I'm an accountant during the day and and a Blackhatter after 5pm, I wish I have a 10 gallon black hat and a fake mustache to wear when I'm on my computer at home. I'm currently making some money BlackHat Style and I need to plan my taxes for when I scale up so I don't get fucked. These are some ideas and advice that I'm putting together for myself so I can plan as I go. Please see if any of these will help you. 1. If you're still a sole proprietor I suggest to switch over to S-Corp. To minimize liability from your blackhat activities. Tax benefit: Sole proprietor have to pay a self-employment tax of 15.3% on your earnings. Incorporate your business and elect SubChapter S status. You can then pay yourself minimum wage (only this gets tax at 15.3%), the rest of your income can be "distribution" which is only subject to your personal income tax. 2. Write off everything, your phone bill, your internet bill, your CL posting fees, portion of your rent and utilities use toward your home office. 3. Move over seas to tax heaven countries: Move to Canada (I know it sux but they give you a 5 years immigrant trust that's tax free), and a lot CPA networks won't think that you're in some underdevelop country trying to scam people. * Please share other ideas, I will try to post more ideas later.