Kleiner Perkins Partner: If by Web 2.0, you mean companies that build an audience to be monetized by Google, I am not actively pursuing them.
venturebeat.com
venturebeat.com
For example, in web2.0 world a 15mil exit is considered pretty nice. But for Kleiner a 15mil acquisition of a portfolio company doesn't necessarily get them jumping.
You mentioned that a small exit is a home run for three guys in a room. Likewise, three guys in a room can be financed by Visa and Mastercard, they don't need KP.
I think, as this natural evolution occurs, we will see the likes of Kleiner Perkins and Microsoft bidding high and wide, as the next five years will be very kind to professional content providers.
They are skeptical right now because they should be. The attention span of the average web surfer is short as is his loyalty. A major content revolution is about to occur and it will be fascinating to see who the major players will be, and who (Youtube?) the major players won't be.
I am making a huge and possibly erroneous assumption that these early-stage 2.0 companies can't evolve into what I describe above. I base that assumption on inflexible attachments to branding (hangover from advertising 1.0). Much like a first impression, a brand is a difficult thing to change.
Advertising is, of course, a feasible business. But no one (this especially applies to geeks) clicks on Adsense ads anymore because they are so used to seeing them. My suggestion is to develop a custom ad delivery system, or manually post sponsored ads (just as TechCrunch does).
So there is lot of money in getting small startup companies into advertising and web 2.0 is just a beginning. If someone thinks google adsense is ultimate product, there are flaws and once can correct this and still make ad revenue.