For example, I was a jr. engineer at a stage A $5 million startup with ~%0.4 of the company in stock options. When it reached its $1 billion valuation 4 years later, my options with dilution were worth x25. But $500k/4 years is $125k/yr, which is pretty close to the stock compensation working at google. But these options were not cash equivalent like google's stock, and I had to drop it all on the floor because of the 90 day window. I lost $500k in compensation because I decided to work at the startup vs. google.
Imagine if your employees had a good amount of savings and could easily afford the $10-20k it costs to pre-exercise their options in your infant stage startup. Then these rules are pretty moot. It takes advantage of people who don't have the money to pre-exercise options, who tend to be younger people.
Also it's unfair, investors can diversify their income sources, while employees cannot.
I have to say that's a heck of a lot of dilution, too. 200x growth in valuation vs. only 25x in your stake? What's that, over 85% dilution?? Sounds like that juicy unicorn valuation was only achieved by a lot of fundraising rounds under presumably not awesome terms. Not that that makes you feel any better.
I'm thinking there should be some kind of extra incentive for early stage teams to stick together, but with a more explicit maturity point. It used to be IPO/acquisition. Now that IPO is often farther off there should probably be some other metrics. What are they? Valuation? Number of employees? Length of employment? Revenues? Some combination?
US startup stock options push the tax externality to their employees. In somewhere like canada, your tax bill is due at liquidation, not at the purchase of options. It makes a lot more of this problem go away. For most early stage employees that do well in a tax scheme like canada's then paying $20k for stock in a large valuation company isn't nearly as painful as paying $20k + $100k in AMT tax.
I think that would probably be reasonable for most angel investment and stage A teams. It isn't a stretch for the company to pay an extra $10-30k for a stock transaction where %60 of it cycles back to them anyway for a total of $4k-12k of a tax bill.
Also another way to value the stock to give to early employees is to treat them as investors investing the $500k+ or whatever equivalent they are giving up for 4 years and giving them that as their stock where you foot the tax bill. Also giving them the same visibility and protections that those equivalent angel investors would get.
The percentage points you start giving up for that although starts becoming too large for most founder's tastes, and thus we get the current situation we have today. Many engineers tell themselves, why should I join an early stage startup when I can do so much better as a founder with a similar risk profile?
I realized you want a way to keep the golden handcuffs that are unique with the US tax law and current equity structure to incentivize poor-ish early employees to stick around without creating an incentive to fire them with back loaded options.
You could create a second stock option reward for the early employees with a company performance + time condition vesting condition and pay the tax bills by giving them the stock right away.
Pinterest's long term stock option expiry date is contingent on being with the company 2-3 years, otherwise it goes back to the same 90 expiry window I think.
You could try many structures, and the market will respond to it compared to their other offers. A good way to start is to explicitly state what you actually want, and then engineers could state what their price is for that ask in comparison with what they can get.
But then it's hard to set a definite timeframe. What you want is to incentivize sticking together as an effective team to reach a point of maturity, to maximize the chances of getting there and thus the options being worth anything. It's probably more about size and valuation. That's what was nice about effectively tying it to IPOs (when IPOs happened earlier). Going public was a decision that the board made when they company was "ready".
The engineer market in SF right now is very highly heated, and this kind of incentive makes an offer from pinterest far more appealing. That and people are starting to compare notes and make articles on medium and others really spelling it out is probably hurting recruiting and this is coming out as a response.
You should be able to:
1) Get a loan from somebody who wants in on the startup to exercise the option.
2) Exercise option.
3) If company decides to buy back option via first right of refusal you return the loan plus a nominal increase and you pocket the difference in valuation between rounds minus the loan fee. If the company lets you sell it to the person than they get the equity in return for their early payment.
Do most stock grants disallow this transaction? Or is there not much of a market for these sort of third party buyers?
You also have to get a lot of paperwork together, that you usually don't have and it can take months as the company drags it's feet in giving it to you. There wasn't paperwork preventing this at the company I was at.
If anyone is thinking about a startup offer, I would suggest getting equityzen's documentation checklist upfront. It can take longer than you think, and a few months later, people who were interested in buying might not be anymore.
I was trying this a little less than a year ago, so it isn't as correlated to the current issues today.
Also I would try to get the stock paperwork agreement that they will have you sign for your options. Very surprisingly, for even some big superstars today it is very hard to get this from them until you start working for them. There can be hidden gotchas like after exercise stock buyback options at the current FMV. Or restrictions that even stop you from doing things like ESO fund.
Although, one trope about startups is that they usually pay crappy, so the likelihood of any given employee having significant savings is low.