Don’t try to hit too much above your weight class at the software company

Before starting Devshop, I worked for 4 other small and medium software companies (the last 3 as head of engineering). Each of these companies had about 25 people (one of them shot more than 100 people during the dot-com boom, but quickly came back to earth shortly after).

At each of these companies, the entire management team had put it into their minds 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 looking for the elusive “million dollar deals.” Back then, I didn’t know any better and as I was simply the head of R&D, I happily agreed with many of the “business” people and put together the engineering plans to build the enterprise-class software for them. They would take care of pulling sales.

None of these companies succeeded in doing what they were trying to do: land and service “big business.” Worse still, they were all eventually crushed under the weight of their own businesses and went into a tailspin. Someone trying to convince me today that a small business (

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