The entrepreneur of the Old West was a man or woman who could look at a situation and find a way to capitalize on it. It could be men who came with the first hoard of gold seekers and realized he’d make more money selling the miners goods or setting up a saloon. Or it’s the woman brought to the mining area by a husband, father, or son and realizing she can get gold by either doing laundry or cooking meals. There were also men who realized mining towns needed food and staples to grow. They bought a wagon and horses and started hauling the goods. Eventually, they added more wagons and employees until they dominated the freighting in that area. And don’t forget the men with capital who invested in banks, hotels, saloons, and eventually railroads. When the railroad started moving west, men in an area would pool their finances to help build a railroad in their town hoping to instill growth and bring the larger lines to them. Some large ranches started from hard labor and determination.
And let’s not forget the entrepreneurs who walked a thin line on the right side of the law. The Gambler. This was a man or woman who could walk into a town broke and leave with half the town’s money. Sometimes legally, sometimes not. They weren't always dressed to the nines either. Most professional gamblers would wander into town dressed like any other down on their luck chump, and his cohorts would straggle in from different directions. Once they found their mark, they would act as if they were strangers yet all work toward fleecing the mark of his money. It was rare for gamblers to dress like James Garner in Maverick- unless they were headed to a contest where other 'professionals' planned to show their prowess and walk away with a hefty prize. They were in a way magicians. Using slight of hand card tricks and dealing, they tried to outfox the other gamblers.
And the last entrepreneur- the madam. Most madams of the higher class brothels bought land in their towns and either expanded their business or bought other business and kept them running.