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Guide to Your Equity

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442 pointssamuelcouch113 comments

Your stock options expire 10 years after they were issued or 30 days after you stop working with Clef

This market standard provision in startup employee equity agreements is probably the single biggest obstacle to realizing a gain from employee equity.

What it means is that when you leave your job, if you want to capture any potential upside from your options, you're required to execute them, paying your own money for actual shares. Depending on the amount of equity you have, this may or may not be a meaningful amount of money, but it is in any case a painful decision to have to make.

Companies like Pinterest have done things to address this flaw; they allow employees who no longer work at the firm to retain their vested options without executing them for several years.

Thanks for the feedback! We just realized this document is actually out of date with our legal contracts.

I've opened up a PR with the change here (https://github.com/clef/handbook/pull/56), though it may be 10 years rather than 7, so I'm waiting for confirmation from our CEO before merging :)

EDIT: Our CEO's response was: "this is more complicated than just changing that number, give me some time to write the fully change up." Incoming!

EDIT #2: Updated with the 7 year number and a more depth explanation :) - thanks @brennenHN!

\o/

You should definitely soak up some credit for having that term. :)

And for how it played out! I'm sure that this wasn't what happened but it does occur to me that this pattern makes for a pretty good HN-hack by leveraging HN negativity/cynicism and then swooping in with an "oops - it's actually exactly what everyone thought it should be!". Definitely more net attention this way than would have been if it had just read this way originally.

Wasn't intentional, but I like your thinking :P

I just love how a term that has so much material impact for so many people swung from Not Great to Industry-Leading Excellent . . . from a HN comment, to a PR, and merged . . . in a couple of hours.

I don't think the actual term changed, just the documentation.

Just to say this directly: You guys laying this out transparent to your team (and policies in favor of your team) is an amazing and impressive thing.

Personally i also believe it's a huge marketing/hiring benefit.

Startups live of implicit trust of their employees (imo their core asset)

Larger companies require explicit agreements with them

Very often when startups become larger companies, this trust breaks.

Having those explicit agreements upfront & transparent (before even joining a company) increases this trust a lot.

Kudos for doing so

Thanks Andreas! I know this isn't necessarily a "product," but thoughts on putting it on PH?

i dont make those calls (community & community moderators do)

but from my pov: doesnt really make sense as content on PH

it's more comparable to an really awesome blogpost

HN is by far the better place for it

If I understand the rules correctly, an ISO that is exercised more than 90 days after leaving a job is treated as an NSO, which means that it will be taxed at regular income tax rates instead of having the ability to be taxed at long-term cap gains rate. (This could reduce their value by an additional 15%+.)

That said, it's irrelevant if you exercise and sell an ISO at the same time, because short-term cap gains are taxed as income tax, too.

The real interesting term is having the ability to early exercise your entire stock grant, before it vests and before there is a spread between its strike price and fair market value. (The company would have a repurchase right, to implement the vesting schedule.) That way the cost is very low, and there's no worry of having to exercise in the future when it could be taxed unfavorably, and the clock for long-term capital gains starts early.

It should be noted - an option containing an early exercise attribute is typically rare for common option holders and usually only reserved for management. I.e. most people with a typical amount of options (~5,000) would typically not have this ability.

Less true now. It's $1-3k/employee for the company to deal with it, but a lot of companies include ee, even up to the point where they switch to RSUs.

If there's a repurchase agreement that allows the company to buy back the stock for less than market value (and presumably accompanying transfer limitations) I wonder if the IRS would take the position that it is income only after the repurchase agreement expires at the FMV at that point in time.

The way it works for founders is that you get actual stock, and vesting is implemented with a repurchase right. The IRS considers the stock to be an "asset at risk", meaning that you don't actually realize the value as income until the repurchase right goes away. Because this happens over time, it practically means founder stock is, by default, treated as being earned every month. This is no big deal in the beginning, but if you change the valuation of the company, suddenly each monthly stock grant has a discrepancy between what you paid for it and what it's worth. Therefore, it's income, therefore, you owe taxes on it.

The way to fix this is an 83(b) election, which lets you say, "No, I'm taking the risk of this all up front. I want to pay taxes on it, even though the asset is at risk." In this specific case, it's a no-brainer: there are no taxes today, so of course I'll pay that $0.

If you want to do this with employee options, you have to set up early exercise rights. I think early exercise is done via 83(b) for employees, but I'm not 100% on that. My company isn't big enough that we've had to cross that bridge :)

> If you want to do this with employee options, you have to set up early exercise rights. I think early exercise is done via 83(b) for employees, but I'm not 100% on that.

Yes, if you early exercise ISOs, you would want to file an 83(b) to pay the $0 ordinary income tax burden up front (and get long term capital gains later). I'm not sure if you can file an 83(b) on an NSO.

It sounds like an incredibly complicated process to get to "These options are no longer options, they are stock with basis zero"; Am I correct?

It's a little complicated, but it can be very helpful. The basis isn't zero either, it's what you paid to exercise the option. The tax due at time of exercise is $0 because the fair market value is the same as what you paid (assuming you exercise either at the time of the grant, or at least before the next evaluation of the FMV). The benefit is if/when you sell, if you've held everything for the right period, you can pay long term capital gains tax on the gain, instead of ordinary income like you would if you held onto the option as an option.

Yes, you can file an 83(b) when early exercising NSOs. In fact, some lawyers may advise you to take NSOs over ISOs for the portion of the grant you early exercise.

Is $0 legal? I thought normally you gave the stock 1 billionth of a penny of value and paid your $1 in tax.

It's legal, not because the stock has no value, but because the spread (i.e. the difference) between the strike price of the option (e.g. $0.01/option) and the stock's value (e.g. $0.01/share) is $0. That's the profit, so that's what you pay tax on.

Many people would prefer the NSO since they don't lose out on vested shares upon departure (or get saddled with a massive tax bill). If you have a good chunk of equity, the outcome can be pretty binary: worth something substantial or basically nothing, in which case the slightly higher tax isn't nearly as important as actually getting a piece.

Wouldn't a third alternative be to sell the options to someone who could afford to purchase the shares? Or are they non-transferrable?

They generally aren't transferable, and the market for shares in these kinds of companies ("startups that aren't demonstrably on the trajectory of a Stripe or a Twilio") isn't liquid.

Yes, and there are investors that specialize in these purchases, eg. http://www.esofund.com/ .

Personally I chose to join a famous later stage startup instead of a startup for this very reason. Both offered great compensation and fun roles, but while the later stage startup gives me a lot of RSUs that will soon be liquid the earlier stage startup gives me stock options that expire under these kind of unfavorable terms.

There is a bit of a double standard on stock vesting between founders and early stage employees. Both take about the same amount of risk and the employees frequently give up more salary for less equity. However, while founders owns all vested stock outright the employee stock options most often expire after 30 to 90 days.

The quick stock option expiration is especially problematic since the termination might not be voluntary, and might be a result of changing life circumstances or a company-initiated termination.

The best practice is for founders to vest at the same schedule as employees, so founder shares also vest at the same rate over 4 years. This is recommended by YC and many others, and most startups follow this. Founder shares do not vest outright in most cases.

vesting over 4 years in monthly increments with a year cliff is standard, so I did not make a point about that. Founders normally pre exercise their stock at low cost so they are not subject to expiration of vested stock. Employee stock options are often too expensive for that, and combined with the 30 to 90 day expiration this makes the employee terms undesirable versus the founder terms.

No, founders usually BUY restricted stock, not options. This can be offered to employees, too, as long as the price is reasonable.

At the beginning, a company is usually $100 or so in total, and the founders pony up $20 or so each to buy their shares. The company can buy back the portion of unvested stuff for the balance of the $20 until it vests.

83b election gets you out of tax hell, too.

Talk to your lawyer.

That is correct, but the difference between the instruments is not relevant to my statement. I bought restricted stock when I founded a company, which vested over four years, and have taken options when joining as an employee. Almost chose to do an 83b election on my options using a loan from a startup I joined, in order to improve my tems, but I am happy I did not do so. Considering the risk of failure it is generally advisable to diversify your investments more than that.

Edit: rdl , for the loan from the company to do the 83b election to be a considered a loan by the irs it must have almost full recourse. You will be liable for it and the creditors will ask for the loan amount in case of failure.

Yeah, but in an early company it shouldn't matter as much -- these guys are pre-409A so you could easily argue $500k corp valuation and thus the guy with 1% of the company has $5k of options to exercise. And in a later company you probably don't get 1%. It's probably in the $1k-50k to exercise options in most companies.

A loan which is somehow forgivable for the stock seems like it could solve this; if the stock is worthless, return it instead of the loan. (I thought you can do that? But I guess you can't?)

Wow, this is stupid tax crap, but there seems to be a workaround.

http://www.ecjlaw.com/22505/ecj-viewpoints/taxing-matters/ho...

"Here is how it works: The employer transfers the stock to the employees at no cost, and the employees make the Section 83(b) election to accelerate the taxable event to the date of transfer. That requires the employees to recognize ordinary income in an amount equal to the value of the stock and enables the employer to report an ordinary noncash deduction equal to the same amount.

The employer then finances the employees’ income-tax liability with a nonrecourse loan to the employees (at today’s low interest rates) secured by the restricted stock. Since this doesn’t involve the financing of the employees’ purchase price of the stock, the restricted stock grant would be considered a “transfer” of the stock, thus closing the compensation element of the transaction upon transfer because the Section 83(b) election is made. This avoids the tax uncertainty created by financing the actual stock acquisition with a nonrecourse loan and the requirement of a substantial cash down payment by the employees or, alternatively, a substantial portion of the acquisition note’s being recourse.

Although employees must still pay the ordinary income tax incurred on the date of grant, they have deferred the payment of the tax by means of the employer’s nonrecourse loan. The employer is permitted a noncash deduction in the same amount and at the same time, while the employees are required to include the compensation element of the restricted stock grant in income."

Ianal, but this might work. However, the irs might look at it as tax evasion if the loan was given at the same time as the election.

I would love to buy those lawyers a beer for being such great hackers, even if it's denied. But they said private letter rulings had been given...

It could be worse.

There are startups that offer options that don't even give you the choice to exercise them even after they 'vest'. In this case, exercising can only occur after either a sale or IPO event AND the company has to give its blessing; and the company in question wonders why they have trouble with both hiring and retention.

I know it sucks but read all the legal terms related to your employment, ideally before you join.

How can that be legal?

Federal tax law generally requires that unexercised options expire not later than 90 days after termination as one of the conditions to their keeping ISO status.

Startups by and large have held fast to this requirement.

A few, such as Pinterest, have agreed to extend the 90-day expiration period out for several years. This allows employees who hold vested options having potentially significant value to leave their employment and not have to face the choice of losing such options, on the one hand, or doing an immediate exercise that might trigger a large tax while being left with no near-term ability to liquidate the underlying stock so as to pay that tax (and further facing the risk that the underlying stock might decline in value, leaving them having paid a gratuitous tax on stock that may subsequently have little or no value).

This is an important and very good fix but it does destroy the ISO status of the options and converts them to NQOs.

If the 90-day restriction, therefore, is not built into default plan documents, the company cannot offer ISOs to its employees. It is thus not normally an option for startups to eliminate the restriction wholesale. Any discussion of this issue needs to take this into account because there are various trade-offs in doing it one way or the other, at least one of which may not be good for employees.

Is it possible to have ISOs that convert to NQs if held past the 90-day expiration period, but don't actually expire until several years in the future? Or must they be NQs from the beginning if they have an expiration period more than 90 days past date of termination?

The article now answers this, I believe:

> You have 7 years to exercise your [ISOs] after you stop working at Clef, but by law the options only count as ISOs for 90 days after you stop working. Once those 90 days are up, the options count as non-qualified stock options

https://github.com/clef/handbook/blob/master/Hiring%20Docume...

What is the reason for an expiration so short (30 days) after you leave (or are terminated involuntarily)?

It would be so highly unfair that after joining as an early employee and getting somewhere around 1-2%, if you leave after 4-5 yrs, that all your options expire 30 days after. I understand you can execute them but circumstances or policies may be such that it may not be favorable to do so.

I'm starting to think equity is essentially a sucker's game and you'd be stupid to play it and hope to win the lottery. A good salary and profit-sharing is just way better any day than the hope of overnight striking it rich one fine day.

Taxes are the reason.

"What it means is that when you leave your job, if you want to capture any potential upside from your options, you're required to execute them, paying your own money for actual shares. Depending on the amount of equity you have, this may or may not be a meaningful amount of money, but it is in any case a painful decision to have to make."

Why is that a bad thing? If not exercised, those options disappear, and essentially everyone else is not diluted. If the options remain on the books, it affects everyone else.

Also, from a company perspective, that's a rough go, because earlier shares tend to be worth quite a bit more (whether because of lower strike prices or whether the early employee got a bigger percentage of the company), so you end up with cases of someone who put in a year early on and left holding a significant portion of the company when people who stick it out for longer get much less.

Of course, in any case, the company can always issue more shared to dilute out the early shareholders who left, while dishing out the new shares to everyone who is still employed, but then you're right back to square one.

There are a bunch of reasons why it's a bad thing, and most of them are compelling to me --- in principle, you worked for 3-4 years to earn equity, not the opportunity to buy equity --- but there's a big reason that I think is dispositive.

When a company sells, it negotiates with its buyer for a long time to come up with a price and terms for the deal. Former employee stockholders are iced out of that negotiation. The buyer and sellers have levers to pull that improve the outcome for themselves at the expense of former employees; for instance, the terms of the deal can include retention bonuses paid to employees, and in fact are sometimes dominated by those bonuses. Nobody needs to decide to be evil to make something like this happen! It's rational for the buyer to want to extend additional benefits to keep employees, and management is numbered among those employees.

I've had friends who paid significant amounts of money for their stock only to have it end up worth 0 in subsequent high-8-figure sales.

> if you want to capture any potential upside from your options, you're required to execute them, paying your own money for actual shares.

If you want to capture upside, then you must believe that there is upside, so then surely you can offset the cost of buying the options into your expected return?

It's a question of liquidity: If you stand to make $1m but have to put up $200k right now, that only works if you have a liquid $200k right now, and are willing to risk it on a single company stock (as opposed to say a down-payment on a house).

I agree with this, but it is worse than you make it out to be. If the options have increased in paper value since they were issued, which is to say the current strike price of newly issued options is higher than your strike price. You MUST pay US income tax on this "gain" because, according to the IRS, you could turn around and sell your stock at the current price and get cash for it.

The craziness is that you cannot actually do that. But you pay the tax anyway, and if they company goes away, or has an exit where the common stock gets no value, you can record the "loss" $3,000 a year until you have used it up.

So worst case is your out both the exercise money and the tax money. Wham wham!

This is typically where the 83b elections come in, right?

Also, has anyone ever had trouble with the "speculatively execute one option buy a share to get access to the books for a sanity check" thing? That's normal practice, right?

I would absolutely do this if I find myself in a position where I am accepting ISOs again. Not doing so left me completely out of the loop in regards to company direction, how much the owners were paying themselves in dividends, or potential buyout options.

In my experience common stock (i.e. what your options buy you) has no "information rights", so the company does not have to disclose financials to you. Additionally, even if you were offered the chance to buy preferred shares (what investors buy in a Series A, B, etc.), which ordinarily do carry information rights, there is usually a provision that prevents stockholders with paltry participation in those rounds (e.g. buying a single share) from enjoying information rights.

It's an extremely risky situation to be an employee stockholder. You are at the mercy of the founders, board, and investors. Usually founders also hold common stock, so that is somewhat reassuring, since they're in the same boat as employees from that perspective. However--and not saying this happens often--there is nothing preventing founders from being given the option, say in an acquisition or financing round, to cash out while employees are stuck without liquidity.

How do you lose the tax money? As you said: you can record the "loss" $3,000 a year until you have used it

note: I'm not a tax professional and can't give tax advice. My experience with AMT is you can only get back the value of the stock that became worthless, not the money you paid in taxes when you exercised it.

This is my major rub with ISO's. Their sentence sums up the problem perfectly: "You’ll still be able to buy it for $1 (and then sell it immediately for a profit of $19)."

How am I supposed to sell a stock immediately if I have no market to sell it on because the company is private?

In my opinion, ISO's drastically favor the employer. If I am unhappy and wish to leave, but have vested two years of options, I am forced to either a) throw them away after 30 days or b) purchase them and take on a potentially enormous tax burden unless I do actually have the ability to sell them immediately.

Additionally, by waiting to exercise at a later date I further push back the amount of time it takes to qualify for long term capital gains when selling the remaining portion of the stock.

I was in the exact situation I describe about three years ago when I was very unhappy and wished to look for something new. I had vested an extremely generous ISO grant that, should I have exercised it, would have bankrupted me from the tax bill. My stock was worth 100x what my strike price was, so in essence, I was the "victim" of the company being extremely successful. My way out of this problem was simply luck: we got bought four months after this personal crisis started.

I also found myself feeling like a second class citizen as time wore on. I had been a first employee and helped build the company into what it was, and I felt involved and informed with most everything going on. As time wore on, we became successful and grew substantially and I found myself in a situation where I was becoming simply a senior member of the engineering team. I was certainly not an owner, despite what my time, acceptance of risk, and vested options would imply after four years of hard work.

If companies really believed in the value of an ISO they would put their money where their mouth is and have a stock purchase program that helps alleviate the tax burden over time. It's that, or allow option holders to keep their options for many years after employment terminates. As an owner, what do you want -- option holders that happily stick around even when they could leave or employees who feel they are forced to stay regardless of what happens?

A recent trend (that employees should push for) are yearly (or more often) buyback events, where the current major investors and new Series X investors offer to liquidate current/former employee positions.

Agreed. It's an act of good faith that brings the owner/option holder arrangement more into balance as a company's situation changes. In general I am in favor of any action that attempts to accomplish this.

Quick summary guide to what you want your option equity grant to be like:

1. Must have an 83(b) election process, and give a bonus to cover pre-exercise cost OR:

2. No expiry after leaving the company, instead should just convert to NSOs AND

3. If possible, options should expire after 15-20 years with the longer time horizons to IPO today compared to 7 years ago. Facebook for example took 8 years from founding to IPO. Even if you stay employed at facebook for the entire time, you could have lost all of your stock for example.

4. Vesting cliffs should be no longer than 1 year.

If you are unwilling or incapable to pre-exercise your startup stock, then equivalent RSU grants are superior to stock option grants. Even most $1bb startup employees have a very hard time finding people to buy their stock outside of company secondaries when the company is private.

----

What you give up at a startup as a sr. engineer vs bigco:

1. Saleable within 1 year +$100k/yr equity grants. These equity grants can then be used in other investments, such as a house down payment or otherwise. Give them a bonus of %7 annual compounded interest.

2. Higher salaries

3. Bonuses

4. Some benefits which may have high amount of financial benefits for your situation, such as paid parental leave.

5. Hours worked.

Make sure that the startup offer can beat a big co offer if a +$100mm sale event happens by a good margin. If your startup offer cannot beat that, then working at that startup will have a near certain chance of having a big financial downside compared to working at bigco. Working at bigco is the index fund of tech work, make sure your startup 'investment' at least has a chance of beating the index fund.

> We have not undergone a 409A valuation to determine the current strike price of Clef stock.

Isn't a 409A valuation required every 6-12 months by the IRS?

EDIT:

"Section 409A requires the value of stock options be determined “by the reasonable application of a reasonable valuation method” with two caveats: 1) the grant price must reflect material information, often referred to as a value creation event (i.e. the price paid in a recent financing); and 2), the calculation of value must not be more than 12 months old. In practice, private companies pursue 409A appraisals from independent qualified valuation firms either immediately after completion of a financing or other significant financial transaction (e.g. merger or acquisition), or, six to nine months of elapsed time since the prior appraisal, whichever comes sooner (more mature companies tend to pursue appraisals more frequently). The receipt of such an appraisal should provide a safe harbor to employees with regard to a potential tax liability as long as your company is less than 10 years old, you don’t have a liquidity event within 12 months after the option grant or you don’t have put or call rights on your company’s stock."

https://blog.wealthfront.com/409a/

Later they mention "(We are currently in the process of getting our 409A Valuation)"

This might be fine if their compensation plan was formed in 2015.

You should include a Standard Offer Letter example showing employees what their stock/etc. will be worth under various exit assumptions. Showing/including the employee handbook at the same time is great, too.

(I'd like to make this a standard thing; would be happy to help with this. Would need to find a lawyer willing to contribute time. I'd love a Standard Human Readable Offer Letter Builder.)

Offer letter should be super standard. The offer letter generated by Zenefits is a single page...

Which is insufficient to value the offer.

I want there to be an offer letter plus other materials which explain it. It's meaningless to say something like "12000 shares of stock, vesting over 4 years." That may be the legally binding part, but there should be an appendix or model which shows what that actually means.

The problem with making that a separate unsigned/etc. document is it isn't legally binding in the same way an offer letter is.

There's additionally the insanity around "stock options must be approved by the board at the next meeting after you're hired", which could be a quarter. That seems stupid. There should be some cleaner way to handle that.

Oh yeah, usually i just send a spreadsheet. Even the stock options aren't legally binding usually... they still get approved by the board after the hire is made. It is not possible to pre-approve them, but you can do it but UWC (unanimous written consent) without holding a full board meeting. That's what we do.

They can do better - they explicitly list in another part of the handbook what every employee receives (https://github.com/clef/handbook/blob/master/Employment%20Po...):

> Every employee will be offered 41,963 Clef stock options (~.9% of outstanding shares, including the option pool these are drawn from). As mentioned above, they can also choose to reduce their salary by $5k/year in exchange for 4,663 more options (totalling ~1% of outstanding shares).

This is a genuinely impressive commitment to transparency.

Looks interesting.

I'm not a lawyer, but:

1) I'd consider Restricted Stock/Founders Stock instead of options for pre-A employees.

2) Early exercise should be an option; I'd personally not work at a pre-$50mm val company without EE as an option.

3) Whoa you survived a long time before getting a 409A.

4) Should let your employees exercise options for years after leaving.

100% agree.

I'm surprised that there's no mention of an 83(b) election. I'm not a tax expert (hah!) and you might be nervous about giving anything that could be construed as tax advice, but I imagine you could safely say something like:

"While we cannot give tax advice, we strongly suggest that you consider making an 83(b) election when you are initially granted employee stock options. If you choose to make an 83(b) election, you may need to do so within 30 days of joining."

As I understand it, this can be a Big Deal (tm).

I believe 83(b) only applies to restricted stock grants, not ISOs, but I am not an accountant.

I have worked for two startups early enough to take advantage of the 83(b) election. In both cases, the companies assisted me with the election, providing all the paperwork, etc.

83(b) election still applies to any early exercise of stock options subject to vesting. An important detail that is often overlooked.

On re-reading it, I think you're right. Still might be worth mentioning.

No, they apply to ISOs as well. I was able to benefit from this. I didn't do it immediately, but within a year or so of my start date, and at that point my paper gain was small enough (~15k) to not quite cross the AMT threshold.

Same thoughts there. For early employers, it is almost always beneficial to exercise early at a reasonable low strike price. (oh sure, please always consult tax experts).

Just found out that they changed the option expiration from 30 days to 7 years? That suddenly makes 83(b) election not as attractive.

This is a game changer, especially for people who are new/inexperienced in the Startup Compensation Lotto.

I wish more companies would approach this subject so transparently!

Also makes the feedback / change process transparent! As long as all employees use git.

When stocks lack dividend payment, can someone explain their intrinsic value apart from market speculation & https://en.wikipedia.org/wiki/Greater_fool_theory ?

They mean that you own a specific fraction of the company (at least until the stock gets diluted). If the company is worth $X, and you own Y% of it, then your stock is worth $XY/100.

If I own 5% of a laundromat that gives me 5% of it's profits each quarter, then I have money coming in. What's the point of owning 5% of a company that never pays shareholders a dime? It seems a bit like owning a piece of property on the moon.

It's speculative. You're really just hoping that one day, your company will IPO, and the initial stock price will be (much) higher than the price of your options.

Or, if the company starts paying dividends, you could exercise your options and start receiving dividends, but I think that's unlikely knowing the sector we're in. :)

But why would someone else buy a stock.. if their only motivation would be that the price increases .. and they sell to someone who.. (GOTO start of post). Is this not the bigger fool theory?

The company itself is worth something. It's worth whatever it's worth to someone trying to buy it, for example. As a general guide, it's worth some multiple of its annual profit, with the multiple depending on how fast it's growing and how much longer it's expected to continue growing.

With the idea that with 51%, you can control the company's choices, right?

Presumably at some point in the future, the company will make money and pay dividends. The 409A valuation is supposed to be an approximation of the valuation based on the likelihood of future dividends (I believe using Generally Accepted Accounting Principles). For a startup, this valuations is almost always a lot less than the top-line valuation used in the press / Series A investments.

Well, the company can still be worth something when it's sold to someone else. That's not solely speculation, but it's not far from it.

I understand the popularity of non-dividend-bearing stock, but I don't like it.

At the end of the day, it's belief by someone in future dividends or purchase by another entity. If you don't want the latter to mean 'speculation', then take it to mean 'wholesale acquisition by another company.' That makes stock valuable too.

If I weren't on my phone I might open a pull request for this, but in this paragraph you suddenly use the term option to mean choice, I'd use choice where appropriate to avoid confusion:

  This means that while you have more options regarding your equity, you will lose a significant amount of your options' value if you wait. In weighing your different options, you should consult a tax attorney to help decide what path makes the most sense for you.

"The lower the exercise price for Common Stock, the more money your options will earn you, so it’s in our best interest to make this price really low." - technically, while it's in the employee's interest to have the price be as low as possible, isn't it in the company's interest to have the price be as close to the 409A valuation as possible?

409A valuations apply to Common Stock, which lack the preferences associated with Preferred Stock (usually sold to investors). As a result, Common Stock is typically priced at a significant discount. It's most certainly in an early stage startup's best interest to keep the Common Stock price low, because it offers more flexibility when incentivizing team members.

"So if a share of Clef stock is worth $1 today and we grow so it’s worth $20 in a few years, you’ll still be able to buy it for $1 (and then sell it immediately for a profit of $19)."

Use more realistic numbers. The likelihood of your company going to $20 a share, and with the ability of the share holder to "sell it immediately" is very unlikely.

I commend you for sharing this. A couple issues for you to consider:

Share price isn't always set in that clean a manner, as you'll learn when you fundraise. It's nice when your math works out like this: "if Clef is worth $20m and we raise $5m, we are now worth $25m. If you owned 5% of $20m before, you now own 4% of $25m (we sold 20% of the company, or, said differently, diluted you by 20%). The 5% stake was worth $1m before the fundraise and the 4% stake is now worth $1m." but often you end up with a bit more complexity. Beware simple examples can still set expectations. Converting notes with discounts is one example of this. Preferred and common are not treated the same way, and it is unlikely you will escape selling preferred shares to your next investor.

Early exercise would actually be far more tax advantageous to your employees. You can do this "cashless" as an even greater benefit.

We have not undergone a 409A valuation to determine the current strike price of Clef stock.

So basically, what you're saying, is that unless you're guaranteed to strike it rich, it's better to ask for more salary, more vacation time or other tangibles? Greeeeeat.

I would prefer profit sharing to stock options/equity or actual ownership that means something, such as in a co-operative. It's great they want to make sure they're building a company for the future, but cash now is always better and even better is if it's guaranteed cash in the future too (as with profit sharing where you can actually see the increase or with performance bonuses where you can actually see if they're shrinking or growing).

The section about granting ISOs to avoid a tax burden on employees is downright dishonest. Support 83(b) elections or outright bonus the employee the strike and tax (I've personally seen this happen before). AMT is a motherfucker.

It's interesting that they offer people to take 0.1% more equity for a 5k reduction in salary.

https://github.com/clef/handbook/blob/master/Employment%20Po...

With a 6 year vesting schedule a new employee is 'buying' 0.1% worth of shares for 30k in salary. A 30MM valuation, or 5X the 6MM cap on the convertible note.

I would like to focus on those comments that are questioning if stocks are just a way to trick employees in getting a lower salary. I believe that regardless of the lifestyle you want to have, stocks have the potential to make you really wealthy, way more than collecting salaries.

In startups a good salary will give you an affordable and stable life, sometimes short-term security (because a higher salary like 200k/yr could only last a couple of years until the startup cease to exist). On the other side stocks are the best investment to drastically improve your finances. To put it in layman's terms, it usually take many years, sometimes a lifetime, to buy long-term security, a nice house and fast cars just by collecting a salary month by month. Selling earned stocks can do all of that in 2/4 years. If it doesn't, then move on.

It's a bet and a different type of gambling, therefore should be treated as such. Now, if you can or cannot afford to gamble it's a different story. In my experience people with families understandably lower their risks by preferring a higher salary, while those who don't have any wife/kids prefer stocks.

Regardless of that, this doesn't change the fact that stocks have the potential of being worth 10-20-30-N times a yearly salary, and sometimes that qualifies them as a good bet to some people (and certainly it does for founders and investors).

Sorry if I'm missing something but what's preventing the employer from creating stocks with 100000x liquidation preference for themselves after they have given the employees their equity? That would mean the employees stocks would be worth nothing at a sale? See also hellbanners comment about dividends. What is the actual value of having the stock?

Thank you for posting this! It's a brave move and I think other companies should do the same.

One question for you: do you have any restrictions on the sale of your stock by employees before the stock is liquid? Specifically, do you have any provisions that say the stock can't be sold without board approval before shares are publicly issued on an exchange? I've had friends burned by this in the past....they throw down 5-6 figures to exercise their options, pay the taxes, etc after two years with the company, then find that they can't legally sell the shares without board approval, which basically means they can't sell until the stock is publicly traded. It's been particularly painful in one friend's case because he tied up virtually all his liquidity for what he thought was a very temporary basis in exercising the options, and now has no clear timeline to monetization (company's last round was B, no IPO in sight).

That's a pretty solid summary even if you don't work for Clef. Very helpful document.

A very good example to set for other companies. I'd love more "easy terms" github repos with a "if in doubt consult a lawyer" clause. It communicates that the company is interested in making sure that employees understand their benefits well (I often get the impression many companies don't)

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The "golden handcuffs" are interesting. Are there any companies that ofer you a credit at X% to buy your options when you leave? Say you leave and own 50k options at aprice of 1$ and they are valued at 20$ now. Currently you have to pony up the 50k or pay taxes after 90 days. Since the employer also has to pay taxes it would make sense for them to offer a deal where you get "just the profits -X" so to speak.

Are there any money lenders specialized in this? It's basically a "sure thing" as long as you have the big lump sum up front.

> This is a little bit of a roundabout way to give you ownership of Clef, but the reason we give options instead of straight stock is that it keeps you from being taxed on the stock until you actually use it. If we gave you $10,000 worth of Clef stock today, you would have to pay thousands of dollars in taxes this year.

Maybe I misunderstand, but this seems somewhat dishonest to me. Giving out options instead of shares does not help the employee or or "keep you from being taxed." Instead, it's a punishment for the company not growing. If the value of the company does not increase in value before the vest date, the options will be worth nothing, but shares would still have value.

Not at all. If the company doesn't grow, there is no way any of the common stock shareholders get a noticeable payout due to liquidation preferences. Whether their ownership is in the form of options or stock does not matter.

This is interesting, specifically the outstanding convertible notes. If the six year vesting is meant to communicate their company priorities, the over 30% (minimum, based on Series A) of the company owned by investors does too.

> $175,000 was raised on notes with a cap of $5m > > $1,683,555 was raised on notes with a cap of $6m

For the first set of notes, that is a minimum of 3.5% of the company. For the second set of notes, that is a minimum of 28% of the company.

So for a pre-Series A company, you already have nearly a third of the company owned by investors. That percentage is only going to go higher in the future. If I'm an employee, I'd better hope my shares won't be diluted 30% in all future rounds.

Isn't it sale date 2 years from grant, not exercise date 2 years from grant, that matters for ISO vs NSO treatment? "Instead, if the employee holds the shares for two years after grant and one year after exercise, the employee only pays capital gains tax on the ultimate difference between the exercise and sale price. If these conditions are not met, then the options are taxed like a non-qualified option" from https://www.nceo.org/articles/stock-options-alternative-mini...

I'm the only one who read 50 hours at the office? Poor Americans :)

Still the most powerful and richest country in the world.

Wages are typically commensurate though. I'd rather be in the office for 10 more hours than you if I can make almost triple (depending on where you live, the UK for example has shockingly low wages for tech workers).

That's pretty insane actually (although common) - would immediately disqualify them from consideration for me.

where does it say that?

https://github.com/clef/handbook/blob/master/Employment%20Po...

"we expect full-time employees to be at the Clef office between 45 and 50 hours a week""

This is the clearest document about how stock options work that I've seen yet. That alone is commendable, even if it weren't for other commendable things like listing the denominator on what fraction of the company you own and otherwise avoiding the usual employee-hostile temptations here.

Unless I missed it somewhere it would be interesting to learn more about how and when you can exercise and sell your shares. For example is it even possible to sell a portion when the company is private? Back to the company or to VCs? What if the company never goes public?

Could you go into greater detail about what taxes does the company pays when an NSO is exercised in a year when a person is no longer employed? Is it just the employer's part of medicare and social security (7.5% up to 117000 as of 2014?) or is it something else?

This is the best thing since sliced bread. Resolved a lot of uncertainties to me (an engineer) about how this stuff works.

Guide to your equity: you should assume your equity is worthless just out of the nature of startup risk.

Even if it ends up being worth something, you should assume that your employer will do everything they legally can to dilute or otherwise devalue your financial reward from equity.

Getting employee equity will always be, at best, a few crumbs from the loaf you're helping to build.

It's now possible to have a choice between a company whose benefits result in only crumbs, and a company that offers slices.

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