While I enjoy your premise of Moby Dick as being a good parable for security professionals as well as modern capitalists, your?re really pushing the metaphor to fit your concept. And you don't need to, Melville covers the spectrum of management good and bad. Ahab was very open minded in his approach -- he hired the best with no prejudice to personality or religion. His crew were upstanding men like Starbuck (who never drank coffee, btw) to skanks like Stubb. He hired drunkards, pagans and savages because they were the best at what they did not because they fit any preconception of what good workers were supposed to be or look like. His management sin wasn't an obsession over one security approach; it was an obsession with a vendetta that was indifferent to the shareholders and the crew.

If it were a modern tale, he'd be going after a ?Uber Hacker? that showed him up while Starbuck would be complaining about all the other security breaches being ignored just as Ahab ignored the leaking kegs of spermecetti in the hold in order to forge on after his White Whale.

Moby Dick is loaded with management parables that better portray your point of obsessing on one thing to the disregard of other things. These obsession are not due to monomania as much as ignorance: the Rose Bud whose ignorant captain was a former perfumer and doesn't know dick about whaling and wastes time trying to harvest rotting whales; the Jungfrau captained by the incompetent Derick De Deer who doesn?t even have enough spermecetti to light a lamp and who can't get out of the way of Ahab's more competent crew; The captain of the Town-Ho who is also a shareholder who treats his crew like pumping machines because he doesn't want to do maintenance to fix the leaks and ends up with a crew mutiny who finally desert him. All of these captains were White Hats who did wrong because they didn't know what they were doing despite their convictions. In Melville's world, it seem Grey hats were White Hats with experience. The leaders of the Pequod were all Grey Hats -- they chose to put their personal beliefs aside to do the job well; thus such diametrically opposed mates as Starbuck and Stub could work well together.

Ahab was the supreme technologist and was willing to use anything to achieve his goal -- he had a special harpoon made and had all of his harpooners: indian, pacific islander, and islamic make oathes to bless it -- something your typical Nantucker Christian would have never done. Ahab was a greyhat turned black in his obsession with getting back at the hacker that spited him rather than doing the job he did so well. He let it be known he was willing to even kill good Starbuck if he got in his way. He let everything go to hell for revenge rather than being practical about it like the commander of the Enderby who lost his arm to the White Whale and knew it was better to go after other fish and make a profit than mess with Moby again.

So yes, Ahab was a monomaniac. His monomania was in purpose not technology: Ahab used any tech that worked. And yes he was over come by hubris because he was damn good at what he did. That hubris allowed his monomania to take him on a vendetta that obliterated all other purpose and in the end obliterated everything.



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