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Section 174 R&D Expensing in 2026: How Software Startups Recover From the TCJA Capitalization Trap

OBBBA's new Section 174A restores immediate expensing for domestic R&D in tax years after December 31, 2024, and qualifying small businesses can amend 2022–2024 returns by July 6, 2026 to recover overpaid tax. A guide to the three coexisting Section 174 regimes, the Section 41 credit add-back, foreign 15-year amortization, and the statement in lieu of Form 3115.

Section 409A: Structuring Bonuses, Severance, and Phantom Equity to Avoid the 20% Penalty

Section 409A taxes noncompliant deferred compensation in the year of vesting and adds a flat 20% federal penalty plus interest. This guide explains the short-term deferral and separation pay exceptions, the six recognized payout triggers, the six-month delay for specified employees, and how to structure bonuses, severance, RSUs, phantom stock, and discounted stock options so founders avoid the penalty.

Regulation D Rule 506(b) vs Rule 506(c): How Founders Pick Between the Quiet Round and the Public Pitch in 2026

Rule 506(b) and Rule 506(c) of Regulation D both allow uncapped private placements but differ sharply on marketing and verification. 506(b) bans general solicitation and permits up to 35 sophisticated non-accredited investors on a reasonable-belief standard; 506(c) permits public solicitation but requires reasonable steps to verify every purchaser is accredited. A March 2025 SEC no-action letter lets issuers rely on $200,000+ individual or $1 million+ entity minimum checks as the primary verification step.

Section 382 NOL Limitation After Ownership Change: How Venture-Backed Startups Preserve Net Operating Loss Carryforwards Through Equity Rounds

Section 382 caps a startup's pre-ownership-change net operating loss deductions at the pre-change fair market value multiplied by the long-term tax-exempt rate (about 3.56 percent in February 2026), triggered when 5 percent shareholders collectively gain more than 50 percentage points over a rolling three-year testing period.

Section 83(i) Tax Deferral on Private Company Stock: A Five-Year Lifeline for Pre-IPO Employees with RSUs and NSOs

Section 83(i) lets qualified employees of qualified private companies defer federal income tax on RSU settlements and NSO exercises for up to five years. The 80 percent grant rule, mandatory escrow, and 30-day election deadline explain why adoption stays in the single digits — and when the election still pays off.

The ISO AMT Trap in 2026: How Tech Employees Get Hit With Six-Figure Tax Bills on Stock They Can't Sell

Exercising and holding ISOs adds the bargain element to AMTI on Form 6251 Line 2i, which can produce a six-figure tax bill before a single share is sold. A 2026 guide to the tightened AMT exemption phase-out ($500K single / $1M MFJ at 50¢ per dollar), the qualifying disposition rules under IRC §422, and the planning moves — AMT crossover exercise, §83(b) early exercise, same-year disqualifying sale, and multi-year laddering — that keep tech employees out of the trap.

ISO AMT in 2026: Bargain Element, Form 6251 Line 2i, and the OBBBA Phase-Out Cliff

Under OBBBA, the 2026 AMT exemption phases out at $500K single / $1M joint with a 50-cent rate, doubling the stealth bracket on ISO exercises. Here is exactly how the bargain element flows into Form 6251 line 2i, when a same-year disqualifying disposition eliminates the AMT adjustment, and how to plan exercises to avoid a six-figure phantom-income tax bill.