If you’re a mere mortal you have to wait for your broker to have a sufficient number of shares available for shorting. If you’re a giant hedge fund or other financial entity with a blatant disregard for the rules, then sure. You just short the stocks naked and issue a failure to deliver if you can’t locate enough shares to cover.
If you’re going to directly connect them using just a single cable then it needs to be a crossover cable and he’ll need to set the IP manually on each end. Most people don’t have a crossover cable lying around. It would be easier to plug both computers into a router/switch and do a network transfer or just get a USB adapter for whatever kind of drive is in the old computer.
Edit: it’s been a while since I needed to dot do that and apparently modern Ethernet doesn’t need specialized cables anymore. TIL.