CEO Posts

Our previous vesting hacks have discussed getting vested for time served, acceleration upon termination, and acceleration upon a sale. This article is a collection of four vesting microhacks you can use to supersize your vesting.

1. Reclaim a terminated co-founder’s unvested shares.

A terminated co-founder’s unvested shares are typically cancelled. The resulting reverse dilution benefits the founders, employees, and investors ratably.

Instead of canceling the shares, divide them among the remaining co-founders and employees ratably. You should argue that,

“Cancelling a terminated co-founders shares puts a lot of pre-money into the investor’s pocket. Those shares should be distributed among the founders and employees who created that pre-money valuation.”

This argument will carry more water if you offer to put a portion of the reclaimed shares into the option pool to hire a replacement for the co-founder.

Reclaiming a terminated co-founder’s shares does not create an incentive for co-founders to terminate each other. Co-founders have an incentive to terminate each other even if the shares are cancelled. In our experience, this incentive is never a factor. Founders are almost always allowed to vest in peace unless they are incompetent, actively harmful, or clash with a new CEO.

2. Run screaming from the right to purchase vested stock.

Some option plans provide the company the right to repurchase your vested stock upon your departure. The purchase price is ‘fair market value’. Guess whether the definition of fair market value is favorable to you or the company…


Founders and employees should not agree to this provision under any circumstances. Read your option plan carefully.

(Props to Suzie Dingwall Williams who already brought up this microhack in the comments.)

3. Accelerate your vesting upon hiring a new CEO.

If you are having trouble applying any of the other vesting hacks, trade those chips in for six months of acceleration upon hiring a new CEO. Investors are usually eager to bring in “professional” management. They should agree to this term because it aligns your interests with theirs.

4. Keep vesting as a consultant or board member.

If you have a lot of leverage, you may be able to negotiate an agreement to keep vesting if you are terminated but retained as a consultant or a board member. For example, the company may terminate you but keep you as a consultant to help decipher your spaghetti code.

Some companies have been known to sneak this term into their closing documents. We’re not big fans of that approach.

Again, if you are having trouble applying any of the other vesting hacks, you may be able to trade those chips in for this one.

What are your vesting micro-hacks?

Submit your vesting micro-hack experiences and questions in the comments. We’ll discuss the most interesting ones in a future article.

“During the whole funding process they said, ‘We’re interested in you guys because of your management team; we think you’re fantastic…’ Two weeks later they pull me into the office – before even the first board meeting – and say, ‘We want to replace you as CEO.’”

Mark Fletcher, Founders at Work

Summary: You made a commitment to the company by agreeing to a vesting schedule — the company should reciprocate and commit to you by granting acceleration upon termination.

Over time, your continuing contributions to the company will become relatively less important to its success. But the number of shares you vest every month will stay relatively large. Founders generally make their greatest contributions at the early stages of the business but their vesting is spread evenly over three to four years.

As your relative contribution to the company diminishes, everyone at the company has an incentive to terminate you and benefit ratably from the cancellation of your unvested shares. Nevertheless, in our experience, founders are allowed to vest in peace unless they are incompetent, actively harmful to the business, or clash with a new CEO.

You will probably be terminated if you clash with a new CEO.

By definition, a new CEO is hired to change the way things are and provide new leadership to the business. That he might clash with founders who previously ran the business is predictable. The CEO usually wins any disagreements or power struggles — he is the decider and he decides what is best.

The investors, board, and management will almost certainly agree to fire your ass if you continuously clash with a new CEO and you will lose your unvested shares upon termination.

Accelerate your shares if you are terminated.

50% to 100% of your unvested shares should accelerate if you are terminated without cause or you resign for good reason.

Cause typically includes willful misconduct, gross negligence, fraudulent conduct, and breaches of agreements with the company. ‘Clashing with the CEO’ is not cause. Good reason typically includes a change in position, a reduction in salary or benefits, or a move to distant location. Detailed definitions are included in the Appendix below.

Make sure you receive this acceleration whether or not your termination or resignation is in connection with a change in control of the company, such as a sale of the business. You can clash with your acquirer too.


Justify acceleration with the reciprocity norm.

Acceleration may cause consternation among your investors but it is easy to justify:

“A founder’s most important contributions generally occur in the early stages of a business but he earns his shares evenly over time. If I clash with a new CEO and he terminates me, I should receive the equity I earned with those contributions. Which will make me much more comfortable with hiring a new CEO.

The founders agreed to a vesting schedule to demonstrate our long-term commitment to the business. You have told us that the founders are critical to the company — that we are the DNA of the business. Acceleration demonstrates the company’s long-term commitment to our continuing contribution.”

This argument is an application of the reciprocity norm which requires your opponent to be fair to you if you are fair to him. Your vesting schedule locked you into a commitment to the company — that was fair — now acceleration locks the company into a commitment to you.

It is even easy to justify 100% acceleration if you are the sole founder of the business:

“Right now, I own 100% of my shares. After the financing, I will have to earn these shares back over the next four years — I’ve agreed to that. But if I’m removed from the business, I lose the right to earn my shares back. In that case, I should walk out the door with the shares I came in with.”

Avoid unfair termination with a democratic board.

As usual, the best way to avoid unfair termination and avoid hiring a bad CEO is to create a board that reflects the ownership of the company with hacks like making a new board seat for a new CEO.

Acceleration for co-founders can do more harm than good.

If you have a team of founders, acceleration upon termination can do more harm than good.

A co-founder with acceleration upon termination who wants to leave the company can misbehave and engender his termination. If the company decides to terminate him without cause to avoid possible lawsuits, your co-founder will walk away with a lot of shares. In California, it is actually very difficult to prove cause unless an employee engages in criminal activity.

If you trust your co-founders absolutely, you should negotiate as much acceleration upon termination as you can. Otherwise, you need to decide which is worse: the expected value of misbehaving co-founders who leave with a lot of shares or the expected value of leaving a lot of shares behind after your termination.

What are your experiences with vesting upon termination?

Submit your experiences and questions on vesting upon termination in the comments. We’ll discuss the most interesting ones in a future article.

Appendix: Definitions of ‘Cause’ and ‘Good reason’.

Your lawyers will help you define cause and good reason. Definitions that we have used in term sheets in the past follow. Note that the definition of good reason below assumes the company plans on hiring a new CEO at some point:

    “Cause” shall mean the occurrence of:

  1. The willful misconduct or gross negligence in performance of his duties, including his refusal to comply in any material respect with the legal directives of the Company’s Board of Directors so long as such directives are not inconsistent with a party’s position and duties, and such refusal to comply is not remedied within ten (10) working days after written notice from the Company, which written notice shall state that failure to remedy such conduct may result in termination for Cause;
  2. dishonest or fraudulent conduct, a deliberate attempt to do an injury to the Company or the conviction of a felony; or
  3. breach of the Proprietary Information and Inventions Assignment Agreement entered into with the Company.
    “Good Reason” shall be deemed to occur if:

    1. there is a material adverse change in employee’s position of employment causing such position to be of materially less stature or of materially less responsibility, including without limitation, a change of title or responsibilities normally associated with such title, without employee’s consent (other than, with respect to the Founder(s), a change, in connection with the appointment of a new CEO, to an executive officer level position with normally associated responsibilities that reports directly to the CEO or the Board of Directors),
    2. there is a reduction of more than ten percent (10%) of employee’s base compensation unless in connection with similar decreases of other similarly situated employees of the Company, or
    3. employee refuses to relocate to a facility or location more than sixty (60) miles from such employee’s principal work site; and
  1. within the one (1) year period immediately following such event the employee elects to terminate voluntarily his employment relationship with the Company.

“Because we weren’t having success finding a CEO, [our investors] insisted that we hire these managers [a temporary CEO and CFO]. That didn’t go great.”

– Tim Brady, 1st employee at Yahoo, Founders at Work

Summary: Create a new board seat for a new CEO. Don’t give him one of the common seats.

Whether you negotiate a proportional or investor-leaning board, your term sheet will probably state that the CEO of the company must fill one of the common board seats. This may seem reasonable. One of the founders is probably the CEO and you were going to elect him to the board anyway.

Don’t accept this term. The investors are looking several moves ahead of you.

If you accept this term and hire a new CEO, he will take one of the common seats. The common shareholders will not have the right to elect that seat. If the new CEO turns out to be aligned with the investors, the new coalition of CEO + investors will control the board of directors.

A new CEO may be aligned with the investors.

A new CEO will probably be a professional manager who does a lot more business with VCs than he is likely to do with you.

VCs regularly refer the CEO to promising companies. They let him co-invest in their startups. They let him invest in their venture funds. They determine his compensation in your company. Where do you think the CEO’s loyalties lie?

Most likely, a new CEO will be aligned with the investors.

A coalition of CEO + investors can hurt the company.

A coalition of a new CEO + investors can hurt the company, founders, and employees. Consider this scenario:

The company needs to raise a Series B. Your investors discourage the new CEO from shopping around for cash because they want to invest more money in the business at a low valuation. Your investors tell you not to spend time raising cash because they will put in more money: “You should focus on building the business.” You want to shop around and raise money at a high valuation but the CEO does a half-arsed job because he knows this game.

The company ends up doing the Series B with its existing investors because that is the best offer on the table. A few months later, the CEO’s shares are “right-sized” and he is happy (“We have to pay the CEO market rate, right?”). The investors have put in more money at a low valuation and they are happy. The founders and employees have been diluted and they are wondering what just happened.

This story is not unheard of in Silicon Valley.

A new CEO may be naturally inclined to dilute you.

A new CEO can develop an antagonistic relationship with the company’s founders. Founders, like everyone else, have inadequacies as leaders and managers. Their inadequacies are usually worse than the ones the company portrayed while it was recruiting and selling the new CEO.

The new CEO joins the company and naturally blames the founders for all of the existing problems in the business. Who else is there to blame? Like any new leader, he continues to blame his predecessor for the next 12 months and loses any sympathy he had for the founders. He convinces himself that he deserves more equity for his contributions even if it dilutes the founders and employees.

“These fucking founders,” he tells the investors.

“Yes, these fucking founders,” say the investors.

And on they go to find to find a mutually beneficial opportunity to right-size the CEO.

Create a new board seat for a new CEO.

These two tales of CEO-investor intrigue illustrate why a new CEO is not necessarily your friend on the board of directors. If and when you hire a new CEO, create a new board seat for him. The common board seats should always be elected by the common shareholders.

For example, adding a CEO seat to an investor-leaning board with two investors yields

2 common + 2 investors + 1 independent + 1 CEO = 6 seats

The same scenario with one investor yields

1 common + 1 investor + 1 independent + 1 CEO = 4 seats

If you want to keep an odd number of people on the board, add another independent seat too.

If you have a good BATNA, you should reject any proposal where the CEO takes one of the common board seats.

The new CEO seat maintains the board’s structure (if you’re lucky).

Your investors may argue that the new CEO seat tips the board in favor of the common stockholders since the CEO holds common stock.

If only you were so lucky.

If your investors accept the premise that the new CEO is probably aligned with them, the new seat actually tips the board in their favor. If they don’t accept this premise, they are still wrong.

First, the independent director holds common stock, but the investors do not consider his seat to tip the board in favor of the common stockholders. You should ask your investors to consistently apply the same reasoning to the new CEO seat.

Second, the CEO does not represent the common stockholders on the board; his job is to create value for all classes of stock. In fact, all of the board members have a duty to serve the interests of the company, not a duty to “serve their class of stock”.

You learn a lot about an investor’s attitude toward directorship if they imply that they represent their class of stock on the board. Investors should protect their class of stock through protective provisions, not through their board seat.