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Do the math on your stock options

jvns.ca

101–110 of 259 posts

Re: Do the math on your stock options

#101
post #98

> which pays me a SF salary despite me living in Montreal I'm not sure what cost of living in Montreal is, but I'd be surprised that jvns is making less than 100k in SF. If Stripe were smart they'd increase her salary stat. Just based on her excellent blog posts and her insatiable curiosity, this is not an employee you want to lose.

> My after-tax salary is less than $100,000 USD/year

Re: Do the math on your stock options

#102
post #62

Earlier quoted context omitted.

> Never attribute to malice that which is adequately explained by stupidity. So what is the lesson here? I hear this saying over and over, always with the implication of "Give them a pass". Who cares if they are being crooked, or are too dumb to do division. Either way, the employee loses.

There's no lesson. I'm just pointing out that many founders are more focused on tech or product than they are in options and cap tables. And many startups employ staff who are also unfamiliar with such things. Given my experience of advising early stage startup founders on equity investment, dilution, cap tables, etc., I believe that ignorance is at least as likely as malice in situations where they seem unwilling to…

Stupidity is very dangerous in this situation because the CEO may completely believe that he's doing the best for the employees, but then get hoodwinked by institutional investors who will make the deal sweet enough for the CEO so he can be the one to tell you your options are worthless when the liquidation preferences come home to roost.

I would never join a startup where the founder wasn't razor sharp and forthcoming on all these details.

Re: Do the math on your stock options

#103

Earlier quoted context omitted.

You're basing this on what? Not saying your wrong but what is the basis of this opinion ? Employees usually get restricted stock until there is a liquidity event.

"Restricted stock" means the securities are un-registered [1]. The minimum holding time is 6 months. All stock issued by a privately-held company is "restricted stock". Practically all other transfer restrictions are at the company's discretion. ROFRs are the only restriction I've seen widely enough to merit calling "standard". Everything else exists in different forms in different companies, all the way up to being…

What I meant by "restricted" is that it's a restricted class of common stock. i.e. you don't have the same voting rights as the owner or investors in the company.

Your experience is working with investors. Your advice makes more sense from that point of view. Employees are rarely (read Never) afforded the same privileges as the investors.

Re: Do the math on your stock options

#104

As a founder who's been through a liquidation event, I have to say that stock options are a terrible way to reward employees. The tax issues alone (not to mention all the other stuff mentioned in this thread) are a huge pain for most ordinary people. The only reason companies use this is that there's no better alternative... Anyone ever encounter some other financial instrument that's possible to use in this situatio…

Bonuses based on how well the company does.

I.e. $1,500 bonus per $MM in revenue, each year

Re: Do the math on your stock options

#105
post #2

I'm really interested in other people's experiences with understanding how their stock options work. It seems really easy to misunderstand something serious, even if you know quite a lot about equity.

I got an offer from a late-stage (not sure if that's the right term, but they had a shipping product) non-public startup that included 10,000 stock options. That sounded like a lot, but I had problems evaluating that number without knowing the shares outstanding. I asked for that figure, and was told it was privileged and confidential. I decided to value the options at $0, and instead think of them like a non-monetar…

Issuing 10,000 options and not telling you how many options are outstanding is very very common for startups, unfortunately. I don't know how many times I've joined companies that listed 10,000 options and I was too dumb to question it.

In many cases, it's because they don't want non-executive employees to be able to know certain financial details, including the valuation of the company. I wish this wasn't the case, but the reasons for it seem logical and in fact fair - it's just that many people assume this is a lot when it probably isn't.

The downside is many people are apt to accept, thinking 10,000 in options is a "lot", and I've made that mistake in the past. In an A round startup, this number could easily be in the several millions of shares outstanding, and likely is. If it's gone through several funding rounds, it's likely even less. 10,000 in a C round is significantly less if they have divided the stock by 10x or more in the previous rounds.

Executives could be pulling in whole percentages of the company, or multiples thereof, and one of the first few members of technical staff could basically be looking at a year's salary or less in payout if the company would sell in 5-8 years.

The percentage of the companys that make it is also a factor. While the article focused on needing to stay at a company, it's fair to consider that the great majority of startups are going to fail or be very small acquisitions (asset deals, acqui-hiring, etc). In these positions, the VCs will get paid first, and there may not be much if anything left.

Another possibility is the company is sold for small prices but the CEO could secure a very very nice deal to join the new company (plus bonuses), which has happened on more than one occasion.

A VC only needs a small fraction of his portfolio to do big exits, so they make lots of bets.

Stock is a huge gamble. I don't recommend "no stock, just cash", but don't ever let someone underpay you on hopes the stock event will happen.

Stock is being used as a retention tool, and that's the design of it, unfortunately.

I'd be much more in favor of equitable profit sharing as a retention tool - suppose a company decides to give away X% of it's profits back to employees forever, and this is done in a way where it isn't the CEO/leaders making all the money. Instead say in a 50 person company, 10% of the profits always go back to the people, and each person gets 1/50th.

This also eliminates sales commission on large deals and makes everyone part of the deal (the whole company) profits - also no quarterly targets, personal bonus tiers, executive bonuses, or anything like that. As the company becomes more efficient, those numbers go up, and it keeps things simple.

Re: Do the math on your stock options

#106
post #41

It would be so much easier for everyone, if companies would IPO earlier. Evaluation of your option value would be straightforward, there is liquid market, no need to worry about investors preferences, ratchets, etc. Also the whole market gains a lot of efficiency if basic financials are public. Not so long ago, companies used to IPO way earlier... Microsoft, Apple, Amazon...

Unfortunately, it appears that many startups have gotten their valuation ahead of their economics, so IPOing isn't an easy option for them because it would be a large down round. IIRC, most of the large tech ipos in the last year went public below their final private valuations. Though to be fair, the last investors often got ratchets. This is a good read too http://thomasgr.tumblr.com/post/135710601255/the-pre-ipo-d…

Yea not to mention the sarbanes oxley act, post-enron, that makes public company regulations obscenely difficult.

Re: Do the math on your stock options

#107
post #54

Earlier quoted context omitted.

Obligated by law: deliberately acting against (some) shareholders interest is a criminal offense.

people holding options are not shareholders until they exercise those options.

Excellent point, but equally important is the fact that even if you purchase your This is where the GGGP (davidwihl) is both right and wrong—knowledge of the cap table at signing won't guarantee anything, but that combined with a good judgement of character is the best you can do. In the end you can get screwed either way, but if there is any caginess up front then run don't walk away.

Re: Do the math on your stock options

#108
post #76

There actually IS a way to exercise after you leave without laying out cash + tax dollars today. Consider esofund.com, its a fund that will pay your exercise price and tax liability for a proportion of your upside in a good financial outcome. If it doesn't work out, well at least you didn't throw away your own cash. They're basically a vc that takes common stock in companies by getting rights to employee shares.

Only possible if you are able to sell your private shares without a liquidation event (IPO, acquisition) which is often not the case.

This doesn't seem to be a requirement with esofund

Re: Do the math on your stock options

#109

Always ask for: 1. TRANSFERABILITY. If you are given options to buy privately-held common stock in lieu of compensation, you must demand transferability. Rights of first refusal (ROFRs) are fine. "Board approval" is not. "Board approval" means "you may not sell your shares until we go public, except to us, if and when we feel like it, and at a price we get to unilaterally decide". 2. CASHLESS EXERCISABILITY. Always a…

I've never seen the ability to customize these kind of things because they generally are, in my experience, part of the core options agreement for the entire company and would require BoD approval. Thus, you're asking a lot - works if your a key employee but probably not for the average employee. Would love to hear if people have been able to get these terms.

Righto, and asking a lot of demands/questions means the company is not going to like you as much and will influence your relationship after the offer is accepted. The info you get will be standard and there is certain info they are not going to want to share.

Basically a casual ask for "can you share how many options are outstanding?" is about as good as you are going to get. Totally good. Non-stand demands? Not so good.

If the VC has preferential shares (they do) just realize that's ok - and probably fair. Don't join the company if you don't think it can exit above it's funding amounts if you are in for the stock - but hopefully you're in it because you really will love the position and the stock is just a bonus if it makes it.

That's the most important thing :) You don't want to be in a job you don't like just because it's profitable IMHO.

Re: Do the math on your stock options

#110
post #2

I'm really interested in other people's experiences with understanding how their stock options work. It seems really easy to misunderstand something serious, even if you know quite a lot about equity.

I got offered a job 4 years ago at a very early stage company with really generous stock options. I didn't know what options meant, I didn't know that I had to exercise. That was pretty silly on my part but in my defense I was getting my visa, moving across the world, and working as the first employee trying to keep up with insane growth.

When the time came to raise our second round, I got intrested in how it would affect my shares and sat down to understand this whole shares thing. And to my dismay it turns out I have to pay for my compensation! I was pretty disappointed, even felt a little bit of resentment that no one took the time to explain things to me. But the reality is that your employer is not obliged to explain how your compensation works -- after all it's all in the contract (except it's written in awful legalese).

2 years later when I quit my job I was broke and barely had enough money to get by until my next paying job. Anyways I hustled to borrow money and exercise my options, all the while I still haven't understood the tax implications (I still don't!). My CPA told me that I can delay paying taxes on this until a liquidation event, and my coworkers who quit at the same time got similar advice. Now and after talking to others who exercised their options, that advice seems out of place and flat out wrong. I'm now trying to figure out what to do next, most likely getting a new CPA or a tax attorney. The whole thing is really stressful and I feel like startups can do better by their employees. At the very least substantially extending the exercise time and making it a standard in SV.

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