How do I file taxes on my single member LLc when it’s unprofitable but I’ve transfer $ to my biz account to pay for biz expenses?

Yo are talking apples and oranges. Capital gains are related to your basis not the form of payment. If you are a cash basis taxpayer, you pay taxes when you receive cash beyond your basis. We can help you with structure.

The income should be reported by the individual or business that provided the service and earned the income. If the 1099 is in your name, you could ask the issuing Company to change to the S-Corp if that is who earned the income. In the future, have a written agreement between your S-Corp and the Company you are providing service. Also, provide them with a Form W9, so they know where to report the 1099 income at year end.

NIcole is right. When I first started my business I thought I was saving money by doing my own bookkeeping. It took me much longer than it would take a bookkeeper - all time that I was not spending on marketing or billable activities. And in the end I made errors which made the initial work of the bookkeeper longer. I now have a consistent routine. My bookkeeper picks up all my material monthly and does my books in less than 2 hours. Very worthwhile.

There shouldn't be any tax consequences for the founders if you've made 83b elections--the election meant you paid tax already on the full value of the stock at the time of the election (presumably zero) even though it was subject to future forfeiture. If you sell newly-issued stock there should be no tax impact. If you sell your own common stock, you'd pay tax on the gain, but I doubt that is what you mean here. Of course, you should not take the free advice dispensed on Clarity and consult your own tax preparer--this is not tax advice.

If your concern is from an ethical standpoint or a concern over a segregation of duties, there is no problem at all having your tax person handling your bookkeeping. The bigger issue is something that few people understand about accountants. There are different specialties within accounting, and you should go to the right specialist for the right task. Tax accountants are experts in tax law, filling out tax returns and finding ways to minimize taxes. They must immerse themselves in the field to maintain their expertise. Financial accountants (which include bookkeeping) are experts in debits and credits and keeping all your transaction straight in your accounting software so that you can get good financials each month. Financial accountants have to immerse themselves in your day-to-day accounting so that they can keep it accurate and up to date. Full disclosure, this is the work that my firm specializes in, we don’t do any taxes. Because each type of accountant must immerse themselves in their individual fields of expertise, they don’t have the time to focus on the other expertise. Not that they are both not great accountants, they just have a different specialty. Here’s a good analogy. If you developed a heart condition, would you go see a neurologist? No, you’d go see a cardiologist. They are both outstanding physicians and know a lot about the human body, but the cardiologist spends all their time thinking about, studying, and treating heart conditions and is going to be the best equipped and most knowledgeable about treatments for your heart condition. The last point I’ll make is that tax work is very seasonal and requires incredible focus and incredibly long hours leading up to major tax deadlines. This is not only during the period from January to April 15th, but also leading up to major deadlines on August, September and October 15th. Companies I have worked with that used tax accountants in the past for their bookkeeping find during these periods their tax accountants are forced to put all other work besides taxes on hold until their tax work is complete. What often happens in these situations is that these company’s bookkeeping falls three or four months behind. This can be devastating for a small business that needs to know if they are making money or losing money on a very up to date basis. So my suggestion is to find yourself a good bookkeeper that can handle your books. Your tax person may even be able to suggest a good resource, and deep down may be glad to do so because her first love is taxes, not bookkeeping. My firm could likely handle the work as well. Hope my thoughts above are helpful and addressed your question, but feel free to reach out to me if you have any follow up questions.