He is <24 years old and his primary world view has been formed whilst "cloud" was the pinnacle of technical obviousness.
There's a pretty large range between Pinboard (10 000 customers, maybe? Two employees? Annual revenue in the range of $100k? I'm guessing here) and Rite Aid (109000 "associates", maybe 20 million customers, $26 billion revenue). More than five orders of magnitude, actually.