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Hmm. The article is a bit ambiguous. Does he mean he started out with only 1,000 in capital? Or did he only have 1,000 dollars in sales.

We had $1,100 total when we incorporated Esri.

Pretty clear in my opinion. They had $1,100 of capital and not of sales.

Yes, you're correct. Jack's family had given him $1000 in the early days.