I came across a neat synthesis of how to approach bootstrapping a software company by consulting, courtesy of Bill Paseman’s LinkedIn profile for his work from 1989-94 at Paseman & Associates (emphasis added):
At Paseman and Associates, I looked for a business model that was self funding, market focused, and let me develop a software product that I would own. I found that Berkeley’s Teknekron had a process I could adapt for my own use.
I then spent 4 years “Looking for an enterprise problem that was so bad, people would pay me to solve it and let me keep the software“.
During that time I consulted on next generation spreadsheets (Objective Software), multimedia databases (Mediashare), Object Oriented chemical structures databases, Tool Integration (Northrop) and a myriad of other things before hitting on product sales configuration (NET and Make Systems).