All that being said, please do legit speculation and investment to your heart's content. But don't just do the easy thing and cyber-squat on existing business names.
I'm not suggesting you would, but I stumbled onto this one guy again yesterday and he's a perfect example of what NOT to do, a guy who in my opinion is 100% a full fledged douchebag cyber-squatter to the fullest degree.
Just that I know if, he's registered 700+ .CA domains of Canadian businesses or global corporations where the actual business bought the .com/.net/etc... He also does it in other TLDs. He does have various CDRP & UDRP against him, I'm shocked there's not more considering it is so bloody blatant. But he prices most of those domains at a couple thousand bucks and they probably figure its cheaper & faster to pay his price.
I'd have no problem with this if those domains were truly or even marginally generic, one word or even multi-words that are a product or service, or even showing a pattern of made-up domains.
But these are made-up/fanciful type domain names, or multi-word domains (sometimes 3 and 4 words) that are clearly targeting a single company.
Now if you had a portfolio of 700+ multi-word or fanciful domains that were speculating at what might be popular, for example we've talked about colours here, so say "red", and then you put another word with it like reddog, redcat, redbird, reddragon, etc, etc, etc.. and it just so happens that one of them turns into a big company and you make a great sale, that's perfectly acceptable speculation & investing. Or lets say you notice that there's 50 companies with the name "reddog" (i.e. reddogpizza, reddogfinance, reddogtravel, etc), then you register reddog.ca because its clearly a popular phrase and you're not targeting any single business. I'm cool with that too.
But when nearly every domain in your portfolio is clearly targeting a single business, usually an exact match .CA for the .com/net/etc... there's clearly no acceptable speculation going on - it is blatant cyber-squatting, and frankly its those types of people that really give us all a bad name.
I'd call him out right here, but I notice quite a few of you are contacts with him on linkedin. Probably because you don't realize the extent of what he's doing... but I wouldn't want to be associated with him in business personally. Its possible that he's even a member here.
Now I'm no perfect angel - I'm sure I have the occasional domain that looks questionable. But instead of a relatively small % of questionable domains, this guy is at 95+ % pure cyber-squatting, not even remotely what could be considered speculating.
So when you're deciding how to proceed with your domain investing strategies, please, don't be a blatant cyber-squatter. Speculate all you like though!