Deducting side work sole proprietorship expenses from regular employment earnings?

Question

I have a day-job which gets me a salary. I'm about to start some websites on the side with the intention of making money off advertising. For the time being, I plan to remain an unregistered sole proprietor. No LLC etc.

I would wager that many of you are living with similar arrangements.

In your experience, does the IRS consider it acceptable to deduct website hosting costs etc. as "business expenses" from one's income (i.e., day-job income), while the websites aren't generating any income? (There's a good possibility that mine won't generate any income for a few years... or worst case: ever.)

Answer 1

You can see some IRS info on distinguishing a business from a hobby here. Nolo also has some info.

The upshot is that you can only deduct losses if your activity is, in the judgement of the IRS, a for-profit endeavor. You don't have to make a profit right away, or make a profit every year, for it to be a for-profit endeavor, but you have to be able to convince the IRS that you're doing it in order to (eventually) make a profit, not just for fun. You can't just keep deducting the losses year after year if (as in the worst case you suggest) it never makes a profit and doesn't seem to have any chance of doing so.