The problem with this strategy is that it is impossible to engage in a high-risk/high-reward strategy like entrepreneurship where your effort has to be 100% committed to the business, especially in the first couple years and especially if you are venture backed.
There are a couple solutions to this:
1) Invest more of your wages in low risk investments to offset the monetary risk of a startup.
2) Work full-time or as a contractor whilst also working 20% of the time on your own startup to try to gain traction which would lower the risk. Though if that succeeds, you should be then reinvesting your time in another startup. It's a vicious cycle :)
There are a couple solutions to this:
1) Invest more of your wages in low risk investments to offset the monetary risk of a startup.
2) Work full-time or as a contractor whilst also working 20% of the time on your own startup to try to gain traction which would lower the risk. Though if that succeeds, you should be then reinvesting your time in another startup. It's a vicious cycle :)