To trust Cloak or a similar company, we have to believe that it lacks the motivation to engage in theft and possesses the competence to configure its systems well and keep them up to date. The test of both of these is often time: we need to know how they perform longitudinally and when faced with threats. One code-hosting and project management firm shut down last June when its "full redundancy" and "real-time backups" were shown to be hollow, as all its infrastructure was protected by the same Web services credentials.
Duane, I'd like to say the real answer is that most businesses engage in ethical behavior, whether it's because the owners want to do the right thing or because the cost of ethical or legal violations is so high it deters them. Can we ever know for sure that a given company deserves our trust? No. But we can calculate the odds by looking at the technical and legal factors that underlie why we grant trust to any business.