"When I failed, and I did, it simply meant it was time to get a job and work myself up to be able to take shot #x"

Years ago I did some real estate deals together with a few guys from rich families. The first deal went bad leaving me with debt that lasted more than 10 years to pay off. The other guys got more money from family, did a few more deals that went well and are now successful businessmen. When you don't have money you often can't afford to fail in the same way wealthy people can. The consequences are much more severe.