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What about his job prevents him from being open about it.

Watch out for IP clauses in his employment contract that mean his employer is now your uninterested business partner.

He works for a large corporation that prevents him (has him sign a clause) from having outside businesses. That, plus they are in downsizing mode, so he figures if they catch wind that he is hoping to eventually leave by having the side business, this just gives them cause to boot him now.

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