I guess define "worse off". But I would say in both cases they ended up about the same...but I will grant they learned lots of intangibles from the experiences.

How did the end up about the same? Were they paying themselves the same salaries they would have been getting at Microsoft the whole time? Were they living more frugally than they would have been had they been working at Microsoft?

I think in terms of the kind of job position they could get going into a Microsoft after their startup, they ended up about the same as if they had been at Microsoft the whole time.

So it wasn't wasted time in that respect, and they'll be bringing in unique and different skills that they probably wouldn't have developed had they been at MS the whole time.

But...there's things like the lower pay they probably had while doing their business, and the intensity of running a failing business is very very hard mentally and physically.

Near the end, one of the guys shut down...hard...now that he's moved on he's recovering. But I think that kind of experience trails along with you for a long while.

One way to tell- if you asked them, would they say that they should have spent their time doing something else? What do you think they would say? (Or if you could just ask them, that would be even better!)

I think that's very dependent on the person and how they internalized the experience. One of them I know thinks that it was wasted years off of his life. Another feels like they learned more in those years than they did in the rest of their career combined, and it's armed them to be more effective in future endeavors.