When I started my new job at a startup about a year ago, I started getting about a third [1] of my pay in stock options. Being risk neutral in donating, I decided to spend my salary on me and donate any proceeds from my stock options. This let me increase the fraction of my pay I was giving away without decreasing what I keep. Mathematically and economically, considering just what I can give, I think this was the right decision.

The problem is, much of my potential impact is from convincing others to give, and if I have to talk about stock options, expected value, and money that I intend to give away it's confusing and distracting. Things were much simpler when we could just say "we lived on about $22,000 and gave about $45,000". Should I switch back to giving money?

It would not be an easy switch. Options represent a small chance of a lot of money, and they're not very valuable to me personally. (Each additional dollar is worth less than the last). If I were to start giving a third of my compensation away as cash, that would be about 2/3 of my paycheque [2]. Which would be pretty hard. Maybe I should donate some combination of cash and options?  Making this more complicated, I had negotiated more options in exchange for a $10K lower salary, figuring that for money I was giving away this was the right thing to do.  Suggestions?

[1] You might say "how can you say 'about a third' when you have no idea whether your stock options will even be worth something ever?" What I did was estimate how likely I thought Cogo Labs was to be worth $X in about ten brackets ($0, $10M, $50M, ...), and then calculate an expected value as $0*P_1 + $10M*P_2 + $50M*P_3... Then I multiplied by the fraction of the company whose options would vest to me each quarter, and got something about half my quarterly salary. So: one third of compensation.

[2] It's 1/2 my salary (the last third is options) but 2/3 of takehome pay because 1/6 of my pay goes to taxes and other paycheque deductions.

(I also put this up as a blog post)

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Orthogonal to the risk issue, but still important when donating, is that nonprofits are exempt from capital gains taxes. This means that if you happen to end up with stock that has appreciated since you got it, you should give stock before you give dollars; and if you have stock that has depreciated, you should keep that before you keep dollars, since selling it will offset other taxes. I believe Fidelity has a special fund that lets you transfer ownership of stock, sell it without capital gains, and give the charity dollars with no extra overhead for them. Other brokers probably do too.

Re: charitable gift funds. Fidelity calls it the Charitable Gift Fund, I know there are similar funds managed by other places. The way it works is that you transfer your appreciated stocks to it and take the tax deduction in the year they are transferred. Fidelity sells the stock and you elect which of their funds (growth, bonds, etc.) the proceeds should be invested in. When you wish to donate to a charity, you go online and direct Fidelity to make the donation. It must be to a 501c3 approved charity and a minimum of $50 must be donated. It's as quick and easy as writing a check and you can make the donation anonymous if you wish. Fidelity does collect some management fees for the service, but they aren't very high.

The problem is, much of my potential impact is from convincing others to give, and if I have to talk about stock options, expected value, and money that I intend to give away it's confusing and distracting.

Is this based on actual experiences?

It's not. When I imagine trying to respond to a question of how much I give, I'm worried by the difficulty of explaining what I'm doing. This would be especially hard with a radio show or something where I'd be unable to gauge audience reaction, though I don't think I'm likely to be on one.

It may have kept me from bringing up numbers in cases where they would have been relevant, and it has definitely kept me using 2009's numbers, when I need numbers, instead of more recent estimates.

I think there are effective ways to describe this, especially to the potential-entrepreneur/technology audiences that may represent a lot of your potential weighted influence. You can talk about how more and more successful entrepreneurs like Mark Zuckerberg and Bill Gates have been taking the Giving Pledge: when you succeed in a big way you can help people immensely, even donating most of your wealth, without impacting your lifestyle. So you are going to try for big payoffs via stock options or startups and give them to help others. There are dangers with some audiences that this will the impression that do-gooding is only for the rich, but that can be managed too.


Your situation seems somewhat similar to if your job paid you in a combination of cash and lottery tickets and you decided that you would keep the cash for yourself but donate the winnings of the lottery tickets to charity. As such, your charity dollars vary year to year, but they average about 1/3 of your pay.

I don't think that's a perfect explanation (Options are not equal to lottery tickets) but I don't see any large inferential gaps in it. And I think people are more likely to understand lottery tickets than they are to understand options, so the chances of this being difficult to explain seem likely to be lower.

To confirm this though, are there any large differences between options and lottery tickets that would hurt the quality of this explanation on a quick level (as opposed to a detailed level)?

As an explanation I'm not sure cash+lottery would work well, because people might respond by thinking "oh, that's nothing like how I'm paid" or "if I start getting paid in some combination of cash and lottery tickets I could give away the lottery tickets too".


I reread your post, and I realized why it didn't seem like you had enough focus on inspiring people. Rather than drawing attention to options as a percentage of your salary, focus on this part here:

"I had negotiated more options in exchange for a $10K lower salary, figuring that for money I was giving away this was the right thing to do."

I seem to have either entirely missed this the first time or skimmed and not parsed it, so I am going to repeat it in caps in case anyone else also didn't notice this.


I realize you mentioned that you have already used the line "we lived on about $22,000 and gave about $45,000" article, but I didn't quite parse that either, (perhaps I need to read slower?) so I'm also going to repeat that in caps as well.


That I managed to read your post without somehow having these facts click is probably a small amount of evidence that yes, drawing people's attention to options is a mistake, and you were correct to worry about this!

Additional details on how you decided to take a large paycut for charity would probably make an good focus for inspiring further charity. While not everyone has options, anyone CAN decide to donate a chunk of money off of their yearly salary.

(To be fair, the 'we' for the donation above is me and julia together.)

Do you have suggestions for how to say "I give a lot of money to charity, I hope this inspires you to do similarly" in a way that doesn't make people suddenly stop listening? Unless I downplay the giving, I think people see me as proselytizing.

I'd be very surprised were there a one-size-fits-all answer to this. What encourages action for one type of listener will likely discourage it for another. Define your target audience and tailor your message to them.

I think getting an idea of what works is going to require talking to a lot of people.


To be honest, I'm not my advice is going to be more convincing then what you already do. You seem to be doing an excellent job of being humble as opposed to proselytizing at least to me (such as in your caveat above that Julia also deserves credit.)

It is possible (I don't know how likely this is in your case) that attempting to focus too hard on sales techniques can actually backfire if the people who you are attempting to convince are too aware of sales techniques. For instance, after a long spree of consecutive contractor visits, I started to notice certain thematic elements. At one point, I'm pretty sure I had someone leave just because he used a certain sales tactic (I think it was 10% off, but only today!) simply because what might have been convincing under ordinary circumstances seemed like a transparent attempt at manipulation after being exposed to it repeatedly and I didn't even care whether or not his product was worth it.

I would say the only advice I can give you is to not give up. As you mentioned to TheOtherDave, getting an idea of what works is going to require talking to a lot of people. Getting shot down will be discouraging, (In fact, it will probably feel MORE discouraging than you expect, even if you take this into account) but you will want to convince yourself realize that it's better to just move on then spend time moping about it. Also, as someone who has spent time moping, I've found that moping doesn't necessarily feel like moping when you are moping. It would be a good idea to have someone else who could keep an eye on your emotional state during these attempts to note if you seemed to be moping to a more outside perspective.

I think that those pieces of advice (Don't give up, trust in your friends!) Are sort of generic advice that fits a large number of occasions though. Sorry I can't give you more helpful advice, but my record doesn't seem to contain evidence that I am usually that convincing.

Slightly off-topic: thinking that this argument is convincing is a typical mind fallacy. "Oh, good, someone is pulling extra weight, this means that I can slack off" would probably be just as common a reaction.


First of all, you are correct and I should have reflected that in my post.

Second of all, I suppose I didn't actually find the argument convincing either. If I had, I would have actually donated money to charity in response to being impressed. I CONSIDERED donating money to charity and was very close to doing so, but I decided not to. I doubt I'm explicitly aware of all of the reasons for that decision, but the fact that I recently went below the minimum without fees on my savings account is the first one that came to mind, but I don't know if that's really my true objection.

So including all caveats of which I am currently aware, if someone was in a mental position like mine, and had not recently had any financial trouble, and did not have any other objections, they may have donated.

However, I don't actually like this argument, because it doesn't feel sufficiently inspirational. And while I can think of those caveats NOW, at the time it seemed like I was actually very close to being convinced in a way I don't think that list of that criteria reflects. So I end up liking the connotations of my previous remarks even though the denotations of my current remarks seem more accurate.

Sorry. This is somewhat confusing. I don't really seem to have a good way of discussing ADBOC points even when they are my own points.

You might not want to reveal to your coworkers that you have decided to donate the option money. The whole point of giving away stock options is to incentivize people; that incentive is undermined if the employee gives away the upside.

Well, if you are giving away money you are suggesting you value marginal dollars going to your charity of choice just as much as you value marginal dollars going to you. So if your coworkers also believe you are a perfect consequentialist unconcerned with signaling then you are fine.

I am assuming you need to exercise the options and then donate the stock, or the proceeds from the sale of the stock.

If your options are (USA law) NQSO, non-qualified stock options, then 1) there is essnetially no difference between donating cash and donating stock/proceeds 2) you are most likely making an expensive mistake in not holding the options till much closer to their expiration date.

If they are qualified stock options, then 2) would still apply, but I do not know about QSOs and their tax/charity treatments.

Options have a "time value" and if your options were tradable, you could sell them for significantly more than the value you get from exercising them and selling or keeping the stock. That options granted to employees are NOT tradable means the only way to realize the "time value" is to keep the options until close to their expectation date.

That your personal utility for additional dollars is lower as you get more is probably irrelevant or irrational in the case where you are donating to charities. Pretty clearly there are plenty of charities that have utility functions for recieved dollars that are nearly completely linear over the range of values you are talking about. It would seem, then, that you should have something pretty close to a linear utility associated with the dollars you give to these charities.

Cheers, Mike

I'm sorry, I wasn't clear. I'm not thinking about selling the options prematurely to turn them into donateable money sooner. I'm considering shifting from my current "all salary is mine, all options are to charity (eventually)" to "some salary is mine, some is to charity, all options are mine" (or somewhere in between).

See also this.