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Entrepreneurial learning journey: subway artists of New York

November 30, 2015

Well, my final blog post of my entrepreneurial journey, and a second piece about New York.

At 2:35pm on the afternoon of October 27, 1904, New York City Mayor George McClellan took the controls on the inaugural run of the city’s innovative new rapid transit system: the Subway. The first line travelled 9.1 miles through 28 stations.

Running from City Hall in lower Manhattan to Grand Central Terminal in midtown, and then heading west along 42nd Street to Times Square, the line finished by zipping north, all the way to 145th Street and Broadway in Harlem. On opening day, Mayor McClellan so enjoyed his stint as engineer that he stayed at the controls all the way from City Hall to 103rd Street.

At 7p.m. that evening, the Subway opened to the public, and more than 100,000 people paid a nickel each to take their first ride under Manhattan. Today, the system now has 26 lines and 468 stations in operation, runs 24 hours a day, seven days a week. No matter how crowded or dirty, the Subway is one New York City institution few New Yorkers or tourists could do without.

The financiers and engineers who built New York’s subway are justly remembered as pioneers, none more so that Granville T. Woods, a self-educated man who left school at 10 yet held about 35 electrical and mechanical patents when he died in 1910. Woods invented the third-rail power distribution system and the overhead power-pickup system that are still used today.

Another New York subway pioneer was William Steinway, who built Steinway & Sons into the top piano maker in the world. The growth of his business and the need to transport workers from their homes to his factory led to his plan for the city’s first Subway lines.

New York is one of my favourite places to visit. The energy and the vibrancy of life are all very real, but so is its grittiness. The city is a cold smack in the face when you hop onto the Subway for the first time into a churning sea of people, all of whom couldn’t care less about you. The city does not coddle or cuddle, with the unsettling exception of over crowded morning commutes. You have to start your day running or get out of the way of thousands of others who will go right over you. Stark reality pervades the streets, avenues and subways here.

Everywhere you look in NYC today, you see some reference to tech startups or entrepreneurship, and it’s city with a rich heritage of business pioneers. Entrepreneurship is an endeavour that often requires a suspension of reality to clear mind-space for contrarian ideas, possibilities on the edge of their time, and creation of something that has not yet been. The culture and history of NYC provides a great backdrop for this thinking.

Titans of C19th and C20th industry have their buildings dominate the NYC skyline, their omnipresence makes New York the lasting power that it is. They cement a layer of the city in reality for history, whilst also providing a backdrop and frame of reference to those setting out today about making their own mark.

NYC is home to innumerable people and places that talk constantly about APIs, accelerators, host MeetUps, and will ensure you never feel like you’re in a startup snow globe or coffee shop pitching clusterfuck. As an industry, New York startups may someday live long enough and endure enough scars to reach a point of cynicism with new people with new ideas, most of which won’t work. For the now though, you’ll be met with enthusiasm and encouragement from an incredible group of people who want you to win.

The chaotic, hardscrabble, overstuffed, raging, romping, intoxicating, alluring, terrifying melting pot that is New York City inspires. There’s a history of creative disruption here that casts a brilliant shadow down Broadway and the Bowery for more than three centuries, with a host of entrepreneurial endeavours.

Down on the Subway, you come face to face with a different genre of entrepreneurs. At first glance, the street artists crafting a living underground might not look like conventional entrepreneurs, but they use the same core entrepreneurial values and strategy to grow a brand that every successful startup uses.

These people are outside the realm of state responsibility and obligation, individuals charged with taking care of themselves through their own entrepreneurial actions and talent. These artists – musicians, mime actors, painters, jugglers, comedians or raconteurs act as entrepreneurs and brand themselves through their art and personality, as a way be visible in their market and attract customer attention and donations.

The great thing about entrepreneurship is that there are few limitations when you are equipped with the right mind-set. So a laid back hippy mime artist dreamer and a tablet toting spreadsheet loving tech entrepreneur walk into a bar…it doesn’t have to be the start of a joke but the meeting place for a creative teaming experience that can lead to great success and inspiration for all.

We don’t always associate artists with entrepreneurship, but they are as much entrepreneurs as product inventors or app developers. Imagine you are a painter for a moment. In front of you is a blank canvas, sitting desolate on its stand, awaiting your spirit to infuse it with life. Right beside you are your tools. A paintbrush and a palette, with no more colours than a rainbow. It’s a simple set up – but altogether, combined with the human imagination and an ability to execute, has the ingredients to create a unique piece of work with the power to inspire.

What artists do is take an idea and manifest it into reality. They take a vision that existed nowhere else but in their own mind, and actualising it into reality through their work. That’s entrepreneurial thinking.

So what are the entrepreneurial qualities that shape how artists think and behave? Here are traits I saw in the NYC Subway artists that any individual who aspires to make his or her mark on the world should emulate:

Artists are innovators. They yearn for originality and novelty and have an insatiable appetite for finding and creating new connections, for inventing and reinventing, even themselves. Art means changing the meaning of things or creating new meanings. That’s exactly what innovation is all about.

Artists are craftspeople. They think by making and unite the hand and the head, as sociologist Richard Sennett describes it. It has both a physical dimension, exhibiting mastery in craftsmanship, and a meta-physical dimension, connecting a new product, service, or business model with the broader zeitgeist and cultural climate.

They have a USP. Every service, product and brand needs a unique selling point. It is what makes you stand out from the competition and what attracts new customers. The Subway artist accomplishes this by combining amazing art, iconic characters and a mysterious persona. Whilst they had a simplicity and focus on what they did, there was competition for travellers’ attention and dollars, they needed to stand out from the crowd and grab your attention.

Creativity makes for originality. Like artists, startup founders must cultivate creative habits to see the world afresh and create something new. Indeed, the ‘art’ of business has become more important as the ‘science’ grows ubiquitous. As Big Data and analytical tools allow us to make our processes more efficient, intuition and creativity are fast becoming the only differentiating factors.

Passion drives the artists’ work. In fact, their work and life are impossible to separate. That doesn’t mean that startup entrepreneurs need to be workaholics, but they should base their ideas on purpose, vision and beliefs. Innovation is a leap of faith, and innovators need to be believers. Like artists, they will often face rejection, but if an idea is not worth fighting for, it might not have been the right one in the first place.

Spontaneity. By definition, they deal with things that are not measurable and can’t be easily quantified. Innovators, too, should value what may not be easily captured in quantitative terms. Entrepreneurs deal with risk and uncertainty too, so they must be able to tolerate ambiguity.

Demand is uncertain. The Subway artists are working to fulfil a personal artistic vision whilst also seeking to earn a living and a basic economic model. They have chosen their market, yet the demand for their product will lie in the eye of market and the customer. It is down to the artist to find or create their ideal audience in order to create market traction while also remaining true to their artistic sensibilities and personal goals.

The art of possible. Artists can connect dots and take things out of their original context. Likewise, innovators mash up and remix, and embrace new insights and ideas that lead to unexpected, unlikely, and often serendipitous conclusions.

Artists thrive under constraints. The Subway artists had scant resources, had to work within very structured physical formats and yet show ingenuity. In fact, these constraints might even stimulate their creativity. Frugal innovation has become the new hallmark for the art of creating maximum value with minimal resources in business, a genuine parallel.

Artists are great narrators. Each artist told a story with their art but also often tell the story of their art. The same holds true for meaningful innovations. Great innovators design experiences that spark conversations. Just look at ideas funded on Kickstarter, the product is often also the story of the product.

A point to prove. Subway artists, like graffiti artists are a part of an urban subculture of defiance, and usually have a strong sense of what’s going in their core markets and desire for expression – which is why they do the artwork that they do. This determination to make their mark stirs creativity and like an entrepreneur on a mission, gives them energy to prove their point.

This process of dreaming and creating is typically associated with artists, but it is precisely what every entrepreneur does. The late Steve Jobs and Elon Musk are prolific ideators who dream and create, in the same fashion as artists like Banksy and Thom Yorke. These individuals are all luminaries, just that they play different instruments that yield different outputs.

The late Steve Jobs was quoted in his biography as saying, Dylan’s words struck chords of creative thinking when he discussed Steve Wozniak and him bonding over Bob Dylan bootleg albums. Also, don’t forget the calligraphy class that Jobs attended at Reed College, which inspired the famous Mac typefaces and clean design. It is an example of Jobs’ thinking at the intersection of the arts and technology.

Thanks to the rise of computers, the things we make seem to have no bounds. The canvas has given way to the tablet. With resources available online and in the cloud, it is now possible to create something on Tuesday and have it reach millions by Wednesday, as William Deresiewicz said Autonomy, adventure, imagination: entrepreneurship comprehends all this and more for us. The characteristic art form of our age may be the business plan.

Thanks to the Subway artists for showing a buccaneer spirit of entrepreneurship. Some were hugely talented, entertaining and original. As Albert Einstein once said, creativity is intelligence having fun – and it showed.

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