He didn't buy his entire infrastructure/ecosystem last week. He almost certainly accumulated a fair number of Apple devices and then had chosen to upgrade them

He didn't buy his entire infrastructure/ecosystem last week. He almost certainly accumulated a fair number of Apple devices and then had chosen to upgrade them all to Catalina/iOS 13 and then encountered problems. These problems could have been avoided by not immediately upgrading all devices the latest software release. Instead he could have opted to roll out upgrades devices by device thus limiting the scope of any problems.