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How to determine adjusted basis for non-qualified ESPP with 20% stock match? Tax implications?

My husband participates in a non-qualified ESPP plan at his company where he gets a 20% stock match whenever he purchases shares (at the same price per share). I've been reviewing the Settlement Information documents which show the cost basis for these shares, but I'm confused about how or if the cost basis needs to be adjusted for tax purposes. From what I understand, tax is only paid on the matched shares, so I don't need to adjust the cost basis for the unmatched shares he actually purchased. Is this understanding correct? I know the adjusted basis should be compensation income plus the acquisition cost. For the matched shares, the value when they were given to him is the compensation income, but what would be considered the "acquisition cost" since he didn't actually purchase these matched shares? Do I only need to worry about the Fair Market Value when the matched shares were granted? Or do I just subtract the FMV from the proceeds to get the adjusted basis? There aren't any fees listed with these shares. Looking at the Supplemental Form, I notice the cost basis is slightly higher than the purchase price, and gain/loss is reported too. Since these were losses (some short-term and some long-term), I'm assuming there wasn't any taxation. Can I just enter them without adjusting, or do I still need to adjust them as mentioned above? And if there were gains instead of losses, how would I calculate the adjusted basis in that scenario? Nothing about these shares appears on his W-2. Thank you for any help!

Don't forget to check if your husband's company provided a Form 3922 for the ESPP purchases. This form provides the information needed to calculate your basis and holding periods. For the matched shares, some companies treat them as RSUs rather than part of the ESPP program, which might explain why they're handled differently. In my experience, the key is determining if tax was already withheld when the matched shares were granted. Check his paystubs from around the grant dates - sometimes the income and withholding for stock compensation appears there but is aggregated differently on the W-2.

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Lilah Brooks

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I'll definitely look for Form 3922! And good point about checking his paystubs - I hadn't thought to look there. Is there any specific section on the paystub where stock compensation typically appears? Also, if the matched shares are treated as RSUs, would that change how we calculate the basis?

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Stock compensation usually appears as a separate line item on paystubs, often labeled something like "Stock Awards" or "Equity Compensation." Sometimes it's under a non-cash benefits section. Look at paystubs from periods immediately following grant dates, as that's when the income would typically be recognized. If the matched shares are treated as RSUs, the tax treatment is actually similar, but the timing might be different. With RSUs, the taxable event occurs at vesting, not at grant. The FMV at vesting becomes your basis, and any subsequent appreciation is capital gain. With matched ESPP shares, the taxable event is usually at grant. The documentation from your husband's company should clarify which approach they're using.

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One thing nobody has mentioned yet - check if your husband's company offers a "Section 83(b) election" for the matched shares. This would allow you to pay tax on the shares at the grant date (based on FMV then) rather than at vesting, which could be advantageous if the shares are expected to appreciate significantly. The deadline for this election is 30 days after receiving the shares though, so it may be too late if he's already had them for a while. Just something to keep in mind for future grants!

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Isaac Wright

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Section 83(b) elections are usually more relevant for restricted stock with vesting conditions, not immediate stock matches in an ESPP. From what OP described, it sounds like the matched shares are granted immediately without vesting requirements, so 83(b) probably wouldn't apply here.

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Oliver Weber

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Something nobody's mentioned yet - if your partner gets any per diem or allowance from the union for these travel expenses, that changes things. My union provides a travel stipend for jobs beyond a certain distance, and that needs to be reported differently on taxes. If they're getting any kind of travel allowance or per diem that isn't included on their W-2, that needs to be handled carefully. Also worth checking if your partner's collective bargaining agreement has any provisions about travel reimbursement they might not be taking advantage of.

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Ava Williams

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They don't currently get any stipend or per diem for the travel unfortunately. That's why we're trying to figure out if there's any tax relief available. The union does have some provisions for travel pay, but only for jobs beyond a certain distance (I think it's 75 miles), and most of their assignments fall just under that threshold. Do you know if there's a standard mileage rate they could use instead of tracking actual gas costs?

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Oliver Weber

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Yes, using the standard mileage rate is usually much easier than tracking actual gas expenses. For 2024, the standard mileage rate for business travel is 67 cents per mile. This covers gas, wear and tear, depreciation, and insurance. If your partner qualifies to deduct these expenses (based on the temporary work location rules others mentioned), using the standard rate is typically much simpler than keeping all gas receipts. Just make sure they keep a detailed log of dates, locations, business purpose, and miles driven. There are several good mileage tracker apps that can help with this too.

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I'm an electrician with similar situation. One important thing - if your partner gets a W-2 (rather than 1099), these deductions got much harder after the 2018 tax law changes. Employee business expenses used to be deductible on Schedule A, but now they're basically eliminated for W-2 workers until 2025 when the law changes again. If they're truly an employee (W-2), they might be out of luck unless their employer is willing to set up an accountable plan to reimburse these expenses tax-free. If they're considered self-employed (getting 1099-NEC), then they can deduct these business expenses on Schedule C.

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This is the correct answer that everyone else missed. The Tax Cuts and Jobs Act suspended miscellaneous itemized deductions subject to the 2% floor from 2018 through 2025. This includes unreimbursed employee business expenses like mileage to job sites. If they're a W-2 employee, these expenses aren't deductible at the federal level right now. Some states still allow these deductions on state returns though, so check your state tax laws!

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I think the Forbes article might have been technically correct but just explained it poorly. The 15.3% is Social Security (12.4%) + Medicare (2.9%). The Social Security part only applies up to the wage base (which changes yearly). The Medicare 2.9% applies to all SE income. The ADDITIONAL 0.9% Medicare tax (which brings it to 3.8% total) kicks in at higher income levels ($200k/$250k). The article maybe just didn't mention this additional tax? Either way, I agree that tax info is confusing. I always double check the IRS website and cross-reference with Publication 15 and Publication 334.

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But that's still wrong - the total isn't 3.8%. The Additional Medicare Tax is 0.9%, which when added to the 2.9% regular Medicare tax equals 3.8%. Is that what you meant?

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Yes, that's exactly what I meant. The base Medicare tax is 2.9% on all SE income. Then the Additional Medicare Tax of 0.9% kicks in at those higher income thresholds, bringing the total Medicare portion to 3.8% (2.9% + 0.9%). I should have been clearer in my wording. Thanks for pointing that out. This conversation perfectly illustrates how even small differences in how tax concepts are explained can lead to confusion!

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Has anyone else noticed that the wage base for Social Security taxes increases every year? In 2023 it was $160,200, up from $147,000 in 2022. For 2025 it's expected to be around $168,600. This is why old articles can be misleading - tax numbers change annually but articles rarely get updated!

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Yara Nassar

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The wage base is tied to the National Average Wage Index so it automatically increases with inflation. It's gone up dramatically in recent years because wages have been rising so quickly. You can always find the current wage base on SSA.gov rather than relying on articles that might be using outdated numbers.

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Thanks for explaining that! I didn't realize it was tied to wage inflation. Makes sense why it's been jumping up so much these past few years. I'll bookmark the SSA site for future reference.

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Yuki Sato

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Just want to add that you should DEFINITELY declare that Venmo income. The IRS is cracking down on payment app reporting. Venmo and other payment services are now required to report business transactions to the IRS if you receive more than $600 in a year. That $9,500 is way over the threshold. Not declaring that income could lead to significant penalties down the road. Plus, you're missing out on legitimate deductions! Your equipment, a portion of your utilities, internet if you use it for scheduling, any training materials - all that can offset the income.

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Carmen Ruiz

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But how does Venmo know which payments are business vs. just friends paying me back for stuff? I use the same account for both.

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Yuki Sato

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Great question. Venmo has been rolling out features to distinguish between personal and business transactions. They now have specific "business" profiles/settings, and the way payments are categorized matters. If people are paying you for goods and services (which they can select when sending money), those will be reported. If it's marked as payments between friends, it's treated differently. However, the IRS doesn't care how Venmo categorizes it - if it's income from services you provide, it's supposed to be reported regardless of how it was processed. The smart approach is to set up a separate Venmo account just for your business transactions to keep everything clean and organized.

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Has anyone actually calculated if it's worth it? Like, what's the actual math on claiming $9,500 in income vs the deductions you'd get for the 400 sq ft space? I'm curious about the real numbers here.

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I did this calculation for my home art studio which is about 350 sq ft. My income was around $11k last year. After deducting my legitimate business expenses (portion of mortgage interest, utilities, supplies, etc.), my taxable business income dropped to about $6,200. That saved me roughly $1,700 in taxes. The key is keeping good records of ALL your expenses. Things people often forget: portion of internet if you use it for business communication, cell phone percentage used for business, mileage driving to get supplies, software subscriptions, insurance, etc. It was definitely worth it for me.

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Have you considered just filing Form 1065 (Partnership Return) manually? If your tax software can't handle the specific ownership percentages, sometimes going old school is the easiest solution. Your LLC with multiple members is treated as a partnership by default for tax purposes anyway. You'll need to prepare Schedule K-1s for each member showing their specific ownership percentage, distributive share of income, deductions, etc. It's not as complicated as it sounds for a simple LLC with just two members.

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StarGazer101

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Honestly I hadn't considered doing it manually since I'm pretty intimidated by all the tax forms. Is Form 1065 something a regular person can figure out without an accounting background? And how would I calculate all the specific numbers for the K-1s?

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Form 1065 is definitely doable without an accounting background, especially for a small, straightforward LLC with just two members. The IRS provides detailed instructions, and there are plenty of free guides online. For the K-1s, you basically take each income and expense item and allocate them according to your ownership percentages. So if your LLC had $10,000 in profits, your wife's K-1 would show $5,100 (51%) and yours would show $4,900 (49%). Same with deductions and credits. The actual form walks you through each line item. The trickiest part is usually just gathering all your business income and expense information, which you'd need to do for any tax preparation method anyway.

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Quick question - are you guys actually operating as an LLC taxed as a partnership? Or did you elect to be taxed as an S-Corp? That makes a huge difference in how you file and which forms you need.

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StarGazer101

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We're just a regular LLC with no special tax elections. When we formed it, we didn't do anything special with the IRS, so I think we're taxed as a partnership by default? Now I'm worried we messed that up too...

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You're good then! You're right that a multi-member LLC is taxed as a partnership by default if you didn't make any special elections. You'll need to file Form 1065 and prepare K-1s for both of you showing the 51/49 split. One more thing to consider - if this is your first year filing, make sure you've obtained an EIN (Employer Identification Number) from the IRS. You'll need this for your partnership return. If you haven't done this yet, you can get one instantly online through the IRS website.

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