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Look into whether your Cash App account is personal or business. I accidentally set mine up as a business account years ago and didn't realize it until I got hit with a 1099-K. All my friend payments were being flagged as business income! You can check in your profile settings. If it's set as business, you might want to create a new personal account for your roommate transactions and keep them separate.
Wait how do I even check this? I literally just signed up with my email years ago and never thought about it. Is there a specific setting I need to look for?
Go to your profile icon, then "Personal" at the bottom. If you see an option that says "Switch to Business" then you're currently on a personal account which is good. If it says something like "Business Settings" or shows a business name, then you have a business account. Cash App also has colors - personal accounts are usually green while business accounts are typically black. Double check this ASAP because it makes a huge difference in how your transactions are reported!
My roommate and I started using Venmo instead of Cash App because we heard they have clearer distinctions between personal and business transactions. Anyone else switch platforms to avoid this issue?
Just as a data point, I've had a Solo 401k with Vanguard for about 5 years now with both traditional and Roth components. They automatically set both up under the same plan number but with different account numbers. From what I understand, this is standard practice and the correct way to do it. The plan number is what identifies your retirement plan as a whole to the IRS, while the account numbers are just for the financial institution's internal tracking. Definitely get them matched up before you have to file any Form 5500 paperwork.
Thanks for sharing your experience! Do you know at what point I would need to file Form 5500? I thought solo 401ks were exempt from that unless the assets exceed $250,000?
You're right that solo 401ks are exempt from Form 5500 filing requirements until your total plan assets exceed $250,000. Once you cross that threshold, you'll need to file Form 5500-EZ annually. Even if you're below that threshold now, it's still good practice to have your plan documentation consistent and organized from the beginning. Makes life much easier if/when you do eventually need to start filing, and prevents headaches if you ever get audited or need to roll the accounts over to a different provider.
I'm surprised nobody mentioned this yet, but you might want to double check if your E-Trade solo 401k plan document actually allows for Roth contributions in the first place. Some off-the-shelf solo 401k plans don't include this option unless specifically elected. If your plan document doesn't include the Roth option but you've been making Roth contributions, that could be a bigger issue than just having different plan numbers.
One thing I learned the hard way - if your PayPal account is registered as a personal account rather than a business account, switch it NOW. PayPal has been cracking down on people using personal accounts for business transactions and can freeze your funds. Also, you might want to look into getting a separate bank account for your business income. It makes tracking expenses WAY easier come tax time, and it's what my accountant recommended when my side hustle started making regular money.
Make sure you're putting aside enough for taxes as you go! When I started my side hustle, I didn't save anything and got DESTROYED at tax time. Now I automatically move 30% of all my side income into a separate savings account the moment I get paid. The self-employment tax (15.3% for Social Security and Medicare) on top of regular income tax is what catches most people off guard. Plus, your side hustle income might push you into a higher tax bracket for your overall income. Also worth noting - you might qualify for the Qualified Business Income deduction which can give you a deduction of up to 20% of your net business income. Definitely look into that!
Don't forget to check if you need a business license for each state where you have nexus! Sales tax is just one piece of the puzzle. I got hit with penalties in three states last year because I didn't realize I needed business licenses even though the marketplaces were handling the sales tax. Check your threshold requirements carefully.
What thresholds should we watch for? Is it the same for all states or does it vary? I'm selling on Etsy and about to expand to Amazon.
The thresholds vary significantly by state. Most common is $100,000 in sales or 200 transactions in a calendar year, but some states have lower thresholds, especially for marketplace sellers. When you expand to Amazon, your nexus footprint will likely increase because of their fulfillment centers. If Amazon stores your inventory in a state, many states consider that physical nexus regardless of sales volume. The good news is Amazon handles sales tax collection in all states, but you may still need business registrations.
What tax software are you guys using to track all this? I'm using a spreadsheet right now but it's getting unwieldy fast.
StarSurfer
One thing nobody's mentioned yet - KEEP RECORDS OF EVERYTHING. If you've submitted your Schedule C, make copies of absolutely everything you sent. When I went through this, the IRS "lost" my first response and claimed they never received it. Luckily I had certified mail receipt and copies of everything. Also, don't forget to look into abatement of penalties. If this is your first offense and you have a good history of filing and paying taxes on time, you can request "first-time penalty abatement" which can potentially remove the failure-to-pay penalties. Won't help with the interest, but could save you a decent chunk of money.
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Amina Bah
ā¢I did keep copies of everything and sent it certified mail, so I have tracking confirmation they received it. Thank god for that tip! How exactly do I go about requesting this first-time penalty abatement? Is that something I can do now or do I need to wait for their response to my Schedule C submission?
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StarSurfer
ā¢You'll want to wait until you get their response to your Schedule C submission, as that will have the updated amount they believe you owe, including any penalties. Once you receive that, you can call the IRS (or use a service to get through) and specifically request "first-time penalty abatement" if you qualify. To qualify, you generally need to have had no penalties in the past 3 tax years and have filed all required returns and paid (or arranged to pay) any tax due. If approved, they'll remove the failure-to-file and failure-to-pay penalties, which can sometimes be a substantial portion of what you owe. Just be sure to specifically use the phrase "first-time penalty abatement" when requesting it, as some representatives won't offer it unless you ask.
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Ravi Malhotra
Don't panic about the initial amount they say you owe! My CP2000 initially said I owed $23k and after submitting my Schedule C with all my expenses, it went down to $4.5k. Make sure you're claiming EVERY legitimate business expense. Some expenses people often forget: home office deduction (if applicable), portion of cell phone and internet bills, professional development/training, subscriptions related to your work, software, professional services (like accounting), bank fees for business accounts, and depreciation of equipment.
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Freya Christensen
ā¢This is key advice. When I got my CP2000 for some freelance work, I initially only claimed the obvious expenses. After doing more research, I realized I could legitimately claim partial use of my vehicle, a portion of my utilities since I worked from home, and even some travel expenses for meetings with clients. Cut my tax bill by more than half.
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