The Milanese Leonardo, and Other Tales of Wasted Ambition

The year is 1468. You’re a young artist from a family of hard-working, calloused merchants situated in the Italian city of Padua. While you’re adept in the ways of business and barter, you can’t deny your unfulfilled artistic desires any longer. (Plus, sheep stink and your father’s pretty convinced that soap causes dysentery, so ladies aren’t really your “thing” either.)

You finally muster up the courage to ask for your family’s permission, and they’re totally on board with it. They’ve always been pretty progressive – except for the whole bathing situation.

“But where will you go?” your mother asks.

But really, where will you go?

“Milan!” – read Scenario A.

“Florence!” – read Scenario B.

A) You travel to Milan, struggle to find an artistic footing, wallow in destitute poverty, subsist on rats, then die from eating said rats.

B) You travel to Florence, meet some cool dudes named Leonardo, Botticelli, and Ghirlandaio, paint some seminal work (Flower in a Vase is particularly awesome), and bring fame and fortune to your modest upbringing.

So, what exactly happened here?

In the 15th century, Italy was experiencing a renaissance. But while the term may be used to describe the country at large, each city harbored a particular type of renaissance – a foremost ambition that guided prosperity within that city’s particular region.

This phenomenon, as established by Y Combinator co-founder Paul Graham, is referred to as the Milanese Leonardo. It goes as such: If Milan and Florence had both shared a similar population size and infrastructure, then there would’ve had to have been, statistically, someone with the artistic caliber equal to or greater than that of Leonardo da Vinci situated within Milan during this time period. Yet almost all known artists and artwork alike from the Renaissance stem from Florence, including work by Donatello, Brunelleschi, Ghiberti, the aforementioned, and countless more.

The person who chose to travel to Milan never prospered. This was not because they were any less talented or ambitious than those who flourished under the house that Medici built, but because the ambition of Milan was not aligned with their own aspirations.

Cities aren’t just sinew and cement; they’re hotbeds of underlining ambition that attract and guide their inhabitants toward a specific set of goals.

New York says, “You should make more money.”

Cambridge says, “You should be smarter.”

Silicon Valley says, “You should be more powerful.”

Toronto says, “You should do it for the recognition.”

And people, in turn, follow suit. They become investment bankers, professors, and C-suite technophiles. They create a social structure that rewards those aimed squarely at a foremost ambition while deterring those with a different focus.

Of course, that’s not to say that other ambitions do not exist within the confines of these great cities. It only means that the structures of these cities are most inclined toward a particular achievement. You’re a modern-day matriarch in New York whether you make a billion dollars by founding Uber or from your rich father’s untimely demise, and Silicon Valley wouldn’t care if you drove up to its door in a hydrogen-powered car made out of $100 bills and bioengineered glue if you didn’t also have formula for in-vitro meats or a method for turning feces into drinking water.

Evidence for this is well documented and supported in Graham’s piece; it’s the implications of this information that matter most.

A company is only as good as its people, and in an era of borderless hyper-competition and persistent disruption, choosing the right city for a corporate headquarters or an entrepreneurial pilot program can be the difference between writing a New York Times Bestseller and stopping at Chapter 11.

But a good company extends beyond just the talent pool; it’s cultural chlorine bleeds into both best-in-class retention and motivating employees in meaningful ways. Building an incentive system or corporate hierarchy for those driven by status is a lot different than building one directed at those just looking to pad the back-end of their paycheques.

An arms-length CEO of an established enterprise might proclaim, “If we want to be in Asia, we need to be in Hong Kong,” or, “If we want to be in Europe, we need to be in London” (Or, after the Brexit vote, perhaps Paris or Berlin). And they may be entirely right. Yet, if due diligence isn’t properly performed, you may be in for a tough (and potentially expensive) lesson in cultural politics.

Employees may be quickly enamored with the product you’re selling or the brand story you’re telling, yet when it comes to making a meaningful impact on both the company and the community at large, they may soon succumb to disillusionment and, consequently, another company’s whims.

Of course, no city has “We do it for the praise!” written beneath their population size on an out-of-date highway sign. It’s unrealistic to assume a quick search or online scan can elicit the information necessary to make an informed decision; really, finding this information requires some grassroots investigative exploration.

This investigation goes beyond just visiting a city’s TripAdvisor Top 10 and staying at an overpriced hotel chain; it involves experiencing a city. It’s listening to what people say and how they say it; it’s sitting and watching and learning how people interact with one another and where they congregate; it’s looking beyond the people themselves and looking instead at the city they inhabit – its architecture and art-littered alleys.

It’s both ethnographic and explorative in nature, yet it’s also an essential practice not just for actualized initial success, but also for continued prosperity. Cities change, and ambitions evolve along with them. Paris (as mentioned by Graham) has been an intellectual center, the heart of the impressionist art movement, and a sprawling style haven. Entire countries, like Singapore, have transitioned from colonial outposts to autonomous free economies, and then again to corporate hubs struggling to entice the entrepreneurial spirit.

It’s a myriad of social, political, and infrastructural forces that guide a city’s ambition. People ebb and flow, moving from developed city to emerging outlet, then back again to developed city, driven by like-minded mentalities of status, identity, style, and monetary compensation (to name a few). The waves of social influence create currents that advance and recede based on the opportunities available within a given space.

Do all companies and aspirational individuals alike have to operate within these great cities? No, but it’s much harder to operate within a community that has its priorities elsewhere than to have an audience that not only provides the positive reinforcement to succeed, but that also has the resources required to do so. And that can be a tantalizing proposition to refuse.

Sometimes, though, even with a finger firmly plugged into the light socket of a foreign city, no ambition may be found. But in taking the time to understand that, one can also come to define it. Rust belt revitalization, for example, opens its own doors to a post-industrial renaissance, facilitating a transformation from low-cost manufacturing to high-tech drone factories and aquaponic facilities.

Companies such as Shinola in Detroit and are living proof of the concept, successfully tapping into both a city’s ambition and pre-existing skill set to transform their business and the community within which it operates.

At a glance, ambition may feel like an amorphous concept, one commonly found in 14 pt. Helvetica on an Ivy League application; yet, it’s in the particulars where the most value can be extracted.

So, where to next?

the author

John Wither

John Wither is a creative strategist and writer at Idea Couture. He is based in Toronto, Canada.