a new pitch taking shape, fresh slides, an updated script.

There was more convincing to be done.

I never meant to start a company. What I'd wanted to start was a band, but then I met Jim Griffin.

It was my last college semester and I already had post-graduation plans: a group of high school friends and I aimed to reconvene in Portland to find our way to rock stardom. In the meantime, though, I was driving out to the airport to pick up yet another speaker for my department's annual conference.

Griffin was already clear of the gate and waiting when I reached the airport. By the time I'd gotten him into the car, he'd gotten my musical plans out of me and started in with the advice: whatever their apparent glamour, the major labels were really loan sharks in disguise. The bills for those fancy recruiting dinners and high tech studios came straight out of the artists' own pockets; most of their victims ended up massively in debt, their music owned by the labels and likely never to see the light of day.

Griffin, it turned out, was speaking from experience. He'd worked at Geffen Records, home to Nirvana, during the height of the early nineties grunge boom. He'd started a website for the label before most people had ever used a browser and sold mp3s on it ten years before Apple introduced the iTunes store.

Unsurprisingly, his solution to the dilemma posed by the labels' villainy was the use of the web. "Amazon.com is like a woman," he said, visibly entranced by the magic of it. "It remembers your birthday and keeps track of every bauble that catches your eye. It's not generic; it's just for you." The web was an opportunity for bands to get their music out directly to exactly the people who might care about it without needing the labels' big marketing budgets. It was a chance for musicians like me to take control of our own destinies and to change the world for bands and fans alike.

There in my car driving back to campus, Griffin's words hit me like a semi running a red light. I'd never thought of the net as much more than a delivery mechanism for movie previews and email. Even though I'd dabbled in some math classes, as an art major my technical sophistication didn't extend much beyond making collages in Photoshop or formatting the illustrations in my thesis. Griffin presented a vision of the web, and of technology more generally, as a liberating force for creative producers living under the occupation of crass commercial interests.

So I set out to learn about the web. I began by fumbling my way through enough HTML to maintain my band's website between tours and new albums. Gradually my ambitions grew. I wanted to help all musicians take part in Griffin's dream of direct distribution. I discovered 'web apps' and found myself the co-proprietor of one. I learned PHP and then Ruby on Rails. I started a business and then a couple of them. Before I knew it, I'd quit my restaurant job and programming was paying for my rent and for new guitars.

But somewhere in this process, things changed. I went from being a musician who coded to help tell the world about his music to a startup founder who worried that music was too small a niche to hook worthwhile VCs. My aspirations gradually shrank to accommodate the realities of running a business. Rather than striving to build technology that would change the world, I found myself focused on selling the technology we'd already built.

Looking back on that day of VC rejection, I now see two kinds of failure. Obviously, we failed to make the sale: I couldn't convince them that our technology could support a viable business. But there was a deeper failure as well. In dedicating myself so completely to solving their profitability formula, I let its math completely displace the original idea that had drawn me towards the web in the first place. We didn't just fail, we reduced our ambitions to the point where even our success wouldn't mean real change. While the first form of failure bruised my ego, this second one cut me much more deeply

The ITP community lives at exactly this intersection of creative idealism and concrete reality. It knows that practical compromise is almost always necessary and sometimes starting a business is the best way to change the world. But it also knows that unconstrained creative play is the only source of ideas worthy of the sacrifices involved in such a compromise.

By joining this community I hope to permanently avoid the deeper form of failure I experienced when I lost sight of this knowledge and, moreover, to recommit myself to doing justice to that liberatory sense of immense creative possibility that launched me on this journey in the first place.

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