[crankylinuxuser]

The other part is, if/when you fail....

You now have a gap of unemployment. How does your next employer see that? I know a common tactic in IT is that you're a "consultant" when unemployed. Hiring managers see through that readily.

So what then? You have a failed business, unemployed, and take a pay cut on your next job... all for the hopes that you might, just might strike it rich?

Again, this situation doesn't apply for those with well monied family and significant connections.

[nightski]

It's not a gap, you were starting a business. That is really hard and provides a lot of valuable experience along the way. Maybe just be honest about what you were doing?

[justtopost]

Part of a business plan, is an exit strategy. If yours leaves you homeless, you messed up very badly. Hyperbole does not help here.

[grandmczeb]

Few hiring managers in SV see it as a bad thing that you took time off to start a company, assuming it was a serious effort.