I think Reddit might have been more of a PR win than a major investment win. You might argue that it could have been the latter if the team had turned down the Conde Naste acquisition offer, but that might be the point. Without strong revenues it might not have been easy to turn down such an offer. I'm just speculating so please correct me if any of this is incorrect.

They sold six years ago when they were relatively tiny compared to today. There's no way they would have been a "major" win up there with the 4 huge exits webwright mentioned:

"We couldn't get them to tell us the acquisition price, but they did tell us that the company has raised just $100k (all in summer 2005) and currently has an average of 70,000 daily unique visitors and 700,000 or so page views."

http://techcrunch.com/2006/10/31/breaking-news-conde-nastwir...

Reddit was an early PR win. But, if you made a pie chart of returns for YC, Reddit would be a nearly invisible sliver. That said, it established a relationship with Alexis & Steve, one of whom is repping YC in the east and the other came back with Hipmunk, which just raised a huge pile of money in a huge space. So I think it WILL be a huge win for YC... But not from the Reddit exit.