
I’m going to base a lot of this on my personal experience.
You could either
1. Sell it directly yourself
or
2. Sell it at a discount to a service that will then sell it themselves
Read on for my experience / tips selling your iPhone, and for how to do no. 2 should you decide on that as well.
I think the first idea that comes to mind for most people would be to use eBay.
I’ve personally tried to sell my iPhone one a few occasions on eBay. Did not work well for me. I probably listed my item 6+ times, and not a single time did I get a proper bid. All the typical stuff from Nigerians asking me to send them the iPhone, and them faking emails from Paypal.
Free tip: Don’t email anything to anyone outside the US. It is most likely a scam.
2nd Free tip: If you do get scammed, and ebay charges you a listing fee, just contact eBay and they will get it waived.
Craigslist
I eventually managed to sell my iPhone through craiglists. Just find the electronics section and list your phone there. It’s free, and there’s a pretty low chance that you will be scammed. Of course, exercise caution when meeting up with strangers! I managed to sell my first gen iphone, the week before the 3G was announced, for ~400 bucks. That paid for my 3G quite nicely.
Of course, jailbreak and unlock your first gens before you sell them. Unlocking will fetch a much higher price. Read my prior guide to jailbreak/unlocking here. The app that allows you to jailbreak will let you unlock your first gen iphones. Note: You cannot unlock your 3G iphones yet… until someone figures out how to do it. (You can do it via hardware methods, but there is no software method out there to unlock the 3G iphone yet)
Selling it to a third party vendor
Basically you sell to them for lower than what you’d get if you spent the time to sell the phone yourself through Craigslist, but you are paying for the convenience. Take a look at NextWorth if you’re interested.