[HN Gopher] Guide to Equity Compensation
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       Guide to Equity Compensation
        
       Author : DyslexicAtheist
       Score  : 103 points
       Date   : 2020-02-20 09:51 UTC (1 days ago)
        
 (HTM) web link (github.com)
 (TXT) w3m dump (github.com)
        
       | ditonal wrote:
       | Startup ISOs are totally broken, and VCs and founders would
       | rather write 30 page treatises on all their complexities (of
       | course, glossing over the 99 ways to screw employees), than
       | actually try to improve them.
       | 
       | A small percentage of people got rich off options a handful of
       | times a long times ago, and since then countless people have been
       | screwed.
       | 
       | Public RSUs for stock you can sell immediately on the open market
       | are fantastic.
       | 
       | Common ISOs are toilet paper. At a _minimum_ you should get a 10
       | year exercise window, and if the CEO tries to say that would make
       | it so early employees can hurt cap tables for future rounds, he's
       | basically saying he doesn't consider your equity grant to be real
       | equity as it deserves to be clawed back for the sin of not
       | wanting to stick around for the 15 years it takes startups to IPO
       | these days.
       | 
       | These exact same people will try to convince you that their ISOs
       | are a valid subsitute to liquid RSUs, THEN say that they don't
       | deserve to be "preferred" instead of "common" because the VCs put
       | in actual money (hint: so did you if you turned down a public
       | company to work at the startup. Biggest difference is only that
       | you're way less diversified).
       | 
       | Am I ranting? Of course, but if VCs and founders are going to
       | continually "educate" engineers on their equity offers, engineers
       | need to stand up and inform each other of the pitfalls. I know
       | countless people, myself included, who have been screwed by ISOs.
       | You can actually lose money because the 30 day window forces you
       | to pay strike price + taxes on gains, then you find out that the
       | CEO sold the company at a bargain so liquidation preference
       | kicked in and he just took a huge retention bonus instead.
       | 
       | The way out of this mess is not Github treatises on how to
       | evaluate your equities. The way out is for engineers to
       | continually tell founders/VCs that they will pick public
       | companies instead of startups until ISOs get fixed. If ISOs
       | screwed over VCs instead of engineers, they would have gone to DC
       | and gotten this fixed 10 years ago. At an absolute minimum you
       | shouldn't have to pay a dime in taxes until you've actually
       | realized some money in your checkings account. VCs/founders don't
       | care because they don't have to care because engineers are still
       | too gullible and accept these bogus deals.
        
         | jiveturkey wrote:
         | > Startup ISOs are totally broken.
         | 
         | > Public RSUs for stock you can sell immediately on the open
         | market are fantastic.
         | 
         | Both correct statements, but apples and oranges.
        
         | alakin wrote:
         | Employees should have capped liquidation prefs!
        
         | ericd wrote:
         | I agree that the way a lot of companies structure their equity
         | compensation is terrible. How would you structure equity
         | compensation at a mid-stage startup where a share grant would
         | come with a real, substantial tax hit, without any possibility
         | of liquidity in the near future?
         | 
         | I'm asking because we're just starting to think about how to do
         | this ourselves, and I agree that most equity plans are giving
         | engineers a raw deal. The answer might just be large share
         | grants, at least until the share value makes that unattractive.
         | I'd love to hear other peoples' thoughts on this.
         | 
         | IIRC, much of the reason ISOs work the way they do is because
         | of the way the IRS treats them, and companies that offer much
         | longer exercise windows are having to work around these
         | limitations to do so.
        
           | bradleyjg wrote:
           | How about double trigger RSUs?
           | 
           | The downside is that employees pay ordinary income on the
           | full IPO value, but there are no upfront taxes and no
           | exercise dilemma for people that leave after vesting.
        
         | jagged-chisel wrote:
         | Are options considered an equity grant? I hadn't thought so,
         | but maybe I need to update my own vocabulary.
        
         | ng12 wrote:
         | Exactly this. As far as I'm concerned the purpose of ISOs at
         | companies more than a year old is to trick junior engineers
         | into accepting a lower salary than they would receive
         | elsewhere. Unless you have at least half a percent of a company
         | you really, truly believe in I'd just ignore this article and
         | put the value somewhere between $0 and a roll of lottery
         | tickets.
        
           | UncleMeat wrote:
           | Worse, as OP states, they can cause you to lose money. They
           | can be worth less than zero dollars. Pay piles of taxes on
           | the exercised options and then watch the company get gutted
           | and preferred investors take everything.
        
             | pjbk wrote:
             | Sadly, examples from the dotcom burst and housing crisis
             | abound. It's a double edged sword. I have always preferred
             | to go for early exercising.
             | 
             | "Many of these workers now owe far more in taxes than their
             | stock is worth. Former Cisco engineer Jeffrey Chou, 32,
             | owes $2.5 million in taxes on company stock he purchased
             | last year that has since withered in value. Chou figures
             | that if he were to sell everything he owns, including the
             | three-bedroom Foster City, Calif., townhouse that he shares
             | with his wife and 8-month-old daughter, the family still
             | could not pay the bill."
             | 
             | * https://www.chicagotribune.com/sns-tech-taxes-story.html
        
         | alecbenzer wrote:
         | > don't deserve to be "preferred" instead of "common" because
         | the VCs put in actual money
         | 
         | I agree with most of what you said, but a nit: one perspective
         | I've heard on the motivation for preferred stock is this:
         | 
         | Suppose I give you $10M to start a company in exchange for 10%
         | of it. You then easily sell the company for $9M, keeping 90% *
         | $9M = $8.1M for yourself and returning $900k to me. Preferred
         | (non-participating, 1x) shares prevent this problem by making
         | sure you can't just run away with the money: you have to
         | actually use it to build the business.
         | 
         | People investing in the company in non-liquid ways (e.g., the
         | founders or engineers, via opportunity costs) aren't in the
         | same boat, because their opportunity cost can't be immediately
         | liquidated.
        
         | zyang wrote:
         | VCs and startup founders are shooting themselves in the foot.
         | It makes very little financial sense to work at a startup vs
         | FAANG these days.
        
           | spurdoman77 wrote:
           | Ok cool, Il tired of seeing these startups popping up. Great
           | thing that they are now thing of a past as they wont be able
           | to hire anyone. /s
        
             | pjbk wrote:
             | A few startups are realizing it is a rigged, unfair game
             | and are trying to balance things a bit. They are offering
             | stock purchase and exercise windows valid for several
             | years, instead of just months or even days. Unfortunately
             | it is still not a widespread practice. I have yet to see a
             | company equalizing stock priorities of employees vs VCs.
        
           | notJim wrote:
           | Yeah exactly. Early in my career, I loved working at
           | startups, and aside from compensation would prefer to do so
           | again, but the opportunity cost now is way too high. The one
           | advantage I see at a startup is that if you pick one with a
           | decent engineering culture, you can learn a lot more than
           | most FAANG roles (although you'll probably learn more at the
           | best FAANG roles than at good startup roles? Unclear.)
        
             | alecbenzer wrote:
             | I think startups are a bit of a crapshoot even in this
             | regard. You'll learn a lot at a good one, but could
             | potentially learn a lot of bad habits at a bad one.
        
           | bradleyjg wrote:
           | Indeed. Real upside is the only thing that lets them at all
           | compete for employees. Investors facilitating deals that
           | screw early employees are poisoning the well for all their
           | future investments.
        
         | tptacek wrote:
         | Some of the reasons VCs get a better class of shares than
         | employees are structural and unlikely to go away no matter how
         | ISOs are structured; for instance, VCs get liquidation
         | preferences for reasons that are sort of intrinsic to the
         | concept of equity investment.
         | 
         | The exercise window thing is a valid point and is a reason to
         | devalue employee options.
        
           | fountainofage wrote:
           | Then perhaps the start up should just pay above market rate
           | in salary and not offer any ISOs since those ISOs are so dang
           | valuable but couldn't possibly be given the same liquidation
           | preference?
        
             | tptacek wrote:
             | I mean, I agree. I think employees generally under-value
             | equity, for understandable reasons, and that it's probably
             | more efficient to compensate them in cash. That does mean
             | that when the company sells, the upside goes entirely to
             | management and investors, but I guess you can't have it
             | both ways.
        
         | simonebrunozzi wrote:
         | Fully agree with you. How would you solve it then - besides
         | engineers being more explicit with founders? (not trying to be
         | smart with you; honest question).
        
       | corporateslave5 wrote:
       | Basically everyone knows by now, being an employee at an early
       | stage startup is a suckers bet. You're literally working to make
       | someone else rich. Just go work for FAANG, or highest cash comp,
       | and jam that money into tech stocks.
        
         | majormajor wrote:
         | It sucks if you want to work on new ideas, and not just be a
         | cog in a giant machine, but don't have an idea of your own you
         | think is worth founding. The money is the trade-off for the big
         | corporate shenanigans and relative lack of intrinsically
         | motivating work.
        
         | ska wrote:
         | This is often true from a raw compensation point of view, but
         | it isn't as if the jobs are fungible.
         | 
         | Nothing wrong with deciding a startup is best for you, so long
         | as you are going into eyes open and don't believe some nonsense
         | like "the options will make up for the salary difference".
        
         | tempsy wrote:
         | I got lucky though at 2 startups, and day to day probably a lot
         | more interesting than working as another cog in a big co.
         | 
         | Definitely made more than I would've given my level.
        
       | jacobschein wrote:
       | So many of my friends have been screwed over by the technical
       | nuances of equity compensation.
       | 
       | Started Compound (https://withcompound.com) to solve this problem
       | (we generate personalized analyses to help you understand your
       | equity - tax implications, potential value, etc).
       | 
       | If you have any questions/feedback, email me:
       | jacob@withcompound.com.
        
         | wtvanhest wrote:
         | Just out of curiosity, how does compound make money?
        
           | [deleted]
        
       | juliend2 wrote:
       | I wish there was a canadian version of this.
        
         | ska wrote:
         | Canadian isn't much different really in practice, but there
         | isn't an 83(b) equivalent iirc. The specific tax detail vary,
         | but from 30,000 feet it looks pretty similar.
         | 
         | Overall it's pretty comparable to the non-SV US. There is less
         | VC & PE money floating around (generally investment is more
         | conservative). Common stock options or grants are going to be a
         | gamble for the same reasons as in the US.
         | 
         | Tax wise, you capital rates rather than normal (i.e. 50%
         | treated as regular income). You may get a gain/loss relative to
         | FMV in year you exercise, same as US.
         | 
         | Most of the advice carries over directly, mutatis mutandis.
        
         | H8crilA wrote:
         | Most of those things are pretty international. Finance is a
         | very old domain, and as a famous man once said (albeit
         | specifically about speculation, but it also applies to the
         | structure of the contracts): "There is nothing new in Wall
         | Street. There can't be because speculation is as old as the
         | hills. Whatever happens in the stock market today has happened
         | before and will happen again."
        
       | mmxmb wrote:
       | Another good resource: https://www.holloway.com/g/equity-
       | compensation
        
       | daenz wrote:
       | I worked for a startup founder and personally watched him screw
       | advisers out of stock agreements using different tactics, from
       | technicalities in the agreements to outright not honoring the
       | agreements when he knew it was disadvantageous for them to pursue
       | him legally. He gloated about it and would speak very highly of
       | all the ways he could manipulate situations.
       | 
       | In the end, I left and the startup went under, and I told him
       | directly that I didn't trust him (to his surprise). The lesson
       | that I learned was that I'd be a fool to take equity in a
       | startup, given all the ways I could be screwed, and my lack of
       | resources to pursue any legal recourse. Cash only, from now on.
        
         | fossuser wrote:
         | I think this is the wrong lesson and people are generally too
         | extreme when valuing this.
         | 
         | Are there risks with ISOs? Yes.
         | 
         | Should you value them 1:1 with cash? Probably not.
         | 
         | Should you value them at $0? Probably not.
         | 
         | People should make decisions based on the company, what they're
         | doing, and how much they trust the board/founders.
         | 
         | It'd be a mistake to categorically dismiss equity since that's
         | the best way to leverage your human capital into wealth.
         | 
         | It's also a mistake to think that equity is valued exactly at
         | what the company is advertising it as when trying to hire you.
         | 
         | There's some risk, but engineers should consider their options.
        
         | sub7 wrote:
         | Your problem wasn't the structure of your comp, it was the
         | payer of your comp.
        
         | jldugger wrote:
         | > In the end, I left and the startup went under, and I told him
         | directly that I didn't trust him (to his surprise).
         | 
         | A classic example of an individual who would be 10x richer if
         | they were 10 percent less greedy.
        
       | andrew311 wrote:
       | Selling private shares / options on the secondary market is near
       | impossible if the company isn't on something like SecondMarket.
       | Right of First Refusal, Co-sale Agreements, and the challenges of
       | sharing information with a 3rd party make this difficult. That
       | said, has anyone succeeded and written about their experience?
        
         | spurdoman77 wrote:
         | If company is valuable enough smart investors will flock around
         | the shareholders who even have very minor ownership. I was
         | sceptical at first but then saw it happening with a profitable
         | company I was following. I thought people were stuck with their
         | shares, but since the company was profitable it attracted
         | investors looking for better returns than public stocks.
        
           | ska wrote:
           | People show up when the risk gets low enough.
        
             | CalChris wrote:
             | De-risking is something a company will go through
             | progressively.                 1. An idea? Risky.       2.
             | + funding? Less risky.       3. + proof of concept? More
             | less risky.       4. + an MVP? Less risky still.       5. +
             | paying customers and metrics? Less risky again.
        
               | ska wrote:
               | Right. And when there is a bunch of illiquid stock around
               | but the risk has reduced enough people will sniff around
               | for (or create) a secondary market. Usually well past
               | your #5 though.
               | 
               | If the risk is too high they are all happy to let you
               | carry it for a while.
        
               | CalChris wrote:
               | If the risk is low then the rewards will be low as well.
               | I think the problem that VCs face in seed is the deluge
               | of pitches. In A rounds, things have settled down.
        
               | ska wrote:
               | We are specifically talking about secondary markets,
               | though. They only really happen I think when the risk is
               | low but people are illiquid, or occasionally when the
               | hype is insane.
               | 
               | This is a separate thing from the natural evolution of
               | risk over startup life. That happens to every one. Viable
               | secondary markets letting you take some money out early
               | don't happen in most cases.
        
         | djannzjkzxn wrote:
         | It's hard in theory, easy in practice if your options are worth
         | millions. I have friends who did it. I don't know too many of
         | the details but they made some kind of contract with a
         | financial firm to sell the upside from the stock without
         | actually "selling" the stock. The fees are not terrible, like
         | single digit percentages. These firms don't want to talk to you
         | if you have a small amount of equity because it isn't worth the
         | overhead to make a transaction.
        
         | tempsy wrote:
         | No it's not. If that were true none of these marketplaces would
         | exist.
        
           | andrew311 wrote:
           | I should clarify that it is certainly doable for widely
           | recognized companies, but it's very difficult for the
           | majority of startups that no one has heard of even if they
           | have some success. Also, getting on these marketplaces also
           | goes much better with company cooperation and many startups
           | don't have the time or willingness.
        
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