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Don't forget the HOLDING PERIOD issue!! Everyone's talking about the exercise tax hit, but there's also huge tax implications for how long you hold the shares AFTER exercising. If you exercise now and hold for >1 year after IPO before selling, any gains ABOVE the FMV at exercise would be long-term capital gains (15-20% tax). If you exercise at IPO and immediately sell, it's ALL ordinary income (up to 37% federal + state + FICA). This was a game-changer for me - exercised my NSOs 14 months before our IPO, paid taxes on a smaller spread, then got LTCG treatment on the massive post-IPO appreciation.
This is absolutely correct. I made the mistake of exercising right at our IPO and selling within the year. Ended up paying nearly 45% (combined federal, state, local) in taxes on the full value. A colleague who exercised a year earlier paid ordinary income on the smaller pre-IPO spread, then only 15% on the huge jump from exercise to IPO price. Difference was over $100k in taxes on roughly similar option grants.
Something I learned the hard way: that 409(a) valuation of $10.50 isn't guaranteed to stay static until IPO! Our company had THREE valuation increases in the 9 months before IPO, with the final one being almost 70% of the eventual IPO price. If your company is gaining momentum toward IPO, the 409(a) valuation will likely increase in the coming months, potentially eliminating some of the tax advantage of exercising early. Maybe consider a partial exercise now to lock in the current valuation for some of your shares? Also, do you know if your company will offer a cashless exercise option at IPO? That's important for your cash flow planning.
That's a really important point about the 409(a) potentially increasing! I hadn't considered that but it makes total sense as we get closer to IPO. I like the idea of a partial exercise strategy. Regarding cashless exercise - I've heard rumors that we'll have that option at IPO, but nothing confirmed in writing. I should probably ask our finance team about this. Would that essentially mean I could exercise and immediately sell enough shares to cover the exercise cost and taxes?
Exactly - a cashless exercise at IPO would let you exercise options and immediately sell enough shares to cover both the exercise cost and the resulting tax bill, without needing to come up with cash out of pocket. Very common for IPOs. If that's an option, you might want to hold some options for that route, especially if you're cash-constrained. The tax hit will be higher, but you won't need liquidity. Many people do a mixed approach - exercise some now for tax advantages (if you have the cash), and save some for cashless exercise at IPO to diversify risk. Definitely get confirmation from your finance team though - some companies require you to exercise before IPO to participate in the offering!
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Let me add something that nobody has mentioned yet - make sure you're filling out Part IV of Schedule C where you answer questions about material participation and whether you started or acquired this business during the tax year. Many people skip this section, but it's crucial for establishing that this was a legitimate business activity, especially when you're showing losses. Also, consider adding a statement to your return that explains your business plan and why you reasonably anticipated making a profit eventually. This proactive documentation can help if questions come up later.
Would you recommend attaching some kind of profit projection or business plan to my return? I did have one when I started, showing how I planned to monetize once I hit certain view thresholds. Just wasn't sure if that would help or draw more attention to the loss.
I wouldn't attach the full business plan to your return as that might actually draw unnecessary attention. Instead, keep it with your tax records in case of an audit. What can be helpful is a brief statement with your return explaining the nature of your business, that you operated with an intent to profit, and mentioning that you have documentation of your business plan and efforts. This shows you're aware of the requirements without overwhelming the initial filing with extra documents.
Has anyone mentioned the potential impact on your Social Security earnings? If you're offsetting your W2 income with Schedule C losses, it could reduce your Social Security wages and potentially lower your future benefits. Something to consider when claiming significant business losses against high W2 income.
This is actually a common misconception. Schedule C losses don't reduce your Social Security wages from W2 employment. Your W2 income is still fully reported for Social Security purposes regardless of Schedule C losses. The losses might reduce your overall income tax, but your Social Security contributions and credits remain based on your W2 earnings.
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Honestly, most people are wasting money at places like H&R Block. I've used TaxSlayer for the last 3 years and it's been way cheaper (around $60 total for federal and state) and super easy to use. Has all the same features as TurboTax but without the higher price tag. Unless you have a really complicated situation (like owning a business, multiple rental properties, or complicated investments), the tax software options are more than enough. The people at those tax prep places are usually just entering your info into similar software anyway, but charging you $200+ for the privilege!
Do you know if TaxSlayer handles crypto transactions well? I did some trading last year and heard that can be a nightmare to report correctly.
TaxSlayer does handle crypto transactions, but I found it to be somewhat limited for more complex crypto situations. It works well if you have straightforward trades from major exchanges that provide good documentation. If you have extensive crypto activity across multiple platforms or DeFi transactions, you might want to use specialized crypto tax software first (like CoinTracker or Koinly) to generate the necessary forms, then import those into TaxSlayer. That's what I did this year after struggling with manual entry last year, and it was much easier.
Spent 15 years as a tax preparer and here's my honest take: the best tax accountants are local CPAs or EAs (Enrolled Agents) who specialize in your specific situation. BUT they're expensive ($350-600 typically). For most people with W-2s and simple investments, TurboTax, TaxAct, or FreeTaxUSA are perfectly fine and will save you hundreds. The big chains like H&R Block often employ seasonal workers with just basic training—you're paying premium prices for entry-level knowledge. One trick: if your adjusted gross income is under $73,000, you can use the IRS Free File program partners to file federal taxes completely free. Many states have similar programs.
This is super helpful! Is there any way to know if I qualify for free file without going through the whole process first? I'm right on the edge income-wise.
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Quick tip from someone who does this regularly - if your income is genuinely below all thresholds, you might not even need to file a self assessment next year. You can call HMRC and ask to be taken out of self assessment if you no longer meet the criteria. Common reasons people stay in self assessment unnecessarily: - They had a one-off income spike - They started self-employment but then stopped - They previously had multiple income sources but now just have PAYE Just something to consider if your situation has changed permanently.
That's really helpful, thank you! My situation was exactly that - I had a side business that generated decent income in 2020-2021, but I closed it down last year. Would I just call HMRC after filing my 2021-2022 return to ask to be removed from self assessment?
Yes, that's right! Complete your 2021-2022 return first (which will show your income is below thresholds), then call HMRC and explain that you've closed your business and no longer need to be in the self assessment system. They'll ask a few questions to confirm you don't meet any of the criteria, and if they agree, they'll remove you from the system. Make sure you keep the confirmation they send you about this. Most people find it's a huge relief not having to worry about the annual self assessment deadline anymore!
Just to add to what others have said - be careful with the timing. If you reduce your payment on account and later your actual income turns out to be higher than you estimated, HMRC will charge interest on the underpayment. Not trying to scare you - if your income is genuinely below thresholds then you're fine! But I made a mistake once where I forgot about some dividend income that pushed me over the threshold, and ended up paying interest.
Yeah this happened to me too. The interest rates aren't massive but it's still annoying. Better to be slightly conservative with your estimate if you're not 100% sure.
Amara Okafor
10 Does anyone know if this affects backdoor Roth IRA contributions? I'm planning to do one this year since I'm over the income limit, but now I'm worried about calculating the basis correctly.
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Amara Okafor
•3 Yes, this is related but slightly different. With backdoor Roth, you make a non-deductible Traditional IRA contribution first, then convert it to a Roth. You'll need to file Form 8606 to report the non-deductible contribution. For basis calculation: your basis in the Traditional IRA is what you've contributed after-tax (non-deductible contributions). When you convert to Roth, you'll pay taxes on any earnings plus any pre-tax money in ANY Traditional IRA accounts you have (pro-rata rule).
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Amara Okafor
•10 Thanks! I didn't realize I needed to file Form 8606 for the backdoor Roth. And I completely forgot about the pro-rata rule. I have an old Traditional IRA from a 401k rollover that would definitely complicate things.
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Amara Okafor
22 Just wanted to share what I learned handling a similar situation with Fidelity last year. If you call Fidelity directly, they can actually recode the distribution as a "return of excess contributions" which gives you the proper coding on your 1099-R for next year. Too late for 2023 obviously, but might help someone in the future!
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Amara Okafor
•1 That's really helpful to know! I wonder if I can still call Fidelity now about my 2023 distribution and have them update the coding retroactively? Has anyone tried this?
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