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# The Open Guide to Equity Compensation

❇️ *This guide is now [published on Holloway](https://www.holloway.com/g/equity-compensation/about).
Read it there for search, booksmarks/highlights, expert commentary, and PDF/EPUB download.*

## Introduction

**Equity compensation** is the practice of granting partial ownership in a company in
exchange for work.
In its ideal form, equity compensation aligns the interests of individual employees with
the goals of the company they work for, which can yield dramatic results in team building,
innovation, and longevity of employment.
Each of these [contributes](#history-and-significance) to the creation of value—for a
company, for its users and customers, and for the individuals who work to make it a
success.

The [ways equity can be granted](#how-equity-is-granted) as compensation—including restricted
stock, stock options, and restricted stock units—are **notoriously complex**. Equity
compensation involves confounding terminology, legal obscurities, and many high-stakes
decisions for those who give and receive it.

If you talk to enough employees and hiring managers, you’ll hear stories of how they or
their colleagues met with the painful consequences of not learning enough up front.
Though many people learn the basic ideas from personal experience or from colleagues or
helpful friends who have been through it before, the intricacies of equity compensation
are best understood by tax attorneys, corporate lawyers, and other professionals.

Decisions related to [negotiating an offer](#offers-and-negotiations) and
[exercising stock options](#stock-option-scenarios), in particular, can have **major financial
consequences**. Because the value of employee equity is determined by the fate of the
company, an employee’s equity may be [illiquid](#what-is-private-stock-worth) for a long time
or ultimately [worth nothing](#growth-and-risk), while taxes and the costs of exercise, if
they apply, may not be recouped.
Even when a company is doing well, an employee may suffer
[catastrophic tax pitfalls](#tax-dangers) because they didn’t anticipate the tax consequences
of their decisions.

Understanding the technicalities of equity compensation does not guarantee that fortune
will smile upon you as warmly as it did [the early hires](#history-and-significance) of
Facebook. But a thorough overview can help you be informed when
[discussing with professionals](#seeking-professional-advice) for further assistance, make
better decisions for your personal situation, and avoid some [common](#tax-dangers) and
[costly](#the-amt-trap) mistakes.

### Why This Guide?

The first edition of this work, written by the same lead authors as the one you’re reading
now, received significant feedback and discussion
[on Hacker News](https://news.ycombinator.com/item?id=10880726),
[on GitHub](https://github.com/jlevy/og-equity-compensation), and from individual experts.
Now, Holloway is pleased to publish this new edition of the Guide.
We’ve expanded sections, added resources and visuals, and filled in gaps.

There is [a lot of information](#further-reading) about equity compensation spread across
blogs and articles that focus on specific components of the topic, such as vesting, types
of stock options, or equity levels.
We believe there is a need for a consolidated and shared resource, written by and for
people on different sides of compensation decisions, including employees, hiring managers,
founders, and students.
Anyone can feel overwhelmed by the complex details and high-stakes personal choices that
this topic involves.
This reference exists to answer the needs of beginners and the more experienced.

Holloway and our contributors are motivated by a single purpose:
To help readers understand important details and their contexts well enough to make better
decisions themselves.
The Guide aims to be **practical** (with concrete suggestions and pitfalls to avoid),
**thoughtful** (with context and multiple expert perspectives, including divergent opinion on
controversial topics), and **concise** (it is dense but contains only notable details—still,
it’s at least a three-hour read, with links to three hundred sources!).

The Guide does not purport to be either perfect or complete.
A reference like this is always in process.
That’s why we’re currently testing features to enable the Holloway community to suggest
improvements, contribute new sections, and call out anything that needs revision.
We welcome (and will gladly credit) [your help](#please-help).

We especially wish to [recognize](#credits) the dozens of people who have helped write,
review, edit, and improve it so far—and in the future—and hope you’ll check back often as
it improves.

### Scope

This Guide **currently covers**:

- Equity compensation in **C corporations** in the **United States**.
- Equity compensation for most employees, advisors, and independent contractors in private
  companies, from startups through larger private corporations.
- Limited coverage of equity compensation in public companies.

Topics **not yet covered**:

- Equity compensation programs, such as [ESPPs](https://www.investopedia.com/terms/e/espp.asp)
  in public companies.
  (We’d like to [see this improve](#please-help) in the future.)
- Full details on executive equity compensation.
- Compensation outside the United States.
- Compensation in companies other than C corporations, including
  [LLCs](https://en.wikipedia.org/wiki/Limited_liability_company) and
  [S corporations](https://en.wikipedia.org/wiki/S_corporation), where equity compensation is
  approached and practiced in very different ways.

For these situations, see [other resources](#when-to-turn-elsewhere) and get
[professional advice](#seeking-professional-advice).

### Who May Find This Useful

Our aim is to be as helpful to the beginner as to those with more experience.
Having talked with employees, CEOs, investors, and lawyers, we can assure you that no
matter how much you know about equity compensation, you will likely run into confusion at
some point.

If you’re an **employee** or a **candidate for a job**, some of these may apply to you:

- You’ve heard phrases like *stock*, *stock options*, *strike price*, *ISOs*, *RSUs*, *83(b)
  election*, *409A valuation*, *AMT*, or *early exercise* and know they are probably
  important but are mystified by what some of them really mean or whether they apply to your
  situation.
- You’re considering a job offer but don’t know how to
  [navigate or negotiate](#offers-and-negotiations) the equity component of the offer.
- You’re joining a startup for the first time and are overwhelmed by all the
  [paperwork](#documents-and-agreements).
- You’re quitting, taking a leave of absence, or are being laid off or fired from a company
  where you have stock or options and are thinking through the decisions and consequences.
- A company you work for is going through an acquisition, IPO, or shutdown.
- You have stock in a private company and [need cash](#stock-option-scenarios).

**Founders** or **hiring managers** who need to talk about equity compensation with employees
or potential hires will also find this Guide useful.
As many entrepreneurs and hiring managers will tell you, this topic isn’t easy on that
side of the table, either!
Negotiating with candidates and fielding questions from candidates and employees requires
understanding the same complex technicalities of equity compensation well.

That said, this topic is **not simple** and we ask that readers be willing to invest time to
get through a lot of confusing detail.
If you’re in a hurry, or you don’t care to learn the details, this Guide may not be for
you. [Seek advice](#seeking-professional-advice).

### A Note on Fairness

Much of what you read about equity compensation was written by a single person, from a
single vantage point.
The authors and editors of this Guide have navigated the territory of equity compensation
from the perspective of employees, hiring managers, founders, and lawyers.
We do believe that the knowledge here,
[combined with professional advice](#seeking-professional-advice), can make a significant
difference for **both employees and hiring managers**.

One of the difficulties for candidates negotiating equity compensation is that they may
have less information about what they are worth than the person hiring them.
Companies talk to many candidates and often have access to or pay for expensive
market-rate compensation data.
While some data on [typical equity levels](#typical-employee-equity-levels) have been
published online, much of it fails to represent the value of a candidate with their own
specific experience in a specific role.
However, even without exact data, candidates and hiring managers can develop better mental
frameworks to think about [offers and negotiations](#offers-and-negotiations).

On the other hand, challenges are not limited to those of employees.
Founders and hiring managers also often struggle with talking through the web of
technicalities with potential hires, and can make equally poor decisions when making
offers. Either over-compensating or under-compensating employees can have unfortunate
consequences.

In short, both companies and employees are routinely hurt by uninformed decisions and
costly mistakes when it comes to equity compensation.
A shared resource is helpful for both sides.

## Roadmap

### The Holloway Reader

The Holloway Reader you’re using now is designed to help you find and navigate the
material you need. **Use the search box.**
It will reveal definitions, section-by-section results, and content contained in **the
hundreds of resources we’ve linked to** throughout the Guide.
Think of it as a mini library of the best content on equity compensation.
We also provide mouseover (or short tap on mobile) for **definitions of terms**, related
section suggestions, and external links while you read.

### How This Guide Is Organized

This Guide contains a lot of material.
And it’s dense.
Some readers may wish to read front to back, but you can also **search or navigate directly**
to parts that are of interest to you, **referring back** to foundational topics as needed.

Equity compensation lies at the intersection of corporate law, taxation, and employee
compensation, and so requires some basic understanding of all three.
You might think compensation and taxation are separate topics, but they are so intertwined
it would be misleading to explain one without the other.
We cover material in logical order, so that if you do read the earlier sections first,
later sections on the interactions of tax and compensation will be clearer.

We start with [**Equity Compensation Basics**](#equity-compensation-basics): What compensation
and equity are, and why equity is used as compensation.

But before we get much further, we need to talk about what stock is, and how companies are
formed. [**Fundamentals of Stock Corporations**](#fundamentals-of-stock-corporations) covers how
companies organize their ownership, how stock is issued, public companies and private
companies, and IPOs and liquidity (which determine when equity is worth cash).

While not everyone reading this works at an early stage company, those who do can benefit
from understanding the role of equity in [**Startups and Growth**](#startups-and-growth). This is
good context for anyone involved in a private company that has taken on venture capital.

[**How Equity is Granted**](#how-equity-is-granted) is the core of this Guide.
We describe the forms in which equity is most commonly granted, including restricted stock
grants, stock options, and RSUs.

Now is where it gets messier—taxes:

- [**Tax Basics**](#tax-basics): A technical summary of how taxation works.
  Many of the headaches of equity compensation involve how it is taxed, including ordinary
  income tax, long-term capital gains tax, and the lesser-known but sometimes critical
  alternative minimum tax.
- [**Taxes on Equity Compensation**](#taxes-on-equity-compensation): How much tax you owe is greatly
  affected by the kind of equity you have (such as restricted stock awards, stock options,
  or RSUs), when you choose to pay (including 83(b) elections), and when you choose to
  exercise options.

After these technical concerns, we move on to how you can think about all this in
practice. These sections focus on scenarios common to employees and candidates, but are
also of likely interest to founders and hiring managers:

- [**Plans and Scenarios**](#plans-and-scenarios): Whether you have equity now or will in the
  future, it is helpful to learn *how to think about* the value of equity and its tax
  burden. We also cover whether you can [sell private stock](#can-you-sell-private-stock).
- [**Offers and Negotiations**](#offers-and-negotiations): Equity often comes up as you’re
  negotiating or debating whether to accept a job offer.
  Here we cover what to expect, what to ask, tips and pitfalls, and more.

Finally, we offer some additional resources:

- [**Documents and Agreements**](#documents-and-agreements): A bit more detail on the actual legal
  paperwork you’re likely to see as you negotiate and after you’ve accepted an offer.
- [**Further Reading**](#further-reading): A curated list of what else you can read on the subject,
  including many papers, books, and articles that have informed this Guide.

🚧 What about a Getting Help section outlining when to go to whom for professional help?

### When to Turn Elsewhere

**CEOs**, **CFOs**, **COOs**, or anyone who runs a company or team of significant size should be
sure to talk to an equity compensation consultant or a specialist at a law firm to learn
about equity compensation plans.

**Founders** looking for an introduction to the legalities of running a company may wish to
check out [*Legal Concepts for Founders*](https://handbook.clerky.com/), from Clerky, in
addition to talking to a lawyer.
Founders should also lean on their investors for advice, as they may have additional
experience.

**Executive compensation** at large or public companies is an even more nuanced topic, on
both sides of the table.
Hire an experienced lawyer or compensation consultant.
There are extensive legal [resources](https://www.compensationstandards.com/home/) available
on executive compensation.

### Seeking Professional Advice

This Guide does not replace professional advice.

Please read the full [disclaimer](#disclaimer) and seek professional advice from a lawyer,
tax professional, or other compensation expert before making significant decisions.

Does that make reading through these details a waste of time?
Not at all. Important decisions rarely should or can be blindly delegated.
This Guide *complements but does not replace* the advice you get from professionals.
Working with the support of a professional can help you make better decisions when you
have an understanding of the topic yourself and know what questions to ask.

## Equity Compensation Basics

### History and Significance

Companies ranging from two-person startups to the
[Fortune 500](http://fortune.com/fortune500/) have found that granting partial ownership in a
company is among the best methods to attract and retain exceptional talent.
In the United States, partial ownership through [stock options](#stock-options) has been a
key part of pay for executives and other employees since the 1950s.[^corpgovlaw.6vw7qt]
As recently as 2014, **7.2%** of all private sector employees (**8.5 million** people) and
**13.1%** of *all* employees of companies with stock held stock options, according to the
National Center for Employee Ownership.[^nceoorgass.x6588n]
Many believe employee ownership has
[💰fostered innovations](https://www.wsj.com/articles/reviving-the-flagging-spirit-of-silicon-valley-1428706671)
in technology, especially in Silicon Valley, from the
[early days](http://www.hp.com/hpinfo/abouthp/histnfacts/publications/measure/pdf/1976_07.pdf)
of Hewlett-Packard to recent examples like Facebook.
Stock options helped the first 3,000 employees of Facebook enjoy roughly **$23 billion** at
the time the company went public.[^ftcomconte.x613np]

🌪 Some controversy surrounds the use of equity compensation for high-paid executives.
Public companies offer executives equity compensation in no small part because of a tax
loophole. In 1993, President Bill Clinton attempted to limit executive pay with a new
section[^treasurygo.tbpcyx] of the Internal Revenue Code.
Unfortunately, the legislation backfired;
a loophole made performance-based pay—including stock options—fully tax deductible,
thereby creating a dramatic incentive to pay executives through stock options.[^epiorgpubl.cq5o0o]
From 1970–79, the average compensation for a CEO of one of the 50 largest firms in the
United States was **$1.2M**, of which **11.2%** was from stock options.
By 2000–05, the same numbers had risen to **$9.2M** and **37%**, respectively.[^nberorgpap.wtsymr]

### Growth and Risk

Generally, equity compensation is closely linked to the **growth** of a company.
Cash-poor startups persuade early employees to take pay cuts and join their team by
offering meaningful [ownerships stakes](#typical-employee-equity-levels), catering to hopes
that the company will one day grow large enough to [go public](#ipos) or
[be sold](#sales-and-liquidity) for an ample sum.
More mature but still fast-growing companies find offering compensation linked to
ownership is more attractive than high cash compensation to many candidates.

With the hope for growth, however, also comes **risk**. Large, fast-growing companies often
hit hard times.
And [startups](#startups-and-growth) routinely fail or yield no returns for investors or
workers. According to [a report](http://fortune.com/2017/06/27/startup-advice-data-failure/)
by Cambridge Associates and Fortune Magazine, between 1990 and 2010, **about 60%** of
venture capital-backed companies returned less than the original investment, leaving
employees with the painful realization that their startup was not, in fact, the next
Google. Of the remaining **40%**, just a select few go on to make a many of their employees
wealthy, as has been the case with iconic high-growth companies, like Starbucks,[^investoped.aaps6n] UPS,[^moneycnnco.80o8bh]
Amazon,[^techcrunch.9ucopn] Google,[^dealbookny.es6h1j] or Facebook.[^enwikipedi.q7bc95]

### Compensation and Equity

🄳 **Compensation** is any remuneration to a person (including employees, contractors,
advisors, founders, and board members) for services performed or rendered to a company.
Compensation comes in the forms of cash pay (salary and any bonuses) and any non-cash pay,
including [benefits](https://en.wikipedia.org/wiki/Employee_benefits#United_States) like
health insurance, family-related protections, perks, and retirement plans.

Company strategies for compensation are
[far from simple](http://firstround.com/review/counterintuitive-comp-tips-for-the-unwary-and-uninitiated/).
Beth Scheer, head of talent at the venture fund Homebrew, offers a
[thoughtful overview](https://quip.com/HEB3Ah9dYD6o) of compensation in startups.

Another term you may encounter is
[*total rewards*](https://www.worldatwork.org/total-rewards-model/), which refers to a model of
attracting and retaining employees using a combination of salary and incentive
compensation (like equity), benefits, recognition for contribution or commitment (like
awards and bonuses), training programs, and initiatives to improve the work environment.

🄳 In the context of compensation and investment, **equity** broadly refers to any kind of
ownership in a company that can be held by individuals (like employees or board members)
and by other businesses (like venture capital firms).
One common kind of equity is stock, but equity can take other forms, such as stock options
or warrants, that give ownership rights.
Commonly, equity also comes with certain conditions, such as vesting or repurchase rights.
Note the term *equity* also has
[several other](https://www.investopedia.com/terms/e/equity.asp) technical meanings in
accounting and real estate.

🄳 [**Equity compensation**](http://www.investopedia.com/terms/e/equity-compensation.asp) is the
practice of granting equity in exchange for work.

In this Guide we focus on equity compensation in stock corporations, the kind of company
where ownership is represented by stock.
(We describe stock in more detail in [the next section](#fundamentals-of-stock-corporations).)
Equity compensation in the form of a direct grant of stock with no strings attached is
very rare. Instead, employees are given stock with additional restrictions placed on it,
or are given contractual rights that later can lead to owning stock.
These forms of equity compensation include restricted stock, stock options, and restricted
stock units, each of which we’ll [describe in detail](#how-equity-is-granted).

### The Goals of Equity Compensation

The purpose of equity compensation is threefold:

- **Attract and retain talent.**
  When a company already has or can be predicted to have significant financial success,
  talented people are [incentivized](https://avc.com/2010/10/employee-equity-options/) to work
  for the company by the prospect of their equity being
  [worth a lot](https://www.entrepreneur.com/article/253438) of money in the future.
  The actual probability of life-changing lucre may be low (or at least, lower than you may
  think if your entire knowledge of startups is watching “[The Social Network](https://en.wikipedia.org/wiki/The_Social_Network)”).
  But even a small chance at winning big can be worth the risk to many people, and to some
  the risk itself can be exciting.
- **Align incentives.**
  Even companies that can afford to pay lots of cash may prefer to give employees equity,
  so that employees work to increase the *future* value of the company.
  In this way, equity aligns individuals’ incentives with the interests of the company.
  At its best, this philosophy fosters an environment of teamwork and a “rising tides lift
  all boats” mentality.
  It also encourages everyone involved to think
  [long-term](https://www.cebglobal.com/blogs/equity-compensation-will-stop-short-termism-and-boost-growth/),
  which is key for company success.
  As we’ll [discuss later](#offers-and-negotiations), the amount of equity you’re offered
  usually reflects both your contribution to the company and your commitment to the company
  in the future.
- **Reduce cash spending.**
  By giving equity, a company can often pay less in cash compensation to employees now,
  with the hope of rewarding them later, and put that money toward other investments or
  operating expenses.
  This can be essential in the early stages of a company or at other times where there may
  not be enough revenue to pay large salaries.
  Equity compensation can also help recruit senior employees or executives who would
  otherwise command especially high salaries.

🚧 Mention or link to lockup periods etc.

## Fundamentals of Stock Corporations

In this section, we describe the basics of how stock and shares are used.

Those familiar with stock, stock corporations, public companies, and private companies can
[jump ahead](#how-equity-is-granted) to how those companies grant equity.

### Kinds of Companies

🄳 A **company** is a legal entity formed under corporate law for the purpose of conducting
trade. In the United States, specific rules and regulations govern several kinds of
[business entities](https://en.wikipedia.org/wiki/Types_of_business_entity#United_States).
Federal and state law have significant implications on liability and taxation for each
kind of company.
Notable types of companies include sole proprietorships, partnerships, limited liability
companies (LLCs), S corporations, and C corporations.

🄳 A **corporation** is a company that is legally recognized as a single entity.
The corporation itself, and not its owners, is obligated to repay debts and accountable
under contracts and legal actions (that is, is a “[legal person](https://en.wikipedia.org/wiki/Legal_person)”).
Most commonly, the term *corporation* is used to refer to a
**[stock corporation (or joint-stock company)](https://en.wikipedia.org/wiki/Joint-stock_company)**,
which is a corporation where ownership is managed using stock. **Non-stock corporations**
that do not issue stock exist as well, the most common being
[nonprofit organizations](https://en.wikipedia.org/wiki/Nonprofit_organization). (A few
[less common](https://en.wikipedia.org/wiki/Non-stock_corporation) for-profit non-stock
corporations also exist.)

In practice, people often use the word *company* to mean *corporation*.

🄳 **Incorporation** is the
[legal process](https://en.wikipedia.org/wiki/Incorporation_(business)) of forming (or
**incorporating**) a new corporation, such as a business or nonprofit.
Corporations can be created in any country.
In the United States, incorporation is handled by state law, and involves filing
[articles of incorporation](https://en.wikipedia.org/wiki/Articles_of_incorporation) and a
variety of other [required information](https://handbook.clerky.com/formation/process) with
the Secretary of State.
(Note that the formation of companies that are not corporations, such as partnerships or
LLCs, is not the same as incorporation.)

🄳 A [**C corporation (or C corp)**](https://en.wikipedia.org/wiki/C_corporation) is a type of
stock corporation in the United States with certain federal
[tax treatment](https://ct.wolterskluwer.com/resource-center/articles/what-c-corporation). It
is the most prevalent kind of corporation.[^investoped.m9wdqp]
Most large, well-known American companies are C corporations.
C corporations differ from
[S corporations](https://www.incorporate.com/starting-a-business/s-corporation) and other
business entities in several ways, including how income is taxed and who may own stock.
C corporations have no limit on the number of shareholders allowed to own part of the
company. They also allow other corporations, as well as partnerships, trusts, and other
businesses, to own stock.

C corps are overwhelmingly popular for early-stage
[private companies](#public-and-private-companies) looking to sell part of their business in
exchange for investment from individuals and organizations like venture capital firms
(which are often partnerships), and for established public companies selling large numbers
of stock to individuals and other companies on the
[public exchange](https://en.wikipedia.org/wiki/Stock_exchange).

In practice, for a few reasons, these companies are usually formed in Delaware, so
legalities of all this are defined in Delaware law.[^quoracomwh.wsnr2b][^nytimescom.67ksyb]
You can think of Delaware law as the primary “language” of U.S. corporate law.
Incorporating a company in Delaware has evolved into a national standard for high-growth
companies, regardless of where they are physically located.

🔸 This Guide focuses specifically on C corporations and [does not cover](#scope) how equity
compensation works in LLCs, S corporations, partnerships, or sole proprietorships.
Both equity and compensation are handled in significantly different ways in each of these
kinds of businesses.

Loosely, one way to think about companies is that they are simply a set of
[contracts](https://www.law.cornell.edu/wex/contract), negotiated over time between the people
who own and operate the company, and which are enforced by the government, that aligns the
interests of everyone involved in creating things customers are willing to pay for.
Key to these contracts is a way to precisely track ownership of the company;
issuing stock is how companies often choose to do this.

🚧 Mention how court cases are settled?

### Stock and Shares

🄳 [**Stock**](https://en.wikipedia.org/wiki/Stock) is a legal invention that represents
ownership in a company. [**Shares**](https://en.wikipedia.org/wiki/Share_(finance)) are portions
of stock that allow a company to grant ownership to a variety of people or other companies
in flexible ways.
Each **shareholder (or stockholder)**, as these owners are called, holds a specific number
of shares. Founders, investors, employees, board members, contractors, advisors, and other
companies, like law firms, can all be shareholders.

🄳 Stock ownership is often formalized on **stock certificates**, which are fancy pieces of
paper that prove who owns the stock.

Sometimes you have stock but don’t have the physical certificate, as it may be held for
you at a law office.

Some companies now manage their ownership through online services called *ownership
management platforms*, such as [Carta](https://carta.com/). If the company you work for uses
an ownership management platform, you will be able to view your stock certificates and
stock values online.

Younger companies may also choose to keep their stock *uncertificated*, which means your
sole evidence of ownership is your contracts with the company, and your spot on the
company’s cap table, without having a separate certificate for it.

🄳 [**Outstanding shares**](http://www.investopedia.com/terms/o/outstandingshares.asp) refer to
the total number of shares held by all shareholders.
This number starts at an essentially arbitrary value (such as 10 million) when the company
is created, and thereafter will increase as new shares are added (issued) and granted to
people in exchange for money or services.

Outstanding shares may increase or decrease for other reasons too, such as
[stock splits and share buybacks](http://www.investorguide.com/article/11713/splits-and-buybacks-explained/),
which we won’t get into here.

Later, we discuss several [subtleties](#counting-shares) in how shares are counted.

🚧 What is a good overview on stock splits and share buyback.
Key resources?

🄳 Any shareholder has a **percentage ownership** in the company, determined by dividing the
number of shares they own by the number of outstanding shares.
Although stock paperwork will always list numbers of shares, if share value is uncertain,
percentage ownership is often a more meaningful number, particularly if you know or can
estimate a likely valuation of the company.
Even if the number of shares a person has is fixed, their percentage ownership will change
over time as the outstanding shares change.
Typically, this number is presented in percent or
[**basis points**](https://www.investopedia.com/terms/b/basispoint.asp) (hundredths of a percent).

### Public and Private Companies

🄳 [**Public companies**](https://en.wikipedia.org/wiki/Public_company) are corporations in which
any member of the public can own stock.
People can buy and sell the stock for cash on public
[stock exchanges](https://www.investopedia.com/terms/e/exchange.asp). The value of a company’s
shares is the value displayed in the stock market reports, so shareholders know how much
their stock is worth.

🄳 Most smaller companies, including all startups, are
[**private companies**](https://en.wikipedia.org/wiki/Privately_held_company) with owners who
control how those companies operate.
Unlike a public company, where anyone is able to buy and sell stock, owners of a private
company control who is able to buy and sell stock.
There may be few or no transactions, or they may not be publicly known.

🚧 What are public exchanges and how is stock bought and sold in practice?
Mention accredited investors?

### Governance

🄳 A corporation has a **board of directors**, a
[group of people](https://en.wikipedia.org/wiki/Board_of_directors) whose legal obligation is
to oversee the company and ensure it serves the best interests of the shareholders.
Public companies are legally obligated to have a board of directors, while private
companies often elect to have one.
The board typically consists of **inside directors**, such as the CEO, one or two founders,
or executives employed by the company, and **outside directors**, who are not involved in
the day-to-day workings of the company.
These **board members** are elected individuals who have legal, corporate governance rights
and duties when it comes to voting on key company decisions.
A board member is said to have a **board seat** at the company.

Boards of directors range from 3 to 31 members, with an average size of 9.[^investoped.fn52lq] Boards are
almost always an odd number in order to avoid tie votes.
It’s worth noting that the state of California requires public companies to have at least
one woman on their boards.[^nytimescom.gec7iw]

Key decisions of the board are made formally in *board meetings* or in writing (called
*written consent*).[^dlapiperac.wb4617] Many decisions around granting equity to employees are approved by the
board of directors.

🚧 This section could be expanded, and also include more legal links.

### IPOs

🄳 A private company becomes a public company in a process called an
[**initial public offering (IPO)**](https://en.wikipedia.org/wiki/Initial_public_offering).
Historically, only private companies with a strong track record of years of growth have
considered themselves ready to take this significant step.
The IPO has [pros and cons](https://www.investopedia.com/university/ipo/ipo.asp) that include
exchanging a host of high regulatory costs for the benefits of significant capital.
After a company “IPOs” or “**goes public**," investors and the general public can buy stock,
and existing shareholders can sell their stock far more easily than when the company was
private.

Companies take years to IPO after being formed.
The median time between a company’s founding and its IPO has been increasing.
According to a Harvard report, companies that went public in **2016** took **7.7 years** to do
so, compared to **3.1 years** for companies that went public in **1996**.[^corpgovlaw.vbw82s]

🚧 What are the restrictions and regulations on selling stock that affect employees at
IPO? What is a lockup period?

### Sales and Liquidity

❗️ With private companies, it can be very [hard to know](#what-is-private-stock-worth) the
value of equity.
Because the value of private company stock is not determined by regular trades on public
markets, shareholders can only make educated guesses about the likely future value, at a
time when they will be able to sell stock.

After all, private company stock is simply a legal agreement that entitles you to
something of highly uncertain value, and could well be worthless in the future, or highly
valuable, depending on the fate of the company.

☝️ We’ll discuss the notion of a company officially assigning a
[fair market value](#409a-valuations) later, but even if a company gives you a value for your
stock for tax and accounting purposes, it doesn’t mean you can expect to sell it for that
value!

🄳 An [**acquisition**](https://www.investopedia.com/terms/a/acquisition.asp) is the purchase of
more than 50% of the shares of one company (the acquired company) by another company (the
purchaser). This is also called a **sale** of the acquired company.
In an acquisition, the acquired company cedes control to the purchaser.

🄳 The ability to buy and sell stock is called **liquidity**. In startups and many private
companies, it is often hard to sell stock until the company is sold or goes public, so
there is little or no liquidity for shareholders until those events occur.
Thus, sales and IPOs are called both **exits** and **liquidity events**. Sales, dissolutions,
and bankruptcy are all called **liquidations**.

Often people wish they could sell stock in a private company, because they would prefer
having the cash.
This is only possible occasionally.
We get into the details [later](#can-you-sell-private-stock), in our section on selling
private stock.

🄳 A [**dividend**](http://www.investopedia.com/terms/d/dividend.asp) is a distribution of a
company’s profit to shareholders, authorized by the board of directors.
Established public companies and some private companies pay dividends, but this is rare
among startups and companies focused on rapid growth, since they often wish to re-invest
their profits into expanding the business, rather than paying that money back to
shareholders. Amazon, for example, has
[never paid](https://www.fool.com/investing/2017/12/28/will-amazon-start-paying-a-dividend-in-2018.aspx)
dividends.

## Startups and Growth

If you’re considering working for a startup, what we cover next on how these early-stage
companies raise money and grow is helpful in understanding what your equity may be worth.

If you’re only concerned with large and established companies, you can skip ahead to
[how equity is granted](#how-equity-is-granted).

### Startups

🄳 A [**startup**](https://en.wikipedia.org/wiki/Startup_company) is an emerging company,
typically a private company, that aspires to grow quickly in size, revenue, and influence.
Once a company is established in the market and successful for a while, it usually stops
being called a startup.

☝️ Unlike the terminology around corporations, which has legal significance, the term
*startup* is informal, and not everyone uses it consistently.

Startups are not the same as small businesses.
Small businesses, like a coffee shop or plumbing business, typically intend to grow slowly
and organically, while relying much less on investment capital and equity compensation.
Distinguished startup investor
[Paul Graham](https://en.wikipedia.org/wiki/Paul_Graham_(programmer)) has
[emphasized](http://www.paulgraham.com/growth.html) that it’s best to think of a startup as
any [early stage](#stages-of-a-startup) company intending to grow quickly.

∑ C corporations dominate the startup ecosystem.
LLCs tend to be better suited for slower-growth companies that intend to distribute
profits instead of re-investing them for growth.
Because of this, and for complex reasons related to how their capital is raised, venture
capitalists significantly prefer to invest in C corporations.

🚧 What are good stats on how many people work in startups vs.
established companies?

### Fundraising, Growth, and Dilution

Many large and successful companies began as startups.
In general, startups rely on investors to help fund rapid growth.

🄳 **Fundraising** is the process of seeking capital to build or scale a business.
Selling shares in a business to investors is one form of fundraising, as are loans and
[initial coin offerings](https://en.wikipedia.org/wiki/Initial_coin_offering). **Financing**
refers both to fundraising from outside sources and to bringing in revenue from selling a
product or service.

🄳 **Venture capital** is a form of financing for early-stage companies that individual
investors or investment firms provide in exchange for partial ownership, or equity, in a
company. These investors are called **venture capitalists (or VCs)**. Venture capitalists
invest in companies they perceive to be capable of growing quickly and commanding
significant market share.
“Venture” refers to the risky nature of investing in early-stage businesses—typically
startups—with unproven business models.

A startup goes through several [stages of growth](#stages-of-a-startup) as it raises capital
based on the hope and expectation that the company will grow and make more money in the
future.

🄳 Companies add (or “issue”) shares during fundraising, which can be exchanged for cash
from investors.
As the number of outstanding shares goes up, the percentage ownership of each shareholder
goes down. This is called [**dilution**](http://www.investopedia.com/terms/d/dilution.asp).

☝️ Dilution doesn’t necessarily mean that you’re losing anything as a shareholder.
As a company issues stock and raises money, the smaller percentage of the company you *do*
have could be worth more.
The size of your slice gets relatively smaller, but, if the company is growing, the size
of the cake gets bigger.
For example, a typical startup might have three rounds of funding, with each round of
funding issuing 20% more shares.
At the end of the three rounds, there are more outstanding shares—roughly 73% more in this
case, since 120%×120%×120% is 173%—and each shareholder owns proportionally less of the
company.

🄳 The [**valuation**](https://en.wikipedia.org/wiki/Valuation_(finance)) of the company is the
present value investors believe the company has.
If the company is doing well, growing revenue or showing indications of future revenue
(like a growing number of users or traction in a promising market), the company’s
valuation will usually be on the rise.
That is, the [price](https://en.wikipedia.org/wiki/Share_price) for an investor to buy one
share of the company would be increasing.

❗️ Of course, things do not always go well, and the valuation of a company does not always
go up. It can happen that a company fails entirely and all ownership stakes become
worthless, or that the valuation is lower than expected and
[certain kinds](#classes-of-stock) of shares become worthless while other kinds have some
value. When investors and leadership in a company expect the company to do better than it
actually does, it can have a lot of disappointing consequences for shareholders.

### Dilution Illustrations

These visualizations illustrate how ownership of a venture-backed company evolves as
funding is raised.
One scenario imagines changes to ownership in a well-performing startup, and the other is
loosely based on a careful analysis of Zipcar,[^reactionwh.uw835n] a ride-sharing company that experienced
substantial dilution before eventually going public and being
[acquired](#sales-and-liquidity). These diagrams simplify complexities such as the ones
discussed in that analysis, but they give a sense of how ownership can be diluted.

```hlwy-infographics
{
  "name": "CaptableDilution",
  "data": {
    "hypothetical": {
      "label": "Hypothetical",
      "stages": [
        {
          "label": "Founding",
          "postValuation": 1000,
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 4000000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 3000000
            },
            {
              "type": "founder3",
              "label": "Founder #3",
              "shares": 3000000
            }
          ]
        },
        {
          "label": "Series A",
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 4000000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 3000000
            },
            {
              "type": "founder3",
              "label": "Founder #3",
              "shares": 3000000
            },
            {
              "type": "options",
              "label": "Options Pool",
              "shares": 1500000
            },
            {
              "type": "investment",
              "label": "Seed",
              "preValuation": 8000000,
              "raised": 2000000
            },
            {
              "type": "investment",
              "label": "Series A",
              "preValuation": 8000000,
              "raised": 5000000
            }
          ]
        },
        {
          "label": "Series C",
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 4000000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 3000000
            },
            {
              "type": "founder3",
              "label": "Founder #3",
              "shares": 3000000
            },
            {
              "type": "options",
              "label": "Options Pool",
              "shares": 1500000
            },
            {
              "type": "investment",
              "label": "Seed",
              "preValuation": 8000000,
              "raised": 2000000
            },
            {
              "type": "investment",
              "label": "Series A",
              "preValuation": 8000000,
              "raised": 5000000
            },
            {
              "type": "investment",
              "label": "Series B",
              "preValuation": 20000000,
              "raised": 10000000
            },
            {
              "type": "investment",
              "label": "Series C",
              "preValuation": 40000000,
              "raised": 20000000
            }
          ]
        }
      ]
    },
    "zipcar": {
      "label": "Approx. Zipcar",
      "stages": [
        {
          "label": "Founding",
          "postValuation": 1000,
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 570000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 570000
            }
          ]
        },
        {
          "label": "Series A",
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 570000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 570000
            },
            {
              "type": "options",
              "label": "Options Pool",
              "shares": 378000
            },
            {
              "type": "investment",
              "label": "Series A",
              "preValuation": 5800000,
              "raised": 1400000
            }
          ]
        },
        {
          "label": "Series B",
          "captable": [
            {
              "type": "founder1",
              "label": "Founder #1",
              "shares": 570000
            },
            {
              "type": "founder2",
              "label": "Founder #2",
              "shares": 570000
            },
            {
              "type": "options",
              "label": "Options Pool",
              "shares": 378000
            },
            {
              "type": "investment",
              "label": "Series A",
              "preValuation": 5800000,
              "raised": 1400000
            },
            {
              "type": "investment",
              "label": "Series A",
              "preValuation": 2200000,
              "raised": 4700000
            }
          ]
        }
      ]
    }
  }
}
```

### Stages of a Startup

Understanding the value of stock and equity in a startup requires a grasp of the stages of
growth a startup goes through.
These stages are largely reflected in how much funding has been raised—how much ownership,
in the form of shares, has been sold for capital.

Very roughly,
[typical stages](http://blog.eladgil.com/2011/03/how-funding-rounds-differ-seed-series.html)
are:

- [**Bootstrapped**](https://www.investopedia.com/terms/b/bootstrapping.asp) (little funding or
  self-funded): Founders are figuring out what to build, or they’re starting to build with
  their own time and resources.
- [**Series Seed**](https://www.investopedia.com/terms/s/seedcapital.asp) (roughly $250K to $2
  million in funding): Figuring out the product and market.
  The low end of this spectrum is now often called **pre-seed**.
- [**Series A**](https://www.investopedia.com/terms/s/seriesa.asp) ($2 to $15 million): Scaling the
  product and making the business model work.
- [**Series B**](https://www.investopedia.com/terms/s/series-b-financing.asp) (tens of millions):
  Scaling the business.
- **Series C, D, E, et cetera** (tens to hundreds of millions): Continued scaling of the
  business.

Keep in mind that these numbers are more typical for startups located in California.
The amount raised at various stages is typically smaller for companies located outside of
Silicon Valley, where what would be called a seed round may be called a Series A in, say,
Houston, Denver, or Columbus, where there are fewer companies competing for investment
from fewer venture firms, and costs associated with growth (including providing livable
salaries) are lower.[^nytimescom.bcfuyu][^chicagotri.fq0msp]

🔸 Most startups don’t get far.
According to an analysis of
[angel investments](https://www.investopedia.com/terms/a/angelinvestor.asp), by Susa Ventures
general partner [Leo Polovets](http://codingvc.com), **more than half** of investments fail;
**one in 3** are small successes (1X to 5X returns); **one in 8** are big successes (5X to
30X); and **one in 20** are huge successes (30X+).[^codingvcco.bcspni]

🚧 What are some stats beyond angel investments?

🔸 Each stage reflects the reduction of risk and increased dilution.
For this reason, the amount of equity team members get is higher in the earlier stages
(starting with founders) and increasingly lower as a company matures.
(See the picture above.)

### The Option Pool

🄳 At some point early on, generally before the first employees are hired, a number of
shares will be reserved for an employee
**[option pool](http://www.investopedia.com/terms/o/option-pool.asp) (or employee pool)**. The
option pool is part of a legal structure called an equity incentive plan.
A typical size for the option pool is 20% of the stock of the company, but, especially for
earlier stage companies, the option pool can be 10%, 15%, or other sizes.

Once the pool is established, the company’s board of directors grants stock from the pool
to employees as they join the company.

∑ Well-advised companies will reserve in the option pool only what they
[expect to use](http://siliconhillslawyer.com/2014/05/01/option-pool-not-ocean-startups/) over
the next 12 months or so;
otherwise, given how equity grants are usually promised, they may be over-granting equity.
The whole pool may never be fully used, but companies should still try not to reserve more
than they plan to use.
The size of the pool is determined by
[complex factors](http://venturehacks.com/articles/option-pool-shuffle) between founders and
investors. It’s worth employees (and
[founders](https://www.cooleygo.com/negotiating-option-pool/)) understanding that a small pool
can be a good thing in that it reflects the company preserving ownership in negotiations
with investors.
The size of the pool may be increased later.

### Counting Shares

There are some key subtleties you’re likely to come across in the way
[outstanding shares](#stock-and-shares) are counted:

🄳 Private companies always have what are referred to as **authorized but unissued** shares,
referring to shares that are authorized in legal paperwork but have not actually been
issued. Until they are issued, the
[unissued stock](https://www.investopedia.com/terms/u/unissuedstock.asp) these shares
represent doesn’t mean anything to the company or to shareholders:
no one owns it.

☝️ For example, a corporation might have 100 million *authorized* shares, but will only
have *issued* 10 million shares.
In this example, the corporation would have 90 million *authorized but unissued* shares.
When you are trying to determine what percentage a number of shares represents, you do
*not* make reference to the authorized but unissued shares.

☝️ You actually want to know the total issued shares, but even this number can be
confusing, as it can be computed
[more than one way](http://www.mattbartus.com/option-grants-fully-diluted-or-issued-and-outstanding/).
Typically, people count shares in two ways: *issued and outstanding* and *fully diluted*.

🄳 **Issued and outstanding** refers to the number of shares actually issued by a company to
shareholders, and does not include shares that others may have an option to purchase.

🄳 **Fully diluted** refers to all of the shares that a company has issued, all of the
shares that have been set aside in a stock incentive plan, and all of the shares that
could be issued if all convertible securities (such as outstanding warrants) were
exercised.

A key difference between fully diluted shares and shares issued and outstanding is that
the total of fully diluted shares will include all the shares in the employee option pool
that are reserved but *not yet issued to* employees.

🔹 If you’re trying to figure out the likely percentage a number of shares will be worth
in the future, it’s best to know the number of shares that are fully diluted.

∑ Even the fully diluted number may not take into account outstanding convertible
securities (like convertible notes) that are *waiting* to be converted into stock at a
future milestone.
For a more complete understanding, in addition to asking about the fully-diluted
capitalization you can ask about any convertible securities outstanding that are not
included in that number.

☝️ The terminology mentioned here isn’t universally applied.
It’s worth discussing these terms with your company to be sure you’re on the same page.

🄳 A **capitalization table (cap table)** is a
[table](https://www.investopedia.com/terms/c/capitalization-table.asp) (often a spreadsheet or
other official record) that records the ownership stakes, including number and class of
shares, of all shareholders in the company.
It is updated as stock is granted to new shareholders.[^cooleygoco.p5v68j]

🚧 Better discuss future sources of dilution.
Define convertible securities and convertible notes and “[fully diluted](https://www.lawinsider.com/dictionary/fully-diluted-basis)”
more. Do people say “fully diluted” but not include convertible securities?

### Classes of Stock

🄳 Investors often ask for rights to be paid back first in exchange for their investment.
The way these different rights are handled is by creating different
[**classes of stock**](https://www.upcounsel.com/classes-of-stock). (These are also sometimes
called [**classes of shares**](https://www.investopedia.com/terms/c/class.asp), though that term
has another meaning in the context of mutual funds.)

🄳 Two important classes of stock are
[**common stock**](https://en.wikipedia.org/wiki/Common_stock) and
[**preferred stock**](https://en.wikipedia.org/wiki/Preferred_stock). In general, preferred stock
has “[rights, preferences, and privileges](https://www.americanbar.org/groups/business_law/publications/blt/2014/01/04_bigler/)”
that common stock does not have.
Typically, investors get preferred stock, and founders and employees get common stock (or
stock options).

The exact number of classes of stock and the differences between them can vary company to
company, and, in a startup, these can vary at [each round](#stages-of-a-startup) of funding.

☝️ Another term you’re likely to hear is
[*founders’ stock*](http://www.alleywatch.com/2013/08/what-is-founders-stock-legally/), which is
(usually) common stock allocated at a company’s formation, but otherwise doesn’t have any
different rights from other common stock.[^lsvpwordpr.dgym96]

Although preferred stock rights are too complex to cover fully, we can give a few key
details:

🄳 Preferred stock usually has a
[**liquidation preference (or preference)**](http://www.investopedia.com/terms/l/liquidation-preference.asp),
meaning the preferred stock owners will be paid before the common stock owners when a
[liquidity event](#sales-and-liquidity) occurs, such as if the company is sold or goes public.

🄳 A company is in
[**liquidation overhang**](https://equityzen.com/blog/startup-valuations-and-liquidation-preference-overhang/)
when the value of the company doesn’t reach the dollar amount investors put into it.
Because of liquidation preference, those holding preferred stock (investors) will have to
be paid before those holding common stock (employees).
If investors have put millions of dollars into a company and it’s sold, employees’ equity
won’t be worth anything if the company is in liquidation overhang and the sale doesn’t
exceed that amount.[^avccom2010.zxzhsl]

☝️ The complexities of the liquidation preference are
[infamous](https://venturebeat.com/2010/08/16/beware-the-trappings-of-liquidation-preference/).
It’s worth understanding that investors and entrepreneurs negotiate a lot of the details
around preferences, including:

- The *multiple*, a number designating how many times the investor must be paid back before
  common shareholders receive proceeds.
  (Often the multiple is 1X, but it can be 2X or higher.)

- Whether preferred stock is
  [*participating*](https://en.wikipedia.org/wiki/Participating_preferred_stock), meaning
  investors get their money back and also participate in proceeds from common stock.

- Whether there is a *cap*, which limits the payout if it is participating.

- ∑
  [🔑This primer](https://medium.com/@CharlesYu/the-ultimate-guide-to-liquidation-preferences-478dda9f9332)
  by Charles Yu gives a concise overview.
  Founders and companies are affected significantly and in subtle ways by these
  considerations.
  For example, as lawyer José Ancer points out, common and preferred stockholders are
  typically quite different and their incentives
  [sometimes](http://siliconhillslawyer.com/2017/10/13/common-stock-v-preferred-stock/)
  [diverge](http://siliconhillslawyer.com/2018/02/07/board-works-common-stock/).

- 🚧 What are good resources to mention that describe conversion of preferred stock to
  common stock?

🔹 For the **purposes of an employee who holds common stock**, the most important thing to
understand about preferences is that they’re not likely to matter if a company does well
in the long term.
In that case, every stockholder has valuable stock they can eventually sell.
But if a company fails or [exits](#sales-and-liquidity) for less than investors had hoped,
the preferred stockholders are generally first in line to be paid back.
Depending on how favorable the terms are for the investor, if the company exits at a low
or modest valuation, it’s likely that common shareholders will receive little—or nothing
at all.

## How Equity Is Granted

In this section we’ll lay out how equity is granted in practice, including the
differences, benefits, and drawbacks of common types of equity compensation, including
restricted stock awards, stock options, and restricted stock units (RSUs).
We’ll go over a few less common types as well.
While the [intent](#the-goals-of-equity-compensation) of each kind of equity grant is
similar, they differ in many ways, particularly around how they are
[taxed](#taxes-on-equity-compensation).

Except in rare cases where it may be negotiable, the type of equity you get is up to the
company you work for.
In general, larger companies grant RSUs, and startups grant stock options, and
occasionally executives and very early employees get restricted stock awards.

🚧 Add section on when equity is granted, including plus-ups.

### Restricted Stock Awards

At face value, the most direct approach to equity compensation would be for the company to
award stock to an employee in exchange for work.
In practice, it turns out a company will only want to do this with restrictions on how and
when the stock is fully owned.

Even so, this is actually one of the least common ways to get equity.
We mention it first because it is the simplest form of equity compensation, useful for
comparison as things get more complex.

🄳 A **restricted stock award** is when a company grants someone stock as a form of
compensation. The stock awarded has additional conditions on it, including a vesting
schedule, so is called **restricted stock**. Restricted stock awards may also be called
simply **stock awards** or **stock grants**.

∑ What *restricted* means here is actually
[complex](https://github.com/jlevy/og-equity-compensation/issues/24). It refers to the fact
that the stock (i) has certain restrictions on it (like transfer restrictions) required
for private company stock, and (ii) will be subject to repurchase at cost pursuant to a
vesting schedule.
The repurchase right lapses over the service-based vesting period, which is what is meant
in this case by the stock “vesting.”

☝️ Restricted stock awards are
[not the same](https://www.fool.com/knowledge-center/the-difference-between-a-restricted-stock-unit-res.aspx)
thing as restricted stock units.

Typically, stock awards are limited to executives or very early hires, since once the
value of the shares increases, the tax burden of receiving them (without paying the
company for their value) can be too great for most people.
Usually, instead of restricted stock, an employee will get stock options.

### Stock Options

🄳 [**Stock options**](https://en.wikipedia.org/wiki/Employee_stock_option) are contracts that
allow individuals to buy a specified number of shares in the company they work for at a
fixed price. Stock options are the most common way early-stage companies grant equity.

🄳 A person who has received a stock option grant is not a shareholder until they
**exercise** their option, which means purchasing some or all of their shares at the strike
price. Prior to exercising, an option holder does not have voting rights.

🄳 The **strike price (or exercise price)** is the fixed price per share at which stock can
be purchased, as set in a stock option agreement.
The strike price is generally set lower (often much lower) than what people expect will be
the *future* value of the stock, which means selling the stock down the road could be
profitable.

☝️ *Stock options* is a confusing term.
In investment, an *option* is a right (but not an obligation) to buy something at a
certain price within a certain time frame.
You’ll often see stock options discussed in the context of
[investment](https://www.investopedia.com/terms/s/stockoption.asp). What investors in
financial markets call *stock options* are indeed options on stock, but they are not
*compensatory* stock options awarded for services.
In this Guide, and most likely in any conversation you have with an employer, anyone who
says “stock options” will be referring to compensatory stock options.

☝️ Stock options are not the same as stock;
they are only the *right to buy stock* at a certain price and under a set of conditions
specified in an employee’s stock option agreement.
We’ll get into these conditions next.

∑ Although everyone typically refers to “stock options” in the plural, when you receive a
stock option grant, you are receiving *an option* to purchase a given number of shares.
So technically, it’s incorrect to say someone “has 10,000 stock options.”

It’s best to understand the financial and [tax implications](#taxes-on-isos-and-nsos) before
deciding [when to exercise](#stock-option-scenarios) options.
In order for the option to be tax-free to receive, the strike price must be the fair
market value of the stock on the date the option is granted.

∑ Those familiar with
[stock trading](https://www.investopedia.com/university/stocks/stocks3.asp) (or those with
economics degrees) will tell you about the
[**Black-Scholes model**](https://www.investopedia.com/university/options-pricing/black-scholes-model.asp),
a general mathematical model for determining the value of options.
While theoretically sound, this does not have as much practical application in the context
of employee stock options.

🚧 Any real-world examples or statistics of how low strike price has led to big payoffs?
Also we could mention and relate this to the term *employee stock options (or ESOs)* and
dispel any confusion between ESOs and ESPPs.

### Vesting and Cliffs

🄳 **Vesting** is the process of gaining full legal rights to something.
In the context of compensation, founders, executives, and employees typically gain rights
to their grant of equity incrementally over time, subject to restrictions.
People may refer to their shares or stock options vesting, or may say that a person is
vesting or has fully vested.

🄳 In the majority of cases, vesting occurs incrementally over time, according to a
**vesting schedule**. A person vests only while they work for the company.
If the person quits or is terminated immediately, they get no equity, and if they stay for
years, they’ll get most or all of it.

Awards of stock, stock options, and RSUs are almost always subject to a vesting schedule.

🄳 Vesting schedules can have a **cliff** designating a length of time that a person must
work before they vest at all.

For example, if your equity award had a one-year cliff and you only worked for the company
for 11 months, you would not get anything, since you haven’t vested in any part of your
award. Similarly, if the company is sold within a year of your arrival, depending on what
your paperwork says, you may receive nothing on the sale of the company.

A very common vesting schedule is vesting over **4 years**, with a **1 year** cliff.
This means you get 0% vesting for the first 12 months, 25% vesting at the 12th month, and
1/48th (2.08%) more vesting each month until the 48th month.
If you leave just before a year is up, you get nothing, but if you leave after 3 years,
you get 75%.

🄳 In some cases, vesting may be triggered by specific events outside of the vesting
schedule, according to contractual terms called **accelerated vesting (or acceleration)**.
Two kinds of accelerated vesting that are commonly negotiated are if the company is sold
or undergoes a merger (**single trigger**) or if it’s sold and the person is fired (**double
trigger**).

🌪 Cliffs are an important topic.
When they work well, cliffs are an effective and reasonably fair system to both employees
and companies.
But they can be abused and their complexity can lead to misunderstandings:

- The intention of a cliff is to make sure new hires are committed to staying with the
  company for a significant period of time.
  However, the flip side of vesting with cliffs is that if an employee is leaving—quits or
  is laid off or fired—just short of their cliff, they may walk away with no stock ownership
  at all, sometimes through no fault of their own, as in the event of a family emergency or
  illness. In situations where companies fire or lay off employees just before a cliff, it
  can easily lead to hard feelings and even lawsuits (especially if the company is doing
  well enough that the stock is worth a lot of money).[^inccombusi.oldydy][^bloombergc.a48epn]
- 🔹 As a manager or founder, if an employee is performing poorly or may have to be laid
  off, it’s both thoughtful and wise to let them know what’s going on well before their
  cliff.
- ∑ Founders often have vesting on their stock themselves.
  As entrepreneur Dan Shapiro explains, this is often for
  [good reason](http://www.danshapiro.com/blog/2012/04/vesting-is-a-hack/).
- 🔹 As an employee, if you’re leaving or considering leaving a company before your vesting
  cliff is met, consider waiting.
  Or, if your value to the company is high enough, you might
  [negotiate](https://www.businessinsider.com/everything-you-need-to-know-about-cliff-vesting-2011-5)
  to get some of your stock “[vested up](https://www.foley.com/when-should-vesting-of-equity-grants-accelerate-06-19-2014/)”
  early. Your manager may well agree that is is fair for someone who has added a lot of
  value to the company to own stock even if they leave earlier than expected, especially for
  something like a family emergency.
  These kinds of vesting accelerations are entirely discretionary, however, unless you
  negotiated for special acceleration in an employment agreement.
  Such special acceleration rights are typically reserved for executives who negotiate their
  employment offers heavily.
- 🚧 How does taking time off, for example a leave of absence, affect the vesting schedule?
- Acceleration when a company is sold (called
  [*change of control*](http://stockoptioncounsel.com/blog/change-of-control-terms-for-startup-stock-options-restricted-stock-and-rsus/2018/6/4)
  terms) is common for founders and not so common for employees.
  It’s worth understanding acceleration and triggers in case they show up in your option
  agreement, but these may not be something you can negotiate unless you are going to be in
  a key role.
- Companies may impose additional restrictions on stock that is vested.
  For example, your shares are very likely subject to a right of first refusal, which means
  that you can’t sell the stock without offering it first to the company.
  And it can happen that companies reserve the right to
  [repurchase](https://www.forbes.com/sites/dianahembree/2018/01/10/startup-employee-alert-can-your-company-take-back-your-vested-stock-options/#75fb48ee6e49)
  vested shares in certain events.

🚧 Can we give any examples here?

### How Options Expire

🄳 The **exercise window (or exercise period)** is the period during which a person can buy
shares at the strike price.
Options are only exercisable for a fixed period of time, until they expire, typically
seven to ten years as long as the person is working for the company.
But this window is not always open.

❗ **Expiration after termination.**
Options can expire after you quit working for the company.
Often, the expiration is **90 days** after termination of service, making the options
effectively worthless if you cannot exercise before that point.
As we’ll get into later, you need to understand the costs, [taxes](#taxes-on-isos-and-nsos),
and tax [liabilities](#the-amt-trap) of exercise and to plan ahead.
In fact, you can find out when you are granted the options, or better yet, before you sign
an offer letter.

🔹 **Longer exercise windows.**
Recently (since around 2015) a few companies are finding ways to keep the exercise window
open for years after leaving a company, promoting this practice as fairer to employees.
Companies with
[extended exercise windows](https://github.com/holman/extended-exercise-windows) include
Amplitude,[^amplitudec.fvea8b] Clef,[^githubcomc.ygtolb] Coinbase,[^mediumcomb.nqs9mo] Pinterest,[^fortunecom.nnfd6o] and Quora.[^quoracomwh.4dxi02]
However, the 90-day exercise window remains the norm.

🌪 **The exercise window debate.**
Whether to have extended exercise windows has been debated at significant length.
Some believe extended exercise windows are
[the future](https://triplebyte.com/blog/extending-stock-option-exercise-window-guide#.12rv7ovrv),
arguing that a shorter window makes a company’s success a
[punishment](http://stockoptioncounsel.com/blog/nc7go8ivzxb1el5rhv6nltrjan0n2t/2017/3/6) to
early employees.

Key considerations include:

- Everyone agrees that employees holding stock options with an expiring window often have to
  make a painful choice if they wish to leave:
  Pay for a substantial tax bill (perhaps five to seven figures) on top of the cost to
  exercise (possibly looking for [secondary liquidity or a loan](#can-you-sell-private-stock))
  or walk away from the options.
- Many familiar with this situation have spoken out
  [forcefully](https://zachholman.com/posts/fuck-your-90-day-exercise-window/) against shorter
  exercise windows, arguing that an employee can help grow the value of a company
  substantially—often having taken a lower salary in exchange for equity—but end up with
  [no ownership](https://triplebyte.com/blog/fixing-the-inequity-of-startup-equity) because
  they’re unable or unwilling to stay for the several years [typically needed](#ipos) before an
  IPO or sale.
- On the other side, a few companies and investors
  [stand by](https://a16z.com/2016/06/23/options-timing/) the existing system, arguing that it
  is better to incentivize people not to leave a company, or that long windows effectively
  transfer wealth from employees who commit long-term to those who leave.
- Some focused on the legalities also argue that it’s a legal requirement of ISOs to have a
  90-day exercise window.
  While this is technically true, it’s not the
  [whole story](https://news.ycombinator.com/item?id=9254299). It is possible for companies to
  extend the exercise window by changing the nature of the options (converting them from
  ISOs to NSOs) and [many companies](https://github.com/holman/extended-exercise-windows) now
  choose to do just that.
- Another path is to
  [split the difference](http://stockoptioncounsel.com/blog/early-expiration-of-startup-stock-options-part-2-the-full-10-year-term-solution/2017/3/28)
  and give extended windows only to longer-term employees.
- Taken together, it’s evident many employees have not been clear on the nuances of this
  when joining companies, and some have
  [🔑suffered](https://medium.com/@ben_mathes/90-days-and-my-six-figure-mistake-a495f4a188e2)
  because of it.
  With the risks of short exercise windows for employees becoming more widely known, longer
  exercise windows are gradually becoming more prevalent.
  As an employee or a founder, it is fairer and wiser to understand and negotiate these
  things up front, and avoid unfortunate surprises.

☝️ Options granted to advisors typically vest over a shorter period than employee grants,
often one to two years.
Advisor grants also typically have a longer exercise window post termination of service,
and will usually have single trigger acceleration on an acquisition, because no one
expects advisors to stay on with a company once it’s acquired.
Typical terms for advisors, including equity levels, are available in the
[📥Founder/Advisor Standard Template (FAST)](https://fi.co/contents/fast#), from the Founder
Institute.

### Kinds of Stock Options

🄳 Compensatory stock options come in two flavors, **incentive stock options (ISOs)** and
**non-qualifying stock options (NQOs, or NQSOs)**. Confusingly, lawyers and the IRS use
[several names](https://www.irs.gov/taxtopics/tc427) for these two kinds of stock options,
including **statutory stock options** and **non-statutory stock options (or NSOs)**,
respectively.

In this Guide, we refer to ISOs and NSOs.

- Companies generally decide to give ISOs or NSOs depending on the legal advice they get.
  It’s rarely up to the employee which they will receive, so it’s best to know about both.
  There are pros and cons of each from both the recipient’s and the company’s perspective.
- ISOs are common for employees because they have the possibility of being more favorable
  from a tax point of view than NSOs.
- 🔸 ISOs can only be granted to employees (not independent contractors or directors who are
  not also employees).
- But ISOs have a number of limitations and conditions and can also create difficult
  [tax consequences](#taxes-on-isos-and-nsos).

### Early Exercise

🄳 Sometimes, to help reduce the tax burden on stock options, a company will make it
possible for option holders to **early exercise (or forward exercise)** their options, which
means they can exercise even before they vest.
The option holder becomes a stockholder sooner, after which the vesting applies to actual
stock rather than options.
This will have [tax implications](#83b-elections).

🔸 However, the company has the right to repurchase the *unvested* shares, at the price
paid or at the fair market value of the shares (whichever is lower), if a person quits
working for the company.
The company will typically repurchase the unvested shares should the person leave the
company before the stock they’ve purchased vests.

### Restricted Stock Units

While stock options are the most common form of equity compensation in smaller private
companies, RSUs have become the most common type of equity award for public and large
private companies.
Facebook pioneered the use of RSUs as a private company to allow it to avoid having to
register as a public company earlier.

🚧 Why? More links on history of RSUs and Facebook story?

🄳
[**Restricted stock units (RSUs)**](http://www.investopedia.com/terms/r/restricted-stock-unit.asp)
refer to an agreement by a company to issue an employee shares of stock or the cash value
of shares of stock on a future date.
Each unit represents one share of stock or the cash value of one share of stock that the
employee will receive in the future.
(They’re called *units* since they are neither stock nor stock options, but another thing
altogether that is contractually linked to the value of stock.)

🄳 The date on which an employee receives the shares or cash payment for RSUs is known as
the **settlement date**.

- 🔸 RSUs may vest according to a vesting schedule.
  The settlement date may be the time-based vesting date or a later date based on, for
  instance, the date of a company’s IPO.
- RSUs are difficult in a startup or early stage company because when the RSUs vest, the
  value of the shares might be significant, and taxes will be owed on the receipt of the
  shares.[^thestartup.tn6iyt] This is not a bad result when the company has sufficient capital to help the
  employee make the tax payments, or the company is a public company that has put in place a
  program for selling shares to pay the taxes.
  But for cash-strapped private startups, neither of these are possibilities.
  This is the reason most startups use stock options rather than RSUs or stock awards.
- RSUs are often considered less preferable to grantees since they remove control over when
  you owe tax. Options, if granted with an exercise price equal to the fair market value of
  the stock, are not taxed until exercise, an event under the control of the optionee.
  If an employee is awarded an RSU or restricted stock award which vests over time, they
  will be taxed on the vesting schedule;
  they have been put on “autopilot” with respect to the timing of the tax event.
  If the shares are worth a lot on the date of vesting, the tax burden can be significant.
- ☝️ You don’t want to confuse *restricted stock units* with *restricted stock*, which
  typically refers to restricted stock awards.

### Less Common Types of Equity

While most employee equity compensation takes the form of stock, stock options, or RSUs, a
complete tour of equity compensation must mention a few less common forms.

🄳 **Phantom equity** is a type of compensation award that references equity, but does not
entitle the recipient to actual ownership in a company.
These awards come under a variety of different monikers, but the key to understanding them
is knowing that they are really just cash bonus plans, where the cash amounts are
determined by reference to a company’s stock.
Phantom equity can have significant value, but may be perceived as less valuable by
workers because of the contractual nature of the promises.
Phantom equity plans can be set up as purely discretionary bonus plans, which is less
attractive than owning a piece of something.

Two examples of phantom equity are phantom stock and stock appreciation rights:

🄳 A
[**phantom stock**](http://www.investopedia.com/articles/stocks/12/introduction-phantom-stock.asp)
award is a type of phantom equity that entitles the recipient to a payment equal to the
value of a share of the company’s stock, upon the occurrence of certain events.

🄳
[**Stock appreciation rights (SARs)**](https://www.nceo.org/articles/phantom-stock-appreciation-rights-sars)
are a type of phantom equity that gives the recipient the right to receive a payment
calculated by reference to the appreciation in the equity of the company.

🚧 Elaboration needed on what events typically trigger phantom stock.
More data on how rare these are?
And what is appreciation?

🄳 [**Warrants**](https://en.wikipedia.org/wiki/Warrant_%28finance%29) are another kind of option
to purchase stock, generally used in investment transactions (for example, in a
convertible note offering, investors may also get a warrant, or a law firm may ask for one
in exchange for vendor financing).
They differ from stock options in that they are more abbreviated and stand-alone legal
documents, not granted pursuant to a single legal agreement (typically called a “[plan](#documents-and-agreements)”)
for all employees.

Employees and advisors may not encounter warrants, but it’s worth knowing they exist.

## Tax Basics

The awarding of equity compensation can give rise to multiple types of taxes for the
recipient, including federal and state income taxes and employment taxes.
There’s a lot that you have to be aware of. [Skip ahead](#taxes-on-equity-compensation) to
understand how taxes on equity work, but if you have time, this section gives a technical
summary of tax fundamentals, just in case you never really figured out all the numbers on
your pay stub.

You don’t need to know every detail, and can rely on software and professionals to
determine the tax you owe, but we do suggest understanding the different kinds of taxes,
how large they can be, and how each is “triggered” by different events.

Given the complexity, most taxpayers aren’t aware of exactly how their tax is calculated.
It does take up thousands of pages[^slatecomar.qqwwen] of the federal tax code and involves the intricate
diversity of state tax law as well.[^gpogovfdsy.clz3vr]

☝️ If you’re already familiar with tax terminology, this section may not have any major
surprises. But for those who are not used to it, watch out:
Many terms sound like regular English, but they’re not. *Ordinary income*, *long-term* and
*short-term*, *election*, *qualified small business*, and other phrases have very specific
meanings we’ll do our best to spell out.

### Kinds of Income

🄳 **Income** is the money an individual makes.
For tax purposes, there are two main types of income, which are taxed differently.
[**Ordinary income**](https://www.investopedia.com/terms/o/ordinaryincome.asp) includes wages,
salary, bonuses and interest made on investments.
[**Capital gains**](https://www.investopedia.com/terms/c/capital_gains_tax.asp) are the profits an
individual makes from selling assets, including stock.

One key difference between ordinary income and capital gains is that when capital gains
taxes are calculated, consideration is given not just to the sale price of the asset but
to the total gain or loss the investment incurred, each outcome having significantly
different tax consequences.

🄳 Capital gains are classified as long-term or short-term. **Long-term capital gains** are
the profits an individual makes from selling assets, such as stock, a business, a house,
or land, that were held for more than a year. **Short-term capital gains** are profits from
the sale of assets held for less than a year.

Although this topic is not without
[💰controversy](https://www.wsj.com/articles/how-should-capital-gains-be-taxed-1425271052),
the general idea is, if you are selling something you’ve owned for a long time, you can be
taxed a lower rate.

All these rates have evolved over time based on economic and political factors,[^taxpolicyc.sjye20] so you
can be confident they will change again in the future.

📰 In 2017, Congress passed the
[Tax Cuts and Jobs Act](https://en.wikipedia.org/wiki/Tax_Cuts_and_Jobs_Act_of_2017) (TCJA),
which made
[many changes](https://heritageinvestment.com/wp-content/uploads/2018/01/TCJA-HIG-Old-vs.-New-Comparison.pdf)
to tax rates for the **2018** tax year.
Long-term capital gains taxes did
[not change](https://www.marketwatch.com/story/your-simple-guide-to-the-new-capital-gains-tax-rates-2018-04-16)
significantly.

🚧 Can we clarify the term *investment income* too?

### Federal Taxes

🄳 **Income tax** is the money paid by individuals to federal, state, and, in some cases,
local governments, and includes taxation of ordinary income and capital gains.
Generally, U.S. citizens, residents, and some
[foreigners](https://www.irs.gov/individuals/international-taxpayers/nra-withholding) must
[file](https://www.irs.gov/pub/irs-pdf/p17.pdf) and pay federal income tax.

🔹 In general, federal tax applies to many
[kinds of income](https://www.irs.gov/taxtopics/tc400.html). If you’re an employee at a
startup, you need to consider four kinds of federal tax, each of which is computed
differently.

☝️ When it comes to equity compensation, it’s possible that you’ll have to worry about
*all of these*, depending on your situation.
That’s why we have a lot to cover here:

🄳 **Ordinary income tax** is the tax on wages or salary income, and short-term investment
income. The term **short-term capital gains tax** may be applied to taxes on assets sold
less than a year from purchase, but profits from these sales are taxed as ordinary income.
For a lot of people who make most of their money by working, ordinary income tax is the
biggest chunk of tax they pay.

🄳 **Employment taxes** are an additional kind of federal tax beyond ordinary income tax,
and consist of Social Security and
[Medicare taxes](https://www.irs.gov/businesses/small-businesses-self-employed/questions-and-answers-for-the-additional-medicare-tax)
that are withheld from a person’s paycheck.
Employment taxes are also referred to as
[**payroll taxes**](https://en.wikipedia.org/wiki/Payroll_tax) as they often show up on employee
pay stubs. The Social Security wage withholding rate in 2018 is 6.2% up to the FICA wage
base. The Medicare component is 1.45%, and it does not phase out above the FICA wage base.

- 🚧 Review and add more links on SS and Medicare taxes.

🄳 **Long-term capital gains tax** is a tax on the sale of assets held longer than a year.
Long-term capital gains tax is often lower than ordinary income tax.
Many investors hold assets for longer than a year in order to qualify for the lesser tax
burden of long-term capital gains.

🄳 **Alternative minimum tax (AMT)** is a
[supplemental income tax](https://en.wikipedia.org/wiki/Alternative_minimum_tax) that applies
to certain individuals in some situations.
This type of tax does not come up for many taxpayers, but higher income earners and people
in special situations may have to pay large AMT bills.
AMT was first enacted in 1979 in response to reports that 155 wealthy individuals had paid
no income tax in 1966.[^taxpolicyc.mgorf1] It is not the same as ordinary income tax or employment tax, and
is calculated according to its
[own rules](https://www.nerdwallet.com/blog/taxes/alternative-minimum-tax-amt/).

🚧 What is the history and motivation of AMT?

❗ AMT is relevant to you if you’re reading this.
It’s important to understand because exercising ISOs can trigger AMT. In some cases a *lot*
of AMT, *even when you haven’t sold the stock* and have no money to pay.
We discuss this [later](#the-amt-trap).

#### Figure: Bracke Rates, Income, and Taxes

```hlwy-infographics
{
  "name": "TaxRates",
  "data": {
    "rates": [
      {
        "rate": 0.1,
        "single": 0,
        "married": 0,
        "hoh": 0
      },
      {
        "rate": 0.12,
        "single": 9525,
        "married": 19050,
        "hoh": 13600
      },
      {
        "rate": 0.22,
        "single": 38700,
        "married": 77400,
        "hoh": 51800
      },
      {
        "rate": 0.24,
        "single": 82500,
        "married": 165000,
        "hoh": 82500
      },
      {
        "rate": 0.32,
        "single": 157500,
        "married": 315000,
        "hoh": 157500
      },
      {
        "rate": 0.35,
        "single": 200000,
        "married": 400000,
        "hoh": 200000
      },
      {
        "rate": 0.37,
        "single": 500000,
        "married": 600000,
        "hoh": 500000
      }
    ],
    "deductions": {
      "single": 0,
      "married": 0,
      "hoh": 0
    }
  }
}
```

```hlwy-infographics
{
  "name": "TaxRates",
  "data": {
    "rates": [
      {
        "rate": 0,
        "single": 0,
        "married": 0,
        "hoh": 0
      },
      {
        "rate": 0.15,
        "single": 38600,
        "married": 77200,
        "hoh": 51700
      },
      {
        "rate": 0.2,
        "single": 425801,
        "married": 479001,
        "hoh": 452401
      }
    ],
    "deductions": {
      "single": 0,
      "married": 0,
      "hoh": 0
    }
  }
}
```

🄴 *Source: IRS and the
[Tax Foundation](https://files.taxfoundation.org/20180207142513/TaxFoundation-FF567-Updated.pdf)*

A bit on how all this fits together:

- Ordinary income tax applies in the situations you’re probably already familiar with, where
  you pay taxes on [salaries or wages](https://www.irs.gov/taxtopics/tc401.html). Tax rates are
  based on [filing status](https://www.irs.gov/newsroom/choosing-the-correct-filing-status) (if
  you are single, married, or support a family), and on which
  [**income bracket**](https://taxfoundation.org/2018-tax-brackets) you fall under.
- **Income brackets.**
  For ordinary income, as of the **2018** tax year, there are income brackets at **10%**, **12%**,
  **22%**, **24%**, **32%**, **35%**, and **37%**
  [marginal tax rates](http://www.investopedia.com/terms/m/marginaltaxrate.asp)—see
  [Notice 1036](https://www.irs.gov/pub/irs-pdf/n1036.pdf) or a Tax Foundation
  [summary](https://files.taxfoundation.org/20180207142513/TaxFoundation-FF567-Updated.pdf). Be
  sure you understand how these brackets work, and what bracket you’re likely to be in.
  - ☝️ There is a popular misconception that if you move to a higher bracket, you’ll make less
    money.[^todayyougo.tyjmz8] What actually happens is when you cross certain thresholds, each additional
    (marginal) dollar you make is taxed at a slightly higher rate, equal to the bracket you’re
    in. After you earn more than your deduction, on which you pay no tax, your post-tax income
    looks like the diagram above.
    (More discussion on such misconceptions are in
    [this Reddit thread](https://www.reddit.com/r/personalfinance/comments/2wkbgz/graphing_one_misconception_about_tax_brackets/).)
- Investment gains, such as buying and selling a stock, are similarly taxed at “ordinary”
  rates, unless they are [**long-term**](https://www.irs.gov/taxtopics/tc409.html), which means you
  held the asset for more than a year.
- You also pay a number of other federal taxes (see a
  [📥2018 summary for all states](https://www.adp.com/tools-and-resources/compliance-connection/state-taxes/2018-fast-wage-and-tax-facts.aspx)),
  notably:
  - **6.2%** for Social Security on your first $118,500
  - **1.45%** for Medicare
  - **0.9%**
    [Additional Medicare Tax](https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Questions-and-Answers-for-the-Additional-Medicare-Tax)
    on income over $200,000 (single) or $250,000 (married filing jointly)
  - **3.8%**
    [Net Investment Income Tax](https://www.irs.gov/uac/Newsroom/Net-Investment-Income-Tax-FAQs)
    (NII) (enacted as part of the Affordable Care Act,[^taxpolicyc.w7dds7] also called “Obamacare”) on
    investment income if you make over $200,000 (single) or $250,000 (married filing jointly).[^investoped.s08hcp]
- Ordinary federal income tax, Social Security, and Medicare taxes are withheld from your
  paycheck by your employer and are called
  [**employment taxes**](https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Understanding-Employment-Taxes).
- 🔹 Long-term capital gains are taxed at a lower rate than ordinary income tax: **0%**, **15%**,
  or **20%**.[^foolcomtax.ox10ej] This covers cases where you get dividends or sell stock after holding it a
  year. If you are in the middle brackets (more than about $37K and less than $413K of
  ordinary income), your long-term capital gains rate is 15%. You can find more detail on
  tax brackets at the [Tax Foundation](https://taxfoundation.org/2018-tax-brackets/).
- [AMT](http://fairmark.com/general-taxation/alternative-minimum-tax/alternative-minimum-tax-101/)
  is a [complex part](https://www.irs.gov/taxtopics/tc556.html) of the federal tax code most
  taxpayers don’t worry about.
  But it comes into play when [exercising ISOs](#the-amt-trap). Most people do not pay AMT
  unless it is “triggered” by specific
  [situations](https://www.marketwatch.com/story/meet-the-new-friendlier-alternative-minimum-tax-2018-02-26),
  typically high income (more than $500K) or high deductions.
  Whether you pay AMT also depends on the state in which you file, since your state taxes
  can significantly affect your deductions.
  If you are affected, AMT tax rates are usually at **26%** or **28%** marginal tax rate, but
  effectively **35%** for some ranges, meaning it is higher than ordinary income tax for some
  incomes and lower for others.[^foolcomtax.3ka4p1]
  AMT rules are so complicated you often need professional tax help if they might apply to
  you. The IRS’s
  [AMT Assistant](https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Alternative-Minimum-Tax-(AMT)-Assistant-for-Individuals)
  might also help.
- 🔹 [Section 1202](https://www.investopedia.com/terms/s/section-1202.asp) of the Internal
  Revenue Code provides a special tax break for qualified small business stock held for more
  than five years.[^blogwealth.3vcf24]
  Currently, this tax break is a 100% exclusion from income for up to $10M in gain.
  There are also special rules that enable you to rollover gain on qualified small business
  stock you have held for less than five years.
  Stock received on the exercise of options can qualify for the Section 1202 stock benefit.
- 🚧 Fill in details on QSBS. Move this elsewhere?
  Good readings on this?

### State Taxes

State tax rates and rules
[vary significantly](https://taxfoundation.org/state-individual-income-tax-rates-brackets-2018/).
Since federal rates are much higher than state rates, you usually think of federal tax
planning first.
But you should also know a bit about tax rates in your state.

State long-term capital gains rates range widely.
California has the highest, at **13.3%**; several states have none.[^foolcomper.bw6uel]

🔹 For this reason, some people even
[consider moving](https://www.forbes.com/sites/robertwood/2016/05/17/can-you-avoid-california-taxes-by-moving/#316bd9471694)
to another state if they are likely to have a windfall gain, like selling a lot of stock
after an IPO.

🚧 How do you determine to what state you owe taxes?
Any good resources on this?

## Taxes on Equity Compensation

Equity and taxes interact in complicated ways, and the tax consequences for an employee
receiving restricted stock, stock options, or RSUs are dramatically different.
This section will cover these messy details and help you make decisions that reduce the
tax burden of your equity compensation.

### 83(b) Elections

This section covers one of the most important and complex decisions you may need to make
regarding stock awards and stock options:
paying taxes early with an 83(b) election.

- Generally, restricted stock is taxed as ordinary income
  [*when it vests*](http://www.investopedia.com/articles/tax/09/restricted-stock-tax.asp?performancelayout=true).
- If the stock is in a startup with low value, this may not result in high tax.
  If it’s been years since the stock was first granted and the company is now worth a lot,
  the taxes owed could be quite significant.

🄳 The Internal Revenue Code, in
[Section 83(b)](https://www.law.cornell.edu/uscode/text/26/83), offers taxpayers receiving
equity in exchange for work the option to pay taxes on their options before they vest.
If qualified, a person can tell the IRS they prefer this alternative in a process called
an
[**83(b) election**](http://acceleratedvesting.com/what-is-an-83b-election-and-when-do-i-make-it-part-1-with-graphic/).
Paying taxes early with an 83(b) election can potentially reduce taxes significantly.
If the shares go up in value, the taxes owed at vesting might be far greater than the
taxes owed at the time of receipt.

- ☝️ Why is it called an *election*? Because you are *electing* (choosing) to pay taxes
  early in exchange for this treatment by the IRS. Does the IRS secretly enjoy making simple
  concepts sound confusing?
  We’re not sure.
- An 83(b) election isn’t guaranteed to reduce your taxes, however.
  For example, the value of the stock may not increase.
  And if you leave the company before you vest, you *don’t* get back the taxes you’ve
  already paid.
- ❗ You must file the 83(b) election yourself with the IRS
  [**within 30 days**](https://www.irs.gov/irb/2012-28_IRB/ar12.html) of the grant or exercise, or
  the opportunity is irrevocably lost.
- ☝️ Note an 83(b) election is made on receipt of actual shares of stock.
  Technically, it cannot be made on the receipt of a stock *option* itself:
  You first must exercise that option, then file the election.
- If you receive an early exercisable stock option (when you don’t have to wait for the the
  stock to vest), you can make an 83(b) election upon receipt of the exercised shares.
- Section 83(b) elections do not apply to vested shares;
  the election only applies to stock that is not yet vested.
  Thus, if you receive options that are *not* early exercisable (meaning you have to wait
  until they vest to exercise), an 83(b) election would not apply.
- 🔹 Founders and very early employees will almost always want to do an 83(b) election upon
  the receipt of unvested shares, since the stock value is probably low.
  If the value is really low, and the taxes owed are not that great, you can make the
  election without having to pay much tax and start your capital gains holding period on the
  shares.
- 🚧 Clarify here which types of equity compensation the 83b can apply to.

📰 With the passage of the
[Tax Cuts and Jobs Act](https://en.wikipedia.org/wiki/Tax_Cuts_and_Jobs_Act_of_2017) (TCJA) in
2017, Congress approved a
[**new Section 83(i)**](https://www.wsgr.com/WSGR/Display.aspx?SectionName=publications/PDFSearch/wsgralert-section-83i.htm)
that is intended to allow deferral of tax until RSU and stock option holders can sell
shares to pay the tax bill.
Whether companies will choose or be able to make this available to employees is
[not clear](http://stockoptioncounsel.com/blog/tax-deferred-option-exercises-under-the-new-section-83i-tax-cuts-and-jobs-act-of-2017)
yet.

### 409A Valuations

When a person’s stock vests, or they exercise an option, the IRS determines the tax that
person owes. But if no one is buying and selling stock, as is the case in most startups,
then the value of the stock—and thus any tax owed on it—is not obvious.

🄳 The **fair market value (FMV)** of any good or property refers to a price upon which the
buyer and seller have agreed, when both parties are willing, knowledgeable, and not under
direct pressure to carry out the exchange.
The fair market value of a company’s stock refers to the price at which a company will
issue stock to its employees, and is used by the IRS to calculate how much tax an employee
owes on any equity compensation they receive.
The FMV of a company’s stock is determined by the company’s most recent 409A valuation.

🄳 A
[**409A valuation**](http://www.fenwick.com/FenwickDocuments/409_Valuations_Stock_Options.pdf) is
an assessment private companies are required by the IRS to conduct regarding the value of
any equity the company issues or offers to employees.
A company wants the 409A to be low, so that employees make more off options, but not so
low the IRS won’t consider it reasonable.
In order to minimize the risk that a 409A valuation is manipulated to the benefit of the
company, companies hire independent firms to perform 409A valuations, typically annually
or after events like fundraising.

The 409A valuation of employee equity is usually much less than what investors pay for
preferred stock;
often, it might be only a third or less of the preferred stock price.

🌪 Although the 409A process is required and completely standard for startups, the
practice is a strange mix of formality and complete guesswork.
It has been called “quite precise—remarkably inaccurate,” by venture capitalist Bill
Gurley. You can read more about its
[nuances and controversies](https://www.nytimes.com/2017/03/08/business/dealbook/valuation-shell-game-silicon-valleys-dirty-secret.html).

- 🚧 More on when 409As happen.

- A 409A does have to happen every 12 months to grant the company safe harbor.
  - A 409A has to be done after any event that could be deemed a “material event,” which is a
    fancy way of saying any event that could change the price or value of the company
    meaningfully. Other examples could be if a CEO leaves, if the company starts making a ton
    of money, or an acquisition.

- ∑ “FMV” is a legal term defined in Supreme Court Case 546,
  [United States vs. Cartwright](https://scholar.google.com/scholar_case?case=4964174066744569590&hl=en&as_sdt=6&as_vis=1&oi=scholarr#p551).

- ∑ “409A” is a reference to the
  [section](https://en.wikipedia.org/wiki/Internal_Revenue_Code_section_409A) of the Internal
  Revenue Code that sets requirements for options to be tax-free on grant.

### Taxes on ISOs and NSOs

Typically, early to mid-stage companies grant stock options, which may be
[ISOs or NSOs](#kinds-of-stock-options).

- ❗When you get stock options and are considering if and when to exercise, you need to think
  about the taxes and **when you owe them**. In principle, you need to think about taxes you
  may incur at three points in time:
  - at **time of grant**
  - at **time of exercise**
  - at **time of sale**
- These events trigger ordinary tax (high), long-term capital gains (lower), or AMT
  (possibly high) taxes in different ways for NSOs and ISOs.

🄳 The taxes at time of exercise will depend on the gain between the strike price and the
FMV, known as the **spread** or the
[**bargain element**](http://www.investorwords.com/5414/bargain_element.html).

- 🔹 If you’re granted ISOs or NSOs at a low strike price, and the bargain element is zero,
  then you may be able to exercise at a reasonable price without triggering taxes at all.
  So assuming the company allows it, it makes sense to early exercise *immediately* (buying
  most or all of the shares, even though they’re not vested yet) and simultaneously file an
  83(b) election.
- 🔸 An 83(b) election, as already discussed, is the choice to be taxed on the receipt of
  property even though you might have to forfeit or give back the property to the company.
  You can make an election on the receipt of stock, but you cannot make the election on the
  receipt of a stock option or an RSU because options and RSUs are not considered property
  for the purposes of Section 83(b).
- 🚧 Move or remove this note, as it’s covered earlier?
- 🔸 ISOs are often preferred by startups, as they’re supposedly better for employees from a
  tax perspective.
  This assumes that (1) AMT won’t be triggered and (2) you’ll get a low long-term capital
  gains rate by holding the stock for the appropriate holding periods.
  However, often you either run afoul of the AMT trap, or don’t hold the stock long enough
  with the complicated 1 year + 2 year requirement, or the spread at exercise is small or
  zero, so the difference wouldn’t matter anyway.
  NSOs do have a slightly higher tax because of the need to pay employment taxes on NSOs and
  not ISOs.
- 🌪 Overall, it’s not clear the ISO is that much better for employees, so
  [many people](http://www.business2community.com/finance/nsos-better-isos-0826167#fz1HTCiOQxRyTr62.97)
  argue [for NSOs](http://www.startuplawblog.com/2010/08/11/top-reasons-nqos-over-isos/)
  instead.
- ☝️ This is partly because ISOs can make it harder to meet the long-term capital gains
  holding period.[^thestartup.25gj0l]
  Many people expect early exercise, together with an 83(b) election, will help them hold
  the stock long enough to qualify for long-term capital gains.
  While this is true for NSOs, a murky part of the rules on ISOs states that even with an
  83(b) election, the capital gains holding period does not begin until the shares actually
  vest. So if you want to immediately exercise an option and file a Section 83(b) election,
  and you might have liquidity soon, it’s better—for those who can—to do so with NSOs.

### The AMT Trap

When it comes to taxes and equity compensation, one scenario is so dangerous we give it
its own section.

❗ If you have received an ISO, exercising it may unexpectedly trigger a big AMT bill—even
before you actually make any money on a sale!
If there is a large spread between the strike price and the 409A valuation, you are
potentially on the hook for an enormous tax bill, even if you can’t sell the stock.
This has pushed people into bankruptcy.
It also caused Congress to grant a one-time forgiveness, the odds of which happening again
are very low.

🄳 The catastrophic scenario where exercising ISOs triggers a large AMT bill, with no
ability to sell the stock to pay taxes, is sometimes called the **AMT trap**. This
[infamous](https://www.nceo.org/articles/stock-options-alternative-minimum-tax-amt) problem
has trapped many employees and
[bankrupted](http://blog.sfgate.com/dgreenberg/2012/06/22/tax-advice-from-the-dot-com-bubble-beware-of-isos/)
people during past dot-com busts.
Now more people know about it, but it’s still a significant obstacle to plan around.

📰 In 2017, Congress passed the
[Tax Cuts and Jobs Act](https://en.wikipedia.org/wiki/Tax_Cuts_and_Jobs_Act_of_2017) (TCJA),
which increases AMT exemptions and their phaseout thresholds.
This means fewer people will be affected by AMT in 2018 than in prior years.[^mediumcomb.57vdab]

Note that if your AMT applies to events prior to 2008, you’re
[off the hook](http://www.startuplawblog.com/2009/04/03/whoops-i-didnt-pay-amt-on-my-isos-exercised-prior-to-1108-what-do-i-do/).

Understand this topic and talk to a professional if you exercise ISOs.
The AMT trap does not apply to NSOs.

🚧 Links to coverage on Congress’s forgiveness?

### Stock Awards vs. ISOs vs. NSOs

Because the differences are so nuanced, what follows is a summary of the taxes on
restricted stock awards, ISOs, and NSOs, from an employee’s point of view.

- **Restricted stock awards.**
  Assuming vesting, you pay full taxes early with the 83(b) or at vesting:

- At grant:
    - if 83(b) election filed, ordinary tax on FMV
    - none otherwise
  - At vesting:
    - none if 83(b) election filed
    - ordinary tax on FMV of vested portion otherwise
  - At sale:
    - long-term capital gains tax on gain if held for **1 year** past when taken into income
    - ordinary tax otherwise (including immediate sale)

- **NSOs.** You pay full taxes at exercise, and the sale is like any investment gain:

- At grant and vesting:
    - no tax if granted at FMV
  - At exercise:
    - ordinary tax on the bargain element
    - income and employment tax withholding on paycheck
  - At sale:
    - long-term capital gains tax on gain if held for **1 year** past exercise
    - ordinary tax otherwise (including immediate sale)

- **ISOs.** You might pay less tax at exercise, but it’s complicated:

- At grant and vesting:
    - no tax if granted at FMV
  - At exercise:
    - **AMT tax event** on the bargain element
    - no ordinary or capital gains tax
    - no income or employment tax withholding on paycheck
  - At sale:
    - long-term capital gains if held for **1 year** past exercise and **2 years** past grant date
    - ordinary tax otherwise (including immediate sale)

Mary Russell, a lawyer who specializes in equity compensation, recommends each form of
equity be used at the appropriate time in private companies:
restricted stock awards for the earliest stage of a startup, stock options with longer
exercise windows for the early to mid stage, and RSUs for the later stages.[^stockoptio.z54l1t]

If you relish tax complexity, you can learn more from:

- The [Tax Topics](https://www.irs.gov/taxtopics/tc427.html) coverage of ISOs and NSOs from the
  IRS
- Joe Wallin’s posts on the Startup Law Blog, “[Top 6 Reasons To Grant NQOs Over ISOs](http://www.startuplawblog.com/2010/08/11/top-reasons-nqos-over-isos/)”
  and “[Incentive Stock Options vs. Nonqualified Stock Options](http://www.startuplawblog.com/2013/05/15/incentive-stock-options-vs-nonqualified-stock-options/)”
- Investopedia’s post “[Get the Most Out of Employee Stock Options](http://www.investopedia.com/articles/optioninvestor/07/esoabout.asp)”
- EquityZen’s summary of the topic, “[Understanding Equity Compensation And What It Means For Startup Employees](https://equityzen.com/blog/understanding-equity-compensation-for-startup-employees/)”

### Taxes on RSUs

If you are awarded RSUs, each unit represents one share of stock that you will be given
when the units vest.

- Here’s the tax summary for RSUs:
  - At grant:
    - no tax
  - At vesting/delivery:
    - ordinary tax on current share value
  - At sale:
    - long-term capital gains tax on gain if held for **1 year** past vesting
    - ordinary tax otherwise (including immediate sale)
- 🔸 When you receive your shares, you are taxed on their value at that time.[^joewallinc.8eaojr]
  If you are an employee, this means you may have to write a check to the company to cover
  your income and employment tax withholding.
  Often, for U.S. employees, companies will withhold the tax in the form of shares such that
  no action is required by the employee at vesting time.[^schwabcomp.94cuxl]
- If you receive an RSU when the stock is of little value, you cannot elect to be taxed on
  the value of that stock when you receive the RSU—you pay taxes at vesting time, based on
  the value of the shares at that time.
- 🔸 RSUs present some big problems in private companies:
  - You will owe tax when you receive the shares, even though they are illiquid.
  - You can’t minimize the tax impact of an increase in value of the underlying shares between
    the date you receive the RSU and the date it is settled.
  - If you are an employee you will have to write a check to the company to satisfy your
    income and employment tax withholding.
- 🔸 RSUs are less attractive than stock options from a tax point of view because you cannot
  make an 83(b) election with respect to RSUs.
  By contrast, if you receive a stock option, as long as it’s priced at fair market value
  you will have no income upon receipt of the options, and your income tax and employment
  tax consequences will be deferred until you exercise, an event under your control for the
  most part.

### Tax Comparison Table

#### Table: Comparing Taxes on Types of Equity Compensation

This table is a summary of the differences in taxation on types of equity compensation.

### Tax Dangers

Because they are so important, we list some costly errors to watch out for when it comes
to taxes on equity compensation:

- ❗ If you are going to file an 83(b) election, it must be **within 30 days** of stock grant
  or option exercise.
  Often, law firms will take a while to send you papers, so you might only have a week or
  two. If you miss this window, it could potentially have giant tax consequences, and is
  essentially an irrevocable mistake—it’s one deadline the IRS won’t extend.
  When you file, get documentation from the post office as well as a delivery confirmation,
  and include a self-addressed, stamped envelope for the IRS to send you a return receipt.
  (Some people are so concerned about this they even ask a friend to go with them to the
  post office as a witness!)
- ❗ Watch out for the AMT trap we’ve already discussed.
- ❗ If you exercise your options, and your income had been from consulting rather than
  employment (1099, not W-2), you will be subject to the
  [self-employment tax](https://www.irs.gov/businesses/small-businesses-self-employed/self-employment-tax-social-security-and-medicare-taxes),
  which consist of both the employer and the employee side of FICA. In addition to owing the
  normal income tax, this means you will owe the Social Security tax component (**6.2%**) up
  to the FICA wage base, and you will owe the Hospital Insurance component (**2.9%**) on all
  of your income.
- ❗ Thoughtfully decide when to exercise options.
  As discussed, if you wait until the company is doing really well, or when you are leaving,
  the delay can have serious downsides.

## Plans and Scenarios

### Evaluating Equity Compensation

Once you understand the [types of equity](#how-equity-is-granted) and their
[tax implications](#taxes-on-equity-compensation), you have many of the tools you need to
evaluate an offer that includes equity compensation, or to evaluate equity you currently
have in a company.

In summary, you have to determine or make educated guesses about several things:

- **Equity value.** This can be estimated by the value the company may have in the future, and
  the number of shares you may own.
  - **Percentage ownership.**
    As we’ve mentioned, knowing how many shares of stock or stock options you have is
    meaningless unless you know the number of outstanding shares.
    What matters is the percentage ownership of the company the shares represent, including
    the [details](#counting-shares) of how the total is counted.
  - **Risk.** It is critical to understand [risk](#stages-of-a-startup) in the business and dilution
    to ascertain the possible future value of equity.
    [This article](http://codingvc.com/valuing-employee-options/) from Leo Polovets provides some
    additional thoughts.
- **Vesting.** Understand [when](#vesting-and-cliffs) you will receive the equity, as well as
  whether you’re able to exercise stock options (and pay the associated costs and taxes),
  and whether you can do all this before your exercise window expires.
- **Liquidity.** Determine when you will be able to [sell your shares](#sales-and-liquidity), and
  if that is likely to be for a profit at that time.
  (We talk about liquidity of private stock next.)
- **Tax.** [Tax concerns](#taxes-on-equity-compensation) are inseparable from the value of equity.
  Know the tax implications of your possible grant, exercise, vesting, and sale, in terms of
  ordinary income tax, employment tax, long-term capital gains, and alternative minimum tax.

That’s a lot, and even so, decisions are uncertain, but it is possible to make much more
informed decisions once you have this information.

### What Is Private Stock Worth?

We now turn to the question of determining the value of private company stock.
We’ve seen how stock in private companies often [can’t be sold](#can-you-sell-private-stock),
so its value is
[difficult to estimate](https://www.investopedia.com/articles/fundamental-analysis/11/valuing-private-companies.asp).

The value of equity you cannot yet sell is a reflection of three major concerns:

1. How well the company is doing now—that is, how profitable it is, or how many customers it
   is attracting.
2. How well the company will perform in the future.
3. How likely it is the company will be valuable as part of another company—that is, whether
   it may be [acquired](#sales-and-liquidity).

The first concern is relatively clear, if you know the company’s financials.
The second and third come down to predictions and are never certain.
In fact, it’s important to understand just how uncertain all three of these estimations
are, depending on the stage of the company.

In earlier stage private companies, there may be little or no profit, but the company may
seem valuable because of high expectations that it can make future profit or be acquired.
If a company like this takes money from investors, the investors determine the price they
pay based on these educated guesses and market conditions.

In startups there tends to be a high degree of uncertainty about the future value of
equity, while in later stage private companies financials are better understood (at least
to investors and others with an inside view of the company), and these predictions are
often more certain.

### Can You Sell Private Stock?

Ultimately, the value of your equity depends on whether and when you are able to convert
it into stock that you sell for cash.
With public companies, the answer is relatively easy to estimate—as long as there are no
restrictions on your ability to sell, you know the current market value of the stock you
own or might own.
What about private companies?

A liquidity event is usually what makes it possible for shareholders in a private company
to sell their stock.
However, individuals may sometimes be able to gain liquidity while a company is still
private.

🄳 A **secondary market (or secondary sale, or private sale)** transaction is when private
company stock [is sold](https://www.cooleygo.com/secondary-sales-of-private-company-stock/)
to another private party.
This is in contrast to **primary market** transactions, where companies sell directly to
investors. Secondary sales are not routine, but they can sometimes occur, such as when an
employee sells to an accredited investor who wants to invest in the company.

🄳 Shares held by an employee are typically subject to a **right of first refusal (ROFR)**
in favor of the company, meaning the employee can’t sell their shares to a third party
without offering to sell their shares to the company first.

🔸 Private sales generally require the agreement and cooperation of the company, for both
contractual and practical reasons.
While those who hold private stock may hope or expect they need only find a willing buyer,
in practice secondary sales only work out in
[a few situations](https://venturebeat.com/2016/12/19/secondary-market-for-shares-in-pre-ipo-unicorns-is-booming/).

Unlike a transaction on a public exchange, the buyer and seller of private company stock
are not in total control of the sale.
There are a few reasons **why companies may not support secondary sales**:

- Historically, startups have seen little purpose in letting current employees sell their
  stock, since they prefer employees hold their stock and work to make it more valuable by
  improving the value of the company as a whole.
- Even if employee retention is not a concern, there are reasons private sales may not be in
  the company’s interest.
  Former employees and other shareholders often have difficulty initiating secondary
  transactions with a company.[^wsjcomarti.vm6qmp]
  Private buyers may ask for the company’s internal financials in order to estimate the
  current and future value of its stock;
  the company may not wish to share this confidential information.
- Companies must
  [consider](https://www.square1bank.com/insights/new-normal-secondaries-409a-valuation-process/)
  whether sales could influence their [409A valuation](#409a-valuations).
- Secondary sales are an administrative and legal burden that may not make it to the top of
  the list of priorities for busy startup CEOs and CFOs.

🔹 However, participation in the secondary market has evolved in recent years,[^techcrunch.qn7usd][^industryve.6prupc][^mediumcomr.ez02hw] and **a few
options may be possible**:

- [SharesPost](http://sharespost.com/), [Equidate](https://www.equidateinc.com/), and
  [EquityZen](https://equityzen.com/) have sought to establish a market around secondary sales,
  particularly for well-known pre-IPO companies.
- A few other secondary firms have emerged that have interest in certain purchases,
  especially for larger secondary sales from founders, early employees, or executives.
  A company can work with a firm to facilitate multiple transactions.
  These firms include [137 Ventures](http://137ventures.com/),
  [ESO Fund](https://employeestockoptions.com/),
  [Akkadian Ventures](https://www.akkadianventures.com/),
  [Industry Ventures](http://www.industryventures.com/), [Atlas Peak](http://www.atlaspeakcap.com/),
  and [Founders Circle](http://www.founderscircle.com/).
- In some cases, an employee may have luck selling stock privately to an individual, like a
  board member or former executive, who wishes to increase their ownership.
  Further discussion can be found
  [on Quora](https://www.quora.com/How-do-employees-in-startups-sell-stock-in-the-secondary-markets).

### Stock Option Scenarios

The key decisions around stock options are when to exercise and, if you can, when to sell.
Here we lay out some common scenarios that might apply to you.
Considering these scenarios and their outcomes can help you evaluate your position and
decide what you should do.

- **Exercise and hold.**
  You can write the company a check and pay any taxes on the spread.
  You are then a stockholder, with a stock certificate that may have value in the future.
  As [discussed](#how-equity-is-granted), you may exercise:
  - Early, even immediately upon grant.
  - Before vesting (if early exercise is available to you).
  - Sometime after vesting.
  - After leaving the company, as long as the exercise window is open.
    - 🔸 Recall that the window is likely to [close soon](#how-options-expire) after you leave a
      company, often 90 days after termination.
- **Wait until acquisition.**
  If the company is acquired for a large multiple of the exercise price, you may then use
  your options to buy valuable stock.
  However, as discussed, your shares could be worth next to nothing unless the sale price
  exceeds the liquidation overhang.
- 🔸 **Secondary market.**
  As [discussed](#can-you-sell-private-stock), in some cases it’s possible to exercise and
  sell the stock in a private company directly to a private party.
  But this generally requires some cooperation from the company and is not something you can
  always count on.
- **Cashless exercise.**
  In the event of an IPO, a broker can allow you to exercise all of your vested options and
  immediately sell a portion of them into the public market, removing the need for cash up
  front to exercise and pay taxes.

🔹 Note that some of these scenarios may require significant cash up front, so it makes
sense to do the math early.
If you are in a tight spot, where you may lose valuable options altogether because you
don’t have the cash to exercise, it’s worth exploring each of the scenarios above, or
combinations of them, such as exercising and then selling a portion to pay taxes.
In addition, there are a [few funds](#can-you-sell-private-stock) and individual investors
who may be able to front you the cash to exercise or pay taxes in return for an agreement
to share profits.

Author and programmer Alex MacCaw
[explores](https://blog.alexmaccaw.com/an-engineers-guide-to-stock-options#exercising_2) a few
more detailed scenarios.

🚧 Infographic:
Possible visualization of these exercise options.
A flowmap? “If this, then this” (with arrows).

### Summary of Dangers

Because of their importance, we’ll wind up with a recap of some of the key dangers we’ve
discussed when thinking about equity compensation:

- ❗ When it comes to equity compensation, details matter!
  You need to understand the type of stock grant or stock option in detail, as well as what
  it means for your taxes, to know what your equity is worth.
- ❗ Because details are so important, [professional advice](#seeking-professional-advice) from
  a tax advisor or lawyer familiar with equity compensation (or both) is often a good idea.
  Avoid doing everything yourself, but also avoid blindly trusting advisors without having
  them explain the details to you in a way you understand.
- ❗ With stock options, high exercise costs or high taxes, including the AMT trap, may
  prevent you from exercising your options.
  If you can’t sell the stock and your exercise window is limited, you could effectively be
  forced to walk away from your stock options.
- ❗ If a job offer includes equity, you need a lot of information to understand the value of
  the equity component.
  If the company trusts you enough to be making an offer but doesn’t want to answer
  questions about that offer, consider it a warning sign.
  Next, we offer more details on what to ask about your offer, and how to negotiate to get
  the answers you want.

## Offers and Negotiations

When a company offers any form of equity as part of its compensation package, there is a
whole new set of factors for a prospective employee to consider.
This chapter will help you prepare for negotiating a job offer that includes equity,
covering negotiation tips and expectations, and specific reminders on what you can ask and
what is negotiable when it comes to equity.

### Why Negotiation Matters

Before accepting any job offer, you’ll want to negotiate
[firmly and fairly](http://cefne.com/en/harvard-method-negotiation). You’re planning to devote
a lot of your time and sanity to any full-time role;
help yourself make sure that this is
[💰what you want](https://hbr.org/2016/12/think-strategically-about-your-career-development).

☝️ It’s perfectly natural to be
[anxious](https://www.pon.harvard.edu/daily/negotiation-skills-daily/the-impact-of-anxiety-and-emotions-on-negotiations-how-to-avoid-misjudgment-in-negotiation-scenarios/)
about negotiations, whether you’re going through this process for the first time or the
tenth. There is a lot at stake, and it can be uncomfortable and stressful to ask for
things you need or want.
Many
[people think](https://www.forbes.com/sites/tanyatarr/2017/12/31/here-are-five-negotiation-myths-we-can-leave-behind-in-2017/#250ff99b15f9engaging)
negotiating could get the job offer revoked, so they’ll accept their offer with little or
no discussion.
But remember that negotiations are the first experience you’ll have of working with your
new team. If you’re nervous, it can help to remind yourself why it’s important to have
these conversations:

- Negotiations ask you to focus on what you actually want.
  What is important to you—personal growth, career growth, impact, recognition, cash,
  ownership, teamwork?
  Not being clear with yourself on what your priorities really are is a recipe for
  dissatisfaction later.
- If you aren’t satisfied with the terms of your offer, accepting it without discussion can
  be tough not just for you but for your new company and colleagues as well.
  No one wants to take on a hire who’s going to walk away in just a few months when
  something better comes along.
  For everyone’s sake, take your time now to consider what you want—and then
  [ask for it](https://www.earnest.com/decision-making/articles/negotiating-job-offers-science-asking-want).
- The negotiation process itself can teach you a lot about a company and your future
  manager. Talking about a tough subject like an offer is a great way to see how you’ll work
  with someone down the road.

A Guide like this can’t give you personalized advice on what a reasonable offer is, as
that depends greatly on your skills, the marketplace of candidates, what other offers you
have, what the company can pay, what other candidates the company has found, and the
company’s needs.
But we can cover the basics of what to expect with offers, and advise candidates on how to
approach negotiations.

### Equal Treatment

🔹 Companies can and should work hard to ensure that all candidates are given
[equal treatment](https://rework.withgoogle.com/guides/pay-equity/steps/introduction/) in the
hiring process, but inequalities persist.[^iwprorgpub.1ukyxt]
Workplace disparities in pay and opportunity span race and gender,[^digitalcom.k5w0oc] with research
focusing on inequality in the U.S. workplace,[^pewresearc.dws8o8] executive leadership and its
well-documented lack of diversity,[^aflcioorgp.6v6p19][^fortunecom.87hw00] and the technology industry.[^eeocgoveeo.9aynwh]
Gender bias in negotiation itself is also an issue;
many women have been made to feel that they shouldn’t ask for what they deserve.[^newyorkerc.mdcz9c]

More effort is needed to end biases and close the wage gap.
All candidates should take the time to understand their worth and the specific value they
can add to a company, so that they are fully prepared to negotiate for a better offer.

### General Expectations

- Many companies will give some leeway during [negotiations](#negotiation-tips), letting you
  indicate whether you prefer
  [higher salary](https://hired.com/blog/candidates/salary-vs-equity-how-decide-whats-right/) or
  [higher equity](https://www.investopedia.com/articles/personal-finance/041515/equity-vs-salary-what-you-need-know.asp).
- Candidates with competing offers almost always have more leverage and get better offers.[^shrmorgres.qv3vrf]
- Salaries at startups are often a bit below what you’d get at an established company, since
  early on, cash is at a premium.
  For very early stage startups, risk is higher, offers can be more highly variable, and
  variation among companies will be greater, particularly when it comes to equity.
- The dominant factors [determining equity](#typical-employee-equity-levels) are what funding
  [stage](#stages-of-a-startup) a company is at, and the role you’ll play at the company.
  If no funding has been raised, large equity may be needed to get early team members to
  work for very little or for free.
  Once significant funding of an A round is in place, most people will take typical or
  moderately discounted salaries.
  Startups with seed funding lie somewhere in between.

### Offers

🄳 When making a job offer, companies will often give a candidate a **verbal offer** first,
to speed things along and facilitate the negotiation, following it with a **written offer**
if it seems like the candidate and the company are close to agreement on the terms of the
offer. The written offer takes the form of an
[📥**offer letter**](https://www.upcounsel.com/employee-offer-letter), which is just the summary
sent to the candidate, typically with an expiration date and other details and
[paperwork](#documents-and-agreements).

Although companies often want you to sign right away to save time and effort, if you’re
doing it thoughtfully you’ll also be talking to the company (typically with a hiring
manager, your future manager, or a recruiter, or some combination) multiple times before
signing. This helps you negotiate details and gives you a chance to get to know the people
you could be working with, the company, and the role, so that you can make the best
decision for your personal situation.

When you are ready to accept the terms of the offer letter, you can go ahead and sign.

Things to look for in the
[offer letter](https://www.glassdoor.com/blog/how-to-read-offer-letter/) include:

- **Title and level.**
  What your role is officially called, who you report to, and what level of seniority your
  role is within the company.
- **Salary.** What you’re paid in cash, in a year, before taxes.
- **Equity compensation.**
  You know what this is now.
- **Bonus.** Additional cash you’ll get on a regular basis, if the company has a plan for this.
- **[Signing bonus](https://www.investopedia.com/terms/s/signing-bonus.asp).** Cash you get just
  for signing. (Signing bonuses usually have some strings attached—for example, you could
  have to pay back the bonus if you leave the company within 12 or 24 months.)

While the details may not be included in your offer letter, to get full information on
your total rewards you’ll also want to discuss:

- [Benefits](https://en.wikipedia.org/wiki/Employee_benefits) like health insurance, retirement
  savings, and snacks.
- All other aspects of the job that might matter to you, like time off, ability to work from
  home, flexible hours, training and education, and so on.

A few general notes on these components (credits to
[Cristina Cordova](https://twitter.com/cjc/status/984094472190349312) for some of these):

- Early stage startups will focus on salary and equity and (if they are funded) benefits.
  An offer of bonuses or a signing bonus are more common in larger, prosperous companies.
- Bonuses are usually standardized to the company and your level, so are not likely to be
  something you can negotiate.
- The signing bonus is highly negotiable.
  This doesn’t mean any company will give large signing bonuses, but it’s feasible because
  signing bonus amounts vary candidate by candidate, and unlike salary and other bonuses,
  it’s a one-time cost to the company.

### Offers From Startups

Because startups are so much smaller than many established companies, and because they may
grow quickly, there are additional considerations worth taking into account when
negotiating a job offer from a startup:

- **Cash versus equity.**
  If your [risk tolerance](https://www.investopedia.com/terms/r/risktolerance.asp) is
  reasonably high, you might ask for an offer with more equity and less cash.
  If a company begins to do well, it’ll likely “level up” lower salaries (bringing them
  closer to market average) even if you got more equity up front.
  On the other hand, if you ask for more cash and less equity, it’s unlikely you’ll be able
  to negotiate to get more equity later on, since equity is increasingly scarce over time
  (at least in a successful company!). Entrepreneur and venture capitalist
  [Mark Suster](https://en.wikipedia.org/wiki/Mark_Suster) stresses the need to
  [level up](https://bothsidesofthetable.com/this-is-how-startups-level-up-after-raising-money-328d17076515)
  by scaling pay and spending, focusing appropriately at each funding stage.
  In the very early days of a startup, it’s not uncommon for employees to have higher
  salaries than the company’s founders.[^siliconhil.1wd4aa]
- 🚧 What is risk and how should people think about risk tolerance?
  Good readings on this?
- **Title.** Negotiating title and exact details of your role early on may not matter as much
  in a small and growing company, because your role and the roles of others may change a
  lot, and quickly.
  It’s more important that you respect the founders and leaders of the company.
  It’s more important that you feel you are
  [respected](https://blog.shrm.org/blog/respect-and-trust-top-the-list-of-most-important-employee-job-satisfaction).

### Questions Candidates Can Ask

🔹 It’s important to ask questions when you get an offer that includes any kind of equity.
In addition to helping you learn the facts about the equity offer, the process of
discussing these details can help you get a sense of the company’s transparency and
responsiveness.
Here are a few questions you should consider asking, especially if you’re evaluating an
offer from a startup or another private company:

- **Percentage ownership.**
  - *What percentage of the company do the shares represent?*
  - *What set of shares was used to compute that percentage?
    Is it outstanding shares or fully diluted?*
  - *What convertible securities are outstanding (convertible notes, SAFEs, or warrants), and
    how much dilution can I expect from their conversion?*
- **Valuation.**
  - *What did the last round value the company at?
    (That is, what is the preferred share price times the total outstanding shares?)*
  - *What is the most recent 409A valuation?
    When was it done, and will it be done again soon?*
  - *What exit valuation will need to be achieved before common stock has positive value (that
    is, what are the liquidation overhangs)?*
- **Stock options.**
  - *Do you allow early exercise of my options?*
  - *Am I required to exercise my options within 90 days after I leave or am terminated?
    Does the company extend the exercise window of the options of employees that depart?*
- **Vesting.**
  - *Are all employees on the same vesting schedule?*
  - *Is there any acceleration of my vesting if the company is acquired?*
  - *Do you have a policy regarding follow-on stock grants?*
  - *Does the company have any repurchase right to vested shares?*

This information will help you consider the benefits and drawbacks of possible
[exercise scenarios](#stock-option-scenarios).

🔹 If you’re considering working for a startup, there are further questions to ask in
order to assess the state of the company’s business and its plans.
Before or when you’re getting an offer is the right time to do this.
Startups are understandably careful about sharing financial information, so you may not
get full answers to all of these, but you should at least ask:

- *How much money has the company raised (including in how many rounds, and when)?*
- *What did the last round value the company at?*
- *What is the aggregate liquidation preference on top of the preferred stock?*
  (This will tell you how much the company needs to sell for before the common stock—your
  equity—is worth something in an exit.)
- *Will the company likely raise more capital soon?*
- *How long will the company’s current funding last?*
  (This will likely be given at the current burn rate, or how quickly a company is spending
  its funding, so will likely not include calculations for things like future employee
  salaries.)
- *What is the hiring plan?
  (How many people over what time frame?)*
- *What is the revenue now, if any?
  What are the revenue goals/projections?*
- *Where do you see this company in 1 year and 5 years, in terms of revenue, number of
  employees, and market position?*

There are several other
[resources](https://blog.wealthfront.com/stock-options-14-crucial-questions/) with
[more questions](http://www.inc.com/atish-davda/5-questions-you-should-ask-before-taking-a-start-up-job-offer.html)
like this to consider.

🚧 Summarize the best items in the links above.

### Typical Employee Equity Levels

🚧 This section currently mostly covers startups;
what later-stage resources are available?

Compensation data is highly situational.
What an employee receives in equity, cash, and benefits depends on the role they’re
filling, the sector they work in, where they and the company are located, and the possible
value that specific individual may bring to the company.

Any compensation data out there is hard to come by.
Companies often pay for this data from
[vendors](https://www.advanced-hr.com/products-overview), but it’s usually not available to
candidates.

For startups, a variety of data is easier to come by.
We give some overview here of early-stage Silicon Valley tech startups;
many of these numbers are not representative of companies of different kinds across the
country:

- 🔹 One of the best ways to tell what is reasonable for a given company and candidate is to
  look at offers from companies with similar profiles on [AngelList](https://angel.co/). The
  [**AngelList salary data**](https://angel.co/salaries) is extensive.
- There are no hard and fast rules, but for **post-series A startups** in **Silicon Valley**,
  the table below, based on
  [the one by Babak Nivi](http://venturehacks.com/articles/option-pool-shuffle#market), gives
  ballpark equity levels that many think are reasonable.
  These would usually be for restricted stock or stock options with a standard 4-year
  vesting schedule.
  They apply if each of these roles were filled just after an A round and the new hires are
  also being paid a salary (so are not founders or employees hired before the A round).
  The upper ranges would be for highly desired candidates with strong track records.
  - Chief executive officer (CEO): **5–10%**
  - Chief operating officer (COO): **2–5%**
  - Vice president (VP): **1–2%**
  - Independent board member: **1%**
  - Director: **0.4–1.25%**
  - Lead engineer **0.5–1%**
  - Senior engineer: **0.33–0.66%**
  - Manager or junior engineer: **0.2–0.33%**
- For **post-series B startups**, equity numbers would be much lower.
  How much lower will depend significantly on the size of the team and the company’s
  valuation.
- Seed-funded startups would offer higher equity—sometimes much higher if there is little
  funding, but base salaries will be lower.
- Leo Polovets created a
  [survey](http://codingvc.com/analyzing-angellist-job-postings-part-2-salary-and-equity-benchmarks)
  of AngelList job postings from 2014, an excellent summary of equity levels for the first
  few dozen hires at these early-stage startups.
  For **engineers** in Silicon Valley, the highest (not typical!)
  equity levels were:
  - Hire #1: up to **2%–3%**
  - Hires #2 through #5: up to **1%–2%**
  - Hires #6 and #7: up to **0.5%–1%**
  - Hires #8 through #14: up to **0.4%–0.8%**
  - Hires #15 through #19: up to **0.3%–0.7%**
  - Hires #21 [sic] through #27: up to **0.25%–0.6%**
  - Hires #28 through #34: up to **0.25%–0.5%**
- José Ancer gives another good
  [overview](http://siliconhillslawyer.com/2018/05/08/early-startup-employee-compensation/) for
  early stage hiring.
- *Founder* compensation is another topic entirely that may still be of interest to
  employees. José Ancer provides a thoughtful
  [overview](http://siliconhillslawyer.com/2016/06/23/founder-compensation-cash-equity-liquidity/).

### Negotiation Tips

🚧 Structure: Move negotiation points earlier?

When negotiating a job offer, companies will always ask you what you want for
compensation, and you should always be
[cautious](http://review.chicagobooth.edu/strategy/2018/article/how-answer-one-toughest-interview-questions)
about answering.

If you name the lowest number you’ll accept, you can be pretty sure the company’s not
going to exceed it, at least not by much.

🔸 Asking about salary expectations is a normal part of the hiring process at most
companies, but asking about **salary history** has been banned in a growing number of
states, cities, and counties.[^hrdivecomn.56fguz]
These laws attempt to combat pay disparity[^nytimescom.yev52k] among women and minorities by making it
illegal for companies to ask about or consider candidates’ current or past compensation
when making them offers.
Make sure you understand the laws relevant to your situation.

A few points on negotiating compensation:

- Some argue that a
  [good tactic](http://www.businessinsider.com/how-to-negotiate-make-first-offer-2014-5) in
  negotiating is to start higher than you will be willing to accept, so that the other party
  can “win” by negotiating you down a little bit.
  Keep in mind, this is just a suggested tactic, not a hard and fast rule.
- If you are inexperienced and unsure what a fair offer should look like, avoid saying
  exactly what you want for compensation very early in discussions.
  Though many hiring managers and recruiters ask about
  [salary expectations](http://fistfuloftalent.com/2018/01/ask-salary-without-asking-salary-expectations.html)
  early in the process to avoid risk at the offer stage, some ask in order to take
  advantage of candidates who don’t have a good sense of
  [their own worth](https://nuleadership.com/2018/01/08/know-your-worth-compensation-negotiation/).
  Tell them you want to focus on the opportunity as a whole and your ability to contribute
  before discussing numbers.
  Ask them to give you a fair offer once they understand what you can bring to the company.
- If you are experienced and know your value, it’s often in your interest to state what sort
  of compensation and role you are looking for to anchor expectations.
  You might even share your expectations early in the process, so you don’t waste each
  other’s time.
- Discuss what your compensation might be like in the future.
  No one can promise you future equity, salary, or bonuses, but it should be possible to
  agree what those could look like *if* you demonstrate outstanding performance and the
  company has money.
- If you’re moving from an established company to a startup, you may be asked to take a
  [salary cut](https://www.quora.com/Should-you-take-a-salary-cut-if-you-join-a-startup). This
  is reasonable, but it’s wise to discuss explicitly how much the cut is, and when your
  salary will be renegotiated.
  For example, you might take 25% below your previous salary, but there can be an agreement
  that this will be corrected if your performance is strong and the company gets funding.
- 🔹 Always negotiate
  [non-compensation](http://www.kennedyexecutive.com/blog/salary-negotiation-33-things-negotiate-money/)
  aspects before agreeing to an offer.
  If you want a specific role, title, opportunity, visa sponsorship, parental leave, special
  treatment (like working from home), or have timing constraints about when you can join,
  [negotiate these early](https://www.nerdwallet.com/blog/loans/student-loans/negotiate-nonsalary-benefits-job-perks/),
  not late in the process.
- 🔹 If you’re going to be a very early employee, consider asking for a restricted stock
  grant instead of stock options, and a cash bonus equal to the tax on those options.
  The company will have some extra paperwork (and legal costs), but it means you won’t have
  to pay to exercise.
  Then, if you file an 83(b) election, you’re simplifying your situation even further,
  eliminating the [AMT issues](#the-amt-trap) of ISOs, and maximizing your chances of
  qualifying for long-term capital gains tax.
- 🚧 What other *specific* suggestions are helpful?

A few notes on the negotiation process itself:

- 🔹 Although offer letters have expirations, it’s often possible to negotiate more time if
  you need it. How much flexibility depends on the situation.
  Some have criticized “exploding job offers” as a
  [bad practice](https://www.huffingtonpost.com/adam-grant/its-time-to-eliminate-exp_b_4594222.html)
  that makes [no sense](https://erikbern.com/2016/03/16/exploding-offers-are-bullshit.html) at
  all. If you are likely the best candidate for the position, or the role is a specialized
  and well-paid one where there are usually not enough good candidates to meet the demand,
  you’ll likely have plenty of leverage to
  [ask for more time](http://www.businessinsider.com/how-to-politely-postpone-accepting-a-job-offer-2015-6#dont-be-afraid-to-negotiate-4),
  which may be needed to complete the interview process with other companies.
  Software engineering roles in tech companies are like this currently.
- Getting
  [multiple offers](https://www.themuse.com/advice/a-guide-to-juggling-multiple-job-offers-and-coming-out-on-top)
  is always in your interest.
  If you have competing offers, sharing the competing offers with the company you want to
  work for can be helpful, granted your offers are competitive.
  - However, dragging out negotiations excessively so you can “shop around” an offer to other
    companies is considered bad form by some;
    it’s thoughtful to be judicious and timely to the extent that it’s possible.
- ❗ Get all agreements in writing, if they are not in your offer letter.
- Do not accept an offer verbally or in writing unless you’re ready to stand by your word.
  In practice, people do occasionally accept an offer and then go back on it, or
  [*renege*](https://purduecco.wordpress.com/2016/03/28/the-risks-of-reneging-on-a-job-offer/).
  This can put the company in a difficult position (they may have declined another key
  candidate based on your acceptance), and may hurt your reputation in unexpected ways
  later.

Some additional resources:

- Harvard Business Review has a variety of general
  [💰suggestions](https://hbr.org/2014/04/15-rules-for-negotiating-a-job-offer) on negotiation
  processes.
- Robby Grossman, a VP at Wistia, gives a good
  [overview](http://rob.by/2013/negotiating-your-startup-job-offer) of equity compensation and
  negotiation suggestions in startups.

### Offer and Negotiation Dangers

To wind up our discussion of offers and negotiations, here are some key dangers and
mistakes to watch out for:

- ❗ Do not accept an offer of stock or shares without also asking for the exact number of
  total shares (or, equivalently, the exact percentage of the company those shares
  represent). It’s quite common for some companies to give offers of stock or options and
  tell you only the number of shares.
  Without the percentage, the number of shares is meaningless.
  Not telling you is a deeply unfair practice.
  A company that refuses to tell you even when you’re ready to sign an offer is likely
  giving you a very poor deal.
- 🔸 If you’re looking at an offer, work out whether you can and should early exercise, and
  what the cost to exercise and tax will be, before accepting the offer.
- ❗ If you join a startup right as it raises a new round, and don’t have the chance to
  exercise right away, they may potentially issue you the options with the low strike price,
  but the 409A valuation of the stock will have gone up.
  This means you won’t be able to early exercise without a large tax bill.
  In fact, it might not be financially feasible for you to exercise at all.
- ❗ Vesting starts on a vesting commencement date.
  Sometimes stock option paperwork won’t reach you for weeks or months after you join a
  company, since it needs to be written by the lawyers and approved by the board of
  directors. In your negotiations, do make sure the vesting commencement date will reflect
  the true start date of when you joined the company, not the time at which the stock option
  is granted.
- 🔸 The offer letter is not the actual grant of your equity.
  After you sign your offer letter, ensure the company delivers you your actual equity grant
  documents within a few weeks.
  It is not uncommon for early-stage startups to be sloppy with their equity granting.
  If they take too long to send your grant documents, the fair market value (and exercise
  price) of the equity could rise in the time you’re waiting, which is money lost for you.
- 🔸 If you’re going to early exercise, consider it like any investment.
  Don’t believe every projection about the value of the company you hear.
  Founders will tell you the best-case scenario.
  Remember, most startups fail.
  Do your research and ask others’ opinions about likely outcomes for the company.
- ❗ It may not be common, but some companies retain a right to repurchase (buy back) vested
  shares. It’s simple enough to ask, “Does the company have any repurchase right to *vested*
  shares?” (Note repurchasing *unvested* shares that were purchased via early exercise is
  different, and helps you.)
  If you don’t want to ask, the fair market value repurchase right should be included in the
  documents you are being asked to sign or acknowledge that you have read and understood.
  (Skype’s
  [controversy](https://techcrunch.com/2011/06/26/skypes-worthless-employee-stock-option-plan-heres-why-they-did-it/)
  related to repurchasing has some startup employees
  [looking out](https://www.quora.com/Which-valley-startups-have-a-Skype-like-repurchase-right)
  for companies with similar plans.)
  You might find a repurchase right for vested shares in the Stock Plan itself, the Stock
  Option Agreement, the Exercise Agreement, the bylaws, the certificate of incorporation, or
  any other stockholder agreement.

## Documents and Agreements

This section covers a few kinds of documents you’re likely to see as you negotiate a job
offer and sign on to a company.
It’s not exhaustive, as titles and details vary.

- When you are considering your offer, make sure you have all of the documents you need from
  the company:
  - Your [📥offer letter](https://www.upcounsel.com/employee-offer-letter), which will detail
    salary, benefits, and equity compensation.
  - An
    [📥Employee Innovations Agreement](https://recruit.smashfly.com/SmashFlyMedia/Docs/12250/12250_168_United%20States%20-%20EIPIA%20English%20%28Rev%2014%20FEBRUARY%202017%29%202%20pages.pdf),
    Proprietary Information and Inventions Assignment Agreement, or similar, concerning
    intellectual property.
- If you have equity compensation, at some point—possibly weeks or months after you’ve
  joined—you should get a Summary of Stock Grant, Notice of Stock Option Grant, or similar
  document, detailing your grant of stock or options, along with all details such as number
  of shares, type of options, grant date, vesting commencement date, and vesting schedule.
  It will come with several other documents, which may be exhibits to that agreement:
  - [📥Stock Option Agreement](https://www.upcounsel.com/stock-option-agreement)
  - [📥Stock Plan](https://www.upcounsel.com/equity-incentive-plan) (sometimes called a Stock
    Option Plan, or Stock Award Plan, or Equity Incentive Plan)
  - [📥Code Section 409A Waiver and Release](https://www.lawinsider.com/clause/code-section-409a-waiver-and-release)
    (sometimes part of the Stock Option Agreement)
- If you are exercising your options, you should also see paperwork to assist with that
  purchase:
  - [📥Exercise Agreement](https://www.upcounsel.com/option-exercise-agreement)
  - Instructions and template for early exercise and
    [📥83(b) election](https://www.irs.gov/pub/irs-drop/rp-12-29.pdf), if applicable
- End of year tax documents

- You should receive a form
    [📥3921 or 3922](https://www.irs.gov/uac/form-3921-exercise-of-an-incentive-stock-option-under-section-422-b)
    from your company if you exercised ISO options during the year.

## Further Reading

The resources here are a small subset of the full set of resources cited in the Guide to
Equity Compensation, selected for their breadth, notability, or depth on specific issues.

### General Resources

- Mark P. Cussen, Investopedia,
  [*Introduction To Incentive Stock Options*](http://www.investopedia.com/articles/stocks/12/introduction-incentive-stock-options.asp),
  updated 2017.
- Alex MacCaw,
  [*An Engineer’s Guide to Stock Options*](http://blog.alexmaccaw.com/an-engineers-guide-to-stock-options),
  2013.
- Andy Rachleff, Wealthfront,
  [*The 14 Crucial Questions about Stock Options*](https://blog.wealthfront.com/stock-options-14-crucial-questions),
  2014.
- Mary Russell, Stock Option Counsel,
  [*Startup Equity Standards: A Guide for Employees*](http://www.slideshare.net/StockOptionCnsl/startup-standards-stock-option-counsel),
  2014.
- David Weekly,
  [ 💰*An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee*](https://www.scribd.com/doc/55945011/An-Introduction-to-Stock-Options-for-the-Tech-Entrepreneur-or-Startup-Employee#scribd),
  2012.
- Investopedia,
  [*Employee Stock Options: Definitions and Key Concepts*](http://www.investopedia.com/university/employee-stock-options-eso/eso1.asp).

### Considerations for Founders

- Matthew Bartus, Cooley GO,
  [*Option Grants: Fully Diluted or Issued and Outstanding*](https://www.cooleygo.com/option-grants-fully-diluted-issued-outstanding/).
- Jay Bhatti, Business Insider,
  [*How Startups Should Deal With Cliff Vesting For Employees*](http://www.businessinsider.com/everything-you-need-to-know-about-cliff-vesting-2011-5),
  2011.
- Tahir J. Naim, Fenwick,
  [*Section 409A Valuations and Stock Option Grants for Start-up Technology and Life Science Companies*](http://www.fenwick.com/FenwickDocuments/409_Valuations_Stock_Options.pdf).
- Babak Nivi, Venture Hacks
  [*The Option Pool Shuffle*](http://venturehacks.com/articles/option-pool-shuffle) (and
  [table of equity](http://venturehacks.com/articles/option-pool-shuffle#market) ranges), 2017.
- Leo Polovets,
  [*Analyzing AngelList Job Postings, Part 2: Salary and Equity Benchmarks*](http://codingvc.com/analyzing-angellist-job-postings-part-2-salary-and-equity-benchmarks),
  2014.
- Beth Scheer, Homebrew, [Compensation at Startups](https://quip.com/HEB3Ah9dYD6o).
- Scott Edward Walker, VentureBeat,
  [*Beware the trappings of liquidation preference*](http://venturebeat.com/2010/08/16/beware-the-trappings-of-liquidation-preference/),
  2010.
- Joe Wallin, The Startup Law Blog,[*Top 6 Reasons To Grant NQOs Over ISOs*](http://www.startuplawblog.com/2010/08/11/top-reasons-nqos-over-isos/),
  2010.
- Clerky, [*Legal Concepts for Founders*](https://handbook.clerky.com/).

### Considerations for Candidates and Employees

- Anonymous,
  [*What I Wish I’d Known About Equity Before Joining A Unicorn*](https://gist.github.com/yossorion/4965df74fd6da6cdc280ec57e83a202d),
  2017.
- Atish Davda, Inc,
  [*5 Questions You Should Ask Before Accepting a Startup Job Offer*](http://www.inc.com/atish-davda/5-questions-you-should-ask-before-taking-a-start-up-job-offer.html),
  2014.
- Julia Evans,
  [*Things you should know about stock options before negotiating an offer*](http://jvns.ca/blog/2015/12/30/do-the-math-on-your-stock-options/),
  2015.
- Guy Kawasaki, [*Nine Questions to Ask a Startup*](http://guykawasaki.com/nine_questions_/),
  2006.
- Sheelah Kolhatkar, The New Yorker,
  [*The Tech Industry’s Gender-Discrimination Problem*](https://www.newyorker.com/magazine/2017/11/20/the-tech-industrys-gender-discrimination-problem),
  2017.
- Eileen Patten, Pew Research Center,
  [*Racial, gender wage gaps persist in U.S. despite some progress*](http://www.pewresearch.org/fact-tank/2016/07/01/racial-gender-wage-gaps-persist-in-u-s-despite-some-progress/),
  2016.
- Leo Polovets, [*Valuing Employee Options*](http://codingvc.com/valuing-employee-options/),
  2015\.
- Andy Rachleff, Wealthfront,
  [*When Should You Exercise Your Stock Options?*](https://blog.wealthfront.com/when-to-exercise-stock-options/),
  2015.
- David Weekly, GigaOm,
  [*5 Mistakes You Can’t Afford to Make with Stock Options*](https://gigaom.com/2011/06/05/5-mistakes-you-cant-afford-to-make-with-stock-options/),
  2011.

### Types of Equity Compensation

- Jeron Paul, Capshare,
  [*RSUs vs. Options: Why RSUs (Restricted Stock Units) Could be Better Than Stock Options At Your Private Company*](https://www.capshare.com/blog/rsus-vs-options/),
  2016.
- Andy Rachleff, Wealthfront,
  [*How Do Stock Options and RSUs Differ?*](https://blog.wealthfront.com/stock-options-versus-rsu/),
  2014.
- Mary Russell, Stock Option Counsel,
  [*Early Expiration of Startup Stock Options - Part 3 - Examples of Good Equity Design by Company Stage*](http://stockoptioncounsel.com/blog/early-expiration-of-startup-stock-options-part-3-examples-of-good-startup-equity-design-by-company-stage/2017/8/11),
  2017.
- Joe Wallin, The Startup Law Blog,
  [*Incentive Stock Options vs. Nonqualified Stock Options*](http://www.startuplawblog.com/2013/05/15/incentive-stock-options-vs-nonqualified-stock-options/),
  2013.
- Joe Wallin,
  [*RSUs vs. Restricted Stock vs. Stock Options*](http://joewallin.com/2014/09/13/rsus-vs-restricted-stock-vs-stock-options/),
  2014.

### Taxes

- Steven Ayre, Accelerated Vesting,
  [*What Is An 83(b) Election and When Do I Make It?*](http://acceleratedvesting.com/what-is-an-83b-election-and-when-do-i-make-it-part-1-with-graphic/),
  2013.
- Mark P. Cussen, Investopedia,
  [*How Restricted Stock And RSUs Are Taxed*](http://www.investopedia.com/articles/tax/09/restricted-stock-tax.asp?performancelayout=true).
- Barry Kramer,
  [🔑*The Tax Law that is (Unintentionally) Hammering Silicon Valley Employees*](https://medium.com/@barryjk/the-tax-law-that-is-unintentionally-hammering-silicon-valley-employees-894a7b54ba8a),
  2015.
- Joshua Levy and Joe Wallin, The Startup Law Blog,
  [*The Problem With Immediately Exercisable ISOs*](http://thestartuplawblog.com/the-problem-with-immediately-exercisable-isos/),
  2015.
- Kaye A. Thomas, Fairmark,
  [*AMT and Long-Term Capital Gain*](http://fairmark.com/general-taxation/alternative-minimum-tax/amt-long-term-capital-gain/),
  2014.
- Robert W. Wood, Forbes,
  [*Ten Tax Tips For Stock Options*](http://www.forbes.com/2010/03/10/10-tax-tips-stock-options-personal-finance-robert-wood.html),
  2010.
- NCEO,
  [*Stock Options and the Alternative Minimum Tax (AMT)*](https://www.nceo.org/articles/stock-options-alternative-minimum-tax-amt)

### Vesting and Expiration of Stock Options

- Babak Nivi, Venture Hacks,
  [*How to make a cap table*](http://venturehacks.com/articles/cap-table), 2007.
- Mary Russell, Stock Option Counsel,
  [*Can the Company Take Back My Vested Shares?*](http://stockoptioncounsel.com/blog/standards-ownership-canthecomanytakebackmyvestedshares),
  2017.
- Mary Russell, Stock Option Counsel,
  [*Early Expiration of Startup Stock Options - Part 1 - A $1 Million Problem*](http://stockoptioncounsel.com/blog/nc7go8ivzxb1el5rhv6nltrjan0n2t/2017/3/6),
  2017.
- Mary Russell, Stock Option Counsel,
  [*Early Expiration of Startup Stock Options - Part 2 -The Full 10-Year Term Solution*](http://stockoptioncounsel.com/blog/early-expiration-of-startup-stock-options-part-2-the-full-10-year-term-solution/2017/3/28),
  2017.
- Dan Shapiro, [*Vesting is a hack*](http://www.danshapiro.com/blog/2012/04/vesting-is-a-hack/),
  2012.

### Negotiation

- Robby Grossman,
  [*Negotiating Your Startup Job Offer*](http://rob.by/2013/negotiating-your-startup-job-offer),
  2013.
- Sheelah Kolhatkar, The New Yorker,
  [*Lean Out: The Dangers for Women who Negotiate*](https://www.newyorker.com/magazine/2017/11/20/the-tech-industrys-gender-discrimination-problem),
  2017.
- Deepak Malhotra, Harvard Business Review,
  [15 Rules for Negotiating a Job Offer](https://hbr.org/2014/04/15-rules-for-negotiating-a-job-offer),
  2014.
- [CEFNE (Center for Study and Training in Business Negotiation)](http://cefne.com/en/harvard-method-negotiation)

### Forms and Tools

- [🔨TLDR Stock Options](https://tldroptions.io/) and [OwnYourVenture](http://ownyourventure.com/)
  are simulators illustrating equity calculations and dilution
- Orrick,
  [📥Startup Forms: Equity Compensation](https://www.orrick.com/Total-Access/Tool-Kit/Start-Up-Forms/Equity-Compensation)

## Disclaimer

*This Guide and all associated comments and discussion do not constitute legal or tax
advice in any respect.
No reader should act or refrain from acting on the basis of any information presented
herein without seeking the advice of counsel in the relevant jurisdiction.
The author(s) expressly disclaim all liability in respect of any actions taken or not
taken based on any contents of this Guide or associated content.*

## Credits

Many thanks to all
[contributors](https://github.com/jlevy/og-equity-compensation/graphs/contributors) to this
Guide and those who have given detailed feedback, including
[Julia Evans](https://twitter.com/b0rk), [George Grellas](https://twitter.com/grellas),
[Chris McCann](https://twitter.com/mccannatron), [Leo Polovets](https://twitter.com/lpolovets),
[Srinath Sridhar](https://www.linkedin.com/in/srinath-sridhar-0a16705),
[Andy Sparks](https://twitter.com/SparksZilla), and [David Weekly](https://twitter.com/dweekly),
and to the many [commentators on Hacker News](https://news.ycombinator.com/item?id=10880726).
The original authors are [Joshua Levy](https://twitter.com/ojoshe) and
[Joe Wallin](https://twitter.com/joewallin).

### Please Help!

This Guide is a living publication, imperfect but improving.
If you have an idea or contribution that might improve this Guide, please add suggestions
in the margins.
We gladly credit all contributors.

## License

[![Creative Commons License](https://i.creativecommons.org/l/by-sa/4.0/88x31.png)](http://creativecommons.org/licenses/by-sa/4.0/)

This work is licensed under a
[Creative Commons Attribution-ShareAlike 4.0 International License](http://creativecommons.org/licenses/by-sa/4.0/).

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