Yes he doesn't seem to realize that the larger the app the harder it is to scale i.e. thousands of requests per second for a <1mb HTML5 app could be a serious scaling problem.
Not to mention his complete ignorance of the variable bandwidth of mobile devices.
No, it doesn't. Size of application can correlate strongly with complexity and thus number of queries to the server, but there is nothing that dictates a 1.44MB+ HTML5 application ever even touches a server.
We're talking about static files, right? If you're trying to scale those should be nowhere near your application server. They get served from a CDN and the size is completely irrelevant to technical scaling issues.
Money is easy. It's not part of the difficulty of scaling. 1000x the static traffic means 1000x the bandwidth heading to simple, independent, easy to load balance servers. Difficulty added per user: zero. Cost per user: the same or less.
There are many reasons to want small files, but scaling isn't one of them.
A one time cost in a universe where your app never changes, CDNs cost nothing, and browsers have perfect caches, and everyone ubiquitously uses the localstorage and app-cache html5 apis.
Not to mention his complete ignorance of the variable bandwidth of mobile devices.