Wow, the CEO sounds extremely out of touch with the company culture. If your company has a Facebook group for ex-employees to come together and process their terrible experience working for you, there's a problem regardless of if you're able to admit it to yourself. [Edit] Also, what happens if I rent a dress and hate it? Suddenly I'm two days out from an event with a dress that looks terrible and that I've spent $15…
I still can't wrap my head around renting dresses - some kind of specialized costume I can understand (like spiderman or predator), but dress? They seem to be doing some revenue so it does look like a workable idea. What happens to RTR if the big name brands with multiple physical stores start renting dresses too (I don't know if they already do it or not)?
When you hit a certain age there will be 4+ weddings every summer. Women can feel very pressured at these events, because people can be real status obsessed judgmental jerks, and even worse when it's directed at a woman's appearance. On the flip side, buying a new $500+ outfit for each event isn't workable for most people.
Renting name brand fashion items is a great solution. Look killer in a unique look at every event, feel confident, spend 15% of the money.
Now, going from that, to some sort of netflix scale business... I don't really see that.