He asks some great questions for any business idea, but particularly for Web2.0 ventures. Worth paraphrasing I thought:
1) What gives you an unfair advantage?”
Most likely that takes the form of deep technology, proprietary content, or an exclusive business deal.
2) What is your business model?
One thing technical founders often do is put the product or service out for free, planning to put in the business model later. Often, however, the business model needs as much rapid development as the feature set, and can take quite a while to emerge.
3) Are you a feature or a product?
If your service depends on another service or community, like MySpace, then you’re going to face questions about why MySpace wouldn’t just duplicate your functionality. There is a fine line between “boiling the ocean” (trying to do too much) and being just a feature, and that’s where you want to position yourself.
Finally, there are a couple of characteristics that will definitely help your case. One is a clear understanding of your short-term direction, and the specific milestones you are trying to reach – e.g. number of visitors, downloads, etc. Another is a culture of rapid prototyping and fast learning.