1. The Couch Diver
I was a couch-cushion money-hunting fiend. And not just my house — any house we would visit I would root through all of the furniture looking for change. I was obsessed. I also used to steal change out of fountains. Like handfuls.
2. The Wedding Crasher
At large weddings and family reunions, my dad would put a sign on my adorable little 2-year-old sister asking for money. She'd run around in her cute frock with her little gold ringlets flopping around on her head and come back with a fortune. Youngest hustla in the biz!
3. A Flippin' Awesome Business Plan
In fifth grade I made little flip books — the things where you flip through the pages and a little cartoon animates. I got in a real groove of making flip books and figured that my peers would pay me for them. So I came up with a pricing structure — $1 for my standard model and $2 for my premium model. My teacher found out that I was pushing product and put an end to it, but I continued to sell them on the black market (whispering on the bean bags) — a crime I justified by severely slashing the prices: 5 cents for standard and 10 for premium. I made somewhere around 45 cents."
4. A Classic!
Like any kid, I had a lemonade stand with my sister. Our main source of income was from my father. I will say that now whenever I see a lemonade stand I always stop. You always have to stop!
5. Sisterly Love Pays
My sister Abby used to charge my sister Kimmy money to come into her room. She would start by saying it was a quarter, and then when Kimmy went back to get a quarter from her piggy bank and returned, she would say she had upped the price to 50 cents. And she would keep upping it. I'm not sure how many coins she was able to get out of this game, but I'm sure my parents made her return them.
6. The Internet Before the Internet
I didn't actually make money from this, but I PLANNED to become rich.
I collected business cards. I had thousands of them, and I kept them in those cute little boxes where you're supposed to store recipe cards or something. Whenever my family went anywhere, I would ask for a business card or take one if I saw it on the counter. I believed that, eventually, I would be able to create a business by having so much information! I thought that if people wanted, say, a haircut in a certain town, they could call me and I would look through all my business cards and tell them where they could get a haircut.
I aspired to be the yellow pages, which already existed at the time and would soon become entirely pointless with the dawn of the World Wide Web.
7. The Middle School Black Market
Gum wasn't allowed in school, but I had my aunt buy these yummy sour gum balls in bulk. Then I'd take a pocketful of those bad boys to school and deal them on the playground for a quarter a piece (or 3 for 50 cents). I only brought a certain amount to school every day to create demand. I always sold on the DL and NEVER in class (that's how you get caught).
At one point, another kid tried to steal my game and started selling his own gum balls, so I engaged in a small-scale gum dealer turf war and "ran him out of town" by flooding the market discounted prices that his newly formed gum ball enterprise could not sustain. He and I established territories which I immediately violated, giving his customers better prices, more consistent supply, and an overall more gratifying customer experience.
Then the school started investigating the underground gum trade, so I stole the kid's photo from the "Student of the Month" board, snuck into the teacher's lounge, and printed out a bunch of "gum for sale" flyers that I put up in the bathroom with his name and photo on it. It almost got him expelled. He then tried to out me as a seller, but I was always one step ahead of him. I lay low for a couple of weeks, then I was back in the game.
Over four months, I made about $450, which is a LOT for a sixth grader. I wish I could say I used the money for something useful, but I just bought video games with it.
8. A Fair(l)y Simple Request
After getting $1 from the Tooth Fairy a couple of times in a row, I wrote a note to her that I placed under my pillow with my next tooth that requested both $100 and for her to paint my room green. Perhaps it was my only-child selfishness or skepticism in the Tooth Fairy or both, but needless to say, she was unable to deliver on either request.
9. A Great Sale!
When my sister was about 7 years old, she used to collect a bunch of things from around the house, set up a table in our driveway, and try to hold her own impromptu rummage sales. This wasn't stuff we wanted to get rid of, and she was willing to take 50 cents for my mom's nice jackets, artwork, etc. Luckily, we always caught her before things got too crazy.
10. The Clean-up Crew
When I was 7, I exclusively made money by taking in empty cans and bottles of soda to the grocery store. Whenever my extended family would have birthday parties or get togethers, I would volunteer to recycle the bottles (as long as they would let me keep the money). 😬
11. Selling in Bulk
When I was 11, my 6-year-old brother had a ~girlfriend~ named Julia. I had outgrown my Barbie and Barbie accessory collection, so I sold it all to Julia for $50. This was maybe seven years worth of Barbie-collecting, and I didn't think it through. I cried and regretted this business decision for years to come.