Surprise, there are more environments that you could do web development on and quite a few of them are a lot easier to master than the one you describe.
Surprise, there are more environments that you could do web development on and quite a few of them are a lot easier to master than the one you describe.
Also important is scalability. Some 'development environments' that are easy to get started with have bad reputations for 'scalability'.
Another practical issue is, is the guy just a developer in a group where he can draw on others in the group or is he really, now, and during most of his development, just one guy and not funded and has to do nearly everything alone? To do it all as just one guy means he needs to know a LOT about computing a bit far from just Web development alone.
Actually, I omitted a lot: For a Web startup, usually need something like relational database, e.g., SQL Server. If the startup gets very far into production, then he will need some background in SQL Server management and administration, e.g., performance, backup, and recovery, and I omitted such topics.
I gave a description of some of what is important if developing on Windows. Here at HN, Windows is not the most popular option. But if you have some alternatives in mind, then describe them,