Articles · Frameworks · Substantive Strategy
Resources for entrepreneurs.
Working frameworks, not generic tax tips. Each article reflects how we actually think about the question — what we’d tell a client in a strategy session, written down. Published when we have something useful to say, not on a content calendar.
Latest articles
Do You Need to Send a 1099 for 2026? The New $2,000 Threshold, Explained
For 2026 payments, Form 1099-NEC and most 1099-MISC boxes start at $2,000. What changed, the thresholds that didn’t, and the February 1, 2027 deadline.
Read article → DepreciationThe “G-Wagon Loophole” in 2026: What a Heavy-SUV Write-Off Actually Requires
A heavy SUV can be fully expensed in year one, but only the business share, only above 50% business use and only once it’s in service. The 2026 and 2027 limits and the traps.
Read article → Trump AccountsCan My Business Put $2,500 in My Kids’ Trump Accounts? What the Proposed Rules Say
The $2,500 employer contribution isn’t available to most owners for their own children under the August 2026 proposed rules. Who qualifies, the payroll-tax catch and what employers can offer.
Read article → Health CoverageSelf-Employed on ACA Marketplace Insurance? What Changed for 2026 and 2027 Coverage
The 400% income cliff is back and excess advance credits are now repaid in full. The 2027 numbers, a worked example and the year-end moves that lower the bill.
Read article → S-Corp StrategyIs the Augusta Rule Legit? Renting Your Home to Your Business, Without the TikTok Version
Section 280A(g) is real, but the company’s deduction is where it fails. What the Tax Court allowed in Sinopoli and Jadhav, and the year-end steps that make it hold up.
Read article → IRS NoticesIRS Notice CP14, CP2000, or CP504? What Each One Means
Got a notice and not sure how serious it is? What CP14, CP2000, and CP504 each mean, the deadline on every one, and when a notice needs an attorney with IRS representation rights.
Read article → Entity SelectionLLC vs. S-Corp vs. C-Corp: How to Choose Your Business Entity
The legal form and the tax election are two decisions, not one — a working framework for choosing between an LLC, an S-Corp election, a C-Corp, and a partnership.
Read article → AccountingQuickBooks Cleanup: How to Get Your Books Tax-Ready
Cleanup done in the wrong order wastes hours. The order of operations we use to turn a broken QuickBooks file into books you can actually trust.
Read article → NonprofitForm 1023 vs. 1023-EZ: Which 501(c)(3) Application You Need
The streamlined 1023-EZ is faster — but only if you qualify. How to choose between the full Form 1023 and the EZ, and why the wrong choice is expensive to unwind.
Read article → StrategyTax Planning vs. Tax Preparation: Why the Distinction Matters
Most entrepreneurs hire a tax preparer when what they need is a tax planner. The two jobs are different in nature, timing, and value — and most leave significant savings on the table because they confuse them.
Read article → S-Corp StrategyS-Corp Tax Optimization: Reasonable Comp, Distributions, and the Strategy That Holds Up
The S-Corp election is the single most-leveraged structural move for many small business owners — and the most-mishandled. The savings depend on getting reasonable compensation right, and most owners are flying blind.
Read article → Fractional CFOWhen to Hire a Fractional CFO (and When You Don’t Need One)
Fractional CFO is a service category that ranges from glorified bookkeeping to actual financial leadership. Here’s how to tell which one you’re buying, when each makes sense, and how to evaluate whether you need one at all.
Read article → ChecklistYear-End Tax Planning Checklist for Business Owners
The moves you can still make in October, November, and December — and the ones that can’t happen after year-end. A working checklist organized by deadline, not by tax topic.
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