ESPP Tax Treatment: Qualified vs. Disqualifying Dispositions Explained
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.
ISO vs NQSO: Stock Option Tax Treatment Every Tech Worker Needs to Understand
Incentive Stock Options and Non-Qualified Stock Options trigger taxes at different events and rates. This guide covers the AMT trap, qualifying vs. disqualifying dispositions, the $100,000 ISO vesting limit, and eight strategies tech workers use to lower the tax bill on equity compensation.
Section 1244 Stock: How Failed Startup Investors Can Deduct Up to $100,000 as Ordinary Loss
Section 1244 of the Internal Revenue Code lets qualifying small business stock losses be deducted as ordinary losses up to $50,000 per year for single filers and $100,000 for joint filers, bypassing the $3,000 annual cap on capital losses. This guide covers the corporate and shareholder requirements, how to claim the loss on Form 4797, and the documentation traps that disqualify ordinary-loss claims.
S Corp Shareholder Basis: The Complete Guide to Tracking and Protecting Your Deductions
S corp basis determines how much of your losses you can deduct and when distributions become taxable. This guide covers stock basis vs. debt basis calculations, Form 7203 requirements, the order of adjustments prescribed by the IRS, and five common mistakes that permanently cost shareholders thousands in disallowed deductions.
S Corp Stock Basis—A Practical Guide for Founders (with Beancount.io examples)
Understanding shareholder basis is crucial for S corporation founders. This guide clarifies what basis means, its impact on tax deductions, and how to effectively track it using Beancount.io.