Separating art and commerce in entrepreneurship

Alissa Orlando
3 min readMar 20, 2021

I was reading Cheryl Strayed’s book Dear Sugar, a compilation of real-talk advice columns. Someone wrote in bemoaning that, despite attending prestigious colleges, she had not landed a six-figure book deal and was unable to feel happy for friends who had. Strayed laid down the facts:

“We are not talking about books. We’re talking about book deals. You know they are not the same thing, right?…Your cause is to write a great book and then to write another great book and to keep writing them for as long as you can. This is your only cause. It is not get to get a six-figure book deal. I’m talking about the difference between art and money; creation and commerce.”

The parallels between artistry and entrepreneurship also struck me in Kent Newburn’s Dancing with the Gods, where he also draws a distinction between art in service of beauty and art in service of commerce.

It is a loss to our society that we never discuss entrepreneurship in service of beauty. What if the world’s entrepreneurs focused on building products, services, and business models that served a vision untainted by greed?

At Stanford Business School, courses titled Lean Launchpad and Startup Garage had us searching for problems to solve, but the only “worthy” problems were linked to a market size of at least a billion dollars. Passion and vision be damned.

Could you imagine if we treated art the same way? Artists should only pursue endeavors if we thought they would make a billion dollars? Our most beautiful creations, even those that have coincidentally made a billion dollars, would never have come to be. We’d only have obvious hits, no breakout surprises like technicolor soup cans or graffitied children releasing balloons or BDSM love stories.

This is what is happening in business. We’re losing the bold and the beautiful in service of the sure bets. The productivity tools, online marketplaces, and enterprise APIs that make up venture capital funds’ portfolios have no soul.

I want to see more entrepreneurs self-identify as artists. People who want to create to birth something into this world. This is not to say abandon any business model or make no money. Artists have to cover their costs. So too should entrepreneurs. But it is about changing the origin point from servicing a billion dollar total addressable market to servicing the same masters as art: aesthetics, emotion, and inquiry. Money then becomes the necessary evil required to further create, not the primary measure of success.

The masters of commerce, whether they be venture capitals or book publishers, will always try to distort the purity of creation. Just as artists must balance the dueling masters of art and commerce, so too must entrepreneurs.

This will mean struggle. It will mean scores of crumpled ideas in the wastebasket because they don’t truly sing. It will mean a draining level of emotional intimacy with your work. It will mean paying your own bills until you can prove to the masters of commerce that your creation is worthy of their endorsement. This, of course, requires privilege, tenacity, or both.

But if entrepreneurs start building with the sole objective of raising a round, it will lead to soulless creations, in the same way it would for an author who writes with the sole objective of getting a book deal.

Entrepreneurs — can we liberate ourselves with permission to create in service of more than blank checks?

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Alissa Orlando

Gig economy operator (ex- Uber , Rocket Internet) turned advocate for better conditions. Jesuit values Georgetown, MBA Stanford GSB.