Bootstrapping technology entrepreneurs are a special breed, especially once they cross the desert to profitability. There’s a real challenge that occurs when attempting to shift away some of the scrappiness inherit in a bootstrapped culture to being more aggressive with resources so as to maximize growth. Here’s one question I like bootstrapped startups to think about annually:
Where would you direct your resources if you had an extra $1M/$10M/$100M that you had to spend in the next 18 months?
Thinking bigger, especially when it comes to resources and money, isn’t done frequently enough with bootstrapped startups. With this question, the goal isn’t to encourage entrepreneurs to go about raise institutional money, rather, the goal is to stretch the mind and contemplate putting a significant amount of money to work in a short period of time in new ways. Thought-provoking questions like this are good for entrepreneurs on a regular basis.
What else? What are some other questions bootstrapped entrepreneurs should think about annually?
David Cummings on Startups 
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