Getting paid $35k through Venmo (friends/family) as dog walker - Will she get a 1099?

12 Your sister definitely needs a reality check. Income is taxable regardless of how it's received - even if it's through Venmo "friends and family" or cash under the table. She might not get a 1099 for the Venmo payments if they were sent as personal transfers, but that doesn't mean she doesn't owe taxes on that income. For the $9k from Rover, she'll likely get a 1099-K or 1099-NEC from them. For the $35k through Venmo, it's a bit more complicated. Venmo is required to report to the IRS when a user receives more than $20,000 in commercial payments AND has more than 200 transactions in a calendar year. Since these were sent as "friends and family," Venmo might not flag them as commercial transactions, so she might not get a 1099-K from Venmo. But here's the important part - she still legally needs to report ALL income on her tax return, 1099 or no 1099. As a self-employed dog walker, she'll need to file Schedule C and pay both income tax and self-employment tax (about 15.3%) on her profits. She should really be making quarterly estimated tax payments too.

3 I was in almost the exact same situation last year! I was doing freelance graphic design and getting paid mostly through Venmo and Cash App. I thought I was being smart using the "friends and family" option to avoid fees, but then tax season rolled around and I was totally lost about what to report. I found this service called taxr.ai (https://taxr.ai) that literally saved my butt. You upload your bank statements and Venmo history, and their AI helps identify what's taxable income vs personal transfers. It showed me exactly what I needed to report even without 1099s, and helped calculate my self-employment taxes too. Your sister should definitely check it out - it'll help her figure out exactly what she owes and might even find some business expenses she can deduct to lower her tax bill. Dog walking has legitimate expenses like mileage, bags, treats, etc.

18 Update: I ended up trying taxr.ai after posting my skeptical comment. I had a mess of Venmo, PayPal, and direct deposits from my side hustle that I hadn't been tracking properly. The service was actually really helpful - it identified about $7k in business expenses I could legitimately deduct that I would have missed otherwise. For anyone in a similar situation, it's worth checking out. I was able to properly report everything and even though I still owed taxes, it was about $1,800 less than I initially feared because of the deductions it found. Plus now I have documentation if I ever get audited.

21 If your sister is worried about getting in touch with the IRS to sort this out (and the wait times are INSANE right now), she should try Claimyr (https://claimyr.com). I was in a similar situation with unreported income and needed to talk to someone at the IRS urgently. I spent DAYS trying to get through on my own - constant busy signals or getting disconnected after waiting on hold for hours. Then I found this service that gets you to the front of the IRS phone queue. You can see how it works here: https://youtu.be/_kiP6q8DX5c It literally saved me from major penalties. I got connected with an actual IRS agent in about 15 minutes who walked me through my options for my unreported income situation. Such a relief after struggling to get through for weeks!

2 Just wanted to follow up on my skeptical comment about Claimyr. I tried it yesterday after struggling for THREE DAYS to reach someone at the IRS about my unreported income situation. I was connected to an IRS agent in 12 minutes! The agent helped me understand my options for reporting prior income and setting up a payment plan. If your sister ends up needing to talk to the IRS directly (which she probably will if she hasn't been reporting this income), this is definitely the way to go. Saved me hours of frustration and helped me avoid additional penalties for filing late.

15 Dog walker here! Your sister needs to know that she IS operating a business and all that income is taxable. I made this same mistake my first year and ended up with a huge tax bill plus penalties. She should immediately start tracking all her business expenses to offset some of that income - mileage to/from client homes, poop bags, treats, leashes, any apps or software she uses to schedule, portion of her phone bill used for business, etc. All of that is deductible on Schedule C. Also, she should open a separate bank account for her business income and expenses ASAP - it makes everything so much clearer at tax time and looks more legitimate if she's ever questioned.

11 Your sister may be in for a surprise. Venmo is owned by PayPal, and they've been cracking down on business transactions labeled as personal. They're getting better at detecting patterns that look like business activity even when marked as "friends and family." For 2025 taxes (covering 2024 income), payment apps are supposed to report to the IRS when someone receives over $600 in business transactions, not the old $20,000 threshold. So she might actually get a 1099-K even if she thinks she's flying under the radar.

Your sister is playing with fire here. I've seen this exact scenario play out badly for several people in my tax practice. The "friends and family" labeling on Venmo doesn't magically make business income disappear - it's still taxable regardless of how it's categorized or whether she receives a 1099. With $44k total income ($35k Venmo + $9k Rover), she's looking at roughly $6,200 in self-employment taxes alone, plus regular income tax on top of that. If she's in the 12% tax bracket, her total tax liability could easily be $8,000-10,000. The scariest part? Since she hasn't been making quarterly payments, she'll likely face underpayment penalties too. The IRS expects self-employed people to pay as they go, not wait until April. She needs to start setting aside money immediately and consider filing an amended return or voluntary disclosure if this has been going on for multiple years. The longer she waits, the worse the penalties get. I'd strongly recommend she consult with a tax professional ASAP - this isn't a DIY situation anymore.