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Has anyone had issues with Cashapp not providing complete cost basis information? My 1099-B from them last year had a bunch of transactions marked as "cost basis not reported to the IRS" which made my taxes super complicated.
YES! This happened to me too. For crypto especially, they often don't track the cost basis if you transferred it in from another wallet. You have to keep your own records of what you originally paid. I use a spreadsheet now to track everything.
If this happens, don't panic. You'll need to fill out Form 8949 and check box "B" for transactions where the cost basis wasn't reported to the IRS. Then you'll need to enter the correct cost basis yourself using your own records. If you don't have perfect records, there are crypto tax services that can help reconstruct your transaction history by scanning the blockchain. Just whatever you do, don't leave the cost basis blank or the IRS will assume it's $0 and tax you on the entire amount!
StarStrider
This is really helpful info everyone! I'm definitely going to wait for those 1099-B forms from Cashapp before filing. One follow-up question - if I only made like $200 in gains total from both stocks and crypto, do I still need to report all of this? I know there are minimums for some tax forms, but I want to make sure I'm not missing anything since this is all new to me. Better safe than sorry with the IRS!
Yes, you absolutely need to report all capital gains and losses regardless of the amount! There's no minimum threshold for reporting investment income. Even if you only made $200, the IRS wants to know about it. The good news is that if your total gains are small, the tax impact will be minimal too - especially if you held the investments for less than a year, they'll just be taxed as ordinary income. But definitely don't skip reporting it just because the amount seems small. The IRS gets copies of those 1099-B forms from Cashapp, so they'll know about the transactions even if you don't report them.
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Ella Lewis
6 Question for anyone who's done this - do you need a special type of solo 401k plan to make employer contributions? My financial advisor set up my solo 401k last year but never mentioned anything about employer matching. Do I need to change my plan?
Ella Lewis
ā¢22 Most solo 401k plans allow for employer contributions, but not all. Check your plan documents or call your provider. I had to specifically ask about this when setting up mine through Fidelity. Some of the basic plans only allow employee contributions but can be upgraded.
NebulaNinja
14 As a newcomer here but someone who went through this exact decision process last year, I can confirm that maxing out both employee and employer contributions to your solo 401k is absolutely the way to go for tax efficiency. What helped me understand this was breaking down the numbers: if I took $25,000 as an S-corp distribution to invest in a taxable account, I'd pay income tax on that $25,000 first (let's say 22% = $5,500), leaving me with $19,500 to invest. Then I'd pay taxes annually on dividends and capital gains. But if I make that same $25,000 as an employer contribution to my solo 401k, it reduces my S-corp's taxable income dollar-for-dollar, meaning I save that entire $5,500 in taxes upfront. Plus the money grows tax-deferred. The only real consideration is liquidity - make sure you have adequate emergency funds in accessible accounts first. But for retirement savings specifically, the 401k route beats taxable investing by a wide margin when you run the math.
Ezra Collins
ā¢6 This breakdown is really helpful, thanks! I'm just starting to research this topic and the tax math makes sense when you put it that way. Quick question - when you say "employer contribution," are you literally paying yourself as the employer? How does that work practically? Do you just write a check from the business account to the 401k provider, or is there a specific process you have to follow?
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Freya Larsen
Has anyone here used TurboTax to file their amended return? Is it worth paying for or should I just do the paper forms myself? I'm in a similar situation with a late W-2.
Omar Hassan
ā¢I used TurboTax for my amendment last year and found it worth the money. The software transfers all your info from the original return and helps identify all the forms that need to be updated. Way easier than trying to figure out the paper forms yourself, especially if your situation is even slightly complicated.
I went through this exact same situation two years ago and totally understand the stress! One thing that really helped me was keeping good records of when I received that late W-2 and any correspondence with my employer about the delay. The IRS is generally understanding about these situations since they know employers sometimes miss deadlines. When you file your amended return, make sure to include a brief explanation of why you're amending (late W-2 received). This helps the IRS processors understand the situation immediately. Also, if your amended return results in additional taxes owed, try to pay them as soon as possible to minimize any interest charges. The good news is that if your late W-2 shows more taxes were withheld than you originally reported, you might actually get a bigger refund! Don't let the stress get to you - amended returns are more common than you think, and the IRS processes thousands of them every day.
This is really reassuring advice, thank you! I was definitely panicking about whether the IRS would think I was trying to hide income or something. Good point about keeping records - I actually saved all the emails I sent to HR asking about my W-2, so I have documentation of the delay. You're right about potentially getting a bigger refund too - I'm hoping that's the case since my second job withheld quite a bit. Did you end up owing more or getting additional refund when you amended? Just trying to mentally prepare myself for either scenario!
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waited 3 weeks and nothing showed up... had to call irs turns out my address was wrong by one number smh
Diego Chavez
ā¢bruh moment fr fr š
Jamal Wilson
Also in TN here! Got mine last year and it took exactly 5 days from mail date. The IRS actually uses priority mail for refund checks so they're pretty reliable. Just keep checking your informed delivery - you'll see it coming the morning it arrives. Good luck! š¤
That's so reassuring! I had no idea they use priority mail - that makes me feel way better about the timing. Definitely signing up for informed delivery right now so I can stop obsessively checking my mailbox š Thanks for the info!
Oliver Wagner
Curious if anyone here has used a tax pro who specializes in traders? I'm getting different answers from different accountants about this exact issue and wondering if its worth paying extra for someone who deals with traders specifically.
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Natasha Kuznetsova
ā¢I use a specialist for my taxes (I do about 300-400 trades yearly). Cost me $750 instead of the $250 I used to pay H&R Block, but he saved me over $3k in taxes by properly classifying everything. For trader stuff, a specialist can be worth it if your situation is complex.
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Zainab Ibrahim
I went through this exact same situation two years ago when I transitioned from a corporate job to full-time trading. After consulting with both a tax attorney and CPA who specializes in securities, here's what I learned: "Investor" is definitely the correct occupation to use. The key distinction is that without trader tax status, your activities are considered investment activities rather than business activities, regardless of how much time you spend or how much income you generate. One important thing to keep in mind - if you're planning to continue this as your primary income source, make sure you're making quarterly estimated tax payments. Since you don't have an employer withholding taxes, you'll likely owe penalties if you don't pay estimated taxes throughout the year. Also, keep detailed records of all your trades and any investment-related expenses (trading platform fees, market data subscriptions, etc.) as these can potentially be deducted, though the rules changed with recent tax law updates. The occupation field really is just for statistical purposes - what matters is accurately reporting your capital gains and losses on Schedule D and Form 8949.
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Emma Taylor
ā¢This is really helpful advice! I'm curious about the investment-related expenses you mentioned - are these still deductible as miscellaneous itemized deductions, or did the Tax Cuts and Jobs Act eliminate most of these? I have subscriptions to trading platforms and data feeds that cost me about $2,000 annually, but I wasn't sure if I could still deduct them as an investor rather than a trader.
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