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I've done the 1099 thing before. I had an accountant and my own LLC. I made sure to have a separate bank account that I dumped 30% of my billable time into. Each tax season I'd cut a giant check to the IRS.

I mean no disrespect to the "gig economy" people, but 1099 requires a lot of discipline. Most of them probably don't need to pay estimated taxes and instead will be cutting giant checks to the IRS each year. It requires a hell of a lot of discipline to stare at thousands of dollars of money sitting in your own bank account knowing you cannot spend that no matter what--that is uncle sam's money.

I wonder how many gig economy people wind up owing the IRS a ton of money. Especially when they have to pay self-employment tax on top of normal tax.

Plus I bet very good money 99% of them aren't paying state or municipal taxes. As a 1099 I had to pay Washington State B&O tax every year as well as some token amount to Seattle.



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