3 Don't forget that the threshold for filing 1099-MISC for rent is $600 in a calendar year. So if you paid your landlord $600 or more in 2024, you need to file a 1099-MISC. The form is due to the recipient by January 31, 2025 and to the IRS by February 28, 2025 (if filing by paper) or March 31, 2025 (if filing electronically).

9 Hi all, small business landlord here. Please make sure you're sending those 1099s correctly! I've had tenants who either don't send them at all (which is a problem) OR who report the same payment across multiple years (even worse). As others have said, just report what you actually paid in the calendar year. And please double-check the mailing address - I get so many 1099s sent to old addresses even though I've updated my W-9 multiple times.

I think everyone's overthinking this. The IRS isn't going to come after a small yoga business for writing off a few massages lol. I've been writing off all kinds of stuff for years with zero issues.

As someone who's dealt with business deductions for my consulting LLC, I'd strongly recommend being conservative but thorough with your documentation. The retreat classes and workshops are definitely your safest bet - those are clearly professional development expenses that directly relate to your business. For the travel expenses, keep detailed records of your mileage (use the standard IRS rate) and any other transportation costs. If the retreat requires overnight stays to attend multiple days of classes, the lodging becomes more defensible as a business expense. The massage/bodywork question is trickier. While some yoga instructors do deduct these, you'd want solid documentation showing they're truly necessary for your job performance rather than general wellness. A letter from a healthcare provider specifically recommending regular bodywork for injury prevention in your profession would help significantly. My advice: Start conservative in your first year while you're learning the ropes. Focus on the clearly deductible items (classes, necessary travel, business-required lodging) and build up your documentation practices. As you get more comfortable with business tax requirements, you can explore other potential deductions with proper support. Better to leave some money on the table than deal with an audit when you're just starting out!

Just my two cents as someone who's been running a solo 401k for my consulting business for 6+ years: 1. Your custodian doesn't send you or the IRS a form like the 5498 for solo 401k contributions 2. YOU are responsible for tracking which portion is employee deferral vs employer profit sharing 3. Don't forget that the limits are different! For 2025 you can contribute up to $23,000 as employee and then ~25% of your compensation as employer up to the combined limit 4. Once your plan hits $250k in assets, you need to file Form 5500-EZ annually 5. If you ever take a loan from your solo 401k, KEEP IMMACULATE RECORDS The lack of paperwork confused me at first too but I actually like it better this way - one less form to keep track of!

Great question! I went through the exact same confusion when I first started my solo 401k. You're absolutely right that it feels weird not getting any forms like you would with an IRA. The key thing to remember is that solo 401k contributions work completely differently from IRA contributions. Your custodian isn't required to report your contributions to the IRS or send you a 5498 form. Instead, you just track your contributions yourself and they reduce your taxable income on your business return (Schedule C if you're a sole proprietor). For your $23,500 in contributions, make sure you're keeping good records of which portion was employee deferral vs employer profit sharing - this matters for calculating future contribution limits correctly. I keep a simple spreadsheet with dates, amounts, and contribution types. The only time you'll need to worry about filing additional forms is if your total plan assets hit $250,000 - then you'll need to file Form 5500-EZ annually. But at your current contribution level, that's probably still a few years away. You're definitely not overthinking it - the lack of paperwork is actually one of the nice things about solo 401ks once you get used to it!

I went through something very similar with Venmo earlier this year! The SSN request is standard when you hit certain transaction thresholds - it's required for tax reporting purposes, not because they think you're earning income. A few key points from my experience: - Personal reimbursements are NOT taxable income, even if you get a 1099-K - Keep records of your original expenses (hotel, flights, meals, etc.) to show these were legitimate trip costs - If you do get a 1099-K, you'll need to address it on your tax return but can offset it completely by showing these were reimbursements The documentation doesn't have to be perfect - even credit card statements showing you paid for group expenses initially will help establish that friends were just paying you back. I kept screenshots of the payment app transactions with their notes/descriptions too. Don't stress about providing your SSN to Facebook Pay - it's just a compliance requirement. The real key is proper documentation in case you need to explain things to the IRS later.

I've been through this exact situation with multiple payment apps! The SSN request is totally normal - Facebook Pay (now Meta Pay) is legally required to collect this information when you reach certain transaction thresholds for potential tax reporting. Here's what you need to know: - Personal reimbursements are NOT taxable income, period - Even if you receive a 1099-K form, you won't owe taxes on money friends paid you back - The key is proper documentation showing these were legitimate expense reimbursements For your records, keep: - Receipts/statements showing you originally paid for trip expenses - Screenshots of the Facebook Pay transactions with any notes about what they were for - A simple list matching each payment to the original expense it covered If you do get a 1099-K, you'll report it on your tax return but then subtract the same amount as "nontaxable personal reimbursements" - so zero net tax impact. Don't stress about providing your SSN, it's just a compliance requirement. The important thing is having documentation that shows these payments were just friends settling up trip expenses, not income you earned.

FYI - there's actually a tax court case about this exact situation from last year. Guy with Cayman corp tried to argue he didn't owe US tax because the business had no US connection. Judge basically laughed him out of court and he owed back taxes plus penalties. US citizenship = US tax on worldwide income. Period.

As a US citizen, you absolutely need to report this capital gain on your personal tax return. The fact that your corporation is in the Cayman Islands doesn't shield you from US tax obligations - US citizens are taxed on worldwide income regardless of where it's earned. Since you and your brother likely own more than 50% of this foreign corporation, you're dealing with Controlled Foreign Corporation (CFC) rules. This means you may have had ongoing reporting obligations (Form 5471) even before the sale. The capital gain from selling your shares is definitely taxable as a long-term capital gain since you held them over a year. A few critical things to consider: 1) You may owe taxes on undistributed earnings from prior years under Subpart F or GILTI rules, 2) Don't forget FBAR filing requirements if you had signature authority over company accounts exceeding $10k, and 3) You might also need Form 8938 depending on the value of your foreign assets. I'd strongly recommend getting a qualified international tax attorney or CPA who specializes in foreign corporations. The penalties for getting this wrong can be severe - I've seen cases where people owed more in penalties than the actual tax due. This is definitely not a DIY situation given the complexity of CFC rules and international reporting requirements.