Equity compensation
RSUs, ISOs, NSOs, ESPPs, PSUs, and QSBS: the mechanics, the taxes, and the planning. Every piece here is written for someone whose biggest financial decision this year involves a vesting event or a strike price.
How the IRS treats restricted token units, airdrops, and staking rewards in employment comp, and the planning moves that stop the paper-gain trap.
How to think about the real value of pre-IPO options, RSUs, and common stock when there is no market price and the company might not IPO.
A working guide to Rule 10b5-1 selling plans, the 2023 cooling-off period, and how to build a plan that actually executes when you want to sell.
All articles
- Crypto and Token Compensation: Tax Treatment and Planning
How the IRS treats restricted token units, airdrops, and staking rewards in employment comp, and the planning moves that stop the paper-gain trap.
- Pre-IPO Equity: What's Actually Worth Something Before a Liquidity Event
How to think about the real value of pre-IPO options, RSUs, and common stock when there is no market price and the company might not IPO.
- 10b5-1 Plans: How to Set One Up Before You Need One
A working guide to Rule 10b5-1 selling plans, the 2023 cooling-off period, and how to build a plan that actually executes when you want to sell.
- The Complete RSU Guide: Vesting, Taxes, and What to Do at Each Vest
What actually happens when your restricted stock units vest, how much tax you owe, and the sell-or-hold decision you have to make every quarter.
- Exit Planning: The 18 Months Before a Liquidity Event
What founders and executives should do in the year and a half before an IPO, acquisition, or major secondary to preserve the maximum after-tax outcome.
- QSBS and Section 1202: The $10M Federal Exclusion Every Founder Should Know
How the qualified small business stock rules work, who qualifies, how to stack the exclusion across trusts, and what blows up the eligibility.
- ESPP Maximization: The Math on a Qualified 15% Discount with Lookback
Why a standard Section 423 ESPP is the highest risk-adjusted return in your comp package, and how to capture the full discount without holding forever.
- Founder Equity: 83(b) Elections, QSBS, and Early Exercise
The three moves every founder should make in the first 30 days after incorporation, plus the common mistakes that permanently destroy future tax savings.
- Secondary Market Sales and Tender Offers: A Practical Guide
How private-company secondaries actually work, the ROFR and transfer-restriction landmines, and what sellers should expect on price, tax, and timing.
- 409A Valuations Explained for Employees Getting NSO Grants
What the 409A is, why it sets your option strike price, how it changes over time, and the specific 409A numbers that should influence when you exercise.
- NSO vs ISO: When Each Comes Out Ahead for Tech Employees
The real tradeoff between non-qualified and incentive stock options, with after-tax comparisons across company stage, strike price, and holder tax bracket.