As one entrepreneur/engineer to another: Don't underestimate the legal and logistical effort you'll incur from a caching CDN. People post pirated, abusive, and generally bad things, and if it's on your server, it's (becoming moreso) your responsibility. DMCA and takedowns will consume noon-trivial time, and makes simple corporate insurance decidedly not simple (or cheap). It's typical for media hosting companies to hire teams to handle these issues. I was shocked while working at CNET (way back when) when I found out most of a floor (in a large building) was for webshots' trust and safety team.