We survey connections between the theory of bi-Lipschitz embeddings and the Sparsest Cut Problem in combinatorial optimization. The story of the Sparsest Cut Problem is a striking example of the deep interplay between analysis, geometry, and probability on the one hand, and computational issues in discrete mathematics on the other. We explain how the key ideas evolved over the past 20 years, emphasizing the interactions with Banach space theory, geometric measure theory, and geometric group theory. As an important illustrative example, we shall examine recently established connections to the the structure of the Heisenberg group, and the incompatibility of its Carnot-Carathéodory geometry with the geometry of the Lebesgue space $L_1$.