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I aim at demonstrating how both Nicholas of Cusa and Leibniz glean from the platonic school of thought the idealistic notion of ‘truth as expression’, orienting it towards the singularity of being. I will also reveal a second assumption derived from the philosophia perennis by both thinkers: the idea of philosophy as hypothetic and intersubjective undertaking. The theoretical results of this philosophical conceptualization are formulated in the name of the Possibility rather than in the name of Necessity. Under this shared perspective, Nicholas and Leibniz interpret the substantial forms (formae substantiales) as “unities without plurality”. It follows that the dialectic subjects can only be two: the creating God – Monas monadum for Leibniz – and the created substantial forms. In slightly different ways, Nicholas of Cusa and Leibniz deny an autonomous ontological status to the World and its uniqueness. Nevertheless, the substantial forms need a unifying structure to become intelligible to the humans. Such frame can work as a topological conjunction that bears the intermonadical and anagogical paths, leading the spiritual monads back to their principle. The Cusanian and Leibnizian venationes sapientiae are both embedded in a coherent paradigm of transcendent, monadic, and finalistic idealism.