Agreed...I worked in the casino industry for many years..probably about 70 to 80% of the high rollers are/ or have been involved in some sort of criminal behaviour.
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Contracting on a daily rate plus super is pretty good for skills like SQL, SAS, Pega, Python, Alteryx or PowerBI.
Daily rates of $850 to $1,200 before tax are quite common for up to 6 month terms.
The real trick is trying to reduce your tax.
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High roller is a broad term. A worker / employee will never be a high roller no matter how successful you are at climbing the ladder, even if you make it to the C-Suite (generally speaking in Australia). Most will require some form of venture i.e. starting a business and selling it, doing property development etc, and preserving/growing wealth from those exits via investments.
For better or worse, Australia is less flamboyant with its "high rollers" because we're a nation with tall poppy syndrome, and people are encouraged to fit in. Means there's less ultra wealthy people (as a proportion of total population), but we also have better overall living standards for all. This culture doesn't exist in Asia and America which are much more capitalist.
I started with nothing and I've got half of it left!
Whenever I find myself comparing to others, I tell myself there's someone out there that started off with less, or in a more disadvantaged position and still made it. It helps me be more positive when I look at the situation like that.
I'm not too sure if I'm a high roller but I do earn enough to punt at least twice a week (average $300/punt) while still being able to pay for living expenses and have some surplus for monthly savings.
There was a point where I got a little addicted that I punted 3-4 times a week, then I felt I had enough so I went back to punting twice a week. During that period I didn't break the bank because I was getting higher returns from investment - there will come a time when you suddenly have so much money that you want to live out your sexual fantasies with it.
Financial wise I have a higher than average paying job + investments, emergency savings that can last me 6 months without a job and all debts paid off. Took me 6 years to get to this point, and during those 6 years I was only able to afford $150 shops once or twice a month.