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Question about portable mixers

It won't quite work that easily. The TRS jack on a headphone output puts the right and left signals on the tip and ring, and the common on the sleeve. A balanced TRS input, on the other hand, uses tip and ring only for the signal, and responds only to the difference in voltage between them. Therefore, a stereo pair of signals at one end will turn into a right-minus-left mess at the other.
He's not working in stereo. Both signals on the stereo phone jack will be the same. We've hooked up many keyboards (consumer grade) to a mixer this way at open mics. Actually, we may have used TS cables ... not sure.
 
He's not working in stereo. Both signals on the stereo phone jack will be the same. We've hooked up many keyboards (consumer grade) to a mixer this way at open mics. Actually, we may have used TS cables ... not sure.

It's not a matter of working in stereo; the problem is that it's a stereo output. When L = R (i.e., mono mix on a stereo output), then R - L = 0.

It would have to be a cable with a TS plug. However, the headphone amp circuitry might be OK with one channel driving into a short to ground via a TS plug, but it might not.