Cash App can send you a Form 1099-K, but only through a Cash App Business account. Personal transfers between friends and family don’t trigger one. For 2026, the federal threshold for a Business account is more than $20,000 in gross payments and more than 200 transactions — both conditions required. A handful of states set … Read more
If you sell a personal item for less than you originally paid, that loss generally isn’t deductible. But the sale doesn’t create taxable income either. A Form 1099-K reports gross payments — it doesn’t know what you paid for something, and it doesn’t calculate your gain or loss. Sell something for more than you paid, … Read more
Yes, but only above a specific threshold. That threshold is $20,000 in gross sales and more than 200 transactions — not $600. Some 2026 content claims the threshold “dropped to $600” this year. That’s backward. The federal rule actually moved the other way: legislation passed in 2025 restored the higher $20,000/200-transaction standard after years of … Read more
Yes. Airbnb can send you a Form 1099. But which form — and which threshold applies — depends on the type of payment. For ordinary reservation income, Airbnb issues a Form 1099-K. The 2026 federal threshold for that form is more than $20,000 in gross payments. It also requires more than 200 transactions in the … Read more
No — you generally can’t write off your monthly car payment itself, even if you use the car entirely for work. That surprises a lot of freelancers, because people almost universally confuse “car payment” with “car deduction.” What you can actually deduct depends on which method you use: either a standard rate per business mile … Read more
Yes — if your income changed materially during 2026, you can generally adjust your final estimated tax payment, due January 15, 2027. But whether you actually need to pay more (or can safely pay less) depends on four specific numbers: your projected 2026 tax, any withholding you have, what you’ve already paid in estimated payments, … Read more
If today — September 15, 2026 — came and went without your third-quarter estimated tax payment, nothing catastrophic happens immediately. The clock on a penalty does start running the moment the deadline passes, though. The fix is almost always the same: pay what you owe as soon as you can. The penalty grows based on … Read more
A rideshare or delivery driver can receive $4,000 in qualified tips over the year and still not deduct all $4,000 of it under the federal “no tax on tips” deduction. Self-employed workers face two separate caps: a flat $25,000 annual limit, and a second, less-discussed limit tied to the net income of the specific business … Read more
Venmo will send you a Form 1099-K only if the payments you received for goods and services cross $20,000 and exceed 200 separate transactions in the same calendar year. Both conditions have to be true, not just one. Venmo’s own tax help pages confirm that this is the current federal threshold for 2026. A meaningful … Read more
Two people each earn $80,000 this year. One gets it through a W-2 paycheck. The other invoices it as a 1099 freelancer. Ask most people which one pays more in payroll-type taxes, and they’ll say the freelancer — self-employment tax has a reputation as the expensive one. Run the actual numbers, and the freelancer comes … Read more