I think as much as Kleiner may not be interested in web2.0(or so they say), many web2.0 entrepreneurs aren't interested in Kleiner either as much as they previously used to be.
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.
I agree, my first thought was that how KP defines a good investment is somewhat orthogonal to how someone defines a good business.
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.
Sitting out on the infancy of web 2.0 (Kleiner Perkins/Microsoft) if you don't have eyeballs to appease (Google) makes heaps of sense.
User-generated content (I speak primarily of video as that is my research/startup focus) will be history in many niches as more and more companies get into the business of making excellent, interactive web video content. This superior content will have many unique and unobtrusive ways to be monetized, and in none of the ways (pre-roll, post-roll) ad companies are trying to fit to user-generated content.
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.
Earning off Google adsense is not a business, it is a hobby. Very few startups manage to squeeze a reasonable profit off Google.
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).
Instead a model that would help them reach people, casual surfers can be made potential customers, educated customers would spread it around. This food chain will make everyone happy. I dont know if it would go as planned but still whats there to try :-)
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.
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.