Financial literacy is an essential life skill that deeply impacts individuals’ personal and economic well-being; it includes understanding concepts essential for navigating the complexities of finance like budgeting, savings, investment, and debt. However, traditional financial education methods often struggle to engage learners effectively. This work discusses how entertainment education approaches, in particular, Transmedia Storytelling (TS), can be used to deliver financial literacy content. In this work, we want to examine the use of two common media in the TS field (web game and board game), to understand its barriers and benefits: a) “Financial Frenzy” emphasizes a team experience composed of a board game that leverages the collaborative nature of gameplay to foster learning and teamwork among the participants; b) “Where’s the Finance?” relies on an individual educational experience composed of a puzzle game encouraging exploration and discovery. We conducted a pilot study of the two media, and results showed different potentials for the two concepts; therefore, we unified both concepts and present a redesign of the TS experience to continue studying the potential of transmedia to deliver financial educational content.