Would venture capital firms not be as hesitant to hand out money to people who consistently failed to return on investment?
Moridinamael was talking about permitting individuals "to try over and over again without penalty", what you describe is an example of a penalty.
In the open thread, moridinamael hypothesized that LWers would be willing to take more risks in order to become rich if they had a financial safety net. This seems like an idea worth exploring further.
What would you do if you had a financial safety net (maybe a year's worth of living expenses) to fall back on if your venture failed?