Original wiki usage of this phrase was in the CowboyCoding page to refer to a group of cowboys working together.

''It is inappropriately disparaging to companies that had to start in a garage-like place, where the workers may not be cowboys.  I do some work in a basement, and yet we don't just cowboy through everything.''

Did AppleComputer count as a garage shop enterprise? Did HewlettPackard? If they were, at what point did they cross over to become "respectable"?

''Is Apple respectable again? I guess the iMac did it. Thankfully.''
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From CowboyCoding:

	 :	 Here again, some cowboys hang out together, often forming GarageShopEnterprises, sometimes, though rarely, with outstanding results. Apple might be an example.
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See also DevelopmentTeamModels
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Sony where also originally a backyard enterprise in Tokyo after World War II.