How My Art Degree Has Made Me A Better Tech CEO

As one tech leader sees it, the Information Age favors artists “because they can create amid disorder.”

How My Art Degree Has Made Me A Better Tech CEO
[Photo: Bamboo Cinema, 2001 by Teresita Fernández. Courtesy the artist and Lehmann Maupin, New York and Hong Kong via Wikimedia Commons]

Today you’re more likely to find tomorrow’s tech innovators at art schools than MIT. From the inventor Leonardo da Vinci to the technologist David Bowie, history is full of creators who defy the neat division between right-brain creatives and left-brain analytic thinkers. My own career has crossed and recrossed those boundaries, too. When I started my company, Tradesy, I had no real entrepreneurial experience. My professional network contained a lot more light sculptors than Internet professionals. I was also a woman turning 30, breaking into an industry saturated with fraternity-aged CEOs and 30 under 30 lists. But if the transition from art to e-commerce seemed unconventional to me at the time, looking back, it was actually a pretty natural one. Here’s why.


How Art And Tech Already Intersect

During his time as president of the prestigious Rhode Island School of Design (where the founders of Airbnb were famously art students), John Maeda worked hard to forge a new relationship between art and technology–part of an effort called the “STEAM” movement, designed to add an “A” for “Art” into the mix of STEM programs. Maeda also promoted creative leadership training, believing that the tech sector could benefit from more artistically minded thinkers.

Newly minted Benchmark VC partner Scott Belsky, founder of Behance, might agree. He’s said that the art-driven “interface layer”–the place where technology meets design and usability–may soon become the more valuable piece of the formula for tech companies to focus on than the underlying tech itself.

Startups may be accustomed to paying top dollar for leading technologists, but many are coming around to valuing design thinking more highly. Where Apple once stood out because of its high-design edge, aesthetics and experience are no longer an add-on or the calling card of just one brand: Those considerations are fundamental. As a result, tech recruiting firms are cropping up that specialize in design and user experience candidates. They hunt for talent in an increasingly competitive landscape of high-tech creative candidates, much the way recruiters have long sought after talented software engineers.

Here are some of the advantages that, in my experience, make artists natural fits as tech leaders.

Photo: Flickr user Andrew Russeth

1. Original, Unshakable Vision

Every great business has a vision of a future world to strive toward and a mission describing how to get there. Some companies started with visions that once seemed outlandish, unlikely, or just plain crazy at the time, much the way some of the most celebrated works of art were poorly understood in their day. Vincent Van Gogh famously sold just one painting in his lifetime, and made The Starry Night from inside an asylum. Herman Melville died thinking himself a failure.

Original ideas are exactly what great art–and innovation itself–is all about. The artist and the entrepreneur both envision something that only they can imagine. Others may dismiss, reject, or fail to understand it. Yet both want to share their visions to make them real. They’re driven to create, not strategize


Even Google’s vision, “to provide access to the world’s information in one click,” sounded pretty absurd when Larry Page and Sergey Brin first offered it in 1998. But they had a practical mission for realizing it–and set about organizing digital information in order to make it more widely accessible. They ignored skeptics and pushed forward.

Finding Connections In Chaos

The day-to-day experience of running a company, I’ve found, has a lot in common with the daily practice of making art. You combine the elements you have on hand in innovative ways in order to make something that’s especially elegant, or useful, or both.

Psychologist Frank X. Barron found in the 1960s that artists prefer complexity and ambiguity to simplicity and order. People who identify as artists early in life often do so when they discover a knack for making unexpected connections among ordinary things, which leads to surprisingly beautiful creations. Artists, in other words, can see patterns in the data of life.

What’s more, they thrive in the Information Age–where the only constant is change–because they can create amid disorder. A founder who detests chaos may react to the volatility that comes with running a tech startup in ways that limit creativity. An artist’s approach is more likely to let teams discover, experiment, and push boundaries–quickly and repeatedly.

Visual Expression Can Lead To Love For Math And Data

I pretty much abandoned studying math after the 10th grade, and I didn’t learn how to use Excel until it was absolutely necessary, to make the business forecast I used to raise our seed financing in 2012. I thought I wasn’t a math person because I was an artist. It was easy to believe because math hadn’t come as naturally or immediately to me as art had.

But math can be a creative language and a beautiful medium for artists–even those of us who slept through it during sophomore year. Artists often discover that hidden facility when they learn to view it as a language made of numbers–just like the words we write with or the shapes and colors we paint with. A great business model is a colorful and descriptive illustration of your vision, expressed in that qualitative vocabulary.

Photo: Flickr user cea +

Risk Taking And Rebellion

Barron also observed that artists were highly independent, averse to convention, and willing to take risks–which sounds like just about every successful tech CEO I know.

Perhaps because both the art and tech markets are unpredictable and prone to constant disruption, both artists and founders need a sharp eye for it, a strong appetite for risk, and a thick skin for criticism and rejection. What’s more, existing ways of doing things only change when someone rebels against the status quo and invests a better way. In the startup world, we call those people disruptors, but we may as well call them artists.

The most successful founders aren’t right all the time and sometimes succeed, despite getting things wrong. But they keep taking big, high-stakes risks without delay. Risk-averse leaders simply can’t operate in today’s tech market. And artists understand risk taking in ways that most others can’t–having long eschewed the safety of institutional boundaries.

As an artist, I’d spent the better part of a decade taking huge, calculated risks in an attempt to break into a ruthlessly competitive market. My job was to question the status quo and challenge myself to do the things that scared me most, all in the name of making better work. I failed many times–and made some embarrassing art–but I’d gotten used to moving quickly and boldly. Even without a STEM background, I was more prepared than most for the role of startup CEO.

Leaving the art world behind was frightening, but because I was already comfortable with risk, I was able to take the plunge. I realize now that building a startup is an art form in itself. Any nerves I had about leaving art have dissipated. Tradesy is the best artwork I’ve created so far, and I’m not finished with it yet.

Tracy DiNunzio is the founder and CEO of Tradesy, the mobile and online marketplace where more than 5 million women buy and sell fashion from their closets.