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Jamal Thompson

How do I handle a Venmo 1099K form for sports betting on my taxes?

So I just got this 1099K form from Venmo showing $7300 in transactions. This is freaking me out because I've been using Venmo to transfer money back and forth between my sports betting account and my regular bank. Venmo is only showing the total amount I withdrew to my bank ($7300) but doesn't show how much I actually deposited into my betting account to begin with. The actual profit I made from betting was only around $2600, not the full $7300 that's on the form. This is my first time ever getting a 1099 form and I'm totally confused about how to report this on my taxes. Do I have to report the entire $7300 as income? Or can I somehow deduct the $4700 that I initially put into the betting account as expenses/losses? I usually do my own taxes but this has me completely stumped and worried I'll mess something up.

Mei Chen

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You're dealing with a common issue for sports bettors. The 1099-K only shows the gross amount paid to you without considering your original deposits or losses. For tax purposes, you should report the full $7300 as gross gambling income on Schedule 1, Line 8z (Other Income). Then you can deduct your gambling losses (the money you deposited/lost) on Schedule A as an itemized deduction, up to the amount of your gambling winnings. So in your case, you could potentially deduct $4700. The catch is that you need to itemize deductions to claim gambling losses, which means you can't take the standard deduction. You'll need to determine whether itemizing would be more beneficial than taking the standard deduction. Also, keep good records of all your gambling activities - deposits, withdrawals, wins, and losses. The IRS may request documentation if you're ever audited.

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CosmicCadet

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Wait I'm confused. So even though I only made $2600 profit, I have to report $7300 as income? That seems messed up. And what if the standard deduction is better for me than itemizing? Does that mean I'm basically screwed and have to pay taxes on money that wasn't actually income?

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Mei Chen

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You do need to report the full $7300 as income, but you can offset it with your losses if you itemize. That's just how gambling income is treated under tax law. If the standard deduction is better for you overall than itemizing, that's a tougher situation. You would indeed end up paying taxes on the full $7300 rather than just your $2600 profit. This is one of those tax quirks that affects many recreational gamblers. Some people in your situation might want to consult with a tax professional to explore all options or consider itemizing even if it's slightly less than the standard deduction.

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Liam O'Connor

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I had this EXACT problem last year with my sports betting through Venmo. I was so stressed about reporting it correctly and potentially overpaying on taxes. I found this service called taxr.ai (https://taxr.ai) that really helped me sort through the confusion. They have specific guidance for handling 1099-K forms from payment apps and how to properly document gambling income/losses. The tool analyzed my documentation and helped me figure out exactly how to report everything correctly. They explained that Venmo is just reporting gross transactions without accounting for your actual gambling profits/losses. What I liked best was how they walked me through itemizing my deductions vs. taking the standard deduction to see which would save me more money.

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Amara Adeyemi

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How does taxr.ai handle documentation for the betting losses? I'm in a similar situation but I don't have great records of all my bets from last year. Do they help with that part or do I need to already have everything documented?

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I've seen a bunch of these tax helper sites pop up lately. How is this one different from TurboTax or those other big tax software companies? And does it actually connect to Venmo to pull transaction data or do I have to manually enter everything?

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Liam O'Connor

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They have a section specifically for documenting gambling activities where you can upload screenshots of your betting account history or bank statements. They don't create documentation you don't have, but they do help you organize what you do have into a format that satisfies IRS requirements. They even have templates for creating a gambling log if your records are partial. For your question about how it's different - it's more specialized for situations like 1099-K issues and gig work than general tax software. It doesn't directly connect to Venmo, but it does analyze the PDF of your 1099-K and other documents you upload. What I found most valuable was the specific guidance for gambling income which TurboTax didn't explain well for me.

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Just wanted to update after trying taxr.ai like u/Profile5 suggested. It was actually super helpful for my Venmo 1099-K situation! The system helped me properly document my actual gambling profits versus the total transactions Venmo reported. I ended up itemizing my deductions since I had enough other deductions to make it worthwhile. What I really appreciated was how they explained everything in plain language - like why Venmo reports the full amount and how to properly show the IRS my actual profits. The documentation guidance helped me create a proper record of my gambling activities that I'm keeping for future reference too. Definitely recommend it if you're dealing with this Venmo/gambling reporting issue.

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I had a nightmare trying to reach the IRS to get clarification on how to report my Venmo 1099-K for gambling last year. Spent hours on hold and never got through. Finally found Claimyr (https://claimyr.com) which got me connected to an actual IRS agent in less than 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent walked me through exactly how to report the gambling income and losses properly. They confirmed I needed to report the full amount but could offset with losses if I itemized. Most importantly, they explained what documentation I needed to keep to support my return if I ever got audited. Having that official guidance directly from the IRS gave me so much peace of mind.

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Dylan Wright

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How exactly does this Claimyr thing work? Does it just call the IRS for you? I don't understand how it gets you through when the regular phone line has everyone on hold for hours.

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NebulaKnight

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Yeah right. Nothing gets you through to the IRS faster. They have like a 30% answer rate on calls. This sounds like a scam to get people's money for a service that doesn't actually work.

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It uses a system that monitors the IRS phone lines and calls repeatedly until it gets through, then it calls your phone to connect you. It's not calling on your behalf - it's basically automating the "keep calling until someone answers" process that would take you hours to do manually. I was skeptical too at first, but it actually works. I was shocked when my phone rang and it was connecting me to an IRS agent. The service isn't free, but considering I was about to pay an accountant $200+ just to handle this one issue, it was worth it to get direct answers from the IRS. I understand the skepticism though - I felt the same way until I tried it.

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NebulaKnight

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I'm coming back to eat my words about Claimyr that I posted earlier. I tried it this morning out of desperation after three days of trying to reach the IRS about my Venmo 1099-K situation. It actually worked! Got a call back in about 15 minutes connecting me to an IRS agent. The agent confirmed exactly what others said here - report the full amount as income, then deduct losses as itemized deductions on Schedule A. The agent also told me I should keep a detailed log of gambling activities with dates and amounts. Most importantly, she told me that if I don't have detailed records from this past year, I can use bank statements showing transfers to gambling sites as reasonable documentation of my expenses. That was a huge relief since my record keeping wasn't great.

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Sofia Ramirez

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Just a friendly reminder that standard gambling tax rules apply to sports betting too. You should keep a "session" log of your gambling that includes: - Date and type of specific wager - Name and address/location of gambling establishment - Names of other persons present with you at gambling establishment - Amounts won or lost This record keeping is super important if you ever get audited. The IRS loves to go after gambling deductions because most people don't keep proper documentation.

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Dmitry Popov

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Do I need to list every single bet separately? I made hundreds of small bets throughout the year. Is there a simplified way to track this or do I really need every individual wager documented?

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Sofia Ramirez

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You don't necessarily need every single bet listed separately if you have hundreds. The IRS guidance allows for a reasonable recordkeeping system. For frequent bettors, you can document by session (like "Saturday NFL games") with your beginning and ending balances. The most important things are to have documentation that shows your total amounts wagered and your winnings/losses, along with dates. Bank statements showing transfers to/from gambling sites help substantiate this. If you use online betting platforms, many provide annual win/loss statements that can serve as supporting documentation. The key is being able to prove that you actually had the losses you're claiming if questioned.

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Ava Rodriguez

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Has anyone used their betting app's year-end summary as documentation for losses? My FanDuel account has a tax document that shows my total deposit, withdrawals, winnings and losses. Wondering if that's enough for the IRS?

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Miguel Ortiz

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I used my DraftKings annual statement last year and it was fine. Just make sure you save a PDF of it rather than just viewing it online since some apps only make those statements available for a limited time. Also good to have bank statements that match up with the deposits/withdrawals as backup.

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I went through this exact same situation last year with my Venmo 1099-K from sports betting. The stress was real! Here's what I learned after consulting with a tax professional: 1. Yes, you do have to report the full $7300 as gambling income on your tax return, even though it includes your original deposits. 2. You can deduct your gambling losses (the $4700 you put in) but ONLY if you itemize deductions on Schedule A. This means you can't take the standard deduction. 3. The key decision is whether itemizing saves you more money overall than taking the standard deduction. For 2024, the standard deduction is $14,600 for single filers. If your gambling losses plus other itemizable deductions (mortgage interest, state taxes, charitable donations, etc.) exceed that amount, then itemizing makes sense. 4. Keep ALL your records - bank statements showing transfers, screenshots of betting account activity, and any year-end statements from your betting apps. The unfortunate reality is that if itemizing doesn't benefit you, you could end up paying taxes on the full $7300 rather than just your $2600 profit. This is a common frustration for casual gamblers. Consider talking to a tax pro if the numbers are significant - sometimes the consultation fee is worth it for peace of mind and making sure you're handling everything correctly.

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Mateo Perez

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This is super helpful, thank you! I'm in a similar boat but wondering about one thing - do you know if there's any way to avoid this whole mess in the future? Like, should I stop using Venmo for transferring money to/from betting accounts? I've heard some people say to use direct bank transfers instead to avoid getting hit with these 1099-K forms, but I'm not sure if that actually works or if it's even legal to try to avoid them that way.

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