As a 12 year old, I didn’t have any real skills. Just about the only thing I knew how to do was play and do chores. So naturally, I starting a leaf raking business. As a chore raking leaves was the worst. However, for a little cash money it turned out to be AMAZING!


How do you set prices? This question is still very relevant to me. I came up with $10/hr per person. It seemed fair, manual labor is crazy hard. I have a lot of respect for people in that industry.

That Grassroots flow

Ol’ school style. Let me remind people of the technology of the early 2000s; Modems were singing loudly, average page load time was about three minutes and chatrooms were the official home to creepers! My only option was to take it to the¬†streets.

I created a flyer on Word on bright yellow copy paper. It had a really cheesy picture of my friend and I raking leaves in my backyard. I ran around my neighborhood dropping them into mailboxes. Have you ever done this? It’s horrible. After doing most of the houses in my neighborhood, I was done! Thank goodness!!

Raking in the green

I raked in about $1300 a season, pun intended, which was big money back in the day. Not sure what I paid out. My books were nonexistent. Thinking out loud I should get a better grip on my books.

Reinvesting was the best thing

Every year I would purchase new-to-me equipment, like backpack leaf blowers from newspaper classifieds. I would scoop these up after the season ended, so they were super cheap!

My Take Away

This business has to be the reason I can’t do anything except be an entrepreneur. It’s gotta be. Damn, who knew 12 year old me would have such an impact in my life? I didn’t. I’m kinda curious to hear about other peoples middle school grinds. If you had a hustle post it in the comments or just email