# Make sure your equity generates wealth, not a shocking tax bill. ## Stock options, RSUs, job offers, and taxes—a detailed reference, including hundreds of resources, explained from the ground up, for employees and managers. - **The entire online book** - **364+** links and references - Digital access to this title in the Holloway Reader - Downloadable PDF and EPUB for personal offline use - Newly updated for 2022! **Length:** 80 pages **Edition:** e2.1.1 **Language:** English **ISBN (Holloway.com):** 978-1-952120-03-9 This is the first thing I share when someone is thinking about their equity compensation. — Ryley Reynolds (Thrive Capital) # Table of Contents - Introduction - Scope - Who May Find This Useful - A Note on Fairness - Roadmap - How This Guide Is Organized - When to Turn Elsewhere - Seeking Professional Advice - Equity Compensation Basics - Growth and Risk - Compensation and Equity - The Goals of Equity Compensation - Fundamentals of Stock Corporations - Stock and Shares - Public and Private Companies - Governance - IPOs - Sales and Liquidity - Startups and Growth - Startups - Fundraising, Growth, and Dilution - Dilution Illustrations - Stages of a Startup - The Option Pool - Counting Shares - Classes of Stock - How Equity Is Granted - Restricted Stock Awards - Stock Options - Vesting and Cliffs - How Options Expire - Kinds of Stock Options - Early Exercise - Restricted Stock Units - Using Promissory Notes to Buy Stock - Less Common Types of Equity - Tax Basics - Kinds of Income - Federal Taxes - State Taxes - Taxes on Equity Compensation - 83(b) Elections - 409A Valuations - Taxes on ISOs and NSOs - The AMT Trap - Stock Awards vs. ISOs vs. NSOs - Taxes on RSUs - Tax Comparison Table - Tax Dangers - Plans and Scenarios - Evaluating Equity Compensation - What Is Private Stock Worth? - Can You Sell Private Stock? - Stock Option Scenarios - Summary of Dangers - Offers and Negotiations - Why Negotiation Matters - Equal Treatment - General Expectations - Offers - Offers From Startups - Questions Candidates Can Ask - Typical Employee Equity Levels - Typical Startup Advisor Equity Levels - Negotiation Tips - Offer and Negotiation Dangers - Documents and Agreements - Further Reading - General Resources - Considerations for Founders - Considerations for Candidates and Employees - Types of Equity Compensation - Taxes - Vesting and Expiration of Stock Options - Negotiation - Forms and Tools - Disclaimer - Credits - Please Help! - License Holloway’s Guide to Equity Compensation is a comprehensive, authoritative resource for founders, managers, and employees. Decisions around equity compensation can be life-changing, and this Holloway Guide offers practical advice on everything from exercising stock options to tax implications to negotiating a job offer from a startup or stock corporation. I wish I’d had access to a resource like this earlier in my career. — Leo Polovets (Susa Ventures) # Researched, written, and edited by experts. #### Written by practitioners. Edited by professionals. Original Authors - Joshua Levy (Holloway) - Joe Wallin (Carney Bradley Spellman) Contributions and Review - José Ancer (Egan Nelson LLP) - Michael Brown (Fenwick & West) - George Grellas (Grellas Shah LLP) - Zach Holman - Chris McCann (Greylock Partners) - Leo Polovets (Susa Ventures) - Eric Tyson Production - Rachel Jepsen — Editor - Andy Sparks — Editor - Hope Hackett — Research - Dmitriy Kharchenko & Leigh Taylor — Graphics # Why pay for an online book? At Holloway, we imagine a place on the web where depth, quality, and high-value writing are the norm. 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