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12 Best Illegal Side Hustles 2019

Ever since the 2008 financial crisis, most people in the workforce have been working 2 jobs. And let’s face it – some of those second jobs (also known as the “side hustle”) are illegal.

If this shocks you, you’ve probably been living under a rock. Millennials, Generation X-ers, and Baby Boomers are all dipping their toes in the illegal side of the gig economy by not declaring their second income when filing taxes, even when the gigs are perfectly legal.

While we don’t condone making money illegally, we do think there’s something everyone can learn by learning about illegal side hustles. Just try not to be too inspired by this list.

What is a Side Hustle?

In June 2016, Quartz published an article by Catherine Baab-Muguira titled “Millennials Are Obsessed With Side Hustles Because They’re All We’ve Got.”

In it, Baab-Muguira points out side hustles are simply second jobs under a different name. Or, to use her words, “Millennials didn’t invent the second job, they just branded it.”

And she makes a good point. The 2008 financial crisis didn’t create the side hustle.

A minimum wage that isn’t anywhere near being a livable wage simply exacerbates the problem. To quote Baab-Muguira again, “Extra cash is far from the whole story… side hustles are about survival, about being able to afford to live.”

While the job economy isn’t doing too badly on paper, as The Washington Post pointed out back in 2016, getting a decent job – let alone a second job – isn’t exactly easy.

So is it any wonder so many people have turned to illegal side hustles?

Once again, we don’t condone illegal side hustles. But hey…if the shoe fits…

12 Illegal Side Hustles (and Their Off-Shoots)

1. Hacking

Hacking isn’t anything like it is in the movies, but it certainly is a widespread hustle.

To be fair, not all hackers are up to illegal activities: ethical hacking (also known as white hat hacking) is a legitimate career path. But for every ethical hacker, there are at least a dozen black hat hackers.

Hacking takes many different forms. The more common illegal ones will be cropping up elsewhere in our list.

2. Spamming and Spambots

Spam and spam-related malware, such as spambots, have been around for years.

Some spam is just that – spam. But a lot of it also links to scams. So rather than just getting a spam email trying to get you to buy a product or service that pays the sender up to 50% commission, you also end up paying for something you never receive.

Just as common – if not more so – are spambots. Here, you open a link and your computer installs spam malware, such as a DDoS botnet, in the background.

The sender is then able to use your device to conduct Distributed Denial of Service (DDoS) attacks without revealing their own IP address(es). Under threat of a DDoS attack, or in the midst of one, the target is ransomed to pay for a ceasefire.

Alternatively, the spambot is used to build a database of email addresses to direct future spam to.

3. Scam and Fraud

Sometimes linked to spam, but not necessarily always, are acts of scam and fraud. Let’s give each their own consideration:

Scamming Unsuspecting Victims

You get an email or phone call from someone posing as a representative of your bank, or of Microsoft tech support, or even the IRS. After spinning a somewhat convincing story to create a sense of emergency, they elicit payment from you.

What happened here is a scam. But it’s not the only way this happens. There’s also the fake ticket scam, where you’re sold a product or service you never receive.

Then there’s a sweetheart scam, where you meet someone online and they eventually ask you to send some money to help them out with something, often a ticket to visit you.

And then there’s the fake check scam, where someone asks if you’ll let their friend or relative pay for something via check. It’s almost always a big-ticket item, like a secondhand car you’ve listed on Craigslist (the platform’s riddled with scammers).

The friend or relative owes the buyer money, so the check is for more than the selling price. Naturally, the buyer asks if you can wire the balance to them – before your bank notifies you the check is fake, of course.

Insurance Fraud

Insurance fraud is a good one… in fact, have you heard the joke about it?

Three old men are getting to know each other. As the conversation progresses, they get to talking about how they were able to retire and move to Florida.

“There was a terrible accident at my factory,” says the first: “and the whole place burned to the ground. Luckily I had insurance, so I used the money to retire here.”

“Ah, the same happened to me!” says the second. “My store was burned to the ground in an accident, but I too had insurance. That’s why I’m here too.”

“We have the worst luck,” sighs the third. “My factory was flooded. But thankfully, the insurance paid out, so here I am with you guys.”

The first and the second retirees give each other a look before turning back to the third.

“Friend, tell us,” asks the first, “how did you arrange for a flood?”

Not our best joke. But it’s hardly worse than the Insurance Fraud Hall of Fame 2018.

4. Illegal Gambling

Gambling itself isn’t necessarily illegal (depending on how and where you do it). But there are plenty of ways to turn it into an illegal side hustle.

Online Daily Fantasy Sports

Even though it’s become legal in some jurisdictions, plenty of people have noticed you can get rich by hosting your own online daily fantasy sports.

To be fair, it’s not entirely illegal to host them, so long as no bets are being placed. But of course, without the betting, there’s no way to make money off the games.

And if you’re going to go through all the trouble of building a network with specialized software, chances are you’re going to feel the income is owed to you – legal or not.

Sports Betting in Illegal States

With an industry worth around $3 trillion, is it any wonder so many people are pretending to be the Peaky Blinders?

It takes a lot of smart to be able to make any money this way, especially seeing as you’re working with such small margins.

But add the fact you need to consistently beat the house odds and that offshore sportsbooks have pretty much taken over, and it’s no longer such an enticing idea.

Counting Cards

Most of us are familiar with the 1988 movie Rain Man, starring Tom Cruise and Dustin Hoffman. Hoffman’s character, Raymond, is an autistic savant, a fact Cruise’s character Charlie takes advantage of at the casino.

With Raymond’s help counting cards, Charlie beats the house odds a couple of times and increases his fortunes.

That’s not the whole story, of course, and we won’t spoil the rest for you.

Technically, counting cards isn’t really illegal. But it’s heavily frowned upon by the casinos because it takes away their edge, which is close enough.

5. Grow Drugs for Profit

First of all, we’d like to say good luck trying to grow enough poppies for a heroin-based profit. Or coca for cocaine. True, you probably could do it – we mean good luck doing so without getting caught.

Cannabis is another story altogether. We shouldn’t really be putting cannabis in the same category as drugs, but be that as it may, until it’s 100% legal, growing it for distribution is still considered an illicit trade.

Never mind its medicinal purposes, recreational marijuana use is where a lot of the money comes in.

6. Sell Drugs

If you’re growing it, you’re probably selling it anyway.

But we’re talking about the dealers here. Few people are likely to reach the same level as Pablo Escobar, but drug dealers do tend to make a tidy sum of money – usually to fuel their own addictions.

7. Smuggle Drugs

Many, many years ago, actual mules were still being used to smuggle drugs over the border. However, these days, the only drug mules are humans, like Leo Sharp.

If you’ve ever watched Narcos, you probably already know becoming a mule can be very lucrative. But getting caught isn’t so great (just in case you were feeling tempted).

8. Stealing

Stealing is probably one of the oldest ways to make money illegally.

Well, legally too if you believe taxation is theft, but let’s not open that can of worms (follow the link instead). Let’s rather take a look at a few ways enterprising criminals are stealing as a side hustle.

Bank Robbery

Despite the Bonnie and Clyde idealist idea people have of bank robberies, the truth is it’s more like that failed attempt in Big Fish. According to statistics, in 2010 the average bank robbery only yielded $7,500.

That’s a lot of risk for very little reward. You’d be better off doing what Winslow ends up doing in Big Fish – joining Wall Street and robbing people The Wolf of Wall Street style.

Stealing People’s Identity and Selling it on the Dark Web

Ah, identity fraud… when scammers and hackers gain access to your personal information and use it for all sorts of nefarious deeds.

If they’re not siphoning funds out of your bank account to line their own pockets, they’re selling it to someone on the dark web.

It’s worth mentioning it’s legal to access the dark web and there are plenty of legal reasons to be there. Of course, the law indiscriminately treats everyone accessing the dark web as a criminal.

So even if you’re making money in perfectly legal ways, if it involves the dark web, you’re already involved in an illegal side hustle.

Let’s just hope you’re using a VPN if that’s the case.

Burgling Homes

Want to know a scary statistic? Only 13% of the roughly 2.5 million burglaries a year ever get solved. And that includes the ones where the burglar ends up having his ass handed to him by a war veteran, or shot by a gun-toting priest in Texas.

Ransomware

Ransomware is one of the cases we mentioned where hackers use malware to extract money out of their victims.

What happens here, instead of using the threat of a DDoS attack, is the victim’s files are all encrypted. And to get that data back, they need to pay a ransom (hence the name).

Large companies and small businesses are the usual targets here, the 2017 article “Cybercriminals Ignore Individuals, Focus on Holding the Enterprise to Ransom” was overly optimistic.

Embezzlement

Embezzlement has been described as a white-collar crime. Fittingly so – it’s usually the bookkeeper or accountant (wearing a white collared shirt) committing embezzlement.

All it takes is the knowledge of how to “cook the books” by padding numbers so the funds being misappropriated by the embezzler aren’t easily picked up.

It takes craft and patience, with the average embezzler having a clean record before starting in their early 40s and working at it for 4.7 years. And while you may be surprised to hear women are more often guilty than men, it’s men who usually embezzle the most money.

9. Prostitution

The world’s oldest trade, prostitution, is one that has people divided. Some think it ought to remain illegal, while others point out legalization is better for everyone – especially prostitutes themselves.

Wherever you stand on the debate, unless you live in Nevada and work for a licensed brothel or you have a camera rolling, prostitution is an illegal trade.

For some, it’s a side hustle – for others, it’s a full-time job that’s highly dangerous… almost exclusively because it’s illegal, which is the great irony of course.

10. Pimping

Sometimes considered even more lucrative than prostitution, pimping is the trade of managing 5 prostitutes at a time (on average).

Pimps act as an agent by taking care of certain things, like medical expenses, advertising, and providing a location and transport.

Ostensibly, they’re also supposed to provide protection, though if you read the link above on the dangers of prostitution, you’ll see that isn’t always the case. Again, somewhat ironically, facilitated by the law.

11. Selling Pirated or Counterfeit Goods (Copyright Infringement)

Well, with the real-deal Louis Vuitton merchandise costing more than most people earn in a month, is it any wonder there’s a booming trade for counterfeit goods? And it’s expected to become even more lucrative, thanks to the trade war.

That goes for pirated copies of movies, series, and music too. Though the blame here is less on the government’s shoulders and more so on greedy media houses, who make it prohibitively expensive to watch or listen to anything legally.

12. Credit Card Skimming

Now here, we can thank America’s unique and frankly baffling standards. For some reason, we think it’s a good idea to let our wait staff take our credit (or debit) cards out of our sight when we pay the bill.

Do you realize how easy that makes it for them to use a skimming machine to boost their tips without our knowledge? Even worse, it’s ridiculously easy to make the machines too.

In just about every other country, the wait staff brings a portable card reader to the table or asks you to pay in the front by the hostess.

Your card never leaves your sight – and the total you’re charged (tip included) is visible while you’re punching in your pin. The chances of your becoming a victim of card skimming are drastically reduced.

To be fair, it’s not only wait staff (and tipping culture may be to blame for that too). ATMs are another common target.

Conclusion

If we’re honest with ourselves, there’s something deeply wrong with the system when illegal side hustles become the norm just so people can survive.

Thankfully, there are other options. So if you’re feeling strapped for cash and are considering a life of crime, give yourself a chance at these perfectly legal ways to make money instead:

  • How to Make Money Fast
  • How to Make a Million Dollars
  • How to Leave the Rat Race Behind
  • How to Make Money Online
  • How to Make Money Without a Job
  • Residual Income
  • Beginner’s Guide to Investing

And if you’re still considering it…don’t get caught.

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