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How can a guy living the high life with his own company lose it all?

It can be anything also this guy not popular he an arrogant guy who has no loyalty except to his company.
We get off to the rhythm of the trigger and destruction. Fallujah to New Orleans with impunity to kill. We are the hidden fist of the free market.
We are the ink, we are the quill.
[The Ink And The Quill (Be Afraid) - Anti-Flag]




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The company goes bankrupt? He's found to have been doing tax fraud? He's fiddled his accounts?

Basically anything that severs his connection with the company; like you said, if the company is all he has loyalty too, then the conflict can be to remove the company, or at least the standing of the company. Then he loses everything.
Nate wrote:And if YWS ever does become a company, Jack will be the President of European Operations. In fact, I'm just going to call him that anyways.



It had a perfectly round door like a porthole, painted green, with a shiny yellow brass knob in the exact middle. The door opened on to a tube-shaped hall like a tunnel: a very comfortable tunnel without smoke, with panelled walls, and floors tiled and carpeted, provided with polished chairs, and lots and lots of pegs for hats and coats—the hobbit was fond of visitors. The tunnel wound on and on, going fairly but not quite straight into the side of the hill —The Hill, as all the people for many miles round called it—and many little round doors opened out of it, first on one side and then on another.
— JRR Tolkien