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Another thing to consider - if your child has earned income, you might want to help them open a Roth IRA! They can contribute the lesser of their earned income or $6,500 (2025 limit). Since your child probably has a low tax rate now, a Roth can be an amazing long-term investment vehicle. I started my daughter on this when she got her first 1099 income at 15, and she's already building a nice nest egg. Just make sure the income is legitimate and documented in case the IRS questions it.
That's a great idea! I hadn't even thought about retirement accounts. Would we need to wait until after we file taxes to open the Roth IRA, or can we do it now based on the 1099 amount?
You can open and fund the Roth IRA anytime between January 1, 2025 and the tax filing deadline (usually April 15, 2026) for the 2025 tax year. You don't need to wait until after filing taxes. Remember that the contribution limit is based on earned income after business expenses. So if your teen's net self-employment income ends up being $550 after deducting the computer and software expenses, their maximum Roth contribution would be $550 for the year, not the full $1,400 from the 1099-NEC.
Mia Alvarez
Don't forget your kid might need to make quarterly estimated tax payments if they continue this self-employment gig! My son got hit with an underpayment penalty because I didn't realize this applied to him.
I think there's a safe harbor exception for dependents with small amounts of income? My accountant told me my daughter didn't need to worry about quarterly payments for her babysitting income until it was more substantial.
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Levi Parker
Something else to consider - Robinhood does let you download transaction history as CSV through the app or website, which isn't the same as their tax documents but can be helpful supplemental info. Go to Account ā Statements & History ā Export, and you can select date ranges to download transaction data. While this doesn't have all the tax lot information that appears on the 1099, it can help you verify things if needed. Also, if you're using Robinhood for cryptocurrency, be aware their tax reporting for crypto is still pretty basic. You might want additional tracking software specifically for crypto transactions.
Nathan Dell
ā¢That's a good point about the transaction history. Do you know if the CSV export includes cost basis information? And regarding crypto, have you found any good solutions for tracking those transactions from Robinhood?
Levi Parker
ā¢The CSV export does include the purchase price for stocks and options, which gives you the cost basis information. However, it doesn't automatically calculate adjusted basis for wash sales - you'd need to do that yourself or use tax software. For crypto tracking from Robinhood, I've found CoinTracker works pretty well. You can't directly connect it to Robinhood automatically, but you can import the transaction CSV from Robinhood into CoinTracker. It takes a bit of manual work upfront, but then gives you much better crypto tax reporting than what Robinhood provides. Koinly is another option some friends have used successfully with Robinhood exports.
Libby Hassan
Also worth noting that Robinhood's tax documents are usually available pretty early in tax season (late January/early February in my experience), which is nice compared to some other brokers that make you wait until mid-March. The PDF they provide breaks down your transactions into the categories that match Form 8949 (short-term, long-term, etc.), which makes manual entry easier if you go that route. Each section is clearly labeled to correspond with the right part of Form 8949.
Not my experience at all. Last year, Robinhood sent corrected 1099s THREE TIMES, with the final one coming in early April. Totally messed up my filing timeline. Apparently it's pretty common with them if you have wash sales or more complex situations.
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Lim Wong
Another option nobody mentioned - you could potentially use Section 195 startup expense rules. This lets you deduct up to $5,000 of startup costs in your first year of business (the year you actually started operating), with any excess amortized over 15 years. In your case, since your business actually started operating in 2024 (you did the work), you could claim these as startup expenses on your 2024 return, even without income. Just make sure you're actually "in business" and not just in the planning stages. Keep in mind this is distinct from the general business expense deduction others mentioned. Might be worth looking into both approaches.
Dananyl Lear
ā¢Is there any advantage to using Section 195 vs just regular business expenses on Schedule C? Seems like either way the result is the same - deducting expenses in 2024 even with no income.
Lim Wong
ā¢For smaller amounts like we're discussing here, there's typically no significant difference in outcome between claiming them as regular business expenses or Section 195 startup costs. Both approaches would allow deducting the expenses on your 2024 return. The main difference becomes relevant if you have startup costs exceeding $5,000, in which case Section 195 has specific rules about amortizing the excess. Also, Section 195 specifically addresses expenses incurred before your business began operating, while regular business expenses are for ongoing operations.
Has anyone mentioned the tax implications if the OP decides to quit freelancing after just this one project? I had something similar happen - claimed startup expenses for a business that I ended up abandoning after just one client. The IRS sent me a letter questioning the business loss because I didn't continue the business in subsequent years. Had to provide documentation proving I genuinely intended to continue the business when I made those investments.
Ana Rusula
ā¢This is a really good point! The concept is called "continuity and regularity" - the IRS wants to see that you're pursuing the activity with continuity and regularity for profit rather than as a one-off.
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Since this hasn't been mentioned yet - you should know that profit sharing contributions are completely discretionary year to year, which is incredibly valuable for professional practices with fluctuating income. Some years you can contribute the full 25%, other years you can reduce or skip it entirely depending on cash flow. Also, make sure the plan documents are properly amended to include the profit sharing component. This is something your plan administrator needs to handle formally - you can't just start making profit sharing contributions without updating the plan design. One thing your CPA might not have emphasized: the timing of cash flow matters. The S Corp needs sufficient profits distributed from the LLC to make these contributions. Planning the timing of distributions from LLC to S Corp becomes important if you want to maximize these retirement contributions while maintaining adequate operating capital.
Thanks for this insight. The discretionary nature is really appealing since her income can vary quite a bit. Do you know if there's a deadline for deciding whether to make a profit sharing contribution for the current tax year? Like could we wait until March 2025 to decide about 2024 contributions?
You can actually wait until your S Corp's tax filing deadline including extensions to make the profit sharing contribution for the prior year. So for 2024 contributions, if your S Corp files for an extension, you could have until September 15, 2025, to make the decision and the actual contribution. This flexibility is one of the biggest advantages of profit sharing plans for professionals with variable income. Just make sure the plan documents are amended before the end of the plan year in which you first want to make profit sharing contributions. The plan has to allow for profit sharing before you can actually make those contributions.
Yara Haddad
Wait, I'm confused about something! You said the LLC already handles your wife's regular 401K contribution before the money reaches the S Corp. Does that mean she's technically an employee of the LLC rather than the S Corp? Because that would change everything about how this works. If she's getting a W-2 from the S Corp (which it sounds like she is), then the LLC shouldn't be handling any 401k deductions - that should all be happening at the S Corp level. The way you described it sounds like there might be a potential compliance issue with how things are currently structured.
Not necessarily a compliance issue. In many medical groups, the LLC sponsors the 401k plan but the participating doctors are technically employed by their own S Corps. The plan documents just need to specifically allow for this arrangement. It's super common in group practices.
Scarlett Forster
I've used H&R Block premium for the last 3 years and it's been worth every penny for me. The interface is more intuitive than TurboTax in my opinion, and they have good support. One thing to watch out for with ANY paid service - watch the upsells! They all start advertising audit protection, tax pro review, etc. halfway through, and suddenly your $75 software costs $200+. I usually just get the base premium package and skip the extras.
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Arnav Bengali
ā¢Do you think the H&R Block is better than TurboTax for someone with investment income? I've heard TurboTax handles stocks better.
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Scarlett Forster
ā¢In my experience, both handle basic investment income (dividends, capital gains, etc.) equally well. TurboTax might have a slight edge if you have very complex investments like partnership K-1 forms or foreign investments. H&R Block's interface for uploading 1099-B forms is cleaner and shows a better summary view of all your investment transactions. Their cost basis tracking between tax years is also more transparent. If you're dealing with normal stocks and basic investments, I prefer H&R Block, but for really complex situations, TurboTax might have more specialized features.
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Sayid Hassan
Has anyone used the tax pro review add-on that most of these services offer? It's like an extra $100 but they supposedly have a pro review your return before filing. Wondering if it's just a money grab or actually worth it.
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Rachel Tao
ā¢I used the TurboTax tax pro review last year. The "expert" literally just glanced over my return and said everything looked good. Took them maybe 15 minutes on a video call, and I didn't feel like they caught anything I wouldn't have. Complete waste of money imo.
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