To porn or not to porn?
swombat: I can only speak for myself, as an entrepreneur myself, so not for VCs and other similar types, but as for me, I would consider the fact that a cofounder or employee has successfully run a profitable porn site a plus. First of all, it'd be quite interesting to find out how that business works. Secondly, as others have pointed out, there are technical challenges to this which are useful on most start-up jobs. Thirdly, it shows initiative and a willingness to do things which are not commonly seen as "the right thing".However, I'm suspicious of the "it's an easy way to make quick money" statement. In my experience (and I started a business that used MLM for its distribution with a friend before - not as disreputable as porn, but also generally looked down on imho), even those apparent shortcuts require insane amounts of work... so the suggestion that you can somehow do it on the side to tide you over seems suspicious. You can start a porn site - but it'll take all your time for 6 months to a year... so if your 2nd start-up is about to launch, I'd give it a miss unless you're prepared to forget about your 2nd start-up for a year.