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TLDR Stock Options (tldroptions.io)
819 points by ingve on June 1, 2017 | hide | past | favorite | 205 comments

Our goal with building this was not to be comprehensive, but to give founders and employees a way to have a more productive conversation about options and what they are worth. Too many startup employees I meet don't properly value the options they have, and too many potential hires don't negotiate for the right things, and wind up disappointed.

We hope this will take a small step towards correcting this problem.

For many years, startups have exploited the opacity of potential outcomes to trick employees into thinking that their equity is worth more than it likely is.

A couple of years ago, I asked AngelList's CTO if I could utilize their data to build something like this; he never got back to me, so I moved on. Really glad to see this project live!

EDIT: Just realized this came from the fine folks at LTSE. Awesome stuff, Tiho!

Tools like this are really helpful for startup employees. Thanks for sharing!

Looks like there are some hidden assumptions about liquidation presence etc. Might be good to add a slider for that. (My employees would do pretty well at a $25M exit!)

Hah. This is a good point. I was going to call you out for having barely any employees and so of course they'd do well. But, for anyone who hasn't tried this, if you give the hypothetical employee 10% of the company, they come out with $0 in all scenarios at a $25M exit on this tool.

And it looks like this is the slider you were asking about. ;) https://captable.io/

Really? And you sure, once money is on the table, magically the priorities onto who is getting the money wouldn't change?

It didn't during our last exit.

Neat tool, I was able to put more than 100% ownership into a Company though and I don't think that should be possible.

If you press "9" enough times: http://imgur.com/a/wUvOy

We found the QA engineer.

Yah but is the math wrong?

Do you want $NaN after all your hard work?

Well, it would be satisfying to see its effect on the IRS's computers :)

If you keep adding 9's you get back to 0.

Nice - it supports The Producers accounting.

It's also possible to put in negative numbers :D

From a purely monetary and risk-based viewpoint, whether to join a start-up depends on how much money you already have.

Suppose you regard tldroptions.io's probability distributions and outcomes as correct, and the only thing you care about is maximizing the long-term rate of goal of your capital. Then the Kelly Criterion (https://en.wikipedia.org/wiki/Kelly_criterion , a.k.a. Fortune's Formula) says that you should try to maximize the geometric mean of your capital, which amounts to maximizing the expected logarithm of your capital.

To make this concrete, suppose you are choosing between two options:

- (Startup): Working at series C+ start-up for three years, where you receive 1% equity and $100k/yr salary, and have a 20% chance of getting ~$60 million in 3 years (according to tldroptions.io)

- (AmaGooFaceSoft): Working at AmaGooFaceSoft for three years, where you receive $300k/yr total comp (according to patio11)

For simplicity, I will ignore taxes and the time value of money. All monetary amounts below are in millions of dollars. If you have no money in the bank to start with, the geometric means of your alternatives after 3 years are:

- (Startup): exp(.2 log[60+0.3 ] + .8 log[0.3]) = $0.86 million

- (AmaGooFaceSoft) = $0.9 million

In this case, AmaGooFaceSoft is slightly better.

On the other hand, suppose you already have $1 million. After 3 years you will still have the $1 million, plus your salary and whatever money you get from your equity. Here the geometric means are:

- (Startup) exp(0.2 log[6+1+0.3] + .8 log[1 + 0.3]) = $2.8 million

- (AmaGooFaceSoft): 1+0.9 = $1.9 million

In this case, it's better to join the start-up.

The base salary matters a lot. If you have no money in the bank, but you get $150k year at the startup instead of $100k, then the geometric mean of the Startup option after 3 years is better than that of AmaGooFaceSoft:

- (Startup): exp(.2 log[60+0.45 ] + .8 log[0.45]) = $1.2 million

1% equity in a series C startup sounds wildly optimistic. You would most likely not get that much equity as a senior software engineer. It's interesting that your first calculation still favours the other choice.

Yeah, I agree. There's no way that an engineer is getting integer percentages of equity after seed round. Maybe if they're highly recruited, in which case Google et al. would pay more.

You can get integer percentages right after a seed. (No way at Series C though.)

Who would get integer percentages after seed round?

C-suite hires that have other choices and capital investors.

Yeah, I agree. No way someone in C round will get 1%.

A C-suite would I think, not an engineer.

a c-suite would get more than that, probably closer to 3 or 5%, and also a signing bonus, as well as performance bonuses, a huge options package, and a termination clause / parachute clause. hell, throw in a relocation package and a credit card for entertaining customers and partners also.

On the other side though, $100k salary is widely pessimistic for a Series C employee who could command $300k total compensation at a FANG-type company. Realistically, their base salary would be closer to $150k - $180k.

Shit could always hit the fan though.

I joined Zenefits when everyone had dollar signs in their eyes. It felt like the roaring 20s (or at least the accounts I've heard of them).

How are they doing nowadays?

I always say don't compromise on salary for equity. Compromise for the experience, for an entrance into the field, because the chick at the counter was digging you, but not because of some payout you think you'll get in the future.

They're still a unicorn aren't they?

This is fantastically useful both as a side-of-the-barn estimator, and a teaching tool. Thanks!

Two things a lot of startup employees are unaware of that are worth highlighting: they actually have to buy their options, which eats into returns, and that if they leave the company they have a limited window (30 days, typically) in which to do so. In would behoove them to save/plan for this fact.

This is especially true in this time where even successful companies drag their feet when it comes to IPO. If you don't think you can't afford to buy the options and pay the taxes (yes, there's taxes when exercising illiquid options), then you have to discount the chances of still being with the company at the time of a liquidity event.

This means you can find yourself valuing stock options very little, even in cases where you have full faith in the company making it and being very profitable. A growing company is very different year to year. What are the chances that you'll love the same company in 6 years?

My personal calculation is that I have a 50% chance of leaving a job every year, so if I am guessing that it'll take 6 years to IPO, and I don't think I can just keep large amounts of money frozen in options, I have to discount the value of said options over 95% on top of the traditional calculations. RSUs from he big four don't have that problem.

> This is especially true in this time where even successful companies drag their feet when it comes to IPO.

That's a very weird statement. Companies are under no obligation at all to ever offer stock to the public.

An IPO comes with all kinds of downsides and many companies simply do not feel the benefits weigh heavier than the downsides. Such as: transparency, SOX, all kinds of restrictions and demands regarding communications, dealing with the SEC (or the local equivalent) and so on.

Though if they're hiring people with the enticement of stock, they're arguably under some obligation to somehow allow some liquidity ever.

They are only breaking the spirit of agreement, not the agreement itself :)

I don't claim that there's legal obligation. I don't claim that there isn't, but I'm not sure where it'd arise from.

It was a joke, modified from the recent NSA joke that "NSA only breaks the spirit of the law" :)

I certainly didn't intent any offense.

> I certainly didn't intent any offense.

None was taken :)

If they've taken VC funding, they most likely are.

The percentage of companies that have taken VC funding and that eventually IPO is far smaller than the percentage that either become a going concern or that end up being acquired by another company or by a private equity party.

Do you mean "cease to be a going concern"?


Ok, I thought you meant "becoming a going concern" as an alternative to an IPO (an IPO will also result on becoming a going concern, if it was not one already).

Ah right, I see what you mean now. Yes, I could have worded that clearer. It should have been 'simply to continue to be a going concern', not as if companies that have IPO'd are no longer a going concern.


Thanks! I really appreciate the feedback.

The price of the options eating into returns is reflected in the number we present (we assume a consistent valuation growth by stage and at exit), but taxes aren't and those can 40%+ in the US, which people don't necessarily expect. Limited exercise windows are one of the things we have in the list of ways this can go horribly wrong, but you are right that it is something that you can plan for if you know it's coming.

Thinking about it, that and early exercise might both be candidates for some sort of "list of questions to ask" tool...

Early exercise / 83(b) has another benefit that most people aren't aware of -- if the exit is at least 5 years out, you can exclude 100% of your gain from federal cap gains tax under IRS Section 1202.

See here for more: https://blog.wealthfront.com/qualified-small-business-stock-...

Aren't 83(b) elections only really available to founders, though?

No, it's at the discretion of the company. I asked for an 83(b) option at a 10 person startup I worked at and the CEO made it happen. The startup still went under so it didn't matter in the end, but management definitely did what they could for the employees.

Early employees (<25) can often negotiate them as well. I've done 83(b) at every startup I joined.

> they actually have to buy their options

Yup. It honestly astounds me how many people don't factor this into their decision-making. Your only equity compensation on joining is the delta between your strike price and the current market value of your stock. This is often very little, far less than you give up in salary at many companies.

Yep. This is a very important point. If you are experienced and planning on joining a startup try to negotiate for early exercise or a very long exercise window for your options. Either that or be prepared for a nasty bill if you ever decide to leave and the start up is doing well.

How does this tool help you work that out though.

This tool reflects that profit by assuming a current strike price based on average valuation changes between rounds. Instead of saying that you get the full value of the stock you buy, the calculation takes into account that you also have to purchase the stock.

This tool doesn't explain the dynamics going into the estimated profits (though it links to things that do), but it helps people avoid over-estimating the value by missing dynamics like strike price.

I never said anything about this tool. Do that calculation yourself, if you're looking at thousands of dollars in compensation it makes sense to do the research and unerstand things fully.

And though few think of buying options as a taxable event, the bizarro world of AMT treats it that way.

What's the reason for these companies offering stock options rather than just stock?

It's easy to point all the details that matter in valuing your stock options -- liquidity preferences, strike price, options vs RSUs. The genius stroke here is to focus on the two big details that matter (% ownership and exit value) and focused on that.

Caveat: this doesn't work in a "down exit" less than the previous round's value.

As @bethcodes says, this is not a calculator, because while these two numbers will get you within a factor of 2, knowing the details will help you get even closer.

(Disclosure: I built a calculator to help you do that: http://www.optionvalue.io/calculator/)

Totally agree. We hope this will be an on-ramp to more sophisticated tools and analysis for beginners.

I have a bunch of options in my company, but I don't know what the total number outstanding are, so I have no idea what percentage of the company I own. 1) Is this a common scenario? 2) Is there a way I can find out what the total number outstanding are?

This type of smoke and mirrors bs is common in tech startups in my experience. The good news is even if the company is unwilling to disclose, Delaware law requires companies incorporated there (most tech startups, even in the Valley) to disclose key cap table numbers to share holders. You can exercise even 1 option to own a share and send the company a letter asking/demanding the info you seek.


"As a Delaware corporation, all of the company’s stockholders (including minority stockholders) have the right to inspect and make copies of the company’s stock ledger and its books and records upon a written demand to the company. The stockholder’s inspection rights also apply to the company’s subsidiaries. Although Delaware corporate law does not specify the types of books and records that the stockholders may inspect, these rights extend, at a minimum, to the company’s financial records and corporate minute book."

Not telling you the total number of shares is a little bit like saying I'm going to pay you 1000, but not telling you which currency it is in.

If you ask the company should tell you what the "the total shares outstanding on a fully-diluted basis" is. If they don't tell you when you ask it's cause for concern; otherwise there isn't a way to tell what your compensation might be worth.

Send an email to the people who manage the options. Say that you are trying to figure out your finances, and would like to know how many options are outstanding.

Note that there are complicated ways that that more options might appear, depending on the company (e.g. sometimes debt can convert to equity) that they might be a bit more hesitant to talk about, but they should be pretty open about the total number of shares currently outstanding.

This. If you have a CFO, contact that person. If not, then anyone in finance, or a partner. Everyone is there for pay. This is a reasonable request.

Buy one share, ask to see the books.

Would knowing the fair market price be a proxy for percent ownership (assuming you know the current valuation of the company)?

+ Most new sparkly eyed employees who sacrificed cash pay for options are blissfully unaware of preferred shared.

This could keep slider at $0.00 for a longer (further on the right side).

Thanks for the feedback!

Preferred shares are reflected in the current payoffs; that's what's responsible for the "low exit" portion of the slider not paying off at all. Are you talking about participation preferences that let VCs double-dip? Those are a whole different kettle of fish, but also not as standard as preferred shares.

This is an area that YC has the oppotunity to step up and lead founders to be transparent but chooses not to. I wish i understood why.

information asymmetry is part of the secret to business success

I assume you are not being sarcastic. It is true, but in this case its a limiting to early stage companies. I know, I personally will not join one that doesn't disclose liquidation preference, type of shares I had etc. unless they were offering more base comp than big corp to offset my risk of joining a company with a 65%+ chance of failure.

By disclosing terms of the shares, great companies could attract better people. You are not going to trick good people with shares, only fools.

It might be part of the reason why you tend to see older people in bigco and younger people in startup co.

Or, it could just be that BigCo is... bigger? :)

I actually think the biggest reason is that start ups need an army of really good individual contributors. They dont need managers or leaders until they scale. At that point, the speed is too fast for experienced people to just enter so young people become managers. And young people dont want to manage people older than them. Bias continues.

Just curious why the downvotes?

You offer no particular evidence for your claims, they are unpersuasive and you manage to insult both older and younger employees in the space of three sentences.

A. You assume young people are "really good individual contributors" and older people aren't, which is very often exactly backwards.

B. It has been my experience that startups often hire people with management experience as they scale.

C. Your assertion that young people don't want to manage old people is unsupported and pretty much just sounds bitter.

The original hypothesis that younger developers are more likely to be overconfident about their chances of success and so are willing to accept lower effective pay makes way more sense than that older developers are less good at being individual contributors.

Thanks for summarizing. I completely see your point, but I want to explain in a little more detail. Wasn't trying to insult anyone!

> A. You assume young people are "really good individual contributors" and older people aren't, which is very often exactly backwards.

Not my assumption. But, as someone ages, if they are an excellent individual contributor, they often find themselves in management roles. There are exceptions, but the real problem is that as people age, they want to be called "people managers". And, startups don't need people managers, they need contributors so there is a mismatch.

If an older person only wants to be an individual contributor, there are of course places for them, but my contention is that the cross section is extremely small. I can see why it seemed insulting, that isn't want I meant.

> B. It has been my experience that startups often hire people with management experience as they scale.

Sure, they do, but more often than not, they are hiring their strongest individual contributors from within. Only a small percentage of people hired are hired from very senior roles.

> C. Your assertion that young people don't want to manage old people is unsupported and pretty much just sounds bitter.

I have worked in 3 large organizations and 2 small organizations, it is extremely rare for a younger person to hire someone older than them. I cannot imagine that there is evidence counter to this claim. I have seen it repeatedly.

Yeah, but does that really matter if, after you've joined, they start raising money and clam up about the terms?

No reason yc shouldnt be encouraging founders to share terms.

Nice app! I have to admit this made me chuckle:

> Instead of trying to get the right answer, we set out to build a tool that could get an answer.

I'm curious though, from where did you get the numbers about the likelihood of an exit? I thought it was pretty interesting that a Series C is statistically less likely to make you money than a Series A, according to this.

Hi! I'm the engineer :) I used two sources of data: https://www.cbinsights.com/blog/venture-capital-funnel-2/ which was specific to tech companies and http://files.pitchbook.com/pdf/PitchBook_1H_2016_VC_Valuatio... which covered more than just tech companies. Both only consider companies backed by American VCs.

Interestingly, data I found from 2010 was very different. It seems like more recently the popularity of early acquisitions (especially in biotech) and more robust seed funding have shifted the distribution of outcomes. It could definitely change again: success rates are by no means consistent.

Serious question: Would you have enough data at this point to tell me how many lottery tickets I could buy to replace the odds of winning on startup options based on option metadata (startup round, options granted, etc)?

Think of it as investment diversification.

One way to look at this is with the Kelly Criterion (https://en.wikipedia.org/wiki/Kelly_criterion), which says that in order to maximize the long-term growth rate of your capital, you must maximize the geometric mean of your capital at the end of each decision point. To make this concrete, I'll take CA Powerball as an example. According to http://www.calottery.com/play/draw-games/powerball/faqs , the jackpot starts at $40 milllion, and your odds of winning are 1 in 293 million. For simplicity I will neglect the other (smaller) prizes, and the chance of splitting the jackpot with someone else, taxes, time value of money, etc.

Suppose you have $100k in the bank, and tldroptions.io says you have a 20% chance of receiving a $60 million payout. The geometric mean of your capital is then $360k: https://www.wolframalpha.com/input/?i=exp%28.2+log%5B60%2B.1...

It would take 62 million CA powerball tickets (each with different numbers, in the same drawing) to give the same result: https://www.wolframalpha.com/input/?i=exp((x%2F293000000)*+l...

In the worst case, an option is going to be worth 0 and in the best case it's going to be worth > 0, so the value of an option is always positive until the company actually dies.

Lottery tickets, unlike options, cost money up front. You still can't lose more than you pay, so the payoff curve is similarly non-linear, but unless you can trade options for cash options will always beat lottery tickets.

Lottery tickets are easy to diversify in that you can buy a variety of numbers. (The times when lotteries have become a net-positive buy the buyers takes advantage of this fact.) Employee startup options are more like buying one set of numbers over and over again. On the other hand, the odds of getting any payoff from options are somewhere around 15-30%, whereas the odds of getting any payoff from a California SuperLotto Plus ticket are ~4.3%. Because you can diversify ticket numbers, you could get the same odds of getting any payoff by buying 14 tickets with different Mega numbers, which would earn you $1 to the $14 you spent. If you could buy stock in many different startups, you would be called a "venture capitalist" and those folks on average do much better than people who play the lottery.

Finally, the maximum payout of a lottery ticket is capped and known ahead of time. The largest lottery win in the US was $656 million. On the other hand you don't know going into a startup what the payoff for that particular startup is going to be, and the largest exit of all time was Facebook at $104 billion. Just like with the lottery you don't know how many ways you are splitting the payoff, but unlike the lottery it's going to be based on the decisions of the board/founders, rather than random.

Basically, the lottery is a lot simpler than a startup, with few sources of actual uncertainty, and so there's no real risk involved. It is just gambling: you can do the math to figure out what edge the house has and figure out for sure that you shouldn't do it. Startup options, on the other hand, reflect actually-unknown unknowns, and so are more valuable to those who hold more-optimist-than-average beliefs about the probability of that particular startup succeeding.

> In the worst case, an option is going to be worth 0 and in the best case it's going to be worth > 0, so the value of an option is always positive until the company actually dies.

That's only true as long as you're still working at the company. If you leave, you have to exercise, and then the worst case becomes negative.

You can also choose not to exercise and just walk away, in which case the value is still 0. Though I imagine a lot of people would have trouble doing that even if they didn't think the company was doing great.

This was linked on HN previously - "What I Wish I'd Known About Equity Before Joining A Unicorn"

tl;dr in one word: "Beware"


A QA engineer loads up a webpage and orders 0.1 percent of a company. Then 1%. Then back to 0.1%. Then clicks the down arrow -- ah, zero percent.

Then clicks the down arrow again. Negative numbers ensue.

True story, except I'm not usually a QA engineer.

I bet you it's still 100% coverage tested...

Ah, the glories of default html input behavior!

I find a more important question is "What percent should I ask for?"

The company I work for is about to get major investment and they are transitioning from an LLC. Only the 3 founders have equity currently. As engineers we have no idea how much to ask for. Because we have already been working without equity. How do we account for the years we've worked? Or that our salaries aren't that great right now.

Wealthfront used to have a great compensation estimation tool: https://blog.wealthfront.com/startup-employee-equity-compens...

But it was mysteriously deleted without reason.

Thanks, that at least gives some area for me to guess within. Noting ".15 – the percent of shares that employees excluding executives typically own"

So I would take it we should ask north of this number. Being that we're small, don't have great salaries, and have been working for the company "because we believe in it" before getting any real promise of compensation.

Lol you need leverage, then ask for something reasonable.

Well what is "reasonable". I think most people don't know what that is.

Your maximum value. This is a function of replacement cost.

"A function" isn't an answer though. Elaborating on weights of said function is. One that would allow the questioner to determine "reasonable". Your answer does not allow for that determination other than by guessing in the dark.

Exactly that's because it's dependent on their situation. How valuable is the business, what specific work they do. , what stage and what growth and are they the people to take it to the next level?

Are these numbers accurate for "% of companies will never exit"?

Seed 74%

Series A 65%

Series B 68%

Series C+ 71%

If so I'm a little surprised that seed and series C+ companies have approximately the same chances never exiting.

Series A and B are easier (cheaper) to acquire.

Correct me if I'm wrong. But from what I tested you get $0 unless the IPO/sell is over $40M. No matter if Seed or Series C or how much of the company you own.

Yes, but the default is set to the employee getting 0.01% of a company that raised series A. That's a very pessimistic percentage. Think of it this way: the startup could hire 100 employees, each at 0.01%, and only give up 1% of its total equity. That's way too low.

Typical grants for post-series A employees (the 10 to 50 first employees) are at least 10X more than that. With that calculator, you get something (~ $20K) for a $40M exit. Not 0. Not amazing either.

That is correct! Rather than try to distinguish the Series A startups that exit during Series A from Series A startups that are going to raise more money before exiting successfully, I just assumed that every company raised the average amount that a successful startup raises. That average isn't stage-specific either.

This was one of the places where the model could be a lot more accurate, but at the cost of much more complicated math.

The "How We Guesstimate" answers this.

  (Exit Price < Money Raised) ? $0
And the site is assuming the company raised $41M in funding.

that's because of liquidation preference. they assume the company has raised $41M

Needs an NPV field and equivalent effective average salary difference per year. :-)

Why probability of exit of series B company lower than series A? That sounds, at least, counterintuitive.

Total guess: maybe there's a greater chance of exit for very early stage (easy acquisition target) or very late stage (IPO). A lot of the failures that make the news are companies that hit the Series B or C phase and realized they had no path to IPO or acquisition.

It could be that post-series-B companies are less attractive acquisition targets. I don't have any data on this.

Quite possible that the really good companies don't need to raise after Series A

Yep, IMO unless you are a founder, if your company isn't one of the top companies of the decade your 4-6 years of pay-cut toil as an early employee will likely just not be worth it, at all.

The expected value of working at an early startup gets overestimated, by a lot. If you're optimizing your career, either make the most you can at an established company, or start a startup.

Or... work at an enlightened startup, that understands the state of affairs, and offers really generous lifestyle advantages - i.e. go work remotely for a couple months if you want, otherwise they are just exploiting misinformed young people and their founders likely have some ego issues.

I completely disagree. It's really not hard to find a company with great product market fit, say series B, get a bunch of equity, a decent salary, and wait a couple years for your equity to be valuable. Assuming the company is successful (of course there's risk there, but by series B a lot has been mitigated), your equity will likely be quite valuable. I actually think, risk adjusted, that's the easiest way to make a bunch of money.

I joined a startup long after product market fit, it was pretty obviously going to be moderately successful, and I was employee ~100. I never worked too terribly hard, and my equity was worth about 50% of my (not too low) salary each year.

If you're not joining at or before series A, a lot of the risk has been mitigated, and there are markets opening up to sell your equity into.

Even post-B, the odds aren't good. They're better than pre-A obviously but it could still be 4-5 years and there are a ton of ways to f* it all up before then.

I just wrote about this last week - https://medium.com/@CaseySoftware/tech-ipos-an-inside-out-vi... - after personally experiencing IPOs of both Twilio (joined post-B) and Okta (joined post-F).

Edit: Replaced the link to my site with the Medium post.

> my [startup] equity was worth about 50% of my salary each year.

The equity of many AmaGooFaceSoft employees is also worth at least 50% of their yearly salary.

Yes but that's if I were to sell it after ~1 year at a company you've likely never heard of. If I wait 3 more and there's a large exit it could easily be worth millions.

Do you have a convenient way to sell your startup equity after ~1 year? (i.e. before there's an exit)

There is a developed secondary market for venture-backed companies' stock. (Source: I do this.)

I thought private stock transactions were subject to board approval, or is that just Canada?

It depends on the company. Some companies are quite liberal with transfers. If you have a bona fide offer, they'll amend the cap table. For others, my having a relationship with the founder or Board is critical. A good starting point for American companies is is their Certificate of Incorporation. If you exercised options, the Restricted Stock Purchase Agreement should also contain terms, e.g. the company's transfer policy or right of first refusal.

I have never heard of a Canadian company looking to raise capital structuring itself under Canadian law. Commonly, you'd have a Canadian law subsidiary wholly owned by a Delaware corporation.

Disclaimer: I am not a lawyer. Hire a lawyer before selling private stock. Do not take investment or legal advice from my Internet comments; they are neither.

There's an EU startup that's trying to create a blockchain based market for shares of pre IPO startups: https://markets.funderbeam.com/market

Depends on the terms. In most startups board can only match the offer.

Lol.. good luck.

Not convenient, but definitely possible. Equidate is a fairly open market for that kind of thing.

That is an exit of sorts.

But there's also a much higher risk that your options will be dilluted to nothing.

> if your company isn't one of the top companies of the decade

GGP covered that option quite nicely. Those are companies that are clearly at the top companies of the decade, maybe even longer.

> Joining a series B startup and waiting a couple years is the easiest, risk adjusted way to make a bunch of money.

Sorry, what?

I'm glad I'm not the only one who did a double-take at that statement. The key qualifier is "risk adjusted", but that's not really meaningful from the employee's standpoint: You can only bet on one company at a time.

Imagine what kind of stock investments you'd make if you were only allowed to invest in one stock at a time.

Let's say 10% of start-ups succeed to the point where employee 100 makes "a bunch of money", which I think is very generous. You would need to join 10 of these start-ups throughout your career (and of course remain at each for the 3-5 years it takes to learn if the lottery ticket pays off) to have an expectation of one case where you end up that bunch of money.

So yea. Risk adjusted. While the EV might look good, the variance makes it a losing game.

I'm not sure what you mean by 'expectation of one case' here, but just to clarify: rolling a ten-sided dice, 10 times, gives a 65% chance of rolling at least one 10. So you still have a 35% chance of zero 'wins'.

I can't comment on the rest of your model, but its worth keeping in mind how the binomials shake out.

Ack, you're absolutely right. Don't know where I was going with the hypothetical example but my math was totally wrong.

Actually, your statement was entirely correct. "Let's say 10% of start-ups succeed ... You would need to join 10 of these start-ups ... to have an expectation of one case [of success]."

It is a true statement that the expected number of successes after 10 tries would be 1. It is also a true statement that your chance of zero successes after 10 tries is 34.8%. (The balance comes from the outcomes that include multiple successes.) It may be that the latter is the more relevant and interesting statement to make, but your math was totally right.


What about staying for 1-2 years per company? Then, you can diversify twice as much as if you stay 3-4 years per.

Where "a bunch" = 2-3m

Yes. However, you are basically making the argument that your options are worth ~50% salary. The problem with that argument (at least in the valley) is that you are making the calculation off the initial starting salary. Salary/RSU growth at companies like Google, FB, etc is surprisingly rapid in the first ~24 months, to the point where I would argue that if you haven't doubled it in that timeframe you need to work on your extrovert/self promotion skills

I only stayed 1 yr

This is just an anecdotal account of your single experience, it isn't making a strong case for your general point.

> but by series B a lot has been mitigated

Or, the fact that a series B is needed is indicative that there was more risk than anticipated. Series B is not always good news (in general it is though, but there is still plenty of risk at that stage). So always verify what the reason for a funding round was and make sure that it was an 'up' round rather than a 'down' round.

> It's really not hard to find a company with great product market fit, say series B, get a bunch of equity, a decent salary, and wait a couple years for your equity to be valuable.

Still so many phony companies out there even at Series B.

> I actually think, risk adjusted, that's the easiest way to make a bunch of money.

It's really not. Risk-adjusted go work at Google for 10 years and you'll probably make more.

If this is easy for you, you should quit engineering and run a growth equity fund.

> If this is easy

If what is easy? Making a few million in a few years is never easy, but I don't know of a better way to do that on a risk-adjusted than joining startups after product/market fit.

And for what it's worth I don't build very much anymore, unfortunately

> and wait a couple years for your equity to be valuable

Product-market fit does not imply appreciation. Growth is priced in. Unless you think you know more than the market (the VCs), you shouldn't expect a return.

Product market fit and further growth are generally pretty correlated, though

Yes, but growth and appreciation are (theoretically) not. Growth is priced in. You're saying product-market fit -> growth -> appreciation. The first part of that is true. The second isn't. Assuming market efficiency, the VCs know just as well as I do that the company is going to grow, so they'll pay a higher rate, which means my options will be priced higher (or I'll get fewer RSUs, accordingly). Growth does not imply appreciation.

Assuming market efficiency at series B is quite a leap, IMO. That said, let's roll with that assumption; you need to find a company that continues to grow, or in some other way derisks itself.

This is like saying "To make money in the stock market, you have to find stocks that will go up." It's tautological.

I'd love to see stats on total comp for engineers at "normal" established companies. Sure, everyone knows that you can make a lot more at Google / Apple / Facebook, but it's also significantly harder to get those jobs and not everyone can.

If you're a SWE at Oracle, are you really going to make much more than you'd make at a 50 person startup? According to Glassdoor, not really.


Just look at the Oracle SWE salaries: https://www.glassdoor.com/Salary/Oracle-Senior-Software-Engi...

Even including total comp, that's barely more than I made the the first <20 person startup I joined.

Is Oracle a good example? I think they are known for abusing H1Bs.

Look at another mid size company as a developer.

"Yep, IMO unless you are a founder, if your company isn't one of the top companies of the decade your 4-6 years of pay-cut toil as an early employee will likely just not be worth it, at all."

Not worth it financially, considering opportunity cost of not working somewhere that pays more.

Just pointing out that there could be other non-financial benefits from working at a startup, that might make it worth it. Everything from you enjoying your time more, to the work helping you gain skills faster and make you able to get a higher salary down the line.

I'm at a startup now. When I was looking for a job last year, I had 3 offers and this startup was the lowest in terms of compensation and while the other two offers were higher they were with large corporations.

While I'm a little disappointed in my pay, I get a ridiculously flexible schedule, work from home whenever I feel like it, I put in some extra work last weekend so my boss just told me to take tomorrow off (which is a common occurrence), the work I'm doing is 5x as interesting and I get to try my hand at a breadth of tasks. I also ended up getting a fantastic title after 6ish months as I was hired in under a pseudo title and they had the mentality of "show us what you can do." There's always new/more difficult tasks I can jump in on when I'm ready.

My other two offers did not have flexible schedules, one had no work from home and the other allowed it sometimes. They were both clearly defined roles, despite my interviewers telling me about all the cool projects I "might" get to do l've learned to never consider any "mights."

I think I'm another year or two my pay will be higher and I will have a more interesting career than if I had chosen one of the ther offers.

I don't expect to get anything from this startup other than experience and a paycheck. And the experience definitely makes up for the lower pay.

One thing to be aware of is that titles given by small and medium-sized companies are viewed differently than titles at large and well-respected, well-known companies.

For example, someone who is a VP at a startup might equate to a typical Manager at a larger company. Someone who is a CTO or Chief Architect at a startup might be a Senior Engineer at a larger company.

Large companies have an approximate scale in mind for their titles, where a Manager, Director, VP, etc. are responsible for (on average) a certain number of people reporting to them, and a certain amount of budget. "Director" level at a large company may entail responsibility for hundreds of employees and significant budget. That director has far more actual responsibility and scope than a startup "VP of Engineering" with a 10-person team.

To put it in different terms:

Anyone can pay $50 to incorporate online and they'll be a CEO. The actual prestige of the person and their CEO title significantly depends on the prestige and scope of the company. From a career perspective, what others will care about and evaluate are a person's actual scope, responsibilities, and accomplishments.

So be careful about viewing a title as a reward; a better reward is an actual increase in scope, responsibilities, and compensation.

Absolutely agree. It's funny, first time my boss brought up upping my title my response was "it really doesn't make a difference, but sure that's fine."

Because of my lackadaisical response it never got changed. Couple months later my boss's boss brought it up because they needed it for some form and she asked if I wanted an even higher title than what I was offered initially. I said "sure."

I don't expect much from it, but every stupid signal helps next time I'm job searching.

That's true, but even with size-adjusted titles you can get faster promotions in a startup. It's pretty common to go from being an individual contributor to running a small team to running a larger team, all within a year or two at a startup. That sort of career growth is unheard of at more established companies.

I've had a similar experience. I've loved the team I work for, the projects I've built, and the opportunity to have impact. I would not be as happy somewhere else.

I would add to that that if your startup pays enough for you to live your lifestyle in the area you choose, then it's okay to leave money on the table so to speak.

You can always go retire at a big company later. The younger you are, the easier it is to take these sorts of risks.

But also think like an investor. Don't put your $x00,000 investment in a startup just because it's cool. Do it because you believe you'll make a positive ROI.

> If you're optimizing your career, either make the most you can at an established company, or start a startup.

I feel I'm optimising my career, working as a sysadmin at a small startup. It's not optimising for money, but I get to touch a lot of tech and design a lot of infrastructure. Make a few mistakes and learn from them. I'm not implementing someone else's design here.

But who are you learning from? Is there a senior sysadmin at the startup? Mentorship matters.

Yes FYI last years basic employee (5 year) scheme at BT returned over $200,000 if you maxed out the contribution, Bear in mind this was avaible any employee even a junior engineer (lineman in US speak).

Oh and you had zero chance of losing any money and you can take share save money tax free

Always good to work for a monopoly..

lol not for a long time has BT had a monopoly unlike the US which left local monopolys intact

really and you don't think the fabulously wealthy tax dodgers who own the DT don't have their own agenda or are making nice with Murdoch in a you scratch my back ill scratch yours :-)

Al those competitors want to do is cherry pick profitable customers and the USO can go hang.

Or just keep hopping until you find something that you like and pays what you're worth

Did you just delete your comment or was it somebody else?

A little monkey patching and you've got some salary info too! https://pastebin.com/3WdXMSdL

Unfortunately doesn't parse the "$1 million" mark. But that's ok, because let's be honest. It's not going to exit that high.

Something feels off with the data here. 65% of Series A companies will never exit, but 71% of Series C+ companies will never exit?

Edit: Thought about this a little deeper and it is possible with a lot of companies exiting prior to the Series C, but suspect the data set of Series C+ companies may just be too small?

The data set is definitely small (CB Insights data only had 61 companies that raised four rounds, for example), but it also surprised me how many Series C companies failed to raise. It might be because earlier acquisitions are an easier exit than trying to become a self-sustaining company with predictable growth? I would love to see more exploration of that question, though.

> It might be because earlier acquisitions are an easier exit than trying to become a self-sustaining company with predictable growth?

This is exactly it.

Had the same thought. Maybe money masks problems?

Equity is confusing and the various moving parts all matter. It's often difficult to know what % of the Company you own, but you are entitled to knowing the 409(a) valuation which is going to be equal to your strike price when your options are granted. As this increases, you have an opportunity to capture some value at some point if/when the company has a private market, is acquired, or goes public. I've always believed this process is personal and not one that "general guidelines" can always solve. Self-awareness is critical. https://www.vestboard.com/okta-inc-ipo-what-employees-should...

Links don't appear to be working to https://captable.io or https://angel.co/clear/how_much

Thanks! I really appreciate you letting me know; it's fixed now :)

(For the curious, I added a click mask to the modal contents and forgot to update the links to fire anyway.)

Shouldn't a TLDR about stock options include critical information like 83(b) election, etc?

That's probably in the too long tool people didn't bother reading.

That might be the "TL" part :)

"This simulation doesn't estimate taxation at all."

Well, then it's misleading.

Between AMT, capital gains / income tax, there's potential for a huge chunk of what you might earn to be removed.

I think the point is, "The number is probably not as big as you're thinking... oh and by the way, also even smaller because of taxes"

Hi Eric, Tiho, Marcus, etc.

This is a fantastic start. Yes, angel.co/clear was complicated. I hope you have better luck driving adoption.

What you are charting at the top is the company exit value. But the UI controls enter info tied to the employee. You should chart the employee's exit value.

You should also put the "or not*" controls as totally optional toggles as an exploratory UI. I.e. the user can toggle "preference" and see what it does to their value.

So taking the numbers at face value, we should be able to calculate the max acceptable cost you should be willing to incur to get those stock options. If you get, e.g. a 20% chance at a payout of 500 000 USD, not allowing for interest you might earn if applicable, or opportunity cost, whatever you need to do to get the options should not be worth more than 100 000 usd.

Reality is probably a little fuzzier than that, though.

Thank you to LTSE and everyone participating in this discussion. It is filled with GEMS of wisdom that a junior like myself is absorbing like a sponge.

Correct me if I'm wrong, but this seems to be assuming a seed round valuation of $40 million (it's returning $0 unless the exit is > $40m). That's absurd.

Edit: the assumption of 0.01% is also absurd.

A simplified calculator should include reasonable defaults. This is like a mortgage calculator called tldrCanYouAffordAHouse.com that assumes 25% interest rates and doesn't disclose that.

It assumes that the total amount of money raised over all rounds will be $41 million, rather than that the seed round valuation is $40 million. All the investors, whether they came in before or after the employee joined, will still get their money back before the employee starts to profit.

Why is the assumption of 0.01% absurd? From what I have seen, that's exactly what an early employee can expect. 10% of the available stock gets split between the early employees, most of which (9%) goes to the founders/c-suite. The other 90% is reserved for investors, of which the founder(s) may be one.

If you have 100 employees by the time you exit, and 1% of the stock was divided among them (exactly the situation where I am), each would get.. 0.01%. That is 0.0001 of the issued shares..... as options.

This is no longer uncommon.

That's not correct. The founders already have stock before any round. They typically don't get any of the ESOP. In early rounds the ESOP is essentially carved out of the founders stock, it doesn't make sense to give some of it to them (just negotiate a smaller ESOP). Also, founders are not considered investors in the sense you mention (different stock classes).

Secondly "by the time you exit" isn't relevant. Your stock is setup by when you join. If you join a company with 100 people, sure you get less. But 0.01% for Seed/A isn't even close. If that's what you get offered, don't take it.

Maybe add a field for salary difference vs 'expected market rate' and compute the amount of money you'd be looking at over six years investing the difference in something like a vanguard fund.

As an example - say you traded around 60k a year in cash in return for higher equity. In six years you're looking at around half a mil which means with, say .2 in a Series A, you're looking at a pretty big exit (i.e 700M) before you even have a chance of breaking even. This is obviously a terrible choice (i.e care for 20 dollars or a chance at 20 dollars)

To make it 'worth it', from an 'expected value' POV you'd need to make 2-3 million on around a 3.5B exit which are, of course, exceedingly rare.

You also have to be careful about things like options windows on exit, tricky term sheets with liquidation preferences for preferred shares, etc.

I'm going through this process now and it's shocking how most people really have no idea how this stuff works. Even with recruiters/HR/CTOs/etc who deal with this stuff day to day.

I'll​ never forget when a startup tried to poach me to be Employee #2 or 3 and refused to even match my previous salary and suggested that I really wasn't taking their equity (.15%, I think?) seriously enough. I told them that if they had a billion dollar exit in five years it still wouldn't bring me up to what I wanted, and then they said, "Well, all the tech guys we talked to said $YOUR_COMPANY overpays by 20%. We also think that we're spending too much time talking about money here and are worried you have the wrong priorities".

We also think that we're spending too much time talking about money here and are worried you have the wrong priorities"

That would make my blood boil. I'd probably say something like "if money isn't a big deal I'm sure you'd be fine to just give me some of your salary, right?"

After a few go-rounds the CEO literally offered me $5k/yr of his own money, but this was after I'd already told them I wanted $25k more, so…

I had a similar offer. $0 pay and maybe 1% equity. Sent them a spreadsheet explaining how inappropriate the offer was.

I had the very same offer. The founder made this big brouhaha about telling everyone he wanted to compensate the engineers "very well" to build his vision, and he made a point to say the compensation would be so much better than at a typical startup. The guy had a pretty big vision for a technical product/service that would need good engineers. I nibbled the bait and found out that his "amazing compensation" was $0 salary, and 1% options! Not even shares, just regular options. Yeah, let me sign right up for the "golden" handcuffs for zero dollars. It was infuriating that a veteran startup founder would make this lowball offer to employees (not even like cofounders). I've been working in startups for twenty years, so it was astonishing bullshit to me. I'm not sure how he was able to sign anybody else on. Needless to say, that company didn't make it more than eight months. The only team he could build was really heavy on the business side, and then a couple of (obviously) incredibly inexperienced developers.

Were any of you guys able to negotiate a better offer? I am in a similar position where I have been offered comparable salary but only 3% equity as the 4th member. Not sure it's worth giving up the job security without a higher stake.

I've negotiated with multiple founders and gotten several good offers, including $150k+ salary and single digit equity. The important part is not to fall in love with a company before an offer—a significant number of founders think engineers should work for under-market, and it's not worth talking with them.

If you have the time, Id appreciate advice. I was offered low 6 figures base salary plus 3% equity for a CTO role at a startup. I would be the 4th member Joining. As I know, there is a CEO bankrolling most of it, an expert in the field of the business who is taking little pay, and a marketing guy who is unknown but most likely taking some payment. Prior to the offer letter I built a prototype (out of contract) as a sort of demonstration I could do the job. However, I wish to be compensated for the rights to the prototype upon joining as it is about 50k lines of code. What would you do in my shoes?

> I was offered low 6 figures base salary plus 3% equity for a CTO role at a startup.

That's not an unreasonable offer. You should try to negotiate it up to around $150k.

> However, I wish to be compensated for the rights to the prototype upon joining as it is about 50k lines of code.

I'd suggest you mostly give up on that idea. It's naive thinking. The market value of this code is close to 0—it's very unlikely anyone else would want to buy it from you. At best, it's just an additional reason to hire you (instead of someone else).

I appreciate your insight. One thing I might add to bolster my reason for wanting compensation is that the prototype is critical to their business and without it they will be set back several months which they cannot afford. Furthermore, their vesting schedule gives them the potential to work me to death in the first year and then take everything I've built (past and future) and show me the door before anything vests.

On the other hand, if I walk, I might have wasted a few months time but at least I will have comparable salary in a stable job. 3% in early seed rounds just seemed pathetic to me when my role would be vital to the companies ability to grow.

It's not. If you are getting zero (or virtually zero) pay, you are a founder, not an employee. Founders usually get equal split.

Fyi to the site developer: I highly recommend giving the links at the bottom of the page their own routes, as clicking on one makes it impossible to use the browser back button and return to the main page.

I'm having trouble grokking the results here. If I put in 50 basis points for a seed-funded company it calculates as no return until a $40M exit. I'd like to see the justification for this.

It doesn't matter what percentage of a "seed company" I put, if it has a "low exit" (<$25M) I get $0... How is that possible?

Lots of investors have "Preference" which means they get a guaranteed minimum return on their investment. A rough example is like a 2x preference means when they put in $10M, the first $20M of the sale price goes to just those investors first . So if it sold for $20M, then everyone else gets $0.

Sorry if I missed something obvious, is the number averaged out per year or total over 6ish years? (nowhere mentioned on website or help link)

It's the total, and reflects all shares whether or not they are likely to have vested by then; vesting schedules vary widely, and hopefully are something people will be told about when getting their offer.

The answer is to start a startup. Before that, work at a startup. See if you like it. Specifically, work at a YC startup then apply to YC.

Does this include dilution?

Yep! That's part of what changes with the round: we assume a relatively-average dilution of 35% per round.


There's also another result: negative!

You could owe taxes on money you never saw. Under the AMT rules, if you exercise options at a discounted price, you have to consider the discount as "income". If several years later, when you're ready to sell and the stock is below what you paid for it, you'll still owe the taxes on your discounted price.

Ask your tax person for the details before engaging in any stock option purchase.

You will get credits to offset this in later years. It was far more painful after the Dotcom crash before the carry-forward rules were added.


Answer is $0

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