I don't feel like I ever wasted money other than losing at poker when internet poker first hit.
what i view as well spent money went towards
muscle men
and later, to creepy crawlers which actually ended up making money because I parlayed it into a profitable playground business. my friend and i were local legends when it came to creepy crawlers, artists in a league of our own. People would pay upwards of $3 for a custom-colored scorpion.
edit to add that the [censored] oven burnt the [censored] out of me on several occasions.