Selling on the Street: The Writer as Hustler

Aaron Gilbreath

While reading a collection of New York Times subway stories called Subwayland, I found the story of Adrian Brune. When the original article came out in 2003, Brune was twenty-seven, a recent graduate of Columbia University’s Graduate School of Journalism, and she was in the Times Square and Grand Central subway stations selling printouts of short memoirs she’d written, for two dollars apiece. “Struggling writer w/ good short stories for sale,” her sign said. In parenthesis: “Master’s from Columbia; bad economy.”

Her technique was simple. She sat on the dirty ground, set a cardboard box filled with stories in front of her, and leaned back against the wall. She did brisk business: over twenty copies of each of her three stories on her best days. “In the space of about two hours,” the Times said, “she had sold more than a dozen stories,” some to repeat customers. One named Orlando Fonseca II liked the story about Brune’s brief romance with a female Columbia student. “It reminded me of some of the stupid things I did,” he told her. He bought her action story, too.

Although Brune settled into her new business, she’d been forced into it. She’d tried for full-time work but could only get intermittent freelance gigs after graduating. Faced with selling her possessions to pay rent or selling her writing, she went down into the subways to try the latter. “She was angry at New York,” the article said, and wanted the city to know it. Yet her situation struck me not as sad but inspiring, and I rarely use the maudlin term ‘inspiring.’

Here was an inventive, enterprising person doing what most of us writers have to increasingly do in the modern publishing world: be our own publicists, accountants, distributors and marketing departments. The subway might seem the domain of the down-and-out, a last resort when normal enterprise fails, but it has always functioned as a de facto supermarket. Brune’s literary pop-up shop fit within a grand tradition of official and unofficial subway food vendors, book venders, shoe-shiners, magazine stands, and people peddling everything from used cellphones to stolen batteries. Why shouldn’t she sell stories like knishes down there? Monetizing writing was the central challenge of our digital era, where newspapers continue collapsing and the expectation and availability of free media continue to eat into print book and magazine sales. She’d figured out a system: short-form narrative, low prices, inexpensive medium, delivered to readers by hand. She controlled the means of production and distribution, and she kept all the profits. Granted, profits were small. She only had two hands. And compared to the covers of certain commercial novels, a stack of paper-clipped pages wasn’t much to look at, but when commuters only had a few minutes to kill on a train, who needed beauty? For once in America, substance trumped appearance. People bought stories for the stories.

Many modern writers tweet to promote recent publications or upcoming events. Some work the Facebook mass-invite circuit to the point of irritation (enough with the invites already; I don’t live near Iowa City), or they get crafty and run contests or mail custom postcards. Brune’s austerity was refreshing. The more I thought about it, the more I realized I could sell stuff on a downtown street, too. Why not?

Portland’s Future Tense Books had just released my first chapbook, A Secondary Landscape. Rather than poetry, the chapbook contained a first-person essay about a roadtrip my best friend and I took through the Pacific Northwest in our twenties, and how it doubled as a search for meaning in a potentially meaningless universe. In addition to that, I would follow Brune’s lead and sell a selection of my essays for two dollars, all printed on plain white paper and stapled together—no frills. Between bills and rent and my own grad school debt, I always needed more money. I loved my part-time job at a local tea shop, and it supported me, but only because I kept a ridiculously low overhead and a tight budget and was accustomed to living without health insurance. Sixty dollars for selling printouts of material I’d already published? Sounded good to me. As the writer Edward Abbey said, give your writing legs: publish and then republish it if you can. Stretch your hard work like last night’s meal, since there’s so little money in writing anyway. The only problem: Portland was no New York.

In New York, Adrian Brune had millions of potential customers streaming by in those narrow subterranean corridors, millions of people whose commute and need to avoid inter-commuter eye-contact created a demand for quick, disposable distractions. Combined with the Port Authority Bus Terminal, the Times Square subway station serviced 62,069,437 passengers in 2012. Grand Central served 42,894,249. If I stood by one of Portland’s busier downtown light rail stations during rush hour, a few hundred people might pass me. None of Portland’s trains traveled underground either, so cagey passengers always had windows to look out of. Those who wanted to read often brought their own material. Then there was the panhandler issue.

Sitting on the street here doesn’t peak pedestrians’ interest. It puts up their guard. Like residents of few other American cities, Portlanders are so routinely bombarded by panhandlers’ requests for money, cigarettes and food that they’d likely rush past my table with their eyes down and defenses up, rather than looking at what I was selling. Despite these strategic challenges, I decided to give it a try.

When I ran the idea past my girlfriend Rebekah, she backed it enthusiastically. “Where are you going to sell?” she said. I threw out vague ideas: on the street outside Powell’s; maybe at a certain busy downtown light rail station. She suggested the monthly First Thursday art walk. “Tons of people go there,” she said. Long-established, filled with pedestrians, spread between downtown and the affluent Pearl District, First Thursday was a crossroads. My eyes lit up at the thought of it. Like so many of Rebekah’s suggestions, this was brilliant. She offered me equipment. “Take my IKEA Lack table,” she said. She kept it next to her oven and stored sauces and tea on it. “It’s light.” It was also dinged and could stand more dinging. They only cost $9.99.

So I started preparing. During the following weeks, I printed out some of my essays, either from PDFs of their final layouts or directly from the literary magazines that published them: essays from the Paris Review, Hobart, Brick, The Rumpus and The Threepenny Review, along with an article about an overlooked Seattle guitarist named Rob Vasquez that I published on my blog. I’d recently found a vintage fold-out chair at a resale shop – gaudy plaid, aluminum legs – for $5. For pricing, I had red plastic numbers and a dollar sign symbol from an old hand-set sign—another score from a resale store.

Now I needed a menu, something to explain who I was and what I was selling. So I took a cardboard mailer from FedEx/Kinkos or whatever they’re calling it now, cut it into a rectangle, and wrote prices and a short bio on the blank side: “Mini-memoirs, music writing and travel stories for sale! New York Times, Paris Review and Tin House magazine writer.” While there, I stapled together essays that I hadn’t even printed at the shop; Rebekah printed them at her office, and I printed some at mine. After I stuffed my essays into Rebekah’s vintage Japanese carryon handbag, I strapped the tiny stool to my backpack and tucked the IKEA table under my arm.

It took fifteen minutes to walk downtown.

Thirteenth Avenue was sparsely populated. A few vendors lined the corridor, and a trickle of pedestrians sauntered between them. On 13th between Hoyt and Irving streets, I set my stuff down in a gap between a man who made earrings and sculptures out of bike parts, and a woman who painted portraits, insects and animals. She had one particularly compelling portrait of man enrobed by an octopus, tentacles coiling around his shoulders and head.

Even though it was clearly available, to be polite, I asked the sculptor if the spot was taken. Since we were going to be neighbors for the next three hours, it was best to be polite. In a barely audible voice the sculptor mumbled, “Talk to her.” He motioned toward a woman standing beside some paintings. A ball cap hid his puffy eyes. “She runs the street.” Runs, I thought, as in, gives permits? Or runs in a less official, more feudal capacity? I didn’t have a permit. I didn’t even know if you needed one, and I’d intended to lay low enough that it wouldn’t matter. This was an experiment, and part of the experiment was seeing if I could sell writing on city streets without officials running me off.

The sculptor looked away, and without a word, I walked over to the woman and asked if I could set up a table to sell chapbooks. “Sure,” she said smiling. She wore jeans and a baggy button-up flannel. She seemed neither official nor feudal, just friendly. “Tell me,” she said, “what’s a chapbook?” I explained and she nodded her head. “Cool, absolutely. Go for it. Good luck.”

I returned to my spot wondering why the sculptor suggested I confirm something so laissez fair with anyone. I decided to ignore him.

With the table set forward on the street, I displayed my chapbooks in the most aesthetically appealing way I could: fanned out inside Rebekah’s vintage luggage. It made a nice display case. Above the chapbooks, I set printouts of the two stories with the most attractive images: the one about the Seattle guitarist, and a photo essay about American thrift stores from Hobart magazine. I stood up my $3 sign, wedged my handwritten menu under the suitcase to anchor it, propped up the suitcase’s lid with my balled jacket, and I sat down behind the table.

Thirty minutes passed without a single customer.

People walked by, but they either looked at my table and kept walking, or they stopped at the two neighboring tables and didn’t glance at mine. Cynicism filled me. The sculptor to my right talked to customer after customer.

The first person who approached me defied all the stereotypes.

Wearing a black peacoat, hip shoes and eyeglasses, he and his young female friend said, “Hi” as he picked up a chapbook. “So,” he said, “what is this?” I said it was a short true story about a Pacific Northwest roadtrip and youthful search for meaning, published by a local press, and it involved PCP. He nodded and returned the book to the case.

His gaze settled on the two printouts. One of them was about guitarist Rob Vasquez. To reel him in I said, “Do you like rock and roll?” I thought that’d be a no-brainer. Anyone under thirty wearing a black peacoat and specs in this town has to like rock and roll. My parents like rock and roll. Mark Twain would’ve liked rock and roll. The category’s so wide that it includes everything from Bad Brains to The Beatles.

“Well,” the guy said quietly, “not really. Kind of.”

Not really? Kind of? It’s just guitar and drums. Who doesn’t like that? I regrouped and kept with the music-theme. “Do you like jazz? I have some jazz stories, too.”

He shrugged and stared at the ground. “Sort of.”

What did he listen to, I wondered, recordings of tropical bird song? Lou Reed’s Metal Machine Music?

I said, “Okay, cool. I have stories about Miles Davis and Coltrane, a travel story about a weird Mississippi motel, family stories, and a meditation on death and a California highway.”

He patted his pants pockets and looked at his friend. “I don’t have any cash on me.”

“Well, keep it in mind,” I said.

It was 6:33pm. I’d arrived at 6.

As they walked off, I texted Rebekah: “this is going to be a bust.”

Conditions weren’t ideal. It was the first art walk of the season, and the weather was windy, overcast and cold, even for April. Despite the climatological challenges, I was still surprised how few vendors there were. As a man told the painter next to me, “There’s usually a hundred fifty artists out here. We have twelve. This thing is packed with people all the way down the street, for two blocks! You can barely walk. This is a bad time. You’ll do great in summer.”

A woman in her late thirties walked over soon after and picked up a chapbook. “Oh,” she said, “those are cute.” Then she put it down and walked over to the sculptor before I could say anything.

I zipped up my coat. A frigid gust blew between buildings, sending everyone’s necks deeper into their collars, and blowing my plastic $3 sign onto the ground. I paper-clipped it to the suitcase to keep it in place.

As the cold rose up through the thin soles of my shoes, other vendors stood at their stations. Some nodded and said hi to passersby. Others sipped hot drinks from steaming cups, or sat on chairs texting. I sat and eavesdropped on the artists beside me.

The sculptor preferred the hard sell. When two women examined his larger pieces, he told them, “I just made that one yesterday.” I didn’t believe him. It sounded like a line.

People passed between the sculptures to my right and the paintings to my left. If they glanced at my table at all, the sight of chapbooks rarely interrupted their conversation. “Joseph’s not like that,” said a young woman to her friend. “He’s—I don’t know what. Not that.”

Here was Lesson #1 of First Thursday: no one gives a shit about your chapbook, at least not this art crowd.

A group of seven well-groomed men stood by the painter to my left, strategizing. “Are we done?” one man said to the others. “Did we do it? Let’s go get a beer.” And they walked south on 13th as a cold wind began to blow. It was 7:12pm. The sun was still up.

I considered leaving right then, just packing up and moving my table to the sidewalk outside Powell’s to capture that literary traffic, the people I considered my people, and a spot where I hoped that, by the grace of some sympathetic god, none of my old Powell’s coworkers would see me.

Then it happened: things picked up.

At 7:13, as the seven men walked toward their beer, I sold a chapbook to a doctor and his teenage daughter. “It looks cool,” he said, and handed her the book.

“Would you like some more music and travel stories, too?” I said. Chapbooks were three dollars. Two printed essays were three dollars. A chapbook and two other pieces of writing were five.

“Sure,” he said. “She likes music.” I gave her the Rob Vasquez piece and an essay from Brick magazine about what Miles Davis’ song “Sid’s Ahead” revealed about the trumpeter’s personality and approach as a bandleader. Then I threw in a few more printouts for free. “Thanks for stopping by,” I said. “I appreciate it.” As they walked away, I slipped the five dollar bill into my wallet and felt glad I’d stayed put.

A correction to the first lesson of First Thursday: some people did give a shit.

Lesson #2: be patient.

Six minutes later, a trippy older guy with silver hair, converse All-Stars and a jean jacket bought a chapbook for three dollars. “I read a lot,” he said. “It’s like an addiction.” When I offered him a few free printouts he declined. “There’s not enough time.” He said he was already reading a biography about Abraham Lincoln by Bill O’Reilly, and a book by Glenn Beck. “You know,” he said, “the talk-radio guy?” I did. “Lincoln freed the slaves not because he was some great guy, though he was. It was politics. Money. It just looks like he was a liberator, but he was protecting himself politically. What do they say: history is written by the victors? Or the spoils go to the victors?” He laughed at his memory. “And it’s still going on today.” As he thumbed through my chapbook, I wanted to snatch it from his hand. Glen Beck. Please. Then he kneeled down beside my table and mentioned how he’d lived in Portland for a year and a half and had been meaning to come to First Thursday more often. “What’s your name?” Aaron, I said, shaking his hand. “Phillip. Nice to meet you, and good luck tonight.” He looked up at the passing clouds. “Hopefully it won’t rain.” Me, too, I said. Rain and paper goods were a bad combination.

After he walked off, I sold three more chapbooks in quick succession: two to a young couple, another to a twenty-something named Rich who worked at Car2go. “I got off work early for once,” he said. “Finally got to come here and walk around.”

It was 7:40pm. I texted Rebekah: “selling some!”

She wrote back: “great to hear baby!”

I scribbled sales in my journal to keep track.

At 7:50, a couple in their early forties came up and started talking. “What’ve you got here?” the man said. Chapbooks, I told them, and first-person stories and essays about everything from music to travel to family relations.

He said, “Cool,” and started flipping through the chapbook. “You made these?”

“Yeah, I wrote the story. A longtime local publisher designed the cover and printed the book. The cover’s a play on those old Blue Note jazz album covers. I’m kind of crazy about them.”

He pointed to the printouts in the suitcase. “And those are your other essays?” He patted his back pocket to check for his wallet. “Why don’t you gimme two essays.” Hearing him say ‘essay’ counteracted my reservations about using the term.

I said, “You bet. Which ones would you like?” I described his options.

“Gimme your two favorites. For five dollars.”

I gave him three: one about my Granddad, one my meditation on death and the California highway, and the article about Rob Vasquez. “I gotta have Vasquez,” he said. “He sounds cool.”

I made a mental note to print more Vasquez pieces next time. The secret history of an unknown local musician proved a compelling subject, even for outwardly suburban types. If anything, between the kid in the peacoat and this man here in his soccer dad clothes, this night proved that you can’t predict a person’s reading habits or musical tastes based on appearances or the venue. I’m thirty-seven years old. I know that intellectually, but by now I should have been better at putting that into practice. It was too easy to lapse into stereotyping. I needed to quit doing that.

The couple introduced themselves as Nikki and Dan. I thanked them and shook their hands. “I appreciate you buying my stuff.”

Dan said, “How long have you been writing?”

“Publishing things since 2006, but daily practice since 2001.”

“Any training? Or just taught yourself?”

“I recently went to grad school,” I said, “but only after I taught myself. When I worked at Powell’s for six years, I woke up every morning before work and wrote for an hour or two or three. It’s the Larry Brown school of writing.” When Nikki asked who Larry Brown was, I told them Brown’s bootstraps story and how he compared writing to brick-laying in a documentary about his life: you practice, and you learn. Then I told them about Adrian Brune and how she inspired me to come here tonight.

Dan said, “You worked at Powell’s? That’s cool. I go in there all the time.” I said I still did, too—a lot actually. Back in the early 2000s, I might have even wrung him up at the register. “Why don’t you give me a chapbook, too,” he said. He handed me a twenty and I handed him seventeen ones. Lesson #3: even if you’re pessimistic about sales, bring change. You don’t want to have to turn down customers just because you can’t break a bill.

People like Nikki and Dan, and the Doctor and his enthusiastic daughter – the whole First Thursday experience – helped clarify what was emerging as my basic logic about writing: get your work into peoples’ hands any way you can. Be generous with the printouts. Distribute the stories and get pages to readers. So sometimes you give more away that you sell, so what. A few bucks don’t matter as much as a few enthusiastic readers. Although that was the same idea that got us writers exploited – with magazine editors often paying low rates or “honorariums” far smaller than the amount of work they have us do (Don’t you need the clips? Don’t you want the cachet of writing for this prestigious magazine?) – it was, when we chose to do it, a wiser long-term strategy. Brune sold stories in the subway for money, but she also knew the necessity of good distribution, knew that writers needed readers, and that not only were we little without them, writing still had value in this world.

Lesson #4: have faith and hang in there. Your fortunes can shift quickly.

* * *

Between customers I pet a dog. Then I pet another. It got so cold and windy that I had to switch into my heavier jacket, which meant I had to prop up my display case with my backpack. It didn’t look as good, but at least I was warmer. Actually, the display never looked good in the first place.

In the silence of lessening traffic, I reflected on the night so far.

Lesson #5: along with the Vasquez article, print more of the Thrift Store essay next time. People like that one. The photos were half the appeal.

Lesson #6: sell cheap. Another cue from Brune that my experience confirmed: if people are going to buy reading material that may end up being unreadable, then it had better be a low-stakes investment. I was selling more merchandise than the painter and sculptor because their wares were a risk and commitment. If mine sucked, customers were only out a few bucks, the price of a coffee or a taco.

* * *

8:18-8:29pm: a man picked up a chapbook and spent the next six straight minutes lecturing and grilling me about everything from the nature of memory, art and meaning, to the reality of bee hive collapse. During his rant, he ran his fingers through his salt-and-pepper hair and spun my chapbook over and over in his hand, frequently pausing to read the text on the back as if it would give him the answers he was searching for, or to see if the words might have changed since the last time he’d read them.

“What is this about?” he said. I told him. “So it’s your fiction?” It’s memoir, I said, so nonfiction. He started at the book, stared at me. Behind his prescription lenses, his eyes bulged in an unsettling way. I can’t even describe most of the things he said during his inquiry, because so little of it made sense. I just sat there in awe while he grilled me.

“Why should I read about your life?” he said, holding up the book. “What makes your story, your experience, worth my time, for me?” He seemed offended by my presence, as if a personal story like the one in my chapbook challenged the value of his and every attendee’s life. When I started to tell him why people might find my story appealing, he resumed talking: “It’s so much about how you are and how we are, that whole put it down to pick it up mentality.”

I didn’t know what he meant, so I tried again to answer his earlier question about why he should care about my story: “Good memoir will show you yourself in the author. It universalizes the personal.”

His tense expression relaxed. “Ah,” he said, and something in his eyes telescoped in and out.

To redirect the conversation and find out about him, I asked if he was selling art here, too.

“No, no,” he said. “I do make things, though. Not this. Not writing, I mean. Or painting. I’m a documentary filmmaker.” Very cool, I said. I loved documentaries. Was he working on anything in particular? “I made a film called <redacted>. I shot it entirely on my iPhone. I came out of this coffee shop, and there was this bee, lying on its back, dying. So I filmed it. Its last bit of life.”

“Interesting,” I said. “I’d like to check it out.” He spelled out the title as I wrote it down on a yellow sticky. It was a play on words. He smiled at the joke. Then he talked and talked and talked some more. Finally he looked away.

“I feel like I’ve taken so much of your time that I should buy a book.”

“I certainly won’t object to that.”

He kept flipping the book over, starting at the text, as if trying to decide what to do or what to pay. “Three dollars?” he said.

“Yes, three dollars.”

“Do you have change?”

“I do.”

He handed me three ones.

Relief washed over me when he finally left. I really earned those three dollars.

* * *

The event ended at 9. The bike part sculptor started packing up at 8:31. From what I could see, he’d only sold one pair of earrings, none of his big pieces. The painter directly across from me hadn’t sold a thing either. I felt bad for him. At least he seemed friendly.

As I shivered, I considered abandoning ship, too. That last interaction was the crown jewel of interactions, and my earnings seemed sufficient evidence of the effectiveness of my experiment, and the brilliance of Adrian Brune’s technique. The crowd thinned further. I’d underdressed. I added up the sales: thirty dollars. Having spent the first thirty minutes thinking the night would be a wash, that was a good haul, especially for so little work. Although the chapbook took me about six months to write, all I had to do was carry some equipment and sit down to sell it. Thirty dollars translated to ten bucks an hour, which was slightly less than what I made at my day job, and half as good as Brune’s best day. Speaking of which, I had to work at the tea shop that coming Saturday. Tomorrow, I was scheduled to talk with my agent about my newest book proposal. Today, I sold chapbooks and printouts on the street. The writing life was a weird one.

My cold toes curled in my shoes. Instead of leaving, I hung in a bit longer. By the time I started packing at 8:56pm, I hadn’t sold anything else, but I had the satisfaction of knowing that I’d worked the entire event. Strangely, I was leaving with more money than vendors who seemed like seasoned pros. Was this proof that reading wasn’t dead? That print media lives on in America? I don’t know, but I now had cash for groceries.

As I stuffed my printouts into Rebekah’s bag, the painter talked to a small group of her friends. They’d come to encourage her and help her pass the time. One guy told her, “You’ll sell something sweetheart, I swear!” He put his hands on her cheeks for comfort. “You’ll do great in summer,” he said. I bet we all will, because we’ll be here, trying.

To make money in writing, likely in any art, you have to hustle. You don’t have to sell on the street, but you can’t write in today’s world without knowing that you do so in the swamp of a shifting publishing landscape. Big changes define our era: the magazine advertising crash of 2007; the numerous shuttered newspapers; The New York Times’ paywall and blogs and restructuring to stay solvent; the shrinking advances of commercial book publishers; and the strengths of the independent press. Brune was just selling writing to make rent, but her efforts mark one front of the literary vanguard, an example of the many ways writers and publishers are experimenting with new techniques, or rekindling old ones, that push publishing in new directions. As scrappy an underdog as I felt on 13th Avenue, I also felt free, felt liberated and empowered. I could do whatever I wanted, all of us could. We just weren’t going to rake in the dough.

While I walked home in the rain with a table under my arm, Adrian Brune was somewhere in Brooklyn. Brune still wrote, though she sold her work to newspapers and magazines rather than in the subways. Since handing out printouts in 2003, she’d written for The New York Times, The Nation, Chicago Tribune, Boston Globe and the Huffington Post. A recent call for sources on Twitter showed her actively hustling: “Working on story,” she wrote: “Looking for a first-hand account of a parent and teen that have experienced the consequences of reckless driving: Anyone?”

Aaron Gilbreath has written essays for The New York Times, Kenyon Review, Paris Review, Brick, Black Warrior Review, The Threepenny Review, AGNI, The Normal School and Hotel Amerika, and articles for Oxford American, Virginia Quarterly Review and Yeti. Future Tense Publishing put out his chabook A Secondary Landscape. He sells tea in Portland, Oregon and lives online at and @AaronGilbreath