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PS: Fixed the link.
I think there is a happy medium between the 37 Signals no-vcs-ever mantra and the business-dude-writes-up-a-huge-business-plan-and-gets-it-funded-before-he-even-starts mantra. This is not the late 90s; trying an internet-based business model is exceedingly cheap!
No doubt things have changed. Look at Guy Kawasaki, He had a Truemors built for 12 grand. Luckily enough for him he is Guy Kawasaki and that alone is all the PR he needs to get it off the ground. While it may not take as much to get a good Internet start up off the ground these days, one thing hasn't changed, revenue. Like I said before, nothing happens until somebody sells something :) I like your analogy Galen and think you're dead on when you identify the positioning required to succeed as in between 37 signals and the "business dudes". I disagree about the "exceedingly cheap" part though. It's not cheap to start any kind of business these days :) In any case, here's one Geeky Business Dude type that's rooting for you, I really like what you're doing.
First, to say it only cost $12,000 is silly; I would pay Guy Kawasaki $50,000 for half of the publicity he has given it and I'd be getting an incredible deal. So yes, it's easy for popular internet dudes to start copycat sites and direct people to them. Second, a $12k personal glamor site is not a business, it's something a popular internet dude can use to get more speaking engagements.
Paul Graham is my cheap startup hero. He's one of the only people online who writes intelligent, well thought out articles. (I do not count myself in that group).
http://www.paulgraham.com/articles.html