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My question is what steps can I take to keep more money in my pocket when tax time comes?
Unless you are raising VC money don't do a C since its double taxation.
Then make a board resolution that the following personal expenses are covered by the company for business use: car payment, gas, life insurance, gym membership, golf membership, boat payment, etc.Be very careful- some of those would be counted as income and subject to income & payroll taxes.
Never ever deduct your house or part of it for business, big red flag for an audit.
If you declare on your taxes that you have a offshore account your odds of being audited are almost guaranteed.
its all about risk/reward
I do my own taxes. The software out there today is pretty good at finding all the potential write-offs and tax breaks you might be missing.
Either way I am setting up IRA's on my own and my goal is to build off this income.
Unless there are some seriously compelling reasons to reside in the US, assuming you are in the US, then there are some very favourable jurisdictions around the world that would welcome you with open arms...assuming you do everything from a laptop!