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
How to Avoid Triggering AMT on Your ISO Exercise
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.
Mike Navarro··7 min read
How to Optimize Your Equity Taxes Across Multiple Years
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.
Mike Navarro··7 min read
ESPP Taxes: How Employee Stock Purchase Plans Are Taxed
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.
Mike Navarro··12 min read
#ESPP#Employee Stock Purchase Plan#Qualifying Disposition+3 more
Double-Trigger RSU Tax: How Private-Company RSUs Get Taxed at a Liquidity Event
Double-trigger RSUs are taxed as ordinary income at the liquidity event, not at vest. Here's why 22% withholding rarely covers the bill, with worked examples and a financing plan.
Mike Navarro··9 min read
QSBS Exclusion Rules: Section 1202 Eligibility, Holding Period & Caps
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.
Mike Navarro··13 min read
#QSBS#Section 1202#Startup Equity+3 more
How Much You're Losing on Your Equity Comp Taxes
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.
Mike Navarro··7 min read
ESPP Tax Calculator: Estimate Your Tax on the Discount and Sale
An ESPP tax calculator estimates two layers of tax: ordinary income on the purchase discount and capital gains at sale. Model qualifying vs. disqualifying dispositions in dollars.
Mike Navarro··9 min read
ESPP Tax Examples: Worked Numbers for Qualifying vs. Disqualifying Sales
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.
Mike Navarro··9 min read
Best RSU Tax Calculators & Equity Comp Tools (2026)
The best RSU tax calculators and equity comp tools in 2026, compared honestly by price, what they calculate, equity types, state coverage, and signup.
Mike Navarro··12 min read
Google RSU Guide: GSU Vesting Schedule, Taxes, and Strategies
How Google RSUs (GSUs) work — the 1-year cliff, monthly vesting, refresh grants, sell-to-cover defaults, and tax strategies for managing bracket creep.
Mike Navarro··10 min read