When professors teach complex topics like trademarks in a business law or legal environment class, the delivery is often too abstract. Textbooks tend to focus on black-letter basics of trademark law, ignoring strategic considerations. Experienced managers know that the strongest trademarks (legally speaking) do not necessarily sell products. These issues are often not addressed in the classroom. This article addresses the gap between the legal, business, and social world of trademarks by describing classroom exercises intended to bridge the essential concepts. Depending on the time available and the course's level of emphasis on trademark issues, professors may choose to implement some or all of these exercises in a legal environment, business law, intellectual property, marketing law, or entrepreneurship course. The exercises are designed to quickly communicate complex intellectual property and branding concepts, allowing students to translate them into real-world decision-making. Significantly, these exercises help students engage their emotional, creative, and strategic problem-solving skills. At the conclusion of these exercises, students will be able to: (1) Define the trademark right, and identify how it provides a competitive advantage by ensuring fair play and protecting return on investment; (2) Explain the process for obtaining a trademark, and identify the limits and advantages of a government registry system; (3) Distinguish legally strong trademarks from weak trademarks; and (4) Apply both marketing and legal considerations to identify the optimal trademark for a new product or service.