If you are just starting out on iPhone development, or are considering starting but don’t feel like dropping $99 without getting your hands wet first, then you’ll need to jailbreak your device.
For me, this was great at first as it was far easier to set up than XCode provisioning profiles, and it let me see if I was felt confident enough playing around in Objective C to really take the dive and pay for a developer account.
In case you somehow don’t know where to jailbreak, head to Dev-Team Blog and download the appropriate torrent.
A quick note: I own one of the new Aluminum MacBooks and still have not successfully jailbroken my iPhone using it, due to some error/bug/whatever with the USB drivers failing to put the device into DFU mode. Just find a windows computer to use for 15-25 minutes and use QuickPwn on it.
After you jailbroken your device, you still need to do some tricky steps to get your own compiled iPhone app running on your device. You can find a walkthrough of how to do this here.