Well, the guide under https://www.arduino.cc/en/Guide/ArduinoIndustrial101 (https://www.arduino.cc/en/Guide/ArduinoIndustrial101) is pretty outdated. Some things to know:
Firstly, the standard password is arduino, not doghunter (At least it was for me).
Secondly, the images are outdated, the GUI looks not the closest like the screenshots...
Thirdly, it would be nice to know how to do a factory reset on the Indutrial 101, pressing the 101 RST button for 30 seconds does nothing, neither does pressing the 32U4 RST button for 30 seconds. --> Please see my topic here: http://forum.arduino.cc/index.php?topic=554907.0 (http://forum.arduino.cc/index.php?topic=554907.0)
I will open a github issue as well when I have the time and link it here.