Strategists seek a competitive advantage by balancing legitimacy and novelty; however, each approach has distinct risks and trade-offs. Some firms take on too much risk and eventually fail, while other firms only seek risk-averse alternatives that appear to promote safety and optimal long-term performance. We question whether those decisions must be mutually exclusive. We generated and applied two generic strategy rationales to the results of a professional sports gambling pool. One rationale mirrored best practices, and the other included one minor adaptation, balancing risk and novelty. Our findings suggest profit potential for both approaches but deviating from the norm – occasionally and systematically – produced better outcomes. We demonstrate how industry-based best practices can serve as a foundation for rational decision-making and strategy development, thereby limiting potential adverse outcomes. However, savvy strategists should learn when and how to deviate from conventional wisdom to create more value for their firms.