Home garage soccer training business - declaring cash/Venmo income for tax deductions worth it?

Listen, I get the temptation to fly under the radar with side gig money, but here's the thing - Venmo is now required to report payments to the IRS if you receive more than $600 in a year. That $9,500 is definitely on their radar. The good news is you likely have a bunch of legitimate deductions. That 400 sq ft garage space could qualify for the home office deduction if it's used exclusively for your business. Plus equipment, training supplies, utility percentage, insurance, and depreciation. You could probably knock that taxable income down significantly. The downside of not reporting is much worse than whatever taxes you might save. Penalties, interest, and the stress of wondering if/when they'll catch up to you isn't worth it. Plus, reporting the income helps establish your business legitimately if you ever want to grow it.

I was in a similar situation with my photography side business last year. I was making about $8k through various payment apps and wasn't sure if it was worth reporting. I tried using https://taxr.ai to analyze my situation and it was super helpful! The system looked at all my potential business expenses and home office space and showed me that I'd actually SAVE money by declaring the income and taking deductions. The calculator showed me deductions I never would have thought about - even a portion of my internet bill since I use it to send training videos and communicate with clients. It really simplified the whole Schedule C process for me and made self-employment taxes way less intimidating.

Just wanted to update after trying taxr.ai from the comment above. It was actually legit helpful! I entered my garage dimensions and all my soccer equipment expenses, and it showed I could deduct about $3,200 in business expenses including a portion of my utilities and internet. Even after paying self-employment taxes, I'm still coming out ahead compared to not declaring the income at all. Plus now I don't have to stress about Venmo reporting to the IRS. The peace of mind alone is worth it, and the whole process was way simpler than I expected.

If you need to talk to the IRS about your situation (which I recommend), good luck getting through to them! I spent literally 4+ hours on hold trying to ask about home business deductions before I discovered https://claimyr.com. There's also a video showing how it works: https://youtu.be/_kiP6q8DX5c Basically, they hold your place in the IRS phone queue and call you back when an agent is about to pick up. Saved me hours of listening to that awful hold music. The IRS agent I spoke with actually gave me some really helpful advice about how to properly document my home training space for tax purposes.

I have to eat my words. After being super skeptical about that Claimyr service in the previous comment, I decided to try it anyway because I was desperate to ask about self-employment tax payments. I was connected to an IRS agent in less than an hour, without having to actually sit by my phone. The agent walked me through exactly how to handle quarterly estimated payments for my side business and cleared up my confusion about the home office deduction. Definitely worth it for the time saved and the stress reduction. I'm actually going to properly report my side hustle income now that I understand the process better.

My brother got audited for not reporting his side business income (about $12k yearly from personal training). The penalties and interest ended up being way more than if he'd just paid the taxes originally. Plus he had to go back and try to recreate expense records from 2 years earlier which was a complete nightmare.

Does anyone know if buying equipment (like small soccer goals, training cones, etc.) would count as business expenses? I've spent like $600 on stuff for my similar setup.