he just exposed a weakness in your strategy. What if other VA’s have friends & family log on, accumulate free earnings and cash out using different ip’s and addresses? Theres got to be a more secure, automated hands off way to handle this. Also, official lotteries & contests have legal language like employees and family of employees are ineligible to participate or receive prizes. Unless you explicitly have a legal contract stating that, it’s possible it wasn’t illegal. Technically you gave him $100 to give out and he fulfilled that task… to himself. I’d consider talking with a lawyer to understand your situation and ensure you have all bases covered.