470 tagged with "Tax Planning"
Strategic tax planning to minimize liability and maximize savings
The 30-Day Decision That Can Save Founders Millions: A Plain-English Guide to the Section 83(b) Election
A Section 83(b) election lets founders and early employees pay ordinary income tax today on the full value of restricted stock instead of at each vest. Filed within 30 days on IRS Form 15620, it can convert millions of phantom ordinary income into long-term capital gain and start the QSBS holding clock on day one.
Solo 401(k) vs. SEP-IRA for the Self-Employed: 2026 Limits, the Roth Option, and the Pro-Rata Trap
For the self-employed, a Solo 401(k) often shelters more than double what a SEP-IRA does at the same income — a $90,000 earner can contribute $47,000 vs. $22,500 in 2026. This guide covers the limits, the Roth option, the pro-rata rule, and the December 31 deferral deadline.
Step Transaction Doctrine: How the IRS Collapses Multi-Step Tax Plans
The step transaction doctrine lets the IRS treat a sequence of formally separate steps as one taxable transaction. This guide explains the three tests courts apply — end result, mutual interdependence, and binding commitment — the landmark cases (Gregory v. Helvering, Court Holding, Kimbell-Diamond), the 2026 transactions most exposed (1031 drop-and-swaps, pre-sale entity conversions, gifts before the estate exemption sunset), and the documentation habits that keep multi-step plans defensible.
100% Bonus Depreciation Is Back: How Small Businesses Combine Section 168(k) and Section 179 in 2026 to Write Off Equipment the Year They Buy It
100% bonus depreciation under Section 168(k) is permanent again for property placed in service after January 19, 2025, and Section 179's 2026 limit is $2,560,000. This guide shows how small businesses combine both to deduct equipment the year it is bought, with a worked $1.2M example and the disqualification traps to avoid.
Constructive Receipt and the December 31 Check: Why 'I Didn't Cash It' Won't Save You at Tax Time
A practical guide to the constructive receipt doctrine under Treasury Reg. 1.451-2 — what counts as income in the year you got the check, what doesn't, and which year-end deferral moves actually survive an audit.
De Minimis Safe Harbor: How Small Businesses Expense Equipment Up to $2,500 Without Depreciation
A small business with a written capitalization policy dated before the tax year begins and an annual election attached to its return can deduct tangible property up to $2,500 per item or invoice ($5,000 with an applicable financial statement) under Treas. Reg. §1.263(a)-1(f), skipping depreciation schedules entirely.
Form 8275: How a One-Page Disclosure Defeats the Section 6662 and 6694 Penalties
Form 8275 is a one-page disclosure statement that, when attached to a tax return, can neutralize the 20% Section 6662 accuracy-related penalty and the Section 6694 preparer penalty for gray-area positions that have a reasonable basis.
The NYC Tax Most Freelancers Don't Know Exists Until They Owe It
New York City's 4 percent Unincorporated Business Tax applies to freelancers, consultants, and partnerships with NYC gross receipts above $95,000. A full credit eliminates the tax at $95,000 or less of taxable income, while an S-corp election can move higher earners out of the regime entirely.
Quarterly Estimated Taxes for the Self-Employed in 2026: Safe Harbors, Form 1040-ES, and the Annualized Income Method
A working guide to the 2026 quarterly estimated tax rules for freelancers and self-employed earners — the two IRS safe harbors (90% current year, 100%/110% prior year), the four uneven due dates, Form 1040-ES, the annualized income method for lumpy earners, EFTPS vs Direct Pay, and the mistakes that trigger penalties at the 6–7% federal rate.
Give It Now or Leave It Later? The Basis Trap That Quietly Costs Families Hundreds of Thousands in Capital Gains Tax
Lifetime gifts under IRC Section 1015 carry over the donor's basis, while inheritance under Section 1014 steps it up to fair market value at death — a difference that can shift a family's after-tax outcome by six figures on a single appreciated position under the 2026 $15 million federal exemption.
Section 119 Meals and Lodging for the Convenience of the Employer: How Hospitality, Hospital, and Caretaker Employers Keep On-Premises Housing and Cafeteria Meals Out of Wages
Section 119 lets employers exclude on-premises meals and required-residence lodging from employee wages, with no FICA and no income tax withholding. This guide walks through the convenience-of-the-employer test, the "more than half" safe harbor, qualified campus lodging, the Kowalski cash rule, and what the 2026 Section 274(o) deduction sunset does and does not change.
Section 1248 Deemed Dividend on CFC Stock Sales: A U.S. Shareholder's Guide to E&P, GILTI, and PTEP
Section 1248 recharacterizes part of a U.S. shareholder's gain on the sale of CFC stock as a dividend, capped by the corporation's earnings and profits and reduced by PTEP from GILTI and Subpart F inclusions. This guide explains who is affected, how the lookback works, why corporate sellers can prefer the recharacterization for Section 245A, and how to build a defensible work paper.