Coming soon · Book Profile
Stock Options Grants Wheeler
A plain-language, question-and-answer guide that teaches executives and employees how equity compensation works and how to make tax-smart, risk-aware decisions about their stock options and grants.
A profile of this book is on the way.
What it’s about
Millions of workers hold stock options and grants they barely understand, leaving vast wealth exposed to needless taxes, concentration risk, and costly timing mistakes. Stock Options + Grants demystifies incentive stock options, nonqualified options, restricted stock, and employee stock purchase plans through an accessible Q&A format that covers the full lifecycle of equity compensation: what these instruments are, why companies grant them, how they are taxed (including the dreaded Alternative Minimum Tax), when and how to exercise, what to do with underwater options, and how options interact with gifting, estate planning, divorce, and insider trading rules. Grounded in real client experience and cautionary true stories from the dot-com collapse, the book champions a disciplined 'Core Capital' planning philosophy over the gambler's temptation to hold company stock hoping for endless gains. Whether you hold twenty shares or several million, this guide equips you to work intelligently with your advisors and maximize the value of a very valuable, very complex asset.
The through-line
- Who it’s for
- An executive or employee who holds stock options or grants and wants to maximize the wealth from their equity compensation.
- The problem
- They hold complex equity compensation with confusing tax rules, restrictions, and timing decisions they don't understand. They feel anxious, uninformed, and afraid of making a costly mistake that squanders a valuable asset.
- The plan
- Learn which type of equity you hold and how it is taxed.
- Understand the tax consequences (including AMT) of exercising and selling.
- Determine your Core Capital and financial goals through a financial plan.
- Develop and follow an exercise, sell, hold, and diversification strategy.
- Address gifting, estate, divorce, and insider considerations with qualified advisors.
- The payoff
- You make tax-smart, well-timed decisions about exercising and selling. · You set aside your Core Capital and diversify to secure your financial future. · You avoid the horror stories of owing taxes on stock that has collapsed in value.
See our guide
Related profiles we’ve built
Additional reading
- IRS and SEC Legal Code (via Cornell Law School Legal Information Institute) · U.S. Government
Provides the primary source for the specific rules governing equity compensation discussed in the book, such as IRC Section 83(b), Section 422 (for ISOs), Section 409A, and SEC Rule 701.
- VentureHacks.com · Nivi and Naval
Cited as a source of 'good advice for startups,' specifically for providing benchmarks on appropriate equity grants for advisors.
- AngelList (angel.co/salaries) · AngelList
Mentioned as a key resource for both founders and employees to research and benchmark typical salary and equity data for various startup roles, ensuring offers are competitive.
- The Open Guide to Equity Compensation · GitHub community (jlevy)
Listed in the end notes as a resource, suggesting it provides more in-depth or community-driven information on the topic.
- Clerky.com · Clerky
Referenced as a provider of streamlined legal documents for startups, including a set of stock plan forms developed in collaboration with Y Combinator and Orrick.
- Crunchbase.com · Crunchbase
Listed in the end notes as a platform for finding business information about private and public companies, useful for general research.
- Founder’s Pocket Guide: Startup Valuation · 1x1 Media (implied)
Expands on a core topic of the cap table guide, covering various valuation methods for arriving at a defensible pre-money valuation.
- Founder’s Pocket Guide: Convertible Debt · 1x1 Media (implied)
Provides details on convertible debt, a funding structure mentioned as a key item to be tracked on a cap table before it converts to equity.
- Founder’s Pocket Guide: Terms Sheets and Preferred Shares · 1x1 Media (implied)
Details the rights, preferences, and protections of preferred shares, which are critical for accurately modeling exit scenarios in more sophisticated cap tables.
- Founder’s Pocket Guide: Stock Options and Vesting · 1x1 Media (implied)
Explains how to structure and track stock options and vesting, which are managed within the option pool recorded on the cap table.