There are two ways to look at this investment, imo.
He is very positive about the future of the company and he wants more equity.
Or the company is having financial problems and he is not getting paid by the company--so he uses his own savings to fund the company--gets more equity--and gets himself paid.
Sure, he has to have some confidence in the future, but this financing clearly shows that he is the "investor of last resort". No outside financing was possible.
Just some thoughts.
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