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Open guide to equity compensation

Open guide to equity compensation

292 comments

·April 13, 2025

cj

As our 30 person startup has grown, I made a conscious decision to stop pitching stock options as a primary component of compensation.

Which means the job offer still includes stock options, but during the job offer call we don’t talk up the future value of the stock options. We don’t create any expectation that the options will be worth anything.

Upside from a founder perspective is we end up giving away less equity than we otherwise might. Downside from a founder perspective is you need up increase cash compensation to close the gap in some cases, where you might otherwise talk up the value of options.

Main upside for the employee is they don’t need to worry too much about stock options intricacies because they don’t view them as a primary aspect of their compensation.

In my experience, almost everyone prefers cash over startup stock options. And from an employee perspective, it’s almost always the right decision to place very little value ($0) on the stock option component of your offer. The vast majority of cases stock options end up worthless.

__turbobrew__

Even if the company has a successful exit lots of times the founders have different stock class than employees which allows them to cook the books in creative ways where employee stocks are devalued without affecting founder stocks.

I personally went through a successful exit of a company where I was one of the early engineers and was privy to orchestrating the sale (working with potential buyers and consultants) and saw this happen.

I now am granted stocks which are traded on the NYSE so nobody can cook the books without commiting securities fraud.

pc86

Somewhere along the line "privately-owned company" morphed into "do what in any regulated industry would be considered fraud."

Multiple classes of stock for non-investors in a pre-IPO/private company should be illegal because there's no visibility or transparency. The other side of the table has no legal right to audits or reviewing the books so the opportunity for fraud is huge. Maybe have an out if you have verified third-party audits and cooking the books like you mention (which happens all the time) carries the same fraud penalties as if you did it for a public company.

chrisfosterelli

Not every company is a unicorn. For bootstrapped companies that might never sell, multiple classes of stock can be extremely useful for a variety of legitimate accounting and dividend purposes. One of the local law firm's company setup packages uses a de facto _six_ share classes.

I agree with your concerns re. transparency but I don't think eliminating share classes would fix that.

grepfru_it

This is highly country dependent, but in America for example, if this is not presented in your employment contract then it is not something your employer needs to do.

However, if your employer is a public organization then all of this information needs to be made available to shareholders. While you may not have access to this information, it is not secret and can be shared by any of the shareholders. Due to this, there is an implicit requirement to reduce risk and “cooking the books” while allowed is generally seen as risky since shareholders may run for the hills. In a smaller, privately run company there are no shareholders to run for the hills. Just a bunch of employees who hold paper IOUs. In order to get that audit protection, the employee would need to negotiate that into their employment agreement!

hiatus

> The other side of the table has no legal right to audits or reviewing the books so the opportunity for fraud is huge.

Are private companies allowed to share some information with a subset of their investors and not others?

tom_m

Well, they don't always get away with it. Depends on who gets pissed off.

duped

I think you can nix the qualifiers - multiple classes of stock have inherent problems and should probably never be legal

babyshake

One other trick I learned about and should warn others about - getting an offer for shares (an employee level %) where there is in fact no options pool and existing shares will be diluted for every new employee who joins the team. I got such an offer, and not only was this information not given to me until I asked about any events aside from funding rounds that would be dilutive, but it was presented as standard operating procedure.

gruez

>getting an offer for shares (an employee level %) where there is in fact no options pool and existing shares will be diluted for every new employee who joins the team

How's this different than if an option pool exists? The more people have options, the further the pie will be split up. Having an option pool or not doesn't change this.

sandGorgon

there is a proxy to check this - investor quality. Every high quality investor - including YC - forces an options pool. The post-money SAFE created by YC accounts for an options pool ("The Post-Money Valuation Cap is post the Options and option pool existing prior to the Equity Financing").

high quality investors will in most cases, decline a fundraise if there is no options pool - since it signals that the founders are not serious about the most valuable asset of any startup.

The people.

tom_m

I've found getting info around stock options at startups is often really hard. It's not very transparent. For example, the total diluted shares isn't shared or sometimes even the current valuation isn't shared. LoL good luck with ever seeing a cap table. Often times that makes it impossible to even determine their value.

There can be value here for sure, but everyone dreams big, never asks questions, and never tells. My other favorite in this industry is "stealth mode" lol.

carimura

"Cooking the books" could mean many things but most people would interpret this as fraud. There are many exit scenarios that aren't fraud but rather stacks of preferential stock that get paid before common, who usually get paid last.

What happened in your exit scenario?

matt-p

There's also just the case that a buyer is happy buying say 88% of the company and having 12% (usually non-voting) shares lie with employees/former employees. Stock options are only really, truly worth anything if they IPO.

awesome_dude

My read is that the poster felt that the accounting practices, which were likely legal and commonplace, violated implied contractual obligations.

__turbobrew__

See my comment further down. Im not going to go into any more details than that as the details of the sale are not public.

SpicyLemonZest

"Fraud" is a strong word, and there's nothing inherently wrong with having multiple share classes. But I really feel that preferred stock as implemented by most early stage startups is an intentional attempt to deceive employees. There's a lot of founders out there telling early engineers they're getting "0.5%" when they know full well that a $1B acquisition down the line is not going to put 5 million dollars in the engineer's pocket.

guappa

It is fraud to take advantage of the fact that your employees don't realise their stocks are not the same kind of stock that the VC and the founders have.

mancerayder

Can you share at a high level what you meant by cooking in the context of the exit?

hibikir

When the founders still control the board, in practice the buying company understands that what makes the acquisition work is that said founders end up happy, and that the outcomes for your typical employee can be sacrificed to the edge of what the law allows.

Maybe there's management carve-outs. Maybe the total value of the acquisition is lower, but as part of the negotiation, there are great transaction bonuses, or retention bonuses. The investors with preferred shares still get their liquidation preferences, but the common stock is worth a pittance. Maybe instead of an acquisition, some of this is turned into an asset sale, or there's some considerations for founders that involve very friendly rollover equity. Maybe the founders add a new kind of stock, or create a new legal entity as part of the acquisition that does... "interesting" things. An inventive legal team cannot do miracles, can make sure that the employees feel robbed either way.

The acquirer, the founders and the VCs with the biggest share will get what they want, and come up with something neither will challenge. So it can be down to just the workers to pool together and decide to sue for violation of fiduciary duty, which might not be fast or easy to prove. You aren't in the room where it happens, but everyone else is.

gen220

Dilution and liquidation preference.

Dilution is sort of a necessary evil that comes with raising new rounds of capital. I understand how >1x liquidation preference is legal, but it seems incredibly unethical, especially since it's never communicated to common stockholders.

IMO, if you feel the need to hide your cap table from your employees, it's probably unethical. Yes, indeed, most cap tables are unethical.

fragmede

dilution

Gamemaster1379

I got forced into working for some garbage startup at a job early in my career. The CEO was absolutely psychotic and never put much effort into hiding his motives.

The guy gave me a "Pre selection" letter (bokded at the top that it was "NOT A LEGAL DOCUMENT") that I was selected to receive 1,000,000 shares, vested at 250k a year (no one year cliff into monthly). 1,000,000 of how many? Didn't say. Percentage? Nope. Was it 25% 3% .00003% Who knows!

I eventually was forced out after him verbally abusing me, making unsubstantiated accusations about how I spoke to other employees, and doing things like asking me to clock out and continue to talk about work.

I received two death threats after I quit. And, seven years later, I get a threatening letter falsely accusing me of defaming the company under random online accounts. After rejecting the allegations, I got a "settlement letter" that demands I forfeit all obligations, and can never talk about the employer again. It also explicitly stated I'd get $0 and that they "wouldn't appear at my place of residence" as my benefits.

Last I saw the SEC audited them and said they had no revenue and no products to commercialize.

They raised $6m on fundraising sites selling SAFEs, but had $800k in assets and $6m in debt. Oh, the most interesting part is the owner had the company paying his other computer repair business $5k a month for IT services.

It really reenforced for me how meaningless the whole process. Working for that company was a lifetime mistake.

fragmede

Damn, that really sucks. It really is the luck of the draw. I started at a company that just paid me an hourly rate with no promises of stock options but I could just as easily have been dragged into some kind of mess like you experienced.

szundi

[dead]

JumpCrisscross

> the founders have different stock class than employees

This is super uncommon.

> stocks which are traded on the NYSE so nobody can cook the books without commiting securities fraud

The exact same fraud rules apply to private and public stock.

iancmceachern

I've personally seen it happen multiple times from inside, it happens all the time.

It happened in the largest medtech acquisition in history (at the time) its Public knowledge.

grandempire

I often had startups offer me a number of shares with no explanation for the percentage ownership or the number of total shares.

I said I have to value them at zero without more information and they would act all offended when I asked for more (happened at least 3 times).

This suggests to me that founders either don’t understand the mechanics themselves or are preying on lack of financial understanding.

dymk

It’s the latter.

grandempire

Ignorance is a big problem too. One time I had someone offended when I asked if their insurance plan qualified as a high deductible - they didn’t know it was a legal classification and thought I was accusing it of being expensive.

I’m not anti-startup but the VC backed startup culture of the last 10 years or so has been pretty souring.

avn2109

It's kinda both sometimes haha

Swizec

> The vast majority of cases stock options end up worthless

My fav manager had a great way of phrasing this: "There are more ways for your options to be worthless than to make you rich"

But I also personally know plenty of people who made off great with their startup equity. They're def not worthless.

Ultimately I think you should never take an uncomfortable pay-cut to join a company and you should maximize your stock compensation on top of that. Don't forget other types of equity – brand, exposure to good problems, network.

crote

I think the main thing to remember is that you should assume they are worthless.

There's probably something like a 99% chance they are worthless, a 0.9% chance they are worth a decent holiday, a 0.09% chance it'll let you retire early, and a 0.01% it'll make you somewhat rich. Worst of all, unless you're the CxO you have very little control over the outcome.

Equity is a nice bonus, but you might just as well treat it like the company giving you a lottery ticket for Christmas. Nobody is going to take a significant pay cut or work 80 hours a week for a lottery ticket, so don't do it solely for the stock options either.

sharkweek

I’m 0 for 3 on startup equity being worth anything and have since left the industry.

One of the startups I did some time at was as close to a sure thing as one can hope for (unicorn valuation at one point) but it still went to zero in a very public flame out. It’s still impossible not to get imaginative about what could have been as I was a very early employee… such is life.

The most lucrative stretch of my career was working for a big company that paid good base salaries.

aetherson

I've worked at 8 companies, 3 have resulted in value from equity (all granted pre-IPO), all of them in certainly much larger than "a decent holiday" level.

I think people have updated to be much too negative on the prospect of equity paying out. It's obviously much better than 1%, at least if you work at anything other than extremely early-stage companies.

randerson

> you should assume they are worthless.

I had this mindset at a startup and decided not to risk any of my money exercising my stock options. They eventually expired. Years later the company IPO'd and I would have made a lot of money had I exercised.

Waiting for more certainty before exercising means the fair market value will likely be higher then and you'll have to pay AMT.

I now approach a job with the mindset that stock options are probably worthless, but I'll risk what I can afford to by exercising as soon as I can.

hibikir

It really depends of the stage of the startup. I recall reading someone doing analysis on this (unfortunately I don't have a link) showing that joining a company that isnt public yet, but is already large-ish and showing some real product-market fit gets people better payouts. Yes, employees 1-40 of a future unicorn will to great (if they could afford to buy the shares, and AMT doesn't kill them which is another story), but it's relatively safe to get into a company that hasn't IPO'd yet.

Imagine say, that you joined Stripe in 2014. By then, probably 500-1000 employees and a a real name on the industry, yet private. It's perfectly reasonable to not consider the stock they might have offered at that time as straight out money, like you'd have treated Google RSUs. But discounting the shares to zero, or just "a nice bonus" is also silly. I bet anyone that got a year or two of stock in that era is well into the retire-early/somewhat rich cadre, and that wasn't all much of a risk.

awesome_dude

> But I also personally know plenty of people who made off great with their startup equity. They're def not worthless.

I personally view Stock Options in the same way as lottery tickets - sure they might pay out big sometimes, and people do win lotteries, but, for the most part, they're going to be losers.

There might be argument about the difference in how often stock options lose compared to lottery tickets, but that's missing the point.

ants_everywhere

The main difference is that people often think they share a fate as a startup. They all have the same lottery tickets (in varying amounts) that pay out under the same conditions. After all, that's how managers often motivate the early employees.

But since there are different classes of lottery tickets, the payouts can change arbitrarily at the last minute depending on the specifics of the deals.

So even after accounting for the fact that most lottery tickets don't pay out, you need to account for the fact that some within the same startup might pay out while yours don't. And there's no perfect way of knowing ahead of time.

fragmede

Sorta. You could definitely go in on something worthless that never gets any traction and end up with less than zero, as in, you owe money after the experience. But for every Stripe or Airbnb there's 100 more lesser known names that still pay out, not in the millions, but a couple hundred thousand dollars range, which is still enough to change most people's situation.

Definitely look at them as worthless untill they're worth something, but the untold secret is the secondary and private market. SpaceX employees have gone that route and some are quite rich despite there not being an IPO. Again, the failure mode to be aware of is you could end up in debt and owe money which is worse than if you'd never played.

candiddevmike

Pre/post pandemic startup equity seem to have wildly different outcomes

babl-yc

So would you trade your founder equity for a fixed salary? My guess is probably not.

Equity is an extremely important factor for many candidates, especially more senior ones and executives.

I would not pitch it as future value, and instead pitch as % of company. If it's a minuscule amount that doesn't move the needle in offer conversations, than perhaps you are not offering enough, or you're identifying candidates who value more predictable income than investment in the company.

paxys

Exactly. If I'm joining a 30 person startup it's not because of the size of the paycheck. Any larger company will obvioulsy be able to easily beat the offer. I want a significant amount of equity. I want to see the cap table. I want to see details about funding rounds, finances, available runway. I want to see MRR/ARR, recently closed deals. If founders dance around these questions and say "equity is not imporant, see how much we are paying you" then I'm walking out the door.

cyanydeez

Reading through the thread, the point is the startups arn't providing transparent accounts of what the equity is and how it can be diluted and reduced over the life time and sale of the company. That's all the debate.

Many people have seen those options become worthless because of legalistic maneuvers and violate what's said in the initial options.

So this tangent isn't really clarifying anything. Some people would simply want larger salaries and options be valued as 0$ for evaluating compensation because how easy Capitalists have made it to screw over classes of options/share holders.

parpfish

the founder has so much more control over the direction of the company and what an exit looks like that it makes sense for them to want equity.

As an IC, there’s little I can do to affect the company valuation because I’m just executing the CEOs vision. And there’s nothing I can do to affect their decisions about potential exits.

scarface_74

Yes I would trade founder equity for an increased fixed salary. Statistically, equity is going to be worthless.

Aurornis

> In my experience, almost everyone prefers cash over startup stock options.

My experience has been a little different. We had a lot of people demanding both very high cash comp and then demanding very high equity packages on top.

Giving people a sliding scale option did put some of the control back in their hands, but it also produced an analysis paralysis for some where they couldn’t decide what to pick.

> And from an employee perspective, it’s almost always the right decision to place very little value ($0) on the stock option component of your offer. The vast majority of cases stock options end up worthless.

Much of this is due to startups failing. Every random “startup” trying to pay people with options because the founders have no hope of success inflates this statistic.

However another driver of this statistic is the extremely short exercise window upon quitting. People may work somewhere for 1-3 years but the company could be 5-10 years away from acquisition. Employees have to give the company money at time of quitting to get any equity, which few want to do.

I know the common wisdom, but I also know that there are a couple local technology centered private Slack groups in my area where people will eagerly try to evaluate and possibly buy your options for local startups. They don’t buy everything, obviously, but there is demand for the few cases where contracts allow transfer of the resulting equity.

pm90

> but I also know that there are a couple local technology centered private Slack groups in my area where people will eagerly try to evaluate and possibly buy your options for local startups. They don’t buy everything, obviously, but there is demand for the few cases where contracts allow transfer of the resulting equity.

isn’t this illegal? private stock ownership needs approval from company/BoD to change hands, no?

toomuchtodo

While board approval can be a condition of transfer (consult the options agreement), forward contacts can be used (with counterparty, liquidity, and price risk) when transfer conditions cannot be met to effectuate a de jure transfer.

fnbr

This is why I will never work somewhere with a short post termination exercise period (PTEP). If it’s not at least 5 years, ideally 10, they don’t seriously consider equity something that employees are owed.

marssaxman

I would have ignored anything you said about the value of stock options anyway, having many years ago learned that they are practically always worthless, so making me a straightforward, honest, non-speculative offer would make me more interested in working for your company, not less. Kudos. Keep it up!

goldchainposse

I was a hired early to a startup (my hiring manager was the CEO) that's now public and worth $10B+ that you've heard of. It took them over 10 years to go public, and I would have done just as well putting my money in FAANG, but with lower risk and more liquidity.

LPisGood

Well to be fair 10+ years ago it’s hard to find too many dollar for dollar investments that beat MAAMA.

goldchainposse

True! But it's crazy that the risk, successful startup didn't even beat established tech for returns.

mbesto

I'm not saying this is right or wrong. But, if you're ventured backed, then this strategy is usually at odds with your investors. The reason stock options were used in the past was because you were signaling to everyone (you, your family, your grandma, your early employees, your current investors, your advisors, your future investors, etc.) that you were strapping on to a rocket ship. By paying them more and giving less stock, this means your capital raises don't stretch as far (from a perspective of time). This in turn will be a signal to your investors that you may take the $1M and not the $3B deal (see Google/Yahoo), which they may not like.

retiredpapaya

The Netflix approach to this [1], where Netflix allows employees to choose how much of their compensation is cash vs options seems like the best approach - you can tune based on your risk tolerance.

> Each employee chooses each year how much of their compensation they want in salary versus stock options. You can choose all cash, all options, or whatever combination suits you. You choose how much risk and upside (down) you want. These 10-year stock options are fully-vested and you keep them even if you leave Netflix.

[1]: https://jobs.netflix.com/work-life-philosophy

robocat

The stock options are for common stock, right?

However investors that put money in get preferred shares (not common stock) right?

The tradeoff is not equal: taking less salary and receiving stock of less value seems risky to me. I can't imagine the employees discount is very good (those preferred shareholders don't want to be diluted).

Better sibling comment here with in depth opinion: https://news.ycombinator.com/item?id=43677084 : which answers my question:

  when your options vest, is that you are essentially allowed to make an equity investment in the company with really unfavorable terms (ie ur not even getting preferred stock or any voting rights unlike your average investor).

tomp

> when your options vest, is that you are essentially allowed to make an equity investment

isn't the idea that you buy shares at book value, which is way less than "last round valuation"? so you're getting a discount.

I mean, hopefully that's how it works, I never put enough money when exercising my option to care...

jjeaff

Is there some bonus given if you choose stock options? Otherwise, what would be the incentive of taking options over cash in any amount?

n2d4

An understated benefit is that, if you have 4 year vesting, you can choose after year 1 or year 2 whether you want to stay.

Meaning, if the company's stock went up 2x after year 1, your salary has effectively doubled for years 2-4. If the stock went down -50% however, you just leave and get market salary somewhere else.

So, considering this, the expected value of $100 in stock options is actually more than $100.

hiatus

> Meaning, if the company's stock went up 2x after year 1, your salary has effectively doubled for years 2-4. If the stock went down -50% however, you just leave and get market salary somewhere else.

If you get 25k shares worth <$1.00 and, you won't double your salary even if the share price doubles. Not to mention that only 1/4 would be able to be exercised, and you have no liquidity to realize the gain.

null

[deleted]

dandandan

If you think NFLX is going to increase x%, then your total comp goes up accordingly. If you took straight cash, you'd only recognize those same gains if you had purchased NFLX with it.

fastball

It's actually more than that, because the option costs less than the price of a full share. i.e. if your comp is $400k and you choose 100% stock options as your comp, that value allocation will almost certainly control more shares than if you took 400k in cash and used that to buy all NFLX shares.

If that wasn't the case then yes, there would be no reason to take options as comp because obviously (as you say) you can just buy NFLX on the stock market directly with some or all of your cash.

lbotos

I know a few years ago spotify had a similar selector:

- cash bonus

- RSUs

- More OTE Options

You got to pick two and your ratio. IIRC, 80/20, 60/40, 50/50.

jiveturkey

this is a bad comment for this subject. NFLX options are on a publicly traded stock. the terms are also different than a startup stock option. you've really just introduced confusion into this subject, judging from all the child comments.

in my experience, most startups do offer you a sliding scale of cash vs equity, just not 90% as NFLX does. they may not advertise it or be upfront about it, but i've never personally experienced a startup that wouldn't trade one for the other.

lizknope

Why didn't I get any money from my startup? - A guide to Liquidation Preferences and Cap Tables

https://www.reddit.com/r/startups/comments/a8f6xz/why_didnt_...

I've posted this before but it's a great read. Even if you have millions of shares, the dilution and later investors could still leave you with nothing.

I worked for 2 startups, both failed, but I never got to see the cap table.

justinbaker84

I worked at a startup where I joined as the second employee before they raised any money and I basically got 0.5% of the company. They went on to raise over $100 million in VC.

I got $0 for my equity. Start ups have SO many ways to screw employees out of their equity.

The most basic is that you have options that you are not allowed to sell during equity rounds. If you accept them then you need to pay the strike price and they count as taxable income even though you got shares instead of money so you just lose a lot of money.

Say what you will about Elon, but at Space X employees are allowed to sell their shares for actual money at regular intervals. Very few start ups that succeed allow their employees to do that.

90% of startups that succeed just want to grind down their employees rather than pay them the equity they earned.

lizknope

At both startups we bought our shares early using Section 83(b) of the IRS tax code. That first year when we bought the shares I had to file extra paperwork but it shifts the tax rate to long term capital gains.

https://www.cooleygo.com/what-is-a-section-83b-election/

So I ended up writing checks of $60 and $100 to buy thousands of shares at $0.0001 a share. I left both startups before they went under but everyone lost that small amount. When people ask me how much money I made at the startup I joke that I lose $60.

jmuguy

This is excellent and illustrates that unless you have access to the cap table, you have no idea what your options are worth. Sometimes you can at least get a founder to tell you what the preference stack looks like, and what multiples were given to investors, and that might be enough to kind of sort of work out what an exit looks like.

wyldfire

On this April 13 in these United States, I can't help but think of the incredible inconvenience of how RSUs and shares sold seem to be calculated for the sake of income taxes. Please just add it up and send me the bill. I don't want to pay more than what's due. And I don't want to cheat. For whatever reason, the typical tax interview software guesses wrong or has insufficient inputs when I feed it info from employer + brokerage. So what remains feels like guesswork with liability on both ends.

toast0

RSUs aren't really that bad, unless your employer does sell to cover in annoying ways. Net share withholding works out super simple, the shares that weren't withheld are at the brokerage with the correct basis, and the income and withholding are reported accurately on your w-2.

Options do get pretty nasty if you exercise and hold, when the fair market value is higher than the fair market value; because then you have to have an AMT return and a regular return and reconcile them.

ESPP with a discount was pretty bad the last time I had it; the brokerage said they were specifically required by IRS rules to report the wrong cost basis, and you had to adjust it when you sold, or you'd have the discount reported on your w-2 and again as a capital gain. Maybe that changed, capital gains reporting has changed over time.

Thorrez

I agree options are worse than RSUs. But RSUs are very bad. 3 reasons:

1. My RSUs vest monthly. I've been selling immediately. For the last ~2 years, I guess I've been unlucky, and the sales have generally been small losses. Each of those sales gets washed by a vest that occurred either a month before or a month after. I used to track these by hand in a spreadsheet. It become essentially impossible due to increasing complexity every year caused by the long chains of vest+sale. Now I wrote a 1000+ line Python program to calculate my wash sales. It probably took 20+ hours to write. It takes about 30s to run, that's how large the vest+sale graph is (and the program isn't optimized for runtime). A single sale is now being washed by chains of vest+sale that are extremely long. And due to each vest involving different amounts of fractional shares due to changing compensation and changing tax rates, the washes are constantly doing partial washes, that split lots into sublots. So a single sale might involve many many sublots. The holding period is also propagated to the new lot. The chains are starting to get so long, that if this were to continue a few more years, I would have some sales that are partially long term (>= 1 year) and partially short term, which I can't find any information online about how to file. It takes me hours to format my data from my 1099B and statements into a CSV to put into the program, and hours more to take the output CSV and put it into Turbotax. Quarterly vests would partially solve this problem (you would still get washes caused by multiple vests happening on the say day sold for a loss washing each other, but at least it wouldn't propagate to future or past vests).

I have now resolved to never sell for a loss (where loss is defined as for any sublot within the lot, the sale price is lower than the original basis + the basis added by all the previous sells washed by this sublot's vest), to avoid this problem. This may mean I have to hold on to stocks that I want to sell, potentially until I die.

2a. I live in CA, but worked from MI a few days a few years back. That means I now have to pay MI tax for 4 years. I receive ~48 vests per year (monthly vests of 4 different grants (from the 4 prior years)). For each of those ~48 vests, I need to calculate what percent of the days between grant and vest I worked in MI, and pay that amount of MI tax on that vest. Turbotax has some bugs related to MI taxes and 401ks and IRAs. Even though my 401ks and IRAs have nothing to do with MI, I now have to deal with these Turbotax bugs every year because I have to file MI taxes.

2b. If you need to file NY taxes as a non-resident (like I have to do for MI), it's even worse, because not only do you need to do that calculation for each vest (~48/year in my case), but you also need to file a new IT-203-F form for each vest. That's 48 IT-203-Fs to file each year. And each one is a complex form involving workdays, weekdays, holiday days, sick days, vacation days, etc.

3. If you move between states with different tax rates, your vests are taxed completely at the new state's tax rate. They're also taxed proportionally (based on time between grant and vest) at your old state's tax rate. So they're double taxed. You do end up with a tax credit that undoes the smaller of the taxes. But this means that when you move, for 4 years you're taxed at the maximum tax rate of the 2 states (on at least some portion of the vests). This makes WA->CA movers mad, because all they have to pay CA tax on 100% of their vests immediately. It also makes CA->WA movers mad, because they have to pay CA tax for 4 years on some portion of their vests.

I dearly wish to be paid in cash.

dualityoftapirs

If you've been selling everything at every vest event, then wash sale rules don't apply - essentially the IRS doesn't want you to claim a loss when you haven't effectively closed a position, and if you don't hold any shares, then you have closed the position. Your other two points - states don't do income tax calculations based on the grant, but only what vested while you lived/worked in the state in the respective year of the vesting. Basically you don't owe Michigan income tax for a given tax year if you didn't live or work in Michigan during that tax year.

I think it'd be good to visit with a CPA to cover some of these topics. I'm not saying definitely hire one but I think you may have misunderstandings of the tax codes.

jackcosgrove

Wall Street pays cash. Trading firms pay cash. Cash is the best form of compensation because it's the most fungible*. If you really believe your employer's stock will double in value, you can take your cash bonus and buy shares of it. Of course if you're that confident in your market prediction power you're in the wrong line of work. Wall Street pays cash because it gives employees the power to invest it however they wish (read: no one knows the future so they invest in a diversified basket of assets).

The only downside of all cash compensation is it attracts mercenaries. Personally I find believers and missionaries more pleasant to work with.

* All else being equal, such as the payout schedule.

findjashua

the broker should be adjusting the cost basis in the 1099 to account for wash sale. are you not seeing that? what broker are you using?

MissionInfl

I'm not a tax professional but this hardly seems necessary. Have you consulted with a tax professional to confirm that this is all necessary? How much of a difference does it actually make, i.e. how much tax do you actually pay to MI?

JumpCrisscross

RSUs in private companies are super illiquid.

paxys

You don't have to pay tax if your RSUs aren't liquid.

unethical_ban

I wonder if you worked for a certain california-named company based in another california city... Your experience sounds a lot like mine.

They sell-to-cover when my stocks vest quarterly, which pisses me off because the stock constantly goes up and I wish I could keep them until the time my tax bill is due.

And, I have to manually report to the taxman all the money paid via those sell-to-covers, because even though eTrade sends me the transaction details each year, and they clearly tell the IRS how many stocks I got, they don't tell the IRS how much tax I already paid on it.

scarface_74

When I worked for the company named after a rain forest, we had the choice of sell to cover, sell all or pay taxes without selling shares. I always chose to sell all. I would never have taken 25%-30% of my hypothetical cash compensation and bought one stock. Why would I keep my RSUs?

Now I work at a smaller company doing the same thing (cloud consulting) making the same amount all cash. I much prefer that over cash + RSUs.

lopkeny12ko

> Please just add it up and send me the bill. I don't want to pay more than what's due. And I don't want to cheat.

I have a hard time understanding this comment because this is exactly what employers do when paying out RSUs.

At the end of the year, you get a 1099 indicating the fair market value of shares you've received. There's no trickery here--this is literally the amount you owe income tax on.

I'm not sure what tax software you're using that requires you to guess inputs and numbers. TurboTax makes this trivially straightforward.

blindriver

Those equity percentages in this document are EXTREMELY FOUNDER FRIENDLY and I believe this entire document was written to anchor new employees with lowered expectations on equity. I think this entire document is a disingenuous scam to make new startup employees think that those percentages are okay.

I’ve been in Silicon Valley a long time, since the dotcom boom. My first company, the executive assistant got so rich from the pre-dotcom IPO she quit and bought a vineyard. That’s how things used to be. And we aren’t talking about some crazy ipo, it was before those times.

Fast forward to these days, the startup I worked for got acquired. I was engineer < 15. The founders got low 9 figures, I got 5 figures. Almost everyone got fucked for years of loyalty.

But that’s what YC and other accelerators teach founders. Be cheap with equity. And this document just perpetuates that.

Founders can easily make life changing money but the people that do the actual work get fucked unless it becomes a >100B company like a Facebook. That’s not realistic and they know that. Employees need a bigger piece of the pie when things go great for the company and not just when it becomes a Facebook, Uber, etc.

If you want to know how to evaluate equity, pick a total valuation of the company at exit and then multiply by your stake. If the company needs to exit at > 10B for you to make a life changing amount of money, then ask for much much more equity or don’t take the offer.

ryandrake

It's crazy how "founder friendly" and "investor friendly" (read: "employee unfriendly") the norm has gotten. I would never work for someone else's startup these days. No way, no how. Four orders of magnitude difference between the founders' exit and the early employees' exit is totally unacceptable.

neilv

Yeah, I've been burnt badly by that before.

Which is part of why my founder co-matching profiles mention that I'm looking to spread the equity wealth around among early hires, more than is usual.

If a prospective co-founder is turned off by that, without a really compelling reason, then we'd probably clash on other values as well. And I'd also think there's a good chance they'll backstab me when they think they can.

yard2010

Ah selection bias is the best shield when being used correctly.

Eridrus

I don't think your complaint/experience actually lines up with the numbers here.

In the Post-Series A numbers, the lowest numbers are in the ~0.5% range. This is at most 2 figures off what the founders could get together. In a world where founders together got 9 figures, a senior engineer would get 7 figures, not 5 figures like in your situation.

null

[deleted]

sgustard

The majority of comments here seem to argue the ideal equity share for employees is zero, since it probably won't be worth anything. That seems like an even more founder friendly viewpoint, no? Mass inequality of ownership is how we end up normalizing the corrupt billionaire class. I agree with you we need an industry desire for better ownership terms, but instead I see people arguing employees should just take a salary, look the other way, and let owners hoard all the spoils.

drdrek

Don't get sucked into blind rage over nothing. Why do most employees nowadays prefer cash over options in startups? because for every successful startup where the secretary got a vineyard there are 99 when the startup limps along for 12 years and then closes without a sale. Generational wisdom turned into "Dont get suckered for low wage and options, get a high wage and invest in the S&P".

Will there be lucky founders that become very rich? absolutely. Founders are generally very risk aggressive and are willing to go boom or bust. But for an average person that just want a good life why risk lower living standards for a low change of riches?

If you are very risk aggressive you can push for more equity, but expect your salary to be much lower than your peers. Most veteran SE will advise against it.

lotsofpulp

That is not what people are arguing. Labor sellers should assume equity in a non publicly traded company is worth far less than the labor buyer wants the labor seller to think it is, so labor sellers should demand more cash such that the compensation is competitive with other potential job offers that offer more cash.

dangus

Earning a salary in cash doesn’t stop you from investing the cash. I have never earned equity from an employer but most of my net worth is sitting in publicly traded companies. So obviously I am not lacking company ownership just because the company I worked for didn’t loop me in.

The other reason this isn’t true is that equity becomes a lottery ticket that is written in a founder and investor-preferred manner and is used to fleece mostly young employees who don’t know better and are romanced by the thought of being a part of the next Uber or Airbnb.

The practical reality is that it becomes “this job is worth $150,000 but we’ll pay you $100,000 and you can have some equity that might be worth hundreds of thousands if the casino pays out.”

But then you have investor preference multiples, valuation fuckery, and other ways that even a successful exited company can pay out less than your fair share.

To me cash is king because I can invest it however I want. Equity is fine if it’s for a public company, as that’s effectively just deferred cash as an incentive to stay longer.

habosa

Came to write this same comment. The first 10 employees of a company are so critical to success and they tend to be drastically underpaid. A founding engineer (often employee 3 or 4) would be lucky to get 1.5% at most places while the CTO has 30-50% and they probably have very equal impact on the company in the early days. And engineers do well by comparison. The first customer-facing roles often get barely any equity at all while they hustle to actually make an idea into a business.

The VCs have convinced the founders that they are special people and they deserve 10-100x the rewards of their best employees. They do this to create room in the cap table for themselves of course. They also give the founders early liquidation opportunities to keep them on their team.

It’s disgusting, and the founders wonder why some people don’t want to grind as hard as they do.

Ozzie_osman

> I believe this entire document was written to anchor new employees with lowered expectations on equity. I think this entire document is a disingenuous scam to make new startup employees think that those percentages are okay.

Have to love the HN crowd. A guy goes out of his way to write a very detailed, high-quality guide demystifying a very complex and consequential topic, open sources it so it's free, and immediately people suspect the entire document is build just to make startup employees think lower percentages are OK?

Disclaimer: I know the author personally, so can definitely attest to the motivation behind this guide. I'll also say I've used this guide both as a founder and as a startup employee and it's been immensely helpful.

xyzzy_plugh

Both can be true!

blindriver

The fact that you are a founder that agrees with these extremely low equity percentages for early employees confirms exactly my point. It's to anchor lowered expectations for new employees coming in.

I stand by exactly what I wrote.

Ozzie_osman

Genuinely curious. What percentages do you think are fair and why? As both a founder and employee, I anchored to the market. But maybe the market isn't fair. So what is?

elephanlemon

Conspicuously missing from this is any discussion of clawbacks or repurchase rights, which can be a big deal. Sadly most people do not seem to be too familiar with these, but they should as they are quite common and very dangerous to employees.

https://www.stockoptioncounsel.com/blog/standards-ownership-...

Terretta

Also missing, any discussion of equity-like or profit-participatory structures from LPs (limited partnerships).

Technologists joining one of these should know the "business domain" "partners" are either buying into or awarded partnership interests, but structures can be available for non-business domain roles (in firms that think technology isn't in their business domain cough), such as "profits interests", "synthetic equity", "phantom equity", or etc.*

If the firm has a product and you're helping build it, look for equity-like that let you not only share in profits (if any, most starting things don't have profits) but have a stake in capital events (from asset sale to IPO).

Think of these two forms as something like dividends and something like a combination of options and RSUs. If the profit component is intended as part of annual comp, it should pay at 100% from the start even if you don't "own" it until you vest. Meanwhile if it's a future reward, then both it and the capital-like would have a "tail" that remains in effect if profits or a capital event happens after you leave.

These are very complicated and very bespoke per firm since they are 'made out of' the partnership interests of the LP where ownership is handled as "capital accounts" and may have no accounting method for "goodwill" value separate from partner capital accounts. In such cases, generally partners have shaved off some portion of their rights and allocated those rights to employees, and the mechanisms of this "waterfall" amount to where you stand in that line if at all.

Ideally (a) seek advice from someone experienced with these that (b) you don't have to spend $1200 an hour on.

* Partnerships that understand their business domain is in the technology business — since technology is just another word for tools, and business humans should be tool crafters too — will be using this and have told you about it during interview, and it will all go more smoothly.

jiveturkey

clawbacks are not common, and no one should ever accept such a package. (maybe executives, since they may have other golden parachute provisions.)

repurchase rights are exceedingly common.

mppm

Equity compensation is an essential part of modern corporate incentive structure. In particular, it incentivizes prospective employees to accept lower compensation, by making it appear larger on paper.

guappa

I've always evaluated it at 0, and that's all I got from the equity I got in my whole career. If I didn't think the salary was enough I wouldn't have accepted.

thuanao

AKA fraud.

PopAlongKid

Another resource I've found very useful (disclaimer - no affiliation on my part) is

https://fairmark.com/compensation-stock-options/

There are several books also available, including a 2014 book aimed at financial planners and tax advisors that I have on my shelf and find myself consulting several times a year, as it is still pretty relevant under today's tax law.

pm90

My personal preference has been for post series B companies that have some kind of name recognition and legitimate business model. You get less equity but the chances of the equity being worth something is higher. Plus its a smaller team: just a personal preference, I like smaller teams.

no_wizard

This seems mostly geared toward private companies that grant equity. As it’s part of the Galloway series that targets this audience that makes sense.

I do wonder how much of this applies to RSUs granted by public corps

GeneralMayhem

Basically none of it. RSUs at public companies are as good as cash that just happens to be pre-invested. The tax implications are very simple (they're just regular income like getting paid in cash), and so are your legal rights (you're not much different from anyone who bought a share on the stock exchange). You should risk-adjust their value like any investment, but there's are very few if any sneaky things that can happen to pull the rug entirely.

neilv

Would they be referring to that here?

https://github.com/jlevy/og-equity-compensation/blob/master/...

> Topics **not yet covered**:

> - Equity compensation programs, such as [ESPPs](https://www.investopedia.com/terms/e/espp.asp) in public companies. (We’d like to [see this improve](#please-help) in the future.)

OptionOfT

I got offered .3% as a first developer at a company. That's just insane.

No benefits, $45k pay cut, and even when everything goes well I might break even.

marssaxman

Were they people you'd like to work with on a project you'd like to help build? Maybe it's worth it. Life is for living, after all, and we do a lot of our living at our jobs; there's more to consider than just what you get paid.

callc

I would not want to work so closely with someone trying their hardest to minimize the benefit to me. Since life is for living, we should work on teams where there is genuine respect for all members, not animosity and greed.

The sad fact is that being able to work just for personal satisfaction and not just for money is an extremely privileged position.

jjk7

Until they get rich off your labor and you get bitter about it.

paulcole

Isn't it just insane from your point of view. For somebody else couldn't the same offer be appealing?

sprocklebud

I got hit with a new equity compensation fugazi with RSUs at a small public company recently.

My offer letter pledged something like $100,000 of stock, vesting over four years. I was told that I would receive the grant within the first three months of my employment, once it was approved by the board.

Once I finally received the grant, it was 1/5 of what it should have been. “What gives?”, I inquired.

Apparently the stock incentive plan has a “price floor” for grants at $5 / share, and the stock had plunged to approximately $1 / share at my time of hire.

So my offer letter says my grant is for $100k, but in reality it’s $20k.

I learned this was because there was a limited pool of stock available for employee award grants, and a recent rout in the stock price meant there was an insufficient amount of stock available for grants.

Apparently going forward, offer letters specify the number of RSUs rather than a $ amount. So I guess a charitable interpretation is that it may not have been so much an intentional deception as a set of unfortunate circumstances coming together with some poor oversight on the details of my offer letter.

Still, I am incensed.

I referred to a previous employer’s offer letter and RSU grant for comparison. The offer letter also specified a $ amount, and did not specify how it would determine the price of the stock to calculate the awards by.

In that case, it seemed to be the average closing price of the stock in the month the award was granted. Which I’m content with, but these details also were not specified in the offer letter.

tldr if you get an offer letter for a $ amount of RSUs, make sure to clarify (in writing) how the valuation of the stock is determined for the calculation of the number of units awarded.

pm90

This is strange and possibly illegal. If the stock falls, you should get more stock since they’re worth less. If they don’t have enough stock then they shouldn’t have offered you that as compensation.

In any case… $1- $5 is penny stock territory. I believe you get delisted from NYSE if ur stock stays at $1 for too long.

pyfon

Oh that is bad! It is a 20k/y pay cut you weren't expecting.

If they were keen to make amends they should just bump your pay that much. Unless they are struggling.

By the way I have a similar RSU amount and schedule. So gar so good but cognizant that in the contract they can stop it at any time. I took the risk as I can also quit at any time!

marcusb

All of the RSU offers I ever got stipulated the grant was "subject to the approval of the board", i.e., not guaranteed. That said, I'd be absolutely livid if something like this happened, and would be expecting my manager to either make it right, or I'd look for a new job at the first available opportunity.

You can't do good business with bad people.