He's having serious problems with multiple flats because ....... when he gets home at night, he empties all the air out of his tires. Then, first thing in the morning, he pumps his tires up from completely flat. He's most likely getting pinch flats because somehow I doubt he takes the time each morning to make sure the tube is not pinching when he pumps them up. Days when he doesn't get a flat happen out of pure luck.

He needs to fill his tires and then leave them alone for the next couple weeks. After a couple weeks, he should check the pressure in his tires and if it is a little bit low, he should top up his tires ... not from empty, but from whatever pressure they are at.