By Chris Kay

Hi, I’m Chris. [Your turn: “Hi Chris”] and I’m a recovering business literature reader. I’ve been clean, ah, or I haven’t read a business book in about two years. My “drug” of choice was anything to do with finance, economics, startups, management, or strategy. I assure you I’m not some ill-witted troglodyte devoid of the good sense to better himself, for at a time I would gobble up those pages like candy. No, what happened was I became disheartened with the overlapped, repetitive, and derivative nature of most business literature (I use the term “literature” loosely) as of late. I felt like I was getting little value out of these books in information and in inspiration for the time I spent reading them. I also felt like the wisdom and ideas I was getting from these publications were causing me to run the same conceptual path as my peers, or as Rob May, CEO and Cofounder of Backupify put it “Every person I met seemed to read the same tech blogs, have the same information, share the same opinions about the same topics, and have the same business ideas.

To be blunt, I was bored with business literature and the conventional schools of thought in their pages. So I turned to the dark side, fiction, specifically American modern classics and the weirdo tales of the counter culture. There was something that drew me to the words of great men like Ernest Hemingway, Hunter Thompson, Charles Bukowski, and Jack Kerouac. But more than their words, I was drawn to their ideas, their freethinking, idealistic, rebellious ideas. The same types of ideas that the original 1960s hacker culture was built on.

Since my departure from the business literary influence, I began to notice something strange, I was thinking differently. Instead of Michael Porter and Steve Blank metaphorically sitting on my shoulders, whispering strategic business advice in my ear, I had Henry Rollins and Hunter Thompson screaming anti-establishment, anti-mass society sentiment, and blabbering about their interpretation of a social utopia like Jiminy Cricket wearing a Guy Fawkes mask.

Because of my exposure to these men’s words my ideas, perception of the world, and thinking process changed, I saw a different side of the coin. I started to think more creatively opposed to analytically, which as I’m an analyst by trade, this is huge. Then my change in perception started causing me to see things in business I never saw before; for instance, you know how storytelling is all the rage in marketing right now, guess who is great at storytelling. Literary writers that’s who. It’s literally their jobs to tell stories.


Now, I’d like to think I’m a smart guy, but I’m not delusional enough to think that I’m the first person in business to be influenced by artists. The late great Steve Jobs was quoted in his recent biography as saying “Dylan’s words struck chords of creative thinking” when he discussed Steve Wozniak and him bonding over Bob Dylan bootleg albums. Plus we can’t forget the legendary calligraphy class that Jobs audited at Reed College which inspired the famous Mac typefaces and clean design, which as Walter Isaacson so eloquently phrased as “It was yet another example of Jobs consciously positioning himself at the intersection of the arts and technology”. Even this intersection of art and technology is still happening to some degree today, as Elon Musk reportedly came up the idea for the Hyperloop on his trip to the 2004 Burning Man. These examples of Jobs and Musk are just the types of stories that get my blood racing; two intelligent and creative people drawing inspiration from unconventional places. Again, I’m going to have to borrow a line out of the Rob May playbook and agree that “If you really want to innovate, do something different, something daring, and something unconventional”.

So to go a step beyond finding pure inspiration in unconventional places, the idea of concepts and knowledge being shared across disciplines has always been fascinated me. I’m always amazing to see when a concept that is considered commonplace in one discipline is repurposed as a new idea in another discipline. For instance, starting in the early 1980s the mathematical concepts used in thermodynamics were adopted by Wall Street quantitative analysts to price financial derivatives. By adding a new perspective, these borrowed ideas can solve problems in unthought of ways and breathe new life into a plateauing schools of thought.


A similar phenomena that I find fascinating is when two separate disciplines practice the same concepts, but go about them in different ways. Getting back to the art/technology influence mentioned before, my favourite example of this concept divide and conquer is explained by self proclaimed “bad ass mother f**ker” graffiti writer/hacker Evan Roth regarding his quest to build a dialog between hackers and graffiti writers based on their common themes:

“Computer hackers take a digital system and perform some small alteration to change the general intent of that system…With graffiti and street art, and everything surrounding, it’s really the same thing… You see it with traditional graffiti like bombing and tags, but you also see it with a lot of street artists, where they’re hacking different systems, whether it’s billboards or it’s telephone booths.”

Roth, sitting on both sides of the proverbial fence sees how these two communities would benefit from coming together (see, now the title makes sense) to sharing ideas, ideas that would seem unrelated at first, but changes the landscape when adopted by the opposite side. For instance, in Roth’s 2012 Paris Tedx talk he takes Eric Raymond’s seminal essay “How to Become a Hacker” and “hacks it” to be a how to document for artists, using the same principles hackers live by.

So what does this all mean? Why should anyone care? Well, what all of this back and forth influencing and sharing between business and art comes down to is Entrepreneurs and Artists are both creative people, an idea that is, at least in my opinion, best described by Faisal Hoque when he said:

“It is safe to say that more and more entrepreneurs are artists, and artists of all kinds are entrepreneurs. And the trend is only on the rise as all things (art, science, technology, business, culture, spirituality) are increasingly converging. Creativity is the common theme that drives both entrepreneurs and artists alike.

I have come to realize that artists and entrepreneurs not only share a creative theme, but actually practice the same concepts, but go about them differently. To be more specific I think artists and entrepreneur both:

  • Make something new based on internalizing their observation of the world around them;
  • Push boundaries of what’s considered acceptable and possible, and
  • Experiment with new media, technology, and materials.

So after this long winded diatribe (thanks for reading this far, you’re in the home stretch I promise) two questions come to my mind: 1) If artists and entrepreneurs do the same things there must be some opportunity to exchange knowledge and collaborate, right? 2) Why isn’t this discussion and collaboration happening in a meaningful way now?

I don’t really have answers to either of these questions, but I’m willing and really excited to find out. I’m calling for a similar “handshake” moment that Evan Roth spoken about, but I want to see this on a broader scale across three paradigms:

  • Words: Literary writers, marketing copywriters, poets, film writers, journalists, etc.
  • Images: Photographers, graphic designers, web designers, graffiti writers, painters, etc.
  • Ideas: Entrepreneurs, activists, technologists, futurists, philosophers, general artists, etc.

I find this handshake idea really exciting; can you imagine the conversation a literary writer, marketing copywriter and journalist could have over the concept of storytelling and encapsulating the reader? Or the conversation a web designer, graffiti artist and painter could have over design principles and colour palettes? Lastly, I want to be witness to an entrepreneur, an activist, and a futurists discussing the role of technology in how our society communicates with each other, or what privacy means in a highly connected world. Think about after each of these conversations, each of these people will return to their jobs the next day with a new perspective on their craft, and hopefully a new inspiration to do something different.

So there’s no point in doing all of this writing unless I have a solution, so here it is, here’s my call to arms: If you are an artist of any kind, an entrepreneur, a technologist, or a creative type in general, and you see this “handshake” between entrepreneurship, technology, and art as an attractive opportunity to exchange knowledge, inspire, and collaborate with other creative types outside of your craft, then join my Meetup Group here. Let’s get a conversation going, let’s do something different.

Thanks for reading,





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Chris Kay is a Financial Analyst, Co-founder of Multiplicity, and the Founder of Aleph X, a collective of Entrepreneurs, Technologists and Artists experimenting on creative projects at the intersection of entrepreneurship and art. Chris writes the blog Creative Convergence where he discusses the Intersection of Film, Music and Technology. Follow him on Twitter – @ChrisJKay