The options given out at that time were priced at a $10B and have been basically under water since.

So even if you do join a fast growing company with a good brand and the potential to go public there's still a solid chance you make no money.

For those employees that did exercise their underwater options, one small silver lining is they can write those losses off on future tax returns.

Note this only applies to NQSOs not ISOs - since the gain in the ISO case is taxes as AMT; the loss can only be carried as an AMT loss and applied only if/when you are actually subject to the AMT.

It's possible to have RSU awards that vest without them being released to the employee. This means that (unlike exercised options) you can't sell them on the secondary market, but it also means that you aren't liable for taxes on an illiquid asset.

Note: I am basing this from one person who shared financial details with me, there may be a large variance in offers to different employees.

This means that ISOs can probably be exercised tax free, but NSOs require you to pay taxes on the spread from strike to the fair market valuation.

If your strike price is low enough you may be able to save and afford to exercise the ISOs, the NSOs will probably be too expensive with the tax burden.

There's also a 10yr expiration on options anyway so it's possible that you could lose them even if you're waiting for an IPO while holding unexercised NSOs.

In my experience, small startup options don't get exercised because of the tax bill, not because of the strike price.

You still have to watch out for the California AMT (which I didn't know about) - it's 7% and will still trigger at the lower value. As a bonus you can no longer deduct it either past 10k from federal taxes (though that may change with the charity thing).

The ability to do early exercise on unvested shares is also often not an option at startups so when you are able to exercise the spread is higher and the tax penalty is worse.

So if you don't foresee being at the company for at least 5 year or foresee having the money to purchase the options you have accrued after the 1+ years then you are better off asking for cash. Companies of course don't like this because it costs them nothing if they pay part of your comp in options that you then leave on the table when you leave the company. This is calculated, the companies know this.

How many startups can you expect to work in your career where you stay for 5 years? Lets say you work for which would be 20 years of your career. How many of those 5 are going to actually IPO? The math suggests you leaving a lot of money on the table. If you take the comp in cash you can put that money to work for you in other ways.

Personally I've made way more from stock options than I have from wages. Google stock has appreciated 7x since I joined in 2009, so you can do out the math for various fractions of equity compensation. And this was for a company where I valued that equity at zero, because it already had 20,000 employees, it was in the middle of the financial crisis, its stock was dropping like a rock, and 89% of employees were underwater in their stock options.

You could argue that if you take cash compensation, you could then invest that in public market stocks (like GOOG etc.), and there's a pretty good argument for diversification and not holding your net worth in your paycheck. OTOH, when it's your company stock, you also have an information advantage: for example, the press was very down on Google for most of 2009, thinking that they'd tapped out on growth and the web was basically over, and after the initial post-crisis bump it basically traded sideways until mid-2012. Having seen the energy there, the products under development, and the query growth rate numbers, I knew this wasn't true, but if you'd worked for cash in another company and then tried to invest in the public markets you would've had a very distorted picture of reality.

Not necessarily, it depends on what your strike price is.

>"Google stock has appreciated 7x since I joined in 2009"

The context was startups and IPO'ing. Google is neither a startup nor were you a pre-IPO employee.

But the point I wanted to make, bringing up the Google example, is that I didn't expect Google stock to have much upside in 2009. Most people didn't expect Google stock to have much upside in 2009. Google stock still had much upside. The excitement was all in Web 2.0 startups (like zillions of other people, I founded one), but most of them had little success. We're talking about Dropbox now, but Dropbox was a desktop app startup, perhaps the one thing less cool than a big tech company in 2008.

Similarly, the common wisdom now is that startups are a losing bet and you should go ask for cash at an established company that can pay you well. Usually, in markets, when something becomes common wisdom it ceases to be true. So I will happily take the opposite side of that trade - I'm back to founding a startup, I work for equity, and if people want cash, I'll pay them in cash. I realize that I'm making a risk/reward tradeoff here and there's a fairly decent chance my equity will be worthless, but I choose to make it anyway, because I believe that at this point in time, the startup career path is undervalued.

Yes of course that is just common sense and there is nothing in my comment that suggests you shouldn't apply common sense.

>"Nobody on an Internet forum can do that for you"

Well of course not and I was not attempting to advocate for someone else. I thought this was implicit when I stated "I think ..."

The employee got what they wanted (cash for their stock).

What infuriated me was that I had to do all the leg work and paper work and it was only when the money for the sale went into an escrow that the company rejected the offer. So they wasted a lot of people's time unfortunately - mine, the broker and the buyers time. The companies "preferred buyer" turned out to be some Hollywood big wig. And my guess is that they never had any intention of letting my proposed sale go through.

One curious thing I learned is that although this practice of selling options on the secondary markets by "worker bees" was strongly "discouraged" because it was seen as a sign of not believing in the company, it turns out the execs were all selling their options left and right and had been doing so for years.

ROFR isn't that bad. What is bad is some contracts have a call option on your stock at FMV price, even when you exercise.

https://www.wsj.com/articles/SB10001424052970203833004577249...

And you can't do it in an adhoc manner, it's usually organized by the company to one buyer.

That being said, read the options agreement carefully and ensure your interests are well protected.

It's worth noting that, in nearly all cases, you will not receive an options agreement until well after you have accepted the offer.

I've never tried to ask for an options agreement prior to accepting an offer, but I'd imagine it would be a very difficult thing to get at most companies.

Point is, negotiate a salary that meets your needs, and treat the stock options like lottery tickets, because that's what they are.

Using a 10% time-value-of-money discount, your stock options are only worth ~35% of their final monetary value when you first start out in the 10-year payoff case. That's not a 35% chance that you'll make something, that's the discount on what you do make. You still need to factor in the risk that you'll get nothing or a pittance, especially if we're talking early startup where the risk that you get nothing is probably somewhere in the 90% range. You don't have to come up with very unrealistic numbers in the current environment before you're looking at applying a ~95% discount to your hopes on what your stock options might be worth in 10 years.

(IMHO, working at a startup when you're young for some hard & fast experience, if you can afford it, is possibly still worth it, but at this point in 2017, early engineers should be demanding either cash or founder-level equity grants. An in-between grant that may pay out $100,000 in ten years may sound grand from the perspective of someone about to receive that payout, but from the front-end you should value it somewhere around $5K or so, and I wouldn't fight anyone who wants to pick numbers to push that lower. On an annualized basis, $5K is more like "a minimal raise" than a reason to work at a company.)

Money today is worth more than money tomorrow, and often the lump sum of money you get at the end of a startup’s liquidity event as an employee is not much greater than someone who earned money through a more traditional route, if you even get it. I know people who chased the startup life for years with nothing to show for it.

A decade later when they finally give up and resign to a more traditional career path, their cohorts who started down that path a decade ago are now impressively far ahead of them in life. I’m talking big houses with long hallways and a baby or two keeping them up at night while they ascend the ranks of a “real” company during the day.

So when playing the startup game, the only thing on your mind should be “fast money, fast money, fast money!”. If you like to see businesses that have been around for way longer than 10 years and building strong revenue that most startups can only dream of, don’t look for startups.

The standard pitch (that many recruiters abuse) was that your options would become real in 4 years but the reality is this is closer to a decade. If companies were marketing their options realistically instead of selling them like snake oil the 10 year point would be fine.

I remember interviewing with an almost unicorn and their VP of engineering literally tried to pitch their options by telling me to assume the company would IPO at XXX price within 4 years. No mention of opportunity costs, tax issues, liquidity issues, etc. He even forget to consider the strike price when "helping" me ballpark the benefit. And everyone seems to forget there is thing called the discount value of cash - $200K in 10 years is not the same as $200K in 5. It's been 2 years since I got that unicorn offer and I can say that the company is at a minimum still 4 years away from an IPO.

Stop selling the snake oil and people wouldn't be unhappy when there is a decade long payout time.

But more to your point, recruiters lie, and if you don't realize that as a grown up, college graduate, you've got bigger problems in your life, I suspect, than when a company decides to file IPO. They shouldn't lie, but recruiters tempting you with options also isn't a reason to suddenly submit to the SEC and public traders to get some cash.

So in practice, employees are shackled to the company until IPO happens.

(Note: some more progressive companies have been combating this dynamic a number of ways -- I don't know if Dropbox is among them)

Customers.

But the AMT/exercising problem can be severe if you're unlucky.