Do I need to report my side gig income if I never got a 1099-K from payment apps?

Wait, so even if I only make like $500 selling random stuff online, I'm supposed to report that? What if it's just stuff from around my house - like I'm not really running a business, just clearing out my closet?

The distinction between occasional personal sales and a business is important. If you're just selling personal items from around your house for less than you originally paid (like old clothes or furniture), that's generally not considered taxable income since you're selling at a loss. But if you're making or buying items specifically to resell them, creating products, or regularly selling things for profit, that's considered business income and needs to be reported regardless of whether you get a 1099-K. The IRS looks at factors like regularity, intent to make profit, and whether you depend on the income to determine if it's a business.

Does it work for crypto income too? I've been mining a little on the side and have no idea how to report that stuff correctly.

How does it compare to TurboTax or H&R Block? I'm always skeptical of these new tax tools because I've been burned before by services that miss things and then I end up owing penalties.

It definitely works for crypto income! It has specific features for mining, trading, and staking. You can upload your exchange statements or API access and it'll categorize everything correctly. It's especially helpful with figuring out your cost basis which is always the trickiest part with crypto. As for comparing to TurboTax or H&R Block, the main difference is taxr.ai focuses specifically on analyzing documents and finding things that might be missed. I still use TurboTax for the actual filing, but I run everything through taxr.ai first because it catches things TurboTax doesn't ask about. It's more like having an expert review your situation before you file.

How does that even work? The IRS phone lines are impossible to get through on. Is this some kind of special access thing?

Yeah right. Nothing gets you through to the IRS faster. This sounds like a scam to get your personal info or something. The IRS phone system is designed to be impenetrable.

It's not special access - they've just figured out the optimal times to call and have a system that continuously redials and navigates the phone tree for you. When they get through to a real person, they call you and connect you. It's basically doing what you would do if you had infinite patience and time to keep redialing. I was super skeptical too! I honestly thought it sounded too good to be true. But I was desperate after trying for days to get through myself. The way it works is they don't ask for any tax info - you don't share any personal details with them, just your phone number. When they get through to the IRS, you're the one who talks directly to the agent, so there's no security risk.

What kind of spreadsheet do you use? I'm trying to get organized for next year and have no idea where to start tracking all this stuff.

I use a pretty simple Excel spreadsheet with different tabs. The main tab has columns for Date, Item Sold, Amount, Payment Method, and Fees. I have another tab for expenses broken down by categories like Materials, Shipping Supplies, Marketing, etc. I also take screenshots of my payment app summaries at the end of each month as backup. The key is to update it regularly - I do it every Sunday night so it never becomes overwhelming. Some people use apps like QuickBooks Self-Employed, but honestly for a small side hustle, a simple spreadsheet works fine as long as you're consistent with it.

That's terrible advice. The IRS has a 3-year window to audit returns (and longer in some cases), so "nothing happened" YET. They're also dramatically increasing enforcement for small businesses with the new funding they received. Not worth the risk for what would probably be a few hundred in taxes.