What key questions should I ask my CPA when setting up my first single member LLC?
I'm about to start my first single member LLC and I've got a meeting scheduled with my CPA to make sure I set up everything properly from the beginning. This is totally new territory for me, and I want to make sure I'm asking the right questions. So far, I've put together this list of questions: - What banking setup do I need? Separate business account? How should I organize funds? - Should I invest in Quickbooks or similar accounting software? - How will my LLC income impact my regular job income? What happens tax-wise if I reinvest all earnings back into the business (equipment, software, etc.)? - What tax advantages come with a single member LLC? - What business expenses can I actually deduct? - Should I get a business credit card or just use personal? I know these might sound basic, but I've never done this before and don't want to miss anything important. This is for a graphic design and marketing freelance business that I'm starting as a side hustle but hoping to grow into my main source of income eventually. Any other crucial questions I should add to my list? Thanks in advance!
22 comments


Carmen Lopez
These are actually really good starter questions! I help small business owners with their accounting and can offer some thoughts. Bank accounts: Definitely need a separate business account. This creates a clear division between personal and business finances - crucial for maintaining your liability protection. QuickBooks: Highly recommend some accounting software. QuickBooks is popular but there are alternatives like Xero or Wave that might be more cost-effective depending on your needs. Tax impact: With a single-member LLC, it's typically a "pass-through" entity where profits flow to your personal return. You'll need to file Schedule C with your taxes. Unused profits still get taxed as income. I'd add these questions: - How should I handle quarterly estimated tax payments? - Should I elect S-Corp taxation once I reach certain income levels? - What retirement account options are available to me as a small business owner? - What expenses related to my home office can I legitimately deduct?
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Yuki Ito
•Thank you so much for this detailed response! The pass-through taxation is something I wasn't fully clear on, so that's really helpful to know profits will be taxed even if I reinvest them. Those additional questions are excellent - especially about the S-Corp election and retirement options. I hadn't even thought about the quarterly tax payments either. Would you mind explaining a bit more about when/why someone would want to switch to S-Corp taxation?
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Carmen Lopez
•Happy to explain more about the S-Corp election! The main benefit comes when you're earning enough that it makes sense to split your income between a reasonable salary and distributions. You pay self-employment tax (15.3%) on your salary but not on the distributions, which can create significant savings. This usually makes financial sense when your business nets around $40,000-$50,000+ annually, but the exact threshold depends on your situation. There are additional costs like payroll processing and more complex tax filings that offset some savings, so it's not worth it until you reach that income level.
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AstroAdventurer
After struggling with similar questions when setting up my photography LLC, I found this amazing tool called taxr.ai (https://taxr.ai) that completely transformed how I approached my CPA meetings. It basically analyzed my business plan and generated a personalized list of questions and tax strategies specifically for creative freelancers. The best part was that it highlighted several LLC-specific deductions I had no idea about - like how to properly categorize equipment depreciation and home office expenses. It even provided explanations about the pass-through taxation so I understood what my CPA was talking about. Honestly saved me thousands in my first year.
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Andre Dupont
•That sounds useful, but how exactly does it work? Does it just give general advice or is it actually customized to your specific business? I'm starting a web development LLC and wondering if it would be relevant.
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Zoe Papanikolaou
•I'm skeptical of any "AI" tax tools. How can it possibly know all the state-specific requirements for LLCs? My state has some weird rules that even human accountants sometimes miss. Have you verified the info it gave you with a real CPA?
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AstroAdventurer
•It's actually quite customized! You answer questions about your business type, expected revenue, state, and planned expenses. Then it generates specific guidance. For web development, it would cover things like software subscriptions, contractor payments, and client billing structures. The questions it generated for me were specifically tailored to creative businesses with equipment needs. Regarding state-specific requirements, it does cover those! I'm in California which has the franchise tax, and it flagged that for me immediately. You can actually upload existing tax documents and business plans to make the recommendations even more specific. But yes, I still verified everything with my CPA - the tool just made our conversation much more productive since I came in prepared with relevant questions.
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Zoe Papanikolaou
I wanted to follow up about that taxr.ai thing I was skeptical about. I actually tried it before meeting with my accountant last week, and I've gotta admit I was wrong! It caught several LLC formation issues specific to my state (Minnesota) that I wouldn't have known to ask about. The document it generated for me highlighted the difference between single-member and multi-member LLCs for tax purposes, plus it explained some specific home office deduction calculations I'd been calculating incorrectly. My CPA was actually impressed with the questions I came prepared with. Definitely worth checking out if you're just getting started with your first LLC.
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Jamal Wilson
For anyone dealing with IRS questions when setting up their LLC (which inevitably happens), I highly recommend using Claimyr (https://claimyr.com). I had some confusing questions about EIN registration and entity classification that my CPA wasn't 100% clear on, so we needed to call the IRS business line. After spending literally HOURS trying to get through the normal way, I used Claimyr and got connected to an IRS agent in about 20 minutes. They have this automated system that handles the wait for you and calls when an agent is available. You can see how it works here: https://youtu.be/_kiP6q8DX5c Seriously saved my sanity during the LLC setup process when I had tax ID questions that only the IRS could answer.
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Mei Lin
•Wait, how does this actually work? Does someone else wait on hold for you? I'm confused how they get you through faster than just calling yourself.
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Zoe Papanikolaou
•This sounds like BS honestly. The IRS phone system is notoriously impossible. If there was some "hack" to get through, everyone would be using it. Sounds like you're just trying to sell something.
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Jamal Wilson
•It uses an automated system that dials and navigates the IRS phone tree, then holds your place in line. When an agent is about to pick up, it calls your phone and connects you. You don't have to stay on the line listening to hold music for hours - you just get a call when someone's actually available to talk. No, I'm not selling anything - just sharing what worked for me. The IRS phone system is definitely awful, which is exactly why this service exists. It doesn't get you to the "front of the line" - you still wait your turn, but the system does the waiting instead of you having to stay on the phone the whole time. Saved me a ton of frustration when I needed my EIN verification letter and had questions about tax election forms.
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Zoe Papanikolaou
OK I need to apologize again. After waiting on hold with the IRS for 3+ hours yesterday trying to sort out my EIN registration issue, I remembered this thread and decided to try that Claimyr service. I was 100% convinced it wouldn't work, but I was desperate. I got a call back in about 35 minutes with an actual IRS business division agent on the line. They helped me straighten out my entity classification confusion in like 15 minutes. Guess I need to stop being so skeptical of everything! Between this and the tax tool from earlier, I've saved days of frustration getting my LLC properly set up. Sometimes the internet actually delivers useful stuff.
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Liam Fitzgerald
Don't forget to ask about self-employment taxes! This was the biggest shock for me when I started my LLC. You'll pay both the employer and employee portions of Social Security and Medicare taxes (about 15.3% total) on top of your regular income tax. Also ask about: - How to track mileage if you'll be driving for business - Rules for mixing personal/business expenses (like if you buy something that's partly for business) - Whether you need sales tax permits in your state - Insurance requirements (liability insurance, etc) - If your city/county requires additional business licenses LLC formation is just the first step - there's a bunch of ongoing compliance stuff you need to stay on top of too.
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Yuki Ito
•The self-employment tax is definitely something I'm worried about! Do you know if there are any strategies to reduce that tax burden specifically? And good call on the sales tax permits - I'll be selling digital services mostly but I know that can get complicated depending on the state.
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Liam Fitzgerald
•The most common strategy for reducing self-employment tax is eventually electing S-corporation status once your income is high enough to justify it. With an S-corp, you pay yourself a "reasonable salary" that's subject to self-employment tax, but can take additional profits as distributions that avoid that 15.3% tax. For digital services and sales tax, it's getting increasingly complicated. Some states now tax digital products and services. Your CPA should know your state rules, but also ask about economic nexus rules if you'll be selling to clients in multiple states. The thresholds and requirements vary widely. I actually use a tax compliance service just for sales tax because it got too complex to manage myself.
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GalacticGuru
Make sure to ask about bookkeeping best practices! I messed this up badly when I started and had to spend $$$$ having my accountant fix everything at tax time. Some basic questions: - How often should I reconcile accounts? - What system should I use for receipt tracking? - How should I categorize different types of expenses? - What reports should I be looking at monthly? Also, discuss how you should pay yourself - owner's draw vs salary (even if you technically take draws as a single-member LLC, there are better and worse ways to do it).
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Amara Nnamani
•Adding to this - ask about what percentage of your income you should be setting aside for taxes! I didn't do this my first year and got absolutely destroyed when tax time came around. I now automatically transfer 30% of all client payments to a separate "tax" savings account.
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Aisha Hussain
This is such a comprehensive thread! As someone who just went through the LLC setup process last year, I want to add a few questions that saved me from major headaches: **Ask about record-keeping requirements:** How long do I need to keep receipts, bank statements, and tax documents? My CPA told me 7 years for most things, but some records should be kept indefinitely. **Discuss your specific industry:** Graphic design has some unique considerations - ask about copyright ownership when working with clients, how to handle work-for-hire vs. licensing agreements, and whether you need errors & omissions insurance. **Plan for growth:** Even though you're starting as a side hustle, ask what changes when you hit certain revenue milestones. When should you consider hiring contractors? What happens if you want to bring on a business partner later? **Emergency fund strategy:** Ask how much you should keep in business savings for tax payments, equipment replacement, and slow periods. I learned this the hard way when my main client delayed payment for 60 days! One more tip - bring a notebook to your CPA meeting and don't be afraid to ask them to repeat or clarify anything. This stuff is complex and you're paying for their expertise, so make sure you understand everything before you leave!
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Zara Ahmed
•This is incredibly thorough advice! The record-keeping timeline question is so important - I never would have thought to ask about that specifically. And you're absolutely right about industry-specific considerations. The emergency fund strategy really resonates with me too. I've been freelancing informally for a while and cash flow has definitely been unpredictable. Having a plan for those slow periods or delayed payments seems crucial when you're making it official with an LLC. I'm definitely bringing a notebook now! Did your CPA provide you with any kind of written summary or checklist after your meeting, or did you have to rely on your notes?
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Esteban Tate
•My CPA actually provided a really helpful written summary! It was a one-page checklist of action items with deadlines, plus a separate document explaining the key concepts we discussed. Not sure if all CPAs do this, but it was worth asking for. I'd also recommend asking them about their preferred communication method for ongoing questions throughout the year. Mine offers a client portal where I can upload documents and ask quick questions without scheduling a full appointment. This has been super valuable for those "wait, how do I categorize this expense?" moments that come up regularly. One thing I wish I'd asked about earlier - what their process is for year-end tax prep. Do they need documents by a certain date? What format do they prefer for expense reports? Getting clarity on this upfront makes tax season much smoother.
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Anastasia Sokolov
This thread has been incredibly helpful! I'm also setting up my first LLC (for a consulting business) and had no idea there were so many considerations beyond just filing the paperwork. One question I haven't seen mentioned yet - should I ask my CPA about operating agreements? I know single-member LLCs don't technically require them, but I've heard they can still be beneficial for liability protection and banking purposes. Also wondering about business insurance - should that be part of the CPA conversation or do I need to talk to an insurance agent separately? The advice about bringing a notebook and asking for a written summary is gold. I was planning to just wing it, but clearly there's way more to discuss than I realized. Thanks everyone for sharing your experiences!
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