But because my anecdotes are just as good as anyone else's, the place where I started my career has plenty of 20-30 yr veterans in their IT department, and they are a warehouse company with an IT staff of over 200 people but their tech doesn't directly make them any money at all.

That's a long stable career in IT in a department bigger than what he wants the entire company to be where IT is a cost center. If you're limiting yourself to tiny tech companies, you're missing out on a lot. Maybe company size and products sold aren't necessarily a good indicator of your career success...?