This issue on OS X, https://code.google.com/p/google-glass-api/issues/detail?id=243 is still not addressed (please star the issue while there), it still exists post XE8 regardless of how you start fastboot which as noted, times out and will reboot after inactivity of just a few seconds. Part of the problem is that the USB vendorId switches between Google and TI when switching between adb and fastboot (bootloader) modes.
The solution for Windows:
In android-sdk\extras\google\usb_driver\android_winusb.inf
Add to both the [Google.NTamd64] and [Google.NTx86] sections 2 additional lines:
;Google Glass
%SingleAdbInterface% = USB_Install, USB\VID_18D1&PID_9001
%CompositeAdbInterface% = USB_Install, USB\VID_18D1&PID_9001&MI_01
%SingleBootLoaderInterface% = USB_Install, USB\VID_18D1&PID_9002
%CompositeAdbInterface% = USB_Install, USB\VID_18D1&PID_9002&REV_0100
Then from ControlPanel->System->Device Manager confirm the VID and PID values with the yellow warning tagged device or “unknown device” - if not the same, edit to match these values.