Thanks for the suggestion! Do you know if bank-to-bank transfers also fall under this $600 reporting threshold, or is that just for payment apps?

Bank-to-bank transfers don't fall under the same $600 reporting requirements that apply to payment apps. Those rules specifically target third-party payment networks like PayPal, Venmo, etc. Regular transfers between bank accounts aren't subject to 1099-K reporting regardless of the amount. This is why some people prefer setting up direct transfers for recurring payments like rent or mortgage sharing. It's more straightforward from a tax perspective since there's no confusion about whether it's a business or personal transaction.

That's called "structuring" and it's actually illegal if you're doing it specifically to avoid reporting requirements. Not worth the risk just to avoid something that isn't even taxable in the first place.

Thanks for the info! Definitely don't want to do anything sketchy. Seems like the simplest approach is just to properly mark the payments as personal and not worry about it.

My employer actually did give me a letter saying the move was required for the position! Would that help with any other deductions you know about? And do you think there's any chance they'll bring back the moving expense deduction in time for this tax season?

The letter from your employer could potentially help if any of your expenses could be categorized as unreimbursed employee business expenses. Unfortunately, for most people, these aren't directly deductible either since 2018, but there are exceptions for certain qualified performing artists, fee-basis state or local government officials, and armed forces reservists. As for bringing back the moving expense deduction, it won't happen for this tax season. The Tax Cuts and Jobs Act provisions that eliminated this deduction are in effect through 2025. Any changes would likely come after that, when Congress reviews the expiring provisions. So definitely keep your documentation, but don't expect to use Form 3853 as a non-military taxpayer for at least a few more years.

I second the FreeTaxUSA recommendation! Been using them for years after getting fed up with TurboTax's constant upselling. Much clearer explanations about which forms you can and can't use. They won't be able to magically make Form 3853 available to non-military folks, but at least they'll explain WHY in plain English.

That donation approach sounds super sketchy and likely illegal if audited. The IRS specifically looks for these kinds of arrangements. If you make a donation with the understanding that your child receives a direct benefit (like reduced tuition), it's not a legitimate charitable donation for tax purposes.

I didn't even realize there was a worksheet! I'll definitely look into that option. And yeah, the new form looks completely different from what I remember filing years ago - the elimination of allowances really threw me off. Thanks for the pointer about the worksheet!

Happy to help! The worksheet is actually on page 3 of the W4 form PDF from the IRS website. It's pretty user-friendly for simple situations like yours. Just be sure you're using the 2025 version of the form since they adjust the numbers slightly each year. Another tip: after you submit your W4, check your first couple of paystubs carefully to make sure the withholding looks reasonable. If it seems way off, you can always submit a new W4 to adjust. Most payroll systems let you update it anytime.

That's actually not how the new W4 works anymore. There's no place to put "0" since they eliminated allowances in 2020. The form is completely different now. You'd need to add an additional amount to be withheld on line 4(c) if you want extra withholding.

How much should I expect to pay for a good startup-focused accountant? The quotes I'm getting seem all over the place, from $400 to $3000+ for personal tax prep. Is the higher price worth it?

The price range definitely varies based on complexity and location. If you have multiple equity events, secondary sales, or multi-state filing requirements, expect to be on the higher end of that range. In my experience, paying more for someone with startup expertise has saved me far more than the difference in preparation fees. For context, I paid about $800 for a general CPA my first year, who missed several startup-specific deductions. The next year I paid $2200 for a startup-specialized accountant who saved me over $15,000 through proper equity planning and startup-specific tax strategies. Look at it as an investment - the right accountant should identify tax savings that exceed their fee difference.

Omg please dont. I tried using TurboTax last year for my startup situation and it was a COMPLETE disaster. The software kept getting confused by my 83(b) election and couldn't properly handle the reporting of my partial stock sale. Ended up having to hire a professional anyway to fix all the mistakes and file an amended return. Cost me way more in the end.