That's actually really good advice I hadn't thought about. The site does have a transaction history but I'm not sure how long they keep it. Do you think I should also be documenting the gift card purchases separately? And should I be using the transaction hash from the blockchain as well?

Yes, document the gift card purchases too! Screenshot receipts, confirmation emails, anything showing you bought them. This creates a clear paper trail of the full transaction flow: money → gift cards → gambling site → crypto winnings. The transaction hash from the blockchain is absolutely essential documentation. That's your definitive proof of exactly when you received the ETH and how much. Save that information along with a record of what ETH was trading for at that exact moment. Services like CoinMarketCap let you look up historical prices at specific times. This combination of evidence makes your cost basis virtually indisputable if questions ever come up.

I used FreeTaxUSA last year for something similar. You need to report the gambling winnings separately from the crypto. Under "Income" there's an "Other Income" section where you report gambling winnings. Then under "Investments" you add the crypto with your cost basis being the value when you received it. It's not super intuitive but works fine once you set it up right.

Thanks, that helps a lot! I was trying to do everything under the crypto section which explains why I was getting confused. I'll separate the gambling income like you suggested.

Is there any way to request that schools change how they report this? It seems fundamentally unfair that the reporting method can cause students to lose out on significant tax credits just because of when payments happen to be processed.

Unfortunately, schools don't have much flexibility here. The IRS mandates the reporting methods, and schools must follow them. Prior to 2018, schools could choose between reporting amounts billed or payments received, but now most are required to use the payments received method. What students can do is plan their payments strategically if possible. For example, if you know you're graduating in Spring, sometimes delaying that final tuition payment until January (of your graduation year) can help align the reporting with when you'll receive and use your education. However, this depends on your school's payment deadlines and late fee policies.

I had the same problem with TurboTax! I ended up switching to FreeTaxUSA which let me enter my actual qualified education expenses separate from what was on the 1098-T. You have to include an explanation statement, but at least it allowed me to claim the full credits I was entitled to.

Thanks for the suggestion! I just tried FreeTaxUSA and it definitely gives more flexibility. It asks for what's on the 1098-T but then has separate entries for "actual qualified expenses paid" where you can enter the correct amounts. Much better approach than the other software I tried.

I used FreeTaxUSA Pro last season and it was decent for basic returns. The interface isn't as polished as the big names but it gets the job done. State returns are extra though, like $15 each.

Good point! I wasn't planning to charge anything since I'm just getting experience, but I'll look into getting a PTIN anyway to do things properly.

Careful with the cashless exercise suggestion - that only works if the company is publicly traded or has some kind of secondary market for the shares. Sounds like OP's company is still private with no immediate IPO plans.

Good point about the cashless exercise - I was assuming there might be a secondary market since it's a Series D company, but you're right that it's not guaranteed. Another option to consider is a net exercise if the company allows it. With a net exercise, you surrender some of your options to cover the exercise cost, so you get fewer shares but don't have to put up any cash. Won't help with the tax withholding for NSOs though.

I've had good luck with The Startup CPA (thinkthis.com). Not cheap but they actually understand equity compensation and saved me a ton on AMT planning. Worth the fee considering how much is at stake with these decisions.

Do you know how long the correction process took from start to finish? I'm in a similar situation and trying to figure out if I should expect weeks or months for resolution.

For me it took about 7 weeks total from when the SBA submitted the correction to when I received the refunded money. The first 4 weeks nothing seemed to happen, then suddenly I got a letter from Treasury acknowledging the correction, and 3 weeks after that the money showed up in my account. The SBA agent told me their internal correction process takes 5-10 business days, then it goes to Treasury whose process takes another 30-45 days. So altogether you're looking at around 6-8 weeks if everything goes smoothly.

I asked about this specifically when my offset was finally reversed. Unfortunately, the Treasury representative told me they don't pay interest on offset reversals, even when the offset was done in error. Their rationale is that it's considered an "administrative correction" rather than a penalty or judgment against the government.