Most people leaving W-2 jobs have no clue they'll owe the IRS thousands in quarterly payments—and they find out the hard way. Brad walks through exactly how to calculate and avoid penalties on estimated tax payments, including the safe harbor provision that lets you use last year's tax bill as your baseline. The episode also tackles the hidden cost of "free" prizes: one listener won a $20,000 car, sold it for $15,000, and still owed a $20,000 tax bill. Chapters Introduction to Entrepreneurship & Taxes [00:00:00] Frugal Win of the Week [00:01:40] Understanding Tax Implications of Non-Cash Prizes [00:06:59] Case Study of a Side Hustler [00:12:40] Best Practices for Estimated Payments [00:15:00] Conclusion and Key Takeaways [00:51:20] Key Takeaways Reserve funds for taxes based on the prior year's liability to prepare for upcoming obligations. [00:19:04] Separate tax reserves in a dedicated bank account to prevent last-minute panic. [00:31:09] Calculate expected tax liabilities to avoid penalties by understanding the safe harbor provisions. [00:19:22] Winning non-cash prizes often leads to unexpected tax liabilities. [00:09:27] Don't forget your state tax obligations as a self-employed individual. [00:33:00] Terminology Quarterly Tax Payments [00:10:22] – Payments made every three months to cover expected income tax liability. Safe Harbor Provision [00:19:11] – A tax rule that avoids underpayment penalties if certain conditions are met. Self-Employment Tax [00:12:55] – A tax consisting of Social Security and Medicare taxes primarily for individuals who work for themselves. Resources EFTPS.gov – Online resource for making estimated tax payments. [00:31:09] Related Episodes Episode 013: "Maxed Out: The Millionaire Educator" [00:51:07] Episode 016: "Waffles on Wednesday" [00:00:57]