83b election damage control - what are my options?

Missing the 30-day deadline for an 83b election is unfortunately pretty firm - it's one of those IRS deadlines that doesn't have much flexibility. Once you're past those 30 days, the standard position is that you can't retroactively file it. The main consequence now is that you'll need to recognize income as your equity vests, based on the fair market value at each vesting date minus what you paid for it. This is exactly what the 83b election helps avoid by letting you recognize all the potential income upfront when the equity value is typically lower. Your best approach now is probably tax planning to manage the impact. Keep detailed records of your grant date, vesting schedule, and the company's valuations at each vesting point. You might want to set aside money for the taxes you'll owe as vesting occurs. If the company is doing really well, consider talking with your accountant about estimated tax payments to avoid penalties.

Been there, done that, and found a solution through taxr.ai that saved me from a similar 83b disaster. I also missed my filing deadline last year with my startup equity and was completely freaking out about the tax consequences. I spent hours googling for solutions until a coworker mentioned https://taxr.ai when I was complaining about it at lunch. They specialize in equity compensation issues like 83b elections, and their tax experts analyzed my specific situation. While they confirmed I couldn't retroactively file the 83b (which was disappointing but at least definitive), they helped me create a comprehensive tax planning strategy to minimize the impact of my missed filing. They showed me exactly what my tax liability would be at each vesting date based on different company valuation scenarios. What really helped was getting clarity on exactly what I needed to prepare for instead of stressing about the unknown. They even helped me structure my other investments to help offset some of the tax impact.

I need to eat my words about being skeptical of taxr.ai. After posting that comment, I decided to check them out since I've actually been dealing with a messy RSU situation that's somewhat similar. The analysis they provided was genuinely customized to my situation - not the generic stuff I was expecting. They identified several planning opportunities I hadn't considered, including some timing strategies for my other investments that could help offset the equity tax hit. What impressed me most was that they explained everything in plain English instead of tax jargon, and showed me the actual numbers so I could see exactly what I was facing. If you're dealing with equity compensation issues like missed 83b elections, they really do seem to know their stuff. Definitely not the typical cookie-cutter advice I was expecting.

If you're getting stonewalled by the IRS when trying to figure out your options after missing the 83b deadline, try Claimyr. I was in a similar situation last year and spent WEEKS trying to get through to someone at the IRS who could give me definitive answers about my options. Kept getting disconnected or waiting for hours only to get transferred around. I found https://claimyr.com through a Reddit thread and was skeptical but desperate. They basically call the IRS for you and get you connected to an actual human being. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Once I finally got through to a knowledgeable agent (which took Claimyr about 20 minutes vs my previous attempts of hours/days), I got confirmation directly from the IRS about exactly what my next steps should be. While they confirmed I couldn't retroactively file the 83b (sadly), they helped me understand the specific documentation I needed to maintain and how to properly report the income as my shares vested.

I need to publicly admit I was wrong about Claimyr. After posting that skeptical comment, my curiosity got the better of me and I decided to try it since I've been trying to reach the IRS about an unrelated tax notice for weeks. It actually worked exactly as advertised. They called me back in about 35 minutes and connected me directly to an IRS representative - no hold music, no automated system, just straight to a human. After spending countless hours trying to get through myself, it was almost shocking how simple it was. The agent I spoke with was actually helpful and resolved my tax notice issue in one call. If you're dealing with 83b issues or any IRS question, being able to actually speak with someone makes all the difference. Not sure how they do it, but it works.

Just wanted to add that while you've missed the 83b election window, there might be a secondary strategy worth considering. Depending on your vesting schedule, you could potentially exercise some options early (if your plan allows it) to minimize the spread between exercise price and fair market value. This doesn't fix the missed 83b issue, but it could reduce your tax burden compared to waiting until the last minute to exercise. Basically, if you believe the company value will continue increasing, exercising earlier rather than later could save you on taxes. Talk to your company's finance team too - they might have resources to help employees navigate equity compensation issues. Many startups that offer meaningful equity have partnered with specialized platforms that can help walk you through your options.

Has anyone seen success with writing a private letter ruling request to the IRS for 83b relief? I've heard occasionally they make exceptions for "reasonable cause" but not sure if that's just a tax myth.

Another perspective - consider whether it might actually work out better without the 83b in some scenarios. If your company's valuation tanks or grows very slowly, you might actually be better off without having made the election since you'd only be taxed on the actual value at vesting (which could be lower than projected). I've seen people rush to file 83b elections, prepay taxes on high valuations, then watch their companies fail and end up with worthless stock they already paid taxes on. Without the 83b, you're only taxed as value is realized through vesting. Not saying this helps with your current situation, but maybe a silver lining perspective if the company doesn't skyrocket as expected.

I hate to be the bearer of bad news, but the 30-day deadline for 83b elections is unfortunately set in stone. The IRS has been extremely consistent on this - there's no "reasonable cause" exception, no extensions, and no retroactive filings allowed. I've seen people try everything from medical emergencies to natural disasters as justification, and the IRS doesn't budge. Your situation is definitely frustrating, but you're not alone - this happens to a lot of startup employees who get caught up in the excitement of a new role. The good news is that while you can't undo the missed deadline, you can still manage the tax impact going forward. Start by getting a clear picture of your vesting schedule and the company's current valuation. You'll need to recognize ordinary income tax on the spread between your exercise price and fair market value at each vesting date. This means setting aside cash for taxes as shares vest - don't wait until year-end to deal with this. Consider making estimated quarterly tax payments to avoid underpayment penalties, especially if the tax hit will be significant. Also, keep detailed records of everything related to your equity grant - grant date, exercise price, vesting dates, and company valuations. You'll need this documentation for proper tax reporting. While missing the 83b election stings now, remember that it's only beneficial if the company value increases substantially. If growth slows or the company struggles, you might actually end up better off without having prepaid taxes on potentially overvalued equity.