No business owner particularly likes the amount of work required to calculate taxes (to say nothing of the actual amounts paid), but calculating and paying taxes is both a legal obligation and also a responsibility entrepreneurs undertake in return for the substantial support that society affords us.
Beginning entrepreneurs are sometimes excessively scared about the tax liabilities involved in starting a business. We want to demystify them, so that you have a good understanding of what you’ll be asked to pay, roughly how much it will end up being, and how to organize your business such that calculating and paying taxes will be as painless as possible.
There are many varieties of taxes in the United States and worldwide. This guide covers a subsection of taxes which your U.S. corporate entity will likely have to pay. Entrepreneurs or owners of companies may realize income as a result of working for the company, receiving dividends, capital gains; make sure you also handle your personal obligations.
As we saw in the chapter on accounting, the entire profession of accounting exists in large part to help you correctly figure what taxes you owe. This brief guide is not a substitute for the professional advice from your accountant. Get an accountant—their advice will almost certainly save you money and stress.
What is tax planning?
Somewhat surprisingly to entrepreneurs, there are often multiple ways to apply tax law to the economic facts of your business. This can result in different amount of taxes, depending on how one applies the law. Accountants help businesses develop a tax position which is both compliant with the law and which is efficient in amount of taxes required.
Tax planning often starts well in advance of the tax being due or even the transactions being entered into. For example, given that one wants to award employees equity in the business (to attract desirable employees and reward them appropriately for the hoped-for success of the venture), one makes consequential decisions about business structure at incorporation, perhaps even before employing one’s first employee. The eventual realization of the value of that equity, and the tax consequences for those future employees, might happen in 5 to 10 years down the road!
Tax planning is legal and expected of businesses. As judge Learned Hand wrote in 1934, summarizing centuries of precedent:
Anyone may arrange his affairs so that his taxes shall be as low as possible; he is not bound to choose that pattern which best pays the treasury. There is not even a patriotic duty to increase one’s taxes. Over and over again the Courts have said that there is nothing sinister in so arranging affairs as to keep taxes as low as possible. Everyone does it, rich and poor alike and all do right, for nobody owes any public duty to pay more than the law demands.
Tax agencies often, however, take a dim view of abusive tax structuring, where the sole rationale for some action of the business is to avoid taxes, and can impose substantial penalties when it occurs. Tax can be a very complicated subject, which is one more reason to have your accountant and/or lawyer review consequential changes to your tax strategy. They can provide you advice on whether you’re doing something which is mainstream in your country/industry or something which has a higher risk of causing your returns to be judged insufficient by tax agencies you are subject to.
Delaware franchise tax
Delaware, like many states, charges all companies incorporated in Delaware a “franchise tax.” You can think of the franchise tax as an annual fee to renew the registration of a corporation—in some states, the fee is indeed called a fee.
Almost all taxes are assessed on revenue or profit. The franchise tax is different. There are two ways to calculate it; both in principle start at a relatively low number and scale with the complexity of the company.
You, or your accountant, can calculate your franchise tax in under two minutes. The rules and formulas are on the State of Delaware’s website.
Companies incorporating with Stripe Atlas will generally owe the minimum tax under the Assumed Par Value method.
Franchise tax is due with your Annual Report filing, which you have to do by March 1st of every year. U.S. corporate tax returns are generally due on April 15th (assuming your fiscal year is the calendar year); it’s generally easiest to file your franchise tax when doing your tax return preparation for the corporate tax return, which (since you’re well-organized) will be done and ready to go sometime in February.
Entrepreneurs can file their own Annual Report and franchise tax relatively easily through Delaware’s website, in most cases without requiring professional advice. Your accountant can also do it for you; expect to pay a nominal amount (perhaps $100 or so) for this.
LLCs formed using Stripe Atlas will generally pay an annual Delaware LLC tax of $300, which is due on June 1st of each year.
Here. Be. Dragons.
In the United States, businesses can be required to collect sales tax by their local jurisdiction (city, county, etc) and by their state. This happens in every jurisdiction where the company both a) has a transaction take place and b) has “nexus” or a connection to the jurisdiction.
In general, internet companies only have nexus in locations where they have physical property or employees doing work on their behalf; however more and more states are changing their laws to broaden what it means to have nexus and, as a result, requiring more sellers to collect and remit tax. You may have nexus simply by means of incorporating in a state, by having customers in a state, or by rewarding persons in the state for referring customers to your website. Each state has its own rules regarding what activity constitutes nexus. There is more information about how and where to register for tax here.
Once you have registered to collect tax in a location, you will generally be required to collect the tax from customers, display on each transaction how much tax you are collecting, and remit the tax to the appropriate government agency on a monthly or quarterly basis.
Many localities in the U.S. also have a “use tax”, which corresponds to the sales tax. A use tax is paid by the customer in a transaction, not by the seller—customers are supposed to tell the local taxation agency “I am using some property which I purchased outside of this jurisdiction; here’s the tax payment.” Some people believe that compliance with use taxes is very, very, very low. Nonetheless, you may have a filing requirement if your business has a presence in a U.S. state—check with your local state and/or city/county.
The complexity of a sales tax filing depends greatly on the specifics of your business, including what you sell, how you record the locations of transactions/buyers, how easy it is to determine where your business’ nexus or nexuses are, and the like. As a rule of thumb, most internet businesses will get their sales tax returns filed by the same accountant who handles their corporate income tax return. It will generally cost a few hundred dollars in professional services fees, but this depends on the complexity of the business.
Corporate income tax
Profits of C corporations are taxed at the federal level and at the state level. The main form for the federal return is Form 1120.
Some tax returns or government filings are simple enough to do yourself. This is not one of them. While it looks simple (only five pages at first!), you should absolutely, positively have a professional tax preparer or accountant involved in the preparation of any corporate tax return. It is relatively easy to make consequential mistakes, and sorting them out will be a distraction from running your business. Additionally, there are a variety of ways to characterize things which are not mistakes per se but which will result in you paying excessive amounts of tax relative to equally valid ways to characterize the same economic facts.
Income tax is only levied on income, rather than revenue. Income is, generally speaking, revenue minus expenses. Most things which you purchase on behalf of the corporation, including the salaries of the founding team and employees, can be deducted immediately as expenses.
A relatively smaller number of things cannot be expensed but have to be capitalized; their (generally high) upfront cost gets apportioned to the business over the useful life of the thing. This is also referred to as “depreciation” or “amortization.” Internet businesses do not typically have high capital expenses early in their lives, particularly as the historic sources of capital expenditures (servers, networking equipment, custom software development, etc) are increasingly rented at-need from cloud providers for fairly small (and expensible) sums of money.
Your accountant can provide you with authoritative advice on whether any particular expenditure needs to be amortized.
If you have a physical presence in a U.S. state, your corporation may owe state income taxes in addition to federal income taxes. Your accountant can advise you on whether your company has a filing requirement in the state(s) in which it physically exists or does business, and can help you prepare those filings. Some states have been getting more aggressive at claiming that internet activity can, in some circumstances, give rise to a filing requirement.
LLC federal income tax
Profits of an LLC are generally passed through to the LLC’s owners and taxed on the owner’s federal tax returns. LLC’s that are owned by just one member are treated as disregarded entities by the IRS, and LLC’s that are owned by more than one member are treated as partnerships. While the profits of the LLC flow to the owners, there still may be a tax return filing requirement for the LLC itself. For example, an LLC owned solely by a non-US individual is required to file Form 5472 with the IRS, and LLC’s owned by multiple members are required to file a partnership return, Form 1065.
Similar to the federal taxes for a C Corporation, you should absolutely, positively have a professional tax preparer or accountant involved in the preparation of any federal tax returns related to the profits earned by your LLC. Tax reporting depends on how your LLC is set up, and it is easy to miss where reporting is required or how profits are allocated to the owners of the LLC.
One advantage of LLCs is that they provide for flexibility with respect to how the profits are taxed. For example, LLC’s have the option of filing an election with the IRS to be taxed as a C Corporation. If you are interested in this option, it is recommended to talk with a tax advisor to understand the tax implications and election filing requirements.
Taxpayer ID numbers
All tax returns are associated with taxpayer identification numbers. There are several varieties of this. The ones you’ll see most frequently are:
Social Security Numbers (SSNs): U.S. citizens and people authorized to work in the U.S. are issued a number by the Social Security Administration. This is widely used by governmental agencies and private entities alike to identify them. The SSN is considered very sensitive (because knowing it is often used to authenticate whether someone is a particular person).
The general form of a SSN is 123-56-6789.
Companies do not have SSNs. You may not have a SSN if you are not a U.S. citizen or have not been employed in the U.S. before. You will instead provide one of the following when asked:
Individual Taxpayer Identification Numbers (ITINs): Any natural person (a living, breathing human) who needs to file taxes but cannot receive a SSN (because the SSN typically requires legal right to work in the U.S.) can ask the IRS for an ITIN, which functions as a substitute SSN. They are not very tricky to get—you simply file an W-7 form and wait roughly six weeks.
Most owners of Stripe Atlas companies will not themselves need an ITIN; your company will file U.S. taxes, but you yourself might not have U.S. tax filing obligations. If your accountant tells you otherwise, file an W-7 and get one issued. You can also get one issued contemporaneously with any tax filing; submit the tax filing on paper with the ITIN listed as “pending” and include a W-7 form. This generally introduces a delay in the processing of your tax filing, and should be avoided where you can, but it is always better to file in a timely fashion and have the processing delayed than to fail to file or file late.
An ITIN looks like a SSN, but the first digit will always be 9.
Employer Identification Numbers (EINs): EINs identify corporate persons (i.e. companies) not natural persons (actual people). You receive an EIN after filing an SS-4 with the IRS; if you incorporated through Atlas, we took care of this for you.
You will routinely be asked for your EIN by financial institutions in the U.S., and occasionally by other businesses. It is probably not a good idea to publish it, but they’re not treated as sensitive as SSNs are. (The disclosure of your SSN to an unauthorized person is an immediate emergency; the disclosure of your company’s EIN happens rather routinely.)
An EIN looks like 12-3456789. Note that this is the same number of digits as a SSN but the hyphen placement is different. It is, unfortunately, not the case that the hyphens don’t matter—some SSNs have the same numbers in the same order as some EINs, so make sure you’re always filling in the right box and including the hyphens in the right spaces.
Companies, including your own, have an obligation to report certain transactions to the government via “informational returns.” The government matches informational returns against the tax filings of individuals and corporations, to make sure that taxpayers do not forget to pay taxes on income they have received.
Your company will routinely issue informational returns. You may occasionally receive them, and so should understand how that process works as well.
There are several varieties of informational returns. The two you are most likely to issue are the W-2, which records wage income to an employee, and the 1099-MISC, which shows payment for services to an individual contractor. (You will not ordinarily issue a 1099-MISC to a company, even if you buy services from them.)
Your accountant will take care of filing W-2s and 1099s on your behalf, early in the calendar year. You will provide one copy to the taxpayer you’re reporting on, one to the IRS, and keep one for your own records.
To issue any informational return, you need someone’s tax ID number—typically SSN for W-2s and either an SSN, ITIN, or (rarely) an EIN for 1099s. There is a form to formally ask someone’s tax ID number; it is the W-9. One only uses the W-9 with U.S. taxpayers; if someone is not a U.S. person (for example, if you’re employing someone overseas), you’ll want to get them to give you a W-8BEN instead. (This provides a paper trail in the event the IRS asks “Why didn’t you file a 1099 for that contractor?” “They don’t have U.S. tax liability so we don’t have to.” “Oh really?” “Here’s their W-8BEN.” “OK then.”) Because the IRS loves its forms, there is a separate one (the W8-BEN-E) for when you need a W8-BEN from a corporate entity.
Your company may occasionally be asked for a W-9 or W8-BEN. This could happen if someone believes they need to file, or may need to file, an informational return about you. For example, a financial institution may ask for one of these to open an account, in anticipation of perhaps needing to file a 1099-INT to report interest income at a later date.
In some cases, you might be asked for one of these forms by mistake. Some relatively common mistakes:
Only U.S. persons (including corporations) should be asked for a W-9. If you are not a U.S. person, you should be asked for a W8-BEN.
Any company incorporated in the U.S. is a U.S. person, regardless of who owns it. Many Stripe Atlas customers have Delaware C corporations whose address and operations are international; these are still U.S. persons and hence should only file W-9s not W8-BEN-Es.
Sometimes individuals at companies ask for these forms when they have no actual need for them. You have no particular obligation to provide them if there is no legal requirement for an informational return. That said, companies have no particular obligation to do business with you, and some companies will request these forms at certain points as a matter of policy. Often the easiest resolution is to say “Can you check with your accountant to see if that is really necessary?” You might sensibly decide to simply provide the form, even if not required to.
It is generally in your interest to provide W-9s or W8-BENs! A common reason why your counterparty is asking for it is to document their decision to not withhold money on your behalf. (If you’re unknown to the U.S. tax system, they might have a legal obligation to withhold perhaps 30% of your payment and send it to the IRS. The IRS will then wait for you to file a return and perhaps get some of that back. The assumption is that people who are known to the tax system are honest and can be trusted to hold onto their own money before filing a return to determine what portion should be sent to the IRS. A W-9 says “The relevant laws say that the IRS implicitly trusts me, so you have all the legal justification you need to pay me what we’ve agreed and not withhold anything.”)
Your company may receive informational returns. The most likely one for Atlas customers is a 1099-K from Stripe, showing revenue from processing credit cards in a year. You don’t have to do anything in response to an informational return and you don’t have to send it on to the IRS—they already received a copy. You’ll already have the income shown on the return recorded in your books somewhere, and your books drive your tax return.
The scenario where an informational return actually matters is where the return shows a large amount of money and one’s corporate tax return doesn’t obviously reflect that money on it. This can result in the IRS doing a correspondence audit, basically asking “We know you received $5,000 in interest last year. Where did that show up on your tax return?” Since you are a law-abiding taxpayer, you’ll have a ready answer to that question, and that will be the end of it.
Many entrepreneurs believe that informational returns necessarily reflect income (profits) but this is not the case. For example, a 1099-K reflects total volume of payments, which isn’t even close to a business’ taxable income—they still have to pay expenses, etc. The IRS will expect that number to be a subset of one’s revenue for the year (and will ask for an explanation if you show $200,000 of credit card payments but only claim $120,000 of revenue), but they don’t tax revenue, they tax the profits of the business.
What is transfer pricing?
Companies are increasingly doing business internationally, and this raises thorny questions on where related parties working in concert are generating the profits in their business and where it should be taxed. This is also true of many Atlas customers, who might have one corporate entity in the U.S. and one in their home country.
Businesses document movement of money between their own international operations using transfer pricing, a mechanism to describe the internal movements of money, goods, services, and profits between two or more related parties as if they were the “arms-length” dealings of unrelated companies.
Transfer pricing has developed over the years as companies and tax authorities try to tackle the complexities of international business. It is a tool for taxpayers to consider the best way to allocate that income and for tax authorities to consider if too much or too little has been allocated to a territory, especially when there is a difference in the tax treatment between the territories.
The general theory of transfer pricing is that the entities mutually agree on a fair price for goods/services moving between them, record their justification, and have the books of the separate entities match this stipulated-upon reality and also match the actual flow of funds.
In general, market-based economies assume that there is no such thing as a “fair price” except in the context of an agreement between a buyer and a seller. How much “should” software cost? Nothing, or $0.99, or a million dollars a year, depending on the agreement between the parties. Authorities treat the choice of a buyer and seller to agree on a price with substantial deference, including in tax matters—the IRS will default to assuming that the price of an expense item is reasonable.
There is a caveat here which is very important for transfer pricing: we assume that the buyers and sellers in most transactions are doing the transaction because they like the terms of the transaction, not because they have a relationship larger than the transaction. This is called dealing “at arms length.” When the buyer and seller are related to each other, for example by being married or by being under common corporate control, the transaction could conceivably be influenced by their desire to not end up sleeping on the couch. Or, more worrisomely from the IRS’ perspective, to reduce tax paid.
Accordingly, transfer pricing is about documenting “In the hypothetical world where our two companies were not related to each other at all, we could have reasonably agreed to buy this thing because it is valuable, and to pay this amount of money because that is what this thing would cost on the market.”
Transfer pricing examples
Two examples which are common among Atlas companies:
Sales of software through the U.S. subsidiary of a foreign company:
Suppose we have the founders of a software company which operates in India as a Private Limited Company (PLC), the Indian equivalent of a U.S. C corporation. We’ll call it server monitoring software, for concreteness.
The PLC sells server monitoring software directly to Indian companies, but its software is usable by customers worldwide. They establish a Delaware C corporation as a subsidiary to sell their software to customers worldwide, while they intend the PLC to continue selling to domestic Indian customers.
In this case, the ultimate economic goal of the enterprise is to allocate much of the profits to where the value creation happens, which, since the software is actually produced in India, should be India. This will let the Indian PLC pay its expenses (including payroll for the engineering team), compensate the founders, and produce profits which will go to the founders or (likely local) investors. The enterprise accordingly wants to leave an amount in the U.S. entity proportionate to the work performed by it.
There are a variety of ways to accomplish this. One is by making the U.S. entity a reseller of the PLC’s software. The company will exhaustively document that they researched reseller arrangements. Let’s assume, hypothetically, that the result of this research was that unrelated resellers typically received 20%. They will then have the U.S. entity sign a formal reseller agreement with the PLC, obligating it to pay 80% of the billings it charges customers for the software that the PLC developed.
That fee enters the Indian PLC as revenue, after which it is netted against the expenses (payroll, servers, etc) of the Indian entity and taxed by India.
The remaining 20% of sales stay in the U.S. corporation. The business applies some of them to the required costs to operate the U.S. corporation, such as accounting fees, lawyer fees (for contract negotiation, etc), bank fees, and the like. This will result in the U.S. entity earning a modest profit; that profit is taxed by the United States. The post-tax profit can be sent to the C corporation’s parent company, where it may or may not be taxed, or it can be kept in the U.S. for the time being, to be later deployed in e.g. expanding the U.S. operation, purchasing U.S.-based assets on the behalf of the U.S. company, or similar.
Sales of physical products through a U.S. company taking investment:
Suppose we have founders in Hong Kong who make iPhone cases locally, with the intention of distributing them internationally. They might choose to take investment. If their investors are from Silicon Valley, their investors will likely require them to establish a Delaware C corporation to invest in.
In this case, the ultimate goal of the enterprise is to first transfer funds from the United States to Hong Kong, use those funds to establish a manufacturing operation, and then sell the products of their operation through the U.S. entity.
The first part of this would be the U.S. entity contracting with the company in Hong Kong for professional services—design, branding, etc. This would provide adequate justification for paying the company enough money to get up and running. This is recorded as revenue by the Hong Kong company and an expense by the U.S. company.
The operation in Hong Kong then begins producing iPhone cases. It will sell them to the U.S. company, which will sell them worldwide. Here, the company would prefer to sell them at the lowest possible price (because that raises the profits of the U.S. entity, which will please the U.S. investors), but compliance considerations will have them pricing in line with other manufacturers of goods sold at retail in the U.S. It could, for example, end up that the wholesale price (paid by the U.S. company to Hong Kong company) would be 40% of retail. The company would, again, exhaustively document their rationale for this pricing, and show it on invoices/bills of shipping/etc between the two companies.
This will likely leave the Hong Kong company with a modest profit (from services work and iPhone cases sold wholesale, which gets taxed in Hong Kong). The U.S. company will have paid for the services work and wholesale cases, then sold the cases on at a (higher) retail price (through its website or other channel), hopefully earning a profit. The profit is taxed in the U.S.; after taxes, it is possible that dividends would flow to the investors or owners of the company.
Some not-so-obvious observations here:
The company had the choice of selling the cases through the Hong Kong entity or the U.S. entity. Why sell through the U.S. entity? The primary reason will be that the investors are investing in the hopes of owning the value that the company produces, so the company will organize to keep most value in the U.S. entity—it will own the brand, designs, and commercial relationships, and “just” have the Hong Kong entity do the actual work on its behalf.
Would it be safe to run this example in the other direction? It would be markedly riskier. In general, transfer pricing which functions to recognize revenue in high-tax jurisdiction, rather than a low-tax jurisdiction, is not scrutinized very closely. Transfer pricing which functions to recognize the revenue in a low-tax jurisdiction, on the other hand, more often gets thoroughly investigated. The corporate tax rate in Hong Kong is less than half of the rate in the United States; the IRS, accordingly, might assume that a U.S. entity paying a related Hong Kong entity might be doing it for tax optimization purposes rather than for legitimate economic reasons. This doesn’t make it impossible, just harder to justify; one of the reasons to have accountants is to get a good sense of what the risk of a given tax position is and then make a business decision on how much to optimize for tax savings versus tax risk.
Transfer pricing can get very complicated, particularly as corporate structuring gets more complicated, the types of transactions start getting complicated (multi-party multi-nation financial transactions are much harder to account for than simply selling an iPhone case), and the size of the business increases.
An enterprise doing millions of dollars of revenue will likely need to have their transfer pricing strategy designed or redesigned by accountants specializing in their industry. That said, even smaller businesses should document their transfer pricing position; not having documentation would make it very difficult to avoid penalties if the IRS were to examine you and take issue with your transfer pricing.
Enforcement actions disproportionately target larger players (because tax agencies understand that large players are where the money is).
This shouldn’t scare you—the IRS, like most tax agencies, is quite reasonable and simply want to be paid an amount consistent with your responsibilities under the law. If you have a good-faith disagreement with the IRS, it will be resolved in the ordinary course of business, by your professional advisors. This is fairly infrequent and overwhelmingly not likely to be the reason one’s business fails; concentrate your efforts on making something people love and selling it effectively. You can, and should, hire accountants to worry about these sorts of things for you.
“Audits” are a scary word for many entrepreneurs. They shouldn’t be.
An audit is simply a formal inquiry by a taxation agency into the correctness of information on your tax return. The overwhelming majority of audits are “correspondence audits”—the tax agency simply sends you a letter, generally because a computer compared informational returns to your filed tax return and noted a possible discrepancy. Your response to correspondence audits will generally be written by your accountant, but it is likely to be relatively simple. (Often, the issue can be explained away in a single paragraph.)
The IRS will sometimes select returns for more detailed examination. You should absolutely, positively have professional representation if selected for one of these audits; they can be quite stressful and distracting from running the business, even though they are—if you are filing accurate returns from a well-organized business—not an emergency.
These audits will generally require an in-person visit, either at the IRS’ local office or at your office. (The IRS maintains offices in U.S. embassies worldwide for the purpose of international taxation issues. Their staff are typically small so they have to be very selective in audit activity, but you should nonetheless file accurate returns in a timely fashion.)
In the event of an audit, your accountant or tax attorney will instruct you as to your response. You should follow their advice to the letter; this is what you’re paying them for. Some things which naively might seem like a great idea, like providing the IRS with all financial data from your business, may delay the resolution of the audit or overly complicate things, for example by causing examination of parts of the business that were not originally in the scope of the audit.
Audits are rare, particularly of smaller companies. You should know that they are a possibility if you run a business, but they are just that—a possibility at a relatively routine encounter between your business and the government. You should treat the possibility like a responsible professional: hire an accountant, file honest returns, retain information in an organized fashion, and spend your time worrying about growing the business rather than worrying about the unlikely event of an audit. Should you actually be audited, you will again treat it like a responsible professional: call in your accountant/tax attorney and follow their instructions.
Tax is a moving target
Accounting is a deep field, much like software development or marketing. One similarity is that the core of the profession is fundamentally the same from year to year. Another similarity is that things still change, constantly.
There is a worldwide interest in tax reform right now. Tax agencies are still wrangling with getting their heads around the internet, and consequential changes affecting the positions of internet businesses could happen at any time.
Just like you wouldn’t set your marketing or technical strategy once and then forget it, you’ll want to work with your tax advisors on (minimally) a yearly basis to ensure that the way you have structured things is still compliant and still in your best interests.
Sometimes you’ll even get unexpected good news! For example, when the author of this guide started his business, he was double-taxed by the social security systems of two countries on the same income. A few years into the business, they signed a Totalization Agreement, which allowed him (and similarly situated businesses) to pay only to the system of their country of residence. This was a material savings, available due to a change in law, which he would have missed had he not routinely reviewed his tax strategy with a professional.Volver a las guías