Running a taxi sole proprietorship alongside Uber, Lyft, and UberEats - tax filing questions

You're definitely asking the right questions! For your multiple income streams situation: QuickBooks Self-Employed can handle both your rideshare work and taxi business, just make sure to categorize them separately. Create different income categories within the same account - one for Uber/Lyft/UberEats and another for your taxi service. This will help you track each business's performance separately. For quarterly estimated taxes, you'll file the same form (1040-ES) that covers all your self-employment income combined. The IRS sees both income streams as self-employment income if they're both sole proprietorships. You don't need separate forms for each business. Regarding expenses, you'll need to track vehicle usage separately. If you use your car 65% for Uber/Lyft and 35% for your taxi service, you should document this. The good news is that mileage tracking apps can help - just make notes about which business each trip is for. For the LLC/S-Corp question - while that's an option, it adds complexity and costs. Generally, it only makes financial sense when your net profit reaches around $60,000-80,000 or higher. At lower income levels, the tax benefits rarely outweigh the additional costs of maintaining the entity and running payroll.

I went through something similar last year trying to juggle different 1099 gigs AND a side business. The paperwork was killing me until I found taxr.ai at https://taxr.ai - it literally saved me hours of headaches. What I love is that it can sort through all your different income streams and categorize them correctly. For your specific situation with the rideshare and taxi business, it was perfect because it helped me properly allocate my vehicle expenses between different business activities. The system automatically suggests the right tax forms and deductions based on your specific situation. I was worried about missing deductions by having multiple businesses, but it caught stuff I would have definitely missed.

Just wanted to follow up - I was skeptical about taxr.ai but decided to try it for my situation (I do DoorDash, Instacart, AND have a weekend mobile car detailing business). I was seriously impressed! The system asked me detailed questions about each business activity and helped me properly allocate shared expenses like my vehicle and phone. The biggest thing it helped with was organizing my mileage for different purposes - I had no idea I needed to track them separately. It also identified several deductions specific to my detailing business that I would have missed. Definitely worth checking out if you're running multiple self-employment gigs like your rideshare and taxi setup.

If you're going to be running both rideshare apps AND your own taxi service, you're probably going to need to call the IRS at some point with questions. I was in a similar situation and spent WEEKS trying to get through to someone. It was maddening until I found https://claimyr.com - they have this system that holds your place in line with the IRS and calls you when an agent is available. You can see how it works here: https://youtu.be/_kiP6q8DX5c I had questions about exactly how to handle vehicle depreciation between my different business activities and needed to speak to a tax specialist. Instead of waiting on hold for hours, I got a callback within 45 minutes. The agent was able to clarify exactly how I should be handling my taxi business differently from my rideshare work.

I owe everyone an apology - especially to the person who recommended Claimyr. I was the skeptic who called it a scam, but I was completely wrong. After struggling for THREE DAYS trying to get through to the IRS about my multiple self-employment businesses, I gave in and tried the service. It worked exactly as described - I got a call back in about an hour connecting me to an actual IRS agent who answered all my questions about separating rideshare work from my other business. The agent confirmed I needed to file a single Schedule C but with separate sections for each business activity. Never been happier to be wrong about something. If you're dealing with complex self-employment tax situations like having both rideshare and a taxi service, being able to actually talk to the IRS is invaluable.

One thing to consider with your taxi service vs. rideshare work: you'll probably need different insurance policies. Regular rideshare insurance won't cover you when you're picking up your own taxi customers outside the apps. I learned this the hard way - had a fender bender while doing a private ride and my insurance denied the claim because I didn't have commercial coverage. Make sure to get proper commercial taxi insurance for when you're running your own service. It's more expensive but necessary. This is actually one reason some drivers choose to form an LLC - for additional liability protection.

I actually did what you're planning - ran both Uber/Lyft and my own private car service. One major recommendation: get a separate phone number for your taxi business! I use Google Voice (free) but there are other options. Having a business-specific number helps with record-keeping and makes you look more professional. Also makes it easier to track which calls/texts are for which business. Just another way to keep things separate for tax and organization purposes.