Stochastic matrices and positive maps in matrix algebras proved to be very important tools for analysing classical and quantum systems. In particular they represent a natural set of transformations for classical and quantum states, respectively. Here we introduce the notion of pseudo-stochastic matrices and consider their semigroup property. Unlike stochastic matrices, pseudo-stochastic matrices are permitted to have matrix elements which are negative while respecting the requirement that the sum of the elements of each column is one. They also allow for convex combinations, and carry a Lie group structure which permits the introduction of Lie algebra generators. The quantum analog of a pseudo-stochastic matrix exists and is called a pseudo-positive map. They have the property of transforming a subset of quantum states (characterized by maximal purity or minimal von Neumann entropy requirements) into quantum states. Examples of qubit dynamics connected with diamond sets of stochastic matrices and pseudo-positive maps are dealt with.