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Interesting questions... , I think however there are, far more critical questions 'you' first must answer. Poorly phrased I'm sure but my brain works like this. What are the possible ramifications on my existing business? When you become an employer the 'rules' change. Sometimes dramatically. Payroll... payroll deductions for a,b,c, & d federally. e,f & g at lower levels of government. Who's taking care of all the paperwork? Ideally your accountant. Oh... don't have one of those well then your book-keeper. Oh.. that's you. Hmmmm adding how much time to an already too heavy workload which is why you're looking to hire in the first place... yes no? Oh... you already have a bookkeeper ..ok..and they want how much more money to take on this extra workload? And when it gets down to the bottom line because that indeed is what were talking about... the bottom line in straight dollars and cents. Are you going to end up with more dollars in your pocket and if you do will the increased compensation be 'worth' it? Ideally you'd have a business model where you could pump X$'s into a spreadsheet and come away with a pretty accurate indication of just what it all means in dollars and cents. Because who knows... after taking a brutally hard & cold look at the $$$ you may come to the conclusion that your money is better spent on a bookkeeper. You all but eliminate that part of your 'personal' workload (which you really don't like doing anyway) and the potential 'business' you're now avoiding becomes potentially, viable income. After you've determined the ramifications of 'possible methods' it then becomes a matter of your personal philosophy versus your ' [b]business[/b] reality.' The reality of a 'friendship' thrown into the mix will certainly at some point test that friendship...and that will come the first time, as the employer, you say... 'No... I want it done this way.' Is the money worth the friendship? Let him read this.
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