Those who always play it safe probably don’t live very interesting lives. Of course, they probably live longer because they see the danger associated with stealing a shopping cart and riding it down Breakneck Hill at 2 am on a Saturday night. But that sure was a fun 4th of July!

Seriously though, no great invention was ever created without a little risk and no one knows that better than the 16 clever people on this list. They gambled everything and hit the jackpot! These geniuses will have you scratching your head and wondering, “why didn’t I think of that?”

Nothing ventured, nothing gained, right?

1. It’s all about the loopholes

This guy actually followed the rules exactly as he was told. Totally the smartest guy in the class.

2. The guilt trip

This could have gone very badly. Luckily this little girl’s dad has a heart… and likes cats.

3. A quick thinker

Guys don’t notice when a woman suddenly has, like, $275 worth of new makeup, right?

4. Minimalism at its best

This last-minute design totally paid off! Plus, it’s super cute. I’ll name him Plumpy and he can be my friend forever!

Ever hear of a vodka burrito? If not, then number 5 is a must-see!