Tender Offer Tax: How Selling Private Shares Is Taxed
How tender offer proceeds are taxed: capital gains on long-held shares, ordinary income above your 409A price, plus FICA and AMT traps for ISO, NSO, and RSU sellers.
Mike Navarro··12 min read
Tax planning for equity compensation — estimated payments, exercise timing, multi-year strategies, and practical guides to minimize your total tax liability.
28 articles
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AMT is driven by the ISO bargain element, so the way to avoid triggering it is to control that number — exercise to your break-even, spread exercises across years, and time disqualifying sales. Here are the levers in dollars.
A complete guide to ESPP taxes — the discount taxed as ordinary income, the capital gain at sale, qualifying vs. disqualifying dispositions, and the broker basis trap that double-taxes the unwary.
Four quiet leaks — under-withholding, the broker basis trap, bunched income, and unplanned AMT — drain thousands a year from equity-comp holders who never see them coming. Here's how much each costs, and how to plug them.
QSBS exclusion rules under §1202 can wipe out federal tax on up to $10M (now $15M) of startup-stock gain after a 5-year hold. See the eligibility tests, the cap, and the 2025 OBBBA changes.
Bunching an ISO exercise or a big share sale into one year stacks your income into the top bracket and past the AMT break-even. Here's how to optimize equity taxes across multiple years by flattening income instead.
ESPP tax examples worked in dollars: the 15% discount as ordinary income, the qualifying vs. disqualifying split, the broker basis trap, and the W-2 reporting — all on one set of shares.
Optimize ISO exercise timing across 3-5 years