The city is the most complex machine ever invented. Running optimally the city generates opportunity and provides a platform for interaction, ideas, and improvement. As a concept the city has been iterated-upon, smashed and burnt to the ground, rebuilt, deliberately-designed, haphazardly-organized, and generally resilient for many millennia. But the city is still a human invention and every single one is flawed, many horribly so.

Which makes cities the ultimate problem set. For the engineering-minded and entrepreneurial the challenge of cities has enticed since the first itinerant merchants decided that they were no longer itinerant. Cities for centuries have been the locus of commerce and the crucible of invention (often from necessity). Demographically, they are on a path to be called home to 70% of the world’s population by 2050. If you want a market — or are driven by the moral imperative of figuring out how to get that many people to live in relative harmony — cities are your platform.

And yet some of our most creative problem-solvers — entrepreneurs and technologists who invent the things that have changed our lives radically over the last decade — seem not to grasp what makes cities so dense with opportunity in the first place. There’s a disconnect between the culture of technology companies and what makes for smart urban policy.

Recently SPUR‘s Allison Arieff noted the ways that tech companies have enthusiastically co-opted the language of urbanism — “community”, “the commons”, “town halls”, etc — while not actually embracing any of what that means in the real world. “Why,” she asks, “are tech companies such bad urbanists?”

The answer is that suburbia is in the very DNA of Silicon Valley, which makes it part of the genome of tech culture writ large. Though many of the biggest companies in tech now are less than ten years old, Silicon Valley itself came to be during the boom of late-20th century car culture. (The garage itself is mythical in startup lore.) Anti-density land use, zoning laws that abet sprawl, work-life patterns fashioned around automobile commuting — these traits are as central to Silicon Valley as Stanford, libertarianism and foosball.

Tech headquarters in the Valley (and many other places) are built as simulacra of cities. Corporate campuses sport their own transit systems (some of which venture out into the city itself, altering socio-economics in their path), bike share systems, restaurants, and health clubs. Facebook’s HQ even has a faux downtown, something straight out of a 1980’s shopping mall design handbook. Unlike a mall, though, none of this is open to the public. While “community” may be the buzziest of words in tech parlance, this is community-as-facade, a highly engineered experience that still revolves around automobile commutes and forecloses true serendipity. It would be funny if it weren’t such a problem: For all their embrace of futurism, tech companies in the Valley are merely recapitulating the failures of a bygone age of suburbia.

And yet San Francisco is the preferred place to live for many of these employees. Which is great, except that their salaries — out of synch with the communities in which they live — generate an economic force that skews rents, forces evictions and creates class stratification driven almost entirely by corporations not located in the city. It’s the reverse of a bedroom community. Wealth drives people into cities while keeping the engines of that wealth outside the city.

But this is 2013, not 1960. Today’s tech companies are not stupid. They understand the benefits of the city from a business perspective. (Which is why Amazon, Twitter and Zappos are all building headquarters in the middle of cities.) It is where the talent lives, its many modes of transportation chime with companies’ commitment to the environment and employee health, and cities are very often the conceptual blueprint for social innovation on the web, as Arieff points out. But understanding the benefits of urban life and attempting to create them as self-contained units that simulate a city — as much of middle America did in the latter half of the 20th century with gated subdivisions, office parks, and shopping malls — are two very different things.

Which is more than odd; it’s contradictory. The web itself, fount of so much innovation in the tech world, is the network embodiment of density, diversity and proximity — precisely the characteristics of cities. The sidewalk was the original social network; the corner store the original just-in-time retailer; the town square the original blogging platform. Given this symbiosis one would think more of an effort would be made in tech circles to understand the precepts of urban design.

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So how do we change this? What might we do to set the sights of our smartest technologists towards sustainable urban design?

A start would be to remind tech companies of one of their core principles: user-centered design. Understanding city life means living city life. Not just commuting to it or from it and certainly not believing you understand a person’s situation just because you pass him or her on the street from time to time. The best products are those that begin with a user’s motivation and needs. They are empathetic applications. To crack the nut of urban-scale opportunity — and there is a lot of it, just look at the “sharing economy” successes of Uber, Airbnb, and Zipcar — technology must be built amidst the same forces that create the problems it is trying to solve.

And those problems must be meaningful and relevant to cities, per se. Nine times out of ten the first image in an ad or a presentation on the subject of smart cities will be of a traffic jam — as if congestion were the number one problem facing the city. It’s a very suburban view of what an urban problem is.

Is the self-driving car really what our rapidly-urbanizing world needs? Every single one of our ballooning population in their own hermetic cocoons? That too is a suburban view of the problem, a moonshot to an uninhabitable moon.

Vibrant, safe public spaces; shared, multimodal streets; exemplary education systems that propel people from early childhood through post-secondary; affordable housing — these are the issues that make or break cities. Or, put another way, these are the problems worth solving because they are worth a lot. Yes, in economic terms. Venture capital is all about risk and return. That risk (and potential incredible reward) is splayed out in every city in America.

To read certain of the screeds against the city (and responses to Arieff’s column) you’d think no entrepreneur or developer was having any success tackling urban opportunities. But that’s simply not true. We can build upon the success of the work being done at the intersection of technology and urban design, right now.

For one, the whole realm of social enterprise — for-profit startups that seek to solve real social problems — has a huge overlap with urban issues. Impact Engine in Chicago, for instance, is an accelerator squarely focused on meaningful change and profitable businesses. One of their companies, Civic Artworks, has set as its goal rebalancing the community planning process.

The Code for America Accelerator and Tumml, both located in San Francisco, morph the concept of social innovation into civic/urban innovation. The companies nurtured by CfA and Tumml are filled with technologists and urbanists working together to create profitable businesses. Like WorkHands, a kind of LinkedIn for blue collar trades. Would something like this work outside a city? Maybe. Are its effects outsized and scale-ready in a city? Absolutely. That’s the opportunity in urban innovation.

Scale is what powers the sharing economy and it thrives because of the density and proximity of cities. In fact, shared resources at critical density is one of the only good definitions for what a city is. It’s natural that entrepreneurs have overlaid technology on this basic fact of urban life to amplify its effects. Would TaskRabbit, Hailo or LiquidSpace exist in suburbia? Probably, but their effects would be minuscule and investors would get restless. The city in this regard is the platform upon which sharing economy companies prosper. More importantly, companies like this change the way the city is used. It’s not urban planning, but it is urban (re)design and it makes a difference.

A twist that many in the tech sector who complain about cities often miss is that change in a city is not the same thing as change in city government. Obviously they are deeply intertwined; change is mighty hard when it is done at cross-purposes with government leadership. But it happens all the time. Non-government actors — foundations, non-profits, architecture and urban planning firms, real estate developers, construction companies — contribute massively to the shape and health of our cities.

Often this contribution is powered through policies of open data publication by municipal governments. Open data is the raw material of a city, the vital signs of what has happened there, what is happening right now, and the deep pool of patterns for what might happen next.

Kicked off by data.gov and data.gov.uk, the open data movement has been replicated in most major Western cities. There’s no doubt this data has been put to good use by people and organizations outside of government. Chicago’s ecosystem of “civic hackers”, for instance, is unparalleled, generating hundreds of applications and analyses that make the lives of Chicagoans better. School data, lobbyist data, foreclosure, zoning and land use data, health atlases, snowplow-tracking data, real-time transit data, incarceration data, food-borne illness data — all these sets have been usefully translated into applications that change the way the city is used.

Tech entrepreneurs would do well to look at the organizations and companies capitalizing on this data as the real change agents, not government itself. Even the data in many cases is generated outside government. Citizens often do the most interesting data-gathering, with tools like LocalData. The most exciting thing happening at the intersection of technology and cities today — what really makes them “smart” — is what is happening at the periphery of city government. It’s easy to belly-ache about government and certainly there are administrations that to do not make data public (or shut it down), but tech companies who are truly interested in city change should know that there are plenty of examples of how to start up and do it.

And yet, the somewhat staid world of architecture and urban-scale design presents the most opportunity to a tech community interested in real urban change. While technology obviously plays a role in urban planning — 3D visual design tools like Revit and mapping services like ArcGIS are foundational for all modern firms — data analytics as a serious input to design matters has only been used in specialized (mostly energy efficiency) scenarios. Where are the predictive analytics, the holistic models, the software-as-a-service providers for the brave new world of urban informatics and The Internet of Things? Technologists, it’s our move.

Something’s amiss When some city governments — rarely the vanguard in technological innovation — have more sophisticated tools for data-driven decision-making than the private sector firms who design the city. But some understand the opportunity. Vannevar Technology is working on it, as is Synthicity. There’s plenty of room for the most positive aspects of tech culture to remake the profession of urban planning itself. (Look to NYU’s Center for Urban Science and Progress and the University of Chicago’s Urban Center for Computation and Data for leadership in this space.)

And what about the built things themselves, actual physical architecture? Where is the technology that causes us to rethink our domiciles and places of work, recreation and worship in the ways we’ve remade communications, mobility, and manufacturing in the last decade? Where are the tools that make urban districts as responsive to changing uses as metal and glass have been made malleable by 3D design tools? Where, to put it most like a William Gibson novel, is the “architecture that flickers and buzzes like faulty neon, that is washed with intermittent static like a weak video signal”?

Architect Doris Sung, for example, has begun experimenting with materials that change shape based on external stimuli, much like human skin. And it’s not just materials science, but high technology as well: the increasing instrumentation of cities with sensors and actuators creates a literal platform for designing new experiences. This is what technology startups in particular are good at.

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Scientists have a term called “positive suboptimality” which refers to the resilience of systems which are not specialized for a particular use (or which at least weather changes in external conditions without breaking). Most often this concept is used to describe how nature has evolved not with the fittest organisms but with those fit enough to survive changing conditions. Super-specialization means extinction.

It’s a concept that could usefully be applied to cities. Precisely the way cities fall short of perfection is what gives them resilience and opens up opportunity where none previously existed. What appears broken and yet persists in cities may simply be evidence of fault-tolerance, something all technologists strive for with their products.

Molly Turner nails why this so rubs some technologists the wrong way:

[T]ech innovators also like to work on a tabula raza, void of constraints, preconceived obstacles or even the benefit of institutional knowledge. And while sometimes that leads to genius strokes of ingenuity, other times it means unknowingly repeating mistakes of our urbanist past, such as becoming overly reliant on the wisdom of the crowd or failing to account for important social or cultural divides.

Understanding how cities bend but don’t break, understanding how they do indeed break, and understanding how much of where we live influences the solutions we try to fit to problems are the greatest lessons that tech can take from urbanism.

City officials are often asked “how do you turn this place into the next Silicon Valley”? Most smart folks in economic development answer by saying that they don’t want to. They want their city to capitalize on its own legacy, assets, work ethic and skills. For many years that statement was just politicking and boosterism. But it isn’t anymore. Cities are where the problems exist and where the talent is moving. It’s easy to see how this equation sums and time for tech culture to do the math.