“Bootstrapping” comes from the term “pulling yourself up by your own bootstraps.” That much you can get from Wikipedia.
In computing, a bootstrap loader is the first piece of code that runs when a machine starts, and is responsible for loading the rest of the operating system. In modern computers it’s stored in ROM, but I recall the bootstrap process on the PDP-11, where you would poke bits via the front-panel switches to load a particular disk segment into memory, and then run it. Needless to say, the bootstrap loader is normally pretty small.
“Bootstrapping” is also used as a term for building a system using itself — or more correctly, a predecessor version. For example, ANTLR version 3 is written using a parser developed in ANTLR version 2.
An example of bootstrapping is in some web frameworks. You call index.php (the bootstrapper), and then it loads the frameworks helpers, models, configuration, and then loads the controller and passes off control to it.
As you can see, it’s a simple file that starts a large process.