HomeNegotiatingThe Ups and Downs of Selling an iPhone on Craigslist

The Ups and Downs of Selling an iPhone on Craigslist

This year for my birthday, I was given my brother’s AT&T upgrade to get an iPhone 4. That excited me for a lot of reasons. I got something new and shiny, the ability to video chat, and a far superior camera. It wasn’t something I would pay for myself, but with the upgrade, it was guilt-free.

Actually, it was also dollar free too.

Actually, I made money on the exchange.

What happened?

Well the iPhone itself was $200 with a $36 upgrade fee. I knew I could sell my current iPhone 3G S for around that much, and a quick search on craigslist showed that the lower limit I would get for it was around $250.

Already, it was a great deal and I was ready to pull the trigger.

I ordered my phone, picked it up, called AT&T to activate it…and the service was down. I spent an hour talking to a customer service representative trying to fix the issue, and when he couldn’t, I asked if he could compensate me for the time and stress, so he offered $25. (had I not asked, I wouldn’t have gotten a penny!) Good but not great. I asked for the $36 upgrade fee reversed and he agreed quickly. For an extra day of waiting, I was rewarded with the equivalent of a free month of service. I wonder what would have happened had I asked for $50..

The Lows

Great, so all I had to do was sell my phone on craiglist. People pay a premium for a jailbroken iPhone, and I agreed to sell it for $300, so I jailbroke it for someone who ended up not being interested (was a weirdo who said that since he already came to me, I should accept $20 less than we agreed on. That bothered me, so I said see you later and went back inside. It wasted 15 seconds of my time and he was left iPhone-less, so who had the bargaining power??). I called one of the other buyers. He came to pick it up, and when I asked if he wanted it jailbroken he said no, so I tried to reverse the change quickly and clear all data.

Unfortunately, it didn’t work the way I expected and instead of clearing the data, it did a hard reset on the phone, meaning I had to do a full install of the latest software, which can’t be jailbroken. Of course, he was no longer interested, and I was sorely disappointed.

I was devastated. I upgraded the phone to the newest version of the software, prayed a little, bargained with the G-man a little, and checked to see how much I could get on craigslist. In my mind, I would take anything over $200.

The Highs

It turns out that I got several offers when I set the price at $250, and in the end, someone came and bought it for $270.

All was better. I only lost $10 from what I wanted to sell it for originally (plus a $20 donation to charity that I promised in my bargaining phase).

My eagerness to get that last $20 cost me about 2 hours of time and a ton of stress. Of course, it all turned out well in the end, as it usually does.

My lesson? Stop trying to squeeze every last penny! Take what you can get, be happy with what you have, and don’t worry about getting the very best price. Just get a really good one.

Readers, have you ever made a stupid mistake you thought ruined everything because you wanted to do too much?



  1. Oh boy…when i make one mistake in what I consider a stressful transaction, it will snowball out of freakin’ control…

    My best example is when I was selling my husband’s old car. The title was in his parents’ names and I hadn’t taken it in to get a new one, so I thought we could just fill in his info on the back and move on. NO. That just made it ready to get exchanged to hubby, so I crossed the stuff off. When we finally did sell it, I had to give them an extra signed document to verify that everything was in order and they could buy the car. They wanted to meet the actual owners (parents), so we had to ask them to come for the deal. We ended up selling the car as expected but I seemed to have gone out of my way to make it way harder than it needed to be…I’m lucky to have sweet inlaws…

  2. Awesome man! First question: How do you like the new iPhone. Better camera, noice, voice chat, even noicer, but how much better overall is it? Should I go ahead an upgrade?

    I wonder how much I could sell my 3GS that’s NOT jailbroken for…. is it hard to jailbreak an iPhone?

    Good job!

    • @myfinancialobjectives, I love it, the screen is unbelievable, much clearer, which is great if you watch video (or streaming baseball like me). And the camera is awesome, who knew 5mp looked so great? Everyone likes a new gadget, and this one is sweet. Jailbreaking is one step, takes about 20 seconds. But if you can sell it for $250-$270, why not? But if you like the flexibility and don’t want to renew, stick with what you have.

  3. Get the Android! Drop the Iphone!

    Seriously though, it seems everytime I mess with the ebay reserve price option I end up selling it a second time for less money.

  4. Craigslist is good for honing your bartering skills, and realizing that not everyone presents themselves at face value.

    Played jazz saxophone as a kid, still held unto the instrument for many years after (their expensive new or used). Was cleaning house and wanted to get it in the hands of some new kid.

    Guy played me ended up “flipping” my instrument. Said it was for his kid then turned around and tried to upsell it. Only reason I found out was another mother (who was interested, but didn’t contact me in enough time) found my exact listing description and photos.

    I tried hunting the guy down and called him out. He dodged me like the plague as I tried reclaiming the sale (was feeling vigilant and wanted to get the saxophone to the mother’s daughter). Needless to say, now I’m very weary of Eastern Europeans & Marylanders. :)

    • @FinEngr, I don’t blame him because he can do what he wants with stuff he buys, although that much have been super annoying.

      So when are you going to be giving us a recital? We’d love to hear you play!

  5. Thank for the detailed story Daniel…it’s pretty interesting to see the ups and downs of the story and exactly what worked and didn’t. Pretty amazing the upgrade was virtually free. I just got my first iPhone and I never quite understood how old iPhones could have so much value and exactly how to sell them. Looks like Craigslist is a great market for this stuff.

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