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Someone I know tried the IRA-LLC structure for a different business (not blogging) and ran into major issues. The Self-Directed IRA custodian charged insane fees, and when the business generated over $1,000 in UBTI, they had to file Form 990-T which was a nightmare without professional help. Plus, their IRA had to pay the business fairly if they wanted to be involved personally. They ended up paying themselves a "fair market salary" from the IRA-owned LLC, which means that money was essentially taxed anyway (defeating some of the purpose), plus they had extra compliance costs. For a blog specifically, seems like WAY more headache than benefit unless you're planning to generate massive profits without personal involvement.
Did your friend have to completely dissolve the LLC eventually or were they able to make it work? I'm trying to understand if this is simply complex but doable vs actually impractical for most people.
They didn't dissolve it, but they had to restructure everything. They created a management company outside the IRA that handled all operations, then the IRA-LLC just became a passive investor in certain aspects of the business. Made the whole setup way more complicated and expensive than just running a regular business. The fees were also eye-opening - about $1,500 in annual custodian fees, plus tax preparation costs for the LLC itself and Form 990-T filings. For a blog, unless you're making serious money (like $50k+ annually), the compliance and administrative costs would probably eat most of your profits.
Just to add another consideration - what about SEO expenses and content creation costs? If the blog is in your IRA, you can't personally pay for things like hosting, domain registration, SEO tools, etc. All expenses MUST come from IRA funds. And if your blog needs capital for growth (better design, hiring writers, marketing), you're limited to what's in your IRA. You can't just add personal funds whenever needed without doing a formal IRA contribution (with all the normal limits).
That's such a good point. I didn't even think about the practical aspects of running the business. Would using personal credit cards for blog expenses count as a prohibited transaction too?
Don't forget that the wash sale rule can seriously mess with your "simple" profit and loss calculation. If you sell a security at a loss and buy the same or "substantially identical" security within 30 days before or after the sale, you can't immediately claim that loss for tax purposes. I learned this the hard way last year trading tech stocks. Thought I had a $15k net loss only to discover that most of my losses were disallowed because I kept jumping in and out of the same stocks. The losses didn't disappear forever, but they got added to the cost basis of my replacement shares instead of offsetting my gains.
Thank you so much for pointing this out! I didn't even consider wash sales. Looking at my trading pattern, I definitely bought back into some positions within that 30-day window after selling at a loss. Does the wash sale rule apply across different brokerage accounts too? Like if I sell at a loss on Fidelity and then buy the same stock on Robinhood within 30 days?
Yes, the wash sale rule absolutely applies across different brokerage accounts. The IRS doesn't care which platform you use - if you sell at a loss on Fidelity and buy the same stock on Robinhood within that 30-day window, it's still a wash sale. This is actually one of the biggest traps for traders who use multiple platforms. Your individual brokers won't know about trades you make elsewhere, so their reporting might not flag wash sales that actually exist when you look at all your accounts together. This is why tax software that can consolidate all your trading activity is valuable - it can identify wash sales that individual brokers miss.
Another thing to consider is that if trading is your actual job/business rather than just investing, the tax treatment can be completely different. If you qualify as a "trader" in the eyes of the IRS (which has specific requirements about frequency, volume, and intent), you might be eligible for "trader tax status" and could potentially elect the Section 475 mark-to-market accounting method. This would treat all your trades as ordinary income/loss rather than capital gains/losses, bypassing the $3,000 capital loss limitation and wash sale rules. But this is a serious election with major implications and specific deadlines.
Don't forget about state taxes too! The home office deduction can sometimes save you money on state income taxes depending on where you live. In my case, I saved about 6% on state taxes on top of the federal savings, which added up to a few hundred extra dollars. Also, if you're self-employed, the home office deduction can help reduce your self-employment taxes too, which is huge since those are like 15.3% on top of regular income tax.
Does this still apply if you're a w2 employee but work remote? My company is based in another state but I work from home 100% of the time.
Unfortunately, if you're a W2 employee working remotely, you currently can't take the home office deduction, even if you work from home 100% of the time. The Tax Cuts and Jobs Act suspended home office deductions for employees through 2025. This deduction now only applies to self-employed individuals, independent contractors, or other business owners. If you get a W2 from your employer, you can't claim it regardless of your remote work status. Some companies offer stipends for home office expenses instead, so it might be worth asking your HR department if that's an option.
I find the simplified option much easier than tracking all those expenses. You can deduct $5 per square foot for up to 300 square feet instead of calculating percentages of all your bills. So if your office is 10% of your 2000 sq ft home (200 sq ft), that's a $1000 deduction. Less paperwork and less audit risk.
But wouldn't I save more using the regular method with my specific expenses? The simplified method seems like it would give me a much smaller deduction given the high housing costs in my area.
One option nobody's mentioned yet - if this was 2024 income and you haven't filed yet, you could open a SEP IRA and contribute some of your 1099 earnings to that. You can contribute up to 25% of your net earnings and it's tax-deductible, which could significantly reduce what you owe. You need to open the account before you file your taxes, but you have until the filing deadline to fund it. Could be a good way to save for retirement AND reduce your current tax bill.
Thanks for this suggestion! So if I understand right, I could open this SEP IRA now and put some money in it before filing, and that would lower my taxable income? How is this different from a regular IRA? And can I still do this even though we're already in 2025?
Yes, that's exactly right. You can open and fund a SEP IRA for 2024 all the way up until the tax filing deadline (April 15, 2025), including extensions if you file for one. The main difference from a regular IRA is the contribution limit. A traditional IRA only allows you to contribute $7,000 for 2024 (or $8,000 if you're 50+). A SEP IRA lets you contribute up to 25% of your net self-employment income or $69,000, whichever is less. So if you made significant 1099 income, you can potentially shelter a lot more money from taxes.
Quick tip from someone who's been a contractor for years - start tracking EVERYTHING for 2025! Get a dedicated credit card for business expenses, save all receipts, and track mileage with an app. Common deductions people miss: home internet (% used for work), cell phone (% for work), home office (if you have dedicated space), health insurance premiums, half of self-employment tax, business travel, professional development/courses, software subscriptions, and office supplies.
What apps do you recommend for tracking expenses? I'm terrible at keeping receipts and always forget what things were for by tax time.
Sean Kelly
One thing nobody mentioned - check your transcript if you can access it online! The WMR tool is notoriously unreliable especially for PATH Act returns. My transcript showed codes 571/570 followed by 571/768/766 days before WMR updated. My DDD ended up being the cycle date + 6 days even though WMR still said processing.
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Zara Malik
ā¢Those transcript codes are so confusing tho. What do all those numbers even mean?
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Luca Greco
My theory is the IRS intentionally gives vague info about PATH Act refunds to prevent people from calling all at once. I've gotten EITC for 5 years straight and every year is different. Last year my refund hit my acct on Feb 24th, the year before it was March 10th. Both times I filed in January. š¤·āāļø Just have to be patient even though it sucks when you need the money.
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