I have no idea who the top executives at a company like Trek are but I imagine they are "executives". It's hard for me to imagine anyone at Surly looking remotely like an executive. In my mind at least, they are people who ride bikes nearly every day like I do. They design their bikes for that niche. In that sense, the Surly people seem like one of us.

Now I'm sure the people at Jamis, Trek, Giant, etc. really like bikes but they are all over the place in terms of the types of bikes they make. There doesn't seem to be anything that really ties their models together, no underlying philosophy to use your terms. There's not much to distinguish an entry level road bike from Trek from an entry level road bike from Giant.

I think it's also worth pointing out that Rivendell and Surly both make steel bikes. Steel has a cult following of its own.

Personally I don't really have a brand loyalty but I get why Surly and Rivendell do. Neither one of them produce bikes that are really aimed at me at this point in my life. Maybe when I get a little older, care less about performance, and have a lot more disposable income, I'd find their bikes more appealing. On the other hand, I also like bikes built out of something that doesn't rust and that's not likely to change.

It's easier to develop a cult following when you are targeting a particular group of customers rather than having a wide variety of products to try to appeal to everybody.