ask him to explain EXACTLY what deductions or credits he's planning to use that turbotax isn't giving you. if he can't explain it clearly or gets defensive, run away!!!! my cousin's tax guy did this last year, claimed a bunch of fake business expenses and education credits she didnt qualify for. she ended up getting audited and had to pay back $4200 plus penalties!!!

This sounds like a classic case of a preparer who's going to claim deductions you don't qualify for. The jump from $1,450 to $3,200+ for a straightforward W-2 + side gig situation is a huge red flag. Here's what I'd recommend: Before you give this guy any documents, ask him to write down exactly which deductions or credits he plans to claim that TurboTax missed. If he mentions anything about business expenses for your W-2 job, home office deductions you don't qualify for, or education credits you're not eligible for - walk away immediately. The "knows all the tricks" line is what every shady preparer says. Legitimate tax professionals explain their strategies clearly because they're following actual tax law, not trying to game the system. Remember, even if this guy prepares your return, YOU are the one who signs it and YOU are responsible if the IRS comes after you for improper deductions. The extra $1,750 he's promising could easily turn into thousands in penalties and interest if you get audited. Trust your gut - if it feels too good to be true, it probably is. Stick with reputable software or find a CPA who will explain their work transparently.

Has anyone had luck getting an IP PIN with a foreign address? I'm an expat living abroad and can't get past the address verification step in the online system. The international IRS number is even harder to get through on than the domestic one.

I went through this exact same nightmare last year! What worked for me was creating an IRS online account first at irs.gov/account. Once you have that set up, you can access the "Get an IP PIN" tool more easily. The key thing that helped me was having my prior year tax return handy - you'll need the exact AGI (Adjusted Gross Income) from line 11 of your 2023 Form 1040. Also make sure you're using a phone number that's been in your name for a while, as that's part of their verification process. If the online verification fails (which happens to about 30% of people), don't panic! You can still call the IP PIN hotline at 800-908-4490, but try calling right when they open at 7 AM EST - that's when you have the best chance of getting through quickly. I got through in about 20 minutes when I called first thing in the morning. The $3,200 refund should still come through fine once you get your PIN and file. The IRS actually processes refunds pretty quickly once they receive a complete return - usually within 21 days. Good luck!

As someone who's made ISO mistakes before, I strongly recommend keeping a spreadsheet with all your grant dates, exercise dates, fair market values, and exercise prices. It's easy to lose track, especially if you have multiple grants or partial exercises. Also, don't forget about state taxes! Everyone focuses on federal, but states have different rules for how they treat ISO dispositions.

This is such a timely discussion! I just went through this exact situation last month. One thing that really helped me was understanding that the "disqualifying disposition" ordinary income treatment only applies to the spread at exercise, not the entire gain. So in your case, Mateo, if you sell now for $42,000 and you paid $12,000 for shares worth $35,000 at exercise, here's what happens: - The $23,000 spread at exercise becomes ordinary income (taxed at your regular income rate) - The additional $7,000 gain ($42,000 - $35,000) is treated as short-term capital gains This is different from a qualifying disposition where the entire $30,000 gain ($42,000 - $12,000) would be long-term capital gains. Also, don't forget you may have already triggered AMT liability when you exercised in March 2024, regardless of whether you sell now or later. That $23,000 spread was an AMT preference item in 2024. The decision really comes down to: pay ordinary income rates on $23,000 now + short-term capital gains on $7,000, versus waiting and potentially paying long-term capital gains rates on the full $30,000 (assuming the stock price holds).

My mom tried one of those big chain tax prep places for her retirement planning and they totally missed some important deductions related to her medical expenses. Cost her hundreds. Just make sure whoever you hire actually specializes in retirement tax issues specifically - not all "tax pros" are created equal!

I made the switch to a tax specialist two years ago when I started dealing with multiple retirement accounts and some stock options from my previous employer. The complexity threshold for me was when I realized I was spending entire weekends researching tax implications instead of just filing my return. My CPA has been worth every penny - she's caught things like optimal timing for Roth conversions based on my income projections, and helped me understand how to coordinate withdrawals from different account types to minimize my overall tax burden. She also set up a multi-year tax strategy that I never would have thought of on my own. The peace of mind is huge too. I sleep better knowing someone who does this full-time is handling the complex stuff, and I can focus on the actual retirement planning rather than worrying about tax mistakes. From your post, it sounds like you're definitely at that complexity threshold. I'd recommend getting a consultation - most good tax pros will give you an initial assessment of your situation and whether their services would be beneficial.

Make sure to also check if you need an ITIN (Individual Taxpayer Identification Number) or EIN (Employer Identification Number) for your business. You'll definitely need one of these to file any US tax forms.

As someone who went through this exact process last year with my international marketplace, I'd strongly recommend getting professional help rather than trying to handle this yourself. The compliance requirements are incredibly complex and change frequently. Beyond what others have mentioned, you'll also need to consider: 1. **Information reporting requirements** - You may need to file Forms 1099-K for US vendors who exceed certain payment thresholds ($600 for 2024) 2. **Backup withholding** - If vendors don't provide proper tax documentation (W-9 forms), you might need to withhold 24% of their payments 3. **State economic nexus laws** - These vary significantly by state and some have very low thresholds (South Dakota is just $100K in sales OR 200 transactions) 4. **Treaty benefits** - Depending on your home country, you might be able to reduce or eliminate certain US tax obligations through tax treaties The penalty structure is also quite severe - states can impose penalties of 25% or more of uncollected taxes, plus interest. For a growing business, getting this wrong upfront can be financially devastating. I'd recommend starting with a comprehensive analysis of your specific situation before making any moves. The investment in proper guidance upfront will save you significantly more in penalties and corrections later.