Do I have to pay taxes for selling concert tickets on StubHub?

What about if I sold tickets at a loss? I bought some tickets for $500 but could only sell them for $420 on StubHub because the artist wasn't as popular as expected. Can I deduct that loss somehow?

For ticket sales at a loss, unfortunately you generally can't deduct that loss on your taxes. The IRS considers personal concert tickets a personal expense, not an investment, so losses aren't deductible. It's one of those one-way streets where profits are taxable but losses aren't deductible. If you were running an actual ticket resale business (with regular activity and intent to make profit), that would be different - then you could potentially deduct losses as business expenses. But for occasional personal ticket sales, losses typically can't be deducted.

Does this taxr.ai thing actually work for more complicated situations? I have some freelance income plus I sold a bunch of stuff online plus some crypto transactions. Does it handle all that or is it just for basic tax questions?

I'm kinda skeptical about AI tax tools. How accurate is it compared to like going to a real tax professional? I don't wanna get audited because some AI gave me wrong info.

It definitely handles more complex situations! I actually had some freelance income alongside my ticket sales, and it walked me through exactly how to report everything correctly. It can analyze documents from multiple income sources and give you a complete picture of your tax situation. The accuracy has been really impressive in my experience. It's built on the same tax regulations that professionals use, but it can process your specific situation instantly. I was worried about the same thing, but the guidance it gave matched exactly what my friend (who uses a CPA) was told about a similar situation. They also provide explanations with references to specific tax codes so you can verify yourself.

Wait how does this actually work? Do they hack into the IRS phone system or something? Seems kinda sketchy that they can somehow get you through faster than waiting on hold yourself.

Yeah right, there's no way this actually works. I've been trying to reach the IRS for 3 months about a missing refund. Nobody can magically get through their phone system. This sounds like a scam to get people's money who are desperate to talk to the IRS.

It's actually completely legitimate! They don't hack anything - they use an automated system that waits in the phone queue for you, then calls you when your turn is coming up. Think of it like a placeholder service. They just have the technology to navigate the IRS phone tree and wait on hold so you don't have to. Nothing sketchy about it at all - you still talk directly to the actual IRS agents. The service just eliminates you having to sit there listening to hold music for hours. I was skeptical too until a coworker recommended it. You still wait your actual turn in line, you just don't have to be the one physically waiting on the phone.

Wait I thought the 1099-K threshold was $600? I've been stressing all year trying to keep my PayPal under $600 from my little Etsy shop. Are you saying it's actually $5000 now???

The PayPal 1099-K threshold has been a moving target! It was supposed to drop to $600, but there have been multiple delays. For 2024 transactions (what you'll file in 2025), the IRS announced they're keeping the threshold at $5,000. So you don't need to worry about getting a 1099-K for PayPal transactions under that amount. However, the IRS has said they still plan to eventually implement the $600 threshold in future years. But for your 2024 income, you're good with the $5,000 threshold. This gives small sellers a bit more breathing room before the lower threshold kicks in.

While it's true that the IRS might not immediately know about small unreported amounts, technically you're still legally required to report all income regardless of whether you receive a form. The tax system operates on voluntary compliance. I understand the temptation to skip reporting small amounts, but it's not something I'd recommend. Even though audit rates are low for average taxpayers, developing good habits early in your tax life is important. Plus, the peace of mind knowing you're fully compliant is worth it. As you earn more in the future, maintaining consistent accurate reporting becomes even more important.

Yeah that makes sense I guess. I just never understood how they expect people to keep track of every little thing when the tax code is so complicated. Like if I sell my old phone to a friend for $50 more than I paid for it, am I supposed to report that too? Where do you draw the line?

I totally get the confusion about what needs to be reported! The general rule is that any profit from selling personal items is technically taxable income, even something like your phone example. However, there are some practical exceptions - if you sell personal items for less than you originally paid (which is usually the case with used phones, furniture, etc.), then there's no taxable gain. The IRS does have something called the "de minimis" concept where they focus enforcement on more significant amounts, but there's no official threshold that says "ignore income under $X." For occasional small sales like concert tickets or selling old stuff, most people report them if they made a profit, especially if they're already filing a return for other income. I think the key is being reasonable - if you're regularly buying and selling things for profit, that's starting to look like a business. But one-off sales of personal items? Use your judgment, but when in doubt, it's usually better to report it.

This is such great advice about keeping records! I wish I had started doing this earlier. I'm pretty disorganized with my finances and just kind of wing it when it comes to tracking money stuff. Do you have any tips for what exactly to track? Like should I be saving receipts for everything or just the big purchases? Also, how do you handle tracking cash transactions? Sometimes I do odd jobs for neighbors and they pay me in cash, so there's no digital record like with PayPal or Venmo. Do you still put those in your spreadsheet even though there's no "proof" of the transaction?

Great question about tracking cash transactions! I definitely include all cash payments in my spreadsheet, even without "proof." The IRS expects you to report all income regardless of whether there's a paper trail, so it's important to be honest about cash work. For tracking, I keep it simple - I note the date, what the work was, who paid me, and the amount. For cash jobs, I usually write it down in my phone notes right after I get paid so I don't forget. Then I transfer it to my spreadsheet weekly. As for receipts, I save everything for business-related expenses (like if you buy supplies for a gig) since those might be deductible. For personal purchases, you don't need to keep receipts unless it's something you might sell later (like those concert tickets). The key is just being consistent with whatever system you choose! Having good records also helps if you ever need to prove your income for things like student loans or apartment applications. It's been super helpful for me beyond just taxes.

This is exactly the kind of practical advice I wish I had when I first started dealing with taxes! You're absolutely right about the standard deduction threshold - it's such a relief to know that small amounts like this aren't going to trigger any issues with the IRS. I'm also 18 and just starting to navigate all this financial stuff. One thing I've learned is that it's better to be overprepared than underprepared. Even if you don't need to file this year, having good documentation habits will serve you well as your income grows. Plus, if you ever need to apply for financial aid or loans, having organized records of your income can be really helpful. Thanks for sharing your perspective - it's nice to hear from someone in the same age group who's figured some of this out already!

This is really helpful advice, especially about treating it as a learning opportunity! I'm also just starting to figure out all this tax stuff and it's honestly pretty overwhelming. One question I have - you mentioned keeping detailed records, but what's the best way to organize everything? Like should I be keeping physical copies of receipts or are digital screenshots good enough? And how long should I keep these records for? I don't want to be hoarding paperwork forever but I also don't want to throw away something important. Also, when you say "good documentation habits," what exactly does that mean in practice? Is it just about saving receipts or is there more to it? I want to make sure I'm setting myself up for success as I start earning more money.