I've figured out why I find sales so unpleasant. Being a business owner requires a much different mind-set than that of a typical techie.
I've been working as a sys admin and web developer for the past seven years. As such, I only have to sell myself to an employer or client once, and typically, over a single one or two hour interview period. Having to sell a product or service to a customer who hasn't already "hired" you is a much different proposition.
As a techie, I don't often have to deal with failure. When working on a new project or fixing an existing system that is broken, I just keep working on it until it's done. Rarely must I concede defeat and give up hope of finding a solution.
Failure is a normal part of sales, though. Salespeople cannot always just keep working on a sales prospect until a deal is closed. This would likely result in restraining orders.
With Postica, we decided that Greg would focus on sales, while I would handle technical issues. Nonetheless, I participate in some sales calls, and I become frustrated when sales don't increase as quickly as I would like.
Direct sales requires a lot of repetition. You generally have to give the same pitch over and over to each new potential customer. This conflicts with my natural desire to automate repetitive behavior. When I come across a task that I have to do repeatedly, I usually write a script or subroutine to automate the process.
Part of marketing is to automate the sales message, but when bootstrapping a business with limited capital, much of your marketing message must be delivered personally to potential customers.
I need to find some good books on sales that explains how to get into the correct mind-set.
Michael Cage discusses the need to train non-salespeople for sales. In order to do this, the non-salespeople must learn to think like salespeople.
A couple years ago, I really got into blackjack. To be successful at blackjack requires basically becoming a computer. You must keep track of the count, and bet and play exactly as the rules (based on calculated odds) that you've memorized tell you that must. You must not become emotional after losing a lot of money when doubling after splitting (though you may want to feign being upset for the pit boss's benefit). What happens during a single hand is irrelevant. Your goal is to grind out a profit by having a slight advantage over the house based on the rules and your ability to vary play based on the count.
A fantastic book on blackjack is Million Dollar Blackjack. It describes how Ken Uston and his team won $4,000,000, persevering through lawsuits, pit bosses, the gambling commission, and malfunctioning electronic equipment (they used some computerized counting gear). Business tales are often similar. For example, Joe Kraus's story about how Excite got the deal to be featured in Netscape Navigator is a story about persistence in the face of rejection.
Is there a way to reconcile the techie mind-set with a salesperson's world?
The state is that great fiction by which everyone tries to live at the expense of everyone else. - Frederic Bastiat