He says it cost him $100m. Is that because of the stock options he lost when he was fired?
To have $100m in stock - he would have been a very early hire?
To have $100m in stock - he would have been a very early hire?
How does having to pay a tax make things easier?
It's a serious problem in California. When you are granted options at $1 and the company IPOes with a valuation of $100 per share, all employees who have exercised their options are reputated having made a $99 gain. So they have to pay, say, $30 per share. But it's so virtual money, because they may not have $30x number of shares in cash. So those people are forced to either borrow money or sell their shares to pay their taxes. Worse: Employees often aren't allowed to sell during a lock-in period after the IPO, and they can't sell their shares at all before the IPO. So they are constrained to borrow. Worse: If the company loses momentum and comes back to $1 the next year, then they can't get reimbursed for the $30 tax they paid. So they're in for $29. Per share.
Compare that to Australia. If an Atlassian employee was granted stock options, they only have to pay the CGT when they sell. It didn't matter that Atlassian went IPO in 2015, or that shares changed hands when the administrative location was moved to UK circa 2013 (which could have been considered an exit event in US). If employees keep their shares until 2080, they'll only have to pay the CGT in 2080 with the money they got from selling.
Disclaimer: I'm not a financial adviser and I'm not saying that employees should sell their shares.
As a side note, shares go from $1 to $10 partly because the company gets better than expected, and partly because they don't give dividends to employee-issued shares. A share valued $100 one year and $104 the next year is the same thing as another one which stays at $100 and gives you $4 dividends.
You're describing AMT, and the reason it exists is to account for an obvious behavioral pattern, which is never to sell. The pattern gets more attractive with increase in wealth, as loans against the public securities pledged as collateral are widely available at sub-1% in current rate environment, e.g. https://www.interactivebrokers.com/en/?f=interest
While risky (with margin calls and what not), a loan against small portion of the portfolio is pretty tax-efficient, as loan proceeds are not income and are not capital gains.
If what you're describing in Australia is correct, my guess is that it's a bug in Australian tax system, not a feature. Wait for a few multi-millionaires or billionaires to prop up, never sell a single share of their portfolio while making their living through portfolio loans, and see what the public and tax authorities have to say about that.