Refining a product strategy into a roadmap is neither a simple nor straightforward task. Initially, a strategy must be defined for a specific product, addressing aspects such as the scoped time frame, solving a specific problem, or fitting into a portfolio strategy. While a strategy delineates what should and should not be done, the roadmap focuses on balancing short-term objectives, such as sales targets, with long-term goals to ensure future readiness. To achieve this balance, scenarios and use cases can be developed and prioritized for the roadmap. For instance, the BRICE framework can be applied for prioritization. However, strategies often resemble hypotheses, and the roadmap serves as a means to validate these hypotheses—acknowledging that not all hypotheses will be correct, making them akin to bets. The process of defining and refining a product strategy and roadmap is illustrated with examples from well-known companies, highlighting both successful and less successful bets.