Android - Can't get adb on Macbook to see Pixel C

I have tried a number of USB 3.0 cables with no luck but every high quality USB 2.0 cable I've tried has worked for me. This includes USB 2.0 cables that have a Type C connector (There are many of these on Amazon. I'm currently using an "iOrange" brand cord) as well as traditional micro-usb cables with a Type C adapter ("TechMatte USB-C to Micro USB Adapter").

I'd prefer faster charging and better speeds but this takes care of my debugging needs reliably.

Unfortunately, I've found that rebooting the mac will cause the adb to recognize phones through the usb-c, even if I later unplug and plug it in again. Eventually, something happens and it stops working until I reboot.