Gill Holland stands on top of his Green Building in NuLu John Nation

Gill Holland pulled off a stunning success in Louisville's East Market area. Now he wants to do it again, across town in Portland.

According to The Saga of Eric the Red, the eponymous Viking explorer called his discovery Greenland to entice his countrymen to settle its barren shore.

Gill Holland, a Louisville developer for whom the moniker is insufficient, employs a parallel PR strategy. He has set up his office on the far side of a waterfront neighborhood here called Portland, where he works out of a repurposed Boys and Girls Club.

When it rains, plaster falls from the ceiling. He is 16 blocks past what Louisvillians sometimes refer to as the "Ninth Street Divide"; 16 blocks past the place where lost drivers drifting west from downtown make panicked U-Turns on one-way streets.

The idea is to give a good name to the most distant quarter of this dilapidated neighborhood. Suddenly, 15th Street doesn't seem so far west—if Gill is at 25th.

Holland, whose background is in film production, embraces the storytelling in urban development. When we speak about Portland, on whose revival he has staked his reputation, he peppers the conversation with bits of local history: the Devonian fossil beds of the Ohio River, Charles Dickens' visit to see the Kentucky Giant, and so on. It was here in Portland, Holland says, that a young Abraham Lincoln—raised in a log cabin 50 miles to the south—first saw human beings bought and sold.

History is part of Portland's appeal to him: "Great stories, great history, great old buildings."

In most cities, talk of exploration, discovery, and settlement in a neighborhood that predates the Civil War would provoke unpleasant accusations. That hasn't been the case in Portland. Its poverty is defined by abandonment and emptiness, not displacement and confrontation.

Unlike most of West Louisville, it is racially diverse and majority white. One in 10 houses is vacant or abandoned; the average home value is $15,500. The median income is $23,000, half the Jefferson County average. More than three in 10 adults don't have a high school diploma; less than one in 20 has a bachelor's. The evaporation of Louisville's manufacturing base—30,000 jobs lost in the 1970s alone—is evident in Portland's empty buildings.

Gentrification isn't a primary concern. Instead, the worry is that outside interest is a passing fad. "Portland and West Louisville have suffered greatly and disproportionately," explains Sam Watkins, the president of the Louisville Central Community Centers, a non-profit that advocates for the area. "They're hopeful it's not just a start and stop — that it will be sustaining."

Holland hopes to raise $23.5 million for his Portland Investment Initiative, which has four components. Two aim to boost the neighborhood's commercial prospects: one focuses on its derelict industrial buildings, the other on its flagging retail corridor. The other two are intended to rehabilitate and expand the neighborhood's stock of shotgun homes. All told, Holland envisions that the number of businesses in the 80-block area will quadruple.

A lawyer by training and a film producer by trade, Holland is not your typical developer. He'd never owned so much as an apartment until he moved here a decade ago with his wife, Louisville native Augusta Brown Holland. (His father-in-law, who died in 2011, had been the chairman of Brown-Forman, the company that makes Jack Daniel's and Southern Comfort.) But the city's worn old neighborhoods inspired him.

His first project was on the opposite side of downtown, in an area then known as Louisville's skid row. Beginning in 2006, he raised $13 million to renovate and rebuild several blocks of East Market Street. The transformation has been, by all accounts, stunning. The neighborhood has acquired a trendy nickname, NuLu ("New Louisville"), and added dozens of businesses and hundreds of jobs.

Holland's Green Building, which opened in 2008, was the first LEED Platinum-certified commercial building in Louisville. The renovated dry-goods store now has office space, a gallery, and a café. (Andrew Hyslop)

The papers here call him the Godfather of NuLu, but Holland reminds me more of a redeemed Bill Murray in Groundhog Day—a handy outsider dashing from one exploit to the next. "He always seems to be finding these tough challenges to overcome," Watkins says.

"He covers a lot of territory: music, art, urban landscape," observes Louisville Mayor Greg Fischer. "I'm a big fan of his."

Holland's methods are sometimes unorthodox. Brooke Vaughn and Jason Pierce had never run a business when they approached Holland four years ago with plans for a café-record store on East Market Street. They were new in town. They didn't have collateral for a loan.

But Holland liked the idea, and offered to sign over the building as collateral. "It was a huge risk on his part," says Vaughn. Her dad did the contracting; the renovation was on a shoestring budget. When the plumbing code requirements changed mid-way, Holland footed the bill.

The NuLu Festival in 2012 (LuAnn Snawder Photography/Flickr)

Today, Please and Thank You, like the rest of the East Market area, is thriving. "Twenty-eight places opened on Market Street within a year of us," Vaughn recalls. "I remember counting them one day and being like, 'Oh my god.'" Like the main drag in an old western town, the street is wide and flanked with low brick buildings full of restaurants, offices, and shops.

Its vibrancy is a symbol of Louisville's gradual evolution into a city that draws creative types from further afield. Between 2007 and 2010, only two other American cities—Chattanooga and New Orleans—recorded a larger increase in the share of jobs located downtown. Aaron Renn, who runs the Urbanophile blog, has remarked that Louisville has much better restaurants than its richer and larger neighbor to the north, Indianapolis. According to 2010 American Community Survey data, more young people with college degrees live near downtown Louisville than in central Indianapolis or Cleveland.

People here say the city, famous for bourbon, horses, and baseball bats, has a special openness. Please and Thank You, Vaughn boasts, teems with "silent introverts doing great things."

"If you can't make it here, you're not trying at all," observes Tim Faulkner, who arrived in Louisville from New Orleans after Hurricane Katrina. After starting his gallery in NuLu (before it was NuLu), he and gallery director Margaret Archambault now run it out of one of Holland's warehouses in Portland.

Portland's warehouses reminded Holland of DUMBO and Tribeca (staci myers/Flickr)
An arts festival last fall at the Tim Faulkner Gallery, located in a Holland-owned warehouse in Portland (Yelp Inc./Flickr)

Portland had been devastated by suspects usual (discriminatory federal housing policy, a highway that severed its connection to downtown) and unusual (two catastrophic floods, in 1937 and 1945). "This is a neighborhood that for 40 years has been ignored by the city,” said Faulkner. “I think the people here just got used to it."

But when Holland turned west for his second act, he came with fresh eyes. Portland's historic building stock gave him flashbacks to DUMBO and Tribeca, areas of New York where the landscape of defunct light industry had evolved into galleries, restaurants, homes, and offices. "The best advantage I had was being an outsider," he says. Like a modern-day de Tocqueville, he thought he saw something Lousvillians had missed: With a little pushing, Portland's blight could be undone.

In Portland, Holland has marshaled some 30 investors in a half-dozen LLCs specific to various projects. Together, they've committed about 10 percent of the $23.5 million Holland thinks it will take to revive the area. Already, though, there are signs of resurgence directly related to those efforts. The area's first independent restaurant will arrive in the spring, along with Vaughn and Pierce's new bakery, Hot Coffee. (Once again, Holland backed the couple's application for a loan.)

Other entrepreneurs have been independently attracted by the same elements. Against the Grain, a local brewery, is expanding its production facilities nearby. "There's something to be said for operating in a space that has character, that has a story to tell," says Sam Cruz, one of the brewery's founders. "That's really what sets us apart from a larger corporate business."

Not everyone believes Holland is capable of a second rags-to-riches neighborhood story. Portland, whatever its potential, can't be DUMBO—because Louisville isn't New York City. It's still one of the most poorly educated big cities in the country, ranking fifth-lowest out of the 51 metropolitan areas with more than a million people. Rents are low, and the central business district is pockmarked with garages and surface parking lots.

A street of shotgun houses in Portland in 2007 (w.marsh/Flickr)

"I'm not buying it, myself," John Gilderbloom, a professor of urban affairs at the University of Louisville, says of Holland's plans for Portland. "I wish him the best, but I think there are problems there that he's not really focusing on." Eight neighborhoods in Louisville have historic preservation status, Gilderbloom says—and Portland isn't one of them.

Banks have shown similar skepticism. Getting a loan to renovate one of Portland's historic shotguns, for example, is nearly impossible without other assets. Even with $70,000 in renovations, a house in this part of town will still be appraised at $35,000. Holland is hoping to renovate dozens of the structures, and get architects to design 12 brand-new, modern interpretations to fill in the area's vacant lots.

Mayor Fischer lauds those efforts. "There's no question he's put more time and attention into Portland than any person in decades."

But even if Holland succeeds in drumming up support for the area, Portland can't be a mirror image of NuLu: It's about 20 times the size.

"That's what excites me most about it," says Faulkner, the gallerist. "It's so big. It's much bigger than one person's vision. Gill's going to spearhead this, no two ways around that. But this is the largest neighborhood in the whole city."

Correction: This article originally stated that Holland intends to quadruple the number of jobs in Portland; in fact, he hopes to quadruple the number of businesses.

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