Quarterly taxes, deductions, and entity-level taxes explained in plain English for new business owners.
Most new business owners get their first real shock at tax time, not because the rate is a mystery, but because nobody warned them how the timing and the paperwork actually work. Maria spent her first year running a landscaping LLC focused entirely on winning clients and keeping the mowers running. She turned a healthy profit, twenty thousand dollars more than she expected, and assumed the extra would just sit in her account until she filed the following April. Instead she owed a four figure penalty for not paying anything toward that profit along the way, on top of the tax itself. Nothing about her situation was unusual. This module covers the basics so the same thing does not happen to you: what you actually owe, when you owe it, and where a little planning during the year saves real money and stress later. It is an overview, not tax advice. Tax law varies by state and changes most years, so treat this as the map, not the final word for your specific situation, and confirm anything that matters with a CPA or irs.gov before you act on it.
If you are self-employed or run a default-taxed LLC, you pay self-employment tax of 15.3 percent on your net business income: 12.4 percent for Social Security and 2.9 percent for Medicare. A regular employee only pays half that combined rate, 7.65 percent, because their employer quietly pays the other half, and it never shows up on a pay stub as a separate cost. When you are self-employed, there is no separate employer to split it with, so you owe both halves yourself, billed to you directly instead of disappearing before you ever see the money. This is the single most common shock new founders describe: on eighty thousand dollars of net profit, self-employment tax alone runs roughly twelve thousand two hundred forty dollars, before a dollar of income tax is even calculated on top of it. The good news is that half of what you pay in self-employment tax is itself deductible from your income tax, and an S-Corp election can reduce the amount subject to this tax in the first place once your profit is high enough to justify the extra paperwork. For the full mechanics of how that works, including when it actually pays for itself, see S-Corp vs. LLC: Taxes & How Owners Get Paid.
See the self-employment tax difference
Enter a rough annual net profit and a reasonable S-Corp salary to see how much self-employment tax an S-Corp election could save, and roughly where it stops being worth the extra paperwork.
Default LLC — SE tax
$16,955
On the full net profit
S-Corp — FICA on salary
$9,945
$55,000 paid as distributions, FICA-free
Estimated savings
$7,010
per year with S-Corp election
Employees have tax withheld from every paycheck automatically, so by April they have usually already paid in close to what they owe. Self-employed people do not have anyone doing that for them, so the IRS expects you to pay estimated taxes four times a year instead of settling up in one lump sum the following spring. This is the same pay-as-you-go logic behind payroll withholding generally (see the Hiring module): the system is built to collect tax close to when it is earned, and underpaying during the year can trigger a penalty even if you pay the full balance by the April deadline. Jordan, a freelance graphic designer, learned this the expensive way in her second year: she paid her entire tax bill in full, on time, on April 15, exactly like she had as an employee, and still owed a penalty, because the IRS measured whether she had paid enough throughout the year, not just by the deadline.
2026 quarterly estimated tax due dates
| Period covered | Due date | |
|---|---|---|
| Q1 | January to March | April 15 |
| Q2 | April to May | June 15 |
| Q3 | June to August | September 15 |
| Q4 | September to December | January 15 (following year) |
Legitimate business expenses reduce your taxable income, which is why keeping track of them is worth real money, not just tidiness. The common categories most businesses run into are a home office (specific square footage and exclusive use rules apply), the business share of a phone and internet bill, software and subscriptions, business travel, professional development and courses, equipment and tools, advertising, self employed health insurance premiums, and retirement contributions through a SEP-IRA or Solo 401k.
The rule that governs all of it is that an expense has to be ordinary and necessary for your type of business. Ordinary means common and accepted in your industry: a laptop is ordinary for a consultant, a commercial oven is ordinary for a bakery. Necessary means helpful and appropriate for your business, not that it was strictly required to keep the doors open. Tom runs a one person bookkeeping practice and tried to deduct a boat he used maybe twice a year to entertain a couple of clients. That expense fails the test on both counts: a boat is not ordinary for a bookkeeping business, and entertaining two clients twice a year does not make it necessary either. This is a real legal standard the IRS applies whenever a deduction gets questioned, not just a rule of thumb, so the honest question for anything you are about to expense is whether another business owner in your field would recognize it as a normal cost of doing business.
Check your understanding: deductions
A consultant buys a laptop she uses for client work. A separate business owner buys a boat he uses twice a year to entertain two clients. Which purchase is more likely to survive an IRS review as ordinary and necessary?
Different business structures are taxed differently, and the choice has real cash consequences well beyond liability protection, covered in full depth in the Business Structures and S-Corp vs. LLC modules. The short version: a sole proprietor or single-member LLC reports business income directly on Schedule C of their personal return, with no separate business filing at all. A multi-member LLC or partnership files a partnership return, Form 1065, and profit passes through to each partner's personal return in proportion to their ownership. An S-Corp files its own corporate return, Form 1120-S, and its owners are paid a salary, subject to normal payroll tax, plus distributions on top of that salary, which are not. A C-Corp pays corporate tax on its profit first, and then owners pay personal tax again on any dividends they receive from what is left, a pattern known as double taxation. That second layer is exactly why most small businesses that are not raising venture capital or planning to go public avoid the C-Corp structure entirely: the same dollar of profit gets taxed twice before it ever reaches the owner's pocket.
How sales tax varies by state, and when you owe it somewhere you have never set foot
If you sell physical products, or certain services depending on the state, you generally need to collect and remit sales tax. Sales tax is entirely a state (and sometimes city or county) system: there is no federal sales tax and no single national rule to follow. Since a 2018 Supreme Court decision, South Dakota v. Wayfair, states can require you to collect their sales tax even if you have zero physical presence there, once your sales into that state cross a threshold called economic nexus. This is the part that catches online sellers off guard. Priya's e-commerce shop was based entirely in Ohio, with no employees, warehouse, or office anywhere else, and she still ended up owing sales tax in three other states purely because of how much she had shipped there over the year. Physical presence used to be the whole test. Now it is only one of two ways a state can reach you.
What varies by state
Keep business and personal finances completely separate
Use a dedicated business bank account and credit card for everything, from day one, even before you have real revenue. This makes tax time dramatically easier, since every deductible expense is already sitting in one place instead of scattered across a personal account mixed in with groceries and rent. If you are an LLC or corporation, it is also what keeps your liability shield intact (see the Business Structures module for why commingling funds can undo that protection entirely, sometimes with a court finding that the business was never really separate from its owner in the first place). Work with a CPA once your business generates real revenue. A good one routinely saves you more in taxes and avoided mistakes than they cost in fees.
Key Terms
Check your understanding
A single-member LLC and a C-Corp each earn 50,000 dollars in profit and pay every dollar of it out to the owner as a distribution or dividend. Which one results in that profit being taxed twice before it reaches the owner?
An online shop based only in Texas ships enough product into Colorado over the year to cross Colorado's economic nexus threshold, despite never having an employee, warehouse, or office there. What does the shop now need to do?
Which habit does the most to make tax season easier and also helps protect an LLC's or corporation's liability shield?
Ask a question about this lesson or share your take.
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A safe starting point: set aside 25 to 30 percent of every dollar of profit for taxes, and pay that aside amount quarterly. It is easier to get a refund for over setting aside than to scramble for an underpayment penalty.
Do you need to pay quarterly estimated taxes?
Will you owe at least 1,000 dollars in federal tax this year after subtracting any withholding and credits?
Check your understanding: self-employment tax and quarterly payments
Priya's LLC nets 60,000 dollars in profit this year, and she has no other income. Roughly how much will she owe in self-employment tax alone, before any income tax?
A founder pays their entire year's tax bill in full on April 15, the date most people think of as tax day. Can the IRS still charge a penalty?
Tools like TaxJar or Avalara can track your sales by state and flag when you have crossed a nexus threshold automatically, worth adopting early if you sell online across state lines, since manually tracking this against every state's current threshold is genuinely impractical past a handful of states. Each state's department of revenue website is the authoritative source for its current threshold and rules.