Audacity: What Entrepreneurs and Artists Have in Common

by | Nov 19, 2020

What’s the difference between tourists and explorers? How are entrepreneurs and artists linked through audacity? What does audacious even mean?  

Jim McKelvey, one of my favorite entrepreneurs and an accomplished glass artist and successful co-founder of several startups, including Square, the online mobile payment company (valued at approximately $80 billion), answered these questions with several analogies that helped us understand and create a clear picture of entrepreneurship. He linked entrepreneurs and artists through a unique and rarely discussed characteristic: audacity

What does audacious mean? According to the Merriam-Webster dictionary, it means “intrepidly daring,” “recklessly bold,” and “marked by originality and verve.” These are words that we could easily associate with artists. Artists, especially the memorable ones, could certainly be called audacious, as they’re synonymous with being rebels, never afraid to question and challenge the status quo, ultimately changing the world of art.

Entrepreneurs also tend to have this quality. They are unafraid to challenge their surroundings, and often have the courage to pursue novel, innovative ideas that can restructure entire industries, a trait that distinguishes them from businesspeople. McKelvey describes the difference by explaining that businesspeople know how to “sing the song” but entrepreneurs are the ones who “write the music.” Basically, although businesspeople are respected and successful, they operate within the set “rules” of a specific industry and rarely seek to push past them. 

McKelvey knows from experience that the two coincide with each other since both entrepreneurs and artists need to pursue originality in order to succeed. He also knows how difficult pursuing originality can be, since it means breaking with what society knows and has previously accepted.  While it is easy to be discouraged by society’s tendency to encourage a status quo, entrepreneurs are good at “getting comfortable with discomfort,” a principle that artists, as well, excel in.

Twilight on the Sound, Darien, Connecticut 1872 John Frederick Kensett American source: Met Museum Archive

Boldly Exploring the Wilderness

So how does this relate to tourism and exploration? 

Picture this: you live your entire life inside the walls of a city, abiding by rules set for you, and never venturing outside. In this scenario, you would be a tourist – following a predetermined map, never questioning the things around you, and never going beyond the circumstances set before you. This is how traditional business environments operate-working within familiar contexts, in known industries, with an acceptance of predetermined rules. 

Picture another scenario: you live your entire life inside the walls of the city, but you always questioned why things were the way they were, and always wondered what existed beyond the walls. One day you decide to venture beyond into the wilderness, where you learn by doing and create your own set of rules. Here you are an explorer. This is entrepreneurship, this is art- throwing the map away and going beyond industry limits to see what other possibilities there are, and developing their own rules through principles of survival. 

To McKelvey, “Entrepreneurship is much more like the wilderness.” Like the scenario, entrepreneurship is venturing into completely unknown territory, and learning the best way to navigate in order to ensure survival, oftentimes throwing away societal expectations in the pursuit of something different. As artists, they are comfortable with the discomfort of stepping into the unknown-in other words, becoming audacious. 

“That small percentage of time that people violate the norms, that’s considered audacious and that’s where entrepreneurship lives.”

Marked by Originality and Verve

So what do artists have to do with it?

Breaking norms is encoded in the DNA of many artists. Picasso introduced cubism at a time that painters were focused on recreating reality, Hilma af Klimt developed abstract art at a time when these ideologies were not a thought, and Andy Warhol’s painted soup cans were considered revolutionary. Artists like these started movements and influenced trends for generations after their lifetime, and encouraged people who saw their work to think critically about their world. They needed to be brave enough to go against what mainstream society had already accepted to create new perspectives. 

While there may be mainstream sections that push back against this kind of innovation, the environment surrounding the arts tends to value this way of thinking, and rewards artists who do think this way. Fostering this mindset allows creatives like the ones mentioned to flourish and feel free to continue pushing the boundaries.

However, in business, this traits-originality and boldness-are normally ostracized. While coming up with new ideas is encouraged, they must fit into a predetermined box that is palatable to wide audiences and customers. There is a fear that coloring too far outside the lines can hurt the bottom line, and this fear can hold companies back. 

Entrepreneurs are distinct from business people because of this reason. They have the same audacious DNA as artists in that they know how to start moving outside predetermined lines. It may cause discomfort, but believing in their vision can help them fight for it even harder. Stepping into the wilderness is just the first step, but keeping an audacious mindset makes them the ruler of the jungle.  

Get Jim McKelvey’s new book “The Innovation Stack” or learn more about being an audacious entrepreneur by listening to my interview with Jim McKelvey here.

What can we create together?