6 ms·

Right, but the only reason you'd take on any dilution as a founder is if you think the extra money will make your shares more valuable in the future.

Swizec 9y ago
The issue is that as an employee you don't have that choice. Somebody else makes those decisions for you, you're just along for the ride.
- sillysaurus3 9y ago
  The VC-backed company model isn't set up for employees. The model is so that (a) founders can take risks (b) using money from VCs (c) where if the company does well, the founders and VCs both become richer. Everything else follows from that. The fact that employees get any shares at all is just a way to get better employees so that the company does well. Only employees of unicorns have any chance of getting wealthy from stock, and you're unlikely to be an early employee of a unicorn. It's better to view the situation in absolute terms rather than relative terms. Instead of comparing the outcomes of founders/VCs vs employees, compare an employee of a startup to an employee of non-startups. At not-startups, the working environment is very different. Some people enjoy that, some prefer the opposite. Also, getting +$100k (or +$50k, or even just +$10k) is still nice, even if the founders and VCs get 800x more. The only part I have serious concerns about is the fact that you can end up underwater when it comes time to exercise your options, i.e. your tax bill outweighs whatever profits you'd see. I don't know exactly how this situation arises, but it happened to a friend. It was something like: he could have exercised his shares and gotten several hundred thousand, but he would've needed to pay about $100k in taxes beforehand. Since he didn't have that money, he couldn't exercise the options. I might be wrong about the specifics, but there are situations similar to that, and it's pretty unnerving knowing that you can jump into a situation where your +$100k somehow turns into -$50k.
  - swolchok 9y ago
    > he could have exercised his shares and gotten several hundred thousand, but he would've needed to pay about $100k in taxes beforehand. Since he didn't have that money, he couldn't exercise the options. I feel like at least a phone call to a bank would be in order at that point. If it's that simple, surely some sort of mutually agreeable loan could be worked out.
    - pbhjpbhj 9y ago
      Couldn't you bootstrap it, get £5k on a credit card for the taxes to exercise some of the options, use the profit to pay the taxes on the rest (or a further bootstrap)?
      - dmoy 9y ago
        If the shares are not liquid 'cus the company is still private, then no you can't.
        pbhjpbhj 9y ago
        But the Revenue consider you to have received value in that "piece of paper" that you can't liquidate? That just seems like perverse tax law - why is it that way? Surely if they're private shares that can't be sold the extrinsic value is zero, the private share value for tax purposes is no greater than the value of the option?
  - kbenson 9y ago
    > it's pretty unnerving knowing that you can jump into a situation where your +$100k somehow turns into -$50k. But even your example wasn't that. Your examples was -100k and +300k (or more), but offset by time slightly. That's still a very large net positive, just gated by a period of net negative. I suspect there are some details that you are missing as to the situation of your friend. I know little about investment vehicles, but I've filed taxes at one point and paid them at a later point many times. For income taxes the rules for this are clear, and the amount you pay in fees and interest is also very clear. For some investment vehicle, I would bet if there's some taxes that need to be paid prior they have automated processes set up to pay them for you and take the amount out of the later payout, for a fee. If not, I can't imagine getting a short term loan for that would be too hard, even if you have to use private money (a real investor, or even just a friend).
    - sillysaurus3 9y ago
      Yeah, I'm certain I got some of the details wrong. It sounded like a situation similar to https://news.ycombinator.com/item?id=14464184 https://news.ycombinator.com/item?id=14464184 where you can owe taxes on money you never saw.
    - kristianc 9y ago
      It depends heavily on if there's any prospect of your shares becoming liquid any time in the near future.
  - mnglkhn2 9y ago
    > The VC-backed company model isn't set up for employees. The model is so that (a) founders can take risks (b) using money from VCs (c) where if the company does well, the founders and VCs both become richer. Does this mean that stock options are not a measure of risk taken by the employee into the company? You mean the stock options are just like cash? I didn't think so. The employee is invited to take risks but without the protections.
  - rhizome 9y ago
    or even just +$10k As someone who has been exactly there, this doesn't compensate for the lower salaries that are de rigeur in startups. Not to mention being an absolute insult compared to the employee's degree of contribution to the resulting event. "Better than nothing, or being underwater" is pretty thin gruel in practice.
  - sokoloff 9y ago
    > Only employees of unicorns have any chance of getting wealthy from stock, and you're unlikely to be an early employee of a unicorn. Define wealthy. I have done quite well (not FU, 3-comma money, of course, but solidly 2-comma) from equity as an employee. In my current company, I joined a few months after the Series A (so nowhere near "early"), stayed through the IPO and many years of growth past that. We were never a unicorn. Amazon, Facebook, and Google are regularly turning SWEs into millionaires and a substantial part of that is from equity. Microsoft also had a good decade and a half of doing that. Netflix probably does as well. (OK, Facebook was a unicorn; the others probably weren't ever called that, though it may have fit.)
- theptip 9y ago
  I'm not sure that's particularly relevant to this thread; there are plenty of decisions that materially affect the value of your equity that you have no say in. That's true both in a startup and at a large tech company like Google where a significant part of your comp is in RSUs. The point in the GP post that I was expanding upon, > It's zero net gain at the point of dilution. is focussing on the wrong instant in time. You should be calculating the effect of the dilution on your exit event, when your equity actually becomes exchangeable for money.
- deleted 9y ago
  [deleted]
- rocketraman 9y ago
  Which should have been clear to you when you joined the company and read and signed the employment and stock options agreements (you did read them, didn't you?). If that isn't to your liking, don't work for a startup.
  - s73ver 9y ago
    "It's in the contract!" is a poor excuse for the company acting shitty to you.
    - rocketraman 9y ago
      You miss the point. I don't think they are acting shitty. They're acting according to what both you and they agreed to in advance. You knew (or should have known) what they were (and were not) going to give you in return for your effort. It's only shitty of them (and illegal) if they don't follow through on that agreement.
      - s73ver 9y ago
        And I disagree.
- fuckemem 9y ago
  A bit like owning stocks on the stock market then I would guess. Which begs the question of whether to take a higher paying job with no options and invest the difference.
gesman 9y ago
Or to prolong inevitable death.

Swizec 9y ago

The issue is that as an employee you don't have that choice. Somebody else makes those decisions for you, you're just along for the ride.

sillysaurus3 9y ago
The VC-backed company model isn't set up for employees. The model is so that (a) founders can take risks (b) using money from VCs (c) where if the company does well, the founders and VCs both become richer. Everything else follows from that. The fact that employees get any shares at all is just a way to get better employees so that the company does well. Only employees of unicorns have any chance of getting wealthy from stock, and you're unlikely to be an early employee of a unicorn. It's better to view the situation in absolute terms rather than relative terms. Instead of comparing the outcomes of founders/VCs vs employees, compare an employee of a startup to an employee of non-startups. At not-startups, the working environment is very different. Some people enjoy that, some prefer the opposite. Also, getting +$100k (or +$50k, or even just +$10k) is still nice, even if the founders and VCs get 800x more. The only part I have serious concerns about is the fact that you can end up underwater when it comes time to exercise your options, i.e. your tax bill outweighs whatever profits you'd see. I don't know exactly how this situation arises, but it happened to a friend. It was something like: he could have exercised his shares and gotten several hundred thousand, but he would've needed to pay about $100k in taxes beforehand. Since he didn't have that money, he couldn't exercise the options. I might be wrong about the specifics, but there are situations similar to that, and it's pretty unnerving knowing that you can jump into a situation where your +$100k somehow turns into -$50k.
- swolchok 9y ago
  > he could have exercised his shares and gotten several hundred thousand, but he would've needed to pay about $100k in taxes beforehand. Since he didn't have that money, he couldn't exercise the options. I feel like at least a phone call to a bank would be in order at that point. If it's that simple, surely some sort of mutually agreeable loan could be worked out.
  - pbhjpbhj 9y ago
    Couldn't you bootstrap it, get £5k on a credit card for the taxes to exercise some of the options, use the profit to pay the taxes on the rest (or a further bootstrap)?
    - dmoy 9y ago
      If the shares are not liquid 'cus the company is still private, then no you can't.
      - pbhjpbhj 9y ago
        But the Revenue consider you to have received value in that "piece of paper" that you can't liquidate? That just seems like perverse tax law - why is it that way? Surely if they're private shares that can't be sold the extrinsic value is zero, the private share value for tax purposes is no greater than the value of the option?
- kbenson 9y ago
  > it's pretty unnerving knowing that you can jump into a situation where your +$100k somehow turns into -$50k. But even your example wasn't that. Your examples was -100k and +300k (or more), but offset by time slightly. That's still a very large net positive, just gated by a period of net negative. I suspect there are some details that you are missing as to the situation of your friend. I know little about investment vehicles, but I've filed taxes at one point and paid them at a later point many times. For income taxes the rules for this are clear, and the amount you pay in fees and interest is also very clear. For some investment vehicle, I would bet if there's some taxes that need to be paid prior they have automated processes set up to pay them for you and take the amount out of the later payout, for a fee. If not, I can't imagine getting a short term loan for that would be too hard, even if you have to use private money (a real investor, or even just a friend).
  - sillysaurus3 9y ago
    Yeah, I'm certain I got some of the details wrong. It sounded like a situation similar to https://news.ycombinator.com/item?id=14464184 https://news.ycombinator.com/item?id=14464184 where you can owe taxes on money you never saw.
  - kristianc 9y ago
    It depends heavily on if there's any prospect of your shares becoming liquid any time in the near future.
- mnglkhn2 9y ago
  > The VC-backed company model isn't set up for employees. The model is so that (a) founders can take risks (b) using money from VCs (c) where if the company does well, the founders and VCs both become richer. Does this mean that stock options are not a measure of risk taken by the employee into the company? You mean the stock options are just like cash? I didn't think so. The employee is invited to take risks but without the protections.
- rhizome 9y ago
  or even just +$10k As someone who has been exactly there, this doesn't compensate for the lower salaries that are de rigeur in startups. Not to mention being an absolute insult compared to the employee's degree of contribution to the resulting event. "Better than nothing, or being underwater" is pretty thin gruel in practice.
- sokoloff 9y ago
  > Only employees of unicorns have any chance of getting wealthy from stock, and you're unlikely to be an early employee of a unicorn. Define wealthy. I have done quite well (not FU, 3-comma money, of course, but solidly 2-comma) from equity as an employee. In my current company, I joined a few months after the Series A (so nowhere near "early"), stayed through the IPO and many years of growth past that. We were never a unicorn. Amazon, Facebook, and Google are regularly turning SWEs into millionaires and a substantial part of that is from equity. Microsoft also had a good decade and a half of doing that. Netflix probably does as well. (OK, Facebook was a unicorn; the others probably weren't ever called that, though it may have fit.)
theptip 9y ago
I'm not sure that's particularly relevant to this thread; there are plenty of decisions that materially affect the value of your equity that you have no say in. That's true both in a startup and at a large tech company like Google where a significant part of your comp is in RSUs. The point in the GP post that I was expanding upon, > It's zero net gain at the point of dilution. is focussing on the wrong instant in time. You should be calculating the effect of the dilution on your exit event, when your equity actually becomes exchangeable for money.
deleted 9y ago
[deleted]
rocketraman 9y ago
Which should have been clear to you when you joined the company and read and signed the employment and stock options agreements (you did read them, didn't you?). If that isn't to your liking, don't work for a startup.
- s73ver 9y ago
  "It's in the contract!" is a poor excuse for the company acting shitty to you.
  - rocketraman 9y ago
    You miss the point. I don't think they are acting shitty. They're acting according to what both you and they agreed to in advance. You knew (or should have known) what they were (and were not) going to give you in return for your effort. It's only shitty of them (and illegal) if they don't follow through on that agreement.
    - s73ver 9y ago
      And I disagree.
fuckemem 9y ago
A bit like owning stocks on the stock market then I would guess. Which begs the question of whether to take a higher paying job with no options and invest the difference.

gesman 9y ago

Or to prolong inevitable death.