Bob has an iPod Touch connected to Ford Sync via USB. When he stops the car, he loses his place in the podcast he's listening to. Leo says iTunes and the iPod is set up so that if it stops in the middle of a song, it would start over, but if it's an audiobook or podcast, it would start where it left off. It does this based on hidden data in the file to tell the iPod what type of file it is.
Leo advises going into iTunes and under podcasts, look in the settings to tag that file as a podcast. He should select all his podcasts, then "get info". Under the options tab, in Media Kind - select "Podcast". Or "Audio Book" for audio books. Then check "remember playback position." Also make sure the iPod has the latest firmware.