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I went through almost the exact same situation last year with my PayPal 1099-K showing around $85K in transactions from sports betting activities. The key thing that helped me was creating a detailed spreadsheet that separated: 1) Actual deposits TO sportsbooks (not taxable income) 2) Withdrawals FROM sportsbooks (potential winnings) 3) Money transfers with friends (definitely not taxable) 4) Net gambling wins/losses by session The 1099-K is just PayPal reporting gross payment volume - it's NOT all taxable income. You'll only pay tax on your net gambling winnings (if any). Since you mentioned having net losses, you might not owe additional tax from gambling at all. For the friend situation, keep clear records showing when money was just passing through your account versus actual gambling activity. Text messages, Venmo descriptions, etc. can all serve as documentation. I'd recommend going with a CPA who has gambling tax experience rather than H&R Block. The cost difference was worth it for the peace of mind and proper documentation.
This is really helpful advice! I'm curious about the spreadsheet approach you mentioned - did you create this manually or use any specific software to track everything? Also, when you say "net gambling wins/losses by session," how granular did you get? Like did you track individual bets or just daily totals? I'm trying to figure out the best way to organize everything before I sit down with a CPA.
I'm dealing with a very similar situation right now! Got my PayPal 1099-K showing about $67K in transactions, mostly from DraftKings and some peer-to-peer transfers for betting pools with friends. One thing I learned from my preliminary research is that you absolutely need to keep the friend transactions separate from your actual gambling activity. The IRS doesn't care about money that just flows through your account - they only want to tax actual gambling winnings. I'd definitely lean toward finding a CPA with gambling tax experience. I called around to a few tax preparers and was shocked at how many weren't familiar with the new 1099-K reporting requirements or how to properly handle online gambling situations. Also, start gathering your documentation now if you haven't already. Most sportsbooks let you download your complete betting history, which makes creating that detailed record much easier. Don't wait until tax season when you're stressed and rushing to get everything together. The good news is that if you truly had net losses for the year, you shouldn't owe tax on gambling income - but you still need to report everything correctly to avoid any red flags with the IRS.
This is exactly the kind of guidance I was looking for! I'm in a very similar boat with around $92K showing on my PayPal 1099-K. Your point about starting the documentation process early really resonates - I've been putting it off but realize I need to get organized before meeting with a CPA. Quick question: when you called around to tax preparers, what specific questions did you ask to gauge their experience with gambling taxes and 1099-K issues? I want to make sure I find someone who really knows this area rather than someone who's just going to wing it. Also, did you end up using any of the tools others mentioned here (like the AI transaction categorization services) or did you go the manual spreadsheet route? I'm trying to decide if it's worth investing in software to help organize everything or if I should just buckle down and do it myself. Thanks for sharing your experience - it's reassuring to know I'm not the only one dealing with this mess!
I think you're overthinking this tbh. If the void box was checked on the original, you're fine. That's literally what the void box is for - to tell the IRS to ignore that form. The casino's system will only report the non-voided form to the IRS. I've had this happen 3 times (slot attendants make mistakes A LOT) and never had an issue with double reporting.
I work as a tax preparer and see W2-G issues frequently. Here's what I always tell my clients: definitely request that Wage and Income Transcript around March to verify what's actually on file with the IRS. Even though the casino checked the void box, I've seen cases where both forms still ended up being transmitted to the IRS due to system errors. Also keep both the voided form AND the reprint in your records. If there's ever a discrepancy, you'll need both documents to prove the situation. The IRS will want to see the voided form with the void box checked and the reprint with the same winning amount to understand why there might be duplicate entries in their system. Most importantly, when you file your return, only report the amount from the valid (reprinted) W2-G. Don't try to "offset" or account for potential double reporting on your return - that just creates more confusion. If the transcript shows a problem, deal with it then through proper channels.
This is really helpful advice! As someone new to dealing with gambling winnings, I didn't realize you could request transcripts to verify what the IRS actually has on file. Quick question - when you mention keeping both the voided form and the reprint, should I also keep any other documentation from the casino about the error? Like if they gave me a receipt or incident report when they were fixing the mistake?
Quick question - if I'm using TurboTax, where exactly do I find the Form 8995? I think I qualify too but can't seem to locate it in the software.
In TurboTax, you need to enter your business income first (Schedule C), and then it should automatically ask about the QBI deduction. If it doesn't, search for "QBI" or "qualified business income" in the search bar at the top. You can also check under the "Deductions & Credits" section and look for "Business Income Deductions.
This is really helpful! I'm in a similar boat with my new freelance writing business that I started in September. Made about $2,800 in profit and was wondering if I qualified for the QBI deduction. Based on what everyone's saying here, it sounds like I should qualify under that same income threshold exception since writing is also typically considered an SSTB. My husband and I file jointly and our total income is around $195,000, so we're well under that $375,800 threshold. One thing I'm curious about - do we need to have any specific business structure (LLC, etc.) or does it work for sole proprietorships too? I'm just operating as a sole proprietor right now and reporting everything on Schedule C.
You absolutely qualify for the QBI deduction as a sole proprietor! The business structure doesn't matter - sole proprietorships, LLCs, S-Corps, and partnerships can all qualify for QBI. Since you're reporting on Schedule C, you're all set. With your joint income of $195,000 being well below the $375,800 threshold, your freelance writing business gets the full benefit despite being an SSTB. You'd get a 20% deduction on that $2,800 profit, which works out to about $560 - definitely worth claiming! The QBI deduction is specifically designed to help small business owners like us, regardless of how we're structured. Just make sure your tax software picks it up when you enter your Schedule C income.
25 One thing nobody's mentioned yet: you might need to pay STATE taxes too, not just federal! For me in California, I set aside an extra 8% just for state taxes on top of the 25% for federal. Check your state tax rates and factor that in!
Great point about state taxes! Since you're in Ohio, you'll need to factor in Ohio state income tax too. Ohio has a progressive income tax rate that ranges from 0% to 3.99%. For your income level (around $24k annually), you're probably looking at around 1-2% for state taxes. So I'd recommend setting aside about 27-30% total: roughly 25% for federal (income + self-employment tax) and 2-3% for Ohio state taxes. Ohio also requires quarterly estimated payments just like federal, so you can usually pay both at the same time. Don't forget Ohio also has local income taxes in many cities - check if your city has additional income tax requirements. Some cities in Ohio charge an additional 1-3% on top of state taxes. You can check the Ohio Department of Taxation website to see what applies to your specific location.
Amina Bah
2 Wondering what everyone uses for gas receipts when you sometimes use your car for business and sometimes for personal use? Do you just track mileage instead of keeping all the gas receipts?
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Amina Bah
β’8 For me, tracking mileage has been MUCH easier than keeping gas receipts. I use MileIQ app that automatically logs my drives, then I just swipe left for personal trips and right for business. At tax time, I just use the standard mileage deduction rate which covers gas, maintenance, depreciation, etc.
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StellarSurfer
11 Great question about mixed receipts! I've been dealing with this exact issue for years as a small business owner. Here's what I've learned works best: The IRS requires you to substantiate business expenses, but they don't require separate receipts - just clear documentation. Here's my system: 1. **Photo everything immediately** - I snap a pic of every receipt right after purchase using my phone's camera 2. **Use a simple notation system** - I circle or highlight business items directly on the receipt, then write "Biz: $XX.XX" at the top 3. **Digital backup** - I store all receipt photos in a dedicated Google Drive folder organized by month 4. **Spreadsheet tracking** - I log each business expense with date, vendor, amount, and category. In the notes column, I include "Mixed receipt - total $XX.XX, business portion $XX.XX" The key is consistency. Whatever system you choose, use it every single time. I've been through two IRS audits using this method and never had any issues - they just want to see that you can prove your business expenses are legitimate and properly documented. Pro tip: Many stores will do separate transactions if you ask nicely at checkout. Saves tons of time later!
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Connor O'Neill
β’This is really helpful advice! As someone just getting started with business expense tracking, I'm curious about the audit process you mentioned. When they reviewed your mixed receipts during those audits, did they ask for any specific additional documentation beyond what you described? I want to make sure I'm setting up my system properly from the beginning to avoid any issues down the road.
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