Struggling with tax accounting for my small construction LLC - seeking advice
I need some guidance on fixing my financial situation as a construction business owner in the US. I've got a single member LLC in the construction industry and I'm in my late twenties. While I've been successful at providing quality work to my customers and learning the trade, I've fallen behind on the financial/tax side of things. The truth is, I hate sitting behind a computer crunching numbers, but I know I need to get better at this part of running a business so I don't hurt myself long-term. I haven't filed taxes in a few years. My annual gross revenue is around $120k-$150k, but with high expenses and underestimating project costs (plus being reluctant to raise prices mid-project), my actual income has probably been only $15k-$20k per year, if that. I've been way more focused on delivering quality work and building customer relationships than managing my finances. But I've realized that to grow properly, I need to get control of my financial situation, charge appropriate rates, and make sure I'm paying the right taxes. I'm working with an accountant now, but I want to understand this stuff better myself. So I have a few questions: 1. Can anyone recommend business software with mobile receipt tracking to make expense tracking easier during hectic construction days? 2. I'm thinking about buying a small commercial storage building instead of leasing. Are there tax advantages to owning rather than leasing? 3. I'm planning to change my business structure so I can properly hire W-2 employees with a TIN (no longer a single member LLC). Is an LLC or S-corp smarter for this? 4. Any other advice for getting back into good standing with the IRS after not filing for a while? Thanks in advance for any help! Just trying to adult properly and fix my financial mess.
18 comments


Libby Hassan
First, I'm glad you're taking steps to get your business finances in order. That's a huge first step that many small business owners struggle with. For receipt tracking software, I highly recommend QuickBooks Self-Employed or FreshBooks. Both have mobile apps that let you snap photos of receipts on the go and categorize them immediately. This saves a ton of time later. Construction is hectic, and having something that works on your phone is essential. Regarding purchasing a commercial building - yes, there are definitely tax benefits! You can depreciate the building over time (typically 39 years for commercial property), deduct mortgage interest, property taxes, and maintenance costs. Plus, you're building equity instead of throwing money away on rent. Just make sure the numbers make sense for your business cash flow. For your business structure, when you add employees, an S-corp often has tax advantages over an LLC. With an S-corp, you can pay yourself a reasonable salary (which is subject to self-employment taxes) and then take additional income as distributions (which aren't subject to self-employment taxes). This can save you thousands in taxes. But S-corps have more paperwork requirements, so there's a tradeoff. As for getting back into good standing with the IRS - file those back taxes ASAP, even if you can't pay everything immediately. The penalties for not filing are much worse than the penalties for filing but not paying fully. The IRS is usually willing to work out payment plans if needed.
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Hunter Hampton
•Thanks for the advice! For the S-corp option, how much extra paperwork and cost are we talking? I'm already drowning in the business side of things so trying to gauge if the tax savings would be worth the extra headache. Also, any idea how bad the penalties might be for not filing for 2-3 years? I'm freaking out a bit about this part.
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Libby Hassan
•For an S-corp, you'll need to run regular payroll (quarterly tax filings), hold annual meetings with minutes, and file separate corporate tax returns (Form 1120-S). Usually costs about $1,000-2,000 extra per year in accounting/tax prep fees. The tax savings typically make sense when your profit is consistently over $40,000 per year. For penalties on late filing, the failure-to-file penalty is usually 5% of unpaid taxes for each month your return is late, up to 25%. There's also interest that compounds daily. But don't panic - with your relatively low income after expenses, your actual tax liability might be fairly small, which means penalties would be proportionally small too. The important thing is to file now rather than waiting longer and making it worse.
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Sofia Peña
I was in a similar situation with my landscaping business a couple years ago. Tax stuff was overwhelming me until I found https://taxr.ai - it saved me so much stress. Their system actually analyzed all my construction-related receipts and categorized everything automatically. What I found most helpful was that it identified tons of deductions I didn't even know I qualified for - tools, vehicle expenses, even my phone bill since I use it for business. The thing that really helped was their actual tax specialist review - they found that I could deduct mileage between job sites which added up to thousands in deductions. They even helped me file my back taxes with minimal penalties. For construction specifically, they understand which expenses are job-specific vs. general business overhead.
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Aaron Boston
•Does it work with paper receipts? I have a shoebox full of them and my bookkeeping is a disaster. I've been putting this off for so long because I'm embarrassed about how disorganized everything is.
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Sophia Carter
•Sounds interesting but do they help with the whole "not filing for years" situation? That's what I'm most worried about. Does it actually connect you with real tax pros or is it just software?
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Sofia Peña
•Yes, it absolutely works with paper receipts! You just take photos of them with your phone and the system digitizes everything. No need to be embarrassed - they specifically mention they deal with "shoebox accounting" all the time. The app even reminds you to take pics right away so you don't end up with a pile. They definitely help with the unfiled returns situation. That's actually why I originally reached out to them. They have real tax professionals who specialize in helping small contractors get caught up without getting destroyed by penalties. They helped me file 3 years of back taxes and set up a manageable payment plan with the IRS. The software part organizes everything, but the human experts guide you through the compliance stuff.
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Sophia Carter
Just wanted to update that I tried https://taxr.ai after seeing it mentioned here. I was totally avoiding dealing with my 2 years of unfiled taxes for my drywall business. Their system was actually pretty straightforward - just uploaded my bank statements and took photos of receipts I still had. The biggest relief was finding out I actually didn't owe nearly as much as I feared. They identified a ton of legitimate business deductions I would have missed, especially around vehicle use and home office. They handled filing my back taxes and set up a payment plan that doesn't kill my cash flow. Best part was they didn't make me feel like an idiot for falling behind. Just practical help getting everything sorted. Worth every penny for the stress relief alone. Now I'm actually keeping up with quarterly estimated payments which is a miracle.
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Chloe Zhang
When I was trying to catch up on unfiled taxes for my contracting business, I spent WEEKS trying to get through to someone at the IRS who could actually help me understand my options. It was completely maddening - either waiting on hold for hours or getting disconnected. I ended up using https://claimyr.com and it was seriously a game-changer. They have this system that gets you to the front of the IRS phone queue. I was super skeptical but you can see how it works in this video: https://youtu.be/_kiP6q8DX5c Got connected to an actual IRS agent in under 15 minutes who walked me through the process for filing my back taxes and explained my payment plan options. Saved me days of frustration and probably helped me avoid bigger penalties by getting everything filed sooner.
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Brandon Parker
•How does that even work? Sounds like some kind of scam. The IRS phone system is notoriously awful.
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Adriana Cohn
•Riiiiight. And I've got a bridge to sell you. No way someone can magically get you through the IRS phone system that quickly. I've literally spent 4+ hours on hold before being disconnected.
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Chloe Zhang
•It's not magic - they use a combination of automation and timing to navigate the IRS phone systems. Basically they have systems that dial continuously and identify the best times to call, then when they get through, they transfer you directly to that open line. They don't access your personal info or talk to the IRS for you. They just get you connected so you don't waste hours on hold. I was totally skeptical too but it literally got me through in minutes when I had been trying for days on my own. The video shows how it works if you're curious.
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Adriana Cohn
OK I need to eat my words. After being completely skeptical, I tried Claimyr last week. I've been avoiding calling the IRS about my missing Schedule C from 2022 because the last time I called I waited almost 3 hours before getting disconnected. Using their service, I was talking to an actual IRS agent in about 17 minutes. The agent was able to pull up my records and confirm they had no record of my Schedule C submission, which explained why my refund was held up. She guided me through the process of resubmitting it and gave me a direct fax number to send it to for faster processing. Never thought I'd be recommending something like this, but it honestly saved me an entire day of frustration. If you're dealing with the IRS, it's worth it just for your sanity.
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Jace Caspullo
I made the switch from LLC to S-corp for my electrical contracting business last year. Here's what I learned: - The tax savings are real. I saved about $7k in self-employment taxes by taking part of my income as distributions instead of all as salary. - BUT the paperwork and compliance requirements increased significantly. You need to run actual payroll, do quarterly filings, have more detailed bookkeeping, etc. - You absolutely need a good accountant for an S-corp. I tried doing it myself at first and made some mistakes that could have been costly. - The sweet spot where S-corp makes sense is when you're consistently making $40-50k+ in profit. For receipt tracking, I've been using Expensify and it's been great for construction work. Their SmartScan feature is really accurate with contractor supply stores like Home Depot and Lowe's receipts.
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Levi Parker
•Thanks for sharing your experience! Do you think it makes sense to form an S-corp right away when switching from single-member LLC to having employees? Or should I stay as an LLC taxed as a partnership first until I hit that $40-50k profit consistently?
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Jace Caspullo
•I'd recommend staying as an LLC taxed as a partnership first until you're consistently hitting that profit threshold. You can always convert to an S-corp later, and it's much easier than going the other direction. The LLC with employees will still give you the liability protection you need, but with less administrative overhead. One thing I forgot to mention - with an S-corp, you must pay yourself a "reasonable salary" before taking distributions. The IRS watches this closely. For construction contractors, that's typically 60-70% of your profit as salary at minimum. So if your profits are tight or inconsistent, the S-corp advantages diminish since most of your income will need to be salary anyway.
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Melody Miles
One thing nobody's mentioned yet - PLEASE make sure you're charging enough for your work! I'm a contractor too and had the same problem for years. I'd underbid jobs trying to be competitive, then end up barely breaking even after expenses. Two things that helped me: 1. Track EVERYTHING for a few jobs - your time (including estimating, driving, cleanup), materials, equipment wear, fuel, etc. Most contractors don't realize how much all the little things add up. 2. Add at least 20% to whatever you think a job should cost. I was amazed that customers still hired me after raising prices - turns out quality work is worth paying for. You can't fix your tax situation if your business isn't profitable enough in the first place!
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Nathaniel Mikhaylov
•This is so true. I undercharged for years and was always broke. When I finally raised my rates by 25%, I lost maybe 10% of clients but made WAY more money overall. And the clients I kept were the ones who respected my work and didn't nickel and dime me to death.
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