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Ask the community...

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One thing nobody's mentioned yet - for your business expenses, check your email! I thought I had lost all my receipts too until I searched my email for "receipt" "confirmation" "order" etc. Found like 80% of what I needed. Also check your accounts on websites where you bought stuff (Adobe, Amazon, etc) - they often keep purchase histories. And don't forget to check your cloud storage if you use Google Drive or Dropbox, you might have saved stuff there without remembering.

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This is great advice but what about cash transactions? I paid some of my business expenses in cash and have literally zero proof. Is there any way to claim those or am I just out of luck?

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For cash transactions, you're in a tougher spot, but not hopeless. Try to find any indirect evidence - ATM withdrawal records from your bank statements that align with when you think you made purchases, any notes or calendar entries about what you were buying or why. The key is reasonableness - if you can show a pattern (like you regularly withdrew $200 in cash every month for business supplies), that's better than nothing. Just be honest and consistent with your reconstruction, and only claim what you're confident you actually spent. And in the future, either keep receipts for cash purchases (even taking a quick photo with your phone works) or use a credit/debit card for better tracking.

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Ali Anderson

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FWIW I was audited last year for my small business and had pretty terrible records. The auditor was actually more reasonable than I expected. They allowed most of my expenses even with minimal documentation as long as they seemed reasonable for my type of business. They mainly focused on making sure I wasn't claiming personal expenses as business ones. So focus on being honest about what were legitimate business expenses vs personal. And definitely don't ignore the issue - reporting your income with reasonable expenses (even if documentation is weak) is WAY better than not reporting income at all!

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Zadie Patel

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This is reassuring to hear! Was there anything specific that triggered your audit? I'm trying to figure out what to avoid so I don't get flagged...

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Yara Abboud

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Something nobody's mentioned yet - you should really look into the QBI (Qualified Business Income) deduction when making this decision. It lets you deduct up to 20% of your business income in certain situations, but salary payments to yourself DON'T count toward this deduction. This is why a lot of small business owners do a smaller salary and larger distributions - to maximize the QBI deduction. But there are phase-outs based on income levels and business type.

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PixelPioneer

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Can you explain more about these phase-outs? I've heard about QBI but my accountant said I probably can't use it because of my income level (around $225k).

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Yara Abboud

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The phase-outs start at $170,050 for single filers and $340,100 for joint filers (for 2022 tax year, slightly higher for 2023). Above those thresholds, the deduction starts to phase out for specified service businesses (legal, health, consulting, financial services, etc.). For non-service businesses, instead of phasing out completely, the deduction becomes limited based on W-2 wages paid and qualified property. This is where it gets tricky - sometimes paying yourself MORE in W-2 wages actually increases your QBI deduction if you're over the threshold. That's why personalized analysis is so important.

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Has anyone here dealt with health insurance as a sole director/owner? I'm setting up a company and wondering if I should put myself on payroll JUST to get the health insurance deduction, since I think it has to run through the payroll system to be fully deductible?

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Paolo Rizzo

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If you have an S-Corp, health insurance premiums paid for a >2% shareholder (which you would be) must be reported as income on your W-2, but then you get to deduct them on your personal return. It's a wash tax-wise, but requires the proper paperwork. For an LLC taxed as a sole proprietorship, you can take the self-employed health insurance deduction directly on your personal return without running it through payroll.

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There are legitimate ways to legally not have to file taxes if your income is below certain thresholds. For 2025, if you're single and under 65, you don't need to file if your income is below $14,350. Different thresholds apply for other filing statuses.

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Mia Alvarez

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This is true but dangerous advice without context. Even if you're under the threshold, you might still want to file if you had any taxes withheld from paychecks because that's the only way to get a refund of that money. Also, certain credits like the Earned Income Credit require filing to receive them.

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I work for a state tax agency (not the IRS) and I can tell you that "under the radar" is basically a myth these days. Between W-2s, 1099s, mortgage info, and banking data, the government has a pretty comprehensive picture of your financial situation whether you file or not. Not filing just means giving up control of your tax situation and potentially leaving money on the table.

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One option that hasn't been mentioned yet is using tax software that can handle nominee distributions. I used TaxAct last year when I had to report interest from bonds that belonged to my niece (I was the custodian), and it walked me through the whole process including generating the necessary 1099-INT forms. The software included the ability to e-file the information returns, which eliminated the need for the special red paper forms altogether. Much easier than trying to deal with the paper forms and getting everything right!

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Does TaxAct specifically handle the nominee distribution situation for inherited savings bonds? I've been using TurboTax but couldn't find this feature. Does it also file the 1096 form that needs to accompany the 1099-INTs?

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Yes, TaxAct has a specific module for handling nominee distributions, including from savings bonds. When you indicate you received interest that partially belongs to someone else, it walks you through reporting your portion on your return and then helps you prepare the 1099-INTs for the other recipients. It also handles the 1096 form automatically as part of the e-filing process. If you choose to e-file these information returns, you don't need to worry about the red forms at all since everything is submitted electronically. TurboTax might have this feature too, but it's sometimes in their higher-tier packages.

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Just want to add - if you're filing fewer than 10 information returns (like 1099-INT), you can actually file them for FREE electronically through the IRS FIRE system. No need for special red forms or paying for e-filing services. Here's the link: https://fire.irs.gov/ You'll need to register for an account, but it's relatively straightforward. This solved the exact problem you're having with the red forms, and it's direct through the IRS.

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Kai Santiago

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I tried using the FIRE system last year and found it incredibly confusing. It's not designed for casual users or one-time filers. You need to follow very specific file format requirements and testing procedures. I ended up just paying a tax professional to handle it for me.

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Have you considered starting a small business from home? When I was staying home with my kids, I started a part-time craft business that gave me some income AND let me take some home office deductions. You can deduct a portion of utilities, internet, etc if you use part of your home exclusively for business. Just make sure you're actually trying to make a profit and keep good records!

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Be really careful with home office deductions though - it's supposedly one of the biggest audit triggers if not done right. Don't you need to have a room that's ONLY used for business? Like not a shared space at all?

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You're absolutely right about being careful. The space needs to be used "regularly and exclusively" for business, but it doesn't have to be an entire room. It can be a clearly defined part of a room, like a desk area in your living room that's only used for business activities. The key is making sure you're running a legitimate business with the intention of making a profit, not just a hobby. Keep detailed records of all business activities, expenses, and income. Take photos of your workspace too. I've been doing this for 3 years now and while I haven't been audited, I make sure I could defend every deduction if needed.

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Just want to add something that helped us - my husband is a SAHD and we made him an authorized user on my business credit card. He uses it for household purchases that support my work (like when he picks up office supplies or runs work-related errands). This doesn't create any tax breaks directly but it helps him build credit history while technically contributing to the family business. Might be worth considering if credit building is also on your mind.

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Doesn't being an authorized user on any card build credit though? Like couldn't you just add him to your regular personal credit card? I don't see how this is a tax thing at all.

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