If you can't get him to say "yes," how are you going to pay your rent?
Closing shouldn't be so hard. But the fact is that most people don't close 100% of their opportunities successfully. In fact, close rates of 20% are more common. So why don't the other 80% close?
The Sell Cycle is complicated. With multiple steps and multiple parties, there are lots of ways for it to get derailed. But, then again, you can always complain about the quality of the leads.