1 Hustles | The Billfold


Inexplicably, the man on line ahead of my girlfriend at our local Walgreen’s pharmacy was returning two small packs of Juicy Fruit gum, each with a separate receipt. He was dressed in that combination of Carhartt hoodie and baggy jeans that feels both hip hop and rural, young, skinny, white, and somehow a little bit off—voice too loud, slightly too confrontational.

“A junkie?” I asked when she told me the story, since her description squared with the modest assemblage of heroin addicts who routinely straggle intermittently among the methadone clinic downtown and the shelters, churches, food pantries, and drug spots around our neighborhood.

“He was definitely on something.”

The cashier huffed in annoyance when the young man presented the gum and receipts. He asked, “Is that gonna be a problem? Because I asked the manager,” and here, he gestured toward the back of the store, “and he said it wouldn’t be a problem.” He seemed like he was spoiling for an argument. The cashier shrugged, took the gum and receipts, and gave the man his modest refund.

After he was gone, my girlfriend asked the cashier what it was all about. She explained that it was a frequent occurrence, and somehow involved buying gum with an EBT card at one Walgreen’s and then returning it at another, effectively converting government food assistance into cash, albeit in tiny increments. Just then, the manager came by and the cashier asked whether he had authorized the gum refunds. He had not.

As hustles go, the gum refund scheme strikes me as way more trouble than it’s worth: walking from drugstore to drugstore for a 70-cent payoff seems like a poor return on investment, and most street drugs these days can’t be bought in quantities small enough to cost less than at least five dollars. But perhaps the gum racket was but one of many small-time hustles that our protagonist was working simultaneously as he wandered around Hartford.

There is certainly no shortage of other hustles: a couple weeks ago, a well-dressed man pitched me a story in Dunkin Donuts about having lost his wallet and run out of gas, needing to get to Bridgeport, etc., etc. The next day, apparently not recognizing me, he tried again a few blocks away. “You sold me that bill of goods yesterday!” I said, and he just walked away cursing. At least once every summer, when I’m sitting outside at the neighborhood bar down the block from my building, someone tries to run the out-of-gas hustle with an actual jerry can. I appreciate the extra investment in veracity, but I don’t offer money.

When I was a kid, there were known places around my mom’s neighborhood in Brooklyn where food stamps—which were actual pieces of paper then and not a debit-style card—could be used for non-food purchases, or traded for cash, with the merchant taking a percentage of face value for the risk and trouble. That didn’t strike me as a hustle, exactly—it was just something people did, and I didn’t even understand it to be illegal until much later. Nevertheless, I have always appreciated the little hustles and hook-ups that get people from paycheck to paycheck.

Brooklyn in that era (the pre-hipster, pre-Giuliani era) was in a golden age of small-time hustles. Around July Fourth, old guys from Chinatown would come around selling illegal fireworks to kids on the block. Then some teenagers from the next building went somewhere (Jersey? Staten Island?), bought fireworks in bulk, and drove the Chinese guys off with lower prices. The ice cream truck on our block sold ice cream and weed and harder stuff too. All the bodegas sold loosies (single cigarettes) for a quarter; most sold beer to teenagers; a few sold pre-rolled joints from behind the counter. When I was a teenager, I met some guys from Trinidad who made rum in their basement. Good rum.

My mom was the hustle champ. She would always bake bread or mend clothes for people, usually in exchange for a dime bag or some choice cut of meat, probably nicked from someone’s hotel or restaurant job. In our building, people knew she had beautiful handwriting and would sometimes hire her to address invitations or write notes in greeting cards. She had a knack for finding slightly used things in the trash—shoes, appliances, furniture—and storing them away to spruce up and barter at a later date.

My hustle game was tightest when I was in college. I dated a girl who worked at a gourmet grocery store in TriBeCa who would feign scan all my food before charging me for only the bottle of Snapple that I’d put last on the belt. By the time she left that job, I’d befriended enough of her coworkers that I kept getting free groceries for the next year, and they would tip me off when slightly past-their-prime veggies were getting tossed, and hold them for me at the back of the store.

Around the same time, I worked for Pepe Jeans in their Latin American distribution office, which is actually a real thing. There was a showroom full of clothes from two seasons ahead, and every week or so, one of the handful of businessmen with contracts to manufacture and distribute Pepe Jeans for various Latin American markets would show up to be pampered by us and watch models show off the overpriced streetwear that the elites of Paraguay and Panama would be wearing in six months. The businessmen, perennially tipsy and invariably sketchy (the one from Panama was always accompanied by two new “assistants,” thin, blonde twenty-somethings who appeared to be working a whole other level of hustle), would choose the styles they wanted to manufacture and negotiate the licenses, after they were gone, through a series of faxed letters.

My job was mostly to translate correspondence from the businessmen, answer phones, and run errands, for which I got $9 an hour and a flexible, college-friendly schedule. Then one day, while waiting on some printing job at a copy shop in midtown, I got to shooting the shit with a guy who worked there, a heavyset dude from Brooklyn. “Yo, they got clothing samples where you work?”

“A ton,” I said. “Pepe and Hilfiger.”

“Y’all get to carry them home for yourselves?”

“Sometimes,” I said, and I started to smell business. “They all got a little rip somewhere in them, so when they ship them in from China, we can tell customs they’re not worth anything. Some of them you can’t even find the rip, so those are good, but some got a big slash down the back.”

“But y’all could just carry them whenever?” He was very interested.

“Nah,” I said. “They let us take a few each season, and then maybe we could slide with a few more, but any more that that and I could lose my job.” That was a lie. After all the distributors had made their seasonal visits, the samples just sat in unlocked cabinets until they were cleared out and shredded to make room for the next batch. Employees could take them with impunity.

“Listen,” says the copy shop guy, boxing up my documents. “If you found some Hilfiger jeans with a 40-inch waist that you could carry, and they were from the next season, like not on the street yet, feel me? A hundred bucks.”

“What days you work?” I asked, and thus commenced the best hustle of my young life. That extra $200 a month when I was working and in school allowed me to start building up a modest savings that would prove essential during my lean AmeriCorps year, and again later, when my dad couldn’t afford a suit to wear to my wedding.

In law school, I worked as a house mover, which is really just a job and not a hustle, but my partner in this endeavor had taken hustle to the next level. He was pretty much running game at all hours.

Through bribes and charisma, he had developed relationships with the employees of all the UHaul locations around Boston. This proved crucial on Boston’s big college move-in and move-out weekends. Every UHaul from Providence to Portsmouth would be booked solid, but we could get a job on Friday and pick up a truck Saturday morning. We made a lot of money on those weekends.

My partner would also sometimes do long haul moves. He noticed that round trip truck rentals charged by the mile, but one-ways were priced according to the distance between pick-up and drop-off. So for a run to Raleigh, North Carolina, he booked a truck from Boston to Worcester, drove to Raleigh and back, and had me scoop him up a half hour west of Boston. He made an absurd amount of money from those gigs, and usually came back with fancy appliances and leather couches that people had decided at the last minute not to keep in their new homes. Naturally, my partner knew where to sell those things.

He also used to park his decrepit VW bus on the street near Fenway the morning before a Red Sox game. An hour before game time, he would stand on Longwood Avenue with a cardboard sign offering parking for $2 less than what the lots were charging. He’d lead the first taker to his bus, give up the spot, and drive off to some neighborhood where parking was less coveted. It may not have been the most efficient way to make $15, but it beat chewing gum refunds.

And you, dear readers? What are some hustles and hook-ups that you have seen? What are the ones that you use to get by?

You probably thought I’d let you listen to Jay Z’s “Can’t Knock the Hustle” while sharing your hustle stories in the comments, but that’s just too predictable, plus you’ve definitely heard it before (ditto for “I Just Wanna Love U,” even though Pharell singing “I’m a hustler, baby” on the hook is kind of perfect). Instead, check out “Ice Cream Man,” about an ice cream truck hustle much like the one I remember from my youth. It’s a really solid summer anthem, and it’s by a Hartford rapper (we have some!).


Josh Michtom is a public defender in Hartford, Connecticut. He spends way too much of his spare time decorating his children’s school lunch bags.

Photo: Davidd


28 Comments / Post A Comment

jfruh (#161)

A friend of mine in the Bay Area had what he called the “BART scam” when we were temps living in Berkely and working in San Francisco. BART (the local subway) has distance-based fares assessed by running a card through both when you came in and came out. He arranged it (I think by jumping the turnstyle once) so that he had two “active” cards at the same time, then would alternate adjacent stops at either end each day, with the upshot being that he’d trick the system into thinking he’d only travelled one stop each way instead of across the Bay. This would cut his commuting money in half, which, if you’re making $7 an hour like we did, is no small thing.

Anyway, this distance-based arbitrage reminds me of the U-Haul hustle described here. I don’t even think you could call that a “scam,” since I’m assuming they don’t put any mileage restrictions on you or anything. Pretty brilliant.

zeytin (#4,005)

@jfruh There was another BART scam where you would buy a ticket for 7.90 (it had to be under 8 dollars I think because you could only add fare to tickets under 8 dollars), and cut its magnetic strip into 7 strips which would then be glued onto 7 demagnetized cards. Then each of these would be inserted into the machine to add fare, and after adding 10 cents or whatever 7 new card would be printed with 8 dollars each on them. Loaves and fishes!

Don’t know if this still works or if they’ve prevented this somehow, I haven’t lived in the Bay Area for years.

This piece is delectable, and the Humble jam is the cherry on top.

Firmly believe everyone should have a side hustle at all times. Mine are pretty typical – in high school and college it was mostly babysitting and tutoring. In college I started selling barely used clothes on eBay to support my new-dress-for-each-sorority-formal habit and still do that today, making about $50-$300/month reselling both my items and my friends’ for a 40% cut.

When I was freelancing briefly I did everything from market research to catering gigs, whoever would take me really.

I have a lot of friends that have a side Etsy gig but I have yet to figure out a niche there.

Laurabean (#3,040)

This probably doesn’t count as a hustle (because it doesn’t generate any income) but when I was very poor and still a smoker, I used to just buy zig zag papers and then forage for butts in ashtrays and then empty out the tabacoo and reroll them into new cigarettes. Gross, but cheap! Then I read Orwell’s Down and Out in Paris and London and read about tramps from that era pulling the same trick, so second lesson: there are no new hustles.

laluchita (#2,195)

Dude, everyday I’m hustling. I had a free payphone scam when I was in high school that involved calling a private operator and telling her them that I was having trouble getting a (long distance) call to go through. It worked for about a year before they caught on. I’ve done medical studies and focus groups, and I sell shit on etsy and in craft fairs and teach dabble classes every once in a while. Even though I have a full time job and make more money than ever before in my life ($38K a year) I am always looking for a way to pull in extra cash. I assume I just always will be?

jquick (#3,730)

@laluchita You think $38k/yr is a lot of money?

Aconite (#6,401)

It’s because they didn’t study STEM.

Actually, while we’re talking about STEM I should tell you about something interesting that happened to me yesterday: a man dressed all in rags burst out of the pub and crashed to the ground before my feet, ALMOST DEAD, and also very drunk. I picked him up, dusted him down and as I was about to send him on his way with a handful of small change and a sympathetic smile, he looked me in the eye, clutched my hand with his own filthy claw and whispered, “This is all because I chose Sociology instead of STEM.”

Allison (#4,509)

@jquick she never said it was a lot, just more than she’d made before.

@Aconite A+ comment, would read again

laluchita (#2,195)

@jquick Honestly, yes, yes I do? I don’t have debt, I live in a hip neighborhood, I save for retirement, I eat out, I travel, and I support my mom. Although I wouldn’t mind making more, I definitely don’t *need* to, especially since I don’t plan on having kids.

honey cowl (#1,510)

@Aconite This comment made my life.

garli (#4,150)

In college I worked both as the lone staff member of the Physics Help desk and as a grader for the Physics department. My adviser was the department chair and told me “your hourly rate for grading is shit, put down that it takes you twice as many hours as it does” The Physics help desk was a ghost down unless it was finals or midterms. I’d write down 3 times as much time as it took me to grade and do it while I was manning the help desk. So getting paid 4 times for work I was doing once, or if I ran out of grading getting paid to do my homework.

Hartford is the only place I’ve ever had a person drive up to me and ask for a dollar. No joke. Hartford is seriously the capital city of hustles.

DebtOrAlive (#5,233)

“Inexplicably, the man on line…” Let me stop you right there. “In” line, IN. How quickly one forgets his Oregon heritage.

@DebtOrAlive I don’t forget it – it haunts me, in dreams, in the needling imprecations of my father, and in niggling, idiomatic corrections in online comments sections. I have under my belt five cumulative years in Oregon, six in Massachusetts, seven in Connecticut, seventeen in New York, and one in Argentina, and yet the linguistic specter of the Beaver State pursues me. What is the cost of those five years, I ask you? Must I say “pop” instead of “soda”? Must I wait for the walk sign even when no cars are coming? Where does it end? WHEN WILL I BE FREE?!

Trilby (#191)

My daughter had a good one, back when eBay was still “America’s garage sale.” She’d buy counterfeit handbags from NY street vendors and sell them on eBay as gifts she didn’t need and she’d say she couldn’t guaranty the authenticity. She would also buy designer jeans with tags on eBay and then “return” them to stores without a receipt. She’d at least get store credit, if not a “refund.”

highjump (#39)

The locally owned movie theater that gave me my first job came with the perk of free movies for your immediate family which was hard to fake bc it was a very small town. However there were several people working one shift a pay period just for this perk. So for a time we got one free movie pass (worth $7.50 at the time) per 3 hours worked. Incredibly easy to sell in the halls of my high school or to curry favor. A group of us once got the entire marching band into a movie for free.

We went back to the old system within a year bc the payroll lady hated the free passes thing.

This piece was SO good. I’ve also seen the out-of-gas-style hustle done in NYC with a woman claiming she just got out of eating disorder treatment (incl. food journal) who can’t get in touch with her sister, asking for cab money.

Not new, but I sometimes go to grocery stores and buy just an apple for, like, 50 cents with my debit card and take out cash rather than going to the ATM and paying a fee. Plus I get a snack!

Allison (#4,509)

@Diana Clarke@facebook that is the only way to deal with ATM fees. I did that all through college when I lived out of the range of my home bank.

Meaghano (#529)

in high school we always did that thing where you buy a ticket for the later show, say, 9pm, go see the movie at 7, then afterward go to customer service and ask for a refund, saying you decided you didn’t want to see it. BADASS.

nell (#4,295)

This isn’t exactly a hustle but my boyfriend is in graduate school at a pretty ritzy east coast school, and he accidentally discovered that any time he is making a purchase from the cafeteria all he has to do is momentarily fumble with his debit card and the exasperated undergrad behind him will just swipe their meal card for him. (because when your parents pay for a Cadillac meal plan, you can’t be bothered to stand in line for .5 seconds longer than necessary, I guess) Happens nearly every time.

Liz the Lemur (#3,125)

@nell Sneaking into my college dining hall was pretty easy as well. I would either sneak through the unmanned gate during the rush at dinner (they only had a cashier at one end during dinner) or stash my coat somewhere else and tell the cashier I was coming back from the bathroom.

wallrock (#1,003)

It’s not quite a hustle since I never sell anything, but I’m constantly amazed by the perfectly good stuff my neighbors throw out in my apartment building. Several times a year I’ll find boxes of cleaning products or lamps with functioning CFL bulbs just sitting in the dumpster area. Usually this is around the end of the month when someone is moving out. My sister is a kindergarten teacher and I’ve outfitted her classroom with Rubbermaid storage containers, a Casio keyboard (still in its box), a set of four steel folding chairs, and strings of Christmas lights, all courtesy of my neighbors.

I am so unoriginal and such a rule follower terrified of getting into trouble, none of things ever occurred to me and even if they did, I’d have a heart attack before I could go through with it.

Further confirmation I’d be bad at this – I’ve been trying to sell some dress clothes and nice but still costume-y jewelry for ages and: no dice. Or that’s a comment on my fashion choices. Still.

grog (#2,222)

Good post. What might be interesting for your next post is how you ended up becoming a lawyer with a mom who hustled for dime bags and a dad who couldn’t afford a suit for your wedding.

@grog That WOULD be a good post, but I really don’t know how. Mostly luck and debt, I suppose.

dude (#5,879)

Hmmm, all of the “hustles” I’m aware of really boil down to outright theft from an employer. Bartenders, at least back when I did it and there were no cameras or other spies lurking, were notorious for “juicing” the tip jar (the attitude back then being “fuck ‘em if they are going to make me sell $1 pitchers to broke-ass college kids who don’t tip for shit”). So you’d charge the customer for 4 drinks (after the $1 pitcher special ran out and drinks were full-price), but you’d only ring in 3 out of the 4 drinks, keep a running tab in your head. When you invariably needed more $1′s in your register, you’d pull them from the tip jar (of course) and change them for larger bills in the register, at which point you’d withdraw the value of the $1′s you just exchanged, along with the value of all those drinks you didn’t actually charge for. This bar, btw, may or may not have been in Hartford . . .

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