How would you spend VC money if you could?

A friend of mine who spent the last several years running some Old Media companies asked me a funny question:


If understanding valuations wasn't important and the risk of losing it all was on someone else's shoulders, then I'd spend some money in one of these areas:

1) Publisher services.  In the late '90's, I thought the music business had the most to gain by the dotcom explosion.  Today, I think the publishers do.  Understanding content and communities is the name of the game.  Publishers have this in their DNA.  They just need services that help them transition their businesses from tired media vehicles to the dotcom world.
2) Social search.  There are lots of opportunities for companies to figure out how to help information find people.  I don't know whether that comes in the form of recommendations, sharing things, subscribing to things, a combination or something else.  But this is a big space with lots of room for newcomers.
3) Web services.  I don't have clear insight into where exactly the best opportunity is in this space, but technologies that move data in and out of databases across the web is probably the single most important aspect of today's online world.  I'd bank on companies that are making RSS the core technology behind their products.
4) Video on the web.  Big media is moving quickly to move their programming to the web.  The user experience for consuming video is clunky, but the pieces are all there.  A new hit product is going to appear here, or an old product is going to look new again, I'm sure.

Top 5 products in these spaces, regardless of ownership?  Hmmm.  Personally, I like:
1) Feedburner
2) Last.fm
3) Del.icio.us
4) YouTube (and there's something very interesting about Democracy TV)
5) I can't come up with a definitive 5th, but I like SixApart, JotSpot and the 43 Things stuff.

Again, I have no idea about valuations and all that, but that's my answer to the question.  Funny enough, I was writing this on the train last night, and then this piece titled, The Next Net 25 came out today on CNNMoney and Business 2.0 from Erick Schonfeld, Om Malik, and Michael V. Copeland.  It's a much more thorough look at what's going on out there.

Also, Fred Wilson is a great source of insight on this type of question for those who aren't aware of him already.

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