Whoever you listened to on the Darko podcast was mistaken. Audio over USB is an isochronous transfer. This means that if bit errors are detected, the packet is dropped and not retransmitted. In this case you will hear dropouts, stuttering or pops during playback, not unlike this example - https://archimago.blogspot.com/2014/01/demo-measurements-what-does-bad-usb-or.html. Perhaps the person was conflating transferring audio over a network with a protocol like TCP/IP. In that case, TCP will guarantee reliable data transmission and resend lost or mangled packets.
There is virtually no jitter on an asynchronous USB connection (which is what most DACs use nowadays). The data is buffered and clocked back out by the receiver. Note that in the previous link, although you can hear the errors, the jitter plots appear very similar.
So what does jitter actually sound like? Here is a great website that has audio clips with varying amounts of induced jitter. Have a listen with you and your friend. See if what you hear matches what the audiophile conventional wisdom attributes to 'timing issues' - https://www.sereneaudio.com/blog/what-does-jitter-sound-like