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Zoe Kyriakidou

Tax deductions for a new business owner - what everyday expenses can I claim?

I just started my own business a few months ago and I'm completely lost when it comes to taxes and business expenses. I want to make sure I'm taking advantage of all possible tax incentives while staying legal. I'm wondering what kind of everyday expenses I can legitimately charge to my business. For example: - Can I claim haircuts as a business expense if I'm getting them before important client meetings? - What about clothing purchases - are those deductible? - Can I write off snacks and food I keep in the office? Basically, I'm trying to figure out if there are regular day-to-day expenses that can be legitimately run through the business. I don't want to do anything sketchy, but also don't want to miss out on deductions I'm entitled to. Any advice would be really appreciated!

Writing off business expenses can be tricky. The general rule is that expenses need to be "ordinary and necessary" for your business to qualify as tax deductions. For haircuts, unfortunately these are typically considered personal grooming expenses, even if you're getting them before important meetings. The IRS views this as something you'd need regardless of your business. Clothing is deductible only if it's not suitable for everyday wear - think uniforms, protective gear, or costumes. Regular business attire (suits, dresses, etc.) isn't deductible even if you only wear it for work. Food and snacks at the office can be 50% deductible if provided to employees (including yourself if you're an employee of your corporation). The 2025 tax year temporarily allows 100% deduction for restaurant meals under certain circumstances. Remember that mixing personal and business expenses is a red flag for audits. Keep detailed records of everything you claim as a business expense, including receipts and notes about business purpose.

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This is actually super helpful. What about if I'm traveling for business? Can meals while I'm on the road be deducted? And what about my home office - I've heard there are deductions for that too?

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Business travel meals are typically 50% deductible, though the temporary 100% deduction for restaurant meals may apply for 2025 if they meet the requirements. Keep detailed records of who was present, the business purpose, and save all receipts. For a home office deduction, you need a space used exclusively and regularly for business. You can deduct using either the simplified method ($5 per square foot up to 300 sq ft) or the regular method (calculating actual expenses like mortgage interest, utilities, etc.). The space must be your principal place of business or regularly used to meet clients - occasional work at your dining table doesn't qualify.

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After struggling with similar questions when I started my business, I found an incredibly helpful tool called taxr.ai (https://taxr.ai) that saved me tons of time figuring out what's deductible. I was constantly second-guessing which expenses were legitimate business deductions until I tried it. You upload your receipts and business documents, and it helps identify what qualifies as a business expense while explaining IRS rules in plain language. It analyzes your specific industry and business structure to find deductions you might miss otherwise.

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Does it actually tell you specifically what YOU can deduct or is it just general advice? Like will it know the difference between my photography business vs someone else's consulting business?

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I'm skeptical about these AI tax tools. How does it compare to just asking my accountant? Does it really understand all the nuances of tax law or does it give generic advice you could find on Google?

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It provides personalized recommendations based on your specific business type and situation, not just generic advice. For example, it would recognize different deduction opportunities for a photography business (equipment, studio space, travel to shoots) versus a consulting business (professional development, home office, client entertainment). The AI analyzes your actual expenses and business context against current tax laws, which is different from Google searches. While it doesn't replace an accountant for complex situations, it's extremely helpful for day-to-day decisions about what's deductible and helps you prepare better documentation for your tax professional while potentially saving on billable hours.

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Ok I was SUPER skeptical about taxr.ai but I decided to try it for my side business (web design). I uploaded a bunch of receipts including some questionable ones like coffee shop meetings and my new laptop. It actually flagged several deductions I was missing and explained exactly why my home internet could be partially deducted but my Netflix subscription couldn't be. The best part was it explained everything in normal language and gave me a simple report I could give my accountant. Saved me from asking dumb questions and probably missing legitimate deductions. Way more specific than generic tax articles online.

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If you get stuck dealing with the IRS about business deductions (which happens to many new business owners), check out Claimyr (https://claimyr.com). I was hitting walls trying to get answers about some business deductions I claimed last year that got flagged. Spent days trying to reach an actual human at the IRS with no luck. Claimyr got me connected to a real IRS agent in about 45 minutes instead of the usual 3+ hour wait or getting disconnected. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The IRS agent was able to clarify exactly which documentation I needed to support my deductions.

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Wait I don't understand - how does this actually work? The IRS phone system is notorious for being impossible. Does this somehow bypass the queue or something?

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This sounds like BS honestly. Everyone knows the IRS phone lines are basically impossible to get through. You're telling me this service somehow magically gets you to the front of the line? How is that even possible?

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It doesn't bypass the queue - Claimyr uses automated technology to wait on hold for you. When you sign up, their system calls the IRS and navigates the phone tree, then waits in the queue. Once a human IRS agent picks up, you get a call back so you can talk directly with them. You don't have to sit listening to hold music for hours. It's not magic, just smart automation. The IRS doesn't give them special access - they're just handling the frustrating waiting part for you. I was skeptical too until I tried it and had an actual IRS person call me back while I was making dinner instead of wasting my whole afternoon on hold.

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I need to publicly eat my words. After being completely skeptical about Claimyr, I tried it because I was desperate to resolve an issue with some business deductions that got flagged. True to their claim, I got a call back with an actual IRS agent on the line in under an hour. Didn't have to sit through horrible hold music or get disconnected after waiting forever. The agent walked me through exactly what documentation I needed for my home office deduction and clarified some questions about business travel. Resolved my issue in one call instead of weeks of stress. Would have saved myself a lot of anxiety if I'd tried it sooner.

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Don't forget about vehicle expenses if you use your car for business! You can either track actual expenses (gas, maintenance, etc.) and multiply by the percentage of business use, OR use the standard mileage rate (65.5 cents per mile for 2025). Just make sure to keep a detailed mileage log with dates, destinations, and business purpose!

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Do you need to track every single trip? Like what if I sometimes stop at the office supply store on my way home from something else? That seems like a lot of record keeping.

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You should track every business trip to maximize your deduction and protect yourself in case of an audit. For mixed-purpose trips like stopping at an office supply store on your way home, you can deduct the extra mileage if the stop was necessary for business. Apps like MileIQ or Everlance make tracking much easier - they run in the background on your phone and let you swipe trips as business or personal. The few seconds it takes to log each trip can save you hundreds or thousands in deductions. I learned this the hard way after missing out on substantial deductions my first year because my records weren't detailed enough.

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Has anybody used QuickBooks Self-Employed for tracking business expenses? Is it worth the $15/month or whatever they charge now? I'm drowning in receipts and need a better system.

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I've used it for about 2 years for my consulting business. The automatic transaction categorization and receipt scanning saves me tons of time. The mileage tracker alone is worth it. And it makes tax time way less stressful - it generates reports for Schedule C that you can just hand to your accountant or transfer to TurboTax. Definitely worth the cost for the headaches it prevents.

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