One additional consideration that hasn't been mentioned yet - if your LLC units are subject to vesting and the company hasn't sold yet, make sure you understand what happens if you leave the company before the liquidity event. Many LLC operating agreements have "bad leaver" provisions that could affect your tax treatment or even result in forfeiture of unvested units. Also, since you mentioned the units only vest upon sale or IPO, you'll want to confirm whether there are any interim valuation events that could trigger partial vesting or affect your basis calculation. Some agreements have provisions for secondary sales or tender offers that could complicate the tax picture. The 83(b) election protects you from ordinary income treatment at vesting, but it doesn't necessarily protect against forfeiture provisions in your grant agreement. Worth reviewing those terms with both a tax professional and potentially an employment attorney if there are significant amounts at stake.

This is a really comprehensive discussion! One aspect I'd add that might be relevant to your situation - make sure you understand how the LLC's depreciation recapture (if any) might affect your sale. Even though you filed an 83(b) election, if the LLC has been taking depreciation deductions on assets over the years, some portion of your gain could be subject to depreciation recapture at ordinary income rates rather than capital gains rates. This is separate from the Section 751 "hot assets" issue that was mentioned earlier, but can similarly convert what you expect to be capital gains into ordinary income. The LLC should provide this information when the sale occurs, but it's worth asking about proactively so there are no surprises. Also, given that you've held these for 9 years, you might want to consider whether any tax-loss harvesting opportunities in your portfolio could help offset the capital gains when you do sell. Since this sounds like it could be a significant gain, having a tax planning strategy in place before the sale completes could save you quite a bit in taxes.

Just wanted to share that depending on your total tax debt amount, another option is to request what's called a "tiered" installment agreement from the IRS. I had a similar situation last year, and the IRS set me up with a plan where I paid a higher amount for the first 12 months to clear the newer tax debt, then my payment dropped down to the original amount for the remainder of the older debt. The benefit was that it looked like one continuous agreement rather than a defaulted one that got modified. Might be worth asking about when you call!

I actually work as a tax professional and deal with these situations regularly. The confusion you encountered is unfortunately very common because the IRS has different procedures depending on when you call and which department you reach. Here's what's really happening: The IRS system is designed to automatically flag installment agreements as defaulted when new tax debt posts to your account. However, there's a difference between a "systemic default" (which happens automatically) and an "administrative default" (which results in collection actions). The key is calling within 30 days of when the new assessment posts. During this window, you can request what's called a "modification" rather than starting a completely new agreement. This keeps your payment history intact and avoids the more serious consequences of a true default. My advice: File your 2022 return ASAP, then monitor your online IRS account transcript. The moment you see the new balance assessment appear, call immediately to request the modification. Be specific that you want to "modify your existing installment agreement to include the new tax year" rather than saying you want to "restart" or "set up a new" agreement. The exact wording matters with IRS representatives.

One thing everyone forgot to mention - if you decide to depreciate rather than using Section 179, and your business has a bad year or closes before the depreciation period ends, you can't just deduct the remaining value all at once. Something to consider if your business fluctuates a lot! This happened to my friend's videography business and he lost out on thousands in potential deductions.

Great question! Yes, you can absolutely deduct equipment purchases made with loan funds. The IRS doesn't care where the money came from - what matters is that it's a legitimate business expense. A few key points for your photography LLC: 1. **Section 179 vs Depreciation**: For $12,500 in equipment, you'll likely want to use Section 179 to deduct the full amount in the first year rather than depreciating over time. Much simpler and gives you the tax benefit immediately. 2. **Documentation**: Keep clear records linking the loan to the equipment purchases. Save receipts, invoices, and loan documents showing the funds were used for business purposes. 3. **Don't forget loan interest**: While the loan principal isn't deductible, the interest you pay on that business loan is a separate deductible expense throughout the life of the loan. 4. **Mixed-use equipment**: If any equipment might be used personally (like a camera you occasionally use for family photos), you can only deduct the business percentage. Since you're an LLC, you'll handle this on Schedule C of your personal return (assuming single-member LLC). The deduction will reduce your taxable business income, which flows through to your personal taxes. Definitely worth consulting a tax pro for your specific situation, but the basic principle is solid - loan-funded business expenses are still deductible business expenses!

I want to share my experience as someone who went through a similar situation last year. I was offered $8,000 in cash for helping with landscaping work, and I was really tempted to just not report it. But after reading about the potential consequences, I decided to do the right thing and report it properly. It ended up being much less painful than I expected. I filed Schedule C for the self-employment income, but I was also able to deduct expenses like gas for my truck, tools I bought, and even part of my cell phone bill since I used it for work coordination. After all the deductions, I only owed taxes on about $5,500 of the income. The peace of mind has been worth it. I sleep better knowing I'm not looking over my shoulder wondering if the IRS will catch up with me someday. Plus, now I have a legitimate track record of self-employment income that could help if I ever want to apply for a loan or mortgage. My advice: report the income, keep good records of your expenses, and consider it a learning experience for handling taxes as a freelancer. It's really not as scary as it seems when you do it properly from the start.

I really appreciate seeing all the different perspectives here. As someone who's dealt with tax issues in the past, I want to emphasize that reporting the income is absolutely the right call, even though it might seem like a hassle now. One thing I haven't seen mentioned yet is that if you're going to be doing this type of work regularly, you might want to consider getting an EIN (Employer Identification Number) from the IRS. It's free and makes you look more professional when working with clients. You can also open a separate business bank account, which makes tracking income and expenses much cleaner come tax time. Also, don't forget about state taxes if your state has income tax. You'll need to report this income there too, but the good news is that most business expenses that reduce your federal taxes will also reduce your state taxes. The most important thing is to start keeping detailed records from day one. I use a simple spreadsheet to track every dollar that comes in and every business expense that goes out. It makes tax season so much easier when everything is already organized.

This is such a common confusion point for self-employed folks! I've been dealing with conference expenses for years as a freelance consultant. One thing I'd add to the great advice already given - make sure you keep detailed records of not just the receipts, but also the business purpose of each trip. The IRS likes to see documentation that shows the conference was directly related to your business. I always save the conference agenda, any certificates of completion, and notes about what I learned that I applied to my work. Also, if you're claiming meals during the conference, remember those are typically only 50% deductible (unless it's a company event where meals are provided to all attendees). The flight, hotel, and conference registration are usually 100% deductible as long as the trip is primarily for business. For your specific situation with the $3,200 in total expenses, that's definitely worth getting right on the timing. The cash basis method that others mentioned is definitely the way to go for most self-employed people - deduct when you pay, not when you use the service.

This thread has been incredibly helpful! As someone who's been self-employed for about 3 years now, I've always been paranoid about getting business travel deductions wrong. One thing I'd add that might be useful - if you're using a business credit card for these expenses, it makes the record-keeping so much easier. My business card automatically categorizes travel expenses and the statements clearly show purchase dates vs. service dates. It's been a lifesaver for situations exactly like yours where you buy tickets in December for February travel. Also, for anyone reading this who's newer to self-employment - don't forget that you can also deduct ground transportation to/from the airport (parking, rideshare, etc.) and even tips for hotel staff if they're reasonable. These smaller expenses add up over multiple business trips throughout the year. The key takeaway from all the great advice here seems to be: deduct when you pay (with some exceptions for multi-year prepaid services), keep excellent records with business justification, and when in doubt, consult the IRS directly or work with a tax professional. Better to get it right than deal with an audit later!