I've used TurboTax Self-Employed for my Poshmark business for the past 2 years and it walks you through everything pretty well. It asks specific questions about online selling platforms and has sections for all the deductions another commenter mentioned above. It's not cheap but worth it for me because it saved me from making mistakes.

It's actually real! While there's no specific form just for stolen property, the IRS guidance explicitly states that stolen property must be reported as income. Publication 17 has historically mentioned this requirement. The IRS doesn't have a "stolen items" line, but they do expect you to report it as "Other Income" on Schedule 1 of Form 1040. It's one of those bizarre tax code realities that exists because the tax system is designed to collect revenue from all income sources, regardless of how that income was obtained.

Completely different situation. Roth IRAs are personal accounts you set up outside of work - they'd never show on your W-2 because that's just for employer-related income and deductions. Your W-2 wouldn't show anything about a Roth IRA contribution.

Oh wow, I hadn't even thought about the 1099 issue. None of my influencers got anywhere near $600 worth this year (most just got a single unit), but that's great to know for future reference as we scale up. For the bars and restaurants, I do have documentation including emails where we discussed them featuring my product and trying it out with customers. Would these emails be sufficient documentation, or should I be getting something more formal?

Your emails discussing the promotional arrangement would be a good start, but I'd recommend taking it a step further. Create a simple one-page "promotional agreement" that outlines what you're providing and what you expect in return (even if it's just consideration/feedback). Have the bar manager or restaurant owner sign it, even if it's just electronically. Also, take photos of your product on display or being used in these establishments as additional proof of the business relationship. The IRS loves visual evidence. And if any of these places end up featuring your product on their menus or social media, save screenshots as further documentation of the business purpose. This kind of documentation makes your case much stronger if you're ever questioned about these promotional expenses.

Thanks for this advice! I hadn't thought about tracking them separately from the beginning, but that makes so much sense. I'll create a separate category in my tracking spreadsheet for promotional items going forward. And great point about the shipping costs! I've been paying to overnight some samples to certain influencers to meet their content schedules, so that's definitely adding up. I've kept all those receipts but wasn't sure if they would fall under shipping or marketing expenses.

Those shipping costs for promotional samples would definitely fall under marketing expenses, not shipping expenses. Since the shipping is directly related to your promotional activities, it should be categorized the same way as the samples themselves. Just make sure to keep those overnight shipping receipts tied to your promotional sample records - maybe add a "shipping cost" column to your tracking spreadsheet so you can easily see the total promotional expense per recipient (sample cost + shipping). This will be really helpful if the IRS ever questions the business purpose or total amounts.

6 This is actually a common issue, especially with crypto or newer stocks. When you see "cost basis not reported to the IRS" on your 1099-B, you still need to enter your actual cost basis in FreeTaxUSA. The IRS requires you to report the correct information even if your broker didn't provide it to them. In FreeTaxUSA, when entering these transactions, there should be a checkbox or option to indicate "Basis not reported to the IRS." Make sure to check this and then enter your actual cost basis. You'll want to keep records of your purchase price in case of an audit.

Great question! For me, it took about 2-3 hours to enter around 30 transactions manually, including time to cross-reference my purchase confirmations. I'd recommend setting aside at least 4-5 hours if you have a similar number of trades, especially since it's your first time - you'll want to double-check everything as you go. The good news is you can save your progress in FreeTaxUSA and come back to it later if you need a break. I actually split it across two sessions because I got tired of staring at numbers! Also, having a calculator handy helped me verify some of the gain/loss calculations, even though FreeTaxUSA does the math automatically. One tip: start with your biggest transactions first since those have the most impact on your taxes. That way if you do need to take a break, you've gotten the most important ones entered already.

It really depends on how many transactions you have! For me, I had about 30 trades and it took roughly 2-3 hours to enter everything carefully, including double-checking all the dates and amounts against my Robinhood statements. If you have more transactions, I'd definitely recommend setting aside more time - maybe plan for 5-10 minutes per transaction if you're being thorough. The first few take longer as you get familiar with FreeTaxUSA's interface, but you get faster as you go. One tip that sped things up for me: I created a simple spreadsheet first with all my transaction data organized before I even opened FreeTaxUSA. That way I wasn't constantly switching between the tax software and my Robinhood documents. Made the whole process much less stressful!