This is normal for a factory flashed unit.
Is there a reason to reset the device? You should only need to reset it if the software upload fails, or there are some bugs with the software that reloads.
If you plug it into your PC or Macbook and the device is not recognized then you should try to use a different USB cable that has support for data transfer (preferably something that you've used to transfer files before). If using different cables does not work and you are still on the original software then please contact us via the store page and we can try to help you out directly.
Both Arduino and Codebender will prevent you from trying to flash a file that is too large, I have no idea if this is baked into AVRdude and I'm not familiar enough with Platformio to make any suggestions there. I didn't think it was technically possible to overwrite the bootloader memory space over USB (without some creative hacks to do it intentionally).
@veritazz if you could take a video and post it in a new thread of this behavior I think it would be helpful because I've not run into it before.
The pins required for re flashing have circles around them and are clearly labeled. You can use any online tutorial for flashing an arduino leonardo on the arduboy.
NOTE: We are currently using the leonardo bootloader but will likely switch to something custom in the future.
It seems that we need to update the bootloader to take advantages to the changes in arduino that will eliminate the bug related to programs taking up too much RAM. Still trying to dig into that one fully.
@Botisaurus Were you using platformio also? Or is it a more general error, let us know some more details and feel free to open a separate support thread with a video or picture if you want.