094R | Transitioning to Entrepreneurship | A Case Study in Estimated Taxes

The logistics of estimating and paying taxes as an entrepreneur, Brad’s frugal win of the week, and emails from the ChooseFI community.

  • Brad and Jonathan are at FinCon in Orlando, Fl.
  • Brad describes his family’s frugal win of the week at Old Navy.
  • Review of the tax implications of winning a non-cash prize.
  • How do some entrepreneurs put themselves in a position to fail because of taxes?
  • Case study: how to make estimated tax payments as a new entrepreneur.
  • Brad wants to pay the least amount of money in taxes, but ensure that he definitely pays the minimum amount to avoid incurring penalties.
    • Knowing due dates and technicalities is important.
    • It’s key to have money set aside in case you do owe more at the end of the year.
  • What is the safe harbor provision?
  • If you have blended W2 and non-W2 incomes, you do have to estimate based on previous pay stubs.
  • Why would someone owe payroll tax?
  • Brad uses a different bank account to reserve money he thinks he’ll need for taxes, and uses an eftps.gov account to submit his taxes.
  • It’s important to know that you’ll owe a lot of money on April 15 every year.
  • Email from Ally reporting two life wins:
    • Keeping an inventory for what’s in her freezer by writing on the front like a white board.
    • Using checkboxes to keep track of the three things she accomplishes every day.
  • Is FI getting to the UK?
  • Playing with FIRE documentary has been submitted the film to Sundance.
  • Scott, writes an email, to explain how pursuing financial independence and information from ChooseFI has changed his life.

 

Link:

“How to retire in your FORTIES without earning a fortune” – Daily Mail

2 Replies to “094R | Transitioning to Entrepreneurship | A Case Study in Estimated Taxes”

Leave a Reply

Your email address will not be published. Required fields are marked *