This case illustrates the new generation of ebusiness ventures made possible by the Internet and enabling information and communication technologies. AlertDriving is a recent Canadian start-up, which has moved through the microbusiness to the small business stage, and aims for continued growth. First-to-market with a Webbased driver training and fleet risk management service, the business combines e-learning, risk management, and e-business. Their new approach replaces traditional methods of classroom and behind-the-wheel driver training and paper-based fleet management systems. Growth has brought both opportunities and challenges to the firm and its two entrepreneurs/brothers. In particular, they face important decisions concerning continuing to grow revenue and profit.