@dan1824 As both @livius and @jmarcelino said, you need an USB to serial adapter for the first update. later updates can be done by FTP. SO I try to explain it step by step.
Get an USB to Serial adapter. Choose one where you can set the output level voltage to 3.3V. Some require to solder that, some have jumpers. If you have the choice, get one with jumpers. Such an adapter is always useful to have.
The Adapter has outputs called GND, TX, RX and VCC (or VDD). You need these four. Connect the adapter to you PC and connect TX and RX of the adapter. On the PC a device should be visible for the adapter which did not exist before. On Linux, it's like /dev/ttyUSB0, on Windows it's COMx, On MAC its something like /dev/cu.usbserial-xxxxxxxx. Mention that name. Now start a serial terminal program like screen, putty, picocom for that interface and type some characters. If TX and RX are connected, these should be echoed. After that step, you know that the serial adapter is working and you can communicate with it. If Linux refuses access to that port, add yourself to the dialout group and logout/login again. If that fails or you are not patient enough in that moment, run as sudo.
Connect, in that order, you USB adapter with the WiPy:
USB Adaper WiPy
GND --> GND
TX --> RX (P0)
RX --> TX (P1)
VCC --> 5V
Look at the Pin.Out here https://docs.pycom.io/chapter/datasheets/downloads/wipy2-pinout.pdf
At that point, setting the serial terminal to 115200 Baud, you should get a REPL prompt. Two obstacles: a) TX and RX may have to be changed. The labeling on the USB adapters is not consistent. b) the USB adapter may not supply sufficient power. In that case power your WiPy directly like you did before.
Now you can start the update: Tie P2 to GND. If you now push reset, you should see in the serial terminal a message, that the device waits for an update. Close the serial terminal and start the updater. You have to use the most recent version. P2 is identical to G23, so if the updater asks you to do that, you're already there. If at that point update fails, you have a server connection problem.
Warnings:
BE SURE TO SET THE USB ADAPTER TO 3.3V
NEVER MIX UP GND AND VCC
ALWAYS CONNECT GND FIRST
As long as you obey these rules, you should not damage the WiPy.