I hate to say it, because Ross and I have a few mutual friends, but the guy was an idiot, and it's looking more and more like he deserved what he got for being so utterly stupid.
I kinda sympathize with his position in a way. He was clearly in over his head both on the technological front and on the administration front, despite making piles of money. When that happens in a normal business, you hire some help. But how do you find help to hire for such a massively illegal operation? Finding anyone who could be trusted is a tough problem, much less someone who can be trusted and also has strong technical skills.
He hit that point pretty early on.
The again, I wouldn't start an illegal business intentionally...so there is that.
Well, Kim Dotcom is still kicking it.
As for Ross, the evidence might have been circumstantial at best if his un-encrypted notebook wasn't grabbed.
In any event, Ross was running something somewhat more illicit than Megaupload. His opsec probably should have been commensurately better.
Even then, the FBI grabbed him with his laptop logged into the management interface for Silk Road... So he still would have been in some hot water.
(I'm not personally familiar with ZFS, but the ZFS docs, especially https://docs.oracle.com/cd/E26502_01/html/E29007/gkkih.html#... really creep me with regard to this. The last thing you'd want is blocks in your local encrypted copy of PHP source code to be compressed first. And so then you'd think you'd want encryption enabled on a pool, but from reading the docs it seems that feature merely makes the filesystems on that pool inherit that encryption option, instead of doing some sort of filesystem-blind block-level encryption, where there's any variance in the encryption of blocks, or any information that could be derived from locations of blocks. So I think the suggestion to encrypt on a directory-by-directory basis to limit your exposure is not a very good one. I'd recommend that you use a spinning hard drive, whole disk encryption of the sort we have today, take out the battery, and keep your foot by the power outlet.)
That can be achieved by (1) transferring the machine to a portable battery unit without interrupting the power feed from the AC wall adapter and/or (2) imaging the machine's memory and mounted drives in-place.
These are things the FBI has in its toolbox, precisely because "yank the power cable" is how many criminals rely on protecting their otherwise encrypted data.
In your question lies the answer to another: why are exit scams so prevalent in bitcoin marketplaces?
"Comin up the way we did, you know, you kind of expect that. Waitin on it. See, the thing is, you only got to fuck up once. Be a little slow, be a little late, just once. And how you ain't gonna never be slow? Never be late? You can't plan through no shit like this, man. It's life."
Also notice that most criminals are dumb and send their drug shipments through regular mail or air mail..very stupid..and also notice that those shipments tipped off LE..
Take-way anonymous is only secure at its weakest link..the weakest link here was the physical drug shipments..that will never be secure..ever
Well, it can be if you develop your own underground distribution networks, but then you aren't a darknet message board, you're the mafia.
I have no experience in the matter, but I imagine that being the kingpin of such an organization tends to pull one's head in so many directions that it's easy for smart people to do dumb things unknowingly.