Pulse self-compression followed by the generation of resonant radiation is a well known phenomenon in non-linear optics. Resonant radiation is important as it allows for efficient and tunable wavelength conversion. We vary the chirp of the initial pulse and find in simulations and experiments that a small positive chirp enhances the pulse compression and strongly increases the generation of resonant radiation. This result corroborates previously published simulation results indicating an improved degree of pulse compression for a small positive chirp [1]. It also demonstrates how pulse evolution can be studied without cutting back the fiber.