HIM: "Mainly small-medium sized local businesses looking for a way to increase their ranking. Most already have a branded domain in place, and have heard that using a keyword domain can help. Or they have seen a competitor ranking using that method. The problem I face is that they don't have a lot of money to spend, so I get lowballed on the asking price. There have been a few that make a ton of profit vs what I purchased it for, but that boils down to luck: what is for sale, when I find it, things like that."

It is mind boggling how local search engine optimization has grown from a tiny market to a mammoth industry within a span of ten years or so. This is also one of the reasons why focusing majorly on local names is profitable. From doctors to pizza parlors to salons, everyone wants to see their business thrive on the first page of Google Search results with the help of target keywords.

Joe Styler serves as product manager for the aftermarket at GoDaddy. He’s responsible for marketplace products including any purchase, sale, or monetization of a domain name. During his nine-year tenure at GoDaddy Joe has served in a variety of directorial and supervisory roles. His passion is seeing his customers become successful in their business goals when using the aftermarket. He has been interested helping people with transactions on the Internet for more than 20 years. Joe received his B.A. from Moody Bible Institute in Chicago, and his Masters in Divinity from Gordon Conwell in Massachusetts.
Here's a test I have in process.  I bought an old $5 closeout domain from Godaddy TDname expired auction.  I put a quick minisite up and linked to it with a crazy anchor text phrase.  The domain is ranking for that crazy term now.  It's gone through one pagerank update and I'm waiting for a second to come.  Then I'll redirect the domain to another minisite.  I suspect the second site won't rank for the anhor text, but we'll see.  
This is a little bit on the grey hat/black hat side of the spectrum. But the fact is building a blog network with expired domains flat out works. The only issue is getting those cream of the crop domains without going broke. This video will walk you through tested strategies and techniques you can use to find powerful, yet affordable, expired domains.

HIM: "Mainly small-medium sized local businesses looking for a way to increase their ranking. Most already have a branded domain in place, and have heard that using a keyword domain can help. Or they have seen a competitor ranking using that method. The problem I face is that they don't have a lot of money to spend, so I get lowballed on the asking price. There have been a few that make a ton of profit vs what I purchased it for, but that boils down to luck: what is for sale, when I find it, things like that."

Granted, it is not bad information, however, if EVERYONE rushes to namejet and signs up, the only people that really benefit are namejet 😉 The increase in competition means there are more bidders in the pool which will likely increase bid amounts (because the newcomers will not be able to ascertain a “true value” as much as a “pro” flipper would). The result is a lower profit margin as the method becomes saturated.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.
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