What did work however was I went to to first log in to the account (or create one) and after I logged in I navigated to Support > Download Leapfrog Connect from their main website ( ) to download the program.
I tried changing the cables and even different laptops but no luck. So actually I was able to connect to the leapfrog leapstart fine before and this time no matter how many times I tried after connecting it to the PC the program did not recognize the device and would not connect.