Wow, such a great read. I love people who are so open and honest. btw, how does tax work in the US for acquisitions? is the money he's getting is taxed the same as income?
If the business is >1 year old, it's treated as capital gains. Since the company is >5 years old, he can likely take advantage of the Qualified Small Business Exemption up to $10m and pay no federal taxes.
https://www.investopedia.com/terms/q/qsbs-qualified-small-bu...
Decent link here: https://www.svb.com/blogs/svb-private-bank/understanding-qua...
I believe, but can’t find, that you need to trade cash for the shares to qualify, so if your basis isn’t zero, it might require writing a check into the entity to cleanly qualify.... moral of the story here is pay someone to help you on this :)