@pg I think a great one would be "b2b customer acquisition". This was one of those things that we realized was CRAZY HARD and (anecdotally) I've heard a few other YC startups who have run into this wall. Stuff like inside vs. outside sales, lead generation techniques, hiring salesfolks, adwords, etc.
Of course this stuff only applies to maybe 25% of YC companies out of the gates (tho eventually, even the consumer plays have to hire ad-sales guys).
The process for getting consumers to pay $5 is completely different than the process for getting someone to pay 25k, so I think it makes more sense to split them up. Even just focusing on lead generation would make a lot of sense, since that's one of the hardest parts of B2B sales.
A no bullshit advertising conference might be good as well. We've learned tons of stuff on network vs direct sales that took a long time to figure out, and the fact that the advertising industry is filled with less than intelligent non-engineering people didn't help that process.
Amen. I've heard a lot of people run into same issue we did (wufoo and Joe Kraus' Jotspot both talked about this issue). We started with a free product, turned a paid product and promptly said, "WTF! Why aren't people buying our premium stuff?!" It was a long learning-intensive road to get smart(er) about freemium.
Of course this stuff only applies to maybe 25% of YC companies out of the gates (tho eventually, even the consumer plays have to hire ad-sales guys).