Thanks for pointing that out! I just checked the 1099-NEC amount against my records and you're right - there's a discrepancy. The 1099 shows about $650 less than what I calculated based on the monthly benefits. Should I contact them about this or just report the amount on the form?

You should definitely contact the non-profit about the discrepancy. They may need to issue a corrected 1099-NEC. It's better to address this now than have mismatched information when the IRS compares your return with what the organization reported. If they insist the amount on the 1099-NEC is correct, ask them to explain the difference. Perhaps some payments were classified differently or there was a month when payments weren't made. Get it in writing if possible.

Do you know if there's a minimum amount you need to make for the QBI deduction? I only made about $4,000 on a 1099-NEC last year and wondering if it's worth claiming.

Thanks for the suggestions! I do max out my 401k already, but I hadn't thought about an HSA. My employer offers a high-deductible health plan option - would that automatically qualify me for an HSA?

Yes, if your employer offers a qualified high-deductible health plan (HDHP), that would generally make you eligible for an HSA. For 2025, you can contribute up to $4,150 for individual coverage or $8,300 for family coverage, plus an extra $1,000 if you're 55 or older. The beauty of HSAs is the triple tax advantage - tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. Unlike FSAs, the money rolls over year to year, and you can even invest it for long-term growth. Many people don't realize you can use it as a stealth retirement account by saving receipts for medical expenses now and reimbursing yourself years later.

Isn't there also something about investment property loans being tax-advantaged? My cousin claims he deducts all his mortgage interest on his rental properties.

Would a cashless exercise eliminate the possibility of qualifying for long-term capital gains treatment? I'm trying to understand if there's any way to both solve the cash flow problem AND get the better tax treatment.

A standard cashless exercise would indeed eliminate the possibility of getting long-term capital gains treatment because you're selling the shares immediately upon exercise. The entire spread between your strike price and the selling price would be taxed as ordinary income. If you're looking to both solve cash flow issues and potentially get better tax treatment, some companies offer what's called a "partial cashless exercise" where you sell just enough shares to cover your costs and taxes, then hold the rest. Those remaining shares could potentially qualify for long-term capital gains treatment if you hold them long enough.

In my experience working at 3 different startups, the type of option is rarely negotiable. Companies typically have a standard equity plan that applies to everyone at similar levels. NSOs are often used for consultants or non-employees, while employees get ISOs. The tax advantages of ISOs are specifically designed for employees.

Do you know if there are specific forms we need to use for reporting crypto specifically? Or is it just the normal capital gains reporting forms?

For cryptocurrency transactions, you'll use the same forms as other capital assets - primarily Form 8949 (Sales and Other Dispositions of Capital Assets) and Schedule D (Capital Gains and Losses). There's no special crypto-specific form. On Form 8949, you'll need to list each transaction separately with description, date acquired, date sold, proceeds, cost basis, and gain/loss. Then the totals carry over to Schedule D. Make sure to check the correct box at the top of Form 8949 depending on whether the exchange provided you with a 1099-B and whether the basis was reported to the IRS.

I had a $15k loss in 2023 and carried it forward. You'll use Schedule D and it will calculate how much you can use in the current year (up to $3k against ordinary income if you have no capital gains to offset). The remaining amount carries forward automatically and you'll need to keep track of it for future years. Your tax software should handle the calculations, but keep your previous returns handy since you'll need to know how much loss you're carrying forward each year. Mine took about 5 tax years to fully utilize.

Thanks for sharing your experience! Did you have to file any special forms when you did your taxes to show that you'd corrected the excess contribution? And did Fidelity calculate the earnings for you or did you have to figure that out yourself?

Yes, I had to report the correction on my tax return. Fidelity calculated the earnings for me (it was only about $215 since I caught it pretty quickly). They sent me a 1099-R form showing the distribution coded as "return of excess contributions" which I reported on my taxes. I also had to file Form 8606 to report the non-deductible IRA contribution and conversion. On that form, I only reported the allowable contribution amount ($6,000), not the full amount I originally put in. My tax software (I used TaxAct) had a specific section for handling excess contribution removals, which made the process pretty straightforward once I had the documents from Fidelity.

This is actually incorrect advice that could cause problems. You cannot pre-contribute to an IRA for a future tax year before January 1st of that year. While you can contribute to the previous year until the tax filing deadline, you cannot contribute to a future year early. The only option here is to remove the excess contribution (plus earnings) or face the 6% penalty that applies each year until the excess is removed.