The best way to completely bleed a system is to back bleed. This is done by pumping brake fluid from the bleeder fitting backwards from the caliper to the master cylinder. You can use an all metal pump can or an irrigation syringe and a clear piece of tubing to do this. Just make sure you remove and clean the bleeder fitting first. This method works like a champ.

If you don't want to backbleed, put a clear tube on the bleeder fitting - make the tube long enough that it will go from the bleeder fitting up an inch or two, then bend down into a container. Fill the master cylinder and open the bleeder, then just start pumping the lever. It may be unproductive at first but eventually if your master cylinder is good, it will start to pump fluid. No need to close the bleeder and build pressure then crack the bleeder - just pump the lever. Just make sure to keep the master cylinder full. Pump slowly and completely.

I hope this helped!