But I suspect that it was a "loose lips" thing. Exacerbated, probably, by developing the project gradually. Being sloppy at first, because it was just playing around. Also bragging, and living large. That's a common set of fails. It played a major role in DPR's takedown. Also Sabu, who had been indiscreet on IRC, years before. And Artem Vaulin of KickassTorrents, who registered a key domain in his own name.

There's also the difficulty of accepting and accessing money anonymously. The Sheep Marketplace founder pwned himself when he cashed out. It's very hard to route around KYC law. The safest bet is collecting payments as Bitcon, Monero, etc And leaving everything except operating expenses in cryptocurrency, until it's time to expatriate to a safe jurisdiction, and cash out some of that good wealth.