I don't for a second claim to know the special tax nuances of...

I don't for a second claim to know the special tax nuances of these systems, but just going by the basics with some reasonable assumptions, Marks case is probably something like this:

• Company issues 4m shares worth $5,360,000 (say $1.34 per share)

• Mark pays $4,480,000 ($1.12 per share) for the 4m shares.

• The instant benefit/discount and assessable income is $880,000
• The new shares are worth up to $5,360,000 before any CGT is paid, so it's still a very good deal.

He could have easily liquidated some of those shares immediately to pay the tax, quick and simple. Probably what the vast majority of people do? Have said it before but it really is a strong sign of confidence, going through this much trouble to keep all of the shares. Time will tell if it's genius or crazy!