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Hey Rudy, I went through something really similar last year with crypto gambling losses and unreported cash income. The stress was unreal, but it's totally fixable if you handle it right. First thing - yes, you absolutely need to report gambling activity even if you lost money. The IRS wants to see all your gambling transactions, wins AND losses. Keep detailed records of every bet, every payout, every loss. Screenshots, transaction IDs, everything. For your cash income situation, I'd recommend getting ahead of it before they find you. I ended up filing amended returns for the years I missed and used the IRS Voluntary Disclosure Program. Yeah, there were some penalties, but way less scary than waiting for them to audit me. About your "HandyHelp Solutions" name - definitely get that properly registered ASAP. File a DBA with your county and maybe get a basic business license. It shows good faith that you're trying to do things right going forward. The crypto gambling thing is tricky because different sites report differently to the IRS. Some offshore sites don't report at all, but that doesn't mean you're off the hook. I learned the hard way that "they can't track it" isn't actually true anymore. Get professional help if you can afford it. A tax pro who knows crypto saved me from making this way worse than it had to be.
Cameron, this is really helpful advice. I'm in a similar boat with offshore crypto gambling sites. When you say "they can track it" - how exactly does that work? I used sites like Stake and some smaller ones that supposedly don't report to the US. Did you end up having to report transactions from sites that don't send you any tax forms? Also, when you did the Voluntary Disclosure Program, did they ask for documentation going back multiple years? I'm worried I don't have good enough records from when I first started gambling with crypto.
@Zadie Patel Yeah, the tracking thing was eye-opening for me. Even though sites like Stake don t'send you 1099s, the IRS has gotten really good at blockchain analysis. They can trace crypto movements between wallets and exchanges, especially if you ever converted back to USD through a US exchange like Coinbase or Kraken - those definitely report to the IRS. For the Voluntary Disclosure Program, they did want documentation going back to when I started, but they were reasonable about incomplete records. I had to reconstruct what I could from blockchain explorers, email confirmations, and bank statements showing when I bought crypto. The key was being honest about what I had vs what I was estimating. The IRS actually appreciated that I was being proactive about coming clean rather than waiting to get caught. My tax attorney said showing good faith effort to comply, even with imperfect records, goes a long way in reducing penalties. Way better than the alternative of them finding out on their own.
Rudy, I totally understand the panic you're feeling right now - I was in almost the exact same situation a couple years ago. Here's what I wish someone had told me at the start: First, take a deep breath. This is fixable, but you need to act strategically. The crypto gambling losses are actually reportable income events - every bet is technically a taxable transaction, even on offshore sites. The good news is losses can offset wins, but you need detailed records. For your cash income situation, I'd strongly recommend getting compliant voluntarily before they find you. The IRS has programs specifically for people in your situation. I used a CPA who specialized in delinquent filings and it made all the difference. Yes, there were penalties, but much smaller than if I'd been caught. About "HandyHelp Solutions" - definitely legitimize that business name ASAP by filing a DBA. It shows you're making good faith efforts to comply going forward. One practical tip: start keeping meticulous records NOW for everything - every cash job, every crypto transaction, every business expense. Even if your past records are incomplete, having good documentation going forward helps show the IRS you're serious about compliance. The stress is real, but thousands of people have been through this exact situation and come out fine on the other side. Don't let fear paralyze you - taking action now is your best protection.
For TurboTax specifically, they'll ask if you have self-employment income. Say yes, and then you'll be guided to the "Business Income" section. Enter your Patreon/Buy Me A Coffee as a sole proprietorship business. You can use your own name as the business name if you don't have a formal business name.
This is helpful but I'm still confused about what business category to choose in TurboTax. Would an artist on Patreon be "Arts & Entertainment" or something else?
For artists on Patreon, you'd typically choose "Arts & Entertainment" or more specifically "Independent Artists, Writers, and Performers" if that option is available. The exact category isn't super critical for tax purposes - what matters most is that you're reporting it as self-employment income. TurboTax will guide you through the business code selection, and you can always search for "artist" or "creative services" in their business code lookup tool. The key is being consistent year over year with whatever category you choose.
One important thing to remember is keeping track of your expenses throughout the year, not just at tax time! I wish someone had told me this when I started my Patreon. Set up a simple spreadsheet or use an app to log art supplies, software subscriptions, equipment purchases, and even things like packaging for rewards you send to patrons. Also, don't forget about the home office deduction if you have a dedicated workspace for your art. Even if it's just a corner of a room that you use exclusively for creating content, you can potentially deduct a portion of your rent/mortgage, utilities, and other home expenses. TurboTax has a simplified method that lets you deduct $5 per square foot up to 300 square feet, which is much easier than calculating actual expenses. The key is being organized from day one rather than scrambling to reconstruct everything come tax season!
This is such solid advice! I'm just starting out and already feeling overwhelmed by the idea of tracking everything. Do you have any recommendations for simple apps or tools that make expense tracking easier? I'm worried I'll forget to log things or lose receipts. Also, for the home office deduction - does it have to be a completely separate room, or can it really be just a dedicated corner like you mentioned?
One thing no one has mentioned - if you're gambling on sites that aren't legal in the US, reporting those winnings doesn't make the gambling itself legal. You still have to pay taxes on illegal income (IRS doesn't care where money comes from, they just want their cut), but reporting it doesn't protect you from other legal issues related to using those platforms. Most people don't run into problems, but just something to be aware of since you mentioned the platform isn't regulated in the US.
Great question! I went through something similar last year with about $8K in crypto gambling profits. Here's what I learned after consulting with a tax professional: The key thing is that you need to report the fair market value in USD at the time you received each winning, not when you eventually cash out. So if you won 0.5 ETH when ETH was $2,000, that's $1,000 of taxable gambling income even if ETH later drops to $1,500. For your situation with $13.5K in profits, you'll report this as "Other Income" on Form 1040 Schedule 1. Since you haven't converted to USD yet, you're not dealing with capital gains/losses on the crypto holdings themselves - that only comes into play when you sell. One practical tip: start documenting everything now while it's still relatively fresh in your memory. Create a spreadsheet with dates, amounts won in crypto, and the USD value at that time. You can use sites like CoinGecko or CoinMarketCap to get historical pricing data. The IRS expects you to use "reasonable methods" to determine fair market value, so using widely-accepted pricing sources should be fine. Also remember that if you have gambling losses, you can potentially deduct them against your winnings if you itemize deductions, but only up to the amount of your winnings.
This is really helpful, thank you! I'm a bit overwhelmed by all the record-keeping requirements, but your point about documenting everything while it's fresh makes a lot of sense. Quick question - when you say "reasonable methods" for determining USD value, did your tax professional give any guidance on which pricing source is best? I see different prices on different exchanges sometimes, especially for the exact timestamps of my wins. Should I just pick one source and stick with it consistently, or is there a "gold standard" that the IRS prefers? Also, did you end up needing to itemize to claim your losses, or did the standard deduction work out better for your overall situation?
I'm going through this exact same situation right now! My daughter turned 17 in January and I just finished my taxes only to discover I owe $1,200 instead of getting my usual refund. Like you, she's still completely dependent on me, still in high school, and costs just as much (if not more) than when she was 16. What really gets me is that I can still claim her as a dependent for the $500 credit, but somehow she's not "child" enough for the full Child Tax Credit anymore. The math doesn't add up when you're already stretched thin as a single parent. I'm definitely going to look into some of the resources others have mentioned here, especially the payment plan options. Thank you for posting this - it helps to know I'm not the only one blindsided by this arbitrary cutoff. The system really does feel broken when working parents are scrambling to pay unexpected tax bills while the wealthy find every loophole to avoid paying anything.
I feel your pain! I'm new to this community but going through something similar. My son just turned 17 last month and I'm dreading doing my taxes now after reading all these stories. It's crazy that there's such a huge financial cliff at 17 when literally nothing else changes about their dependency status. What I don't understand is why Congress set it up this way. If the goal is to help families with children, why does it suddenly stop mattering that you're supporting a child just because they hit a certain birthday? My son is still eating me out of house and home, still needs school supplies, still can't work full-time because he's in school. The $1,500+ difference between the Child Tax Credit and the Credit for Other Dependents is brutal for families already struggling to make ends meet. Thanks for sharing your experience - it's helpful to know what to expect, even if it's frustrating news.
I'm so sorry you're dealing with this - the 17-year-old cutoff really is one of the most frustrating aspects of our tax system. As someone who works in tax preparation, I see this shock and anger from parents every single year, and it never gets easier to explain why Congress drew this arbitrary line. A few practical suggestions for your immediate situation: First, definitely look into the IRS payment plan options that others mentioned. You can set up an installment agreement online at IRS.gov, and for amounts under $50,000, it's usually pretty straightforward. The fees are much less painful than the penalties and interest that accumulate if you don't pay. Second, if your daughter has any part-time job income, make sure she files her own return - she'll likely get back everything that was withheld and that money stays in your household. Also, start tracking any education expenses now, because if she takes any college courses (dual enrollment, community college classes, etc.) while still in high school, you might qualify for education credits that can help offset some of this loss. The system definitely feels broken when you're working multiple jobs and still getting hit with surprise tax bills. Hang in there, and know that you're doing everything right - it's the tax code that's wrong here.
Thank you so much for the practical advice! I really appreciate hearing from someone who works in tax prep and sees this situation regularly. It's both frustrating and somewhat comforting to know that my shock and anger is a common reaction - at least I know I'm not crazy for thinking this system doesn't make sense. I'm definitely going to look into setting up that payment plan online. The idea of paying penalties and interest on top of the $1400 I already can't afford is terrifying. And you're right about tracking education expenses - my daughter has been talking about taking a college course this summer, so I'll make sure to keep all those receipts. It's just so maddening that we have to jump through all these hoops and hunt for credits to make up for an arbitrary age cutoff. But I guess that's the reality of our tax system. Thanks again for taking the time to offer real, actionable help instead of just sympathy.
Darcy Moore
I'm confused about something - if the government knows ur making illegal money isn't that just admitting to a crime?? like if i put $50,000 in "other income" and I don't have a job, isn't that basically telling them im doing something illegal?
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Dana Doyle
ā¢Not necessarily. You could have income from gambling winnings, gifts, selling personal items, side gigs that pay cash, etc. None of those are illegal. The IRS mainly cares that you're reporting income and paying taxes on it, not necessarily where it came from.
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Liam Fitzgerald
This is such an important topic that I think gets overlooked. I've been dealing with a similar situation where I had some cash income from freelance work that wasn't reported by the clients (they paid under the table). I was terrified about how to handle it properly. What I learned from talking to a tax professional is that the key is being proactive about reporting ALL income, even if the source might raise questions. Like others mentioned, you can use broad categories without getting into specifics that might be self-incriminating. The bigger risk is trying to hide income entirely - that's where people get into serious trouble with tax evasion charges. The IRS has gotten very good at detecting unreported income through data matching and lifestyle audits. It's much better to report everything and deal with any questions that come up than to try to fly under the radar. One thing I'd add is that if you're in this situation, it's really worth consulting with both a tax attorney and a CPA who understand these issues. The consultation fee is nothing compared to the potential consequences of handling it wrong.
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Amara Adebayo
ā¢This is really helpful advice, especially the point about being proactive. I'm in a somewhat similar situation - I do some cash work on the side and wasn't sure how to report it without creating problems. Your point about lifestyle audits is scary but makes sense - if someone's living beyond their reported means, that's going to raise red flags eventually. Better to report everything upfront and pay the taxes than deal with an investigation later. Did you end up having any issues after reporting your unreported income, or did it go smoothly once you got professional help?
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