I don't think its fair. A modern web application is expected to do a whole heck of alot more than COBOL as it was originally designed even envisioned. You can still bang out a simple shell script or procedural program in Ruby today without knowing much of anything but we just don't consider those things 'applications' anymore.
Hell COBOL (propper) isn't really even interactive, its read in records, and write out some other records. You needed something like CICS to do much of anything interactive and guess what its not so easy to use or understand anymore once you go there.
Lets not even talk about the job control stuff to get your program running in the first place; normal people were never expected to handle that, it was the job of the OPERATOR who HAD EXTENSIVE TRAINING to do that.
So really its just not true.
Applications are more complicated to build today fundamentally because they are more complex in terms of what they do. Could it be simplified yes, we could fix lots of the technical kludges by replacing http and other web technologies with some truly stateful application delivery protocol and languages + libraries but it while it would be simpler it would not be simple.
His view of the past is skewed, things were never really available to regular people. There was always specialized professionals in the background handling the details. Except for a breif period in the late 80's and early 90's during the height of the PC revolution. Those machines though were a great leap backward in terms of what the limitations were as compared to the mainframe, and in leaving those limitations like (single user) behind we have put all the complexity back in.