I made a personal loan to the company in august 2019 of 14K. My bookkeeper put it in as opening balance equity. I want to pay myself back now. How do I do that?

Question 1  What type of entity is your company

LLC or Sole proprietor you do not loan money to yourself and it is all owner contribution (equity in) when "loaned" to company and owner draw (equity out) when you "pay" yourself. It never should have been Opening Balance Equity unless it was in the company prior to keeping the books in QB.  At end of first year of operation OBE moves to regular owner equity with adjustments for profit/loss passed through to personal return.

Subchapter S > you would own shares and loans to the company have to be classified as loans just as if they were from a bank, In this situation you would be repaying a standard loan and it never should have been recorded as equity at all

Hi There!  Thanks for the response.  

My company is an S Corp.  So sounds like it should have been entered in as a loan

Yes, as a Subchapter S corporation you start your company with shares that are valued initially on your purchase of same = essentially your capitalization of the enterprise.  But loans to or from the shareholders should be classified as loans https://www.upcounsel.com/loans-to-shareholders-s-corp

I would go back and change the equity transaction to a loan and now repay the loan. But be careful that the company does not have a loss such that this repayment is treated as ordinary income to you and not simply a repayment.

I have a simple sole proprietorship--I do not have a corporate entity of any type. I deposited personal funds into my business account once during the tax year to cover expenses when I lacked cash flow.  When preparing my return, do I report this deposit as income to the business? It would seem that would result in double taxation, since I've already been taxed on my personal income from the past. Or should it be characterized as a loan? Is there a difference? Or is it a non-event for tax purposes? Any guidance appreciated!