His company existed for a seven months in 2016 before being bought by Uber. It isn't clear (to me) if there were third party investors or what the cap table was, broadly. Purportedly 90 employees at time of sale to Uber.
That doesn’t sound right.
CGT operates by treating net capital gains as taxable income in the tax year in which an asset is sold or otherwise disposed of. If an asset is held for at least 1 year then any gain is first discounted by 50% for individual taxpayers, or by 33.3% for superannuation funds. Capital losses can be offset against capital gains. Net capital losses in a tax year cannot be offset against normal income, but may be carried forward indefinitely.
https://en.wikipedia.org/wiki/Capital_gains_tax_in_Australia
Maybe the 50% your thinking of come from this?
For most CGT events, your capital gain is the difference between your capital proceeds and the cost base of your CGT asset. (The cost base of a CGT asset is largely what you paid for it, together with some other costs associated with acquiring, holding and disposing of it.)
There are three methods for working out your capital gain. You can choose the method that gives you the best result – that is, the smallest capital gain.
CGT discount method
Eligibility: For assets held for 12 months or more before the relevant CGT event. Not available to companies. For foreign resident individuals, the 50% discount is removed or reduced on capital gains made after 8 May 2012.
Description: Allows you to reduce your capital gain by 50% for resident individuals (including partners in partnerships) and trusts 33.33% for complying super funds and eligible life insurance companies.
How to do it: Subtract the cost base from the capital proceeds, deduct any capital losses, then reduce by the relevant discount percentage. See: The discount method. Indexation method
Eligibility – For assets acquired before 11.45am (by legal time in the ACT) on 21 September 1999 held for 12 months or more before the relevant CGT event.
Description: Allows you to increase the cost base by applying an indexation factor based on the consumer price index (CPI) up to September 1999. How to do it: Apply the relevant indexation factor, then subtract the indexed cost base from the capital proceeds. See: The indexation method. Other method
Eligibility: For assets held for less than 12 months before the relevant CGT event. Description: Basic method of subtracting the cost base from the capital proceeds. How to do it: Subtract the cost base (or the amount specified by the relevant CGT event) from the capital proceeds. See: The 'other' method.
https://www.ato.gov.au/General/Capital-gains-tax/Working-out...
If you own things and sell them for a capital loss you get a tax credit to use later.
If you sell for a capital gain within 12 months then you will pay tax on the full amount of profit from the sale. For individuals this is just added to your income tax.
If you sell for a capital gain having held the asset for over 12 months you get a 50% discount to how much profit is taxed.
The tax credit for a capital loss can be used to offset a capital gain but it gets applied before any discount is applied.
I am not an accountant but I have listened to one.