Venice(Bridge of Sighs)

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What does it take to be a great artist?

Richard Russo evokes this question near the end of his 2007 novel, Bridge of Sighs. In it, he chronicles Lou Lynch, Jr. (Lucy) and his friend Bobby Marconi, who grew up together in a small town in upstate New York. The two friends couldn't be more different. In sixty years, Lucy has never left his hometown, but Bobby on the other hand, leaves as soon as he graduates high school, fleeing Thomaston never to return. He eventually becomes a world-famous artist and lives the rest of his life in Venice. After Bobby passes away, a reporter interviews Lucy to learn more about his friend's childhood.

On Saturdays, the two friends took turns surfing in the back of Lou Sr.'s milk truck. The thrill came when the truck, turning unexpectedly, caused one or the other to lose his balance and crash into the side.  Unlike Lucy, who braced himself before turns, Bobby let go and even shut his eyes. In Lucy's words, "Bobby wanted what was coming down the road to be a surprise, even if it meant he got hurt."

In my previous post, I explained that entrepreneurs are similar to artists because they're outsiders. In my opinion, Bobby's behavior represents a willingness to be vulnerable, another trait that entrepreneurs and artists have in common.

Anthony Tjan, founder of the VC firm Cue Ball, calls vulnerability the defining trait of great entrepreneurs. He describes it this way:

Active vulnerability comes from engaging in a contemplated risk that considers and hopes for the payoff, financial or otherwise, that will be worth the effort. Active vulnerability is in essence proactive and informed risk-taking.

I describe entrepreneurial vulnerability differently.

An entrepreneur's work, like that of an artist, is a form of self-expression. When painting, an artist injects her canvas with her beliefs and values -- knowingly or unknowingly -- and the completed painting becomes an extension of herself. Likewise, when an entrepreneur founds a company, she imbues it with her opinion of how the world ought to be. It, too, springs from her deepest yearnings, making it unique and personal. There is no guarantee that the audience or market will accept her work. Vulnerability, then, is the willingness to reveal one's true self and risk misunderstanding, ridicule, and even rejection.

At the core of human experience is a longing to be accepted. Some people, to satisfy this innate desire, conform to the norms around them, but in the process, compromise a part of themselves. Other people, the misfits, resist the temptation to fit in and remain true to themselves. As exhausting and demoralizing as it can be, the misfits' willingness to defy norms gives life its nuance and beauty.

Dan Pallotta explains where this strength comes from:


The greatest artists, entrepreneurs, and leaders don't seek acceptance. Instead, their love and compassion fuel a yearning to make a ding in the universe and persevere despite rejection.