Most buyers treat accounting as the cost of keeping score. You close on a business or a property, you hand the books to a bookkeeper, and you check back at tax time. The accounting department becomes a compliance expense. A necessary evil. Overhead. That framing costs you real money. Done right, the accounting function in a newly acquired business or property is one of the highest-ROI investments you'll make in the first year of ownership. It finds revenue you're entitled to but never billed....
12 days ago • 7 min read
IRC §267 disallows losses on sales between related parties. 👪 For older clients sitting on lower value real estate and corresponding capital losses they will never use, §267 has a quieter feature that can move real money to the next generation. This is especially interesting for those subject to estate tax (estate values > $30 million). 🏦 The feature is the "§267(d) offset." When a related-party loss is disallowed, it does not vanish. 💨 It attaches to the property in the buyer's hands. If the...
19 days ago • 5 min read
If you own a business with at least one other person, you have a document that governs how your business runs. Operating Agreement, Partnership Agreement, Shareholder Agreement - all driving the same things: Who can make decisions What happens when things go bad Who gets money when there is money to distribute How does it all get wound up For too many small businesses and real estate GPs, the agreement comes from their attorney and the attorney focuses on the things they're good at - risk....
26 days ago • 6 min read
Tax is hard. Making money doing taxes for others is even harder. That's usually the main driver for the mistakes I find on returns I look at for prospects. Most CPAs understand these basic things, like what we're talking about today - Basis, but they're trying to run a business. And quality is very difficult to scale. So how can you spot check the K1s you get (or prepare) on a partnership return? And what happens if you get it wrong? Glad you asked. 🤝 Why Basis Matters Basis in a partnership...
about 1 month ago • 3 min read
If you were charged penalty and interest for taxes at any point between January 2020 and July 2023, there is a chance the IRS over-assessed and owes you money back, at least for now. 👀 A late-2025 federal court ruling held that the COVID-19 disaster declaration automatically postponed federal tax deadlines for that entire 42-month stretch, and any late-filing penalty, late-payment penalty, or underpayment interest the IRS computed using a "due date" inside that window is potentially...
about 1 month ago • 3 min read
Tax deferral ⌛ let's you compound savings at your business' internal ROI at the cost of the US Treasury. The biggest moves in the tax code work by delaying the tax due. Push the bill into the future and you keep using money the government would otherwise have. It's cheap capital. Here’s the map on major deferral strategies across the lifecycle of a business: Stage 1: Starting the business When you put property into a new company in exchange for stock or partnership units, the tax code treats...
about 2 months ago • 4 min read
📥 After a few DMs, I've tried to fix the sending email to get less SPAM flags. My apologies if you've not seen the email in the last few editions! Always check out the link in my X bio for the latest and greatest if that's you! My apologies - I'm good at tax, not so much at DNS set-ups! When a potential new client hands me a prior year return, I check three spots that are dead giveaways for immediate ROI of my fees. These are the spots that tell on a sloppy preparer (no shade, I've made these...
about 2 months ago • 5 min read
If you own a small business, you have a choice of how to pay tax on business income - accrual or cash. Accrual is where the big boys play (revenue over $30mm) as it's more accurate. But for tax purposes, an accrual basis tax return isn’t entirely accrual. Buried in the code are a handful of transaction types that ignore your method of accounting and behave like cash no matter what. Miss them and you either overpay by leaving deductions on the table, or underpay and hope and pray the IRS...
2 months ago • 4 min read
Penalties and interest. An unfortunate part of paying taxes for most small business owners. Taxable income doesn't always align with liquidity ⚖️ in the SMB world, and when given a choice between making payroll and making an estimated income tax payment all business owners pay their people. But today we're going to look at one strategy available for taxpayers to recalculate penalties and interest - with the potential to significantly drop 🔻 or eliminate the late payment penalties. The Basics...
2 months ago • 3 min read