In this paper, we investigate the topology convergence problem for the gossip-based Gradient overlay network. In an overlay network where each node has a local utility value, a Gradient overlay network is characterized by the properties that each node has a set of neighbors containing higher utility values, such that paths of increasing utilities emerge in the network topology. The Gradient overlay network is built using gossiping and a preference function that samples from nodes using a uniform random peer sampling service. We analyze it using tools from matrix analysis, and we prove both the necessary and sufficient conditions for convergence to a complete gradient structure, as well as estimating the convergence time. Finally, we show in simulations the potential of the Gradient overlay, by building a more efficient live-streaming peer-to-peer (P2P) system than one built using uniform random peer sampling.