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As someone who's been through this exact situation, I'd strongly recommend getting some concrete numbers before making that truck purchase. With your $67k in 1099 income and that $16k annual tax hit, you're definitely in a position where smart vehicle deductions could make a real difference. Here's what I'd suggest: before you buy, calculate both scenarios with actual numbers. For the depreciation route on a $55k truck (assuming 80% business use), you're looking at potentially deducting around $44k in year one with Section 179. At your tax bracket, that could save you roughly $10-12k in taxes the first year alone. But here's the catch - you mentioned you're conservative with deductions and that's smart. Make sure you can genuinely justify that 80% business use percentage, because the IRS will want to see detailed records. If your actual business use is more like 60%, then your deduction drops accordingly. Also consider the cash flow impact. That truck payment might be $800-1000/month, but if you're saving $10k+ in taxes year one, it changes the math significantly. Just remember those big first-year savings mean smaller deductions in future years. Have you considered leasing instead? Sometimes the deduction structure works out better for contractors, especially if you like updating equipment regularly.

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Yara Khoury

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This is really helpful perspective! I hadn't considered leasing at all - how does the deduction structure work differently for leases vs purchases? Is it just that you deduct the lease payments instead of depreciation? Also, your point about cash flow is exactly what I've been trying to wrap my head around. If I could actually save $10-12k in taxes that first year, it would basically cover most of the annual truck payments. But I'm nervous about being too aggressive with that business use percentage. My work does require me to haul equipment to job sites, but I'd probably also use it for personal stuff on weekends. Would 70% business use be more realistic/defensible than 80%? I just don't want to get in trouble with the IRS over this.

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The 70% business use sounds much more realistic and defensible than 80%, especially if you're planning weekend personal use. The IRS loves to audit vehicle deductions, so being conservative here is smart. For leasing vs buying: With a lease, you deduct the business percentage of your monthly lease payments instead of taking depreciation. So if you lease for $600/month and use it 70% for business, you'd deduct $420/month ($5,040/year). The advantage is consistent annual deductions and no depreciation recapture issues if you switch vehicles. The downside is you don't own anything at the end, and there can be mileage restrictions that might not work for your equipment hauling needs. For your situation with lumpy 1099 income, the big first-year depreciation write-off might be more valuable since it hits that $16k tax bill hard right away. Just make sure you're prepared for smaller deductions in years 2-5. One more thing - since you're hauling heavy equipment, make sure whatever truck you get has the payload capacity you actually need. Don't let the tax tail wag the business dog. A truck that can't properly handle your work loads isn't worth any tax savings.

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This is exactly the kind of practical advice I was looking for! The point about not letting the tax tail wag the business dog really hits home - I need to make sure I'm buying the right truck for my actual work needs first, then optimize the tax benefits around that. I think you're right about the 70% business use being more defensible. I can definitely document my equipment deliveries and job site visits, but being honest about weekend personal use is probably the safer approach long-term. The lease vs buy comparison is helpful too. Given that big tax hit I'm dealing with each year, that first-year depreciation write-off does sound more appealing than spreading smaller deductions over time with a lease. Plus I like the idea of actually owning the truck at the end. One follow-up question - when you mention payload capacity, are there any tax implications if I go with a truck that's rated higher than what I actually need? Like if I get a 3500 series when a 2500 would handle my loads, does that affect the business justification for the IRS?

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Double Reporting Issue: 1099-K from Stripe vs 1099-NEC Requirements for Small Business Payments

I'm facing a confusing tax reporting situation that I need help with. One of my contractors just contacted me pretty upset because they're getting hit with what looks like double reporting - they received a 1099-K from Stripe for payments I made to them in 2024, but I also issued them a 1099-NEC for the same amounts. Here's what's happening: We pay our contractors through their payment system (Stripe) which initiates a bank EFT from our account. I've always understood that as a small business owner, I need to report all payments over $600 to non-corporate vendors via 1099-NEC unless they were paid by credit card. But now I'm worried this is making it look like my contractor received twice the money they actually did. With all these new reporting requirements where payment platforms like Venmo, PayPal, and Stripe have to issue 1099-Ks, does this mean I shouldn't be sending 1099-NECs to contractors who use these platforms? What's the correct approach here? What about contractors who use QuickBooks and I pay through their QB payment link that connects to my bank account - does QuickBooks also provide a 1099-K in those cases? I feel like the guidance on this wasn't clear for the 2024 tax year, and now I'm unsure if I made a mistake by issuing the 1099-NEC. Would really appreciate any insights, especially if you can point me to official documentation on how to handle this situation correctly.

Ryder Ross

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This thread has been incredibly helpful! I'm in a similar situation as Pedro but from the contractor side - I received both a 1099-K from Stripe and a 1099-NEC from my client for the same payments in 2024. What I found particularly useful from this discussion is understanding that this isn't necessarily a mistake, but rather an overlap in reporting requirements. Jake's explanation about ACH through Stripe creating this "middle ground" really clarified things for me. For other contractors dealing with this, I'd recommend keeping a spreadsheet that matches your invoices to both the 1099-K transactions and 1099-NEC amounts. This way you have clear documentation showing they represent the same income streams. I also plan to reach out to my clients proactively (like Dylan suggested) to discuss payment methods for 2025 to avoid this confusion next year. One question I still have: if I'm working with multiple clients who all pay through different platforms (some via Stripe, others through Square, etc.), should I expect to potentially receive multiple 1099-Ks plus individual 1099-NECs? The record-keeping is going to get complex pretty quickly.

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Yes, you should expect to potentially receive multiple 1099-Ks if you're working with clients who use different payment platforms. Each platform (Stripe, Square, PayPal, etc.) will issue their own 1099-K if you exceed their reporting thresholds with that specific platform. Plus you'll get individual 1099-NECs from each client for the same payments if they're paying via ACH through those platforms. I'd suggest creating a master spreadsheet with columns for: Client Name, Invoice Date, Amount, Payment Method, 1099-NEC Amount, 1099-K Platform, and 1099-K Amount. This way you can track everything in one place and easily identify overlaps. It sounds overwhelming, but once you set up the system it becomes much more manageable. Also consider asking your regular clients about consolidating payment methods for 2025 - maybe having them all use the same platform or switch to direct bank transfers to simplify your record-keeping. Many clients are happy to accommodate when you explain it helps with tax compliance.

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Mia Alvarez

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As someone who recently went through this exact situation, I can confirm that what everyone is saying here is correct - you absolutely did the right thing by issuing the 1099-NEC even though Stripe issued a 1099-K. This is one of those unfortunate gaps in the current tax reporting system. What I learned from my CPA is that the IRS recognizes this overlap exists and has built-in systems to detect when the same income might be reported on multiple forms. The key is proper documentation - both you and your contractor should keep records showing that these represent the same payments, not additional income. For 2025, I'd suggest having a conversation with your contractors about payment preferences. Some of mine actually preferred switching to direct ACH transfers from my business account to avoid the 1099-K complexity altogether. Others were fine with the dual reporting as long as I gave them a heads up about what to expect. One tip that helped me: I now include a brief note on my 1099-NEC transmittals explaining that the contractor may also receive a 1099-K from the payment processor for the same amounts. It saves confusion and shows you're being proactive about compliance. Your contractor will probably appreciate the transparency!

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This is exactly the kind of proactive approach more businesses should take! I'm a new contractor who just started getting paid through various platforms this year, and honestly, the tax implications never occurred to me until I started seeing discussions like this. The idea of including a note with the 1099-NEC explaining potential dual reporting is brilliant - it shows you're thinking about your contractor's experience, not just checking boxes for compliance. As someone who's about to file taxes for the first time as an independent contractor, that kind of heads-up would save me from panicking when I see what looks like double reporting. Quick question for everyone - is there a standard threshold where this becomes an issue? Like, do I only need to worry about getting both forms if I'm making over a certain amount from each client, or does it apply to any payment made through these platforms?

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Great question! I went through this exact same decision last year when starting my consulting business. Here's what I learned: A tax strategist is worth it if you're dealing with complex situations or significant income. For a small side business, I'd suggest starting with what others mentioned - ask your current CPA about proactive planning services first. Many CPAs can handle basic business tax strategy but just don't offer it unless you ask. However, if your CPA seems reactive only or doesn't have experience with your specific business type, a strategist could be valuable. The key is finding one who specializes in small businesses and e-commerce if that's your field. I'd recommend getting quotes from both - ask your CPA what they'd charge for quarterly planning sessions, and get a consultation with a tax strategist to see what they'd recommend. Compare the potential savings each claims they can achieve versus their costs. One thing to consider: as your business grows, your needs will change. Starting with enhanced services from your existing CPA might be the smart move initially, then upgrading to a specialist later if the business takes off.

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This is exactly the kind of balanced advice I was looking for! I think you're right about starting with our existing CPA first. We've worked with him for 4 years and trust him, so it makes sense to see what he can offer before adding another professional to the mix. I'm curious - when you were starting your consulting business, what were some of the first strategic moves that made the biggest difference? Were there any "quick wins" that you wish you'd implemented sooner? Also, did you find that having quarterly planning sessions was enough, or did you need more frequent check-ins during the first year when everything was new?

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Cass Green

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I've been working as a tax professional for over 8 years, and I can tell you that the distinction between CPAs and tax strategists isn't always clear-cut. Many CPAs do provide strategic planning services, but you're right that some focus primarily on compliance and preparation. The real value of strategic tax planning becomes apparent when you're making major financial decisions - like starting a business, changing entity structures, or planning large purchases. For your e-commerce venture, there are several areas where proactive planning could save you money: timing of inventory purchases for tax purposes, setting up proper business entity structure from day one, maximizing home office deductions, and planning for when you might need to transition from sole proprietorship to an LLC or S-Corp. Before hiring a separate strategist, I'd echo what others said about talking to your current CPA first. Ask specifically: "What proactive tax planning services do you offer for new business owners?" and "Can you help us structure our business to minimize taxes as we grow?" If they seem uncertain or just offer basic compliance advice, then it might be time to look elsewhere. A good rule of thumb: if your combined household income plus expected business profit will exceed $100k, strategic planning usually pays for itself. Below that threshold, focus on the basics first - proper record keeping, understanding deductions, and quarterly estimated payments.

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This is really helpful insight from a professional perspective! The $100k threshold makes sense as a practical guideline. I'm curious about the timing aspect you mentioned - when you say "timing of inventory purchases for tax purposes," could you give a specific example of how that might work for someone just starting out? Also, since you mentioned quarterly estimated payments, that's something I'm honestly not sure about. At what point do you typically need to start making those when transitioning from W-2 employee to having business income on the side? Is there a minimum threshold, or is it based on how much you expect to owe at year-end? Thanks for taking the time to share your professional experience - it's exactly the kind of real-world guidance that helps cut through all the conflicting advice online!

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Paolo Rizzo

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Hey Isabella! I was in the exact same boat last year with my Uber Eats and DoorDash income. The good news is you don't need to stress about separating tips from base pay - they're all treated as self-employment income on your taxes. Here's what I learned: Your entire 1099-K amount ($24,680) goes on Schedule C as gross receipts. The IRS doesn't care how much was tips versus base pay because you're an independent contractor, not an employee. What REALLY matters is tracking your business expenses to offset that income. I saved over $3,000 in taxes by properly deducting: - Mileage (this is huge - 67 cents per business mile for 2024) - Phone bill percentage used for work - Hot bags, car phone mounts, etc. - Car maintenance and repairs - Even a portion of car insurance For mileage, if you didn't track everything, try using your delivery history to estimate. Count your total deliveries and multiply by average miles per delivery (usually 3-5 miles depending on your area). TurboTax will walk you through Schedule C step by step when you select "self-employment income." Don't overthink the tip separation - focus on maximizing your legitimate business deductions instead!

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Lia Quinn

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Thanks Paolo! This is super helpful. I'm relieved I don't need to separate the tips. Quick question - when you say "phone bill percentage used for work," how do you figure out what percentage to use? I use my phone for the delivery apps but also personal stuff obviously. Is there like a standard percentage or do I need to track actual usage somehow? Also, do you know if car washes count as a business expense? I definitely wash my car more often now that I'm delivering food to people!

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Isabella, I totally get the panic about that 1099-K amount! I went through the same thing my first year doing gig work. Everyone here is right - you don't need to separate tips from base pay for tax purposes since you're an independent contractor. One thing that might help ease your mind: that $24,680 is your GROSS income, not what you'll actually pay taxes on. After you deduct business expenses on Schedule C, your taxable income will be much lower. Since you mentioned using TurboTax, here's a tip that saved me tons of time: When you get to the self-employment section, TurboTax will ask about your business expenses in plain English. It'll specifically ask about vehicle expenses, and you can choose between actual expenses or the standard mileage deduction (usually better for gig workers). Don't forget about smaller expenses that add up: insulated bags, phone chargers, even hand sanitizer you bought for deliveries. Keep receipts going forward, but for this year, try to estimate what you spent on delivery-related items. The key is being reasonable and honest about your deductions. The IRS expects gig workers to have these types of expenses, so don't be afraid to claim legitimate business costs that helped you earn that income!

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This is exactly the reassurance I needed! The idea that my taxable income will be much lower after deductions makes me feel so much better. I was literally losing sleep thinking I'd owe thousands in taxes on that $24,680. Quick question about the hand sanitizer and small items - do I need receipts for everything or can I estimate some of the smaller purchases? I definitely bought tons of sanitizer, extra phone chargers, and even got a car organizer specifically for deliveries, but I don't have receipts for all of it. Also, when TurboTax asks about vehicle expenses, should I definitely go with the standard mileage deduction? I haven't been tracking my actual car expenses like gas receipts and maintenance costs separately.

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Kylo Ren

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Great question about DIY crawl space encapsulation! I just finished a similar project last month and can confirm you can absolutely claim the tax credits for materials even with DIY installation. The key is making sure your materials qualify - not all vapor barriers and insulation automatically qualify for the credits. A few things I learned during my project: 1. Keep ALL receipts and product documentation 2. Make sure the insulation has proper R-value ratings that meet current energy codes 3. Some vapor barriers qualify if they're part of an integrated insulation system, others don't 4. The 30% credit applies to qualifying materials up to the annual limit One gotcha I discovered - if you're doing this primarily for moisture control rather than energy efficiency, some materials might not qualify. The IRS focuses on the energy efficiency aspect for the credit. But since you mentioned energy efficiency as a goal, you should be good! Your $1,400 in materials could potentially get you around $420 back (30% of qualifying costs), which makes the DIY route even more attractive compared to those $5K contractor quotes. Just document everything well in case of an audit later.

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This is really helpful! I'm curious about the R-value requirements you mentioned - do you know what the minimum R-value needs to be for crawl space insulation to qualify for the tax credit? I want to make sure I buy the right materials from the start rather than finding out later they don't meet the requirements. Also, when you say "integrated insulation system" for vapor barriers, what does that mean exactly? I was planning to install a separate vapor barrier and then add insulation on top, but now I'm wondering if I need to look for some kind of combined product instead.

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For crawl space insulation to qualify for the tax credit, it generally needs to meet the requirements in the International Energy Conservation Code (IECC). For crawl spaces specifically, you're typically looking at R-13 to R-19 minimum depending on your climate zone, but I'd recommend checking the current IECC requirements for your specific area since they can vary. Regarding the "integrated insulation system" - I should clarify that! What I meant is that some vapor barriers come with insulation already attached (like faced insulation batts), and these combination products often have clearer qualification documentation. Your approach of separate vapor barrier plus insulation should work fine too, you just need to make sure both components meet the energy efficiency standards individually. The key thing is that each product needs to have documentation showing it meets federal energy efficiency requirements. Many manufacturers will clearly state "Qualifies for Federal Tax Credit" on qualifying products to make it easier for consumers.

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One thing I haven't seen mentioned yet is that you'll want to check if your state offers additional energy efficiency rebates or credits on top of the federal ones. I did a similar DIY crawl space project in Virginia last year and discovered our state utility company offered rebates for certain insulation materials that stacked with the federal tax credit. Also, since you're doing this as a DIY project, consider getting an energy audit done before you start (some utilities offer free ones). The auditor can help identify exactly which materials and approaches will give you the best energy efficiency improvements for your specific situation. Plus, having that documentation can be helpful if you ever get questioned about the energy efficiency purpose of your improvements. The combination of federal tax credits, potential state rebates, and the DIY savings versus contractor quotes can really add up. In my case, the total savings made it almost a no-brainer decision to do it ourselves!

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Great point about state rebates! I hadn't thought to check what might be available locally. Do you happen to know if those state utility rebates typically require the same material certifications as the federal tax credits, or do they have their own separate requirements? I'm definitely interested in the energy audit suggestion too - did you find that helped you identify specific problem areas you might have missed otherwise? I'm trying to decide if it's worth the time investment before I start buying materials.

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