My friend and colleague Sophie Miller, a long-time sales executive in the direct marketing industry, once said, "In my next life, I want to come back as a client." She didn’t mean it this way (I think she meant it as "I want to be in the driver’s seat next time ’round"), but this is great advice for any member of an entrepreneurial team in a software or services business that serves other businesses. The good news is, it doesn’t require the afterlife to achieve it!
Mariquita and I have done some work in our spare time the past two years for two different organizations to help them out with their technology. One is our golf course, and the other is our cousins’ wine store upstate. Both experiences have had us defining business requirements, working with vendors from selection through contract, and then working with the vendor and the organization on deployment and process change. Both have been directly useful for me to take lessons back and apply them to our processes and work with clients at Return Path.