[HN Gopher] The Guide to Stock Options Conversations
       ___________________________________________________________________
        
       The Guide to Stock Options Conversations
        
       Author : redbell
       Score  : 119 points
       Date   : 2024-04-14 12:45 UTC (10 hours ago)
        
 (HTM) web link (zaidesanton.substack.com)
 (TXT) w3m dump (zaidesanton.substack.com)
        
       | hobs wrote:
       | Why are conversations not like this? Because shady folks want to
       | take advantage of people's enthusiasm about maybe striking it
       | rich and do what they can to let the target's imagination do the
       | work.
        
         | earnesti wrote:
         | I think the most common reason is, that people just want to
         | avoid uncomfortable conversations. Back in the days I was a
         | startup founder, my beliefs were always pretty different from
         | the other stakeholders, and in the end everyone takes their own
         | risks. Having this kind of conversation can be easily
         | interpreted as a recommendation or discouragement, and I wanted
         | to do neither. And while you can also explain the
         | technicalities etc, in the end many people just want the answer
         | "what should I do" from someone.
        
           | riehwvfbk wrote:
           | There's a reason these uncomfortable conversations are
           | uncomfortable, and it's precisely that: you, as a founder,
           | know that the odds of the employee striking it rich are slim,
           | but have to sell them on joining the company.
        
       | lucas_the_human wrote:
       | In comp packages you also want to look for the exercise window
       | clause. Some companies say you have to exercise your options
       | within 90 days from leaving but I've worked at a startup where it
       | was 5 years which is more employee friendly.
        
       | gumby wrote:
       | I was counseled years ago to be VERY careful about these
       | conversations. You can't encourage, or come off as encouraging,
       | any employee to exercise or not -- if the bet goes the wrong way
       | (company succeeds but empmdidnt exercise or vice versa) you / the
       | company could be sued and it's an SEC violation.
       | 
       | One thing you should do is support early exercise (meaning
       | exercise any time, even before you've vested; company can
       | repurchase and the same price any unvested shares if you leave).
       | This is especially good for early hires when the price is
       | extremely low and 83(b) means you avoid a tax bill until you
       | sell. In later stage companies this doesn't help as much though.
       | 
       | I do agree with the author that comp secrecy is not just stupid
       | but destructive.
        
         | hackernewds wrote:
         | tax bill before you sell scenario is valid for ISO. NSOs is a
         | whole other ballgame, with its own tax benefits
        
       | jawns wrote:
       | > The "Assume your equity will be worth nothing" mantra.
       | Especially in 2024, people prefer to treat stock options as a
       | lottery ticket and not as an investment.
       | 
       | The post itself provides ample evidence for why this is a
       | rational position, especially for people with even mild risk
       | aversion.
       | 
       | For instance, look at the table of "Startups that exited for more
       | than they raised." Even among those who raised a Series E or
       | later -- the most likely to exit -- only 40% experienced a
       | favorable exit, and among those, the mean valuation growth was
       | 2.26X.
       | 
       | Under optimistic assumptions, that's a "double your money"
       | scenario with 40% odds, which is a not even a great bet in the
       | aggregate -- but a pretty terrible bet for any individual.
       | 
       | Financial advisors counsel people all the time not to put their
       | eggs in one basket. That's why index funds like VTI are so
       | popular. They let you diversify your investments.
       | 
       | Heck, putting so many eggs into the basket of your employer is
       | risky even after it goes public! I had a publicly traded employer
       | who had a 401(k) match paid in company stock. Every pay period, I
       | sold that stock and bought index funds instead.
        
         | throwarayes wrote:
         | Ugh yeah I turned down a job offer even from seemingly ethical
         | and nice startup in large part because I'd be exchanging actual
         | publicly traded RSU vesting in the future with equivalent in
         | options.
         | 
         | It's hard to trade in somewhat certain money for likely
         | fictional Stock Options. Though I'd possibly trade RSUs from
         | company A for company B.
         | 
         | There's almost like a two tier employment system between those
         | at FAANG or adjacent with actual likelihood of a healthy payout
         | and those with options / lottery tickets.
        
           | cbsmith wrote:
           | > Ugh yeah I turned down a job offer even from seemingly
           | ethical and nice startup in large part because I'd be
           | exchanging actual publicly traded RSU vesting in the future
           | with equivalent in options.
           | 
           | I did the same thing. The options were from a company that
           | had just IPO'd named Google. You may have heard of it. ;-)
        
           | hibikir wrote:
           | Yeah, the gamble only pays off for a company that has a
           | growth so strong, and a plan so safe that the downside is
           | quite low. They have to give you more options because they
           | know they are worse than RSUs, so the pay really can end up
           | being higher than FAANG, but still with some gambling
           | involved. Those companies exist (See, Stripe 10 years ago),
           | but there are so few of those, it's harder to find them than
           | just go to FAANG.
        
         | hackernewds wrote:
         | 40% chance to double your money in 4 years is an expected value
         | of 20% compound growth a year. Seems like a solid bet vs VTI
        
           | dahinds wrote:
           | Your calculation assumes that the other 60% of the time you
           | get to keep your original investment, but there's a good
           | chance that you lose it all.
           | 
           | This is also the calculation for an investor, and is not
           | really relevant for an employee option holder.
        
             | thedufer wrote:
             | In fact, it sounds like the 40% includes all exits,
             | including those that returned only 1x. That would mean that
             | the 60% is all 0s, and that the chart shows a negative
             | total return in all rows, without even discounting for the
             | holding period.
        
           | jawns wrote:
           | But the way it works per individual is that you have a 40%
           | chance of "winning" and a 60% chance of losing your
           | investment completely.
           | 
           | VTI carries the risk that your investment could lose value in
           | the short term, but over a longer time period, I'll take VTI
           | over stock options any day.
        
             | deschutes wrote:
             | Better odds and no work at a game of chance. That's pretty
             | damning.
        
           | lostemptations5 wrote:
           | This really depends on an individuals risk tolerance.
        
           | baq wrote:
           | Volatility adjusted is probably quite shit.
        
           | repsilat wrote:
           | This math is way off. _Guaranteed_ doubling in 4 years is a
           | 19% per annum return. If the "not doubling" case is "break
           | even" (generous) then the expected growth is under 10% per
           | annum.
        
         | dan-robertson wrote:
         | Yeah, the real reason that kind of advice is useful for lots of
         | people is that those people aren't risk neutral. It's also hard
         | to value the options correctly. There're a bunch of reasonable
         | things Ben Kuhn has written about startup stock options, with
         | the main premise being that if your salary suffices and you
         | intend to give the rest to charity (and want to increase the
         | amount you give) then you are risk neutral and so you should
         | try to value the options properly. Eg this post and several
         | linked from it: https://www.benkuhn.net/offer/
        
         | dasil003 wrote:
         | > _Financial advisors counsel people all the time not to put
         | their eggs in one basket._
         | 
         | One nuanced take that I've found useful: diversify to preserve
         | wealth, but concentrate to build it.
         | 
         | To be clear, I'm not advocating against the default view that
         | stock options are lottery tickets, because from a pure
         | financial point of view that's close enough to the truth.
         | However, it's important to understand that outlier wealth comes
         | from ownership of businesses, and the whole point of being at
         | an early stage startup (whether as founder or early employee)
         | is to be an agent in the success of an outlier business.
         | 
         | There's no way around the fact that this is a fundamentally
         | risky proposition. The odds are always against you--especially
         | given how much one can make in FAANG, it's a particularly
         | difficult time to make any kind of expected-value argument for
         | working at a startup. That said, there will be more outliers in
         | the future. Many people who work on those will see generational
         | wealth far exceeding the rank and file of FAANG. They will have
         | gotten there via a drive to do something new and different, and
         | working together to achieve something that the majority of
         | rational people deemed impossible. Despite future dismissals
         | about luck, or odds, or averages, or reproducibility, noone can
         | take away what they will have accomplished through the sweat of
         | their brows and choices made along the way in the face of
         | massive uncertainty.
         | 
         | Ultimately, the best reason to join (or found) a startup is
         | because you really want to try to do a hard thing with a group
         | of people you trust and admire enough to go into the trenches
         | with for the next 2-5 years. It can pay off, but the mentality
         | necessary for success is diametrically opposed to good
         | financial advice.
        
           | earnesti wrote:
           | > The odds are always against you--especially given how much
           | one can make in FAANG, it's a particularly difficult time to
           | make any kind of expected-value argument for working at a
           | startup.
           | 
           | This kind of advice often assumes that it is easy for anyone
           | to get a FAANG job. I got rich from a startup, before that I
           | was working for a bigger companies and I'm very sure that I
           | would never have been successful in that game. I'm fairly
           | sure that corporate jobs work out for quite different
           | persons.
        
       | OtherShrezzing wrote:
       | >This calculation doesn't take into account the dilution during
       | future funding rounds.
       | 
       | It's fairly useless to have these scenario planning conversations
       | with your staff without describing dilution events - they're
       | fairly inevitable. If you've told all the staff that there are
       | three general scenarios, you're going to lose a lot of trust &
       | goodwill when you hold the all-hands meeting where you announce
       | "oh yeah, there's mystery scenario four, where your returns
       | decrease in value, and there's nothing you can do about it, and
       | we might do it again".
        
         | bradlys wrote:
         | Ultimately, dilution doesn't matter for 99% of employees. You
         | could experience 10x dilution but if the price goes up 100x -
         | you're still up 10x. Would it be great if you went up 100x and
         | no dilution? Sure but that's not how it works.
        
           | saulpw wrote:
           | In actuality how it works is that the price goes up 10x and
           | you experience 10x dilution. So everything seems up and to
           | the right and the founders are 10x but when it comes time to
           | cash out you're lucky to get a small bonus.
        
             | bradlys wrote:
             | Maybe in some cases but I often see founders getting
             | diluted a lot as well.
             | 
             | Many times when startups get acquired/whatever - founders
             | will get next to nothing because the investors had
             | liquidation preferences. The founders still go through with
             | it though cause it allows you to start another company and
             | raise rounds. If you become known as a founder who
             | prioritizes himself over his investors - who is going to
             | give you money...?
        
       | datavirtue wrote:
       | I don't think stock options should be seen as a retention
       | incentive. Maybe they incentivize me to knock it out if the park
       | but if I don't care about the company anymore at best they are
       | "golden handcuffs" that prop up the illusion that the holders
       | care about the company.
        
       | whiplash451 wrote:
       | Options conversations are hard for a good reason. The underlying
       | mechanics are actually complex. You can't explain an employee
       | what the outcome would be for them without telling them about
       | preferential shares, double-dipping, etc. Good luck building a
       | company on full transparency on all this. Most investors would
       | think you're crazy and finance the startup next door.
        
         | iamacyborg wrote:
         | All you'd need to do is have a glossary and an open cap table,
         | no?
        
         | whiterknight wrote:
         | I'll be satisfied with a market cap thanks. They won't even
         | tell you how many shares there are.
        
       | hbrav wrote:
       | > In some companies, the initial job contracts are misleading,
       | and mention a nominal price of $0.01.
       | 
       | Is he suggesting that the initial job contract does _not_ state
       | the exercise price, and relies on the employee mistakenly
       | thinking that $0.01 is the exercise price?
       | 
       | This seems like it stems for a culture that we have of employees
       | (or potential employees) just never asking questions about
       | contracts that are presented to them. And I think there's a lot
       | of employers that expect that to be the case too. I've once had a
       | manager tell me with a straight face when I requested changes to
       | a contract "I'm sorry, I can't get this changed. You'll just have
       | to sign it." My reply of "I don't believe it's in my interests to
       | sign that" was not something that was in his world-view.
        
         | bionsystem wrote:
         | Could be a misread of certain 10K which state a par value of
         | $0.01, which has no particular meaning at any point in time of
         | the life of a company (it's just a convention).
        
       | benjaminwootton wrote:
       | I think there is way too much scope for bad actors in this. The
       | employer holds all of the information and all of the cards.
       | 
       | I was a tier 1 significant common shareholder in my own company
       | and saw a bunch of shenanigans. The rank and file employee with
       | 0.00X% stock options subject to weird rules and tax doesn't stand
       | a chance.
       | 
       | From the employees perspective, have to find a massive outlier in
       | terms of company success and then hope to not get screwed or be
       | diluted to hell. Lottery ticket odds are the right ballpark.
        
       | spxneo wrote:
       | whew thought this was a guide on how to avoid getting manipulated
       | on social media into buying calls and puts after reading DDs
       | 
       | i think best thing to do is not offer illiquid stock options but
       | a sliding scale revenue share.
       | 
       | Of all the startups that I have been a part of, only 1 found
       | buyers for the stock options but even then it was too little
       | because it didn't IPO, it just sold to another player.
       | 
       | It's down right misleading to offer pieces of paper with the
       | right to buy a stock that has almost nil chance of seeing
       | retailers without disclosing the odds. The odds are close to nil
       | for startups looking to IPO.
       | 
       | By doing revenue share, it forces you to be long term orientated,
       | you are now focused on growing a steady stream of net positive
       | cash flow. This puts you in a much better negotiating position,
       | you can use leverage from banks to get anywhere from 30~60 cents
       | on the dollar, to redistribute back into operations or bonuses.
       | 
       | THEN you can accept that invite from a VC or PE (dont recommend
       | it due to the time constrained nature of PEs that are
       | incompatible with long term orientated management) and absolutely
       | have the odds in your favour.
        
       | dsr_ wrote:
       | "All the (unneeded) secrecy around the compensation package - you
       | are not allowed to talk about your salary and stock options with
       | other employees, and in some places not even with your manager."
       | 
       | In the United States, this is not just unnecessary secrecy: this
       | is completely illegal. Trying to forbid employee-to-employee
       | conversations about compensation will land the company in
       | trouble, and every manager should know this.
        
         | rybosworld wrote:
         | A company I worked at years ago, the VP of the department sat
         | in on all of my annual reviews with my manager. He would mostly
         | just listen in. But at the end of the meeting he would always
         | say something to the effect of: "as you know, you can't discuss
         | your compensation with coworkers." I knew it was illegal for
         | him to say that but, if it's not in writing then there's
         | basically no recourse.
         | 
         | I understand this to be a fairly common experience in the U.S.
         | workforce.
         | 
         | When it comes to labor laws in particular, the rate of
         | enforcement is extremely low.
        
           | pizzafeelsright wrote:
           | Why would you want to know what you're making compared to
           | your coworkers?
           | 
           | You agreed to the pay. Want more? Ask more. If you're making
           | 2x more than your "peers" would you take a cut to equal pay?
        
             | mym1990 wrote:
             | The point is that there is an information imbalance, which
             | enables one side to have more power in negotiating. Sure I
             | can say "give me more money" but if the employer presumes I
             | have little information on my co-workers, they can just say
             | no. But if I call the bluff and say, I want more money
             | because I know a co-worker makes X, it is harder to say no
             | for the employer, although obviously not impossible.
        
               | pizzafeelsright wrote:
               | The employer doesn't know how much you'll work, if you'll
               | quit early or give up or make mistakes or not bother to
               | show up.
               | 
               | Information is missing on both sides.
               | 
               | Contracts are open with all Information available. To
               | that route if you're wanting to make more than the W2
        
             | ethbr1 wrote:
             | Keeping employees from discussing compensation is the
             | easiest way for employers to undercompensate employees (and
             | avoid keeping pace with the market).
        
               | pizzafeelsright wrote:
               | The market is the average and the market is always open.
        
             | gopher_space wrote:
             | I'm trying to minimize my labor while maximizing my income,
             | within a system designed to produce asymmetrical
             | information.
        
               | pizzafeelsright wrote:
               | You're trading your skills, time, and experience without
               | taking the risk of capital and legal risks.
        
               | ToValueFunfetti wrote:
               | Sure, and we're trading it for money. If the question is
               | "why would you want to know what your coworkers make",
               | the answer is "so I can leverage that information during
               | negotiation for more compensation". If the question is
               | "why wouldn't you want to optimize for your employers'
               | ROI, considering they take on all of the risk", then I
               | wonder why you suggested it would be absurd to take a 50%
               | paycut.
        
               | gopher_space wrote:
               | Like everyone else in the Limited Liability Corporation?
               | Doesn't that make me _wise_?
        
             | peteradio wrote:
             | Because you don't have a clue what the market will bear.
        
           | SilasX wrote:
           | >he would always say something to the effect of: "as you
           | know, you can't discuss your compensation with coworkers." I
           | knew it was illegal for him to say that but, if it's not in
           | writing then there's basically no recourse.
           | 
           | Follow-up email: "Thanks for the helpful feedback in the
           | review! And yes, as instructed, I would never dream of
           | talking to co-workers about compensation. I know that's
           | against policy."
           | 
           | Then, either he puts in writing that it's not policy, or
           | you've started a paper trail.
        
             | usrnm wrote:
             | You're also fired. Nothing wrong with that, just saying
        
         | sgtnoodle wrote:
         | In my experience, a culture of radical employee-driven
         | compensation transparency can lead to toxicity. A subset of
         | folk have a tendency to become obsessed, and increasingly more
         | resentful about their particular notion of fairness. Then from
         | that, folk start to play the victim, grasping for explanations
         | that don't require introspection or admitting individual
         | responsibility. In that environment, the company is forced to
         | take a defensive position, which makes the culture even more
         | toxic.
         | 
         | What I've seen work well is the company taking pro-active steps
         | to be transparent about compensation in aggregate. For example,
         | HR can put out a periodic report documenting compensation
         | metrics by job title and experience. They can also slice the
         | data along various social factors to quantitatively show
         | whether there's any indicators of unintentional bias. From
         | there, another good idea is for the company to regularly apply
         | adjustments independent from performance, in order to keep the
         | metrics healthy.
        
           | whiterknight wrote:
           | Your first paragraph kind of describes employees behavior in
           | general.
        
       | latchkey wrote:
       | I've been in the tech industry for 30 years. I've also been
       | mostly startup based my entire time.
       | 
       | I've only ever had options "work out" a single time and that was
       | because long after I left the company (I bought my vested
       | options), it went public and my options converted into actual
       | stock. However, the stock was absolute shit worthless for about
       | 10 years, so I hung onto it thinking one day, I'd sell it and
       | harvest the tax loss. Then, during covid, WSB came along and
       | randomly pumped it and my limit order for the very tip of the
       | market, was actually filled. Much to my amazement. Then, the
       | stock went to the bottom again almost the next day. I think I
       | "profited" about $5k total out of that deal across many years.
       | 
       | My last company, was supposed to go through a SPAC, likely so
       | that the execs could dump on retail. I spent like $30k on my
       | options and near the end of everything in the hopes of getting
       | some of it back, the whole deal fell through and I got laid off
       | for the first time in my career.
       | 
       | Maybe I just have bad luck in these things, but every time I
       | picked a higher salary over more options... it worked out better
       | in the long run, by a lot.
       | 
       | Now that I'm CEO of my own business, I have zero plans to ever go
       | public or even sell the company. I'd much rather have it be
       | focused on stable revenue generation, and make sure to pay people
       | well, and give company performance bonuses along the way. Yes, of
       | course, we will also give options out, as the industry expects
       | it, but I'm not going to make it a focus (by preferring good
       | salaries, benefits and a stable gig). I'll be upfront about my
       | plans for anyone joining. I would much rather be real with people
       | than give them any sort of false hope. We are just starting, so
       | let's see how that works out over time.
        
       | bradlys wrote:
       | It's a really fucking bad time to be joining startups. They're
       | picky, offering shit comp on top of it, and have very little
       | chance of a sizable liquidation event for employees in a long
       | time.
       | 
       | Idk if I'll join a startup again in the next few years. It's
       | basically taking salary only - which can be anywhere from 1/2-1/4
       | of my normal pay. Why waste your time?
       | 
       | I hope one day startups will offer something of value again. For
       | now, it's a race to the bottom.
        
         | cmmeur01 wrote:
         | I think it's more complicated than that and one big factor is
         | location.
         | 
         | In my midwestern experience startups are paying more cash than
         | other businesses where software is a cost center.
        
           | bradlys wrote:
           | Well, sure. I'm talking mostly about the US coasts where most
           | of the YC audience is. HN is a very SV focused website.
        
       | JonChesterfield wrote:
       | Whoa no. Absolutely no telling employees the details. The whole
       | point of stock options is that employees can't value them
       | accurately and you probably don't have to pay them.
       | 
       | That's the whole magic trick. Come work for us! We can only pay
       | $50k in boring everyday money, but here's some tokens. We don't
       | know what they're worth, and you can't spend them for many years
       | or maybe not at all, but look at this picture suggesting they
       | might be worth lots! Works really well on people new to the
       | workforce.
       | 
       | Actually giving employees a means of valuing it, notably that
       | their options turn into a class of shares that get paid after
       | lots of other people and a sketch of how dilution works out in
       | the meantime, stops them thinking it's a lottery ticket. It
       | becomes a very low chance of winning less money than the
       | opportunity cost relative to working elsewhere.
       | 
       | Much more fun for employees are RSUs. They have the same nice
       | trick of becoming free when people quit. They let you adjust
       | people's pay without annoying them as much as a salary freeze or
       | reduction. A three or four year vesting period with roughly
       | annual grants is near perfect as a salary retention tool.
       | 
       | Also rsu induced pay inflation has really hurt the startup
       | recruitment pitch which helps defang an existential threat to
       | your public company.
       | 
       | Not really what I want as an engineer but the incentive gradient
       | is very clear.
        
         | rustcleaner wrote:
         | >That's the whole magic trick. Come work for us! We can only
         | pay $50k in boring everyday money, but here's some tokens. We
         | don't know what they're worth, and you can't spend them for
         | many years or maybe not at all, but look at this picture
         | suggesting they might be worth lots! Works really well on
         | people new to the workforce.
         | 
         | If I have to be short theta, at least be a [company] man and
         | make it something like 75-delta >720 DTE calls. Ideally let me
         | sell 50-delta <360 DTEs to the new on-boards as well! :^)
         | 
         | Long longer dated ITM calls protect downside in IV spike, and
         | being short shorter (relatively) dated ATM calls pays me more
         | theta than I pay for the ITM while the ITM gives me much needed
         | vanna if the underlying shits the bed on my spread (assuming
         | skew exists).
        
           | rustcleaner wrote:
           | The above is a diagonal. Another option could be to be in an
           | equivalent vertical (both shorter expiry) and then long a 2-5
           | delta back-dated put to get vanna for downside protection.
        
         | jjav wrote:
         | There are IMO two points in time where joining a startup makes
         | sense.
         | 
         | One is very early, _iff_ the startup supports early exercise.
         | Join, immediately do an early exercise of all your options and
         | file an 83(b). This only makes sense if you join so early that
         | you can afford to exercise all those options for an amount of
         | money that you won 't mind losing if the company goes nowhere.
         | Typically this only makes sense if the exercise price is in the
         | few pennies range (but depends on your finances). So before a
         | series A at the very latest.
         | 
         | This is good because you can now work there are long as you
         | want but you are also free to leave if things become
         | unpleasant. As long as you spent at least a year there, any
         | shares you vested prior to leaving are yours for good. If the
         | company IPOs many years after you leave, you still get
         | something.
         | 
         | The other good time is when the company is already large and
         | well-known and clearly on the path to an IPO. You'll get far
         | less ownership obviously, but probabily of success is much
         | higher.
         | 
         | The worst time to join a startup is anywhere in between. The
         | exercise price of your options is too high on day 1 you can't
         | afford to buy them, then you work there for years and become
         | vested on paper but can't do anything about it, then you leave
         | prior to an IPO and you still can't afford to buy the options
         | so they cancel and you are left with nothing.
         | 
         | I've done each of these scenarios, some more than once.
        
           | robocat wrote:
           | If you want to spend money on startup shares, why wouldn't
           | you buy preferential shares? The median value of common
           | shares is muck - converting options buys you risky common
           | shares and causes tax liabilities.
           | 
           | Angel investing is extremely risky, and converting options is
           | riskier than that! Common shares are much much higher risk
           | than preferential shares.
           | 
           | Plus diversification is good. Concentrating your assets and
           | job into one investment is speculation: great when you win
           | but terrible when you lose.
           | 
           | I reckon we are conceited to think we can invest smarter than
           | professional VCs? They lose all the time even though it is
           | their fulltime job and they are insiders on the rules of the
           | game.
        
             | Glyptodon wrote:
             | There really isn't much tax liability for exercising
             | options when the fair market price is still minimal unless
             | you have an awful lot of them.
        
               | jjav wrote:
               | You'd want to buy when exercise price and FMV price are
               | the same, so quantity doesn't matter.
        
               | robocat wrote:
               | Returns are highly skewed.
               | 
               | If your prior is: exercise price and Fair Market Value
               | are equal, my bet would be that the shares are most
               | likely loser shares.
               | 
               | Winning shares are much more likely to have a fair market
               | value that exceeds the option exercise price.
               | 
               | The rules of the game are written by the winners!
        
             | jjav wrote:
             | > why wouldn't you buy preferential shares?
             | 
             | I'm left with the sense that this is a response to some
             | other post, not mine?
             | 
             | To be clear, I'm talking about scenarios where one would
             | join a startup as a regular employee. Not talking about
             | angel investing or anything like that.
        
               | robocat wrote:
               | I am just saying that common shares are extremely high
               | risk investments. When you start putting money into an
               | investment I believe you should aim to get the same risk
               | profile as other investors that are putting money in. If
               | exercising your shares is a trivial cost, then it doesn't
               | matter. If exercising shares costs a lot then it really
               | really matters.
               | 
               | Common shares have zero value until after the
               | preferential shares are in the money. i.e. buying common
               | shares is as risky as investing in call options.
               | 
               | Angel investing is extreme risk, call options are extreme
               | risk, and as a sweeping generalisation: common shares are
               | riskier than those. I'm only mentioning Angel investing
               | because we all know how risky that is, so it is a
               | baseline to compare against.
               | 
               | You answered JonChesterfield who's point was "here's some
               | tokens". Your reply is entirely sensible and you are
               | rightly saying those tokens can end up winning and you
               | explain a good strategy to get valuable tokens and gamble
               | some of your pot.
               | 
               | I am attempting to amplify JonChesterfield's comment,
               | perhaps I'm failing!
               | 
               | Aside: I really appreciate your comment and I am
               | commenting to help my own thinking. I have been trending
               | towards doing Angel investments which requires
               | understanding VC incentives. I'm past being an employee
               | so I'm not sure how relevant my comments are to anyone!
               | VCs and the VC ecosystem use the confusion between the
               | details of public market shares, common shares, and
               | preferential shares to the advantage of the VCs.
        
         | nilram wrote:
         | Any more, I'd rather they just gave me lottery tickets. My
         | payout rate has been the same.
        
         | tossandthrow wrote:
         | Tbh, I would never go below market rate in real money
         | indifferent to what equity deals I am provided. But a nice,
         | liveable, just above market rate salary + some stock. I don't
         | shy back from that.
        
       | theogravity wrote:
       | Surprised it didn't mention anything about AMT, which may prevent
       | one from exercising because they can't afford the tax hit from
       | the spread.
        
       | mancerayder wrote:
       | Is it that bad? I'm on a relatively reduced salary due to ISOs in
       | a company that wants to exit in the next couple of years, and a
       | stock valuation that keeps going up (per audits) in the last
       | years. It's also still expanding quickly. The company even did a
       | raise and let some of us sell a percentage of our shares to the
       | private buyer.
       | 
       | This is not Silicon Valley, but a fintech. Given I have not only
       | my time but 10s of k of my money tied up in options due to strike
       | price going up with each grant, in what way am I risking getting
       | screwed?
       | 
       | In the comments here, it seems like I have a 60+ percentage
       | chance of getting screwed through a dilution or other. However it
       | doesn't feel that way.
       | 
       | What should I be on the lookout for? The Paperwork is dozens of
       | pages long and I'm not an attorney.
        
         | fragmede wrote:
         | I'm not an attorney either. The best way to answer the question
         | is to find one that specializes in this arena, and ask them,
         | rather than believe anything you read on the Internet, or from
         | an LLM. Still, the whole thing could just go to zero. The
         | finteching doesn't work out and the company and thus your
         | options become worth zero. I hope that doesn't happen for you,
         | but before dilution, you have up look at that as a very real
         | possibility. Something could pivot out from under you and it
         | could just stop working and being worth anything.
         | 
         | Once you've stared that beast in the face, yeah, dilution is a
         | thing that could happen, but it's not in anyone's interest to
         | screw you over. If you get screwed over by your board, people
         | are going to know, and not want to work with those people ever
         | again. So dilution absolutely happens, but you just have you
         | hope you're not gonna get screwed over. There's no legal
         | guarantee that you won't though, so that's why the common
         | advice is that that options are worth $0, until they aren't. So
         | you have to look at options as a lottery ticket and ask how
         | much you like the work and how much you like your coworkers,
         | how much you like what the company does, and can you live off
         | the pay you do get.
        
         | pyrophane wrote:
         | Well, for the most part you agreed to your employer's stock
         | plan when you were granted options, and so you are subject to
         | whatever is in there but there isn't a lot you can do about
         | that since you would have already signed it a while back.
         | 
         | I would just refer to an attorney regarding anything would
         | modify your shares or the agreement you already signed, because
         | those things can't be arbitrarily modified without your
         | consent.
         | 
         | Also, the most common way employees get "screwed" is when the
         | company underperforms and has to raise money on bad terms, but
         | there isn't much you can do about that.
        
       | neilk wrote:
       | There is no discussion of how the employees are the last to be
       | paid, after founder class shares and investor liquidation
       | preferences are settled.
       | 
       | Borders on misinformation to tell people that owning x% in shares
       | equals x% of liquidity event. Even many founders end up with very
       | little to show from an acquisition.
        
         | pyrophane wrote:
         | I don't think founders typically get liquidation preference
         | like VCs do, but correct me please if I'm wrong.
        
       | seanhunter wrote:
       | An article about startup employee stock options that doesn't
       | mention the effect of liquidation prefs and only mentions
       | dilution extremely briefly is really missing a huge amount of
       | what anyone needs to actually value stock options. On a quick
       | scan this doesn't look terrible [1], although it's focussed on
       | the founder's perspective rather than the employee's.
       | 
       | [1] https://www.joinarc.com/guides/liquidation-preferences
        
       | entangledqubit wrote:
       | I would avoid this guide. I don't even see mentions about
       | dilution and cap tables, let alone preference and a bunch of
       | other risks.
       | 
       | If you need a solid guide, I usually point at the Holloway Guide
       | To Equity Compensation but I'm annoyed that it looks like they
       | started charging for it (probably still worth both the time and
       | money). The preview is worth checking out. That being said, I
       | think there are a bunch of other aspects that aren't captured.
       | 
       | I was under the impression that founders/management generally
       | don't give any company specific guidance in order to not be on
       | the hook for anything that may be construed as guidance or
       | promises.
        
       | siliconc0w wrote:
       | Startups are great when you're looking for a fast-paced high-
       | trust environment where you're going to be given a lot of
       | responsibility and will be able to grow your skillset. From a
       | financial perspective, they're terrible unless you're an early
       | employee or possibly a very senior/exec hire. Rarely companies
       | might offer things like longer exercise windows but even then
       | your options can become worthless even in an unlikely successful
       | exit due to dilution/liquidation-prefs.
        
       | surfingdino wrote:
       | It's worth pointing out that this post is written from the point
       | of view of a US startup. If you are in the UK, just say no to
       | stock options and ask for a salary that matches the market. UK
       | startups keep on trying to get people to work for less with the
       | promise of stock options despite there being little recent
       | evidence of UK startups IPO-ing. I got screwed on startup stock
       | options in the past, but not as badly as people who invested 5+
       | years of their lives into the company. The founder got enough to
       | not have to work for the rest of his life, but the employees got
       | zero pennies when the business was sold to competition. Stock
       | options are not even a gamble, they are an IQ test, if you accept
       | them you have failed.
        
       | nickjj wrote:
       | I'm surprised the post doesn't mention a specific type of risk
       | which is out of your control.
       | 
       | I'm not well versed in options lingo, is there something to
       | describe this scenario?
       | 
       | You join with a very low strike price, such as $0.05 and get a
       | lot of shares, let's say 200k to keep the math easy. At that
       | strike price the value on paper is $10,000.
       | 
       | Then a liquidity event occurs before your options vest and now
       | instead of 200k shares @ $0.05 you have 3,333 shares at $3.00
       | because the valuation of the company changed. You still have
       | $10,000 in options.
       | 
       | The issue now is you've taken a huge loss in the multiplier
       | effect. Having a stock go from $0.05 to $1 is a 20x jump. Hitting
       | that would yield $200,000 in value.
       | 
       | But the odds of $3 turning into $60 is so much lower, but that's
       | what you would need the stock to hit to yield the same return in
       | the end.
       | 
       | In the end, over time you tend to get less stocks at a higher
       | adjusted strike price with no real-world opportunity to exercise.
       | Sometimes even if you have vested options you can only exercise a
       | single digit percentage of your total shares so the total cash-
       | out value is the equivalent of 1 day's worth of pay even after
       | years of vested options.
        
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