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.
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)