49-57. Urban Outfitters

We invited nine folks who are remaking city living to squish into a Manhattan dinner party. The mission: Apply their collective creativity to envision the future of the metropolis.


The tour begins in Graham Hill’s living room. “This is my apartment,” he says. “The prototype.” It’s a mostly empty space, white on white, with a modernist couch, a classroom globe, a stack of hardcover books, and an acoustic guitar hanging on the far wall. The nucleus of most American homes, the television set, is absent. Instead, Hill’s architects, two Romanian graduate students he found on the Internet, designed cabinets that hide a digital projector, a rollout screen, and an Apple TV. Invisible high-end loudspeakers have been plastered into the ceiling. “I crowdsourced the design,” he says with pride, as we quickly pop into his bedroom. “I started with a really aggressive brief: Enough room for a couple. The ability to work at home, have guests over in a civil manner, a sit-down dinner for 12.”


Hill, soft-spoken and scruffily handsome, gives the tour with the easygoing manner that comes from having worked as a TV host–and from having done this hundreds of times. In 2010, the 42-year-old entrepreneur launched LifeEdited, a socially conscious real estate startup. We’re standing in the company’s first project: this home, which is also its headquarters.

“The tour,” as even Hill calls it, is a deliberately misleading way of describing this experience. We never actually move. His apartment, a single 420-square-foot room in an old tenement building, does the moving. Hill transforms his couch into a bed, makes a desk appear from the wall, and then moves that entire wall to reveal a guest bedroom. Just as quickly, he disappears the guest room, pops a Murphy bed back into place, and reveals a dining room table with seating for 10. Even Hill’s bathroom is multifunctional: He soundproofed the toilet stall and added a handsome wooden bench that folds over the seat, which turns it either into a private phone booth or, no joke, a very tiny meditation studio.

This might be a slightly crazy way to live, especially when you consider that Hill sold his last company, the green news site TreeHugger, to Discovery Communications for $10 million. But Hill is living his mission: He’s part of an evolving cohort of researchers, techies, entrepreneurs, and artists who see cities as laboratories for the future. “One of the easiest ways to go green is to go small,” Hill says. “I want to show people that there’s an amazing modern green future, and make it easy for them to step into it.”

He brags about having given away nearly all of his books, furniture, and DVDs. He owns 10 dress shirts and four pairs of pants, three kitchen knives, an iMac, an iPhone, and not much else. He says he’s never been happier. Hill is currently in talks with developers in several cities, and, to bring others on board, he throws dinner parties here more or less nonstop. In doing so, he’s turned his apartment into a microcosm of the idealized city: a dense area of self-selected creative types, who all improve together. So Fast Company took advantage, playing cohost with Hill and stuffing it with eight other iconoclastic urbanists from different disciplines. The question of the night: Can we create, on this small scale, what these people hope to create on a large one?

The food is a hopeful sign. Our chef is Sarah Simmons, a 36-year-old former marketing consultant and the founder of City Grit, a restaurant only nine blocks from Hill’s apartment. She makes a mean beef short rib–but given Hill’s tiny kitchen, which has a shoebox oven, she has to ditch her usual ways. She can’t make the grits she normally pairs with those short ribs, so she prepares simple white rice in an electric cooker and then douses it in a mix of butter and pureed sea urchin. Then she serves everything in space-friendly bento boxes with a selection of noodles, greens, and other Japanese dishes.


“It’s kind of like a metaphor for this apartment,” remarks James Freeman, founder of Blue Bottle Coffee, one of our dinner companions. “A beautiful, shiny box with all these divisions.”

This is how creativity in cities tends to happen: Con-straints become opportunities. City Grit itself is a case in point. Unable to cover the rent in New York’s Nolita neighborhood, Simmons partnered with WRK, an interior design firm that uses the restaurant as a showroom. Seven evenings or so a month, Simmons, who is originally from North Carolina, serves Southern-inspired cuisine. On other nights, she hosts guest chefs–generally hotshots from smaller cities looking for exposure. City Grit customers buy a ticket in advance online, usually paying $45 and up for a set tasting menu. Dinners generally sell out.

The model, as Simmons freely admits, is a hack. She gets lower rent and loaner furniture; her pay-in-advance model reduces risk; and she collects fees from the guest chefs. But these tricks also make City Grit one of the most interesting places to eat in New York; meals typically end with guests bonding across the long communal tables. “It’s really important to me that people make friends at the dinners,” Simmons tells us as we start to eat. “Food brings people together, but not if they’re sitting at two-tops,” those restaurant-style tables for two.

It’s not just food, though. “You said we were all thinking about cities,” says Julie Keefe, looking at me and addressing the evening’s premise. “But what we’re all thinking about is community.” She was appointed Portland, Oregon’s creative laureate last year for Hello Neighbor, a public art project created to address the anxieties around gentrification in her North Portland neighborhood. And she’s zeroing in on the primary potential of cities. “Community” in the suburbs generally means knowing your neighbors and having enough property for a garden party. In contrast, communities in cities are dynamic: City dwellers never know all their neighbors, which forces them to constantly form new, at times fleeting, bonds. Yes, this can make urban life lonely, even scary, but it’s never dull. It can lead to new ideas and even dramatic changes to the physical landscape.

“I remember a couple of years after we opened, I saw a real estate flier that said, ‘Steps to Blue Bottle coffee,'” says Freeman, of the coffee shop. “I was like, Holy crap, we’re an amenity.” His business has shown the power of that ever-shifting community. He opened his first shop in a 250-square-foot space on what he describes as a pee-smelling, dead-end alleyway called Linden Street in San Francisco’s Hayes Valley. “At the time, the things you could buy most easily there were haircuts or heroin or $400 blue jeans,” he says. But the space was all he could afford.


Cities’ high cost of living can be a deterrent, but Freeman’s story reveals an unintended benefit: Newcomers are forced into new territory, creating a constant improvement of space. That first cafe, which he opened in 2005, was so small that there was no seating–or even indoor space. Customers drank their lattes on the sidewalk, which turned it into a sort of open-air cafe. Today, Linden Street is among San Francisco’s hippest (and least pee-smelling) blocks, and the kiosk earns about $6,000 per square foot per year, a figure that beats pretty much every retail chain except for Apple.

The company now owns 11 cafes, most of them tucked into other urban nooks. It generates more than $15 million a year in revenue. Freeman recently closed a $20 million round of venture financing to expand his model. “That’s what happens when you bring businesses back to neighborhoods that are disenfranchised,” says Keefe.

For urban pioneers, transitional neighborhoods are fertile ground. “There are these pockets of geography, where you get cross-pollination from different communities,” says Elizabeth Stewart, cofounder of Hub LA, a coworking space and membership club in Los Angeles’s fast-gentrifying Arts District. It’s bordered by a half-dozen ethnic enclaves, and Stewart makes the proximity a selling point. Within the first six months of opening, three members have been hired by other members and two new companies have been founded and spun out. “The vision,” she says, “is to help people find the resources and relationships to move their ideas forward.”

This shared vision of bento-box living may seem radical, but the group’s successes speak to the potency of urban density. It is, in that sense, a glimpse of the future. Roughly half of the world’s population now lives in urban areas; by 2030 the figure will be close to 60%. Here in the U.S., cities are now growing faster than suburbs, which hasn’t happened since the 1920s. In March, New York mayor Michael Bloomberg announced that more people are moving into the nation’s most populous city than moving out for the first time in 60 years.

“One of the areas where I think we’ve gone wrong as a society,” Hill says, “is that we’ve developed this thing where what you want to aim for is your own castle, gated away from everyone–and even within that castle, lots of space.” Environmental pressures, rising fuel prices, population growth, and an economy in which roughly 80% of the jobs are in the service sector (and, therefore, in urban centers) makes the 20th-century white-picket-fence ideal almost an anachronism. “Younger people are looking at the suburbs and saying, ‘I don’t want that life,'” says Vishaan Chakrabarti, a professor of real estate development at Columbia University and the author of A Country of Cities. “What happened between World War II and today was a blip.”


The trend is stoking a new entrepreneurial urbanism. Venture capital dollars have migrated from the suburbs of Boston’s Route 128 corridor and the office parks of Silicon Valley to the urban cores of New York and San Francisco. In Las Vegas, Tony Hsieh’s decision in 2011 to relocate Zappos from a suburban corporate campus to a part of downtown that had largely deteriorated into a collection of vacant lots and check-cashing stores has prompted dozens of companies to follow (including LifeEdited, which is building three experimental trailer-apartments there).

Startups such as Airbnb, Uber, Yelp, and Zipcar are commanding valuations in the hundreds of millions by catering to young, tech-savvy city dwellers. When Hill’s guests come to his dinners, they often arrive by Uber and eat a meal prepared by a chef Hill finds on Feastly, a sort of Airbnb for dinner parties. Cleanup is handled by the on-demand labor service TaskRabbit.

The group’s shared beliefs began to splinter when the conversation turned to another disruptive city-focused techie. Apoorva Mehta is the CEO of Instacart, a nearly year-old grocery delivery service that has already raised $2.3 million. For just $4 plus tip–roughly the price of a cup of Blue Bottle’s finest drip–Instacart customers can order food online from a handful of grocery stores, including Trader Joe’s and Whole Foods, and send a “personal shopper” (that is to say, a delivery guy) to bring it to their door in three hours or less. Urban food-delivery startups are nothing new–Webvan and managed to burn half a billion dotcom dollars between them before going bust in 2001–but Mehta’s company takes advantage of two peculiar things about cities in 2013: the ubiquity of smartphones and persistently high underemployment. Instacart’s personal shoppers are independent contractors paid on commission. The average wage is between $12 and $15 an hour. The contractors use their own mobile devices and vehicles.

“This is absolutely fascinating,” says Robert Reffkin, an investment banker turned startup guy, who’s been mostly silent tonight. “But what worries me is going to a world where there aren’t people with health care and retirement savings.”

By which he means: Mehta’s company isn’t creating good jobs. Mehta smiles. It seems like he’s deflected this criticism before. “These are people who didn’t have jobs before,” he says. “They are students, stay-at-home moms, people who love shopping.” He provides them some income.


Reffkin isn’t buying it.

“It is socially unsustainable,” he says, shaking his head. Reffkin may be an unlikely person to make this argument, having spent nearly a decade in corporate finance–but he was an unlikely banker too. His father, a San Francisco jazz musician with a drug problem, left the family when Reffkin was a toddler. Reffkin’s mother, an Israeli immigrant who was disowned by her parents when she had a mixed-race baby, raised him by herself. He got a scholarship to a prestigious San Francisco prep school, graduated from Columbia University in two years, was hired as the youngest McKinsey analyst in the firm’s history, and eventually became chief of staff to Goldman Sachs COO Gary Cohn.

Today, Reffkin is working on an online real estate search startup, Urban Compass. In his spare time, he helped found a charter school in the Bronx and launched a not-for-profit, New York Needs You, which finds mentors for students who are the first in their families to go to college. Reffkin, who hopes to run for office in New York someday, tells us that government programs may be the only way out. “The greatest impact on cities is from government, whether it’s transportation, health care, sanitation, or crime,” he says. “If our cities are going to succeed, we need to bring innovation to the government sector.”

On its face, this isn’t an offensive idea to these free-market dreamers, but the question of how cities should evolve–organically or via government–adds frisson to the evening’s bonhomie. Cities require efficient infrastructure–subways, sewers, constant repair of overused roads–and infrastructure means jobs. Reffkin wants more than that. He wants creativity that spawns new industries and enriches lives.

Others around the table begin offering up their own dream interventions. Denise Hoffman Brandt, a landscape architect, suggests that cities should stop planting street trees and maintaining grass-covered lawns, which require continual upkeep and huge quantities of chemical fertilizer. Sandra Richter, a fellow at MIT’s Media Lab, reminds us that even well-intentioned government initiatives can have unintended consequences: “I’m totally against bike helmets,” she says.


It’s a show-stopper of a statement. But last year, as part of an MIT research project, she interviewed New Yorkers to figure out why commuters didn’t ride bikes. Fear of injury turned out to be the single biggest factor. She concluded that a greater emphasis on cycling in pairs would make people feel safer, thus reducing car traffic and pollution. Mandates on bike helmets, on the other hand, would not. It sounds reckless, but a laissez-faire approach to helmets has worked in places such as Dublin and Mexico City. Meanwhile, the unpopularity of Melbourne, Australia’s bike-sharing system has been frequently blamed on the city’s helmet laws. “If you’re wearing a helmet, you’re in more danger,” she says, citing research that has shown that drivers are less likely to hit bareheaded cyclists, apparently because they give them a wider berth than those who wear helmets. “The question is, how do you make sustainable sexy,” Richter says. “If you wear a stupid helmet, you’re not going to feel sexy.”

Nobody buys it.

“I speak from experience,” says Keefe, the Portland artist. “I was in a serious bike accident with my daughter, and helmets saved us.” The best thing about arguing over food is that, when all else fails, you can just praise the dish in front of you. “This is amazing,” says Brandt, looking at Simmons. We all agree.

The theoretical physicist Geoffrey West has found that if a place’s size doubles, all measures of its productivity–per-capita income, the number of patents per person–increase by 15%. A denser city means more people talking to one another on the street, in subway cars, and over dinners like this one. These spontaneous interactions are what lead to innovation, and they are why cities have produced most of our great ideas, works of art, and wealth.

“I’d love to be able to force more dialogues like this,” Reffkin says. “There’s so much more richness that we could all enjoy.”


Because when people get to know each other, they start working with each other. It begins with idea exchanges: Brandt suggests that Mehta’s grocery delivery network could be expanded as a way to alleviate traffic. Stewart says that clubs like Hub LA may be able to offer health benefits to contractors. Hill jokingly offers a way out of the helmet argument: Helmets with wigs attached to them, providing a sexy look and a protective shell. We drink more wine.

Soon deals are on the table. Simmons asks Freeman if he’d come by City Grit to check out her restaurant. She’d love to carry Blue Bottle Coffee, or even, she suggests, host an entire Blue Bottle cafe. He says he’s open to it. While this exchange is happening, Reffkin asks Stewart if she would consider moving to New York to work at Urban Compass. Several people agree to meet for drinks or coffee the following day.

I stick around to help Hill clean up and convert the dining room back to his bedroom. Hill folds the table back into its original, tiny form and stashes it under the counter. I shake his hand and start to leave. “Listen,” he says. “If you ever want to do this again, we can. Anytime. We get a TaskRabbit to clean, get somebody to bring in food, and get 10 people in here, or even 12. It’d be almost no work. It’d be a great night.” Because if this apartment is empty, what’s its point?

[Photos by Brett Beyer]