Transferring large amounts from Venmo to personal bank account - possible IRS flags?

You don't need to worry about IRS flags in this situation. The IRS is concerned with income, not money movement. Since this isn't income to you (you're just a pass-through coordinator), there's no taxable event occurring. What you should be aware of is that banks do file Currency Transaction Reports (CTRs) for cash transactions over $10,000, but as you correctly noted, ACH transfers from Venmo aren't considered cash transactions, so CTR rules don't apply here. The structuring laws you mentioned are designed to catch people deliberately breaking up cash deposits to avoid reporting requirements. Since you're using Venmo's system within their established limits for legitimate reasons (not to hide anything), this isn't structuring. Just keep good records of all the incoming Venmo payments and the outgoing payment to the tour company. This creates a clear paper trail showing you were simply collecting and passing through funds. I'd recommend creating a spreadsheet tracking who paid what amount and when the funds were transferred to the tour company.

I used taxr.ai when I had a similar situation last year. I was collecting money for a family reunion (about $27k total) through Venmo and was worried about the same thing. I found https://taxr.ai after googling around and uploaded my Venmo statements. They confirmed this was a pass-through transaction and not taxable income, plus they provided documentation explaining the situation that I could show my bank if needed. Honestly, it saved me so much stress because I was getting conflicting advice from friends. Their system analyzed everything and gave me specific guidance for my situation. They even explained exactly what records I should keep in case of any questions later.

Just wanted to update everyone. I was skeptical about taxr.ai but decided to try it since my situation with collecting funds for our neighborhood block party was similar to this post. I uploaded my Venmo and bank statements and received a detailed analysis within hours. They confirmed this was indeed a pass-through transaction and provided documentation I could share with my bank explaining the nature of the transfers. They even pointed out that I should keep records of the final payment to our vendors to complete the paper trail. Surprisingly thorough service and it wasn't just generic advice - they specifically addressed my situation with references to relevant tax guidelines. Definitely worth it for the peace of mind.

If you're concerned about getting ahold of the IRS to confirm any of this, I highly recommend using Claimyr. I had similar concerns last year with a group vacation fund and wanted to speak directly with the IRS. After spending hours on hold and getting disconnected multiple times, I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. It's a service that basically waits on hold with the IRS for you and calls you back when an agent is actually on the line. I got through to a real person who confirmed that pass-through funds like this aren't reportable income. Saved me literally hours of hold time and stress.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it myself since I needed to talk to the IRS about a completely different matter. The service worked exactly as advertised. I entered my phone number, they called the IRS, and about 1 hour and 40 minutes later (during which time I was working, not sitting around listening to hold music), my phone rang and I was connected directly to an IRS representative. I asked the rep about the situation described in this post too, and they confirmed that acting as a coordinator and temporarily holding funds that pass through your account for a group activity is not considered taxable income. The key is keeping detailed records showing the money came in from multiple people and went out to pay for the specific group expense.

One suggestion based on my experience coordinating corporate retreats: consider setting up a separate bank account just for this transaction. Many banks offer free checking accounts, and having the money go into a dedicated account rather than mixing with your personal funds makes the paper trail much cleaner. I do this for every large group event I organize. It takes maybe 30 minutes to set up a new account, and it makes tracking and documentation much easier. Plus, if you ever did get questioned, having a separate account makes it immediately obvious that you were keeping these funds distinct from your personal money.

What about the 1099-K reporting thresholds? Doesn't Venmo have to report to the IRS when accounts process more than $20,000 and over 200 transactions in a year? Might this trigger something for you?

Important clarification on the 1099-K issue - receiving a 1099-K doesn't automatically mean you owe taxes on that amount. The 1099-K is just an information document that reports gross payment amounts, not net income. Since you're acting as a pass-through coordinator, you would report the 1099-K amount as "Other Income" on your tax return, then deduct the same amount as a business expense when you pay the resort. This nets to zero taxable income from the transaction. The key is documentation. Keep records of: - All incoming Venmo payments with names and amounts - The payment to the resort/vendor - Any receipts or invoices from the resort - A simple spreadsheet showing total collected vs. total paid out This creates a clear paper trail showing you had no net gain from the transaction. Even if you receive a 1099-K, your tax liability from this activity would be zero as long as you can document that all funds were passed through to pay legitimate group expenses.

I went through something very similar when organizing our company's annual retreat last year. We collected about $45,000 through various payment apps including Venmo, and I was terrified about potential IRS issues. Here's what I learned after consulting with a tax professional: The key is treating this as what it actually is - a temporary custodial arrangement, not income. You're essentially acting like a escrow account, holding money temporarily before passing it through to the final recipient. A few practical tips that helped me: 1. Create a simple tracking spreadsheet from day one showing who paid what and when 2. Save screenshots of all Venmo transactions 3. Keep the resort invoice/contract showing the total amount due 4. If possible, try to make the payment to the resort close in time to when you finish collecting funds The multiple transfers due to Venmo's limits actually work in your favor documentation-wise - it creates a clear paper trail. Banks are used to seeing payment app transfers these days, so as long as the amounts align with your normal account activity patterns, you shouldn't have issues. One thing that gave me extra peace of mind was sending a brief email to all participants after the event summarizing the total collected and total paid to vendors. It's not required, but it shows transparency and creates another piece of documentation if ever needed. You're doing the right thing by researching this ahead of time. The fact that you're being thoughtful about proper handling shows this is legitimate coordination, not any attempt to hide income.