Keep in mind the $20k threshold for Cash App (and most other payment processors) changed recently. For 2022 tax year it was $20k AND 200 transactions, but for 2023 tax year it was supposed to be $600, then they postponed that. Double check the current threshold so you know what to expect!

This is really helpful info everyone! I'm in a similar boat but with PayPal instead of Cash App. One thing I learned the hard way is to keep really detailed records of what each payment was for, especially if you're mixing business and personal use of these apps. The IRS wants to see that these were legitimate business expenses, so I started keeping screenshots of the payment descriptions and matching them to invoices or work orders. Makes the whole 1099 process way smoother when you have everything organized from the start instead of trying to piece it together later. Also agree 100% on getting that W-9 ASAP - I had one contractor who gave me wrong info and it was a nightmare to fix after I'd already filed. Better to verify everything now while there's still time!

Don't forget that online sports betting might also have state tax implications depending on where you live! Some states treat gambling wins/losses differently than the federal government.

Just went through this exact situation last month! Here's what I learned after doing a ton of research and talking to a tax pro: You definitely need to report ALL gambling winnings as income, even without W2-Gs. The good news is you can combine everything - so add up all your wins from FanDuel, DraftKings, bet365, and Fanatics and report that total on Schedule 1 as "Other Income." For losses, you can only deduct them if you itemize deductions on Schedule A, and only up to the amount of your winnings. So if you won $2000 total but lost $3000, you can only deduct $2000 in losses. Most importantly - start keeping detailed records NOW for next year! Date, platform, bet amount, win/loss amount for every single wager. The sportsbooks usually let you download your full betting history, so grab those files while you still can for this tax year. Trust me, you don't want to be scrambling next year trying to reconstruct everything again!

I went through this exact same situation last year and can confirm that yes, your realized losses from selling individual stocks absolutely can offset the capital gain distributions from your mutual funds! The key thing to understand is that the IRS treats all capital gains and losses as one big pool when calculating your net position. So those capital gain distributions from your mutual funds (which will show up in Box 2a of your 1099-DIV) can be directly offset by the losses from selling your tech stocks. Here's what helped me get organized: Your mutual fund distributions go on line 3b of Form 1040, while your realized gains/losses from stock sales get reported on Schedule D first, then flow to line 7. But don't worry about keeping them separate for offsetting purposes - the tax software automatically nets everything together. One tip from my experience: keep good records of what you sold and when, especially if you're thinking about buying back any of those positions. The wash sale rule can bite you if you repurchase within 30 days of the sale. I almost lost some of my tax benefits because I bought back a similar position too quickly. The good news is those "bad tech picks" might actually end up saving you money on this year's taxes! Sometimes our investing mistakes can at least provide some tax relief.

Yes, absolutely! Capital gain distributions from mutual funds can be offset by realized losses from selling other positions. This is one of the key benefits of tax-loss harvesting. Here's how it works: Your mutual fund capital gain distributions (reported in Box 2a of Form 1099-DIV) are treated as long-term capital gains regardless of how long you've owned the fund shares. These distributions get reported on Schedule D and flow to line 3b of your Form 1040. Your realized losses from selling individual stocks also go on Schedule D using your 1099-B forms, then flow to line 7. The IRS nets all your capital gains against all your capital losses - it doesn't matter what the source is. So if you have $5,000 in mutual fund distributions and $7,000 in stock losses, you'd have a net capital loss of $2,000 that you can use to offset other income (up to $3,000 per year), with any excess carrying forward to future years. This is actually a common tax-loss harvesting strategy - when you get hit with unexpected mutual fund distributions, you can strategically sell some underperforming positions to offset the tax impact. Just watch out for the wash sale rule if you're planning to repurchase any of those positions within 30 days!

This is exactly the situation I was in last year! Made about $3,200 from my small pottery business and was so confused when no 1099 showed up. One thing that really helped me was creating a simple business expense tracker from day one this year. I wish I had done it sooner because I probably missed some deductions last year. Now I track everything - clay, glazes, kiln electricity usage, even the portion of my garage I use as a studio. The Schedule C form in TurboTax is actually pretty straightforward once you find it. Just make sure you categorize your expenses correctly (Cost of Goods Sold vs Business Expenses) because it can affect your final tax calculation. And definitely don't forget about tracking your mileage to craft fairs or supply stores - those trips add up! Also keep in mind that once you start making regular income from your craft business, you might need to make quarterly estimated tax payments next year to avoid penalties. The IRS doesn't like waiting until April for their money when you're self-employed.

As someone who's been helping folks with tax issues for years, I just want to emphasize a few key points that haven't been mentioned yet: First, make sure you understand the difference between gross income and net profit when reporting your Etsy business. You report your total sales as income, but you can deduct legitimate business expenses to reduce your taxable profit. This is crucial because many new business owners get scared seeing their total sales number without realizing they can offset it with expenses. Second, if this is your first year with self-employment income, be prepared for the "self-employment tax shock." This is the 15.3% tax that covers your Social Security and Medicare contributions (normally split between you and an employer). It's on top of your regular income tax, so factor that into your planning. Finally, since you're clearly committed to this business, I'd strongly recommend opening a separate business checking account next year if you haven't already. It makes expense tracking SO much easier and provides clear separation between personal and business finances, which the IRS appreciates if you ever get audited. Good luck with your jewelry business! The fact that you're being proactive about properly reporting your income shows you're taking this seriously, which is exactly the right approach.

Make sure you explore all possible deductions/credits to offset some of this conversion income! Unemployment often makes people eligible for credits they wouldn't normally get. Check if you qualify for the Earned Income Credit, education credits if you took any classes, or increased medical expense deductions (threshold is lower when income drops). Also, since you were laid off, don't forget to deduct any job search expenses that might be eligible. Every little bit helps when facing a big tax bill from Roth conversions!

I'm really sorry to hear about your situation - getting hit with unemployment and a massive tax bill at the same time is incredibly stressful. Since you can't undo the conversion, here are a few additional strategies to consider: First, if you haven't already, make sure you're maximizing your 2023 deductions. Since you were unemployed for part of the year, you might qualify for larger medical expense deductions (they need to exceed 7.5% of AGI), and any charitable contributions you made could help offset some of the conversion income. Second, consider whether you have any capital losses in taxable investment accounts that you could harvest to offset some of the ordinary income from the conversion. While capital losses primarily offset capital gains, you can use up to $3,000 per year to offset ordinary income, with any excess carrying forward to future years. Finally, when you do speak with the IRS, emphasize your unemployment situation. They're often more willing to work with taxpayers facing genuine financial hardship. Document everything about your job search efforts and financial situation - this will support any hardship claims. The combination of an installment plan, penalty abatement if you qualify, and maximizing all possible deductions should help make this more manageable. Hang in there!