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One trick that has worked for me twice now when dealing with the IRS - call your local congressional representative! Most have staff dedicated to helping constituents with federal agencies. I called my rep's office, explained my situation, and within 2 weeks they had contacted the IRS and gotten my issue resolved. Their office has direct channels to IRS advocates that regular people can't access.
Does this really work? I've heard about this but wasn't sure if congressional offices actually help with tax stuff or if they just take your info and do nothing.
Yes, it absolutely works! Congressional caseworkers help constituents navigate federal agencies - it's literally part of their job. When I called, they had me fill out a privacy form so they could legally inquire about my case, then assigned a caseworker who contacted the IRS Taxpayer Advocate on my behalf. The key is being patient and polite with their office. They deal with lots of cases, so don't expect immediate results, but in my experience, they did follow through. It took about 2 weeks to get resolution, which was much faster than I was getting on my own. Just call your rep's local district office rather than their DC office for best results.
Has anyone tried setting up an in-person appointment at a local IRS office? I've heard you can do that but haven't tried it myself.
Has anyone used the simplified home office deduction for their side business? It's $5 per square foot up to 300 square feet instead of calculating all the actual expenses. Seems easier if you qualify!
I use the simplified method for my Etsy shop and it's so much easier than tracking all those expenses. But remember you still need a space that's EXCLUSIVELY for business use. I converted a small closet (about one-sixth of my apartment's square footage) to store inventory and take product photos, and I only claim that area.
Important point: make sure you're documenting everything in case you get audited. Take photos of your office space, keep receipts for all business purchases, maintain a log of when you use the space for business vs. employment, etc. Trust me, you do NOT want to be scrambling for documentation if the IRS comes knocking!
One thing nobody mentioned yet - look into the First Time Penalty Abatement program from the IRS. If you haven't had any issues in the 3 years before your first missed filing, you might qualify to have penalties waived for one tax year. Won't help for all 15 years but could save you some money on at least the first year's penalties. Also check your state's voluntary disclosure program. Some states have amnesty options if you come forward voluntarily before they come after you (though sounds like they already found you in the past).
Thank you for mentioning this! I had no idea about the First Time Penalty Abatement program. Do you know if I would still qualify even though they had already levied my bank account years ago?
Unfortunately, since they've already taken collection actions like bank levies, you probably won't qualify for First Time Penalty Abatement. That program is typically for taxpayers who haven't had prior issues. However, you might still qualify for abatement under "reasonable cause" if you can demonstrate that your failure to file and pay was due to circumstances beyond your control - things like serious illness, inability to obtain records, or certain types of hardship. The anxiety and depression you mentioned might actually help your case, especially if you have any documentation from a healthcare provider.
Quick question - do you have any retirement accounts or investments you can liquidate to pay this off? I was in a similar situation (8 years unfiled) and ended up taking the hit on an early 401k withdrawal to clear my tax debt. The 10% penalty hurt but it was worth it to wipe the slate clean and stop the interest from continuing to accrue.
Have you considered the actual Standard Mileage Rate instead of tracking actual expenses? For 2023 it's 65.5 cents per mile for business use. This includes ALL vehicle costs including fuel (or in your case, electricity). Much simpler than tracking individual expenses.
I did think about the standard mileage deduction, but from what I've calculated, the actual expense method will probably be more beneficial in my case. I drive the EV almost exclusively for business, and with the depreciation of the vehicle plus all the other expenses, I think I'll come out ahead with actual expenses. But you're right that standard mileage would definitely simplify things!
The standard mileage rate doesn't actually work well for EVs in many cases. It was designed around gas vehicles and their maintenance costs. EVs have higher upfront costs but lower per-mile costs, so you might be leaving money on the table using standard mileage.
Slightly off topic but make sure you're also claiming the EV charger installation cost as a business expense if you haven't already! I was able to deduct 80% of my Level 2 charger installation since I use my car primarily for business. Saved me about $800 in taxes last year.
What documentation did you need to prove the business use percentage? I'm getting a charger installed next month and want to make sure I have everything ready for tax time.
Nia Jackson
One thing nobody has mentioned yet about MMLLC vs S-corp - operating agreements are SUPER important, especially with 4 partners. Make sure you have detailed provisions for: - How profits/losses are allocated (doesn't have to be equal to ownership %) - What happens if someone wants out - Management responsibilities and voting rights - Capital contribution requirements My brother-in-law's multi-member LLC imploded because they didn't have this stuff spelled out clearly. The tax structure matters, but the operating agreement will save you major headaches.
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Freya Pedersen
ā¢This is really helpful! We have a basic operating agreement drafted but haven't addressed the profit/loss allocation part in detail. Would you recommend getting a specialized business attorney to help with this, or are there good templates we could use as a starting point?
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Nia Jackson
ā¢I would absolutely recommend getting a specialized business attorney for this. Templates are a starting point, but with four partners and potentially complex profit-sharing arrangements, you need customization. The attorney cost us about $1,500 for a solid operating agreement, but it was worth every penny. For your escape room business, you'll want specific provisions that address how to handle capital-intensive improvements, marketing expenses, and the sweat equity some partners might contribute versus purely financial investments. The attorney can also help structure things to maximize the tax benefits whether you go MMLLC or S-corp route. Think of it as insurance against future partner disputes.
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Mateo Hernandez
A practical tip from someone who runs 2 escape rooms: regardless of whether you go MMLLC or S-corp, set up good bookkeeping from DAY ONE. Our first year was a nightmare at tax time because we mixed personal and business expenses and didn't track properly. QuickBooks Online worked well for us, but there are cheaper options like Wave that are good too. Just make sure you're categorizing everything correctly and keeping good records of all your startup costs (which can be substantial for escape rooms with all the props and tech).
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CosmicCruiser
ā¢Does QuickBooks handle the S-corp payroll stuff well? We're starting a similar business and I'm worried about getting the whole "reasonable compensation" thing right.
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