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

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

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

First, dilution should only be happening at funding events, not every time a new senior staff person is hired, and second the dilution should affect everyone equally— founders, execs, angels, VCs.

It's super unfair to give an employee "x shares" that turn out on exit to be shares of a fixed pie that is different from the one the investors have their shares in.

When the option pool is created that is the dilutive event, so new employees getting their grants doesn't result in current employees being diluted, because the entire pool was already taken into account.

But that’s not true. An options pool containing shares owned by the company is the same from a “how much of the company do I own” perspective as unissued or even uncontemplated shares.

The only real advantage to the options pool is ease of management of the shares. There’s a lot of paperwork around issuing new shares you don’t want to do it every time you hire a programmer. And I guess you could argue that telling people the pool exists lets them not be surprised by the future dilution when they’re issued. But the pool itself hasn’t diluted anyone.

Dilution is created by increasing the number of shares held by the company’s owners. Actions like issuing shares from a pool (or the inverse, buyback or cancellation of grants) affect every shareholders relative dilution.

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

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

The people.

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

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

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

What happened in your exit scenario?

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

Not since... I'm not sure the regulatory change, but if employees are able to sell back to the company or to private investors, resulting in cold hard cash in employee bank accounts, without the company going public, I'd say they are worth something. We can argue about how, without an IPO, the price isn't fairly decided upon, but having cold hard cash in the bank is nonetheless real.

I've never heard of being able to sell back stock options. You don't own anything with an option. You just have the right to buy at a price in the future.

I didn't say stock options. There is a mechanism through which SpaceX employees have been able to cash out some sort of financial object that they received, despite the company not being public.

The comment you were replying to ended with this:

> Stock options are only really, truly worth anything if they IPO.

fair. the important thing here is that IPO is not the only way to liquidity for early employees

Well, I'm not sure it is. People are pretty aware of salaries already for example. This was about stock options specifically.

Right so for options, when the employee leaves the company, they can convert them to shares, and then there are ways for them to sell those shares somehow, and it results in cash money somewhere down the road that isn't just the salary.

IPO is not the only way for employees to access liquidity

It sure fucking seems like it is! Have you tried to buy early stock in startups? You have to have 10K minimum in most cases.

I’d have bought huggingface, openAI, anthropic, unsloth, and many others stock right at this moment if I could get in for less than 10K.

Prove me wrong internet. I’m ready to buy in these companies this minute.

I don't usually see minimums below 25K, which is fine and sensible.

You really need some kind of a proxy to aggregate anything less than that in practice - thinks like crowdcube or similar. Can you imagine having to draw up paperwork just to transact $1200 or something? Doesn't make much sense.

Across the universe of accredited investors, I don’t think that a $10K minimum is a significant barrier.

We can argue whether the accredited investor process is good or bad (I think it’s more good than bad), but I don’t blame companies for not wanting a bunch of $872 high roller outsiders on the cap table.

An outside individual purchasing shares is not the same as employees accessing liquidity.

As one example, SpaceX is privately held but routinely does funding rounds with large investors so employees can sell shares and access liquidity[1][2]. A $10,000 minimum purchase amount is trivial for those investors.

[1] https://www.reuters.com/markets/us/elon-musks-spacex-raises-...

[2] https://www.reuters.com/business/aerospace-defense/spacex-fu...

I'm generally pretty against paternalism in markets, but when you get to the more "finance-y" stuff like this the opportunity for large scale fraud is just so prevalent and there are so many people just looking for their next mark.

If $10k or $25k is an amount of money you have to pause to think about at all you have zero business investing in early stage startups. Simply by the way the math works out you are better off buying lottery tickets because at least then you'll get to scratch something off before going bankrupt.

Sorry, but I DO have business investing in early stage startups. I called huggingface being this big back in 2019. And given your first sentence, I'm going to 100% call this out as projection on your part.

Folks who work in AI/ML know how to invest in the space! You're welcome to ignore the fact that Unsloth is objectively going to pop off (likely be acquired by huggingface) and anyone who invests in it will come out ahead.

The Venn diagram of people who are sophisticated enough to make these kinds of investments with better odds than gambling and people for whom $10k is hard to scrape together is indistinguishable from two circles. I'm sure there are some in the intersection but it's such a small piece of the pie we can effectively call it zero.

If you want to gamble that's your right I'm sure there is a roulette table somewhere near you. But the social harm caused by allowing dentists and grandmothers to invest in seed stage startups greatly outweighs any social good caused by letting that near-zero overlap get rich a little easier.

People here get u on their high horse about investment minimums and the like. Sure, they get real excited about some startup and they may turn out to even be right. I also know people who do angel and seed investing who are beating the bushes for capital or are just holding tight. Startup investing isn’t some magic money tree reserved for the well off. Heck, I’m pretty selective about even purchases of even individual public companies.

In 2019 they didn’t need your $10k of funding. If you contacted them within the 6 months they were starting they would have said yes. In 2019 it was more time consuming than it was worth. So they encourage you to go through a pool of investors which you are scoffing at.

In reality, my project needs funding now. If i bootstrap and get customers, I don’t need to worry about your lunch money. I need someone (or customers) who can fund that same amount for a year.

True that stock _options_ are only worth something after an IPO, but vested and exercised stock options that get turned into equity is a different story.

Equity can be worth something via acquisition from private equity doing roll-ups, corporate buyers looking to fill strategic product niches, etc

Also, for the more heavily vc-funded late stage still pre-ipo plays, secondary market, which can be at a discount to the most recent vc round, or in some rare instances in a hot sector, premium.

One other thing - waiting for the IPO might be the worst thing to wait to do. The public markets are much more fickle than private markets. Once a company IPOs, there's usually a trading moratorium on insider shares, usually 180 days, so by then, the equity value may have completely imploded.

My point still stands even if it's equity. PE/corp buyers may not care about buying out the very small minority stock holders, that is the point I 'm making.

Lets say you've got

Founder A 25% - Voting, Founder B 25% - Voting, Investor A 10% - Voting, Investor B 15% - Voting, Investor C 8% - Voting.

Former Employee A 0.5% - Non Voting, Former Employee B 0.4% - Non Voting, Employee C+ 0.2-0.3% each all Non Voting.

If say Big Co want's to buy the company why do they care about buying out former Employee B? If they can pickup the two founders and the three investors, thats enough for complete practical control.

That hasn't been my experience. I've never had the experience of BigCo only acquiring just enough for 50.1% ownership. There's also clauses in the equity plans for participation on change of control (assuming that BigCo taking 50.1% constitutes change of control)

it's a particular issue with PE, who aren't really doing it for strategic reasons, but really are just there to make money.

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

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

That’s correct, I don’t believe anything illegal was done but certain things were done to dilute the employee share class which didn’t dilute founder shares. Just start reading about preferred stocks and you will realize they can basically be blank cheques to have any value and have voting rights to issue as much other common stock as they want.

Additionally there was some liberty on what “sale price” actually was in the contract. This may be common operation, but the sale price according to my contract was much lower than the amount of dollars which was exchanged for the company.

There’s also a lot of plain fraud in private tech companies.

It's technically legal -- the best kind of legal!

No. Fuck that shit. When the spirit of the law and the letter of the law conflict, I want us as humans to be able to step back and say that, hey, it doesn't make sense when you put it that way, and ignore the rules and do what's actually right.

As someone living in a country with common law and having taking business law 101 (so certainly NAL) this sometimes ends up being a bit of a guessing game as to how a judge will interpret jurisprudence.

There's a lot of room for improvement in legal systems and they move extremely slow due to the political nature of things.

totally, which is why we go to a jury of peers for things

wouldn't you rather the 50/50 chance for some _seemingly_ impartial person to intepret a deal, than have to pay a lawyer more than somethings worth to enforce some complex 500 page word salad to keep a business run by a person whose dones this hundreds of times before?

Ah yes the cornerstone of any stable judiciary - "ignore the rules and do [what I want]."

    > implied contractual obligations

What does this phrase mean? There is no way that any sound contract law will grant any weight to the term "implied". Either it is written (and agreed) or not. So, I would say anything that is not explicit is meaningless in term of contract law. (Again: I am only talking about jurisdictions with serious, mature contract law, not some banana republic.)

Sometimes what the contract says and what the contract _looks_ like it says to a layman can read very different.

- Granted $500k of stock on start, and then have it diluted as stock is added for new investors

- Hollywood accounting - net vs gross

There's lot of places where a contract can be represented as one thing, only to have it be far less than that.

Then it is a poorly written contract, and the party that agreed to it was tricked or poorly advised. Plain and simple. We see this often with "fast and loose" term sheets for some corporate and sovereign bonds on less reliable names. There is a whole podcast (I forget the name at this very moment) that does nothing but discuss dubious bond contracts. Frequently, the co-hosts will ask: "Who in their right mind would agree to such a contract? This clause is totally unenforceable / provides no protection against event X/Y/Z." And, yet, these contracts still exist in the wild.

Dumb question: Do you think the average dev in Silicon Valley pays a third-party employment contract lawyer to review the terms and conditions before agreeing? Sadly, I feel the answer is "no". Speaking personally, I would never agree to such complex employment compensation terms without third-party advice. Yes, I know it is not cheap (maybe 500 USD per hour), but the alternative looks much worse, and most people here facing these contracts can afford it.

> Then it is a poorly written contract, and the party that agreed to it was tricked or poorly advised.

Well, yes? I mean, we're talking about a situation where one of the parties involved in the contract isn't acting in good faith. And people frequently can't understand contracts. Is there anything surprising about the fact that someone was misled or "tricked" in such a situation?

If I say I'll give you 50% of the revenue we generate, and then the details of the contract allow me to bring on other people with the same deal of 50% of the revenue, and then you all share 50% it would likely feel unfair.

> There is no way that any sound contract law will grant any weight to the term "implied".

Nobody is suggesting that any law would.

> Either it is written (and agreed) or not.

Yet you managed to infer things that weren't in the post.

> So, I would say anything that is not explicit is meaningless in term of contract law.

Again, where is anybody saying anything to the contrary?

I'd say that phrase means 'consideration' in some cases, and in any case something like 'reasonable expectation', which would enter into the 'meeting of minds' prerequisite of contract law.

Banana republics like almost all countries with Civil Law rather than Common Law? And also, you know, some US states and the UCC?

The doctrine that anything not explicit is meaningless in contract law is also referred to as 'the four corners' referring to where you look to interpret the contract; this is considerably relaxed in many jurisdictions (and some situations in the US) where there is considerable information asymmetry and/or power imbalance between parties. With employment contracts in particular; to be a good coder for instance, why would you need to know how dilution of options works? Only to avoid being mislead by your prospective employer?

Conversely, in Civil Law jurisdictions, you see that corporations (rather than employees/consumers and sometimes small businesses) are mostly held to the four corners of the contract as they are professional parties that have legal departments and should be presumed to do their due diligence.

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

Can you explain? In most cases, preferences won’t come into play, assuming you raise at a standard 1x preference and sell for more than you have raised. In that case, owning 0.5% should roughly translate into $5M (modulo dilution).

Even with 1x preferences, the company might have raised $2 billion but sells for $1 billion because the investors don't want to get any further losses.

The general rule of thumb is that acquisitions are bad for employees, and IPOs are good, especially if the share price is stable for 6 months.

Also for acquisitions, often you'll have to work at the acquiring company for some time to get money from your options. Or might get options in the acquiring company instead (which again are worth nothing until some future possible equity event which hopefully translates into cash).

There are plenty of valid scenarios where the company sells for a lot, but less than it raised. And 1x preferences are no longer standard post-ZIRP, afaik.

People are often not aware that the value of common is nonlinear, so the value of 0.5% in this case is zero. (For the ML fans out there, the common price per share has one or more ReLU activation layers. :) )

That would be the naive mathematical interpretation and how the system would work if engineers designed it. Lawyers designed it, though, and they probably know some tricks to make that not happen.

Like what? All the examples people have said are where either

1) the company has Nx preferences, for N >1, in which case the company has essentially failed to fundraise or

2) the company sells for less than they raised, which again, is a polite form of failure.

lets no degrade lawyers more than necessary.

Business people hired lawyers to design means and methods to commit _implicit_ fraud and deceptive practices to improve the value of their capital assets.

Those lawyers then go on to sell this product to others.

I'm sure there's some lawyers out there that are going out there shopping this stuff around, but it's Capitalism and Business thats the active agent, not Lawyers.

You think engineers never scam?

Not like lawyers, dentists, car salesmen, etc do!

Have 1x preferences become standard? When I worked in startups early investors often has 2x or 3x liquidation preferences, especially at seed.

I am under the impression that an oversized cap table is pretty much standard. Am I wrong?

Playing both sides with this comment

I don't intend to be on the founders' side at all, I'm just not quite sure I'd throw them in jail over it. I'd definitely call it "cooking the books" comfortably.

Intentional misrepresentation is fraud, but I understand pragmatically how the line could become blurred. What I object to is the idea that blurring that line is intentional, even if that is not acknowledged.

Founders will almost always have common stock too, so they're in the same boat - it's only investors who will have preferred stock. If you don't spend 10 minutes to understand liquidation preferences before accepting a startup offer, that's kind of your problem.

1. If the company is bootstrapped the founders can have preferred stocks with whatever clauses they want on it

2. Most (all?) companies will not show you their cap tables so it basically boils down to “trust me bro”

The logical conclusion to #2 is valuing the equity compensation at zero, and foregoing it and asking for extra cash.

Kinda? The underlying issue is someone you think you can trust not telling you the full details so they can fuck you later.

The underlying issue is trusting someone you should not trust, someone on the other side of the negotiating table who has interests opposite to yours.

Yeah but I'm a programmer and don't innately understand that social power dynamics stuff. They're friendly and nice people and offer me drinks and snacks when I meet up with them. What do you mean they don't have my best interests at heart?

I’ve yet to work at a startup where liquidation preferences and investor participation is freely given or ever even mentioned. I only know about because I participated in TechStars. So, I guess we can blame employees for not hiring a lawyer to review their sign-on agreement (which, again, doesn’t have that info) or we can hold founders accountable for not sharing all relevant data needed to evaluate an offer. As a prospective candidate It’s one of those things you need to know about to even know to ask about.

I think founders are doing themselves a serious disservice. I loved working at startups but it’s just not worth it in most cases. The trade-off was always take lower salary for a chance at making big money and repeatedly investors and founders perform a rug pull.

Blaming employees for a change in the gentleman’s agreement is certainly one way to look at it. But, it sure feels exploitive, especially for younger folks that haven’t yet been burned by it. If founders keep doing it… well good luck finding anyone willing to work at their startup.

Seriously - the whole point of giving your early employees equity is so that you can attract talent without blowing your budget.

It seems like most founders love pretending that there are armies of top-tier engineers rushing to work at their startup in exchange for pay that's well below market and stock that still won't be worth very much even if the company has a wildly successful IPO.

I really wonder why this happens - is it just greed from the founders? The VCs? Do early employees value stock like shit regardless of how transparent the company is?

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

morally, yes

legally, no

Different stock classes SHOULD be illegal. I have yet to hear a single good argument for it that isn't obviously self-serving.

And ownership stake in the company should be a simple thing to understand, not some byzantine mess designed to fuck over the engineers.

I don't know where you live but in my country going to some old person and trick them into signing stuff they don't understand is illegal.

Banks aren't even allowed to suggest buying high risk stuff.

> the founders have different stock class than employees

This is super uncommon.

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

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

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

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

> personally seen it happen multiple times from inside, it happens all the time

I’m not saying it doesn’t. Just that founders having a separate class of stock is very, very rare.

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

Supervoting stock is absolutely a thing with companies. We’re not talking about that. We’re talking about start-up founders.

Its very common, so common that they call them "founders shares"

That’s not what that term means

Please enlighten us

Founder stock almost always convert to common not preferred. Carta article about it: https://carta.com/learn/startups/equity-management/founder-s...

I recommend researching a topic at least a little bit before going on and commenting on it

This serves my point not yours, the process is often very misunderstood by those being promised the equity, and it's often "converted" in ways that dilutes or outright takes away most of the value by the time the employees ever see financial gains from the equity.

That’s not what happens. Literally TFA covers the term “founders stock”. It really is a meaningless term to refer to common stock held by a founder.

Not a separate class of shares. Almost always, founder shares refer to the magnitude of the grant and the voting-rights agreement attached to it. ("Stock class" is a very specific term.)

Where can I read more about this?

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

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

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

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

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

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

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

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

That's what I started as well with this employer. I never wanted to get involved with their other project but they forced me on it. I was trying to find another employer the entire time but it was just around the time Trump got elected the first time and nobody seemingly wanted to hire

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

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

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

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

dilution

Dilution and liquidation preference.

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

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

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

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

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

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

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

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

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

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

At least in public companies there are enough safeguards where I think a reasonable person could be fine with it.

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

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

I'm super curious - what are the six classes and what's the reasoning behind them?

A common structure would be something like:

* Class A - voting shares, founders / controlling parties, etc. Typically small fixed share count (e.g. 100), not issued dividends directly but used to represent percent of controlling interest.

* Class B - non-voting shares, early stage employees, advisors, supporters, etc. Used to issue dividends.

* Class C - Same as class B but reserved for future issuance through more formal programs like ESOP when you're ready for that

Then you might have some preferred shares for investors, say class D and E for two investor groups and then a Class F for convertible debt (even bootstrapped companies can have owner / friends / family / seed / etc money, plus may want to not rule out raising at some point).

This is obviously a lot of classes, but by doing something like this you can separate control from economic upside, create different terms / stock agreements for different classes, keep room for future planning (things like ESOP), facilitate investor needs (they almost always want preferred shares), have more flexibility with fundraising or convertible debt, etc.

I'm not actually trying to argue that exactly six classes are necessary or optimal, but moreso that its common to want not just one single share class. Practically speaking I imagine that firm does six because they're trying to give a template that'll work for many of their companies and reduce the amount of per-customer customization. My company has less although more than one.

Ah, I'm thoroughly familiar with the idea of multiple share classes (although I must commend your excellent explanation and examples here) - I was actually particularly interested what their six choices were to cover the bases as a lowest common denominator etc. No worries at all if you can't say though, I get that.