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.

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.

Thanks for bringing this up! The letter they gave me does say "donation to support school fundraising activities" and doesn't specifically mention raffle or prize. So I'm guessing that's the right wording? Should I request any additional documentation from them before filing?

That wording sounds perfect! It acknowledges your charitable intent while not specifically tying it to the raffle mechanism. You should be good to go with that documentation. I wouldn't request additional paperwork as that might just complicate things. Just make sure you have your receipts showing your costs alongside the donation acknowledgment letter. For business expenses under $250, the documentation requirements aren't as strict, but since your total was $275, having both the letter and receipts provides the complete documentation package you'd need in case of questions.

There's no minimum for business deductions. But honestly for $50, you might spend more time documenting it than it's worth in tax savings. If your tax rate is say 20%, you're talking about saving $10. But if you're already tracking all expenses carefully anyway, might as well include it!

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.

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!

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.

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.

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!

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.