aveshcsingh

That's true. The only part of this post that applies generally is the discussion of golden handcuffs; the rest is specific to US tax law.

Excellent point, Chris. Founders should consider giving out RSUs instead of options for this reason. My understanding is that stock options do not count as Qualified Small Business Stock, however.

Glad you found it useful!

Thanks for the feedback!

What parts didn't make sense?

Thanks for the feedback! I do agree that holding employee stock could be part of an investment strategy. This post is geared towards the surprising number of people who hold employee stock as a result of a stock grant and without serious thought on whether they want to invest in their company.

What part of the risk premise is confusing?