One man as a leader/guru of a larger group kinda misses the point, which is technological enhancement of individual actions, or even abilities (think cyborg). But all such scenarios miss the numbers factor: what one man has access to, others also are accessing. There is more going on than any Horatio's philosophy or contacts know about. So the responses to individual actions will come out of all sorts of left fields he/she didn't foresee.

That is, complex systems have lots of response modes and feedback cycles.

Not that they can't tip into disaster or massive reorganization, but it ain't as easy as it looks from any POV within the system. Negative feedback will have its say.