Before starting Devshop, I worked for 4 other small to medium sized software companies (last 3 as head of engineering). Each of these companies hovered around the 25-person mark (one swelled to over 100 people during the dot-com boom, but snapped back to reality soon after).
At each of these companies, it had occurred to the entire management team that they were going to create enterprise-class software and sell it for hundreds of thousands of dollars to some of the largest companies in North America. In a couple of cases, teams were hunting for the elusive “million dollar deals.” Back then I didn’t know any better and since I was just the head of R&D I happily went along with a lot of the “business” people and put together the engineering plans to build the enterprise class software for them. They would be in charge of attracting sales.
None of these companies were successful in doing what they were trying to do: landing and servicing “big business.” Worse still: all of them were eventually crushed under the weight of their own agreements and went into a tailspin. Someone trying to convince me today that a small business (