[HN Gopher] Stripe sets one-year timetable to decide on going pu...
       ___________________________________________________________________
        
       Stripe sets one-year timetable to decide on going public
        
       Author : amitparikh
       Score  : 118 points
       Date   : 2023-01-26 16:18 UTC (6 hours ago)
        
 (HTM) web link (www.wsj.com)
 (TXT) w3m dump (www.wsj.com)
        
       | rvz wrote:
       | Maybe they should have IPO'd or directly listed in 2019 at the
       | very peak when everyone else was rushing to the exit as I said
       | before [0]. Of course this is also not in hindsight either. [1]
       | 
       | Seems like they now don't want to wait anymore and just unload
       | their shares into the market and especially onto retail
       | investors.
       | 
       | [0] https://news.ycombinator.com/item?id=32567217
       | 
       | [1] https://news.ycombinator.com/item?id=20993919
        
         | cschep wrote:
         | you know what they say.. hindsight is 2019.. :D
        
         | fragmede wrote:
         | hindsight is 20/20
        
         | Province1108 wrote:
         | Not really when the terms of private financing during the bull
         | run were very generous for valuations and terms.
         | 
         | There are big downsides to being public, including all the
         | regulatory requirements and pandering to institutional
         | investors.
         | 
         | Now the bull market is over and private money is tighter, they
         | don't really have a choice but to raise money publicly.
        
       | neonate wrote:
       | https://archive.ph/GqSBm
        
       | TekMol wrote:
       | It's interesting that there is so much technology and third party
       | business involved in the process of moving value.
       | 
       | - Visa has a market cap of $463B
       | 
       | - Mastercard $362B
       | 
       | - PayPal $90B
       | 
       | - Block $48B
       | 
       | Could it theoretically all be automated?
        
         | fragmede wrote:
         | I don't think visa is doing it by hand and pencil and paper
         | though, and the value in those companies is that they're taking
         | bioff the top of every transaction that runs on their rails. so
         | it's already automated too a huge degree, it's just that
         | automation is what _gives_ those companies that market cap
        
           | TekMol wrote:
           | But what is the value they provide, which justifies their
           | earnings and therefore market cap?
        
             | fragmede wrote:
             | by being the digital rails. without visa/mc, all you have
             | in your wallet is a piece of useless plastic. there's huge
             | value in the convenience of not having to use cash, and
             | then the rewards programs on top of that.
        
               | treis wrote:
               | Sure but that's not why Visa/MC are worth that much.
               | They're worth that much because they're a duopoly that
               | can dictate prices.
        
               | mbesto wrote:
               | > that can dictate prices
               | 
               | Prices that are capped by the government:
               | 
               |  _The Fed's 2011 rules capped fees at 21 cents plus five
               | basis points of each transaction, and also allowed an
               | additional one cent fee per transaction for fraud
               | prevention, where applicable._ [0]
               | 
               | [0] - https://news.bloomberglaw.com/antitrust/biden-
               | takes-on-visa-...
        
               | treis wrote:
               | That's for debit cards only. Which Visa/MC have knee
               | capped with their monopoly power so it doesn't really
               | matter. Actually helps as a distraction
        
         | timerol wrote:
         | No. (Channels patio11) As a society we have decided to delegate
         | a bunch of responsibilities to the companies that move money.
         | The most notable one is fraud protection. The companies that
         | make this much money do so by pretending that a transfer of
         | money is a clean, simple, and absolute thing. In reality it is
         | messy, reversible, and fraud-prone. Being able to transfer $1B
         | dollars as easily as you are able to transfer $1 would be a
         | failure of the system, not a feature.
        
           | TekMol wrote:
           | I have been paying and being paid for decades now, and I have
           | never involved a payment processor in a dispute I had with
           | the other side.
           | 
           | If arbitration is the reason these companies exists, it seems
           | like bad deal.
           | 
           | Maybe they sell an illusion?
        
             | changoplatanero wrote:
             | Maybe your credit card number was stolen without your
             | knowledge and they took care of it for you without you even
             | being aware
        
               | willcipriano wrote:
               | They took care of it for themselves, when someone commits
               | fraud it isn't your problem because they used your name
               | to do it.
               | 
               | Imagine if you were defrauded for a few hundred bucks by
               | someone claiming to be a big celebrity. You probably
               | wouldn't even be able to get into contact with the actual
               | person, let alone have them jump through a bunch of
               | hoops, spend time on hold with your staff or go to the
               | post office to send you copies of documents. They
               | wouldn't bother to respond to you, they have no
               | obligation to, whatever happened had nothing to do with
               | them.
        
               | abigail95 wrote:
               | That would be whoever made the cards fault. We don't give
               | credit for cleaning up your own mess, that's the minimum
               | standard for engaging in a beneficial relationship.
               | 
               | It's not a value proposition from gmail that you can't
               | access my inbox just from knowing my address.
               | 
               | I can't believe you can be a $400B company and the value
               | comes from stopping fraud that you enabled by your own
               | product design.
        
               | TylerE wrote:
               | Much of the fraud is merchants defrauding their
               | customers.
        
               | ddorian43 wrote:
               | Nah.
        
             | djbusby wrote:
             | I've used banks and cards to help resolve fraud. Rarely,
             | but I love it.
             | 
             | And now the bank pushed me to use Zelle - which has zero
             | protection.
        
               | lxgr wrote:
               | > [...] bank pushed me to use Zelle - which has zero
               | protection.
               | 
               | Also channeling patio11 [1]: This is actually a pretty
               | interesting ongoing experiment as to whether banks can
               | opt out of Regulation E.
               | 
               | [1]
               | https://twitter.com/patio11/status/1500993875627761666
        
               | jchw wrote:
               | To be fair, the trade-off is that there aren't any fees
               | and it's nearly instantaneous. For the type of
               | transaction similar to handing someone you know a wad of
               | cash, it seems pretty good.
        
             | lxgr wrote:
             | > I have been paying and being paid for decades now, and I
             | have never involved a payment processor in a dispute I had
             | with the other side.
             | 
             | Have you considered that the _possibility_ of disputes and
             | the existence of a framework for resolving them is part of
             | the reason for that?
        
             | darkerside wrote:
             | Countering your own anecdata with my own, I have. To the
             | tune of $5,000+.
        
             | pchristensen wrote:
             | "I have never been owned by another person, so there is no
             | need for a law against slavery."
             | 
             | The world is full of services, valuable, difficult to
             | provide services, that a given person will never consume.
             | Doesn't mean no one else does.
        
         | rglover wrote:
         | Yes, with Bitcoin.
        
           | methodical wrote:
           | And by using Bitcoin to automate all these transactions you
           | get a bunch of very cool features such as constantly being at
           | risk of losing your life savings due to phishing, scamming,
           | hacking, etc., etc., etc. unless you store a hard wallet in
           | your intestines and memorize the recovery words (better hope
           | you don't forget any or your life savings is gone!). The cool
           | thing about all of this is that it's a _feature_ of Bitcoin
           | to be able to irreversibly lose your life savings, without
           | any ability to recoup your losses.
           | 
           | All of this to say that Bitcoin is obviously the way forward
           | for global transactions, despite the fact it processes
           | transactions as slow as molasses and the only way to make it
           | faster (Lightning Network) is to sacrifice the checks and
           | balances that maxis praise as the hallmark of Bitcoin lol
        
             | rglover wrote:
             | > And by using Bitcoin to automate all these transactions
             | you get a bunch of very cool features such as constantly
             | being at risk of losing your life savings due to phishing,
             | scamming, hacking, etc., etc.
             | 
             | All lies.
             | 
             | > unless you store a hard wallet in your intestines and
             | memorize the recovery words (better hope you don't forget
             | any or your life savings is gone!)
             | 
             | Lies. Just write them down and store them securely. You can
             | memorize them if you like. It's also wise to store multiple
             | physical copies in various locations to avoid this exact
             | scenario.
             | 
             | > The cool thing about all of this is that it's a feature
             | of Bitcoin to be able to irreversibly lose your life
             | savings, without any ability to recoup your losses.
             | 
             | Yes, you can't be utterly careless (and I'm not sure what
             | the argument is for wanting to be).
             | 
             | > the only way to make it faster (Lightning Network) is to
             | sacrifice the checks and balances that maxis praise as the
             | hallmark of Bitcoin
             | 
             | Yes, which makes sense for small transactions between
             | trusted parties. Large transactions can and should be done
             | on-chain (also with trusted parties).
             | 
             | --
             | 
             | I'll continue to listen to the signal [1], not the noise.
             | What makes me happiest is that the people who deserve to
             | win the most will win over the people who deserve it the
             | least. It will be the greatest wealth transfer humanity has
             | ever seen and it won't require any violence or coercion.
             | 
             | [1] https://twitter.com/LightningTipB0t/status/161501479879
             | 79919...
        
               | methodical wrote:
               | > All lies.
               | 
               | Doesn't bother to point out what part of it was a lie
               | (because it isn't a lie)
               | 
               | > Lies. Just write them down and store them securely.
               | 
               | Welcome to the future of finance, make sure you don't
               | lose your seed phrases written down on paper (it's the
               | future, trust me bro)
               | 
               | > Yes, you can't be utterly careless
               | 
               | Contradicts saying that I was lying that you can lose
               | your life savings due to phishing, scamming, or hacking,
               | and that if you lose your seed phrases and can't access
               | the wallet then your digital doubloons are gone forever
               | 
               | etc.
        
               | rglover wrote:
               | > Doesn't bother to point out what part of it was a lie
               | (because it isn't a lie)
               | 
               | This "constantly being at risk of losing your life
               | savings due to phishing, scamming, hacking, etc." is a
               | lie. There is no inherent property of Bitcoin that makes
               | you vulnerable to these. Any vulnerability in those
               | regards is an individual issue, just like with the
               | current system. You could mitigate those away with paid
               | services under a Bitcoin standard (which is great because
               | you could actually _pick_ the vendor you thought could do
               | the job best).
               | 
               | > Welcome to the future of finance, make sure you don't
               | lose your seed phrases written down on paper (it's the
               | future, trust me bro)
               | 
               | Perhaps you prefer steel? https://www.amazon.com/Safe-
               | Seed-Stainless-Recovery-Passphra...
               | 
               | > Contradicts saying that I was lying that you can lose
               | your life savings due to phishing, scamming, or hacking,
               | and that if you lose your seed phrases and can't access
               | the wallet then your digital doubloons are gone forever
               | 
               | Fair enough. This is where an exchange comes in. You
               | still have the option to trust a third-party to hold your
               | Bitcoin if you wish. But of course, that comes with its
               | own risks, just like trusting a bank (which can only ever
               | guarantee up to $250K worth of your money under FDIC).
        
               | ZephyrBlu wrote:
               | I'm pretty favourable towards crypto, but it is
               | absolutely an inherent property of blockchains.
               | 
               | The whole point is that it's immutable and transactions
               | are not reversible. That means users are susceptible to
               | losing their money with no recourse.
               | 
               | Seed phrases are also a pain in the ass. No one wants to
               | deal with that, and average consumers would absolutely
               | lose/forget/misplace them and lose access to their
               | wallets.
               | 
               | The risk of ruin in crypto is ridiculously high compared
               | to traditional finance.
        
               | TylerE wrote:
               | This sort of vague handwaving of valid concerns is the
               | definition of noise.
        
               | methodical wrote:
               | Almost like handwaving is the only way to disregard any
               | of the real concerns people bring up about Bitcoin or
               | crypto because there's not really any good way to dispel
               | them with much logical proof.
        
               | rglover wrote:
               | I responded directly to what was said. There's no
               | handwaving, you just don't like my response. Read my
               | other responses in this thread, too.
        
               | TylerE wrote:
               | "All lies" is not a response.
        
               | rglover wrote:
               | That was only part of the response.
        
             | abigail95 wrote:
             | It's a different kind of cash (like banknotes). It has
             | different security tradeoffs because the owner is the
             | custodian and you aren't paying a chain of intermediaries.
             | 
             | It's not a feature of cash that it can be stolen, every
             | object can be stolen. The distinctive attribute is
             | transactions are public and immutable.
             | 
             | A car can be driven by its owner anywhere they like. If
             | someone described a car to you as a suicide box you can
             | crash and die in - you might say yes, the fact that cars
             | can be driven freely by their owners means you might drive
             | into someone else. But that's a consequence of the feature,
             | not the feature itself.
        
               | methodical wrote:
               | The difference of course between all of the rubbish that
               | crypto/Bitcoin is (since they are, at the end of the day,
               | in the same boat), is that by entrusting central parties
               | to handle financial transactions in our traditional
               | financial systems we have methods by which we can reverse
               | transactions, whereas in any blockchain system there is
               | no real authority, by design, so any stolen assets are
               | lost forever. There aren't security "tradeoffs", because
               | there is not a way in which any blockchain based currency
               | is any more secure than current finances, outside of the
               | fact that no bank or government entity could take your
               | digital beanie babies because they don't have the token,
               | which isn't an issue in traditional banks either unless
               | you're a criminal for the most part. And in order to get
               | this "advantage" of blockchain, you have to completely
               | remove its ability to be used as a currency since for any
               | amount of crypto or Bitcoin to be useful in the real
               | world it almost always has to be converted back into
               | fiat, once again centralizing it. The whole concept is
               | extremely flawed, hasn't really gained any ground outside
               | of FOMO'ers, and will likely die out again soon,
               | thankfully.
        
               | asterix_pano wrote:
               | - you can use an escrow account to reverse the
               | transaction if needed - having full ownership of your
               | money and it being censorship resistant (depending on the
               | crypto) is certainly a plus if you don't fully trust your
               | government. - the conversion to fiat is depending on
               | adoption: the more adoption there is, the less necessary
               | that would be. - you can decide to wire your money 24/7,
               | internationally, instantly and with no fees (with the
               | right crypto)
               | 
               | Overall you get more control of your money. If you think
               | of money as just another kind of information, it's normal
               | to expect it to evolve in the digital age we are living
               | in.
        
           | lxgr wrote:
           | Does Bitcoin support dispute resolution (i.e. chargebacks)
           | yet?
        
             | rglover wrote:
             | It doesn't need to. Transact with vendors you actually
             | trust who have a track record you can verify (which
             | necessitates people being trustworthy to earn business--
             | unlike our current economic order).
        
               | kasey_junk wrote:
               | And on the vendor side? Are you suggesting that either
               | all sellers know a) the credit worthiness of their
               | customers or b) don't extend any credit?
               | 
               | Either one seems like a major downside for the seller.
        
               | rglover wrote:
               | > Are you suggesting that either all sellers know a) the
               | credit worthiness of their customers or b) don't extend
               | any credit?
               | 
               | That's up to the business owner, but considering the
               | utter destruction its done to the world I would say most
               | businesses should not extend any credit.
               | 
               | The nice thing about Bitcoin is it's a transaction layer
               | and people can build services on top of it. Someone could
               | start a guarantor business that other businesses pay to
               | verify creditworthiness. They do that already now, the
               | difference being that it's a completely dark system
               | controlled by people with no incentive to fairly or
               | accurately represent your worthiness.
        
               | lxgr wrote:
               | > Bitcoin is it's a transaction layer and people can
               | build services on top of it
               | 
               | The transaction layer is arguably the least interesting
               | service the credit card and other incumbent
               | transaction/payment networks provide.
               | 
               | Deciding _whether_ to move money, and possibly whether to
               | move it back, is where the value is created.
        
               | rglover wrote:
               | > The transaction layer is arguably the least interesting
               | service the credit card and other incumbent
               | transaction/payment networks provide.
               | 
               | It isn't until you can't transact over it because your
               | government blocked it or received an international
               | sanction that prevents you, an innocent citizen from
               | transacting. Or, if you reside in a country where that
               | network does not exist.
               | 
               | > Deciding whether to move money, and possibly whether to
               | move it back, is where the value is created.
               | 
               | Incorrect. The ability, not the decision, is where the
               | value resides. I can decide all I want that I'd like the
               | bank to send $20K to someone overseas for me, but that
               | likely means jumping through several hoops to do it. With
               | Bitcoin, I can just _do it_.
        
               | lxgr wrote:
               | How would that not lead to the inevitable concentration
               | of economic activity in a few trusted platforms?
               | 
               | Today, I can shop at pretty much any merchant on the web,
               | under the reasonable expectation that my bank will file a
               | dispute for me if the merchant makes a run for it and I
               | never receive any goods or services. Even in case of
               | merchant bankruptcy, I'm not exposed to any risk.
               | 
               | In a world of non-reversible payments, I'd probably stick
               | to Amazon exclusively. That seems pretty bad for
               | small/new/independent merchants.
        
               | rglover wrote:
               | > How would that not lead to the inevitable concentration
               | of economic activity in a few trusted platforms?
               | 
               | Because it would force people to be honest in order to
               | eat. Economic activity as a whole would become a lot more
               | transparent because people will avoid hiring you or
               | buying from you if you have a bad reputation. The inverse
               | is also true, rewarding the business owner who invests in
               | quality and customer service.
               | 
               | > if the merchant makes a run for it
               | 
               | Again, this is a discernment issue not a systems issue.
               | In that particular case, you can set up an escrow
               | transaction that only releases funds if the transaction
               | goes through. EBay has already proven, too, that most
               | people are honest by default so this is a non-issue.
               | 
               | > In a world of non-reversible payments, I'd probably
               | stick to Amazon exclusively. That seems pretty bad for
               | small/new/independent merchants.
               | 
               | That's a personal choice.
        
               | lxgr wrote:
               | > [...] it would force people to be honest in order to
               | eat.
               | 
               | But how do I detect honesty in first interaction with an
               | unknown party?
               | 
               | > [...] people will avoid hiring you or buying from you
               | if you have a bad reputation [...]
               | 
               | As a merchant, what if I have _no_ reputation? How do I
               | ever get my first customer?
               | 
               | > EBay has already proven, too, that most people are
               | honest by default [...]
               | 
               | ...on a centralized platform that can arbitrate trust!
        
               | rglover wrote:
               | > But how do I detect honesty in first interaction with
               | an unknown party?
               | 
               | It should be obvious. The guy who shows up to your intro
               | meeting well-dressed, prepared, etc with references is
               | going to be preferable to the guy who shows up smelling
               | like vodka in tattered clothes.
               | 
               | > As a merchant, what if I have no reputation? How do I
               | ever get my first customer?
               | 
               | The same way you do under the current system. Go work for
               | someone else to build up credentials/experience, or,
               | offer to do stuff for free in exchange for referrals and
               | testimonials.
               | 
               | > on a centralized platform that can arbitrate trust!
               | 
               | Can, but often doesn't need to.
        
               | lxgr wrote:
               | > The guy who shows up to your intro meeting [...]
               | 
               | Do you regularly hold in-person intro meetings for
               | ordering sub-$100 items online?
               | 
               | > Go work for someone else to build up
               | credentials/experience, or, offer to do stuff for free in
               | exchange for referrals and testimonials.
               | 
               | And then passport it to my own store how, exactly? "Trust
               | me, I'm honestseller897 on Amazon/eBay"?
               | 
               | >> on a centralized platform that can arbitrate trust!
               | 
               | > Can, but often doesn't need to.
               | 
               | The fact that it does, when required, is the reason for
               | rarely needing to.
        
       | djyaz1200 wrote:
       | Is there any way to buy stock from employees now?
        
         | drexlspivey wrote:
         | There are secondary markets for private companies' shares (like
         | EquityZen) but I believe you need to be an accredited investor
         | to participate
        
         | paxys wrote:
         | There have always been ways. Find an employee and make them an
         | offer. Or use one of the many private marketplaces.
        
         | umeshunni wrote:
         | EquityZen had an offer to buy last week at a $75B valuation /
         | $32 per share.
        
           | JumpCrisscross wrote:
           | > _EquityZen had an offer to buy last week at a $75B
           | valuation / $32 per share_
           | 
           | That's wildly off market, like 30%+. That's high, even for a
           | retail platform.
        
             | magneticnorth wrote:
             | What do you mean by off market? Are you saying the value
             | should be 30%+ higher or lower, and how did you get that?
             | 
             | Obviously the usual kind of market isn't applicable here,
             | so I'm curious what you mean.
        
       | babl-yc wrote:
       | I assume this is in part due to the 10 year expiration of ISOs?
       | Stripe was founded in 2010.
        
       | bbq wrote:
       | Importantly they said within a year they will go public OR do a
       | private market transaction to make employees liquid
        
         | Aqua_Geek wrote:
         | That's a LONG time (in total) for employees to wait for
         | liquidity. Yes, they likely provided some opportunities for
         | early employees to liquidate some of their holdings, but it's
         | got to suck to sit on that much funny money for so long.
        
           | msoad wrote:
           | An IPO will be longer. With the locked out period it will be
           | more than a year
        
             | makestuff wrote:
             | Not necessarily if they do a direct listing.
        
               | khazhoux wrote:
               | A direct listing would be very unfair to the banks that
               | have patiently waited years to take a multi-billion-
               | dollar chunk of Stripe's upside in exchange for setting
               | the IPO price (integer between 20 and 50).
        
               | mercedsownboy wrote:
               | Thank you for a great chuckle
        
               | htrp wrote:
               | The level of shade is about as high as the expected ipo
               | pop
        
           | preinheimer wrote:
           | They've had several options for employees to liquidate some
           | of their holdings before now. They've generally only been
           | open to current employees, but one a few years ago was also
           | open to past employees.
        
             | clintonb wrote:
             | Those offerings are only for options holders. RSUs cannot
             | be traded; otherwise, every RSU holder has to pay taxes.
        
               | scarface74 wrote:
               | As someone who only has dealt with public companies, how
               | is that different from my having to pay taxes when my
               | RSUs vest?
        
               | a_t48 wrote:
               | This happened to me this year with another company. They
               | opened up the ability to sell back RSUs, and a chunk of
               | them got sold to pay for taxes.
        
               | lbotos wrote:
               | I assume Stripe is giving out "Double Trigger RSUs" then?
               | https://blog.pragmaticengineer.com/equity-for-software-
               | engin...
               | 
               | Otherwise people are getting taxed now anyway if they are
               | getting RSUs at a private Stripe, right?
        
               | calr wrote:
               | Noob question that I am sure is answered many times. What
               | are the catalysts for a private company switching from
               | options to RSUs (double trigger). In my previous role I
               | got RSUs (double trigger), but now at a much smaller
               | startup I have an option package. As an employee RSUs are
               | a bit easier to make sense of, but both are equity
               | instruments at the end of the day. When, and why does
               | that transition happen?
               | 
               | Edit this is answered fairly well here:
               | https://www.parkworth.com/blogs/pre-ipo-tech-giants-
               | using-do.... The TLDR is SEC rules and limited perceived
               | upside of options (although I imagine that could be
               | solved via a lower strike price).
        
               | chimeracoder wrote:
               | > What are the catalysts for a private company switching
               | from options to RSUs (double trigger).
               | 
               | For employees at very early companies that are going the
               | venture route, ISOs are a no-brainer. The company is
               | small enough that the strike price isn't too onerous, the
               | company is too small to hit up against the IRS limits,
               | and they provide pretty good tax treatment under the
               | assumption that the company will grow massively in value
               | - like, 100,000x - which is the the optimistic case that
               | everyone wants to optimize for.
               | 
               | For employees at late stage companies (e.g. last funding
               | round before IPO), ISOs are a rough deal. The strike
               | price is large, so the only people who can afford to
               | exercise them before a liquidity event are people who are
               | already independently wealthy. The tax benefits are also
               | still present, but smaller, because the expectation is
               | that the company might grow 10x in valuation, but not
               | 100x or 100,000x (most $100M companies are not going to
               | grow to $10 trillion in valuation).
               | 
               | RSUs avoid that problem, by requiring zero cash up-front,
               | in exchange for less favorable tax treatment in the
               | "company grows 100x-100,000x" case - which is fine,
               | because that's less relevant.
               | 
               | Of course, the billion dollar question is where the
               | inflection point happens - when do RSUs become a better
               | deal than ISOs? There's no universal answer to that, and
               | some of that depends on specifics of the company, and
               | some of that also depends on who you ask (certain people
               | will benefit more than others from the switch at
               | different points, so it depends on how much the company
               | is weighing each of those [metaphorical] stakeholders).
               | 
               | ISOs also have one other advantage for companies: because
               | they have to be exercised within 90 days of departure, a
               | large portion of ISOs that are granted will never
               | actually be exercised (the employee will choose to leave
               | them unexercised, either because they don't have the
               | money to pay for the exercise price + taxes or because
               | they don't want to). So every option granted is <1 share
               | actually given up (in expectation), allowing the company
               | to grant bigger compensation packages (because some
               | portion of those will not actually be used, and can
               | therefore be reallocated to someone else).
               | 
               | With RSUs, every RSU granted is 1 share actually given up
               | (except in the case where the RSUs expire, which makes
               | the company look bad).
        
               | calr wrote:
               | Thanks for the in depth write up. Makes a lot of sense!
        
               | arcticbull wrote:
               | There's also usually a switch from ISO to NSO somewhere
               | down the line, often fairly early. NSOs aren't capped at
               | a 90 day post-termination exercise window. Some companies
               | have extended the window to as much as 7 years -
               | Pinterest comes to mind. There is _a_ cap, but it 's
               | closer to the RSU cap than the ISO cap.
               | 
               | The progression is usually:
               | 
               | - Founders get shares with a re-purchase option for
               | vesting. The company exercises the option if you leave
               | before vesting ends to take back your un-vested shares.
               | 
               | - Next ~100 people get ISOs.
               | 
               | - Next ~2000 get NSOs.
               | 
               | - Then, double-trigger RSUs until the company goes
               | public.
               | 
               | - Then, single-trigger RSUs.
               | 
               | I agree with your general assessment. The difference
               | between options and RSUs usually comes down to upside
               | potential. An option is worthless at grant time (by law,
               | it usually has to be issued at the 409(a)) and it's just
               | the right to buy company shares. If you're buying the
               | shares at the current price, there's no value in that.
               | Options only gain intrinsic value of _future_
               | appreciation in the underlying equity past your grant
               | date.
               | 
               | On the other hand RSUs are shares of the company, so they
               | are worth at grant whatever a share of the company is
               | worth.
               | 
               | An option with a $10 strike price to buy shares of a
               | company whose 409(a) is $11 has an intrinsic value of $1.
               | An RSU of a company whose 409(a) is $11 has an intrinsic
               | value of $11.
               | 
               | Companies generally, in my experience, give you about 3X
               | as many options as they would shares for the same role.
               | Give or take. Companies usually switch from options to
               | RSUs when they think that growth in the stock price is
               | going to slow down - [edit] (and when they're hiring
               | people with a higher aversion to risk!)
        
               | ywain wrote:
               | Correct. Stripe gave out stock options until around 2016
               | or 2017, then switched to double-trigger RSUs.
        
               | jcdavis wrote:
               | it can be done (via eg waiving the 2nd exit trigger and
               | converting to common) but is pretty complicated
        
       | mguerville wrote:
       | Interesting timing, wouldn't think it's optimal given macro
       | conditions, but perhaps they don't want to wait however long
       | it'll take to get back to the frothy markets
        
         | shawnz wrote:
         | It's because the earliest RSUs they issued are expiring this
         | year: https://www.theinformation.com/articles/stripes-early-
         | stock-...
        
           | bgorman wrote:
           | Wouldn't it be good for the company to let these RSUs expire?
           | How does it benefit the company to make sure these exercise?
        
             | Jakawao wrote:
             | Employees tend to leave when a major portion of their
             | compensation disappears.
        
             | Blackthorn wrote:
             | If they don't let them exercise, the existing employees
             | will rightly see it as funny money and not actual
             | compensation. They won't be employees for much longer after
             | that.
             | 
             | Especially since Stripe has steadfastly refused to go
             | public so far...
        
             | ball_of_lint wrote:
             | Equity compensation and what it's valued at is a big factor
             | in choosing to work at Stripe. If they start letting RSUs
             | expire, it will make ~everyone value their equity
             | significantly less; Stripe would likely have significant
             | difficulties finding and retaining talent.
        
             | [deleted]
        
             | encoderer wrote:
             | In some ways, yes, but I think if you game it out, you see
             | how the company loses in a number of ways. First,
             | repetitional risk. Second, it's likely that a liquidity
             | provider would emerge who could offer, basically, to buy
             | call options from individual holders for enough premium to
             | cover the taxes due on exercise. (Stripe would not want an
             | unaffiliated 3rd party accumulating a large position)
        
               | winphone1974 wrote:
               | Transfer and using them as collateral are typically
               | prohibited explicitly in the agreement, so I'd be
               | surprised if this could happen
        
               | encoderer wrote:
               | Then call it a promisary note.
        
             | chippiewill wrote:
             | It's not in the company's interest to piss off employees
             | who can't afford to exercise their options without being
             | able to sell them.
             | 
             | My company recently got bought by a privately owned
             | company. Because of the ownership structure of the
             | purchasing company we weren't allowed to exchange our
             | options or let new ones vest so my company's board approved
             | cancelling and reissuing everyone's options with an
             | acceleration clause so they'd completely vest at completion
             | so we'd all get a full payout. They did this because they
             | knew if they didn't that there would be an exodus of
             | employees before the purchase went through.
             | 
             | Employees represent a large % of the value of the company,
             | if they all leave you just have a bunch of tech that no one
             | else knows how to maintain or use. Institutional investors
             | typically have such a large proportion of the shares that
             | it's worth it to them to not just screw over employees
             | because the employee sticking around and keeping shares is
             | worth more than they'd save.
        
           | Aqua_Geek wrote:
           | They're options that are set to expire, not RSUs. Yes, the
           | employees could exercise them to prevent them from expiring,
           | but then Uncle Sam comes to collect his dues. And that's
           | where illiquidity burns you.
        
             | chimeracoder wrote:
             | > They're options that are set to expire, not RSUs.
             | 
             | Both options and RSUs are required by law to have
             | expiration dates. And it's plausible that either or both
             | could have expiration dates within the next 12 months.
        
             | kasey_junk wrote:
             | Double trigger rsu's in private companies also expire and
             | holders of those have no option even to eat the taxes in
             | that case. They just lose them.
        
               | Aqua_Geek wrote:
               | Good point. I forgot about that.
        
             | [deleted]
        
       | mkl95 wrote:
       | TIL Stripe have lowered their internal valuation from $95bn to
       | $63bn since mid 2022.
        
         | paxys wrote:
         | Considering so many public, profitable tech companies saw their
         | valuations go down by 50-70% in that same period, that still
         | seems too little of a cut.
        
           | agloeregrets wrote:
           | This assumes Stripe is not outperforming expectations. .which
           | seeing the Amazon deal....
        
             | objclxt wrote:
             | It's unclear that the Amazon deal is outperforming
             | expectations versus a quid pro quo on AWS hosting.
        
               | agloeregrets wrote:
               | Either is an upside. That's a huge contract that any
               | payment processor would kill for.
        
           | bdcravens wrote:
           | Public companies have more external influences on their
           | valuation. It's not like they literally lost 50-70% of their
           | intrinsic value, only what the market with the associated
           | psychology says they are worth. Private companies can stick
           | closer to that intrinsic value.
        
             | mathattack wrote:
             | Intrinsic value involves discounting future cash flows.
             | With rates up that should punish Stripe similar to the rest
             | of the market.
        
             | paxys wrote:
             | > Private companies can stick closer to that intrinsic
             | value
             | 
             | It's normally the opposite. Public markets are a lot better
             | at judging intrinsic value than a handful of VCs. Every
             | single private company out there is either wildly over or
             | under-valued, more so at earlier stages.
        
               | TuringNYC wrote:
               | Not to mention, VC valuations have all sorts of hidden
               | stipulations such as liquidity preferences which skew
               | headline private valuation numbers unnecessarily high.
               | Public markets have a full view of the cap table and can
               | better evaluate price w/o hidden tricks.
        
               | jjeaff wrote:
               | Plus, all VC investors have every incentive to juice the
               | valuation after they have bought in.
               | 
               | They don't have short sellers seeking out reasons to tank
               | it like the public markets do.
        
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