Every joke you can make about Portland—from its obsession with artisanal coffee and its ludicrous weekend-brunch lines to its touchy-feely local government and preponderance of Etsy stores—is basically true. Portlandia, in fact, is a documentary. But the same quirks that open up Portland to ridicule have made it something of a haven for small businesses—a city where an odd little company can thrive for decades.

A Biz2Credit study earlier this year listed the Portland, Oregon, area as having the second-highest average revenue in the U.S. for businesses with fewer than 250 employees or under $10 million average revenue. (California’s Riverside–San Bernardino metro area was in first place.) The culture of the city supports and celebrates all things local, small, and handmade, and the economics and politics of the city have warded off cookie-cutter strip malls and big-box plazas. That’s why you see a certain bumper sticker around Portland a lot, on shiny Priuses and rusty VW vans alike: “Keep Portland Weird.”

That bumper sticker is sold from the counter of Music Millennium, an independent record store that’s been open since 1969. Record stores don’t tend to survive anywhere near that long (and a second location of Music Millennium closed in 2007), but the ones that have stuck around in Portland have distinct identities—aspects that can’t be matched via online shopping. Music Millennium hosts an annual Customer Appreciation BBQ; Mississippi Records is an all-vinyl store with its own record label and an in-house art gallery.

It helps that it’s possible to live in Portland on what a record-store clerk makes, and a lot of the city’s eccentricity is the result of its residents’ make-do attitude. In the absence of much major industry, Portland has stayed in a strangely comfortable, low-budget zone for decades. (There’s relatively little conspicuous wealth here, but there’s also not much in the way of conspicuous grinding poverty.) That’s made it the last not-horribly-expensive city on the West Coast. The median rent in Portland last year was $969 a month, or about half what it runs in San Francisco.

The necessity of operating on the cheap has led to one of the city’s most celebrated trends of recent years: To avoid the expense of opening a sit-down restaurant, Portland chefs have resorted to cooking in the tiny food carts that are parked in “pods” all over town, with hyper-specialized menus. (There’s a wildly popular cart downtown that serves Mauritian food, and one of the best-loved Portland carts, Nong’s Khao Man Gai, famously built its business around a single dish, Hainanese chicken and rice.)

Another Portland eatery has figured out a strategy to work with small retail spaces: the burritos-and-smoothies quick-service restaurant Laughing Planet Café has a central “commissary kitchen,” which prepares ingredients for its local satellite branches. Franz Spielvogel bought Laughing Planet from its founder Richard Satnick in 2012; since then, he’s opened Laughing Planet locations in Reno, Nevada, and Bend, Oregon, and has announced his intentions to bring the chain to Boise, Idaho, and Salt Lake City, as well. Satnick, meanwhile, has launched another restaurant of his own: the paleo-diet-focused Dick’s Kitchen, whose initial location is just down the street from the flagship Portland branch of Laughing Planet.

The stereotype of Portlanders as stubbornly independent, caffeine-crazed contrarians is true, too, and not always for the best. (The city recently voted down a proposal to start fluoridating its water.) But our refusal to go along with the crowd also works to the benefit of local businesses: Instead of 7-Eleven, we go to Plaid Pantry; instead of McDonald’s, we go to Burgerville, a fast-food chain that operates on wind power and serves milkshakes and fries made with ingredients from Pacific Northwest farms.

A few years ago, Portland entertained several proposals to develop the Burnside Bridgehead, an underused patch of space right in the center of town. One of the leading candidates planned to put a Home Depot there; the other planned a Lowe’s. Neither plan happened, due to a community outcry demanding that the Portland Development Commission keep the big boxes out. Now what’s in the works for the Bridgehead instead is a set of oddball housing and office spaces, including a pair of buildings covered in wallpaper designs and known as The Fair-Haired Dumbbell.

The cornerstone of downtown Portland business is a big box, in its way, but also a local success story: Powell’s City of Books, a gigantic independent bookstore, founded in 1970, which now occupies an entire city block and spills over into a neighboring building. And even Trader Joe’s, which already operates several branches around town, pulled out of a plan to open a new location in the rapidly gentrifying Alberta neighborhood after the Portland African American Leadership Forum complained that what the area really needed was not a subsidized chain store but more affordable housing.

The easiest jokes to make about Portlanders have to do with our fondness for tree-hugging buzzwords. The one that gets tossed around most often these days, sustainability, isn’t just code for “energy-efficiency,” although that’s the case too. The culture of Portland is to think about the long haul, in business as well as urban planning.

Sometimes those two go together. There’s an urban growth boundary—a “green belt”—around the city to prevent sprawl, encompassing a 20-year supply of land set aside for future development. Combine that with the city’s better-than-decent public transportation and much-better-than-decent bike infrastructure, and it’s relatively easy to get between any two points in Portland; frustrating commutes are rare.

The small businesses that have thrived here are, unsurprisingly, the ones that have planned for the long term with both their staff and the broader community. Dave’s Killer Bread, based in the Portland suburb of Milwaukie, started with 30 employees in 2005 and now sells its organic loaves nationally. Dave’s built up its reputation by showing up at basically every farmer’s market and charitable event that would have them and spreading the inspirational story of how its founder Dave Dahl overcame his criminal past. (One in three of the company’s employees is an ex-con; Dahl himself ran into trouble with the law again last year.) The Milwaukie natural-foods business Bob’s Red Mill is even more generous to its staff: It made headlines in 2010 when founder Bob Moore marked his 81st birthday by giving the entire company to his employees.

Walter Cole is an exemplar of Portland small-business success, a pillar of the community who’s in the Rolodex of every local politician. Because this is Portland, he is also an 84-year-old “female impersonator” (his term). Cole has been operating Portland businesses for more than 50 years—most famously Darcelle XV Showplace, a downtown drag cabaret that he’s run since before the 1969 Stonewall riot, and where his bewigged alter ego Darcelle still hosts six shows a week.

When I asked Cole last year how he’d managed to keep the club afloat for so long, he explained that he’d made sure to befriend its neighbors even in the earliest days, when its neighborhood was Portland’s Skid Row. By the mid-’70s, the Darcelle cast started to get invited to perform at local charity events and fundraisers, and Cole said yes to every opportunity. Cole credits Portland’s open-minded, quirk-embracing culture for making his business sustainable. “In all the 46 years that I’ve been doing this,” he says, “I’ve never been afraid to be somewhere in Portland, Oregon.”