In Hippy's Quest you play a young man trying to become a hippy. This reminds me of Frank Zappa's satirical album "We're Only in It for the Money", and there does seem to be a connection between these two works of art. But before we get there, a little about the gameplay. Hippy's Quest is choice-based. Often you choose from a list of option, though now and then there is also free text input. Many options lead to instant death, after which you will have to restart the game. For the rest you'll just have to try everything, hoping to hit on the path that will give you the items you will need -- I assume -- to proceed on your quest.
Ah, yes, the quest. Apparently, this involves entering a hippy hotel in order to register as a hippy; wearing hippy clothes; and then, for reasons that remain obscure, walking to a cliff and climbing down a rope, jumping into a dangerous river, and swimming past a series of lethal rocks.
These lethal rocks are the shareware protection. You need to enter some combination of numbers, but only by sending $10 to John Blake for full registration (or, if you're not rich, maybe sending $5 for 'just the hint kit') will you be told which numbers they are. So it seems that John Blake is, after all, only in it for the money.
Whether anyone enjoyed their random deaths enough to actually send him their hard-earned bucks is a question to which we may never know the answer. If you want my two cents, I'd advise any aspiring hippy to spend it on pot and an acoustic Bob Dylan album instead.