FUNNY WOMEN #121: I Sold My Software Company and Now I’m into Art


Hi, I recently sold my software company and now I’m into art. People were always saying, “Find your art” and “hone your craft,” and so I turned down the Arcade Fire, gave my Rumba a five-minute break, asked an intern to muffle her unpaid laughter, opened Photobooth so I could stare deep into the windows into my soul, and finally, I was able to hear them.

Building a really successful, incredibly efficient metadata-driven software company that changes the way we think and feel about metadata and making art are not that different. I know I sound like I’m in some nebulous limbo between innovation and certifiable confidence, but that’s just my creative mind at work.

I sense you’re doubting my “authenticity,” and I get it. I do. But hey! I’m Real. My artistic instincts come from an honest, urgent need to express the heck out of life and push all of the envelopes out there. Like, I see an envelope, and I push it. Couldn’t stop if I tried! Have I tried? No.

I’m not into art for the trendy studio space, although I just had this Feng Shui artist come in and redecorate, and now my space is looking dope. And conducive to flow. This dude redecorated Zuckerberg’s doghouse, so I figured he’d be top notch. I wasn’t wrong. Creative minds don’t dabble in right/wrong moralistic binary, anyways. Everything just is what it is, and that’s art.

Daly1The point is, even I can admit it’s difficult to generate spontaneous inspired feelings while languishing in financial stability. But I have a dark underbelly, too. Earlier today I stared out the window and wondered, “Why?” Last week, I bought a $300 pair of flip-flops, and then later I found out that style of footwear is usually less than $10. I don’t care about money—this is about betrayal. Which is something memoirists often write about. So I took that existential confusion and made a four-minute photomontage of me and my friends vacationing in Hawaii, set to a loop of socially conscious hip hop, slowed down to half-speed and chopped and screwed. It took all that crafting to piece together my shattered psyche. #sensitivity

How’d I get into art? Art chose me the moment I realized I could handle it. After watching my start-up blossom into the 300-person company that it became under my inimitable leadership, and with the help of marketing data from undisclosed online sources, I think I can honestly say I definitely know what people think they want. They want inspiration. They want decisiveness and intention. They want evocative-ness and a royal blue motif, rendered fuzzy through the application of three layers of Instagram filters, with a sweeping, sad, hyper-real statement like, “LIFE IS BULLSHIT” hastily scrawled across the middle third. People want to walk around a gallery, stop at your framed picture of the sculpture you 3D printed and imagine it hanging tastefully above their electronic fireplaces, and they also want to know that over 27 hours of despair and some irony went into it. But most of all they want to feel understood. And well-liked.

My former colleague Michael once told me at Happy Hour that I was the most emotionally perceptive person in the company. He was an intern and I was CEO, but I consider him a colleague because I relinquished my sense of hierarchy when I moved to California and got into Art.

How has my life changed since becoming an artist full-time? I’ve found myself doing a ton of whimsical stuff. I see a line outside a restaurant, and I’ll go stand in it—partly because I think lines are the purest distillation of life, combining the excruciating process of living with the comfort of existing among distant strangers with whom you share a common goal; and partly because I’m a total foodie with a ton of free time. I’m not trying to unpack that too much. Art’s my gift, and it’s unhealthy to scrutinize it. (I learned from a blog I skimmed that artists have an unconventional amount of intuition, so I go with my gut and ride whatever wave comes my way, especially if it’s in a controlled, supportive environment and there’s an instructor nearby.)


Rumpus original art by Annie Daly.


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Sam Riley is an adult who works at McSweeney's. More from this author →