I don't suspect that his "dark" feeling came from prescience about the impending dotcom crash. Locking a fledgeling business into a $30M lease should feel dark in any economy.
This sort of activity was very common during the dot com days. I witnessed a startup with a barely functioning product spend over $2 million upgrading their office space after raising close to $30 million. 3 years later it was "acquired" for a fraction of the investment, of course.