3 ms·

Don't exercise until you can sell is great advice, but the giant wrinkle (particularly now that startups take far longer to go public) is if you don't wish to w

by x0x0 11y ago

Don't exercise until you can sell is great advice, but the giant wrinkle (particularly now that startups take far longer to go public) is if you don't wish to work for a company for 10+ years, you have a short exercise window after leaving a company. Some (very few) are converting ISOs to NSOs if you leave, allowing former employees to wait until the security is liquid before buying it. My suggestion to all engineers is to use the leverage you have and insist that vested ISOs convert to NSOs if you leave a company. If they don't want to do this, well, there's a reason, and it's not good for you. At minimum, they intend to crank those golden handcuffs tight, and if you have life changing events in the 5-10 years it takes a company to go public (want a house, partner wants to live somewhere else, kids, etc)... tough luck. If you continue even without a conversion clause, apply a massive discount (on top of the massive discount you should already be applying) to the "value" of those options. As for your anti-tax rant... if you want nice things (roads, schools, universities, clean air, judges, police, hospitals, child protective services, efficient postal mail, etc), someone has to pay for them. Charity is no substitute for our collective choice to pay for things.

chasing 11y ago
> As for your anti-tax rant... if you want nice things (roads, schools, universities, clean air, judges, police, hospitals, child protective services, efficient postal mail, etc), someone has to pay for them. Charity is no substitute for our collective choice to pay for things. Upvoting to support the idea that taxes as a concept aren't the problem, here. The problem is this obnoxious system of taxing things which likely have no value.
- georgemcbay 11y ago
  One of my huge annoyances with American politics is how few people seem to mind when large complicated concepts are conflated (often on purpose by people with vested interests in keeping the ideas confused). It sucks that giant multinational corporations can pay effectively zero taxes (or negative taxes thanks to rebate programs and such) and much of the population will support this simply because they don't like that a significant percentage of their income goes to taxes. Instead of "let's have corporations pay a fair share and me pay less" the message ends up "taxes are bad, let's not have any taxes!" (ignoring the rather obvious issue that without any sort of public funding the country would literally fall apart).
  - rdancer 11y ago
    > giant multinational corporations can pay effectively zero taxes That's not even remotely true. They may have zero or negative rate for some taxes, most often corporate income tax, but that's to be expected, when you have a rate of 35%(!). There are many other kinds of taxes, though, and the effective rate for any given corporation, or any sector, no matter how you slice the economy, is not going to be zero.
  - digbyloftus 11y ago
    Corporations are just collections of humans, which do pay taxes. The idea that they're a separate entity that is pulling one over us silly humans is ridiculous.
- avn2109 11y ago
  >> "...police, hospitals, child protective services,..." Wait, are hospitals taxpayer funded in America? If so, why do they charge my insurance such vast amounts of money for tiny services?
  - s73v3r 11y ago
    Some are, some aren't. Some are run by charities and churches, some by private companies. Many of these, especially ones in smaller, more rural communities, will receive government funds to help provide services.
  - zrail 11y ago
    Some hospitals are taxpayer funded. 2/3 of hospitals in the US are non-profit corporations. The rest are either public (run by the county or state) or are for-profit. https://en.wikipedia.org/wiki/Public_hospital#United_States https://en.wikipedia.org/wiki/Public_hospital#United_States
holman 11y ago
> Some (very few) are converting ISOs to NSOs if you leave, allowing former employees to wait until the security is liquid before buying it I care pretty deeply about this, and I want to start pushing more startups in this direction. I think the tide started turning in the last six months or so and more companies are allowing for a >90 day exercise window on NSOs, but it's still a pretty small club. I've been keeping a list in a repo, since I think it's important to help promote companies that are doing this for their employees: https://github.com/holman/extended-exercise-windows https://github.com/holman/extended-exercise-windows
ChuckMcM 11y ago
To be clear, I understand the value of taxes but I disagree with some of the taxes applied. AMT in particular hits a lot of people in the technology space disproportionately who are not good candidates for the moniker "tax dodgers". The target was "the rich" but when a tax policy bankrupts someone (as it did to people in the dot com crash, and will do to people in the unicrash) I disagree with it.
- x0x0 11y ago
  That's at least as much on the companies involved as the tax code. Companies are not only far better situated to understand the tax situation (wilson sonsini or fenwick make a living understanding/optimizing for it) but also have, and afaik always had, the choice to make employee-friendly comp choices such as turning ISOs into NSOs, giving RSUs in lieu of options, or perhaps even early exercise and 83b elections for all. It's fair to say that golden handcuffs aren't exactly making CEOs cry themselves to sleep at night, and it might be fair to say they even like them.
  - ChuckMcM 11y ago
    Except I'm not talking about CEOs who typically have packages which not only vest stock but pay the taxes for them. I'm talking about rank and file employees (like the Gilt employees in the article) who end up owing taxes, on gains they were never able to realize, which exceed their net worth. They are the ones that get pushed into bankruptcy when the IRS freezes their assets. The story I expect to read is probably an Unicorn employed engineer who exercises their options (perhaps this month) because they are leaving, and owes a huge tax bill come April 15th of next year, and by the time next year roles around their Unicorn is dead and they have worthless stock and a huge tax bill, and they are in debt because they borrowed money to exercise their option. The very definition of being 'upside down' in accounting terms. I'd love it if that doesn't happen, but given this story on Gilt I'm pretty sure we'll see more like it.
    - x0x0 11y ago
      I think I wasn't clear. I meant that, from CEOs' perspectives, the tax code is a feature not a bug. CEOs have the ability to work around this for their employees in multiple ways (NSO conversion, early/83b, RSUs, allowing sales via eg secondmarket) and don't.

by x0x0 11y ago

chasing 11y ago

> As for your anti-tax rant... if you want nice things (roads, schools, universities, clean air, judges, police, hospitals, child protective services, efficient postal mail, etc), someone has to pay for them. Charity is no substitute for our collective choice to pay for things. Upvoting to support the idea that taxes as a concept aren't the problem, here. The problem is this obnoxious system of taxing things which likely have no value.

georgemcbay 11y ago
One of my huge annoyances with American politics is how few people seem to mind when large complicated concepts are conflated (often on purpose by people with vested interests in keeping the ideas confused). It sucks that giant multinational corporations can pay effectively zero taxes (or negative taxes thanks to rebate programs and such) and much of the population will support this simply because they don't like that a significant percentage of their income goes to taxes. Instead of "let's have corporations pay a fair share and me pay less" the message ends up "taxes are bad, let's not have any taxes!" (ignoring the rather obvious issue that without any sort of public funding the country would literally fall apart).
- rdancer 11y ago
  > giant multinational corporations can pay effectively zero taxes That's not even remotely true. They may have zero or negative rate for some taxes, most often corporate income tax, but that's to be expected, when you have a rate of 35%(!). There are many other kinds of taxes, though, and the effective rate for any given corporation, or any sector, no matter how you slice the economy, is not going to be zero.
- digbyloftus 11y ago
  Corporations are just collections of humans, which do pay taxes. The idea that they're a separate entity that is pulling one over us silly humans is ridiculous.
avn2109 11y ago
>> "...police, hospitals, child protective services,..." Wait, are hospitals taxpayer funded in America? If so, why do they charge my insurance such vast amounts of money for tiny services?
- s73v3r 11y ago
  Some are, some aren't. Some are run by charities and churches, some by private companies. Many of these, especially ones in smaller, more rural communities, will receive government funds to help provide services.
- zrail 11y ago
  Some hospitals are taxpayer funded. 2/3 of hospitals in the US are non-profit corporations. The rest are either public (run by the county or state) or are for-profit. https://en.wikipedia.org/wiki/Public_hospital#United_States https://en.wikipedia.org/wiki/Public_hospital#United_States

holman 11y ago

> Some (very few) are converting ISOs to NSOs if you leave, allowing former employees to wait until the security is liquid before buying it I care pretty deeply about this, and I want to start pushing more startups in this direction. I think the tide started turning in the last six months or so and more companies are allowing for a >90 day exercise window on NSOs, but it's still a pretty small club. I've been keeping a list in a repo, since I think it's important to help promote companies that are doing this for their employees: https://github.com/holman/extended-exercise-windows https://github.com/holman/extended-exercise-windows

ChuckMcM 11y ago

To be clear, I understand the value of taxes but I disagree with some of the taxes applied. AMT in particular hits a lot of people in the technology space disproportionately who are not good candidates for the moniker "tax dodgers". The target was "the rich" but when a tax policy bankrupts someone (as it did to people in the dot com crash, and will do to people in the unicrash) I disagree with it.

x0x0 11y ago
That's at least as much on the companies involved as the tax code. Companies are not only far better situated to understand the tax situation (wilson sonsini or fenwick make a living understanding/optimizing for it) but also have, and afaik always had, the choice to make employee-friendly comp choices such as turning ISOs into NSOs, giving RSUs in lieu of options, or perhaps even early exercise and 83b elections for all. It's fair to say that golden handcuffs aren't exactly making CEOs cry themselves to sleep at night, and it might be fair to say they even like them.
- ChuckMcM 11y ago
  Except I'm not talking about CEOs who typically have packages which not only vest stock but pay the taxes for them. I'm talking about rank and file employees (like the Gilt employees in the article) who end up owing taxes, on gains they were never able to realize, which exceed their net worth. They are the ones that get pushed into bankruptcy when the IRS freezes their assets. The story I expect to read is probably an Unicorn employed engineer who exercises their options (perhaps this month) because they are leaving, and owes a huge tax bill come April 15th of next year, and by the time next year roles around their Unicorn is dead and they have worthless stock and a huge tax bill, and they are in debt because they borrowed money to exercise their option. The very definition of being 'upside down' in accounting terms. I'd love it if that doesn't happen, but given this story on Gilt I'm pretty sure we'll see more like it.
  - x0x0 11y ago
    I think I wasn't clear. I meant that, from CEOs' perspectives, the tax code is a feature not a bug. CEOs have the ability to work around this for their employees in multiple ways (NSO conversion, early/83b, RSUs, allowing sales via eg secondmarket) and don't.