Because of our manufacturing and shipping process, your C.H.I.P. might not have the latest software to be able to communicate properly with your DIP. Please try flashing your C.H.I.P. with the latest software:
After flashing, it is important to use an adequate (5v 2Amp) power supply. Some power supplies are labeled at a higher amperage than they can actually reliably supply. Please note that an Apple wall charger will not provide a reliable 2Amp to your C.H.I.P. as it does too much power negotiation.