This is a useful watch for a first or second time entrepreneur, or a new startup employee.

Some points:

If you raise a round at a high valuation, and don't significantly raised your valuation. You may have put yourself in trouble ("Down Round").

The anti-dilution protections are often so egregious that companies will often rip up the cap table and start from scratch. ("Recapitalize", ouch)

Founders (especially) and employees should ALWAYS file their 83b elections if they have the $. [File in duplicate, imo].

His ebook is available here on Scribd.

On 83b elections.

It makes sense to file ASAP when valuation is low or the employee or partner is one of the first few people: http://ayrlaw.com/what-is-an-83b-election-and-when-do-i-make-it-part-1-with-graphic/

However, if a company has a high valuation (likely a larger company) and still has an uncertain future then filing an 83b election can cost more. http://ayrlaw.com/what-is-an-83b-election-and-when-shouldnt-i-make-it-part-2-with-new-graphic/