The Most Common Option Grant Mistakes

This is a post I should’ve written years ago because it involves issues our firm sees from startups on a weekly basis. These are the most common mistakes – often very, very expensive mistakes – that we see startups make in granting options to employees, contractors, advisors, etc.

1. Not understanding the (big) difference between promising options and granting options.

With respect to issuing any form of equity for services, there’s usually 2 broad steps: first you promise the equity in an offer letter, consulting agreement, advisor agreement, etc., and then after that agreement has been signed, further steps have to be taken to grant the equity, including with a Board consent.

We constantly see startups pile up offer letters and other documents promising options to people, and waiting months or even years before someone conducting diligence – often in prep for a financing – realizes that none of those options were ever granted. One might think that cleaning this up is simple enough, but it’s often not. For tax purposes, option grants need to be issued with an exercise/strike price equal to their fair market value on the day they are granted (not promised).

If you hire an employee on January 1st 2020 and promise them options, they are expecting to receive an exercise price close to the equity value on the day they signed their offer letter; especially if they’re an early employee and the idea of getting “cheap” equity was part of their reason for joining. Imagine if you sit on that offer letter until June 15, 2021, after which the company has hit multiple milestones and even raised some seed money putting a value on the company 10x of what it was a year and a half ago? When you finally get around to granting those options, the strike price now has to be equal to the higher value, and the employee has lost all of that upside. Think they’re going to be happy?

We’ve seen dozens of companies make this mistake. In the worst scenarios it often leads to a threatened lawsuit, or the need for the company to materially increase the amount of equity the recipient receives in order to make up for the lost value. Other times it just results in some very very disappointed employees, and loss of goodwill.

Promising equity is as simple as signing a napkin with a few sentences. Granting equity requires valuations, consents, and well-structured equity plan documentation managed by lawyers. This is not something to DIY.

2. Getting Board approval but never delivering the (important) grant documentation.

In this instance, the Company did take the main step of properly having grants approved by the Board, but they never finished the job by actually delivering the appropriate grant documentation to the recipients.

The reason this can be a big problem is that the option grant documentation (including the appropriate equity incentive plan) will have a number of important provisions around rights the recipient and/or company have with respect to the grant. For example, it will say what happens in an acquisition, have specifics around how vesting works, or set expectations around the expiration or termination of the option. By failing to actually deliver the grant documentation to the option recipient, the Company opens itself up to arguments that all those provisions are not enforceable; which can mean litigation when the stakes get high.

Offer letters often say nothing about how a vesting schedule, or exercise period, works in the event of an employee’s resignation. Those details are in the (much much longer) grant documentation. By failing to ever deliver that documentation, you open yourself up to claims by employees that their equity continues vesting, or continues being exercisable, regardless of what the documents (that they never received) say, or what you intended for their “deal” to be.

3. Not having a 409A valuation, or having a stale valuation. 

Option grants need to be issued with an exercise price equal to or greater than the fair market value of the equity on the grant date, to comply with IRS rules that ensure no one gets a tax hit on the grant date. The IRS does not accept any equity value the company decides on. It has special requirements, including “safe harbors,” for setting the value. The most common safe harbor used is to get a professional valuation report from a reputable valuation company, like Carta.

Some companies mess up by issuing options at a price that really doesn’t make sense given the state of the business, and they don’t have a valuation report to back it up.

Other companies fail to understand that valuation reports don’t last forever. If you do another financing, you almost always need a new valuation. And if any kind of business milestone is achieved that would realistically change the value of the business – like a substantial increase in revenue – the valuation also needs to be updated. If your valuation is 9 months old, the business has doubled in size since then, and you grant options with that 9-month-old price, you almost certainly have a tax problem, for which the penalties can be substantial. After 12 months, all valuations have to be refreshed.

4. NSOs (or NQSOs) v. ISOs.

There are so many articles already written on this topic that you can find with any online search, so I’m not going to go deep into it. Just understand that employees and independent contractors do not receive the same kind of option grant, for tax reasons. Employees receive ISOs, which are usually more tax favorable. Independent Contractors receive NSOs. The documentation is slightly different.

5. Not tracking vesting schedules and exercise period expiration properly. 

Vesting schedule calculations often aren’t super straightforward. When someone leaves the company and has a portion of vested and a portion of unvested equity, someone needs to verify that the unvested equity is actually being reflected as terminated and removed from the cap table. If the equity plan also has provisions around the expiration of vested equity if it goes unexercised for a period of time post-termination (most plans do), someone needs to track that as well and ensure the cap table stays updated. Something like Carta can help a lot here, but we still regularly see people make mistakes and/or use the wrong numbers.

Companies often forget to remove terminated unvested equity (when someone leaves the company) from a cap table, or to remove a grant that has fully expired. This can create problems long-term if they inadvertently allow the person to later exercise their option (which really should no longer exist), or if they are doing other calculations, or making representations, with an incorrect cap table.

6. Promising a percentage instead of a fixed number of shares.

When companies are discussing an equity grant with an employee or other service provider, they usually speak in terms of percentages, which is good and transparent. Promising someone 100,000 shares can be meaningless if they don’t know what the denominator is. But when they actually move to document the arrangement, they should use a fixed number of shares.

By documenting a % instead of the corresponding fixed number of shares, one of two problems can arise. First, if it’s not made abundantly clear in the same document that the % is calculated as of a specific date, the company opens itself up to claims that the % is indefinite (non-dilutable). Second, if the company makes the mistake of failing to actually grant the option quickly after they’ve promised the % (See #1 above), by the time they get around to granting the option, the cap table may have changed significantly. 2% Pre-Seed is a very different deal from 2% Post-Series A. I’ve seen this mistake get very ugly.

7. Generally sloppy drafting.

“The options will vest over 48 months.”

I can’t tell you how many companies will put a sentence like this into an offer letter or option grant. Can you tell what’s wrong with it?

How will it vest over the 48 months? In equal portions each month, or some other way? When exactly does it start (offer date or employment date)? What is the vesting conditioned on? It doesn’t say anywhere that actually providing services is a requirement. Does it continue vesting even if the person is terminated? What if they leave? What if an acquisition happens?

ECVC lawyers have language banks that they rely on for situations like this to quickly and efficiently capture a concept, but with language that they know works because it’s been used 1,000 times. Nine times out of ten when a company thinks they’re saving money or time by freestyle drafting a vesting schedule themselves, it backfires.

Being well-organized can get you far in terms of avoiding the most expensive legal mistakes commonly made by startups, but given all the corporate, securities, and tax-related nuances around issuing high-valued equity in private companies, there’s always a lot that entrepreneurs don’t know that they don’t know.

The key message here is: don’t think it’s simpler than it really is (it’s not), and work with people who truly know what they’re doing. The easiest and most efficient way to stay safe is to work closely with an experienced paralegal at an ECVC law firm.

Paralegals are a fraction of the rate of the senior lawyer/partner who is likely your main point of contact on legal, but they are (at least at good firms) extremely well trained to monitor and catch these sorts of issues around equity grants, because they help process hundreds/thousands of grants a year. I’ve also too often seen companies work with over-worked solo lawyers (detached from a firm) who have no access to specialized paralegals, and in rushing review/processing they make the same mistakes founders might make. Because paralegals are cheaper, they can take the necessary time and ensure all the boxes get checked.

A Convertible Note Template for Startup Seed Rounds

TL;DR: We’ve created a publicly downloadable template for a seed convertible note (with useful footnotes), based on the template we’ve used hundreds of times in seed convertible note deals across the U.S. (outside of California). It can be downloaded here.

Background reading:

I’ve written several posts on structuring seed rounds, and how for seed rounds on the smaller side ($250K-$1MM) convertible notes are by far the dominant instrument that we see across the country. When SAFEs had pre-money valuation caps, they gained quite a bit of traction in Silicon Valley and pockets of other markets, but outside of SV convertible notes were still the dominant convertible instrument. Now that YC has revised the SAFE to have harsher post-money valuation economics (see above linked post), we’re seeing SAFE utilization drop significantly, though it was never close to the “standard” to begin with; at least not outside of California. For most seed companies, convertible notes and equity are the main options. 

For rounds above $1-1.5MM+, equity (particularly seed equity) should be given strong consideration. We are also seeing more founders and investors who really prefer equity opting for seed equity docs for rounds as low as $500K. The point of this post isn’t to get into the nuances of convertibles v. equity. There’s a lot of literature out there on the topic, including here on SHL.

What this post is really about is that many people have written to me regarding the absence of a useable public convertible note template that lawyers and startups can leverage for seed deals; particularly startups outside of SV, which has very different norms and investor expectations from other markets. Our boutique firm, Egan Nelson (E/N), specializes in emerging companies work outside of California: markets like Austin, Seattle, NYC, Boston, etc. We see a lot of seed deals every year across the country. Here is a list of funds our lawyers have worked across from in negotiating financings. Here is my personal bio to confirm I’m not just some random guy with a blog.

Cooley actually has a solid convertible note available on their Cooley GO document generator. I’m a fan of Cooley GO. It has strong content. But as many readers know, there are inherent limitations to these automated doc generator tools; many of which law firms utilize more for marketing reasons (a kind of techie signaling) than actual day-to-day practical value for real clients closing real deals. Your seed docs often set the terms for issuing as much as 10-30% of your company’s capitalization, and the terms of your long-term relationship with your earliest supporters. Take the details seriously, and take advantage of the ability to flexibly modify things when it’s warranted.

The “move fast and mindlessly sign a template” approach has for some time been peddled by pockets of very clever and vocal investors, who know that pushing for speed is the easiest way to take advantage of inexperienced founders who don’t know what questions to ask. But the smartest teams always slow down enough to work with trusted advisors who can ensure the deal that gets signed makes sense for the context, and that the team really knows what they’re getting into. Taking that time can easily pay off 10-20x+ in terms of the improved cap table or governance position you get from a little tweaking. The investor trying to rush your deal isn’t really trying to save you legal fees. They’re trying to save themselves from having to negotiate, or justify the “asks” in their docs.

As a firm focused on smaller ecosystems that typically don’t get nearly as much air time in startup financing discussions as SV, I realized we’re well-positioned to offer non-SV founders a useful template for convertible notes. The fact that, to avoid conflicts of interest, we also don’t represent Tech VCs (trust me, many have asked, but it’s a hard policy) also allows us to speak with a somewhat unique level of impartiality on what companies should be accepting for their seed note deals. There are a lot of players in the startup ecosystem that love to use their microphones to push X or Y (air quotes) “standard” for startup financings, but more often than not their deep ties to certain investors should raise doubts among founders as to biases in their perspective. We’ve drafted this template from the perspective of independent company counsel. 

So here it is: A Convertible Note Template for Seed Rounds, with some useful footnotes for ways to flexibly tweak the note within deal norms. Publicly available for download.

A few additional, important points to keep in mind in using this note:

First, make sure that the lawyer(s) you are working with have deep (senior) experience in this area of law (emerging companies and vc, not just general corporate lawyers), and don’t have conflicts of interest with the people sitting across the table offering you money. When investors “recommend” a specific law firm they are “familiar” with they’re often trying to strip startup teams of crucial strategic advice. See: Checklist for Choosing a Startup Lawyer. Be very careful with firms that push this kind of work to paralegals or juniors, who inevitably work off of an inflexible script and won’t be able to tailor things for the context. You want experienced, trustworthy specialists; not shills or novices.

Second, be mature about maturity. You’re asking people to hand you money in a period of enormous uncertainty and risk, while getting very little protection upfront. As long as maturity is long enough to give you sufficient time to make things happen (2-3 yrs is what we are seeing), you shouldn’t run away from the most basic of accountability measures in your deal. Think about how bad of a signal it sends to investors if a 3 year deadline terrifies you.

Third, do not for a second think that, because you have a template in your hand, it somehow means you no longer need experienced advisors, like lawyers, to close on it. Template contracts don’t remove the need for lawyers any more than GitHub removes the need for developers. The template is a starting point, and the real expertise is in knowing which template to start from, and how to work with it for the unique context and parties involved. Experienced Startup Lawyers are incredibly useful “equalizers” when first-time entrepreneurs are negotiating with experienced money players. Don’t get played.

Fourth, pay very close attention to how the valuation cap works, particularly the denominator used for ultimately calculating the share price. We are seeing more openness among investors to “hardening” the denominator at closing, either with an actual capitalization number, or by clarifying that any changes to the option pool in a Series A won’t be included. These modifications make notes behave more like equity from a dilution standpoint, allowing more clarity around how much of the company is being given to the seed money.

Finally, don’t try to force this template on unwilling investors. It can irritate seasoned investors to no end to hear that they must use X template for a deal because some blog post, lawyer, or accelerator said so. There is no single “standard” for a seed round. There never has been, and never will be, because different companies are raising in different contexts with investors who have different priorities and expectations. We’ve used this form hundreds of times across the country, but that doesn’t mean there aren’t other perfectly reasonable ways to do seed deals.

Have a dialogue with your lead money, and use that dialogue to set expectations. See: Negotiation is Relationship Building. If they’re comfortable using this template, great. If they need a little extra language here or there, don’t make a huge fuss about it if your own advisors say it’s OK. And if they prefer another structure, like seed equity or even more robust equity docs, plenty of companies do that for their seed round and it goes perfectly fine, as long as you have experienced people monitoring the details.

If any experienced lawyers out there see areas of improvement for the template, feel free to ping me via e-mail.

Obligatory disclaimer: This template is being provided as an educational resource, and is intended to be utilized by experienced legal counsel with a full understanding of the context in which the template is being used. We (myself or Egan Nelson LLP) are not responsible at all for the consequences of your utilization of this template. Good luck.

How Startup Employees Get Taken Advantage Of

TL;DR: When startup employees get taken advantage of in startup equity economics, it’s often not just about bad documentation or strategy. It’s about incentives, and games being played by influential “insiders” to gain control over the startup’s corporate governance. Ensuring common stock representation on the Board, independence of company counsel (from investors), and monitoring “sweeteners” given to common representatives on the Board are strong strategies for protecting against bad actors.

Related Reading:

A common message heard among experienced market players, and with which I completely agree, is this: if you are seeing significant dysfunction in any organization or market, watch incentives. In small, simple, close-knit groups (like families and tribes), shared principles and values can often be relied on to ensure everyone plays fairly and does what’s best for the group.  But expand the size of the group, diversify the people involved, and raise the stakes, and people will inevitably gravitate toward their self-interest and incentives. The way to achieve an optimal and fair outcome at scale is not through “mission statements” or virtue signaling, but focusing on achieving alignment (where possible) of incentives, and fair representation of the various constituencies at the bargaining table.

A topic that is deservedly getting a lot of attention lately is the outcomes of startup employees as it relates to their equity stakes in the startups that employ them. I see a lot being written about it in the various usual tech/startup publications, and we are also seeing companies reaching out to us asking about potential modifications to the “usual” approaches.  The problem being discussed is whether startup employees are getting the short end of the stick as companies grow and scale, with other players at the table (particularly the Board of Directors) playing games that allow certain players to get rewarded, while off-loading downside risk to those unable to protect themselves.

The short answer is that, yes, there are a number of games being played in the market that allow influential “insiders” of growing startups to make money, while shifting risk to the less powerful and experienced participants on the cap table. The end-result is situations where high-growth startups either go completely bust, or end up exiting at a price that didn’t “clear” investors’ liquidation preferences, and yet somehow a bunch of people still made a lot of money along the way, while startup employees got equity worth nothing.

The point of this post isn’t to discuss the various tactics being used by aggressive players to screw employees, but to discuss a higher-level issue that is closer to the root problem: corporate governance, and the subtle detachment of employee equity economics from other cap table players. When some people on the Board have economic incentives close to fully aligned with employees (common stockholders whose “investment” is labor, not capital, and often sunk), they are significantly more likely to deliver the necessary pushback to protect employees from absorbing more risk than is appropriate.  But if smart players find ways to detach those Board members’ interests from the employees who can’t see the full details of the company’s financing and growth strategy, things go off the rails.

Corporate governance and fiduciary duties.

Broadly speaking, corporate governance is the way in which a company is run at the highest levels of its organizational and power structure, particularly the Board of Directors. Under Delaware law (and most states/countries’ corporate law), the Board has fiduciary duties to impartially serve the interests of the stockholders on the cap table. Regardless of their personal interests, a Board is supposed to be focused on a financing and exit strategy that maximizes the returns for the whole cap table, particularly those at the bottom of the liquidation preference stack and who lack the visibility, influence, and experience to negotiate on their own behalf. That obviously includes, to a large extent, employee stockholders.

This is, of course, easier said than done. Remember the fundamental rule: watch incentives. Having a Board of directors that nominally professes a commitment to its fiduciary duties is one thing. But maximizing economic alignment between the Board and the remainder of the cap table is lightyears better.

“One Shot” common stockholders v. “Repeat Player” investors

As I’ve written many times before, anyone who behaves as if investors (capital) and founders/employees (labor) are fully aligned economically as startups grow, raise money, and exit is either lying, or so spectacularly ignorant of how the game actually works that they should put the pacifier back in their mouth and gain more experience before commenting.

Common stockholders (founders, employees) are usually inexperienced, not wealthy, at the bottom of the liquidation “waterfall” (how money flows in an exit), not independently represented by counsel, and not diversified. Preferred stockholders (investors) are usually the polar opposite: highly experienced, wealthy, have their own lawyers, heavily diversified, and with a liquidation preference or debt claim that prioritizes their investment in an exit. Common stockholders’ “investment” (their labor) is also often sunk, while major investors have pro-rata rights that allow them to true-up their ownership if they face dilution.

Investors are far more incentivized to push for risky growth strategies that might achieve extremely large exits, but also raise the risk of a bust in which the undiversified, unprotected common equity gets nothing. Common stockholders are far more likely to be concerned about risk, dilution and dependence on capital, and the timing / achievability of an exit. This tension never goes away, and plays out in Board discussions on an ongoing basis.

As I’ve also written before, this is a core reason why clever investors will often pursue any number of strategies to put in place company counsel (the lawyers who advise the company and the Board) whose loyalty is ultimately to the investors. A law firm whom the money can “squeeze” – like one that heavily relies on them for referrals, or who does a large volume of other work for the investors – is significantly more likely to stay quiet and follow along if a Board begins to pursue strategies that favor investor interests at the expense of common interests. See: When VCs “own” your startup’s lawyers. 

When Board composition is discussed in a financing, founder representation on the Board is often portrayed as being purely about the founders’ own personal interests; but that’s incorrect. Founders are often the largest and earliest common stockholders on the cap table, which heavily aligns them economically with employees, particularly early employees, in being concerned about risk and dilution.

Unless someone finds a way to change that alignment.

Founders and employees: alignment v. misalignment.

Very high-growth companies raising large late-stage rounds represent many opportunities for Boards to “buy” the vote of founders or other common directors (like professional CEOs) at the expense of the employee portion of the cap table. In a scenario where a Board is pursuing an extremely high risk growth and financing strategy, and accepting financing terms making it highly likely the early common will get washed out or heavily diluted, a typical entrepreneur with a large early common stock stake will play their role in vocally pushing for alternatives.

But any number of levers can be pulled to silence that push-back: a cash bonus, an opportunity for liquidity that isn’t shared pro-rata with the rest of the employee pool, a generous refresher grant given post-financing to reduce the impact on the founder/executive (while pushing more dilution onto “sunk” stockholders). These represent just a few of the strategies that clever later-stage investors will implement to incentivize entrepreneurs (or other executives) to ignore the risk and dilution they are piling onto employees.

Of course, it’s impossible to generalize across all startups that end up with bad, imbalanced outcomes. The fact that any particular company ended up in a spot where the employees got disproportionately washed out isn’t indicative in and of itself that unfair (and unethical) games were being played. Sometimes there’s a strong justification for giving a limited number of people liquidity, while denying it to others. Sometimes the Board really was doing its best to achieve the best outcome for the “labor” equity. Sometimes.

Principles for protecting employee stockholders.

That, however, doesn’t mean there aren’t general principles that companies can implement to better protect employee stockholders, and better align the Board with their interests.

First, common stockholder representation on a Board of Directors is not just about founders. It’s about recognizing the misalignment of incentives between the “one shot” common stock and the “repeat player” preferred stockholders, and ensuring the former have a real, unmuzzled voice in governance. Founders are the largest and earliest common stockholders, and therefore the most incentivized to represent the interests of the common in Board discussions.

Second, take seriously who company counsel is, and make sure they are independent from the influence of the main investors on the cap table. Company counsel’s job is, in part, to advise a Board on how to best fulfill its fiduciary duties. You better believe the advisory changes when the money has ways to make counsel shut up. Packing a company with people whom the money “owns” (including executives, lawyers, directors, and other advisors) is an extremely common, but often subtle and hidden, strategy for aggressive investors to gain power over a startup’s governance.

Third, any “extra” incentives being handed to Board representatives of the common stock (including founders) in later-stage rounds deserve heightened scrutiny and transparency. That “something extra” can very well be a way to purchase the vote of someone who would otherwise have called out behavior that is off-loading risk to stockholders lacking visibility and influence.

Startup corporate governance is a highly intricate, multi-step game of 3D chess, often with extremely smart players who know where their incentives really lie. Don’t get played.

p.s. the NYT article linked near the beginning of this post is provided strictly as an example of the kinds of problems that might arise in high-growth startups. I have no inside knowledge of what happened with that specific company, and this post is not about them. 

The Problem with Short Startup Term Sheets

TL;DR: Shorter term sheets, which fail to spell out material issues and punt them to later in a financing, reflect the “move fast and get back to work” narrative pushed by repeat players in startup ecosystems, who benefit from hyper-standardization and rapid closings. First-time entrepreneurs and early employees are better served by more detailed term sheets that ensure alignment before the parties are locked into the deal.

Related reading:

In my experience, there are two “meta-narratives” floating around startup ecosystems regarding how to approach “legal” for startups.

The first, most often pushed by repeat “portfolio” player investors, and advisors aligned with their interests, is that hyper-standardization and speed should be top priorities. Don’t waste time on minutiae, which just “wastes” money on legal fees. Use fast-moving templates to sign a so-called “standard” deal.  Silicon Valley has, by far, adopted this mindset the furthest; facilitated in part by the “unicorn or bust” approach to company building that its historically selected for.

An alternative narrative, which you hear less often (publicly) because it favors “one shot” players with less influence, is that there is a fundamental misalignment of interests between those one shot players (founders/employees, common stockholders) and the repeat players (investors, preferred stockholders), as well as a significant imbalance of experience between the two camps. Templates publicized by repeat players as “standard” are therefore suspect, and arguments that it’s *so important* to close on them fast should cause even more caution.

Readers of SHL know where I stand on the issue (in the latter camp).  Having templates as starting points, and utilizing technology to cut out fat (and not muscle), are all good things; to a point. Beyond that point, it becomes increasingly clear that certain investors, who are diversified, wealthier, and have downside protection, use the “save some legal fees” argument to cleverly convince common stockholders to not ask hard questions, and not think about whether modifications are warranted for their *specific* company. Hyper-standardization is great for a diversified portfolio designed for “power law” returns. It can be terrible for someone whose entire net worth is locked into a single company.

Among lawyers, where they stand on this divide often depends (unsurprisingly) on where their loyalties lie. See: When VCs “Own” Your Startup’s LawyersKnowing that first-time founders and their early employees often have zero deal experience, and that signing a term sheet gets them “pregnant” with a “no shop” and growing legal fees, it’s heavily in the interest of VCs to get founders to sign a term sheet as fast as possible. That’s why lawyers who are “owned” by those repeat players are the quickest to accept this or that “standard” language, avoid rocking the boat with modifications, and insist that it’s best for the startup to sign fast; heaven forbid a day or two of comments would cause the deal to “fall through.”

I was reminded of this fact recently when Y Combinator published their “Standard and Clean” Series A Term Sheet.  It’s not a terrible term sheet sheet by any means, though it contains some control-oriented language that is problematic for a number of reasons and hardly “standard and clean.” But what’s the most striking about it is how short it is, and therefore how many material issues it fails to address. And of course YC even states in their article the classic repeat player narrative: “close fast and get back to work.”  The suggestion is that by “simplifying” things, they’ve done you a favor.

Speaking from the perspective of common stockholders, and particularly first-time entrepreneurs who don’t consider their company merely “standard,” short term sheets are a terrible idea. I know from working on dozens of VC deals (including with YC companies) and having visibility into hundreds that founders pay the most attention to term sheets, and then once signed more often “get back to work” and expect lawyers to do their thing. It’s at the term sheet level therefore that you have the most opportunity to ensure alignment of expectations between common stock and preferred, and to “equalize” the experience inequality between the two groups. It’s also before signing, before a “no shop” is in place, and before the startup has started racking up a material legal bill, that there is the most balance and flexibility to get aligned on all material terms, or to walk away if it’s really necessary.

A short term sheet simply punts discussions about everything excluded from that term sheet to the definitive docs, which increases the leverage of the investors, and reduces the leverage of the executive team. Their lawyers will say this or that is “standard.” Your lawyers, if they care enough to actually counsel the company, will have a different perspective on what’s “standard.”  This is why longer term sheets that cover all of the most material issues in VC deal docs, not just a portion of them, serve the interests of the common stock. It’s the best way to avoid a bait and switch.

To make matters even worse for the common stock, it’s become fashionable in some parts of startup ecosystems to suggest that all VCs deals should be closed on a fixed legal fee; as opposed to by time.  Putting aside what the right legal cost of a deal should be, whether it’s billed by time or fixed, the fact is that fixed fees incentivize law firms to rush work and under-advise clients. Simply saying “this is standard” is a fantastic way to get a founder team – who usually have no idea what market norms, or long-term consequences, are – to accept whatever you tell them, and maximize your fixed fee margins. Lawyers working on a fixed fee make more money by simply going with your investors’ perspectives on what’s “standard” and “closing fast so you can get back to work.” For more on this topic, see: Startup Law Pricing: Fixed v. Hourly. 

When the “client” is a general counsel who can clearly detect when lawyers are shirking, the incentives to under-advise aren’t as dangerous. But when the client is a set of inexperienced entrepreneurs who are looking to their counsel for high-stakes strategic guidance, the danger is there and very real; especially if company counsel has dependencies on the money across the table (conflicts of interest). For high-stakes economics and power provisions that will be permanently in place for a long time, the fact that investors are often the ones most keen on getting your lawyers to work on a fixed fee, and also seem to have strong opinions on what specific lawyers you’re using, should raise a few alarm bells for smart founders who understand basic incentives and economics. If your VCs have convinced you to use their preferred lawyers, and to use them on a fixed fee, that fixed fee is – long term – likely to help them far more than it helped you.

Much of the repeat player community in startup ecosystems has weaponized accusations of “over-billing” and “deal killing,” together with obviously biased “standards,” as a clever way – under the guise of “saving fees” – to get common stockholders to muzzle their lawyers; because those lawyers are often the only other people at the table with the experience to see what the repeat players are really doing.  

The best “3D Chess” players in the startup game are masters at creating a public persona of startup / founder “friendliness” – reinforced by market participants dependent on their “pipeline” and therefore eager to amplify the image – while maneuvering subtly in the background to get what they want. You’ll never hear “sign this short template fast, because it makes managing my portfolio easier, and reduces your leverage.” The message will be: “I found a great way to save you some fees.”

I fully expect, and have experienced, the stale, predictable response from the “unicorn or bust” “move fast and get back to work” crowd to be that, as a Partner of a high-end boutique law firm, of course I’m going to argue for more legal work instead of mindlessly signing templates. Software wants to “eat my job” and I’m just afraid. Okay, soylent sippers. If you really have internalized a “billion or bust” approach to building a company, then I can see why the “whatever” approach to legal terms can be optimal. If you’re on a rocket ship, your investors will let you do whatever you want regardless of what the docs say; and if you crash, they don’t matter either. But a lot of entrepreneurs don’t have that binary of an approach to building their companies.

Truth is that, in the grand scheme of things, the portion of a serious law firm’s revenue attributed to drafting VC deal docs is small. Very small. You could drive those fees to zero – and I know a lot of commentators who simply (obviously) hate lawyers would love that – and no one’s job would be “eaten” other than perhaps a paralegal’s.  It’s before a deal and after, on non-routine work, and on serious board-level issues where the above-mentioned misalignment between “one shot” and repeat players becomes abundantly clear, that real lawyers separate themselves from template fillers and box checkers. The clients who engage us know that, and it’s why we have the levels of client satisfaction that we do.  We don’t “kill deals,” because it’s not in the company’s interest for us to do so. But we also don’t let veiled threats or criticisms from misaligned players get in the way of providing real, value-add counsel when it’s warranted.

So while all the people pushing more templates, more standardization, more “move fast and get back to work” think that all Tech/VC law firms are terrified of losing their jobs, many of us are actually grateful that someone out there is filtering our client bases and pipelines for us, for free.

Startup Employee Offer Letters

TL;DR: A few simple principles can help founders avoid big legal landmines in making offers to their employees.

Background Reading:

Hiring an employee is one of the first areas in which I see poorly advised founders really start messing things up from a legal perspective; exposing themselves to liability and errors that can have very long-lasting effects.

Here are a few simple principles to keep in mind as you hire people and paper their employment.

An Employee Offer Letter is NOT the same thing as an “Employment Agreement.”

In the United States, the default for employer-employee relationships is “at will” employment, which means broadly speaking an employer can fire the employee for any reason, even without warning, apart from a narrow set of discriminatory reasons that violate labor laws. This is very different from other countries, which typically have more robust statutory defaults for employees.

When most people speak of an “employment agreement” they are referring to a negotiated document, usually reserved for high-level executives, that provides more robust protections to the employee/executive; including protections around how that executive can be fired, and the consequences of firing her/him. True employment agreements are quite rare in the very early days of startups.

When a startup hires a typical employee, they provide an Offer Letter that states high-level details like their position, compensation, etc., but also makes it clear that the relationship is at will; in other words, they don’t have the protections a high-level executive’s “employment agreement” would often provide. Offer Letters are not Employment Agreements. Know the difference, and that you should start with the assumption that an offer letter is what you need.

Everyone who works for you is not an Employee. Know the difference between a contractor and employee.

I often see founders casually, without really thinking about it, call everyone who does work for them an “employee.” It seems harmless, but in labor law the word “employee” can have very material implications for what you owe them, how you treat their compensation, how easily you can modify their terms or terminate them, etc. Don’t use that word indiscriminately.

Don’t forget IP / Confidentiality, which is not covered in the offer letter (usually).

The conventional structure of startup employee documentation is (i) a simple offer letter, and (ii) a more robust agreement covering confidentiality, intellectual property ownership, and (unless you’re in California or a few other states) a non-compete. This second document is usually called something like a Proprietary Information and Inventions Agreement (PIIA), Confidentiality and Inventions Agreement, or some variant of that. Missing this document can be a huge problem, and in some states fixing it is not as simple as having an employee sign it later. Don’t forget it.

Unlike most legal issues, local state law tends to govern in employment relationships. Docs vary by state.

Most tech startups are incorporated/organized in Delaware, and if they have a national footprint, a lot of their agreements will be governed by Delaware law. With respect to employees, however, that is rarely the case, unless the employee is actually located in Delaware. In employment documents, the location of your employee will often determine the documentation they have to sign, and that means the documentation can vary significantly by state. Work with your lawyers to ensure you don’t use the wrong forms.

Your offer letter might promise equity. But you still need to issue it, which is more complicated.

If you’re promising options or some other form of equity, the offer letter will usually cover that. But you need to understand that the letter is only promising the equity. To actually grant/issue the equity, more steps need to be taken, including a Board Consent and other processes.

Early-stage founders often get in hot water by signing lots of offer letters thinking that’s all they need to do for employee equity purposes, and then waiting a long time (as the value of their stock continues to go up) to be told by lawyers that the equity was never issued. Then they end up (for tax reasons) having to issue the equity at a much higher price than they would’ve if they had done it sooner, and the employees are understandably angry. Promise, then quickly grant. The offer letter is just the first step.