Systems and methods utilize a distributed server network to allow for the optimization of the upload of a data stream from a computing device. Performance metrics are estimated for different network paths from the computing device to a variety of entry servers in the distributed server network. Based on the estimated performance metrics, one or more entry servers are then selected to receive the data stream from the computing device. As a result, the systems and methods described herein allow for high quality upload performance which addresses the first mile vulnerability issues of the data stream. The distributed server network can then transmit copies of the data stream in real-time to other computing devices.