I have to say, this looks bad for the whole "users first, revenue later" mantra. Now, admittedly, the founders got paid on the flip. But there are users, and now it's later, so... where is the revenue? I heard this moment described as the "where is the land" moment. The crew has been sailing the ocean for a long time and they're running on slim hope. They grumble, then complain, and finally they confront the captain…
I think this is the "revenue later" part.
I think the best outcome would be that this is a one-time weird thing that happened before they found a real revenue model. That wouldn't be unprecedented at all, although every time I can think of, this happens before the founders sell to a large company who can monetize well. For example, I donated to faqs.org when it was just some guy, and now it's owned by some site aggregator I've never heard of. Which is fine with me, because I just wanted to keep it around.
But assuming this works spectacularly, doesn't this just make Reddit completely illiquid? How can you go about selling a company based on revenues that are primarily free-will gifts? What would you sell, a share of profits from people just giving the company money? And what would you tell your donating customers who have zero ownership? Maybe that's all okay, or maybe I don't get it -- is there some way for this to succeed that I'm missing here?