Ask a CPA

As a CPA, I came across this website and joined just last week, and I just came across your question.

I agree with your attorney wholeheartedly that you should talk with a CPA about your specific circumstances (and the specific circumstances of the other potential LLC member) in order to plan the best way to structure the business for tax purposes. Also, in making that decision, it’s important to consider what you plan to do with the business. Keep in mind that an LLC is a creation or creature of state law. How it is treated for federal income tax purposes is a completely separate matter. Because two of you are involved, you are correct that (for federal income tax purposes), the LLC can be treated as a partnership, C-corporation, or S-corporation. Making the Subchapter S election is how you elect to treat an LLC as an S corporation, so a Subchapter S election is not a fourth type of entity/choice.

In all honesty, the issue of entity election that you are raising is one that is extremely fact-specific, so you really should engage a CPA to listen to your situation and advise you. Feel free to check out my profile on this website as well as Google reviews and please feel free to contact me, if you wish to engage me to help navigate you through the issue at hand.

As a CPA, I came across this website and joined just last week, and I just came across your question.

Unfortunately, no, you will not be able to avoid the tax on capital gains. As you know, as long as you own the stock, you don’t pay any tax on unrealized gains. When you sell stock, you realize gains and pay tax. There is not an exception to that rule, just because you’re using the proceeds to purchase assets for a business.

Trying to think outside the box, even if you could contribute the stock to a business of yours and manage to get tax-free treatment on the contribution of the stock to the business, you’d still run into the same problem when the business tried to sell the stock to get the money to purchase assets. In that case, the business would have to either pay tax itself (at its marginal tax rate) on the capital gains or pass the gains to you and you’d have to pay the tax (depending on how the business was structured for federal income tax purposes).

It’s great that you’re trying to be proactive and find a way to save taxes, but I don’t think it’s a go this time.

Even though you cannot avoid the tax on the capital gains, you should consider depreciation on the assets your purchase for the business. That might help offset some of the tax on your gains. Just a thought.

I wish you the best in your endeavors.

Because DoorDash, GrubHub, and Uber Eats are all online food ordering and delivery platforms, you’re basically doing the same activity, just for different companies. Therefore, IRS will consider them one business. You should file just one (1) Schedule C for all three activities. On the other hand, if you were also doing a completely different activity, such as landscaping, you would need to file two (2) separate Schedules C, one for the online food delivery activity and one for the landscaping work. May you have a successful and safe business!

Congratulations on the sale!

As a CPA, I came across this website and joined just last week, and I just came across your question.

If you just sold an investment property in 2021, the income taxes on the capital gains are due on or by April 15, 2022.

You raise a good question. Without knowing the details of your tax situation, I can say that, in general, it is wise to make an estimated income tax payment using the 2021 Form 1040-ES for the estimated income taxes on the capital gain from the sale of the investment property as soon as possible. Why? To avoid the estimated income tax penalty that could be assessed. If applicable, that’s determined when you prepare your tax return next year. To pay in the next quarter, as you suggest, should be fine.

Also, this is assuming that the sale of the investment property was not structured as an installment sale. Additionally, this assumes that the property in question was always an investment property, never a primary residence or a rental property, so you must take the history of the property into consideration.

If you held the investment property for one year or less, you would pay tax at the same marginal tax bracket as your other ordinary income. On the other hand, if you held the investment property for more than one year, you would pay income tax at the long-term capital gains tax rate (maximum 20%).

Finally, you would need to consider if the 3.8% net investment income tax also applies to your situation.

As a CPA, I came across this website and joined just last week, and I just came across your question.

You use Form 1040-ES to make estimated income tax payments. You can download the form (with instructions on where to mail, etc.) on the website for the Internal Revenue Service (irs.gov). On the home page, click on Search Forms & Instructions. Then, in the Search box, you can type 1040-ES.

Estimated income tax payments are normally due April 15, June 15, September 15, and January 15.

As a CPA, I came across this website and joined just last week, and I just came across your question.

If you received a corrected composite Form 1099 with Line 1a (ordinary dividends) and Line 3 (nondividend distributions) switched, it would definitely make a difference. Why? Because ordinary dividends are income that must be reported, subject to either the long-term capital gains rate applicable to you or the marginal tax rate on ordinary income for you. The extent to which each rate applies to you depends on how much is reported in Line 1b (qualified dividends). So whether line 1a (ordinary dividends) went up or down with the corrected composite Form 1099, it would have an impact on your taxes.

Having said that, I feel that whether or not you should do an amended tax return depends on the amount of the change from the corrected composite Form 1099. If it was material, I would do an amended return. If it was de minimis (very small), I wouldn’t bother. Just know that if you do not amend, you should not be surprised to eventually receive a notice from the Internal Revenue Service, potentially assessing more tax plus some penalty and interest. That’s why I recommend you make your judgment based on the dollar amount involved. If the amount involved is very small, the time (and potential expense to pay someone to amend) doesn’t make sense.

I hope that helps. I wish you the very best!

As a CPA, I came across this website and joined just last week, and I just came across your question.

If you are limiting your choices to either a dba or an LLC, then I would recommend an LLC, for three reasons.

First, an LLC gives you some legal liability protection if you are ever sued. A dba does not give you any legal liability protection.

Second, from a tax perspective, both a dba and an LLC would be taxed the same (for federal income tax purposes), assuming that you did not make any election to treat the LLC differently. However, having an LLC gives you the option to elect to treat the company as an S corporation. You don’t have that optionality with a dba. Keep in mind that making the S election for the LLC would require that you file a separate federal income tax return for the business each year. However, the tax savings that an S corporation election can afford could make it worthwhile, especially because it sounds like you intend to grow the business.

Finally, the LLC probably gives your business a little more legitimacy and professionalism, in the public’s eye.

Consider that you could choose the LLC and have the LLC get the dba – the best of both worlds. So you don’t necessarily have to treat this decision as one where you must choose one or the other.

I congratulate you on planning for the future. If you wish to engage me to help, please feel free to reach out to me.

As a CPA, I came across this website and joined just last week, and I just came across your question.

Good question. I commend you for planning ahead so that you don’t end up owing a large balance or incurring the estimated income tax penalty (Form 2210) come tax-time next year.

Both of your suggestions are acceptable. You are right that there is still a lot of time left in the year, so increasing your federal income tax withholding is an option. Alternatively, you could start making estimated income tax payments via Form 1040-ES for 2021.

As a CPA, I came across this website and joined just last week, and I just came across your question.

Unfortunately, yes, you need to file a Form 1120S, which will include the Schedules K and K-1 for 2020. S corporations must file a return every year, whether or not there is any activity. Don’t forget about any state return, such as a state income tax return, franchise return, or annual report. Feel free to contact me if you wish to engage me to help.

The standard deduction amounts will increase to $12,200 for individuals, $18,350 for heads of household, and $24,400 for married couples filing jointly and surviving spouses.

For 2019, the additional standard deduction amount for the aged or the blind is $1,300. The additional standard deduction amount increases to $1,650 for unmarried taxpayers.

For 2019, the standard deduction amount for an individual who may be claimed as a dependent by another taxpayer cannot exceed the greater of $1,100 or the sum of $350 and the individual’s earned income.