In the constantly changing environment of the 1990s and beyond, businesses large and small need to have a well-thought-out strategy that is based upon the best-of-breed products or services with excellent support to compete in the market. In this paper, we propose a five-step model for small business IT management based on a small business story of John Dryden. The modeling process includes: 1) developing business competition strategy, 2) developing operations strategy, 3) developing technology strategy, 4) implementing systems integration, and 5) conducting facility management. The associated enabling and/or emerging Web-based commerce technologies for small businesses are illustrated and recommended.