Odds of rolling (at least) one five in n rolls (assuming independence/equal likelihood of rolls) would be => 1 - (5/6)^n. So for six rolls you get 1 - 0.3348 = ~67% chance.
And since the calls stop once he gets a single "five" (a live contact), the odds of subsequent rolls are irrelevant (because they won't waste time calling again).
So the odds of getting at least one "five" in 6 rolls is the 66.52 percent chance LambSlave gave...
Multiply that by 1000 target clients, and it gives you 665.2 likely live phone contacts if you stop at 6 tries, and you have a 16 percent chance of a live contact per attempted call.