>A wealthy person or company who spends their money in a risky way, often by making risky investments that can offer large rewards
>Often someone who gambles with large amounts of money
>Someone who spends their money on extravagances
Many high stakes gambling games involve rolling dice, and high roller refers to winning numbers and large sums of money. These people are able to put up large sums of money without any promise of a positive return on that investment.
The only way to make large sums of money is to make risky investments. You need to be a high roller in order to afford that.
If you are a high roller, casinos will often let you stay in their hotels for free in the hopes that you will lose big amounts of money.