Other details left out are that at the time no one would lend the company money or finance without steep discounts to share conversions. The company was near bankruptcy at the time which made the move even more risky. Also at the time the loan only made him first in line upon liquidation of assets and discharge of debts. So, need to maintain the context of the times when he loaned money and the share price ranged from around $1 to just above 10 cents. We need to look at all of it, and not just the sweetheart deal it appears to be 6 years later.
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