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23 Question for anyone who's dealt with this before - does it matter how long after the death you sell your share? I'm in a similar situation but it's been nearly two years since my mom passed and my brother just now wants to buy my portion of her house. Does that change anything tax-wise?
9 Yes, timing can matter! If you sell soon after inheriting, your basis is the stepped-up value at death and there's usually little to no gain. But if you wait years, any appreciation since death could be taxable. For example, if the property was worth $300K when your mom died (your basis), but is now worth $350K and your brother buys your half for $175K, you'd have a $25K gain ($175K minus $150K basis) that would be taxable. Keep in mind this would be a capital gain, and if you owned it over a year, it would be long-term with better tax rates.
This is really helpful information everyone! I'm dealing with a similar inherited property situation and had no idea about the stepped-up basis concept. One thing I'm curious about though - if multiple siblings inherit a property and one buys out the others like in the original post, does each sibling report their individual sale separately? Or is there some kind of combined reporting required since it's technically one property being transferred within the family? Also, are there any special considerations when the buyer is a family member versus selling to a third party?
Great questions! Each sibling reports their individual sale separately - there's no combined reporting needed. You'll each get your own 1099-S showing what you received for your share, and you'll each report that individually on your own tax returns using Form 8949 and Schedule D. The fact that your brother is buying you out (family member) versus selling to a third party doesn't really change the tax treatment. What matters is that you're disposing of your ownership interest in the property. The IRS treats it as a sale regardless of who the buyer is. One thing to keep in mind though - make sure the sale price is reasonable/fair market value. If you sell to a family member for significantly less than what it's worth, the IRS could potentially question whether it's a legitimate sale or a disguised gift. But as long as you're getting fair value for your share (like getting it appraised first), you should be fine. The stepped-up basis still applies the same way - your basis is the fair market value of your portion at the time of death, not what your father originally paid for the house.
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Does anyone know if a SEP IRA has the same first-time homebuyer exception as a regular IRA? I'm in a similar situation with my SEP and might need to take some money out for a down payment. Trying to avoid that 10% penalty if possible!
Yes, SEP IRAs do qualify for the first-time homebuyer exception, up to $10,000 lifetime limit. You'll still pay income tax on the withdrawal, but no 10% penalty. Just make sure you haven't owned a home in the last 2 years to qualify as a "first-time" buyer by IRS standards.
Thanks for confirming! That's a relief to hear. I haven't owned property in about 5 years so I should qualify under the 2-year rule. Will definitely still have to pay income tax on the withdrawal, but avoiding that 10% penalty makes a huge difference when you're talking about a substantial down payment.
I've been following this thread and wanted to share my experience since I was in almost the exact same boat as Carmen. I had a SEP IRA from my consulting business and kept contributing after I went back to regular employment, thinking I was being smart by continuing to save for retirement. The key thing I learned (the hard way) is that SEP IRA contributions are ALWAYS considered pre-tax, regardless of what account you fund them from. When I was contributing from my personal checking account, I should have been taking those deductions on my tax return - I basically gave the government free money for two years before I figured this out. Here's what I wish someone had told me earlier: if you've been making SEP contributions without taking the deductions, you can file amended returns to get those taxes back. I was able to go back 3 years and recovered about $2,800 in overpaid taxes. The forms you need are 1040X for each year. Also, regarding withdrawals - unfortunately there's no way to separate "pre-tax" vs "post-tax" money in a SEP IRA because technically it's all pre-tax. Any withdrawal will be taxable income plus the 10% penalty if you're under 59½ (unless you qualify for an exception like the homebuyer one mentioned above). My advice: keep the money in the retirement account if you can, and definitely look into filing amended returns if you missed those deductions!
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Has anyone here used a "blocker corporation" structure before conversion to help with the QSBS qualification? Our lawyers suggested this approach since we have some passive income that might otherwise disqualify us from the "active business" requirement.
We actually did this! Created a holding company structure where potentially disqualifying assets were placed in a separate entity. Make sure you're working with someone who really understands the "active business" requirements though, because it's not just about separating assets but about their purpose and use. Our tax attorney specifically helped design a structure that would stand up to scrutiny.
This is such a timely question! I just went through this exact conversion process 6 months ago. One critical thing to add to the excellent advice already given - make sure you get a proper 409A valuation done right at the time of conversion, before any VC discussions get serious. The 409A valuation will establish the fair market value of your shares at conversion, which becomes crucial for both your tax basis and future QSBS qualification. We made the mistake of waiting until after we had a term sheet, and the valuation came back much higher than expected because the appraiser factored in the "investment readiness" of the company. This actually worked against us for the $50M gross assets test. Also, don't forget about potential state-level benefits. Some states like California don't recognize federal QSBS treatment, but others have their own versions or conform to federal rules. Worth checking what your state's position is before you commit to the conversion timeline. The 5-year holding period mentioned by Liam is absolutely critical to remember - I've seen founders get surprised by this when planning their exit strategies. Plan accordingly!
This is incredibly helpful timing advice! I'm curious about the 409A valuation - when you say the appraiser factored in "investment readiness," what specific factors drove the higher valuation? Was it things like having a clean cap table, audited financials, or the fact that you already had investor interest? Trying to understand if there's a way to time this to avoid that premium while still getting an accurate baseline valuation for the conversion.
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The IRS NEVER asks for power of attorney FOR THEMSELVES!! This is almost certainly a SCAM. The IRS doesn't work this way. They might ask you to get representation through Form 2848 but they don't ask for power over your affairs!!
I think the OP is just confused about terminology. They probably received a Form 2848 and misunderstood what it's for. It happens all the time with tax stuff - the language is confusing.
@Diego, I understand your confusion - the terminology around tax forms can be really misleading! Based on what you're describing, this is almost certainly Form 2848 (Power of Attorney and Declaration of Representative), which is NOT you giving power to the IRS, but rather you designating someone to represent YOU when dealing with the IRS. This is actually a protective measure for taxpayers. When tax disputes get complex, the IRS often recommends (or requires) that you have professional representation - like a CPA, enrolled agent, or tax attorney. Form 2848 authorizes that professional to speak with the IRS on your behalf, access your tax records for the specific years/issues you designate, and handle correspondence about your case. You maintain full control - you choose who represents you, you can limit what they're authorized to do, and you can revoke their authority at any time with Form 2848-R. The IRS isn't asking for control over your affairs; they're asking you to get proper representation to help resolve your dispute more efficiently. Before signing anything, make sure you understand exactly which form they want and what it's for. If you're still unsure, consider calling the IRS directly or consulting with a tax professional who can review the specific documentation they sent you.
This is really helpful clarification! I had no idea there was a difference between giving the IRS power of attorney versus designating someone to represent you TO the IRS. The terminology is so confusing - when I first heard "power of attorney" I immediately thought it meant giving up control of my finances or something scary like that. @Reina, do you know if there are any red flags to watch out for when choosing a tax representative? Like qualifications they should have or questions I should ask before authorizing someone on Form 2848?
Maya Lewis
I think everyone's overlooking that the student loan forgiveness is only 2 years away. If I were in your shoes, I'd probly just focus on that short term goal. 2 years of missing Roth contributions isnt gonna destroy your retirement. Have you ran the actual numbers? $1100/month savings on student loans for 24 months = $26,400 saved. That's WAY more than 2 years of max Roth contributions ($6k x 2 = $12k). Just sayin, might be worth taking the hit on retirement contributions to get that sweet loan forgiveness.
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Isaac Wright
•That's a good point, but don't forget about the lost growth on those Roth contributions over time. $12k invested for 25 years at 7% is around $65k. Still might be worth it for the loan forgiveness, but the opportunity cost is higher than just the contribution amount.
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Ethan Brown
This is such a common dilemma for married couples with student loans! I went through the exact same situation a few years ago. Here's what I learned from my research and experience: The $10k income limit for Roth IRA contributions when married filing separately is brutal, but there are definitely workarounds worth considering: 1. **Backdoor Roth IRA** - As mentioned by others, this is probably your best bet. You contribute to a traditional IRA (non-deductible) and immediately convert to Roth. No income limits on conversions. 2. **Maximize your employer 401k** - This isn't affected by filing status, and many plans now offer Roth 401k options too. 3. **HSA if available** - Triple tax advantage and can be used as retirement account after age 65. For the student loan piece - definitely run the numbers on the total savings vs. opportunity cost. But honestly, with only 2 years left until forgiveness and $1,100/month savings, that's probably the financially smart move short-term. One thing to consider: can you and your wife adjust withholdings or estimated payments to get closer to that $10k threshold for next year? Sometimes small tweaks to pre-tax contributions can help you stay under limits while still optimizing the overall strategy. The Solo 401k suggestion is brilliant if you have any 1099 income!
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Sergio Neal
•This is really helpful advice! I'm in a similar boat but hadn't thought about adjusting withholdings to get closer to the $10k threshold. How exactly would that work? Like, if I'm at $139k income, would increasing my 401k contributions enough to get my AGI down to $10k actually be feasible? That seems like it would require contributing almost all of my income, which doesn't sound realistic. Or am I misunderstanding how the income calculation works for the Roth IRA limits?
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