The Secret Life of a Professional Side Hustler - OZY | A Modern Media Company

The Secret Life of a Professional Side Hustler

The Secret Life of a Professional Side Hustler

By James Watkins


This man had a $20k-a-week side hustle, courtesy of the U.S. Mint.

By James Watkins

Chris, age 32, from Chicago [surname withheld on request]

My day is going good. I woke up and I immediately checked the WhatsApp group and other closed forums that I’m a part of. I check them like people read the newspapers. I like to figure out the best way to maximize my credit card points and airline miles and how I can use them to travel where I want to go. I’m a part of these groups where people will talk about pricing errors. Like last week there was a pricing error at a hotel in San Diego, and the presidential suite was pricing out at the regular room rate. I usually start the morning by checking these out so I don’t miss anything — 30 minutes could pass and the deal could be done.

This all started when I was doing study abroad, and I was on a college budget. I started researching travel hacking and getting the most bang for your buck. When I was researching it, some people were talking about getting credit card bonuses. A lot of credit cards have you sign up and you have to spend, say, $5,000 in the first few months. People were like, Well, there’s a way you don’t have to spend the $5,000: The deal was, the U.S. Mint had this mandate to get dollar coins into circulation, and it started selling these coins on its website to consumers to meet its quota. I was like, OK, maybe I could take this a step further; I could just keep ordering these coins on my credit card to build up points. I would simply deposit the coins straight back to my checking account and pay off my credit card bill.

These schemes are called “manufactured spending,” which is focused around racking up credit card charges in cash equivalents.

I would get a big box for $5,000. This is the government for you — they were footing the shipping bill and charging $5,000 even on your credit card. Believe it or not, one of the biggest time constraints of this thing was actually opening up the coins: They came in $25 rolls, and the bank wanted them unrolled. I would spend probably two to three hours opening these coins every day. You’d have to open ’em and take out all the packaging and break them open — it was a whole routine, a full-time job. I would dump them in those 5-pound containers that protein powder comes in. One big jug probably held about eight grand worth of coins. I was trucking multiples of them to the bank two, three times a week, depending on how my ordering was going, dropping off up to $20,000 a week.


I was buying them on hotel credit cards, I was using airline credit cards and I also got into cash back because I got to the point where I had so many airline miles and hotel points that I couldn’t use them as quickly as I was earning them. There was a credit card that had 5 percent cash back for your first six months, so if you’re ordering $20,000 a week, 5 percent cash back every week, you’re not making a crazy amount of money, but more than I’d be making working retail or whatever I would have done back then. The best part is it’s all nontaxable. I never really counted it all up, but I was doing this for more than a year and a half, and I was probably averaging about four or five free flights and getting cash back checks in four figures every month.


UPS delivered boxes containing $5,000 in dollar coins with a hand dolly directly to his door.

Source Courtesy of Chris


I graduated with a music business degree. I’ve never really done a 9-to-5 job. I work six months out of the year helping to throw big festivals like Lollapalooza and stuff, so music is my first love. The rest of the time these schemes are my only source of income. Luckily I keep my costs low — I don’t have any kids, I live alone, I don’t have any school debt. So it works for me. It’s also one of those things where if I want to work more, I know there’s the opportunity out there to make more money if I invest more time in it.

It’s definitely a way of life. All these schemes are called “manufactured spending,” which is focused around racking up credit card charges in cash equivalents, whether it’s gift cards, bullion or whatever. I currently have seven credit cards — a mixture of hotel, airline and cash-back cards. Back when I was ordering coins from the Mint I probably had nine. Another scheme that’s no longer doable is at CVS; they sold these reloadable cards called Vanilla Reload cards. You were able to go to CVS, purchase a card for up to $500 and you could enter this code from the back of the card in a PayPal-type website, and it would put it in an account for making online purchases. The side deal came because there was an option to request to send the money straight back to your bank account. You were spending $5 for the card, but you were getting the benefits from the $500 charge to your credit card. For a long time I would buy five of them every time I was at CVS. But schemes on that scale are harder to come by these days. I wish it was still that easy.


On these forums, we might share an idea before anyone else. It’ll eventually get out there — someone will leak it — but we get to cash in on the deal before it gets shut down. I regularly contribute to two forums, one Reddit group and then there’s a WhatsApp group, which is huge. The WhatsApp group is an invite-only thing, but on Reddit there’s a subreddit called Churning, there’s also an aviation website called FlyerTalk and they have a whole section that’s open to the public on manufactured spending. People start on these public groups, then you get PM’d from someone: Would you like to join this forum; would you like to join this WhatsApp group? You have to prove your worth to get in, show you have something valuable to contribute. It was from the amount of coins I was ordering that people were interested in my process; that’s why I got accepted. That’s why I don’t want my full name used in print — they might not look too kindly on me for spilling the beans.

I’ve heard of people being approached by police when they were buying the Vanilla Reload cards at CVS. So even though the transaction may be totally legal, there’s a lot of social engineering involved in what we do, because whether it’s how you’re dressed or how you approach the person, that’s gonna determine how long the deal’s gonna last, how comfortable they are with the transaction. So that’s another thing we do in the forums — just talk about what works; are you better off doing two separate transactions or one transaction?


I was one of the heavy hitters on the Mint thing, but I wasn’t by any means the only person doing it. I definitely researched that there were no legal ramifications before taking the risk, so I was never nervous. The credit card company loved me because it was getting the processing fees. The only people who didn’t love me was the bank. Chase accepted my coin deposits for about a year and a half, and then eventually it sent me a letter saying it was going to close my checking account. The Mint also eventually said it’s not going to take credit cards anymore, so it caught on. It’s kind of a shame — Chase actually has some great travel credit cards out; it’s been probably about four to five years and it still won’t approve me, so I must be blacklisted somewhere. But it was definitely worth it for the number of free flights and hotels and everything I got out of it. 

It’s a lot of fun; it’s afforded me to visit great places, I get to meet new people and it’s great to work for yourself. The 9-to-5 isn’t for me. I have a lot of critics, and I’m OK with that. Some people just don’t get it, or think I have Peter Pan syndrome and am afraid to grow up. Some people think it’s just a skeezy thing to do. They look at me going on all these trips, when I don’t work a 9-to-5 job regularly, and they think, what’s going on?! The naysayers don’t get me down or get to dictate my life. Ultimately, it’s me I’m on this Earth to please.

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