Earlier quoted context omitted.
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.
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, bu…
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?