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·June 24, 2026·12 min read

#Tender Offer#Secondary Sale#ISO+5 more

ISO vs NSO: Tax Differences, AMT Risk, and Which Is Better for You

A detailed comparison of Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs) covering tax treatment at exercise and sale, AMT implications, the $100K annual limit, and holding period requirements.

Mike Navarro·April 4, 2026·13 min read

#ISO#NSO#Stock Options+2 more

Disqualifying Disposition: What Happens When You Sell ISOs Early (and When It's Smart)

A disqualifying disposition is selling ISO shares before meeting the holding period. Learn the two requirements, tax consequences, and when selling early is actually the better strategy.

Mike Navarro·April 4, 2026·11 min read

#ISO#Stock Options#Tax Planning+1 more

Strike Price (Exercise Price): What It Is, How It's Set, and Why It Matters

Your strike price determines your profit when exercising stock options. Learn how companies set it, the role of 409A valuations, what happens when options go underwater, and the tax implications.

Mike Navarro·April 4, 2026·10 min read

#Stock Options#ISO#NSO+1 more

Stock Options Tax Calculator: ISO and NSO Tax Impact Compared

Compare the tax impact of exercising ISOs vs NSOs with our free stock options tax calculator. See how exercise timing, holding periods, and AMT affect your bottom line.

Mike Navarro·March 11, 2026·8 min read

#Stock Options#ISO#NSO+3 more

IPO Lock-Up Period: What Happens to Your Shares and Tax Strategy

During a 180-day IPO lock-up, you can't sell shares but may still owe taxes. Learn about the liquidity gap, 5 financing options, and how to plan ahead.

Mike Navarro·March 11, 2026·8 min read

#IPO#Lock-Up Period#Liquidity+2 more

When to Exercise Stock Options: Timing Strategies for Maximum Value

The timing of your stock option exercise can save or cost you hundreds of thousands in taxes. Compare 4 exercise timing strategies with concrete examples.

Mike Navarro·March 11, 2026·9 min read

#Stock Options#Exercise Timing#ISO+2 more

Exercise Stock Options Before IPO: Tax Implications and Strategy Guide

Should you exercise stock options before your company goes public? This guide covers the tax implications of pre-IPO exercises, 83(b) elections, AMT planning, and multi-year strategies.

Mike Navarro·March 11, 2026·8 min read

#IPO#ISO#Stock Options+3 more

Estimated Tax Payments After ISO Exercise: Avoid the AMT Penalty

ISO exercises can trigger AMT estimated tax requirements. Learn safe harbor rules, quarterly payment deadlines, and how to avoid the IRS underpayment penalty.

Mike Navarro·March 11, 2026·10 min read

#ISO#AMT#Estimated Taxes+2 more