Option Pool Posts

Summary: A cap table lists who owns what in a startup. It calculates how the option pool shuffle and seed debt lower the Series A share price. This post includes a fill-in-the-blank spreadsheet you can purchase to create your own cap table.

A capitalization (cap) table lists who owns what in a startup. It lists the company’s shareholders and their shares.

This screencast walks you through our cap table:

The cap table is free

We used to charge for this stuff but now it’s free.

“This is great; we (probably like many other entrepreneurs) tried our hand at hacking up a similar spreadsheet on our own but this is a far more flexible and easy way of visualizing various scenarios. Thanks for putting this together.”

– Drew Houston, Founder of Dropbox

The cap table shows you what you really own

Many entrepreneurs think their pre-money valuation determines their percentage ownership of the company. They forget about the option pool shuffle. They forget about seed debt and its discount. Then they blame their lawyers.

Use this cap table to sketch out how much you will really own after the financing. Find something else to blame on your lawyers.

This cap table is simplified

Our cap table includes the major economic levers of a Series A: common stock, preferred stock, options, and convertible debt. It doesn’t include warrants, vesting, debt interest, liquidation preferences, dividends, the Series B, et cetera.

Cap tables can be a little tricky to understand if you’ve never worked with one before. So we kept it simple.

Your lawyer or accountant will deal with the details that aren’t included in this cap table. They will maintain the company’s official cap table.

Disclaimer — read this

Use this spreadsheet to learn more about cap tables and what your cap table might look like. Then hire a lawyer to maintain the company’s official cap table.

This cap table is provided as-is, with no warranties. It is not legal advice. We make no representations that this cap table is accurate in any way or is fit for any purpose.

We do not take responsibility for anything that results from using this cap table, including, but not limited to, losing all your money and going to jail.

We are not lawyers. Get a lawyer.

Do you have any suggestions or questions?

Please leave your suggestions and questions in the comments and we’ll improve the cap table.

We love the quality of the comments on Venture Hacks. You’re missing out if you’re not reading them.

A lot of the comments contain great anecdotes from founders. Others contain good questions which we make sure to answer.

Here’s a few recent ones that are especially good. You can also subscribe to our comments RSS feed.

Legal Fees

Joe Greenstein (from Flixster) says:

“I just want to throw in that my personal pet peeve with regard to the “standard” term sheet is the bit about the company paying the VC legal costs. C’mon – you have $500M and I am raising $1.5M and you want me to take the first $25k to pay your legal expenses for doing the deal? That’s like your dad giving you your allowance and then asking you to buy him a hot dog.

When we were raising money for flixster i thought that must be a trick — like if i agreed to that term they would pull the term sheet at the last second and say i failed the secret fiscal responsibility test…”

Option Pools

Andrew Parker (an Analyst at Union Square Ventures) says:

“In a negotiation, you can also try to change the rules of the game (change the formulas). For example, I know a few CEOs that have successfully negotiated that any option pool be created after the investment by institutional money, not before. So, the investors took the pool dilution along with the founders. This represents a significant increase in valuation without asking for an increase in valuation. It’s a hard chip to win in bargaining, but it’s worth taking a shot considering the high reward.”


“Anonymous” says:

“Some part of the term-sheets is like negotiating “pre nups”. You are basically negotiating the framework to follow when things go wrong or you end up in disagreement in future, just at the point where you are agreeing to work together in present.

One thing the article should expand upon is how to negotiate without scaring of the VCs. An entrepreneur has to balance protecting his interest with not coming across as someone that might be a “problem founder”. No VCs like to work with someone they perceive as a problematic founders. It is a tight rope walk!”


Suzie Dingwall Williams (a lawyer) says :

“Whatever you do, make sure that the [double] trigger runs for a period of time BEFORE as well as AFTER change of control. You want to avoid any pre-emptive house cleaning of management before the deal is done.

I still get a good deal of moral outrage from investors when I try to negotiate this provision into the deal. Their objections seem to be a knee jerk reaction to anything that might cut into their ROI on a liquidty event. As if.”

“Entrepreneur” says:

“I would like to add it is possible to raise VC money without founder vesting provisions. I recently closed a series A round for a six month old company with no founder vesting provisions. We took them out of the term sheet and they weren’t discussed again. We’ve worked previously with the same VC with great outcomes so we had a strong hand.”

“A Founder” says :

“I went to these VCs with a new CEO candidate whom I had worked with for 12 months previously. The investment proceeded and I stepped aside. Four months later I was asked if I wanted to leave and sell my shares. The offer was way below the value of the previous round so I said I would leave, but retain the shares and a board seat. However, they really wanted me gone. The deal was I would be terminated without cause, but loss of employment meant loss of board seat, which meant no ability to protect my shareholding (about 20% at that point). I was actually told by the CEO (a buddy?) that they would engineer a down round just to force me out.

Eventually we reached a compromise, but the lessons learned were:

1. Resist vesting if you have devoted time and your own capital to a business prior to VC investment.

2 Have a board seat linked to the shareholding, not the employment contract.”

You can now subscribe to our comments RSS feed.

Summary: Focus on your share price and the number of shares you own — metrics like valuation and percent ownership can fool you.

If valuation is your only pespective on a company’s capital structure, you can get fooled by games like the option pool shuffle which make your valuation seem large but actually depress your share price.

Focus on share value, not share quantity or valuation.

The most naive shareholders focus on the quantity of shares they own. That’s a mistake. The company can double your share quantity with a simple stock split. Do you feel rich now? We know companies that have 200M shares outstanding after the Series A just to fool their employees!

Merely uneducated shareholders focus on the percentage of the company they own. News flash: owning 99% of a company that is worth $10 is not going to make you rich.

Experienced shareholders (and Venture Hacks readers) focus on the current value of their shares and the company’s prospects. Investors in public companies with wacky capital structures don’t fancy that they own 0.0003% of a company that is worth $1B. Instead, they multiply today’s share price by the quantity of their shares to determine their share value. They track percentage ownership and valuation, but they focus on share price.

You should do the same:

Understand how any proposed change to the company’s capital structure affects the share price.

Employees should track share price too.

The number of options that new hires receive drops quickly as the value of the company increases and risk decreases. But the value of these options declines much more slowly because the increase in share price partially compensates for the reduction in share quantity.

On the other hand, if the share price is going down, the CEO and other “key” members of the management team often receive more shares to boost their share value — particularly after a new financing with inside investors.

The employees and founders who are left out of this little party should crash it.

Appendix: How to derive the share price.

These terms are negotiated in a simple Series A:

p = pre-money ($)
c = cash invested ($)
o = option pool size post-money (%)

and we hope you already know this:

x = existing shares outstanding (shares).

With these known values, it is easy to calculate all the unknowns:

value symbol equation
post-money ($) t t = p + c
new options (shares) n n = (x · o · t) ÷ (p − o · t)
share price ($/share) s s = p ÷ (x + n)
investor shares (shares) i i = c ÷ s
effective valuation ($) e e = s · x

“Follow the money card!”

– The Inside Man, Three-Card Shuffle

Summary: Don’t let your investors determine the size of the option pool for you. Use a hiring plan to justify a small option pool, increase your share price, and increase your effective valuation.

If you don’t keep your eyes on the option pool while you’re negotiating valuation, your investors will have you playing (and losing) a game that we like to call:

Option Pool Shuffle

You have successfully negotiated a $2M investment on a $8M pre-money valuation by pitting the famous Blue Shirt Capital against Herd Mentality Management. Triumphant, you return to your company’s tastefully decorated loft or bombed-out garage to tell the team that their hard work has created $8M of value.

Your teammates ask what their shares are worth. You explain that the company currently has 6M shares outstanding so the investors must be valuing the company’s stock at $1.33/share:

$8M pre-money ÷ 6M existing shares = $1.33/share.

Later that evening you review the term sheet from Blue Shirt. It states that the share price is $1.00… this must be a mistake! Reading on, the term sheet states, “The $8 million pre-money valuation includes an option pool equal to 20% of the post-financing fully diluted capitalization.”

You call your lawyer: “What the fuck?!”

As your lawyer explains that the so-called pre-money valuation always includes a large unallocated option pool for new employees, your stomach sinks. You feel duped and are left wondering, “How am I going to explain this to the team?”

If you don’t keep your eyes on the option pool, your investors will slip it in the pre-money and cost you millions of dollars of effective valuation. Don’t lose this game.

The option pool lowers your effective valuation.

Your investors offered you a $8M pre-money valuation. What they really meant was,

“We think your company is worth $6M. But let’s create $2M worth of new options, add that to the value of your company, and call their sum your $8M ‘pre-money valuation’.”

For all of you MIT and IIT students out there:

$6M effective valuation + $2M new options + $2M cash = $10M post


60% effective valuation + 20% new options + 20% cash = 100% total.

Slipping the option pool in the pre-money lowers your effective valuation to $6M. The actual value of the company you have built is $6M, not $8M. Likewise, the new options lower your company’s share price from $1.33/share to $1.00/share:

$8M pre ÷ (6M existing shares + 2M new options) = $1/share.

Update: Check out our $9 cap table which calculates the effect of the option pool shuffle on your effective valuation.

The shuffle puts pre-money into your investor’s pocket.

Proper respect must go out to the brainiac who invented the option pool shuffle. Putting the option pool in the pre-money benefits the investors in three different ways!

First, the option pool only dilutes the common stockholders. If it came out of the post-money, the option pool would dilute the common and preferred shareholders proportionally.

Second, the option pool eats into the pre-money more than it would seem. It seems smaller than it is because it is expressed as a percentage of the post-money even though it is allocated from the pre-money. In our example, the new option pool is 20% of the post-money but 25% of the pre-money:

$2M new options ÷ $8M pre-money= 25%.

Third, if you sell the company before the Series B, all un-issued and un-vested options will be cancelled. This reverse dilution benefits all classes of stock proportionally even though the common stock holders paid for all of the initial dilution in the first place! In other words, when you exit, some of your pre-money valuation goes into the investor’s pocket.

More likely, you will raise a Series B before you sell the company. In that case, you and the Series A investors will have to play option pool shuffle against the Series B investors. However, all the unused options that you paid for in the Series A will go into the Series B option pool. This allows your existing investors to avoid playing the game and, once again, avoid dilution at your expense.

Solution: Use a hiring plan to size the option pool.

You can beat the game by creating the smallest option pool possible. First, ask your investors why they think the option pool should be 20% of the post-money. Reasonable responses include

  1. “That should cover us for the next 12-18 months.”
  2. “That should cover us until the next financing.”
  3. “It’s standard,” is not a reasonable answer. (We’ll cover your response in a future hack.)

Next, make a hiring plan for the next 12 months. Add up the options you need to give to the new hires. Almost certainly, the total will be much less than 20% of the post-money. Now present the plan to your investors:

“We only need a 10% option pool to cover us for the next 12 months. By your reasoning we only need to create a 10% option pool.”

Reducing the option pool from 20% to 10% increases the company’s effective valuation from $6M to $7M:

$7M effective valuation + $1M new options + $2M cash = $10M post


70% effective valuation + 10% new options + 20% cash = 100% total

A few hours of work creating a hiring plan increases your share price by 17% to $1.17:

$7M effective valuation ÷ 6M existing shares = $1.17/share.

How do you create an option pool from a hiring plan? #

To allocate the option pool from the hiring plan, use these current ranges for option grants in Silicon Valley:

Title Range (%)
CEO 5 – 10
COO 2 – 5
VP 1 – 2
Independent Board Member 1
Director 0.4 – 1.25
Lead Engineer 0.5 – 1
5+ years experience Engineer 0.33 – 0.66
Manager or Junior Engineer 0.2 – 0.33

These are rough ranges – not bell curves – for new hires once a company has raised its Series A. Option grants go down as the company gets closer to its Series B, starts making money, and otherwise reduces risk.

The top end of these ranges are for proven elite contributors. Most option grants are near the bottom of the ranges. Many factors affect option allocations including the quality of the existing team, the size of the opportunity, and the experience of the new hire.

If your company already has a CEO in place, you should be able to reduce the option pool to about 10% of the post-money. If the company needs to hire a new CEO soon, you should be able to reduce the option pool to about 15% of the post-money.

Bring up your hiring plan before you discuss valuation.

Discuss your hiring plan with your prospective investors before you discuss valuation and the option pool. They may offer the truism that “you can’t hire good people as fast as you think.” You should respond, “Okay, let’s slow down the hiring plan… (and shrink the option pool).”

You have to play option pool shuffle.

The only way to win at option pool shuffle is to not play at all. Put the option pool in the post-money instead of the pre-money. This benefits you and your investors because it aligns your interests with respect to the hiring plan and the size of the option pool.

Still, don’t try to put the option pool in the post-money. We’ve tried – it doesn’t work.

Your investor’s norm is that the option pool goes in the pre-money. When your opponent has different norms than you do, you either have to attack his norms or ask for an exception based on the facts of your case. Both straits are difficult to navigate.

Instead, skillful negotiators use their opponent’s standards and norms to advance their own arguments. Fancy negotiators call this normative leverage. You apply normative leverage in the option pool shuffle by using a hiring plan to justify a small option pool.

You can’t avoid playing option pool shuffle. But you can track the pre-money as it gets shuffled into the option pool and back into the investor’s pocket, you can prepare a hiring plan before the game starts, and you can keep your eye on the money card.