&gt; The number of issues surrounding the idea (customs, legal issues, etc.) are obvious, and the discussions around them reminds me of the questions thrown at many of the other major sharing economy start-ups initially (Uber, AirBnB, et al.), but with a good team and some experimentation they will figure them out.<p>The rules Uber and AirBNB were flouting aren&#x27;t generally criminal. Smuggling, OTOH...<p>&gt; People who have spent a good chunk of time in countries outside the US, already know people have been informally doing this en masse for a _long_ time.<p>People do this <i>into</i> the US informally, too. And its true that many governments don&#x27;t seem to worry too much about informal importation of items for acquaintances that are within the existing allowances for personal use, but which are actually imported for acquaintances (and, IIRC, many actually have specific <i>allowances</i> for this if the importer is a local citizen, rather than a foreign traveler), technically for trade in that the receiver often ends up reimbursing the importer with perhaps a small premium.<p>OTOH, its really unlikely that any government is going to turn a blind eye to a massive, commercial, advertised end-run around its customs duties, or treat anyone they catch involved in such an operation gently.<p>&gt; To me it seems Shypmate is just creating a formal system for these actions to take place<p>Formalizing informal exchanges often has substantial adverse legal consequences. Observing that gold-digging exists and is visibly practiced doesn&#x27;t making opening an overt brothel a good idea.