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Welcome to WMF:)
If your product/service would either
1. clearly save him/her time
2. clearly save him/her money
direct approach would work well. The crucial point is that your product/service must and clearly do either one of the two or both, and he/she must be able to see it through very clearly.
Value differs between individuals, but some values are distinguishable universally. Much of it depends on your value proposition also. Strong value proposition can be presented in many ways. Well written copy is a must. Testimonials from respectable sources and/or clients are also effective (nothing new here).
You can become a respectable source yourself by earning a respect from the peers at a place such as WMF, or you can get your work published (industry-related). Getting your work published will add legitimacy to your product/service and enhance the value proposition.
It's difficult to say where your advertisements would be effective without knowing what kind of product/service you will be offering. If you were to fork up the money to advertise at a respected source for webmasters, such as WMF, you'd better be ready as keen webmasters' business will be hard-earned, though very worth it:)
Nuttin' but my MHO
a) Join a few good forums.
b) Reread the TOS to make sure you know the site guidelines.
c) Contribute where you can in the forum answering questions.
d) Be willing to do some research to answer questions in a humble but authoritative manner on your selected topic.
e) Read what you can about how to answer questions in forums. There are a few good docs out there.
f) If you have the time, start your own forum on your own site with the knowledge and experience you have gained elsewhere.
g) Remember that the majority of early business success is due to customer service. Answer any inqueries indepth.
What will that accomplish?
- Gets you recognized as an authoritative source in your area, without being a spammer.
- Generates profile (pre qualified) traffic to your site.
- Puts you in the loop for your keyword and product sector.
- Build a network of great contacts.
- Great nights of sleep knowing you are making a difference. (It will be surprising how much that will matter after you are in biz for awhile).