Advertisers are not equipped for ultra-niche marketing, and most web 2.0 ajax/flash heavy experiences are not well suited to traditional banner buys.
And so, we end up with engineers building blindly for uninterested advertisers.
The engineers and technologists creating these platforms often seek to embed advertising or marketing opportunities into their products, with little understanding for either:
(a) the advertising/brand marketing construct and the resulting needs and opportunities, or
(b) the need for a strong dual core value proposition - uniquely and suitably addressing both the needs of the users and the needs of the brands and the broader branding community.
Smart startups consult with people who get it. Smart companies are constantly in touch with their strongest customers/target customers and users, optimizing their offering for their core constituency. Few companies can pull an Apple out of their hats, generating products that are insanely popular on instinct and insight alone.
If you are a web 2.0 company, if you are looking to succeed in the age of accelerated socialization, it is time that you started socializing. There are people who get it. Just because you think you know your business, doesn't mean that you understand the intricacies and eccentricities of your target audiences and clients.
My Advice: Never stop consulting with visionaries. Never stop creating meaningful relationships with the "people who get it" at their respective agencies/unagencies. Just because someone has a senior title doesn't mean that they understand the new digital dynamic, and just because you may have a large user base or a flashy tool, doesn't mean that you're going to have a successful or compelling business.
If you aren't learning, you are growing. If you aren't using GPS or a map, you're going to make a wrong turn, because trust me, these roads are unlike any we have seen before.