Has anyone considered the implications of company acquisition before full vesting? With my previous startup, we were acquired 3 years into my 4-year vesting schedule. My colleagues with ISOs had to scramble to exercise, while those with RSAs just had their vesting accelerated. The tax situations were dramatically different.

This is exactly the kind of complex equity compensation decision that can have huge long-term tax implications. Based on what you've shared, the RSA with 83(b) election route seems compelling given the current low valuation at $12,000. A few additional considerations for your situation: First, make sure you understand your company's vesting acceleration policies in case of acquisition or termination scenarios. Some companies have "double trigger" acceleration that could protect you even if you leave early. Second, consider your personal cash flow - paying 40% tax upfront ($4,800) versus having $12,000 tied up in ISO exercise costs later. One thing I'd strongly recommend is getting clarity on the forfeiture provisions if you do choose RSAs and leave before full vesting. While you can generally claim unvested shares as a capital loss (as others mentioned), the specific mechanics can vary by company and you'll want documentation showing the forfeiture. Given the 30-day deadline for 83(b) elections, you might want to model out a few scenarios quickly. The stories here about AMT hits with ISOs are real - I've seen colleagues get burned badly when company valuations spiked but liquidity never materialized.

I think there's confusion about what "lived with" means for IRS purposes. It doesn't just mean physically under same roof. If spouse is away for school or job but its temporary and you're still financially connected (like paying their rent!!), you're considered living together. I've been through this exact situation. Wife in residency in different state. I paid some of her bills. IRS considers that LIVING TOGETHER for MFS status. Had to remove roth contributions and pay penalty. Really sucked. If you already contributed to Roth and need to file MFS as "lived together" you should look into removing the excess contribution ASAP before you file. Theres a process for it to avoid bigger penalties.

Based on your description, it sounds like you and your husband would likely be considered "living together" for IRS purposes despite having different addresses. The fact that you're helping pay for his student housing and co-signed the lease creates a strong financial connection that the IRS considers when determining living status. The IRS generally views educational separations as temporary, not permanent living apart situations. Since you're financially supporting his housing arrangements, this reinforces that you're maintaining a connected household even though you're physically in different locations. For your Roth IRA situation, this means you'd be subject to the much lower income limits that apply to Married Filing Separately filers who lived together ($10,000 modified AGI phase-out range for 2023). If you've already made contributions above this limit, you'll want to remove the excess contribution before filing to avoid the 6% annual penalty. I'd recommend getting official guidance on your specific situation, either through a tax professional or by contacting the IRS directly, given the financial implications of getting this wrong.

Did anybody mention TSP loans? Since you're working for the federal government now, once you've been contributing to your TSP for a while, you can take loans from it without the tax penalties of an early withdrawal. Interest rates are pretty reasonable too, and you pay the interest to yourself. Might be something to consider for future needs rather than tapping retirement accounts and paying penalties.

Hey Freya! I was in a similar situation a couple years back with an old 403b from a teaching job. One thing I learned that might help - since you're now a federal employee, you might want to consider if you qualify for any of the hardship exceptions that could waive the 10% penalty. Things like unreimbursed medical expenses, higher education costs, or even certain unemployment situations can qualify. Also, don't forget about state taxes! Depending on which state you're in, you could owe anywhere from 0% to 10%+ on top of federal taxes. Some states don't tax retirement distributions at all, while others treat them as regular income. The partial rollover idea mentioned earlier is really smart too - you could roll most of it into your TSP (yes, you can roll a 403b into TSP!) and just take out what you absolutely need in cash. That way you minimize the tax hit while still getting some immediate funds. Just make sure to get everything in writing from your 403b administrator about exactly how much will be withheld and when you'll receive the funds. Some plans can take weeks to process distributions.

I was in the same boat last year and wish someone had told me this - the apps are now reporting this data directly to states! My friend got a notice from Indiana asking why he didn't file a return there, when he had only placed a few bets while driving through the state. The betting apps are required to track your physical location for legal compliance reasons, and that data is increasingly being shared with tax authorities.

This is such a timely question! I just went through this exact situation for my 2024 taxes. I'm registered in Texas but placed winning bets while traveling for work in Nevada, Louisiana, and Arizona. After consulting with a tax professional, here's what I learned: technically, you're supposed to file nonresident returns in each state where you physically placed winning bets, regardless of where you're registered with the app. The key factor is your physical location when the bet was placed, not your registration address. However, the enforcement is still inconsistent. Some states are getting more aggressive about tracking this (especially states with higher tax rates who want their piece), while others haven't caught up yet. The apps do track your location for regulatory compliance, and this data is increasingly being shared with state tax authorities. For your situation, I'd recommend keeping those detailed records you mentioned and filing properly in each state where you had significant winnings (maybe $500+ threshold). You can then claim credits on your Ohio return for taxes paid to other states to avoid double taxation. If we're talking smaller amounts, the risk might be low, but with the trend toward more enforcement, it's probably safer to file correctly from the start. The hobby vs. professional distinction doesn't change the sourcing rules - winnings are still taxable where the activity occurred regardless of how you classify your gambling activities.

Has anyone actually calculated the total difference between employer pretax health insurance vs marketplace plans when considering ALL factors? I'm in similar situation but also wondering about: 1. Quality of network (my employer plan sucks) 2. Premium differences 3. Tax implications 4. Out-of-pocket differences My employer takes $515/month pretax but the deductible is $7000! Marketplace plan is $560/month but deductible only $3500. Trying to figure out total cost including taxes.

One thing to consider that hasn't been mentioned yet is whether your employer offers a Health Savings Account (HSA) option with their high-deductible health plan. If they do, that's another significant tax advantage you'd lose by going to marketplace coverage. HSA contributions are triple tax-advantaged: deductible going in, grow tax-free, and withdrawals for qualified medical expenses are tax-free. For 2025, you can contribute up to $4,300 for individual coverage or $8,550 for family coverage. This could potentially offset some of the higher deductible concerns while maximizing your tax benefits. Also worth checking if your employer contributes anything to an HSA on your behalf - that's essentially free money you'd be giving up. Some employers contribute $500-2000 annually to employee HSAs, which changes the math considerably when comparing total compensation packages. If HSA isn't available with your current plan, that might actually strengthen the case for switching to marketplace coverage, especially if you can find an HSA-eligible high-deductible plan there.