Below are the Top 10 legal side business that can make you $1000-$2000 a week. This list is based on my own experience and research. I have tried most of them and it takes dedication and passion to get there. Do your due diligence and make sure you have enough passion and patience to make it work.
Become an amateur team sports referee and officiate about 20 to 30 games per week. I did it myself and it works. You make extra cash and stay in shape and meet a lot of people( hot girls playing soccer or basketball included).
To become a soccer referee, you just need to take a 2 days certification that will cost you about $100 depending on your state.
Amateur soccer Referees are paid up to $50 per game and games are played everyday after 05pm and on week ends.
I have created a referee locator app and listed how to become a referee anywhere in US and Canada at Amateur Referees Locator – How to become a referee? – Djamga – ShowUpAndPlaySports
2- Buy and sell popular or efficient cars (Japanese makes like Corolla, Camry, Honda, etc…) on Craigslist , kijiji, facebook marketplace or any local popular online used item market site.
3- Learn web design, coding and apply for part time consulting gigs at Remote Jobs: Design, Programming, Rails, Executive, Marketing, Copywriting, and more. or any other site posting IT work remote jobs in US or Canada.
4- Organize sports tournaments (soccer, basketball, hockey): Rent good and inexpensive fields, convince friends to create teams, run a great campaign and organize amateur sport tournaments monthly and you can easily make $5000 after expenses if you do it right. This is not easy though, you must know local players and team captains and convince them to join.
5- Become a freelancer writerIf you’re creative about how you write (hint: use speech to text and edit down into prose) you can get your hourly > $40/hour even at rates like $1/100 words.
6- Learn to play poker either online or in-person. Online, go for low-stakes and grind out your cash. Live, go for higher stakes and hunt down atrocious players (see my answer to How much can a competitive online poker player make? for more)
7- Become a tutor that focuses on students that are under-performing in the subjects you’re best at.
8- Do contract sales for companies that pay you recurring revenue. Over time, if you take care of your accounts, you won’t even need to close new ones if the retention rate is high.
10- Arbitrage textbooks on Amazon. Time it with quarters / semesters / school years ending and hold until next quarter / semester / school year.
Bonus2- Buy vending machines so that your cashflow for your investment is $1,000-$2,000 a week
Bonus- More opportunities here