There’s a bit of a background to this binge….My primary domain investing strategy is to speculate on domains that I believe will become generic at some point in the future. This strategy offers the advantage of being relatively cheap - most of the domains I identify are still available for registration. But, the risk is significant - there is no guarantee that the names will actually become generic (or even well-known).

A few weeks back, I decided I wanted a few political domains before the 2008 US presidential election. I figured that “all the good names were taken” and made a decision to throw my speculative strategy out the window. I started searching the aftermarket to see if any good names were available.

I found very few that interested me, and got a bit frustrated. Then, on a whim, really, I decided to do a bit of brainstorming and see if I could find some good names there will still available for registration.

To my surprise, I found - and grabbed - some decent names. I didn’t realize it until after I binged, but my speculative strategy actually played two roles here:

1. The value of these domains, clearly, depends on the outcome of the 2008 Presidential election;
2. Some of the best domains from this binge (in my eyes) are .us domains…the value of which is still largely unproven

With that as background, here’s my binge on political domain names. In each group, I’ve put the domain(s) at the top that I think has the most potential.

Technorati Tags: 2008 election, domain names

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Yesterday, though, that strategy was tested. I received an offer to buy a speculative domain that I’ve been holding for less than a year. The initial offer would have given me nearly a 100X profit (and would have paid the renewal fees on my portfolio for a long time).

I have to admit, it was a tough decision despite my commitment to the buy and hold strategy. I’ve set up my domaining business as a pure sideline - I pay for all of it with ‘extra’ money and don’t need it to generate any cash. But the temptation to realize a 100X profit was incredibly strong. Only a crazy person would walk away from that, right?

Wrong. I ultimately decided that only a crazy person would flip this domain at this time.

How did I make the decision? This was the hard part - I hadn’t received an offer like this before, so I had no frame of reference or rules to go by. I had no idea how to assign a value to the domain and, therefore, had no meaningful way to analyze the offer (other than “hey, that looks like a bunch of money”).

I thought about it for a bit, and ultimately scratched the following questions on a notepad:

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