> "move fast and break things" wasn't meant to apply to laws.
The law is a messy area. Many places are simply unresolved until a court gets to them, and often there is no incentive for that resolution to happen, so the question gets a lot more complicated.
Here's an example (In all of this I'm trying to focus on legality and not if I think it's a good thing. I'm also not a lawyer and likely have lots of details wrong). I get around to saying why this is relevant at the end of this wall of text.
In the world of tabletop RPGs (D&D and the like) there's a big grey area as to what is/isn't protected by copyright.
From general literature, we know (indeed, it was one of the big pushes for the creation of copyright) that translations and other "derivative works" are covered by copyright.
From boardgames, we know (have court cases saying) that _rules_ aren't copyrightable, while the exact expression of them are. I can make a Monopoly clone so long as I don't violate any trademarks (which are different than copyright) and use my own words to express the rules.
From comics and other literature, we know that characters and settings can be covered as "derivative works". I cannot write my own Superman take, nor have a story involving Superman and the Justice League even if I omit/replace the exact trademarked words. Three notes: (1) Parody is an allowed defense against copyright infringement and (2) A lot of stuff happened in the early years of comics that today would likely not fly today. (3) Given the universality of themes, there's lots of dispute about what creative works are or are not derivative, in both a legal and non-legal sense.
But a tabletop RPG lives in a weird place: it is rules...for telling a story. It may come with characters and a setting...with the intention that people use them. Is my use of the product creating a "derivative work"? If I make an adventure that assumes you are using the rules but doesn't include any of the text, is that a derivative work? Does that change if I refer to setting details?
For a long while, the expectation was that, no, if you avoided trademark infringement and didn't copy exact text, you weren't infringing. Several RPG magazines would buy (from freelance authors) and sell (as the magazine to subscribers) adventures for various different systems. [Notable exception: Palladium games, maker of Rifts, TMNT, and other (ahem) strangeness) were very prickly about this, so magazines simply skipped them and didn't offer adventures for them.] Heck, adventures were such a cost sink for game publishers and so requested (but unbought) by audiences, it was generally considered a SERVICE to the publisher to put out adventures for their material, as it would drive demand for their books.
Now, this was the genre-wide expectation (excluding Palladium), but it was never actually legally established. RPG companies were (and often still are) shoestring budget operations, and a bad judgement (and if I learned one thing from my lawyer friends, it's that initial court decisions are often bad judgements - it's why appellate courts are so important) would devastate many companies and the hobby that relies on them. Heck, just going to court would destroy most companies at the time, even if they'd eventually win. So the law in the area was allowed to continue undefined, with the few cases that cropped up almost always (always?) settling out of court.
Side note: Think games aren't terribly relevant to the law? Check out how the EFF came to be in relation to tabletop RPGs: http://www.sjgames.com/SS/
Then Wizards of the Coast (The Magic: The Gathering people) bought TSR (The Dungeons and Dragons people) and came out with D&D 3rd edition. This is when Linux was breaking free from the "you get what you pay for" stigma, when "open source" was a new term (vs free software), and when Stallman vs Raymond had just finished peaking. The concept of open licensing and copyleft was getting a broader awareness, and tech and RPGs have always had a tight bond, so when D&D introduce the Open Gaming License (OGL), to set explicit rules to allow derivative works, it was a big deal.
The OGL did a lot of things. It spawned a revolution in the RPG market that would bring in a lot of new players, spawned a bunch of new companies - most of whom folded just as quickly, but a few modern companies made their start then and survived - crushed or crippled some relative giants in the industry, dealt a blow (due to unsold product) to the RPG stores that were already reeling from the correction in the trading card industry...and normalized new intellectual property practices.
The OGL made it clear what was allowed to be done, and even allowed activities that distinctly required permission under copyright...IF you accepted limitations that are probably more than copyright would ever require. If there are gaming magazines (or 'zines, or any other commercial enterprise) that offer adventures without explicit license, I don't know of them. Similarly, character creation programs and the like all operate under explicit license now...because we're never figured out if they need to.
Bringing this all back to the original point: "move fast and break things" in terms of the law has two possible ends: you either tick off the established players and they bring the law against you and resolve the legal vagueness one way or the other, OR you establish a new norm because no one has the resources to challenge you (and if they did, the fact that you created an accepted norm makes it more likely that the law will accept that as the norm: See how EULAs have crazily become enforceable without even offering refunds if you don't accept in most situations).
End conclusion: Is "move fast and break the law" good? I really don't know. I feel like ending vagueness is good, but I feel like allowing initial corporate actors to define the starting point of the new rules is bad. Either way, I feel like it's a different situation when you're dealing with legal vagueness than when dealing with clear established laws in the Uber and AirBnB situations, but even in those cases the "little guys" weren't going to be able to impact the law without a clear market demand...and yet, I don't like encouraging companies to play fast and loose.
Messy.