I thought 83(b) elections were only for restricted stock, not stock options? Can you explain how that would work in my ISO situation?

You're absolutely right, and I should have been more precise. 83(b) elections apply to restricted stock awards (RSAs) or early exercises of unvested options, not standard ISO exercises as in your situation. For your situation with vested ISOs at a now-public company, you're dealing with the standard ISO tax rules that others have mentioned. Your main considerations are the timing of exercise relative to AMT implications and holding periods for qualifying dispositions. Apologies for the confusion.

Good catch! Calculation errors on tax forms are a major audit flag. I learned this the hard way with my own ISO exercise last year.

This sounds interesting but a bit complex. Do you need a specialized attorney to set this up? And does it actually reduce your current tax liability significantly or is it more of a long-term strategy?

You definitely need a team including a tax attorney who specializes in charitable planning and an accountant familiar with these structures. The tax benefits are both immediate and long-term. The immediate benefit is a current year tax deduction based on the present value of the future gift to charity, which can be substantial depending on how you structure it. For example, when I placed $500k of appreciated assets into my CRUT, I received a deduction of about $175k in the year I established it, which directly reduced my current tax liability.

I second the S-Corp recommendation! My accountant also had me set a reasonable salary at about 40% of my business income with the rest as distributions. Huge savings on SE tax. Talk to a good CPA about whether that might work for your specific business type.

I run a specialized software development firm focusing on financial services. Currently structured as an LLC taxed as a sole proprietorship. I've heard about the S-Corp strategy but wasn't sure if the administrative overhead was worth it. Sounds like the savings could be substantial though if you're saving $30k just on self-employment taxes. Do you find the added complexity with payroll and additional filings to be a major headache? And did you have to justify your salary-to-distribution ratio to the IRS at all?

That's a really good point about implementation costs for small businesses. Do you think a phased approach would work better? Maybe start with only high-value goods over $10,000 as they suggest for the pilot, then gradually expand if the systems prove manageable?

A phased approach would definitely make more sense. Starting with high-value goods creates a more manageable testing ground since there are fewer transactions to track and the tax revenue per transaction justifies the administrative effort. I think they'd also need to provide free compliance software for small businesses below a certain revenue threshold. South Dakota v. Wayfair actually mentioned the availability of affordable compliance software as one justification for allowing states to impose collection obligations on remote sellers. The same principle should apply here - if compliance is too burdensome, it could face legal challenges.

Good points about imports. I work for a company that imports about 70% of our inventory from overseas, then distributes nationally. Under this system, would we be considered the "producer" state since we're the importer/distributor? Or would all imported goods follow a different rule? Without clarity on this, it seems like there'd be a massive loophole.

Does contributing to a 401k automatically reduce withholding or do I need to put that on my W-4 somewhere? My HR person was useless when I asked.

401k contributions automatically reduce your withholding because they reduce your taxable income before taxes are calculated on your paycheck. You don't need to put this on your W-4 specifically. However, if you have other deductions like mortgage interest, charitable giving, or student loan interest that aren't reflected in your paycheck, you can estimate their annual total and put that amount on line 4(b) of your W-4 to reduce withholding further.

I tried both and they were ok but seemed to be pushing their paid services. The IRS withholding calculator is completely free and actually pretty good if your tax situation is straightforward. Doesn't work well with irregular income tho.

Creating an IRS account is a nightmare though. I tried to do this last year and they wanted me to verify my identity by entering information from a mortgage, car loan, or credit card - none of which I had at the time! Ended up having to mail in a form and wait 10 days for a verification code.

That's a good point about the verification process. It can be difficult for some people to create an account. If you can't access your transcript online, calling the IRS transcript request line at 800-908-9946 is another option. They can mail your transcript to your address on record. The most important thing is confirming whether an extension or return has actually been filed under your SSN before worrying about potential identity theft or duplicate payments. This information can help determine your next steps.

I tried to pay about $2,700 which was what TurboTax estimated I would owe based on the information I entered so far. I understand extensions only give more time to file, not pay - that's why I attempted to submit the payment with my extension request. I'm just worried about where that money went since the extension was rejected!

This is such an important point that people miss! I've seen so many friends get hit with penalties because they thought filing an extension meant they didn't have to pay until October. The interest and penalties on unpaid tax can add up fast - I think it's something like 0.5% per month plus interest.