A lot of the biggest Web-related tech money-makers and success stories are things it wouldn't have occurred to me to try, because I'd have assumed they were illegal or otherwise so awful that people'd tar and feather me if I proposed them. Sometimes, they were/are illegal, in fact, but it somehow worked out OK for the founders anyway (business might eventually fall apart, but who cares, they made millions, if not billions)

Spying on what people do on web pages, down to their mouse movements, sometimes. Tracking all that across sites. Then using that to target ads at them.

AirBnB and Uber... just, all of what they do.

Crypto exchanges. It's crazy to me that these managed to go long enough to gain a toehold before facing any sort of banking or securities regulations.

Addictive mechanics on social media and in pay-to-play games.

Mint and other go-betweens with banks that just store and re-use credentials, including answers to "security questions". Seems like a really dangerous idea, probably involves encouraging a bunch of people to violate terms of service on a massive scale, and if you're presenting connections to banks that you know have those terms, seems like you'd be hella liable for that. And my god, if there's a breach that involves your systems and you've been hoovering up people's banking credentials? I'd fully expect to be facing extremely scary and probably-going-to-go-poorly-for-my-company lawsuits from a dozen enormous banks. How do these companies get insured in any way whatsoever? I don't get it. Inexplicably (to me), instead of crashing and burning and being laughed out of the room at any and all fundraising meetings, these made a few people very, very rich instead.

And so on.

Plenty of things not in those categories, of course. Stripe was a great idea, just a hard problem—I'd have had no clue how to seek terms from CC companies to get such a thing off the ground, to pick what's just step #1 of even starting to try at that.

Some are great ideas that I might have come up with, but I haven't a clue about how to even begin to fundraise (I'm not past barely-an-acquaintance territory with any rich people, for even small values of "rich", so that doesn't help), and they're the kind of thing that pretty much requires a pile of cash to even make an attempt—actually, Stripe again seems like a good example. I couldn't feasibly have done even an MVP of that solo, or even with a very small team "in a garage"; the fundraising is another necessary hurdle to even credibly trying.

Some stuff's smart people doing smart things that are eventually very lucrative. Those I (theoretically) could have done, I guess. Redis, for instance. Still, the really big money seems to be in convincing people to finance things that feel like they ought to be illegal (and might actually be), and how that all works continues to elude me. How do you spot a law you can break long enough to get traction against the "dinosaurs" who are bound to follow the law, versus one that will land you on the losing end of a ruinous lawsuit and make your name mud, or in prison? Do people actually know how to spot those, or are the successful ones just lucky? Is that in fact almost all laws once you have some rich people backing you? I haven't a clue.

(Nb this is not intended as sour-grapes complaining, but rather an exploration of the ways in which "having an idea" is a really, really long way from even making a meaningful attempt at implementation for a variety of prominent tech products, including such hurdles as not understanding when doing illegal or horribly unethical stuff is actually a very good idea, if you're just trying to launch a product and get rich—these are deficiencies in my understanding of the world, clearly)