Pathfinding Consultants

If you own an LLC — or you’re about to form one — here’s a question that trips up more business owners than almost any other: how is an LLC taxed? Most people assume “LLC” is its own tax category, the way a corporation is. It isn’t. The IRS does not have an “LLC” box on any tax return. An LLC is a state-law entity, and the IRS taxes it as something else entirely — a sole proprietor, a partnership, or a corporation — depending on how many owners it has and what elections it ma

Here is a tax outcome that shocks investors every year: someone loses money in the market — real money — and still ends up owing tax on a large capital gain. How is that possible? The answer is almost always the same: the wash sale rule. Active investors who sell at a loss and buy the same investment back too quickly can have their losses DISALLOWED, while their gains remain fully taxable. The result can be a tax bill on a 'phantom gain' — a gain that exists on the tax return

If you waited tables, tended bar, styled hair, or worked any tipped job in 2025 — and you have not yet completed your tax filing 2025 — there is a new deduction you should know about before you file. The One, Big, Beautiful Bill Act created a 'no tax on tips' deduction, and 2025 is the first year it applies. For an eligible tipped worker, this tip income deduction can mean deducting a meaningful amount of tip income from federal taxable income. But the rules are specific: not

If you worked overtime in 2025 and have not yet completed your tax filing 2025, there is a new tax deduction you should know about. The One, Big, Beautiful Bill Act created a deduction often called 'no tax on overtime,' and the IRS has now issued the rules for claiming it on 2025 returns. The headline is appealing — but the actual rules are detailed, and the deduction is narrower than the nickname suggests. This article brings together what the IRS has published so you unders

Cost segregation is one of the most talked-about tax strategies in real estate — and one of the most oversold. Done right, on the right property, it can move a large amount of depreciation into the early years of ownership and meaningfully reduce taxable income. Done on the wrong property, or by an owner who cannot actually use the deductions, it can cost thousands in study fees for little or no be nefit. This complete guide explains what cost segregation is, how a cost segre

The business mileage deduction is one of the most valuable write-offs available to business owners who drive for work — and one of the most frequently disallowed in an audit. The reason is almost never that the miles were not driven. It is that the business owner could not PROVE them. The IRS holds vehicle deductions to a strict documentation standard, and a deduction you cannot substantiate is a deduction you lose, no matter how legitimate. This guide explains how the busine

An envelope from the IRS lands on your desk, and your stomach drops. Take a breath — receiving an IRS notice or IRS letter is far more common, and far more routine, than most business owners realize. The IRS sends millions of notices every year, and the large majority are simple matters: a math correction, a balance due, a request for a document, or a mismatch between what you reported and what a third party reported. What matters is not that you received the IRS letter — it

Every year, business owners reach their business tax deadline without the documents, the bookkeeping, or the time they need to file an accurate return. The good news: the IRS lets you buy more time, almost automatically, with a single one-page tax filing extension. The catch — and it is a big one — is that a business tax extension buys you more time to FILE, not more time to PAY. Misunderstanding that one distinction is the most expensive mistake business owners make at their

Few things put a business owner on edge faster than an envelope from the IRS marked "examination." But a business tax audit is not an accusation, and it is not the end of the world — it is a process, and like any process, it has rules, rights, and a defined path. The business owners who fare best in a business tax audit are almost always the ones who understand that process and have professional IRS representation handling it on their behalf. This guide explains what actually

If you own a business or earn self-employment income, the IRS does not wait until April to collect your tax. It expects you to pay as you go, through quarterly estimated tax payments spread across the year. Miss a payment, or pay too little, and the IRS charges an underpayment penalty under Internal Revenue Code Section 6654 — a cost that is entirely preventable with proper planning. This guide explains how quarterly estimated tax works for business owners in 2026: who has to