The idea I am trying to capture is one of trying to lift yourself up by your own bootstrap (those tags on the back of cowboy boots). Think about it, it is a near impossible task. So is being an entrepreneur/ small biz owner. To do this take strength, persistence, and tenacity. To be an entrepreneur you need a sense of adventure, the willingness to take risks and the courage to do so.
So a cowboy boot is an okay image to associate with the logo but I am open to your interpretation.
Moreover below you will find the more conventional definitions of bootstrapping :)
concept of bootstrapping is defined as follows...
Bootstrapping or booting refers to a group of metaphors that share a common meaning: a self-sustaining process that proceeds without external help.
A situation in which an entrepreneur starts a company with little capital. An individual is said to be bootstrapping when he or she attempts to found and build a company from personal finances or from the operating revenues of the new company.
The idea of the site is to 1) provide training and education on the topics of marketing, management & career development 2) to provide this education on contemporary topics showing micro-small business owners how to do this while bootstrapping 3) to be a central repository of resources that are no-low cost to help build businesses.