This ended up being a combination of issues and I want to leave some good help/debugging steps here for future Mac users with this issue.
First, make sure you have the latest Ledger Live version, and the latest firmware on your ledger. You can open Ledger Live and click the "manager" link in the left hand navigation menu of the ledger live app. If your device firmware is not up to date, you will see a blue banner telling you that there is a new firmware version and asking you to install.
Ledger has a good step by step guide on how to debug most of this issue. These steps are an excerpt from the link above:
Most connection issues occur because Ledger Live doesn’t have the
required rights on the computer. Please enable full disk access by
following the instructions below:
- Open System Preferences.
- Go to Security & Privacy.
- In the Privacy tab, add Ledger Live to the Full Disk Access list.
- Try again to connect your Ledger device to Ledger Live.
The above steps did not immediately work, and only worked once I restarted my computer.
There is another step suggested by ledger if the above steps and a restart don't work, and this is:
Another solution is to reset the PRAM or NVRAM on your Mac. Follow
Apple's official instructions to do so before you retry in Ledger