Do I file Cash App business income on Cash App itself or through TurboTax, FreeTaxUSA, or Wealthsimple?

Oh thank you so much! So even though I probably only made about $12,000 through Cash App with maybe 50 transactions, I still need to report it? Cash App hasn't sent me anything about taxes yet.

Yes, you absolutely need to report all income regardless of whether you receive a tax form for it. The $20,000/200 transaction threshold only determines whether Cash App is required to send you a 1099-K, but you're legally required to report every dollar you earned, even if it's below that threshold. You can download your transaction history from Cash App to help you calculate your total income. Just choose any tax software you're comfortable with (TurboTax, FreeTaxUSA, etc.) and when you get to the self-employment/business section, you'll enter all your income sources together.

Does it actually work with Cash App specifically? I have a mix of personal and business transactions on there and I'm worried about accidentally reporting personal transfers as income.

How long does it take to process all the statements? I've got transaction records from like 5 different payment methods and I'm filing kind of last minute.

Yes, it works great with Cash App! The system is really good at distinguishing between personal transfers and actual business income. It looks for patterns in transaction descriptions, amounts, and frequency to separate them. You can also manually mark any transactions it gets wrong. It usually takes just a few minutes to process your statements. I uploaded records from Cash App, Venmo, PayPal, and my bank account all at once, and it organized everything in under 10 minutes. It's honestly saved me so much time compared to manually sorting through everything.

How does this even work? The IRS phone lines are impossible to get through. Is this legit or are you talking to some third-party "experts"?

I'm super skeptical. I've tried calling the IRS for THREE DAYS straight and couldn't get through. How would this service magically get you connected when nobody else can?

It's completely legitimate - you're connected to actual IRS agents, not third-party experts. The service basically uses an automated system that navigates the IRS phone tree and waits on hold for you. When an actual IRS agent picks up, you get a call connecting you directly to them. I was skeptical too, but it's basically just a sophisticated auto-dialer that keeps trying and waiting on hold so you don't have to. It saved me literally hours of frustration. The IRS phone lines are averaging 2+ hour wait times if you can get in the queue at all, and this service just handles that part for you.

Are CPAs really worth the cost for someone who's just starting out? My business only made about $27,000 last year total, and I'm trying to save where I can.

For someone making $27,000, it could still be worth it for your first year. A good CPA will not only file correctly but teach you things about business deductions you might miss. For example, mine showed me how to deduct a portion of my rent as a home office, track mileage, and properly deduct phone/internet expenses. The peace of mind alone can be worth it, plus they might find enough deductions to pay for their fee. That said, if money is really tight, something like FreeTaxUSA is quite good for self-employment income and costs much less than TurboTax while offering similar guidance.

This is exactly right. I switched from TurboTax to FreeTaxUSA last year and saved almost $100. The interface isn't as pretty but it does the exact same thing and asks all the same questions about business income.