Stock Vesting and Equity Guide
Comprehensive Stock Vesting and Equity Guide
Introduction to Equity Compensation
Equity compensation is a way for companies to provide ownership interest to employees, executives, advisors, and investors. This form of compensation aligns the recipients' interests with those of the company's shareholders by giving them a stake in the company's future success.
Types of Stock
Common Stock
Definition: The basic ownership unit in a company
Characteristics: Last in line for payouts during liquidation; typically held by founders, employees, and early investors
Rights: Usually includes voting rights but fewer economic protections
Preferred Stock
Definition: Stock with additional rights and privileges beyond common stock
Characteristics: Priority in receiving dividends and distributions upon liquidation
Rights: May include dividend preferences, liquidation preferences, anti-dilution protection, and conversion rights
Restricted Stock
Definition: Common stock that is subject to restrictions, typically vesting requirements
Characteristics: Owner has immediate stockholder rights, including voting and dividends
Taxation: Taxed at grant unless an 83(b) election is filed
Stock Vesting Basics
Vesting is the process by which an employee, investor, or other service provider earns their equity over time. Vesting is used to:
Incentivize long-term commitment to the company
Ensure that equity recipients contribute value before fully owning their shares
Protect the company and other shareholders from premature equity distribution
Until stock vests, it cannot be fully owned or sold by the recipient. If a person leaves the company before their shares vest, they typically forfeit the unvested portion.
Understanding Cliffs
A cliff is a period after which a significant portion of equity vests all at once.
Standard Cliff Structure
One-Year Cliff: Most common in startup environments
Functionality: No vesting occurs until the cliff date is reached
Example: With a 4-year vesting schedule and a 1-year cliff, you would earn 0% of your shares until exactly 1 year of service, then 25% would vest immediately
Purpose of Cliffs
Ensures that employees contribute meaningfully before receiving any equity
Protects companies from short-term employees who might otherwise leave with equity after just a few months
Reduces administrative burden of managing small equity positions for short-term employees
What Happens Before the Cliff
Employee has no vested equity
If employment terminates, typically all unvested shares are forfeited
What Happens After Hitting the Cliff
The designated percentage (typically 25% with a 1-year cliff) vests immediately
Regular vesting (often monthly) begins for the remainder of the vesting period
Vesting Schedules
Standard 4-Year Vesting
Most common schedule in tech startups
25% vests at the 1-year cliff
Remaining 75% vests in equal installments (monthly, quarterly, or annually) over the following 3 years
Alternative Schedules
Graded Vesting: Different percentages vest at different intervals
Milestone-Based Vesting: Equity vests upon hitting specific company or individual performance goals
Hybrid Schedules: Combines time-based and milestone-based vesting
Back-Weighted Vesting: Higher percentages vest in later years to encourage longer retention
Continuous vs. Periodic Vesting
Continuous: Shares vest daily or continuously after the cliff
Periodic: Shares vest monthly, quarterly, or annually
Preferred vs. Common Shares
Preferred Shares
Primary Holders: Investors, particularly venture capitalists
Key Features:
Liquidation Preference: Receive distributions before common shareholders (e.g., 1x, 2x, or higher multiples of initial investment)
Participation Rights: May participate in distributions with common shareholders after receiving liquidation preference
Conversion Rights: Ability to convert to common shares (typically at a 1:1 ratio)
Anti-Dilution Protection: Protection against future financing rounds at lower valuations
Dividend Preferences: Priority in receiving dividends
Voting Rights: May have special voting rights for certain company decisions
Common Shares
Primary Holders: Founders, employees, and early angel investors
Key Features:
Standard Voting Rights: Typically one vote per share
Lower Priority: Last to receive proceeds in a liquidation event
Fewer Protections: Minimal protection against dilution or downside scenarios
Series Naming
Each funding round typically creates a new series of preferred stock (Series A, Series B, etc.)
Later series often have more favorable terms than earlier ones
Voting Rights
Common Share Voting
One Vote Per Share: Standard practice for common shares
Matters Typically Voted On:
Election of board members
Major corporate changes (mergers, acquisitions)
Changes to company bylaws
Stock issuances
Changes to capital structure
Preferred Share Voting
Voting Structure Options:
As-Converted Basis: Votes counted as if converted to common shares
Class-Specific Voting: Separate vote among preferred shareholders for certain matters
Board Representation: Rights to elect specific board members
Protective Provisions: Veto rights on specific matters
Voting Right Variations
Super-Voting Shares: Multiple votes per share (often held by founders)
Non-Voting Shares: Shares with economic rights but no voting rights
Class-Specific Rights: Different classes of stock have different voting rights
Proxy Voting
Shareholders may delegate their voting authority to another party
Common with institutional investors and large shareholder blocks
Share Dilution
What Is Dilution?
Dilution occurs when a company issues new shares, reducing the ownership percentage of existing shareholders.
Sources of Dilution
Financing Rounds: New investment rounds add new shares to the cap table
Employee Stock Option Pools: Reserved shares for future employees
Convertible Notes: Debt that converts to equity
SAFEs (Simple Agreement for Future Equity): Agreements to issue shares at a future funding round
Stock Dividends: Additional shares issued to existing shareholders
Anti-Dilution Provisions
Full Ratchet: Adjusts conversion price to match the lowest price of new shares issued
Weighted Average:
Broad-Based: Considers all outstanding shares including options and convertibles
Narrow-Based: Considers only outstanding preferred shares
Pay-to-Play: Requires existing investors to participate in future rounds to maintain anti-dilution protection
Calculating Dilution
Pre-Money Valuation: Company value before new investment
Post-Money Valuation: Company value after new investment
Ownership Percentage: Your shares ÷ Total outstanding shares
Fully Diluted Shares: All outstanding shares + options + warrants + convertibles
Minimizing Dilution Impact
Pre-emptive Rights: Right to maintain percentage ownership by participating in future rounds
Pro-Rata Rights: Right to invest additional capital to maintain ownership percentage
Carve-Outs: Certain share issuances exempt from anti-dilution calculations
Stock Options vs. Restricted Stock Units (RSUs)
Stock Options
Definition: Right to purchase shares at a predetermined price (strike/exercise price)
Types:
Incentive Stock Options (ISOs): Tax-advantaged, employees only
Non-Qualified Stock Options (NSOs/NQSOs): For employees, contractors, advisors
Value: Derives from appreciation above strike price
Exercise: Must pay to acquire actual shares
Expiration: Typically 10 years from grant date
Post-Employment: Usually must be exercised within 90 days after leaving (unless extended)
Restricted Stock Units (RSUs)
Definition: Promise to deliver shares upon vesting
Value: Equal to full share value when vested
Exercise: No purchase required; shares are delivered upon vesting
Taxation: Taxed as income when vested/delivered
Risk Profile: Less downside risk than options
Common Usage: More mature companies, especially public companies
Comparing RSUs and Options
Risk Profile: Options have higher risk/reward; RSUs provide guaranteed value if vested
Company Stage: Options more common at early stage; RSUs more common at later stage
Tax Treatment: Different tax treatment for exercise and sale
Cash Requirements: Options require cash to exercise; RSUs don't
Tax Implications
Stock Options Taxation
ISO Tax Treatment:
No tax at grant
No regular income tax at exercise (but potential AMT implications)
Long-term capital gains if held for 1+ year post-exercise and 2+ years post-grant
NSO Tax Treatment:
No tax at grant
Ordinary income tax on spread at exercise
Capital gains/losses on subsequent appreciation/depreciation
RSU Taxation
No tax at grant
Ordinary income tax on fair market value at vesting
Capital gains/losses on subsequent appreciation/depreciation
83(b) Election
Purpose: Pay tax on grant date value rather than vesting date value
Deadline: Must file within 30 days of receiving unvested equity
Benefits: Starts capital gains clock early; tax based on lower initial value
Risks: If value decreases or shares never vest, taxes paid aren't refundable
Applicability: Available for restricted stock; not applicable to RSUs or options
Tax Upon Sale
Short-Term Capital Gains: Shares held less than one year (taxed as ordinary income)
Long-Term Capital Gains: Shares held more than one year (lower tax rate)
Exercising Options
Exercise Methods
Cash Exercise: Pay the strike price with personal funds
Cashless Exercise: Sell enough shares to cover the exercise price (public companies)
Net Exercise: Company retains shares equal to the exercise price value
Stock Swap: Use already-owned shares to pay for new shares
Early Exercise: Exercise unvested options (requires 83(b) election)
Exercise Considerations
Exercise Window: Period during which options can be exercised
Standard: 90 days post-termination
Extended: Some companies offer longer windows (e.g., 5-10 years)
Exercise Price: Fixed price at which options can be purchased
Market Value: Current fair market value of the stock
Spread: Difference between market value and exercise price (taxable for NSOs)
Lock-up Periods: Restrictions on selling shares (common during/after IPO)
Early Exercise
Definition: Exercising options before they vest
Benefits: Potential tax advantages; starts capital gains clock earlier
Requirements: Company must allow it; must file 83(b) election
Risks: Losing money if shares never vest or decline in value
Acceleration Provisions
Types of Acceleration
Single Trigger: Acceleration based on one event (typically change of control)
Double Trigger: Requires two events (typically change of control AND being terminated without cause)
Partial Acceleration: Only a portion of unvested shares accelerate
Full Acceleration: All unvested shares immediately vest
Common Acceleration Scenarios
Change of Control: Company is acquired or merges
IPO: Company goes public
Termination Without Cause: Employee is laid off or fired without performance issues
Constructive Termination: Material reduction in role, compensation, or relocation requirement
Negotiating Acceleration
Standard Packages:
Executives: Often get single trigger or stronger double trigger
Standard Employees: Typically double trigger if any acceleration
Acceleration Percentage: Can range from 25% to 100% of unvested shares
Cliff Acceleration: Acceleration of shares that would vest within a certain time frame
Key Terms to Know
Cap Table
Comprehensive list of company ownership including all securities
Shows percentage ownership on fully-diluted basis
Tracks how ownership changes over time
409A Valuation
Independent assessment of fair market value (FMV) of private company stock
Required for setting strike prices for options
Updated typically every 12 months or after significant events
Helps avoid tax penalties for below-market option grants
Strike Price
Price at which options can be exercised
Must be at least FMV as of grant date (based on 409A)
Fixed for the life of the option
Exercise Window
Period during which options can be exercised
Standard: Options expire 90 days after employment ends
Extended window: Some companies offer 5-10 years post-termination
Liquidity Event
Occurrence that allows shareholders to cash out
Examples: IPO, acquisition, secondary offering
May trigger acceleration provisions
Right of First Refusal (ROFR)
Company's right to purchase shares before they're sold to a third party
Typically at same price and terms offered by the third party
Common restriction on private company stock
Lock-up Period
Period following IPO when employees cannot sell shares
Typically 180 days
Imposed by underwriters to prevent flooding market with shares
Negotiating Equity Compensation
Understanding Your Offer
Percentage Ownership: More meaningful than number of shares
Fully Diluted Shares: Total including outstanding shares, options, RSUs, warrants, and convertible securities
Equity Value: Number of shares × current price per share
Expected Value: Consider probability of different exit scenarios
Key Negotiation Points
Grant Size: Number of shares/options granted
Vesting Schedule: Standard is 4 years with 1-year cliff
Exercise Price: Should be FMV (based on latest 409A)
Exercise Window: Standard is 90 days; can negotiate for longer
Acceleration Provisions: Whether vesting accelerates upon acquisition or termination
Repurchase Rights: Company's ability to buy back shares
Questions to Ask
What percentage of the company do these shares represent?
When was the last 409A valuation performed?
What is the current preferred share price?
How many funding rounds has the company had?
How much total funding has been raised?
What is the expected timeline to liquidity?
Is there a secondary market for shares?
What has been the historical dilution rate per funding round?
Employee vs. Founder Vesting
Standard Founder Vesting
Schedule: Typically 4 years with 1-year cliff
Rationale: Ensures founders remain committed to the company
Variations:
Credit for time worked before financing
Accelerated vesting milestones
Different schedules for different founders based on contributions
Special Founder Considerations
Reverse Vesting: Founders start with all shares, which are subject to repurchase rights that lapse over time
Accelerated Vesting: More generous acceleration provisions than typical employees
Co-Sale Rights: Right to participate when other shareholders sell shares
Drag-Along Rights: Obligation to sell shares if majority shareholders decide to sell
Founder vs. Employee Differences
Founders typically negotiate directly with investors
Employees typically receive standard plans with limited negotiation
Founders often have better acceleration terms
Founders may receive preferred stock or special classes of common stock
Employees typically receive common stock or options on common stock
This guide provides a comprehensive overview of stock vesting and related equity concepts. As with any financial matter, consult with a professional financial advisor or attorney before making decisions about your specific situation.
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