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The IRS is cracking down on side hustle income, and most people don’t get in trouble because they HAVE a side hustle. They get in trouble because they file it sloppy. This video breaks down the biggest side hustle tax mistakes that trigger IRS mismatch letters, and the simple system to stay compliant without overpaying. We cover freelancing + gig work + online selling. What you’ll learn: What “IRS crackdown” really means (data matching + mismatch letters) 1099-K vs 1099-NEC (and why the form is NOT your profit) The biggest 1099-K reporting mistakes (gross vs net, fees, refunds, shipping, COGS) The “no 1099” myth (and why it can still create a tax bill) The write-offs people mess up most (mileage, home office, meals, “content expenses”) Schedule C red flags (losses + hobby vs business issues) Estimated taxes: how to avoid the April surprise A simple weekly system: separate account + tax bucket + clean records CHAPTERS 00:00 IRS “crackdown” explained 00:51 How the IRS matches side hustle income 01:51 1099-K vs 1099-NEC (what they mean) 02:58 Mistake #1: “No 1099 = no taxes” 04:18 Mistake #2: 1099-K is gross, not profit 05:48 Mistake #3: threshold confusion + state traps 06:57 Mistake #4: personal payments + selling old stuff 08:08 Mistake #5: sketchy write-offs + no records 11:56 Mistake #6: hobby vs business + loss red flags 10:43 Mistake #7: estimated taxes (avoid April) 12:58 Mistake #8: W-9 issues + mismatches 13:38 Mistake #9: digital asset/crypto reporting (high level) 15:23 The simple system to stay compliant If you want a follow-up walkthrough of a real Schedule C example (income, expenses, mileage, estimated taxes), comment: SIDE HUSTLE TAXES. This video is for informational purposes only, not financial advice. #SideHustle #Taxes #1099K #IRS #PersonalFinance