Joining an Early Stage Startup? Negotiate Your Startup Equity and Salary with Stock Option Counsel Tips
Startup equity negotiation tips for early stage founders, executives, employees, consultants and advisors.
Attorney Mary Russell counsels individuals on startup equity, including:
You are welcome to contact her at (650) 326-3412 or at info@stockoptioncounsel.com.
Startup Equity @ Early Stage Startups
"Hey baby, what's your employee number?" A low employee number at a famous startup is a sign of great riches. But you can't start today and be Employee #1 at OpenAI, Discord, or one of the other most valuable startups on Earth. Instead you'll have to join an early-stage startup, negotiate a great equity package and hope for the company’s success. This post walks through the negotiation issues in joining a pre-Series A / seed-funded / very-early-stage startup.
Q: Isn't startup equity a sure thing? They have funding!
No. Raising small amounts from seed stage investors or friends and family is not the same sign of success and value as a multi-million dollar Series A funding by venture capitalists.
Carta’s data team published an update in December of 2023 showing the “graduation rates” from Series Seed to Series A within 2 years. They affirm that it’s not a sure thing to graduate from Series Seed to Series A and, therefore, even have the chance to make it all the way to a successful acquisition or IPO. In hot years of 2021-2022, the graduation rate hovered around 30% across all industries. In 2023, it ranged from:
23% for FinTech
20% for HealthTech
19% for Consumer
17% for SaaS
16% for Biotech
Here's an illustration from Dustin Moskovitz's presentation, Why to Start a Startup from Y Combinator's Startup School on the chances so "making it" for a startup that has already raised seed funding. These 2nd Round “graduation” numbers are higher than Carta’s numbers, as this data was from 2017 (a hot hot time for startup funding).
What are the chances of a seed-funded startup becoming a "unicorn" (here, defined as having 6 rounds of funding rather than the classic “unicorn” definition of a $1 billion valuation).
Q: How do you negotiate equity for a startup? How many shares of startup equity should I get?
Don't think in terms of number of shares or the valuation of shares when you join an early-stage startup. Think of yourself as a late-stage founder and negotiate for a specific percentage ownership in the company. You should base this percentage on your anticipated contribution to the company's growth in value.
Early-stage companies expect to dramatically increase in value between founding and Series A. For example, a common pre-money valuation at a VC financing is $8 million. And no company can become an $8 million company without a great team.
Imagine, for instance, that the company tries to sell you on the offer by insisting that they will someday be worth $1B and, therefore, your equity worth, say, $1M. The obvious question would be: Does it feel fair to you to make a significant contribution to the creation of $1B in value in exchange for $1M? For most people, the answer would be “no.”
Or, consider that the company is insisting that an offer of 1% is “worth” $1M because the company expects to raise a Series A - based in part on your efforts - at a $100M pre-money valuation. Leaving aside the wisdom (or lack thereof) of evaluating the offer based on its future value, you would want to ask yourself: Does it feel fair to you to make a significant contribution to the creation of $100M in value in exchange for $1M in equity (which would presumably be only partially vested as of the Series A)?
That would depend, of course, on how significant your contribution would be. And it would depend on the salary component of the offer. If the cash compensation is already close to market level, that might seem more than fair. If the cash offer is a fraction of your opportunity cost, you would be investing that opportunity cost to earn the equity. The potential upside would need to be great enough to balance the risk of that investment.
Q: Is 1% equity in a startup good?
The classic 1% for the first employee may make sense for a key employee joining after a Series A financing, but do not make the mistake of thinking that an early-stage employee is the same as a post-Series A employee.
First, your ownership percentage will be significantly diluted at the Series A financing. When the Series A VC buys approximately 20% of the company, you will own approximately 20% less of the company.
Second, there is a huge risk that the company will never raise a VC financing or survive past the seed stage. According to CB Insights, about 39.4% of companies with legitimate seed funding go on to raise follow-on financing. And the number is far lower for seed deals in which big name VCs are not participating.
Don't be fooled by promises that the company is "raising money" or "about to close a financing." Founders are notoriously delusional about these matters. If they haven't closed the deal and put millions of dollars in the bank, the risk is high that the company will run out of money and no longer be able to pay you a salary. Since your risk is higher than a post-Series A employee, your equity percentage should be higher as well.
Q: What is typical equity for startup? How should I think about market data for startup equity?
Data sets on employee and executive offer percentages for early stage startups can be misleading and encourage companies to make unrealistically low offers to early hires. There’s two reasons for this. First, these data sets are for employees who are earning something like market level salaries along with equity. Second, these data sets exclude anyone classified as a “founder” from the data set for employees. They keep different data sets for founders! So the gray area between the two classifications makes the use of data tricky. Who is a founder for purposes of the data set? Depends on the data set. Carta, for instance, excludes anyone with 5% or more from the employee/executive data set and classifies them as founders! Even if they are earning market-level cash from their start date.
Here’s the bottom line:
If you are joining before you are being paid startup-phase-market-level cash salary, you are a late stage founder. You should evaluate your equity percentage relative to the other founders within the company or within the market data set.
If you are joining for a combination of cash and equity at an early stage startup, the offer should make sense to you. Simply pointing to market data for the right % ownership is not enough. You’ll want to consider the market data for % ownership in conjunction with the dollar value of the equity based on how investors have most recently valued the company.
Q: How should early-stage startups calculate my percentage ownership?
You'll be negotiating your equity as a percentage of the company's "Fully Diluted Capital." Fully Diluted Capital = the number of shares issued to founders ("Founder Stock") + the number of shares reserved for employees ("Employee Pool") + the number of shares issued to other investors (“preferred shares”). There may also be warrants outstanding, which should also be included. Your Number of Shares / Fully Diluted Capital = Your Percentage Ownership.
Careful, though, because most startups do not issue preferred stock when they take their seed investment funds from their seed investors. Instead, they issue convertible notes or SAFEs. These convert into shares of preferred stock in the next round of funding. So if you negotiate for 1% of a seed stage startup funded with notes or SAFEs, the fully diluted capital number used as the denominator of that calculation does not include the shares to be issued for those seed funds.
How can you address this? First, make sure you know what’s included. You can ask:
How many shares are outstanding on a fully diluted basis? Does this include the full option pool? Are there any shares yet to be issued for investments in the company, such as on SAFEs or convertible notes? How many shares do you expect to issue upon their conversion?
If you are comparing your offer to other seed stage offers or to market data for seed stage offers, you would want to take that into consideration. The number the company provides is only an estimate, of course, but it’s a way to address this in your evaluation.
“Fully Diluted Capital” includes only issued shares and reserved shares. For an early stage startup, that would include founders shares, the option pool, and any preferred shares issued to investors in a priced round. It will not include shares to be issued upon conversion of SAFEs and convertible notes. Therefore, you will want to include some estimate for the conversion of those investments when you are understanding the percentage ownership in an early stage startup offer.
Q: Is there anything tricky I should look out for in my startup equity documents?
Yes. Look for repurchase rights for vested shares.
If so, you may forfeit your vested shares if you leave the company for any reason prior to an acquisition or IPO. In other words, you have infinite vesting as you don't really own the shares even after they vest. This can be called "vested share repurchase rights," "clawbacks” or "non-competition restrictions on equity.”
Most employees who will be subject to this don't know about it until they are leaving the company (either willingly or after being fired) or waiting to get paid out in a merger that is never going to pay them out. That means they have been working to earn equity that does not have the value they think it does while they could have been working somewhere else for real equity.
According to equity expert Bruce Brumberg, "You must read your whole grant agreement and understand all of its terms, even if you have little ability to negotiate changes. In addition, do not ignore new grant agreements on the assumption that these are always going to be the same." When you are exchanging some form of cash compensation or making some other investment such as time for the equity, it makes sense to have an attorney review the documents before committing to the investment.
Q: What is fair for vesting of startup equity?
The standard vesting is monthly vesting over four years with a one year cliff. This means that you earn 1/4 of the shares after one year and 1/48 of the shares every month thereafter. But vesting should make sense. If your role at the company is not expected to extend for four years, consider negotiating for a vesting schedule that matches that expectation.
Q: Should I agree to milestone or performance metrics for my vesting schedule for startup equity?
No. This is a double risk. Not only is there a high risk that the company will not be successful (and the equity worthless), there is a high risk that the milestones will not be met. This is very often outside the control of the employee or even the founders. More on this issue here. The standard is four-year vesting with a one-year cliff. Anything else is off-market and is a sign that the founders are trying to be too creative and reinvent the wheel.
Q: Should I have protection for my unvested shares of startup equity in the event of an acquisition?
Yes. When you negotiate for an equity package in anticipation of a valuable exit, you would hope that you would have the opportunity to earn the full number of shares in the offer so long as you are willing to stay through the vesting schedule.
If you do not have protection for your unvested shares in the stock documents, unvested shares may be cancelled at the time of an acquisition. I call this a “Cancellation Plan.”
Executives and key hires negotiate for “double trigger acceleration upon change of control.” This protects the right to earn the full block of shares, as the shares would immediately become vested if both of the following are met: (1st trigger) an acquisition occurs before the award is fully vested; and (2nd trigger) the employee is terminated after closing before they are fully vested.
There’s plenty of variation in the fine print of double trigger clauses, though. Learn more here.
Q: The company says they will decide the exercise price of my stock options. Can I negotiate that?
A well-advised company will set the exercise price at the fair market value ("FMV") on the date the board grants the options to you. This price is not negotiable, but to protect your interests you want to be sure that they grant you the options ASAP.
Let the company know that this is important to you and follow up on it after you start. If they delay granting you the options until after a financing or other important event, the FMV and the exercise price will go up. This would reduce the value of your stock options.
Early-stage startups very commonly delay making grants. They shrug this off as due to "bandwidth" or other nonsense. But it is really just carelessness about giving their employees what they have been promised.
The timing and, therefore, price of grants does not matter much if the company is a failure. But if the company has great success within its first years, it is a huge problem for individual employees. I have seen individuals stuck with exercise prices in the hundreds of thousands of dollars when they were promised exercise prices in the hundreds of dollars.
Q: What salary can I negotiate as an early-stage employee?
When you join an early-stage startup, you may have to accept a below market salary. But a startup is not a non-profit. You should be up to market salary as soon as the company raises real money. And you should be rewarded for any loss of salary (and the risk that you will be earning $0 salary in a few months if the company does not raise money) in a significant equity award when you join the company.
When you join the company, you may want to come to agreement on your market rate and agree that you will receive a raise to that amount at the time of the financing.
I sometimes see people ask at hire to receive a bonus at the time of the financing to make up for working at below-market rates in the early stages. This is a gamble, of course, because only a small percent of seed-stage startups would ever make it to Series A and be able to pay that bonus. Therefore, it makes far more sense to negotiate for a substantial equity offer instead.
Q: What form of startup equity should I receive? What are the tax consequences of the form?
[Please do not rely on these as tax advice to your particular situation, as they are based on many, many assumptions about an individual's tax situation and the company's compliance with the law. For example, if the company incorrectly designs the structure or the details of your grants, you can be faced with penalty taxes of up to 70%. Or if there are price fluctuations in the year of sale, your tax treatment may be different. Or if the company makes certain choices at acquisition, your tax treatment may be different. Or ... you get the idea that this is complicated.]
These are the most tax advantaged forms of equity compensation for an early-stage employee in order of best to worst:
1. [Tie] Restricted Stock. You buy the shares for their fair market value at the date of grant and file an 83(b) election with the IRS within 30 days. Since you own the shares, your capital gains holding period begins immediately. You avoid being taxed when you receive the stock and avoid ordinary income tax rates at sale of stock. But you take the risk that the stock will become worthless or will be worth less than the price you paid to buy it.
1. [Tie] Non-Qualified Stock Options (Immediately Early Exercised). You early exercise the stock options immediately and file an 83(b) election with the IRS within 30 days. There is no spread between the fair market value of the stock and the exercise price of the options, so you avoid any taxes (even AMT) at exercise. You immediately own the shares (subject to vesting), so you avoid ordinary income tax rates at sale of stock and your capital gains holding period begins immediately. But you take the investment risk that the stock will become worthless or will be worth less than the price you paid to exercise it.
3. Incentive Stock Options ("ISOs"): You will not be taxed when the options are granted, and you will not have ordinary income when you exercise your options. However, you may have to pay Alternative Minimum Tax ("AMT") when you exercise your options on the spread between the fair market value ("FMV") on the date of exercise and the exercise price. You will also get capital gains treatment when you sell the stock so long as you sell your stock at least (1) one year after exercise AND (2) two years after the ISOs are granted.
Q: Who will guide me if I have more questions on startup equity?
Attorney Mary Russell counsels individuals on startup equity, including:
You are welcome to contact her at (650) 326-3412 or at info@stockoptioncounsel.com.
Company-Side Education Programs on Startup Equity - Feedback from Newsletter Subscribers
Here’s a quick primer on how to negotiate stock options or RSUs in a startup. It's up to individuals to educate and empower themselves when company-side education programs are lacking. Photo by Alena Darmel.
Attorney Mary Russell counsels individuals on startup equity, including:
You are welcome to contact her at (650) 326-3412 or at info@stockoptioncounsel.com.
I asked my newsletter subscribers to share their experiences with startup company employee equity education programs. Thank you for all your responses! I love being in touch and hearing your feedback.
See below under My Takeaways for a quick primer on how employees can empower themselves by taking the initiative to learn about startup equity and ask their companies for the information they need to make informed decisions.
Individuals reported these company programs they found very helpful:
Company all-hands meetings followed by both (1) smaller working groups led by the CEO/CFO using real world tangible scenarios to explain and provide context and (2) one-on-ones with senior management.
Training sessions with the company’s CFO.
Carta, including blog content, presentations, Equity 101 posts, and online calculators. “Very good interface with clear information.”
Individuals reported these company programs they found somewhat helpful:
Company-wide information meeting on stock options, but not provided until years after the employee joined the company.
Carta as stock administrator. This allows employees to “have more access and run the calculator more frequently. But it doesn’t speak to the non-price issues like post-termination exercise periods, forced share repurchase,” etc. Also, “Carta maximizes for startup friendliness, and here employee friendliness runs counter to that goal.”
ShareWorks as stock administrator. The “account includes the value of your options based on the latest valuation. From a user experience, [though,] it is clunky like most financial software products.”
Individuals reported these company programs they found not helpful or harmful:
Company education program on stock option exercise by a stock broker who was “in it for himself and not the employees. … The education they were offering was to inform the newly wealthy employees how to “invest” their new found cash. It is not a good strategy to use someone like that for that purpose … I lost about $1M of the money I earned from the startup. It was disastrous. If companies host an individual, make sure they are fiduciaries and not brokers.”
Company-wide information meeting with general information and many disclaimers, which was “not that helpful for making actionable decisions. … I think the presentations backfired because most either didn’t understand options any better than they did prior to the meeting and those that did realized their options weren’t that valuable (which was the opposite motivation of the CEO).”
In a geographic area where “most employees aren’t stock option aware …, although we granted stock options to all employees, most ignored them because they were difficult to understand. And HR was unable to answer any questions about options because they didn’t understand them. … In the case of recruiting and offers -- the lore was more important than the facts.”
Recruiters who “fail to disclose the material issues, and sometimes state that the equity situation is more favorable than it actually is.”
Individuals reported these wish-list items they had not yet seen:
“If this were my project, I would use a framework of virtual recorded introductory education sessions that give the basics of the compensation program, and a one-on-one follow up to cover any lingering questions. I would build out a self-help knowledge base that covers common lingering questions and/or use that info to improve the education sessions.”
“I like the idea of a 3rd party to provide the trainings, mixed with key staff or founder interaction to build trust.”
Examples, simplicity, transparency and opportunities for lots of Q&A in small groups. A library of content that addresses common questions, concerns and misconceptions would also be very valuable.
“It would be great if our law firm had established programs to walk us through the process.”
“What employees really want to know is -- what is the value of my options under various realistic scenarios. One approach might be several if-then scenarios and then employees can decide which one of those hypothetical scenarios most applies to them.”
“Options seem to be presented as a commodity component to most offerings with a presumed windfall. … It’s important to manage expectations of what the value is and how to think about that; how to act, when, why.”
An educational program would need to provide an “overview, some tools for employees to calculate future sums/ exit projections (dream a bit), and cover common tax issues, maybe an overview of company/venture process (what the near future could mean for equity holders), and gotchas like: what happens to my vested equity if I have to leave the company.”
Services providers reported these as service offerings they had available to companies:
Note: If you are a service provider in this area with an offering I have not included, please send me an email with a description of your services so I can add it to the list.
Dan Walter, FutureSense. Dan advises companies on executive pay, equity compensation, incentive compensation, and pay for performance. He says that employee education “is a normal piece of our deliverables for nearly every company we work with.” I’ve seen him speak on these topics and he has, as promised, “a unique ability to help anyone understand even the most complex and technical details in ways that are approachable and memorable.”
Bruce Brumberg, myStockOptions.com. Bruce’s site, myStockOptions.com, is the “premier source of web-based educational content and tools on stock compensation for plan participants, financial advisors, companies, and stock plan providers.” They license their educational resources to companies for their programs.
Tom Bondi, CPA, Armanino, LLP. Tom offers company-side employee stock/equity training programs to companies with from 25-500 employees, where the companies wish to give back to their employees with knowledge they are not able to offer.
Financial Advisors who are available to companies in the run-up to an IPO or acquisition to educate the company’s employees.
Carta’s Tax Advisory. Updated February 2023: This add-on to Carta’s cap table service allows startups to help their employees make tax decisions around their equity. Employees of subscribing companies have access to one-on-ones with tax advisors such as: Ask a Quick Question (15 minutes), Understand Equity Tax Basics (30 minutes), Create Tax Scenarios (45 minutes) and Discuss Tender Offer Participation (30 minutes).
My takeaways:
Some company-side education programs are helpful to employees in navigating their equity. However, it is up to individual employees to empower themselves by taking the initiative to learn about startup equity and ask their companies for the information they need to make informed decisions.
Here’s a quick primer on how individuals can do this (based on this blog post):
Number of Shares. The offer letter may include the number of shares, but this number is certainly not all you need to evaluate and negotiate the offer. I encourage candidates to ask questions about the equity package and number of shares until they have the information they need to make an informed decision. More on evaluating the number of shares in an offer letter here.
Equity Grant Form Documents. The equity incentive plan and form stock option agreement contain important details about the equity grant, so it makes sense to request and review them before signing the offer letter. These agreements may give the company clawback rights for vested shares or other terms that may dramatically limit the value of the equity offer. If these red flags appear in the form documents, it makes sense to negotiate to remove them from your individual grant or add additional compensation to make up for that loss in value.
Tax Structure. The right tax structure for an option or RSU offer will balance your interests in total value, low tax rates, tax deferral and investment deferral. This balance is different for each individual and at each company stage. You will want to have a tax strategy in mind before accepting the offer letter, so you can negotiate any necessary terms to enable that strategy as part of the offer letter itself.
Attorney Mary Russell counsels individuals on startup equity, including:
You are welcome to contact her at (650) 326-3412 or at info@stockoptioncounsel.com.