#tax-planning
Strategic tax planning to minimize liability and maximize savings
How an ESOP lets founders exit on their own terms — 6,411 US ESOPs hold $2.1 trillion for 15.1 million employees. Covers Section 1042 capital gains deferral, the S-corp federal tax exemption, 2–4% deal costs, fiduciary and repurchase obligations, and which businesses actually fit the structure.
Late Schedule K-1s are the norm, not the exception — a Form 7004 extension pushes partnership and S-corp returns, and every K-1 tied to them, to September 15, a full five months past the April 15 personal deadline. The fix is a simple playbook, file Form 4868, pay at least 90% of a good-faith estimate, and amend with Form 1040-X once the real numbers arrive.
A cash balance plan is an IRS-qualified defined benefit plan that lets business owners 45 and older stack $75,000 to $290,000 in additional pre-tax retirement contributions on top of a 401(k), with the trade-off being a required multi-year funding commitment and $2,000-$4,000 in annual actuarial administration costs.
An Employee Ownership Trust (EOT) lets a business owner sell to a permanent employee-benefit trust instead of a competitor or private equity firm, costing roughly $30,000-$100,000 to set up versus $150,000+ for an ESOP, though the U.S. still offers no federal tax incentive for EOT sales while Canada made its C$10 million capital gains exemption permanent in June 2026.
Independent music teachers who collect payment directly from students run a Schedule C business subject to 15.3% self-employment tax, must book prepaid lesson packages as deferred revenue rather than income, and face a new $2,000 1099-NEC threshold starting in 2026.
With 100% bonus depreciation permanently restored for equipment placed in service after January 19, 2025 and a $2,560,000 Section 179 cap for 2026, the lease-vs-buy decision now hinges on total cost of ownership, cash flow timing, and how long you'll actually keep the equipment — not just which option gets the bigger write-off.
The One Big Beautiful Bill Act's Section 174A permanently restores immediate tax deduction of domestic software development and R&E costs for tax years beginning after December 31, 2024, reversing the five-year amortization rule that had strained small tech companies' cash flow since 2022.
A walkthrough of the Section 469 seven-day rule, the three realistic material participation tests, and how the One Big Beautiful Bill Act's permanent 100% bonus depreciation lets short-term rental owners offset W-2 income — plus the bookkeeping habits that survive an IRS audit.
A practical guide to surviving California FTB and New York residency audits after moving to Florida, Texas, or Nevada — the domicile and statutory residency tests, day-count documentation, equity compensation traps, and the convenience-of-the-employer rule.
OBBBA Section 71308 and IRS Notice 2026-05 let you pair a Direct Primary Care membership of up to $150/month per adult ($300 family) with an HSA starting January 2026, reclassify all Bronze and Catastrophic marketplace plans as HSA-eligible, and make the telehealth pre-deductible safe harbor permanent. Here is how freelancers, solo S-corp owners, and small employers should stack DPC, marketplace coverage, HSAs, and QSEHRA/ICHRA reimbursements without double-dipping.
The enhanced premium tax credits expired January 1, 2026, restoring the 400% FPL cliff. This guide walks self-employed filers, S-corp owners, freelancers, and early retirees through the 2026 applicable percentage schedule, MAGI levers like Solo 401(k), SEP-IRA, HSA, and Section 162(l), and Form 8962 reconciliation strategies to avoid five-figure repayments.
OBBBA raises the federal SALT cap to $40,400 for 2026 with a 30-cent-per-dollar phase-out above $505,000 MAGI, then reverts to $10,000 in 2030. PTET elections in 36 states remain uncapped and still beat the cap for most high-income pass-through owners. State deadlines, bunching priorities, and the 2030 cliff explained.
