Tax & Business Insights

When do you have to set up payroll? Before the first paycheck, which in practice means before your employee’s first day of work, and the safe plan is to start four or more weeks ahead. The first paycheck lands on a fixed date. Your federal tax ID and state accounts have to exist before it, […]

A low payroll quote usually covers one thing: calculating paychecks. Year-end forms, extra states, corrections, and the penalty for a late deposit show up on the bill later. We don’t run payroll, and we never have. For years, when clients need a payroll specialist, we’ve sent them to Jen Stevenson at Jen Stevenson Payroll. Our […]

The mortgage interest deduction can still save high earners thousands of dollars in federal taxes, but the amount you can claim depends on more than your mortgage balance. The $750,000 debt limit, the rules for HELOCs and second homes, and the new 2/37 limitation on itemized deductions from 2026 all affect how much interest you […]

Is the IRS out to get small businesses? No. But if you’re a sole proprietor or you report business income on Schedule C, the published data says you have drawn more scrutiny than comparable nonbusiness filers. Does the IRS being about 27% smaller than it was at the start of 2025 mean you can worry less? […]

Student loan payments are one of the heaviest monthly bills for a lot of people, so it’s natural to wonder whether your business could just pick them up. It can, and there’s a tax-free way to do it that Congress made permanent in 2025. The catch is that the rules treat owners and employees very […]

When you work for yourself, clients normally don’t withhold tax from your pay. You can owe two different federal taxes, self-employment tax and income tax, and the IRS expects you to pay them during the year, not just in April. This guide shows how much a freelancer owes in 2026 at different income levels, how […]

Cash basis and accrual basis do not change how much your business earns. They change which year the income and deductions land in, and that timing is what sets your tax bill in any given year. Most small businesses get to choose, and plenty are on accrual only because someone set them up that way […]

TL;DR A mega backdoor Roth runs through a Solo 401(k) rather than an IRA, so the ceiling for 2026 is the $72,000 annual additions limit instead of the $7,500 IRA contribution limit. Your after-tax room is $72,000, or your full compensation if that is smaller, minus your elective deferrals of up to $24,500 and minus […]

If your income is too high for a direct Roth IRA contribution, the backdoor Roth IRA is still one of the cleanest ways to get money into Roth space in 2026. But it is also one of the most misunderstood tax moves I see. The basic idea is simple. The execution is where people create […]

TL;DR Since South Dakota v. Wayfair (2018), a state can require you to register and collect its sales tax even if you have no office, employees, or inventory there. Most states set the threshold at about $100,000 a year, some add a 200-transaction test, California and Texas use $500,000, and Connecticut and New York make […]

TL;DR What decides a legal fee is where the matter came from, not what the invoice says or who wrote the check. In United States v. Gilmore (1963), the Supreme Court called a divorce lawyer’s bill personal even though the fight put three car dealerships at risk. Contract disputes, collections, business tax advice, audit defense, […]

TL;DR Virginia’s 2026 standard deduction is $8,750 for single filers and $17,500 for married couples filing jointly, against a federal $16,100 and $32,200. Virginia makes you match your federal choice, so if you itemize on your federal return you have to itemize on your Virginia return. Virginia removes your Virginia income tax from itemized deductions, […]

Booking an Airbnb instead of a hotel does not change the tax answer. For federal tax purposes, it is lodging. What matters is why you were there. If you traveled away from your tax home (generally the area of your main place of business, not necessarily where you live) for a genuine business purpose, the […]

If you’re trying to decide whether to pay someone on a 1099 or a W-2, the first thing to know is this: you do not simply choose the form you prefer. The real question is whether the worker is legally an independent contractor or an employee. Once that classification is correct, the tax form follows. […]

If you run a small business from home, tax deductions can make a real difference. But this area gets confusing fast. People mix up remote work with self-employment, assume every home expense becomes deductible, or focus so heavily on the home-office deduction that they miss the broader list of ordinary business write-offs. This guide covers […]

If you are buying or selling a closely held business, the headline price is only part of the deal. A transaction can be structured as an asset sale or a stock or equity sale, and that choice changes liability exposure, tax character, basis recovery, required consents, and the seller’s after-tax proceeds. Buyers often prefer asset […]

If your accountant is slow to respond, repeatedly misses important details, or only appears when a tax return is due, changing firms may be the right move. Switching accountants can often be managed without major disruption when records, system access, unfinished work, and upcoming deadlines are addressed deliberately. In this guide, we’ll explain when it […]

Business travel expenses are not automatically deductible just because the trip involved work. The IRS distinguishes between personal commuting, local business transportation, and travel away from your tax home, and each category follows different rules. In this guide, we’ll explain which small business travel expenses qualify, how mixed business and personal trips are handled, and […]

If you run a business in Virginia, one of the easiest ways to make an expensive mistake is to assume there is just one “Virginia business tax.” There isn’t. Virginia businesses can face state income tax, tax on income passed through to their owners, optional pass-through entity tax, local BPOL tax, and Virginia SCC filing […]

If you run an online business, you have probably heard the same advice repeatedly: incorporate in Delaware, form your LLC in Wyoming, or use Nevada to save taxes. In most cases, that advice is incomplete at best and expensive at worst. The right state to form an online business is generally much simpler than the […]

If you’re hoping to write off cosmetic surgery on your taxes, the short answer is usually no. The IRS generally treats elective cosmetic procedures as personal expenses, which means they are not deductible as a business expense and usually not deductible as a medical expense either. The normal path to a deduction is documented medical […]

If you earn income online, you do not automatically need a CPA. But the decision should not be based only on whether your business feels simple or whether tax software can technically produce a filed return. A creator with modest profit, clean records, and limited income sources may be able to handle taxes and bookkeeping […]

If you’re an influencer, a YouTuber or any content creator making your first affiliate sale, small brand fee, or AdSense payout, you probably do not need to rush out and form an LLC tomorrow. But once your content starts looking like a real business – with contracts, recurring income, products, contractors, events, or higher-risk content […]

If you expect to owe substantial Virginia income tax, buying Virginia Land Preservation Tax Credits can reduce that liability at a discount. The opportunity is legitimate, but it is not a simple “buy a credit and save money” transaction. Annual use limits, transfer timing, carryforward rules, appraisal risk, federal tax treatment, and the seller’s documentation […]