094R | 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.

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