What accounting software would you recommend for someone just starting out? I'm running into the same issues as OP but don't want to spend a fortune on QuickBooks or something if there are cheaper options that would work for a small operation.

For someone just starting out, I'd recommend Wave Accounting - it's free for basic accounting and receipt tracking, which is perfect for a small operation. You only pay if you use their payroll or payment processing features. It's what I used for my first two years before upgrading. If you want something with a bit more features but still affordable, FreshBooks has a starter plan that's reasonable and very user-friendly. Xero is another good option that's more affordable than QuickBooks but still robust enough for a growing business. All of these will let you categorize your income and expenses properly, which makes Schedule C preparation much easier come tax time.

This is super interesting - I never thought about it from the model's perspective! So if I understand correctly, if I'm paying my manager a percentage of my earnings, I should technically be sending them a 1099-NEC? Is that something most models actually do? And does it matter if I'm paying through Cash App vs direct deposit?

I hadn't even thought about changing my business structure! Is that process complicated? And does it make record-keeping even more strict?

The process isn't too complicated - you file Form 2553 with the IRS to elect S-Corp status. The main thing is you need to start running payroll and paying yourself a reasonable salary, which means quarterly payroll tax returns. Record-keeping is more formal, yes. You'll need better separation between personal and business finances (which you should do anyway), and you'll have to file a separate tax return for the business (Form 1120-S) in addition to your personal return. Many people use a payroll service to handle the salary part. It's more paperwork for sure, but the tax savings can be significant because only your salary is subject to self-employment tax, not the full business profit.

This! I got hit with a $1,200 penalty my first year in business because nobody told me about quarterly payments. Such a painful lesson.

I've been making some payments but probably not enough. Is there a specific form I should be using for these quarterly payments?

Do you know if you can deduct mileage if you work from home but occasionally drive to client meetings or to pick up supplies?

Absolutely you can! Any driving from your home office to client sites, suppliers, business meetings, etc. counts as deductible business mileage. Just make sure to keep a log with dates, starting/ending mileage, and purpose of each trip. The only driving that's not deductible is regular commuting to a primary workplace. But if your home is your primary workplace (home office), then driving to clients or for business purposes is generally deductible. There's a pretty generous mileage rate too - it was 65.5 cents per mile for 2023.

Which tax software do you recommend for first-time self-employed? I've used the free versions before but now I need something that handles Schedule C.

$1500 is a lot to pay when there are software solutions that do the same thing for way less. I used CoinTracker for my CP2000 response and it worked fine.

You're right that software can work for simpler situations. My case was particularly complex with DeFi staking, liquidity pools, and cross-chain transactions that most software couldn't handle correctly at the time. For someone with straightforward trades on major exchanges, software might be sufficient. But when you're facing a $40k tax bill and have complex transactions, sometimes the expertise and representation of a professional is worth the cost. They can also help if you need to negotiate a payment plan or have other complicating factors in your tax situation.

This is unfortunately common with crypto. If you can't access the original exchange data, try these approaches: 1. Bank/credit card statements showing deposits to those exchanges 2. Email confirmations of purchases 3. Blockchain explorers to verify transactions from your wallet addresses 4. If you have partial records, you can sometimes reconstruct activity based on withdrawals to known wallets Document your attempts to obtain complete records. The IRS does recognize that some extinct exchanges make perfect recordkeeping impossible. They generally just want to see a good faith effort to accurately report your activity. If all else fails, you may need to use "other methods" to establish basis, which a tax professional can help with. It's better to respond with partial records than to ignore the CP2000 entirely.

That's encouraging to hear! Did you claim both EITC and CTC? And did your WMR tool show any tax topic numbers during the processing stage or just the generic "still processing" message?

I claimed EITC but not CTC this year. My WMR showed Tax Topic 152 the entire time, which I've read is actually a good sign that means your return is in normal processing. It was stuck on "still processing" with that tax topic for about 3 weeks. The only update I got was when it suddenly changed to approved, and then the money was in my account the next morning. Capital One did not hold the funds at all, it was available immediately when the deposit hit.

I've been trying to access my transcript online but the IRS verification system won't accept my phone number since it's prepaid. Any other ways to check transcripts without waiting for mail?

If you can't verify your identity online, you can also request transcripts by mail using Form 4506-T, but obviously that takes longer. Another option is to try calling the automated transcript request line at 800-908-9946, which sometimes has less stringent verification. Some people have had success verifying their identity by using a family member's non-prepaid phone number for the verification step, then changing their contact info afterward. Not officially recommended, but might work in a pinch if you're desperate for transcript updates.