[nwatson]

The rub is:

* the OP will need to pay a lot to buy their vested options when they leave each company

* the fair market value of common stock will have probably increased so they'll also need to pay immediate income tax on every gain

* they likely won't have a market for their shares until acquisition or IPO (five to ten to never years)

* the shares they do have will be diluted 10x or more through Series A/B through F, and they won't benefit from readjusted new 4-year-vesting grants

* they'll learn a lot and profit little from serial startup monogamy

[walterbell]

Try to join when stock has low paper value, exercise the options immediately so there is no gain and no tax. Then you vest shares, rather than options, and can take them with you.

[scurvy]

Not that many startups allow 83-b elections early on. It costs them a few $k when someone does this. It doesn't necessarily have to (it's just paper filed with the IRS by the employee), but that's what they're told and that's what they went through when they did their own 83-b paperwork. So that's what they think everyone needs to do. Honestly, there really aren't any legally required paperwork involved with 83-b, but the entire ycombinator crowd is convinced that there is. Perhaps it's bad knowledge by the YC figureheads?

[walterbell]

Since this affects 100% of startups and can have a huge financial impact on early employees, one would expect it to receive more attention. Since some startups allow the election, it is clearly possible. It needs to be a standard part of compensation negotiations. Early employees can obtain independent, professional advice on the topic, rather than burdening their friendly neighborhood VC.

http://www.stockoptionadvisors.com/isofaq/#83b

http://www.stockoptionadvisors.com/nqsofaq/vesting.shtml

[beagle3]

> Honestly, there really aren't any legally required paperwork involved with 83-b,

I've consulted with several good (by recommendation, and by their work on other issues) tax professionals, and each and every one stressed that without filing a 83-b election notice within 30 days of grant (and a copy with your returns) and paying the associated tax, you will NOT enjoy favorable 83-b treatment.

Do you claim they are wrong? How do you retroactively get 83-b treatment if you don't file in the first place?