Step 1: Get SyncMate Expert edition.
First of all, download and install Free edition of SyncMate on your Mac. iPod Nano can be synced with SyncMate Expert edition only, so, once SyncMate Free is installed, you will need to upgrade it to Expert Edition
Step 2: Connect iPod Nano to your Mac.
Launch SyncMate and establish connection between your Mac and iPod Nano - SyncMate can sync these devices via USB cable.
*Have any questions? Read this article.
Step 3: What do you want to sync?
With SyncMate Expert you can sync music, videos and pictures between your Mac and iPod Nano. You can also sync the contents of the folders on both devices. Moreover, you can back up iPod Nano data on your Mac and restore it when required.
Now please check the boxes of the plugins you are about to sync.
Step 4: Choose sync direction
There are three directions of syncing data between Mac and iPod Nano - Mac to iPod (Mac data will be added to the existing entries on iPod), iPod to Mac (iPod data will be added to the existing Mac entries) and bi-directional - data will be mutually updated on both sides.
Folders can be synced in three directions; iTunes & Video can be synced in one or two directions; iPhoto can be synced in one direction only - from iPod Nano to your Mac.
Step 5. Sync NOW!
You're almost there! :) Just click "Sync now" button and your data will be updated on both devices!
Step 6. Sync even more devices with your Mac!
It's not only Mac with iPod Nano sync solution actually. SyncMate can also help you sync your Mac with Windows Mobile, BlackBerry or Android devices and Nokia S40 phones, other Macs and Windows computers, Sony PSP, MTP devices, Google or Dropbox accounts, iCloud, Yahoo!, iPhones, iPads, iPods Touch, any mounted storages.